CHEMICAL  HAZARD  INFORMATION
           PROFILE
       DRAFT   REPORT

Tri(alkyl/alkoxy) Phosphates

     September 23, 1985

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                    CHEMICAL HAZARD INFORMATION PROFILE*


                                DRAFT REPORT


                        TriUlkyl/alkoxy)  Phosphates


                             September 23, 1985
                                 DISCLAIMER

  This document is a preliminary draft and has not been formally peer and
administratively reviewed within the Office of Toxic Substances,- Office of
Pesticides and Toxic Substances, U.S. Environmental Protection Agency
(DSEPA).  This draft report has been prepared under contract to DSEPA by
the staff of Oak Ridge National Laboratory to provide information to assist
the Agency in its decision making, and should not be construed to represent
Agency policy.  Mention of tradenames or commercial products does not con-
stitute Agency endorsement or recommendation for or against use.

*A Chemical Hazard Information Profile (CHIP) is part of the first stage in
the assessment of risk by the Office of Toxic Substances (OTS) of chemicals
in the 1977 TSCA Chemical Substance Inventory, and enables OTS to decide on
a disposition for the subject chemical regarding level of concern and the
need for further assessment.   The CHIP contains a summary of readily avail-
able health,  environmental effects, and exposure data.  In general,  little
or no in depth critical evaluation or validation of the data is performed.
Several levels of management and technical review have been performed on
this CHIP within the Existing Chemical Assessment Division of OTS.

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DRAFT REPORT
mEMICAL HAZARD INFORMATION PROFD.E
Subj ect :
Tri(alkyl/alkoxy) Phosphates
Prepared by:
Catherine F. Sigmon
Mary Lou Daugherty
Chemical Effects Information Center
Oak Ridge National Laboratory
Chemical Name:
See Table 1.
CAS No. :
See Tabl e 1.
Da te :
September,23, 1985
Ra ti onal e :
Teratogenicity, reproductive effects, neurotoxicity, and high
production volume.
EmaJTIVE SUMMARY
This report covers available data for the series of tri(alkyl/alkoxy)
phosphates listed in Table 1. The coverage in Section A, Chemical Iden-
tity, and Section B, Physical and Chemical Properties, and Section C, Expo-
sure, were limited to tri(ethylhexyl) phosphate; tri(butoxyethyl) phosphate;
tributyl phosphate; poly(0xy-l,2-ethanediyl), .alpha.,.alpha.'-«octyloxy)-
phosphinylidene)bis(.omega.- hydroxy- (called poly-l for this report), and
poly(oxy-l,2-ethanediyl), .alpha.-(bis(octyloxy)phosphinyl)-.omega.-hydroxy-
(poly-2 for this report). ChemicAl identities, physical and chemical
, properties, and production, exposure, and use data for the remaining chemicals
in Table 1 are sumaarized in Appendix A.
A.
Worker Exposure
Current production figures for the five tri(alkyl/alkoxy) phosphates
covered in the first section of this report are as follows:
(1)
(2)
(3)
tri(ethylhexyl) phosphate
tri(butoxyethyl) phosphate
tributyl phosphate
2 mill ion pounds
2.5 to 5 million pounds
3 to 5 million pounds.
i

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Table 1. Alkyl/alkoxy Phosphates Evaluated in CHIP
CAS No
Chemical Name
78-42-2
78-51-3
126-71-6
126-73-8
512-56-1
919-62-0
1623-19-4
3033-37-2
4200-55-9
4889-45-6
6163-73-1
7332-46-9
1047-00-6
56827-95-3
57344-01-1
57344-02-2
64131-07-3

64131-08-4

64131-09-5
64131-10-8
64131-18-6
64502-13-2
7'3070-47-0
74049-24-2
Phosphoric acid. tris(2-ethylhexyl) ester
Ethanol. 2-butoxy-. phosphate
Phosphoric acid. tris(2-methylpropyl) ester
Phosphoric acid. tributyl ester
Phosphoric acid. trimethyl ester
1-Butanol. 3-methyl-. phosphate
Phosphoric acid. tri-2-propenyl ester
Tridecanol. phosphate
Phosphoric acid. tris(decyl) ester
Phosphoric acid. trioctadecyl ester
Ethanol. 2-methoxy-. phosphate
Ethanol. 2-(2-butoxyethyoxy)-. phosphate
2-Furanmethanol. tetrahydro-. phosphate

1-Hexadecanol. phosphate

Poly(oxy-1.2-ethanediyl). .alpha. ..alpha.'-
«octyloxy)phosphinylidene)bis(.omega.-hydroxy-

Poly(oxy-1.2-ethanediyl). .alpha.-
(bis(octyloxy)phosphinyl)-.omega.-hydroxy-
1-Hexacosanol. phosphate
1-Tetracosanol. phosphate
1-Docosanol. phosphate

1-Eicosanol. phosphate

1-0ctacosanol. phosphate

Poly(oxy-1.2-ethanediyl). .alpha...alpha.'.
.alpha."-phosphinylidynetris(.omega.-hydroxy-

Poly(oxy-1.2-ethanediyl). .alpha...alpha.'.
.alpha."-phosphinylidynetris(.omega.-(tridecyloxy)-

Poly(oxy-1.2-ethanediyl). .alpha...alpha.'-
(methoxyphosphinylidene)bis(.omega.-hydroxy-
i i

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(4)
pOly(oxy-1,2-ethanediyl),
. at pha. ,. al pha. ,-( (octy loxy)-
phosphinylidene)bis(.omega.-
hydroxy- (or poly-1)

poly(oxy-1,2-ethanediyl,
.alpha.-(bis-(octyloxy)
phosphiny) 1-. omega.-.hydroxy-
(or poly-2)
1 to 10 million pounds
(S)
1 to 10 million pounds
Current import volumes of acyclic phosphate esters are unknown but are
thought to be insignificant. The total U.S. market potential for tributyl
pho~hate is S million pounds, with long-term market growth estimated to be
1 tJ 2" annually. The total U. S. market potential for tri(butoxyethyl)
. phosphate is 2.S to 4.0 million pounds with long-term market growth.
estimated to be 1 to 2~ annually.
In general, functional f1 uids for hydraul ic equipment, level ing agent s
in floor polishes, plasticizers, and flame retardants in plastics comprise
the major uses for phosphate esters. For example, approximately 40-601 of
the tributyl phosphate produced is used as a flame retardant in aircraft
hydraulic fluid; 70-80. of the tri(butoxyethyl) phosphate produced is used
as a leveling agent in aqueous based floor polish; and S~ of the
tri(ethylhexyl) phosphate produced is used as a plasticizer and So. as a
flame retarder in plastics. Antifoaming agents in coatings for paper and
textiles, solvents in heavy metal ore extraction, and additives in rubber
processing comprise other important applications of the esters. Poly-1 and
poly-2 are most likely used as flow control agents for ceramic glaze,
according to the only source of information on uses found for these chemi-
cal s.
Little information was found regarding worker exposure during the pro-
duction and industrial use of .tri(alkyl/alkoxy) phosphates. During produc-
tion, the low vapor pressures of the esters, the use of closed processes
with a nitrogen blanket, and the use of protectiv~ equipment minimize
worker exposure. Dermal exposure could occur during the connecting of
transfer lines between the reactor and the drumming station and during. the
drumming or packaging of the finished product, but no data were found to
document this.
Under certain conditions, worker exposure to tributyl phosphate could
occur in conventional nuclear fuel reprocessing plants where the ester is
used as an extractant in the dissolution process. Workers using tributyl
phosphate-contaminated cyclohexane as an analytical reagent could also be
exposed to small amounts of the ester. No data are available regarding
inhalation exposure to tributyl phosphate during the use of hydraulic
fluids or inhalation and dermal exposure during uranium extraction.
The number of processing and use sites, the number of workers poten-
tially exposed during these activities, and exposure levels have been
estimated as follows: three sites, each using 12-16 workers, may be
involved in the production of tributyl phosphates; four sites, each using
12-16 workers, may be involved in the production of tri(butoxyethyl) phos-
phate; possibly only one site with six to eight workers produces
trHethylhexyl) phosphate.
iii

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Several potential means of consumer exposure to alkyl/alkoxy phos-
phates exist~ including via aerosols from office buildings. cigarette smoke
condensate. and human blood collected in commonly used plastic vacuum
tubes. Tri(butoxyethyl) and tri(ethylhexyl) phosphates were detected in
aerosols collected from office buildings. The tri(butoxyethyl) phosphate
was a component of the floor polish used in the buildings. Tri(ethylhexyl)
phosphate in concentrations ranging from 60-200 g/mL were detected in human
blood stored 2-6 months in commonly used evacuation collection tubes.
Direct human exposure to this plasticizer when similar equipment is used
for blood transfusion is possible'. TrHbutoxyethyl) phosphate has been
detected in the water-soluble portion of smoke condensate'from non-filtered
cigarettes.
Tributyl phosphate and tri(butoxyethyl) phosphate have been detected
in finished drinking water for Canadian municipalities that obtain raw
water from the Great Lakes. Tributyl phosphate concentrations varied from
0.8 to 29.5 ng/L. while tri(butoxyethyl) phosphate concentrations ranged
from 0.8 to 271.6 ng/L. The detection of tri(butoxyethyl) phosphate in tap
water can be attributed. in part. to the presence of the ester in rubber 0-
rings and seals in the tap itself. However. this is not always the case.
and in one instance 200 ng/L of the ester was detected in drinking water.
even after the pipes (and tap) had been flushed. Tri(butoxyethyl) phos- ,
phate (0.3 to 3 ppb) and tributyl phosphate (54 to 82 ng/L) have also been
detected in river and lake waters used as drinking water sources.
The presence of trialkyl phosphates in groundwater. rivers. and lakes,
suggests that the compounds are released into the aquatic environment.
This is further suggested by the fact that the compounds have also been
detected in industrial effluents. Tributyl phosphate has been detected in
plant effluents in concentrations ranging from 6.62 to 13.516.71 ~g/L.
Tri(butoxyethyl) phosphate has been detected in concentrations of 0.97 to
1607.12 ~g/L. Both tributyl phosphate and trimethyl phosphate have been
detected in effluents from municipal waste treatment facilities. Tributyl
phosphate has also been determined in leachate from a low-level radioactive
waste disposal site and in groundwater underlying a landfill.
When trialkyl phosphates are released into the aquatic environment.
degradation of the esters occurs primarily through biodegradation at
moderate to rapid rates. Rapid degradation of tributyl phosphate occurs
under aerobic. but not under anaerobic. conditions. TrHethylhexyl') phos-
phate also biodegrades. but much more slowly. It has been suggested that
the shorter the alkyl chain. the more biodegradabl e the ester. and that
degradation rates for phosphate esters are more rapid in polluted seawater
than in clean seawater. '
Trialkyl phosphates hydrolyze in water. but the process may occur too
slowly to be of environmental significance. Tri~ethyl phosphate. for exam-
ple. has a hydrolytic half-life of, 1.2 years under alkaline conditions.
Based on octanol/water partition coefficients. tri(ethylhexyl) phos-
phate and tributyl phosphate possess a moderate potential to bioaccumulate.
iv

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but this is not supported by the limited data on bioaccumulation. Under
static conditions of exposure to 4 ppm tributyl phosphate, killifish exhi-
bited bioconcentration ratios of 30 to 3S and goldfish, ratios of 6-11.
Tributyl phosphate (9.0 ng/g extracted fat) and tri(butoxyethyl) phosphate
(4.0 to 26.8 ng/g) have been detected in human fat tissue. Trl(butoxy-
ethyl) phosphate was detected in four of twelve samples.
B.
Heal th Effect s
Information on the metabolism of tri(alkyl/alkoxy) phosphates was
found for only a few of the compounds considered in this report. Based on
the proposed metabolism of trimethyl, tributyl, and tri(ethylhexyl) phos-
phates, the absorption, distribution, biotransformation, and excretion of
tri(alkyl/alkoxy) phosphates (with the exception of triallyl phosphate)
will most likely proceed rapidly, according to the following scheme:
Absorption' of trialkyl ph~sphates may occur via dermal, oral, and
respiratory routes. Trialkyl phosphates are generally transformed to
dial~yl phosphates, monoalkylphosphates, and to the corresponding alkyl
alcohols and S-alkyl-L-cysteine adducts. The metabolites are most likely.
formed through enzymatic hydrolysis (P-O cleavage), d-o-alkylation, and
oxidation of the alkyl chains, and are excreted mainly in the urine. The
metabolites may also be excreted in exhaled air and in the feces. The
unchanged parent compounds have been detected in the urine in trace amoUnts
only. .
Triallyl phosphate is mainly metabolized to allylmercapturic acid,
allylmercapturic acid sulfoxide, and a hydroxypropylmercapturic acid.
In animals, trialkyl phosphates cause various effects that include
carcinogenicity, genotoxicity, sterility, anticholinesterase activity and
neurotoxicity, hepatotoxicity, nephrotoxicity, and irritation. Because of
the pauci ty of information for a number. of the phosphates. or the variation
in test condi tions and the types of effects el iclted, it is difficult to
ide~tify trends and patterns in the toxicity of this class of ch!:,micals.
. Trimethyl phosphate and tri(ethylhexyl) phosphate were tested in.NTP
and NCI bioasssays for carcinogenicity in rats and mice, and both were
pos! tive.
Male rats fed trimethyl phosphate (SO and 100 mg/kg) for two years
developed an increased and dose-related inci~ence of subcutaneous fibromas
(P=0.036, high dose). Female rats fed trimethyl phosphate did not exhibit
significantly increased incidences of any tumors.
In female mice, orally administered trimethyl phosphate (SO and 100
mg/kg for two years) induced highly malignant adenocarcinomas of the
. uterus/endometrium (P=0.004, high dose). There was no significant increase
in the incidence of any tumors in male mice treated with trimethyl phos-
phate.
v

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Male rats fed tri(ethylhexyl) phosphate (2,000, or 4,000 mg/kg) for 2
years had a do.se-related increased incidence of adrenal pheochromocytomas
(P=0.026 low dose; P=0.004, high dose), when compared to that of the vehi- .
cle control group. However, the incidence of these tumors in the vehicle
contoIs of the study was very low (4~) when compared to that of the con-
trol s in two previous 'studies (2S~) or with the historical incidence of the
tumor observed throughout the bioassay program (18~). The male rats also
had a statistically significant dose-related increasing trend in the
incide~ce of thyroid neoplasms, but the increases were not significant in
pair-wise comparisons. Based on these results, the authors concluded that,
under the condi tions of the study, there was" equivocal evidence of carci-
nogenicity" in male rats treated with tri(ethylhexyl) phosphate. There was
fIno evidence of carcinogenicity" in female rats fed 1,000 or 2,000 mglkg of
the compound.
Female mice fed tri(ethylhexyl) phosphate (1000 mglkg, high dose) for
two years had a statistically significant increase in the incidence of
hepatocellular carcinomas (P=0.007); male mice did not. The' investigators
concl uded that, under the condi tions of the biosaaay, there is "some ev.i-
dence of carcinogenicity" in female mice treated with 1,000 mg/kg of the
compound .
Limitedgenotodcity dat'a, found on four of the compounds inclUded in
this report, indicate that tri(alkyl/alkoxy) phosphates may be weakly to
non-mutagenic. Trimethyl phosphate, the only one of these compounds to
have been tested extensively in various assays, was weakly mutagenic in
Salmonella and in E. coli with and without metabolic activation, and in the
mouse dominant lethal assay, the bone marrow cytogenetic assay, and the
sperm abnormality test~ but was negative in the host-mediated assay. The
compound is a demonstrated alkylating agent, and is used as such in indus-
try. Tributyl phosphate was negative in Salmonella and E. coli assays
without activation, and tri(ethylhexyl) phosphate and tri(butoxyethyl)
phosphate were negative in Salmonella with and without activation. Geno-
toxicity data for other compounds were not found.
. Trimethyl phosphate induced te~porary dose-dependent sterility andlor
reduced fecundity in rats and mice at daily doses ranging from 100 mg/kg
for a month to 7S0 mg/kg in a single dose, and in Drosonhila when added to
the growth medium at concentrations of 0.002-0.00S M. Threemechanisms
potentially responsible for the sterility effect of trimethyl phosphate
have been proposed: reduced choline andlor carnitine acetyl transferase
activity resulting in reduced sperm motility, reduction in circulating tes-
tosterone, and, in Drosonhila, disruption of normal loop formation on the
Y-chromosome. Tributyl phosphate, administered at doses of 170 or S10
mg/kg for 14 days, induced microscopic degenerative changes in the semini-
ferous tubules of the rat, and~ when injected into hen eggs at S mg/egg,
was" slightly teratogenic".
Information on neurotoxicity was found on four of the compounds.
There was no. evidence that any of the compounds caused delayed neurotoxi-
city; however, functional and morphological changes have been observed in
the nervous systems of animal s following treatment with trimethyl, tribu-
tyl, tri(butoxyethyl) and tri(ethylhexyl) phosphate esters. For example:
vi

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(1) Deterioration of comB tioned avoidance has been observed in dogs fol-
lowing ~xposure to atmospheric levels of tri(ethylhexyl) phosphate (10.8 to
85 mg/m ); (2) A significant reduction in nerve conduction velocity aDd an
increase in tho refractory period were observed following treatment with
tri(butoxyethyl) phosphate (-260-510 mg/kg for 18 weeks). tributyl phos-
phate (305 ms/kg for 14 days), and trimethyl phosphate (-1.200 mg/ks/day
for 1-4 months); (3) Trimethyl (5-. in the diet for 9 weeks) aDd tributyl
phosphates (266 mg/ks. singl e dose) did not have antichol inesterase
activity in animals. as do certain other organophosphorus compounds; and
(4) Paralysis and narcosis have been induced in animals with lethal and
sublethal doses of trimethyl aDd tributyl phosphates. but large or lethal
doses of triallyl. triisobutyl. and tri(ethylhexyl) phosphates did not pro-
d uce paralysi s.
In humans. trialkyl phosphates may cause skin. eye. and respiratory
irritation. 'Tributyl phosphate is severely irritating to humans. while
tri(ethylhexyl) aDd tri(butoxyethyl) phosphates are slightly irritating.
c.
Environmental Effects
Toxicity studies in environmental species were found mainly for
trimethyl and tributyl phosphate.
Excretion studies with tributyl phosphate in the killifish (Orvzeas
latines) demonstrated that the chemical was rapidly taken up. reached a
steady-state concentration in one day. and was completely eliminated after
24 hours in cl ean water. Metabol ism studies were not found for other chem-
icals or environmental species.
Forty-eight hour LC values for tributyl phosphate in environmental
species vary from 2.1 mg7~ for the water flea (Qanhnia maana) to 14.6 mg/L
for the rainbow trout (Salmo aaitdneri). indicating the chemical to be of
moderate acute toxicity in aquatic species. As in laboratory animals.
trimethyl phosphate also caused reproductive effects when tested in males
or on sperm of several environmental species. The ester (at 2.43 g/L for.
100 days) caused disruption of spermatogenesis in guppies at the pre-
meiotic stage (Hanna 1982); reduced the percentage of cleavages of the
Xenonus ova. caused furrowing of the animal pole without cleavage of the
vegetal pole. and interfered with the sperm motility (at concentrations of
20-120 mg/mL. with exposure times ranging from 30 minutes to 2 hours)
(Hem~orth and Watdhaugh 1978. Jones and Jackson 1974); and reduced fertil-
ity in qudls by acting mainly on spermatids and spermatazoa (at 250 and
562 mg/kg) (Jones et ale 1972). Trimethyl phosphate. at 2.5-'. also reduced
the number of eggs laid and percent hatch of eggs of the two-spotted spider
mite. while lower concentrations (0.1-0.2-') of tributyl phosphate. triiso-
butyl phosphate. and triallyl phosphate had no effect on reproduction (Pen-
man and Osborne 1976).
Trimethyl phosphate a150 depressed fertilization and the rate of
embryonic development in the plant Niaella damascena. Treatment also sig-
nificantly retatded the onset of mitosis and prolonged the mitotic 'cycle
and induced mutations in almost completely formed embryos.
vii

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. In axenic strains of 13 algal species. tributyl phosphate inhibited
growth at concentrations ranging from 2S to 2100 mglL (EC100)' and in other
microorganisms. growth was inhibited at 4.1 to SO mg/L. Pseudomonas was
one of the least sensitive of the species tested. exhibiting a toxicity
threshold of >100 maiL.
viii

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I.
A.
B.
c.
D.
E.
F.
G.
II.
A.
B.
c.
D.
TABLE OF CONTFNTS
Ch em! cal
Hazard Information Profile
Tri(alkyl/alkoxy).Phosphates
EXEaJTIVE mMMARY ..............................................
Summary of Available Data
.... .............................. ....
Chemical
Ide nt i ty ..............................................
Physical
Expo sure
and Ch em i cal
Pr ope r tie s ...............................
.............. ... ..... ... ... ... ........ ................
1.
2.
3.
Worker Exposure............................................

Cons1II1er Expo sure. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .

Environmental Exposure .....................................
Heal th Eff ect s
. ..... ..... ... ..... ... ............... ............
1.
2.
3.
4.
5.
6.
7.
Metabol ism
........ ........ .......... ..... .......... ... .....
I.,e th 81 i ty ........................................'. ~ . . . . . . . .

Carcinogenic! ty ............................................

Genotoxi ci ty ......................... '. . . . . . . . . . . . . . . . . . . . . .
Teratogenicity/Reproductive Effects
................... .....
Other Eff ect s ..............................................
Case Reports and Epidemiological
Studies ...................
EnviroDlllental
Eff ect s ..........................................
1.
2.
3.
4.
5.
6.
Me ta bol i am .................................................
I..e:thal i ty ..................................................

Reproduct i OD .."......................................... ~ . . .

Growth. and Behavior ........................................

Abi oti c Eff oct s ............................................
Other Effects.
. . . . . . . . . .,. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Ed sting Standards.
Other ReI evant
and Recommendations ...........
He gul a ti on s.
Inf orma ti on . .,. . . . . . . . . . . . . . . . . '. . . . . . . . . . . . . . . . . .
Ref erence 8
. . ... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
Literature
Ci t 8 d ...............................................
Supplemental
Secondary Sources Searched
InŁ' orms t ion. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .
.... ................ .................
1.
2.
3.
Books
. . . . . . . . . . . . .'. . . . . . . . . . . . . . . . . . . ... . . . . . . . . . . . . . . . . . . . .
Da ta Ba S8 S ............'.....................................

Search Strategy.......................................... ...
Chemical
Specific Secondary Sources Searched ...................
APJlENDIX A [[[
ix
i
1
1
1
1
1
13
15

22
22.
27
27
42
51 .
54
64

64

64
64
64
68

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TABLES
Chemical Hazard Information Profile
Tri(alkyl/alkoxy) Phosphates
TABLE
PAGE
1
2
3
Alkyl/alkoxy Phosphates Evaluated in CHIP...............................ii
Physical and Chemical Properties of Tri(alkyl/alkoxy) Phosphates.........2
Current Producers and Production Data for Tri(alkfl/alkoxy) Phosphates...7
4
5
6
Uses of Commercially Available Phosphate Esters..........................9
Alkyl/alkoXy Phosphates ill Plant Effluents..............................16.
Lethality of Tri(alkyl/alkoxy) Phosphates in Experimental Animals.......23
of Lesions in Trimethyl Phosphate-Treated Male Rats......... .28
of Lesions in Trimethyl Phosphate-Treated Female Rats........31
of Lesions in Trimethyl Phosphate-Treated Male Mice...........35
of Lesions in Trimethyl Phosphate-Treated Female Mice........37
of Lesions in Tri(ethylhexyl) Phosphate-Treated Rats.........41
of Lesions in Tri(ethylhexyl) Phosphate-Treated Mice.........43
7 Incidence s
8 Incidence s
9 Incidence s
10 Incidence s
11 Incidence s
12 Incidence s
13 Genotoxicity of Tri(alkyl/alkoxy) Phosphates............................45
14 Reproductive and Teratogenic Effects of Alkyl Phosphates................52
15 Acute Toxicity of Tri(alkyl/alkoxy) Phosphates..........................56
16 Subacute Toxicity of Tri(alkyl/alkoxy) Phosphates.......................58
17. Subchronic Toxicity of TrHalkyl/alkoxy) Phosphates.............~........59
18 In Vitro Effects of Tri(alkyl/alkoxy) Phosphates.........................61
19 Skin and Eye Irritation Studies with Tri(alkyl/alkoxy) Phosphates.......62
20 Lethality of Phosphates to Environmental Species........................65
21 Reproductive Effects of Alkyl Phosphates on
Env iroDlllental Animal Spe 01 e s. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .67 .
22
Growth Inhibition by Tributyl Phosphate in Environmental Species........69
x

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I.
S~ary of Available Data
Trioctyl phosphate is a commonly used syno~m for two chemicals, CAS
No. 78-42-2 [tri(ethylhexyl) phosphate of this report] and CAS No. 1806-54-
8 (trioctyl phosphate, not included in this report). Occasional reports
contained information for" trioctyl phosphate" with no further identifica-
tion of the compound. In these cases, it is noted in the text or tables
that the identity of, the compound has not been specifically established.
A.
Chemical Identity
See, Table 2.
B.
Physical 'and Chemical Properties
S'ee Tabl e 2.
C.
Expo sur e
1.
Worker Exposure
a.
Production/Importation/Producers
Production of acyclic phosphates, in general, rose from 10 million
pounds in 1960 to 14 in 1965 and reached peak production of 29 million
pounds in 1972 and 1974 (SRI 1981-1982). Production for 1979 was 19 mil-
l ion pounds.
The production range (includes importation volumes) statistics from
the initial public (non-CDI) TSCA Inventory (USEPA 1983) were reviewed for
tri(ethylhexyl) phosphate (CAS No. 78-42-2), tri(butoxyethyl) phosphate
(CAS No. 78-51-3), and tributyl phosphate (CAS No. 126-73-8). Between
, 110,000 and 1,101,000 pounds of trHethylhexyl) phosphate, between
2,011,000 and 20,110,000 pounds of tri(butoxyethyl) phosphate, and between
1,100,000 and 11,003,000 pounds of tributyl phosphate were reported as
. '
produced/imported in 1977.
A review of the produotion range (includes importation volumes)
s18 ti stics for pOly(oxy-1,2-ethanediyl),. alpha. ,. alpha. '-( (ootyloxy)-
phosphiuylidene)bis(.omega.-bydroxy- (CAS No. 57344-01-1) (called poly-1
. This production range information does not inolude a~
product,ion/ importa tion data olaimed as conf idential by the person(s)
reporting for the TSCA Inventory, nor does it include any information
which ,would oompromise Confidential Business Information. The data
submitted for the'TSCA Inventory, including produotion range
information, are subjeot to the limitations contained in the Inventory
Reporting Regulations (40 CPR 710).

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Table 2.
Physical and Chemical Properties of Tri(altyl/alkoxy) Phosphates
A.
B.
Chemical Identity
. 1.
CAS Registxy Number
2.
Chem ical NUle:
3.
Synonyms:
4.
Structural formula:
5.
Molecular formula:
Physical and Chemical
Properties
1.
Moleoular weight:
2.
Physical state:
3.
Melting point (OC):
Freezing point(OC):
4.
Boiling point (OC):
78-42-2
Phosphoric acid,
tris(2-ethylhexyl) ester
DisflUloll TOF
Fluol. TOF
TOF
Tri(2-ethylhexyl) phosphate
Triootyl phosphate
Tris(2-ethylhexyl) phosphate
I-Bexanol. 2-ethyl-. phosphatea
. e
[C4 \ ar(C2B5 )CB20J 3PO
a
C24Bn04P
434.64
Colorless liquide
-9og (pour point)
-74e (pour point)

< -90e
-70q
216 at 4- Bge
7S-Sl-3
Ethanol. 2-butoxy-.
phosphate
2-Butoxyethanol. phosphate
. KP 140
Phosphorio acid. Tris(2-butoxyethyl)
oster; 1'8EP
Tri(butoxyethyl) phosphate
Tri(2-butosyethyl) phosphate
Tributyl oellosolve phosphate
Tris(2-butoxyethyl phosphate)a
e
[CB3(CB2)30(CB2)20J3PO
a
C1SB3907P
39S.54
Slightly yellow
oily liquide

< -70g (pour point)
-70e
215-228 at 4- Bgg
126-73-8
Phosphoric acid.
tributyl oster
Butyl phosphate
Celluphos 4
Dhflaaoll 1'8
1'8P
Td-n-buty 1 phospha te
Tributosyphosphine oxide
Tribntyl phosphatea
o
(C.\O)3PO .

a
C12B2704 P
"1
266.32
Colorless. b
odorless liquid
< -80b
b
289 with de008postion 6
137-145'C at 760 ma Bg

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Table 2.
(Continued)
78-51-3
78-42-2
126-73-8
5.
SolubU ith~ in
Water:
Insolublee; 600 P8/Lh;
0.01~ (at 250C)P

Soluble in mineral
oUt lasolinee
4.23f
0.9260 (20/200C)e
Vapor pressure:
1.8 I: 10-4 IUD HI at 250Cr
0.23 IIJD HI at lS00Cd
, 0.10 IUD HI a t 150° cP
0.20 IUD HI at 2000CP
1.441 e
Stable for 2 wks at.
60°C and for 3 years at
4°Cs

21soCe
17. 74~
-7.3~ at 250CP
Insoluble or limited
solubil ity in
Ilycerol. Ilycol. and
certain amines; soluble in
mOst other orlanic liquidse
4 .781
1.02 at 200Ce
Vapor pressure:
1.2 I: 10-4 am HI at 2SoC
0.03 IIJD HI a~ lS00Ci
1.6 .. HI at 2000CP
1.434 e
13.8i
2230Ce; 1320C (CC)q
1 mL per 16S mL waterb;
0.1~0
.1 iquidsb
4.00f
2.90m
4.20m
3.93m
2.75m

0.9727 at 2soCt
Vapor pressure:
0.07 8m HI at 2soCr
7.3 IUD HI at lS00Co
127 am HI at 1770Cd
> SOO IUD HI at 2000Co
w
Non-aqueous solvents:
6.
Dissociation constant:
1.421Sb
9.2d'
55.1 cah/am at 2890Ce
38.6 seconds 'at 29.4°Ce
1460C (COC)e
, 14.9Sd
Reactivity: As do other esters. trialtyl/alkoJ:y phosphates underlo hydrolysis to the parent acid and alcohol (Morrison
and Boyd 1973). In acidic sol~tioD. all phosphate esters are readily oleaved to phosphoric acid. but iD alkal'ine solutioD
only trialtyl phosphates are hydrolyzed bi the removal of only One altoJ:y aroup (MorrisoD and 80yd 1973). When heated to
the point of decomposition. trialtyl/alkoJ:y phosphates emit tOl:io fumes of POI: (Sal: 1984).
7.
PartitioD coefficieDt
(101' P) ootanol/water:
cyclohel:aDe/water:
DethfeDe chloride/water:
benzeDe/water:
N-heptane/water:

DeDsity (Specific Iravity):
8.
10.
Other
a.
Refraotive iDdel:,(at 2S0C):
Vapor density (air = 1):
LateDt heat of vaporizatioD:
Saybolt visoosity:
Stability iD storale:
b.
c.
d.
e.
f.
Flash point
11. ConversioD factors
(111/.3 =1 ppm):
12.

-------
Tabl e 2
(continued)
.--.-----.-.
A. Chemical Identi ty     
 1. CAS Registry Number 57344-01-1  57344-02-2 
 2. Chemical Name:  Poly(oxy-1.2-ethanediyl). Poly(oxy-1.2-etbanediyl). 
      . at pha. .. al pha. '- «octy loxy) .alpha.-bis(octyloxy) 
      phosphinylidene)bis(.omega.- pbospbinyl)-.omega.- 
      bydroxy-(9CI) bydroxy- (9Cl) 
 3. Synonyms:   Poly-1  Poly-2 
 4. Structural formul a: Not found  Not found 
 5. Molecular formula: (C2-R4-0)mult-(C2-R4-0)mult-Cs-R19-04-P (C2-B4-0)mul t-C16-H35-04-P 
B. Physica~ and Chem ical    
 Properties      
 1. Molecular weight: 479n  503n 
 2. Physical state: Not found  Not found 
 3. Mel ting point (OC): Not found  Not found .;:.
  Freezing point(OC): Not found  Not found 
 4. Boil ing point (OC): Not found  Not found 
 5. Sol u.bil ities in    
  Water:   Water dispersablen Water dispersablen 
  Non-aqueous sol vent s: Soluble in  Soluble in 
      pol ar sol vent s; pol ar sol vent s; 
      reI atively insol ubI e relatively insoluble 
      in nonpolar solventsn in nonpolar solventsn 
 6. Dissociation constant: Not found  Not found 

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Tabl e 2
(continued)
57344-01-1
.57344-02-2
7.
Partition coefficient
(loS P) octanol/water:
8.
Density (Specific sravity):
.9.
Vola t11 ity:
10. Other    
 a. Refractive index (at 250C):
 b. Vapor density (air = 1):
 c. Latent heat of vaporization:
 d. Saybol t visco si ty :
 e. Stab11 ity in storase
 f. FI ash point  
11. Conversion factors  
 (ms/m3 '" 1 ppm):  
12.
Not found
Not found
Not found
Not found
Vapor pressure:
Not found
Vapor pressure:
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Not found
Reactivity: As do other esters. trialtyl/altoxy phosphates underSo hydrolysis to the parent
acid and alcohol (Morrison and Boyd 1973). In acidic solution. all phosphate esters are
readily cleaved to phosphoric acid. but in altaline solution only trialtyl phosphates are
hydrolyzed by the removal of only one altoxy sroup (Morrison and Boyd 1973). When heated to
the point of decomposition. trialtyl/altoxy phosphates emit toxic fumes of POx (Sax 1984).
(J'I
aMEIX.ARS II aJEK.INE 1985
bWindholz et al. 1983
cMactison et al. 1981
dSandmeyer and Kirwin 1981
eOawley 1981
fSaeser et al. 1979
SSears and Touchette 1980
hOollifield 1979
iSax 1984
jDun 1979
tWeast et al. 1984-1985 .
lPomona Collese 1984
mAtiba et al. 1977 (as reported in Pomona Collese 1984)
nDuPont 1985
°Monsanto (no date)
PFMC (no da te)
qBors-Warner (1983)
rUSEPA (1985) .
sNTP .1984

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6
for this report). and poly(0xy-l.2-ethanediyl. .alpha.-(bis-(octyloxy)-
phosphiayl)-.omega.-hydroxy- (CAS No. 57344-02-2) (poly-2 for this report).
which are listed in 'the initial TSCA Inventory (USEPA 1983). has shown that
no 1977 production/importation was reported or that 'all of the production
range data reported were claimed as confidential by the manufacturer(s) or
importer(s) and cannot be disclosed (Section 14(a) of the TSCA. U.S.C.
. '
2613(a». '
In 1979. production volumes for three of the phosphate esters ittcluded
in this section were as follows (SRI 1981-1982): tributyl phosphate. 5
million pounds (may have been greater according to industry sources);
tri(butoxyethyl) phosphate. 2.5 million pounds; trioctyl phosphate (not
known if this is the synoaym for 78-42-2). 2.5 million pounds. '
In order to identify current producers and production ,levels of the
five phosphate esters listed above. the USEPA contacted those companies
listed as producers in either the 1977 TSCA Inventory or the SRI 1984 .
Directory of Chemical Producers (USA) (USEPA 1985). The companies and
current production estimates are listed in Table 3.
According to Monsanto (1985b). th~ total U.S. market potential for
tri(butoxyethyl) phosphate is 2.5-4.0 million pounds. with loni-term market
growth estimated at 1-2~ per year. The total U.S. market potential for
tributyl phosphate is approdmate1y 5 million pounds. with long-term market
growth estimated at 1-~ per year (Monsanto 1985b).
Current separate import data were not available for acyclic phosphate
esters. However. according to SRI (1984. as reported in USEPA 1985). total
imports for these chemicals are not expected to be significant.
b.
Production Methods
Acyclic triphosphates are commercially prepared from phosphorus oxy-
chloride and the appropriate alcohols (SRI 1981-1982. USEPA 1985). '
Phosphorus oxychloride reacts violently with water or moisture in the
air. and consequently. the reaction is usually contained in a closed pro-
cess and is run under a dry nitrogen blanket (USEPA 1985). When the reac-
tion is completed. the triphosphate may be washed with a mild basic solu-
tion and th~n with clean water which is subsequently removed by decanting
and vacuum distillation (USEPA 1985). Depending on the amount produced.
the triphosphate is then pumped into tank cars. tank wagons. 55 gallon
drums or smaller containers for shipment to customers. Hydrochloric acid
vapor. the byproduot of the reaction between phosphorus oxychloride and the
alcohol. is condensed and collected. and is either sold or recycled. If
sale or recyole is not feasible. the hydrochloric acid is neutralized and
dispo se d of as a sa! t (USEPA 1985).
. The data submitted for the TSCA Inventory. including production range
information. are subject to the limitations contained in the Inventory
Reporting Regulations (40 CPR 710).

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7
Tabl e 3.
Current Producers and Production Data for Alkyl/Alkoxy Phosphates
Chem ical
(CAS No.)
Producer/Location
Total Production
Volume Estimate
(Millions of Pounds)
Tributyl phosphate
(126-73-8)
FMC Corp.
Nitro, WV

Monsanto Co.
Loca tion ana
3-5
Stauffer Chemical Co.
Gallipolis Ferry, IV
Tri(2-butoxyethyl)
phosphate (78-51-3)
Borg-Warner Chem.
Morgantown, IV

FMC Corp.
Ni tro, . WV
2.5-5
Monsanto Co.
Loca tion an

Stauffer Chemical Co.
Gallipolis Ferry, WV
.Tri(ethylhexyl) phosphate
(78-42-2)
Borg Warner
Morgantown, WV
2b
Poly-!
(57344-01-1)
E.I. du Pont
de Nemours , Co.
(location not given)
.1-10
Poly-2
(57344-02-2)
E.I. du Pont
de Nemour s
(location not given)
1-10
aOBI = Confidential Business Information .
bEstimated production for 1983. (SRI 1984, as reported in USEPA 1985)

Sources: .For tributyl, tri(2-butoxyethyl), and tri(ethylhexyl) phosphates:
Personal contacts, as reported in USEPA (1985)
For poly-1 and poly-2: du Pont (1985)

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8
, Many experimental procedures for preparing these compounds use the
same general approach as that used for commercial preparation. but specific
experimental conditions or catalysts may vary in order to enhance the reac-
tions. Trialkyl phosphate's have been prepared by' treating phosphorus oxy-
chloride with C6-16 aliphatic aJcohols under certain temperature and pres-
sure conditions wlth Mg as a catalyst (Arct et al. 1975. as reported in
Chem Ab~tr 83:163757e). Tributyl phosphate (purity. 99~) was produced in
vacuo without a catalyst by reacting the respective alcohol'with phosphorus
oxychloride under appropriate conditions of temperature and pressure (Fer-
nanda et al. 1972. as reported in Chem Abstr 79:91582m). The use of low
temperatures (-5 to 25°C) during the first phase of the reaction eliminated
secondary reactions. Phosphorous oxychloride has also been used as an
esterification agent for tributyl phosphate under various conditions of
temperature. pressure, and presence of other compounds (Ismail et al. 1970,
as reported in Chem Abstr 73:98377h; Yamamoto and Torisu 1980, as reported
in Chem Abstr 93:167882w).
Tri(butoxyethyl) phosphate has been prepared by treating vaporized
butoxyethanol with sodium hydroxide. The product is then added to phos-
phorus oxychloride to form tri(butoxyethyl) phosphate (Parsons and Finley
1983, as reported in Chem Abstr 100:34705g). Tri(ethylhexyl) phosphate has
also been formed by the esterification of its corresponding sodium alcoho-
late with phosphorus oxychloride (Orwoll 1970. as reported in Chem Abstr
72:89768p). '
Another general method for producing trialkyl phosphates involves the
reaction of phosphoric acid with alkyl halides in the presence of amines to
form the corresponding trialkyl phosphate. Tributyl phosphate has been
prepared using this method. (Mitsui Toatsu Chemicals 1981. as reported in
Chem Abstr 96:85075h).
c.
Uses
In general, use in functional fluids for hydraulic equipment is a
major application for phosphate esters, while use as plasticizers is minor
(SRI 1981-1982). The main uses for the individual esters covered in this'
report are summarized below, and estimates of the percentages of each used
in typical formulations are listed in Table,4.
1) Tributyl Phosphate
The primary uses of tributyl phosphate are as a flame retardant in
hydraulic fluid for aircraft control systems and as a solvent in heavy
metal ore extracti~n (SRI 1981-1982, USEPA 1985. Monsanto 1985b), particu-
larly uranium ore (USEPA 1985). .
Some 40 to 6~ of the production volUme of tributyl phosphate is used
as a flame retardant in petroleum-based aircraft hydraulic fluids. Formu-
lation concentrations are typically 50 to 6~ of the hydraulic fluid.
These hydraulic fluids are usually prepared by metering and pumping the
individual components into a mixing tank where the components are blended.
Upon completion of ~he blending. the fluids are then drummed into 55 gallon
drums or tank trucks which are shipped to distributors/customers. When

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Tabl e 4.
Uses of Commercially Available Phosph~t~ Esters
Chem ical
(CAS No.)
Use
.. of Production
in Use (Estimate)
.. of Ester in
Use Formul ation
Tributyl phosphate
(126-73-8)
Tri(2-butoxyethyl)
phosphate <.78-51-3)
Tri (e thy 1 hexy 1)
phosphate (78-42-2)

POly-1
(57344-01-1)

Poly-2
(57344-02-2)
Flame retardant in
aircraft hydraulic
fl uid
Solvent in ore extraction
Antifoaming agent in coat-
ings for paper. textiles.
etc.

Leveling/plasticizerb agent
in aqueous based floor
pol ishes
Plasticizer in plastics
Antifoaming agent

PI asticberl f1 ame re-
. tarder in plastics

Flow control agent for
ceramic gl azec
Flow control agent for
ceramic glazeC
40-60
50-60
10-20
5-10
NFa
0.1-0.2
70-80 1-2 
10-20 20-50 
5-10 0.1-0.2 
50 20-30 \0
50 20-50 
NFa NFa 
NFa NFa 
!IN
b F = Not found
According to Monsanto (1985b). tri(2-butyoxyethyl) phosphate is used
in floor sealers and pol ishes .only as a level ing agent.
c
Use based on information found in U.S. Patent 3.898.091. the only
citation found for these two phosphates (USEPA 1985).
Source s:
Product literature contacts for FMC. Borg-Warner. Stauffer.
Monsanto (USEPA 1985)

-------
10
used, the fire-retarded hydraulic fluids are pumped into the system, which
is bled to ensure that no air remains in the hydraulic system. The bleed-
ing of the hydraulic system may result in small amounts of overflow from
the hydraulic system.
Tributyl phosphate is used in the Purex (Plutonium Uranium Reduction
Extraction) process for the separation of plutonium and uranium f!~ spent
nuclear fuel elements (Weigel 1982). It is also used to purify U pro-
duced from the bombardment of protactinium (Weigel 1983). Many other
metals can be extracted using tributyl phosphate as the solvent. Cerium IV
is separated from trivalent lanthanons (Silvernail 1979). Polonium can be
separated from lead and bismuth (Kohman 1982) and niobium, from tantalum or
impurities in niobium ore (Payton 1981). Tributyl phosphate is also used
to extract indium (Milner and White 1981); thorium (Katzin 1983); uranyl
nitrate (Teh and Baird 1980); and, in an analytical procedure, strontium-90
(Baratta and Reavey 1969). It is used as an ion-association reagent (from
acid media) for metals (McDuffie 1983) and also used in liquid-liquid
extraction as a modifier in a mixture with an extractant and a diluent (Teh
and Bd rd 1980)..
Tributyl phosphate is also used as a defoamer in the paper industry
(Baum et a!. 1981) and in textile sizers, inks, etc. (USEPA 1985). Lac-
quers, plastics, and other materials incorporate it as a plasticizer
(Gosselin et a!. 1981). Tributyl phosphate is a compatible .plasticizer for
the following: cellulose acetate, cellulose acetate-butyrate, cellulose
nitrate, ethylcellulose, poly(methyl methacrylate), polystyrene, poly(vinyl
acetate), poly(vinyl butyral), poly(vinyl chloride) (Sears and Touchette
1980), and chlorinated rubber (Monsanto 1985a).
Minor uses of tributyl phosphate as a chemical reagent include the
following: in combination with other chemicals to split viruses for the
preparation- of subvirion vaccines (Jegede et al. 1983); impregnated into
resins that remove trace metal impurities from acid solutions (Warshawsky
et al. 1979, as reported in Chem Abstr 91:58266m); as a coating on high-:
performance liquid chromatographic columns that are used to quantify uri-
nary porphyrins (Johansson and Niklasson 1983, as reported in DIALOG
[BIOSIS] 1985); for extraction of oxalic acid in a high-performance liquid
chromatographic method to determine oxalic acid in urine (Imaoka et al.
1983, as reported in MEDLARS II [HEDLINE] 1985); and as a pigment grinding
~ssistant, a very minor use (Monsanto 1985b). .
The following uses for tributyl phosphate have been described in
patents, but it is not known if these have commercial application: in pro-
duction of phosphate ester greases (Saraceno 1967, as reported in Chem
Abstr 67:83690g); as a plasticizer in a coating of heat-transferable ink on
a thermosensitive inked element for non-impact printers (Knirsch and
Gianolini 1983, as reported in Chem Abstr 99:61744m); as a part of the sol-
vent system used to recover sulfuric acid from wastewater (Morimoto et al.
1979, as reported in Chem Abstr 91:145645c); in a coating of paper used in
a system for providing dark permanent fingerprints (Buerkley et al. 1980,
as reported in Chem Abstr 94:55970n); as a component of amino acid-
concentrating membranes (Agency of Industrial Sciences and Technology 1982,

-------
11
, as reported in Chem Abstr 98:144712e); in polymer mixtures used to make
containers for storing adhesives (Takaoka Chemical 1983, as reported in
Chem Abstr 100:211222v); as an additive to herbicides that may enhance
their penetration or prevent their crystallization (Johnson 1984, as
reported in Chem Abstr 101:186151g; Nishiyama et ale 1973, as reported in
MEDLARS II [TOXBACK65] 1985; Albrecht et ale 1983, as reported in MEDLARS
II [TOXLINE] 1985); in preparation of clear cosmetic oil (Takemoto and
Otani 1980, as reported in Chem Abstr 93:79878u).
The potential uses of tributyl phosphate in the following areas have
also been studied: as an additive to give antistatic properties to thermo-
plastic polymers (Vasilenok et ale 1976, as reported in Chem Abstr
85:47472a); as a part of a polymer used for tooth implants (Bodosh et 81.
1974, as reported in MEDLARS II [TOXBACK 65] 1985).
2) Tri(ethylhexyl) Phosphate
Tri(ethylhexyl) phosphate is used mainly as a plasticizer/flame-
retardant in vinyl ,plastics and synthetic rubber compounds (USEPA 1985).
The use of this ester resul ts in (1) reduced tackiness with vinyls at high
temperatures, (2) impact resistance and f1exibility at very low tempera-
tures, (3) better compatibility with PVC resins (Borg-Warner 1983; as
reported in USEPA 1985), and (4) addition of some flame-retardant proper-
ties to the resins (USEPA 1985). Tri(ethylhexyl) phosphate is a compatible
plasticizer with the following: cellulose nitrate, ethylcellulose,
poly(vinyl butyral), poly(vinyl chloride) (Sears and Touchette 1980).
Tri(ethylhexyl) phosphate is a component of some solvent mixtures used
in nuclear fuel reprocessing (Tallent et ale [date not given], as reported
in DIALOG [NTIS] 1985). It is used in the separation of cerium(IV) from
trivalent lanthanons (Silvernail 1979) and is used as a solvent in the 2-
alkylanthraquinone process for producing hydrogen peroxide (Chung 1978).
Barnhart (1982) discussed the use of trioctyl phosphate to maintain good
, low ,temperature properties in neoprene. The CAS Number was not given;
therefore, it is not certain that narnhart was referring to the synomym for
tri(ethylhexyl) phosphate.
Patents have been issued for the following uses of tri(ethylhexyl)
phosphate, but it is not known if these have commercial application: as an
additive for preserving red cell morphology during storage of whole blood
(Estep 1983, as reported in Chem Abstr 99:156133a); as part of a mixture
containing isocyanate prepolymers that can be, used as an adhesive or rein-
forcing coating of glass and plastics (Koenig et ale 1983, as reported in
Chem Abstr 99:55166h); in a mixture containing poly(vinyl butyral) that is
used to produce a film for the intermediate layer in safety glass (Bermann
and Fabian 1984, as reported in Chem Abstr 101:172440p); in preparation of
clear cosmetic oil (Takemoto and Otani 1980, as reported in Chem Abstr
93:79878u); in production of powdered bis(2-ethylhexyl) sodium phosphate
(Lyal in et a1. ' 1973, as reported in Chem Abstr 80: 60S04d). Wesch1er
(1980) sta te,d that tri(e thy lhexy l) phosphate had been proposed as a' syn-
thetic lubricant.

-------
12
Kreevoy and Nitsche (1982) explored the use of an amine solution in
trioctyl phosphate (CAS Number not given) carried on a porous. plastic sup-
port and used in a modified dialysis cell for removing nitrate from drink-
ing water.
3) Tri(butoxyethyl) Phosphate
According to Monsanto (1985b) and USEPA (1985). the primary use of
tri(butoxyethyl) phosphate is as a leveling agent/plasticizer for synthetic
floor polishes and sealers. It prOmotes flow. prevents puddling. and elim-
inates streaking and contracting of the film as the polish dries (USEPA
1985). The U.S. consumption of floor sealers (approximately 9 million gal-
lons) equates to approximately 300.000 Ibs of td(butoxyethyl) phosphate
per year; the U.S. consumption of waxes and polishes equates to approxi-
mately 2.7 million pounds of the compound (Monsanto 1985b). It may also
function as a flame retardant and wetting agent in selected floor finishes
(We schl er 1980).
Tri(butoxyethyl) phosphate is also used as a softener in nitrile
rubber compounds to aid processing and increase low temperature flexibility
(Barnhart 1982). It has limited use as an antifoaming agent (SRI 1981-
1982). and has been approved for manufacture of paper and adhesives used in.
food packaging (FDA 1970. published in the FEDERAL REGISTER [35 F.R 5220]).
Tri(butoxyethyl) phosphate is a compatible plasticizer with the following:
cellulose acetate. cellulose nitrate. ethylcellulose. poly(methyl
methacrylate). poly(vinyl acetate). and poly(vinyl butyral) (Sears and
Touchette 1980). Tri(butoxyethyl) phosphate is also used as a model
displacer of drugs in studies of drug binding to blood plasma (Pike et ale
1981. as reported in Chem Abstr 96:45830u). Patents have been applied for
its use in the following: as a lubricating component for machining metal
(Hayashi et al 1984. as reported in Chem Abstr 102:28135w); and as a seal-
ing component (Toray Thiokol Co.. Ltd. 1983. as reported in Chem ~str
100: 211829y) .
4)
Poly-1 and poly-2
These poly-phosphates are possibly used as flow control additives in
ceramic glazes to help prevent migration of the glaze during firing of the
ceramic (Stout 1975). This potential use is suggested by a U.S. patent.
the only .reference to the chemical s found in searches of the DIALOG and
MEILARS II databases and in manual searches of secondary sources. It
should be noted. however. that the patent itse~f.does not mention the com-
pounds specifically.
d.
Worker Exposure
Very little information was found regarding worker exposure to
tri(alkyl/alkoxy) phosphates. At sites where the trialkyl phosphates are
manufactured. 3-4 workers/shift for 4 shifts/week may be iavolved in the
production of the chemicals throughout a given year (USEPA 1985). . The use
of closed processes. the blanket of nitrogen. local ventilation. appropri-
ate respiratory equipment. and protective clothing minimize worker exposure
during the actual reaction. However. after the reaction is completed.

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13
dermal exposure could occur during the connecting of the transfer lines
between the reactor and the drumming station and during the drumming or
. packaging of the finished produ~!. The very low vapor pressure values for
tr!~ethylhexyl) (v.p., 1.8 x 10 mm Hg) and tri(butoxyethyl) (v.p., 1.2 x
10 mm Hg) phosphates at room temperature make significant inhalation
exposure to these chemical s during the drumming operation unl ikely (USEPA
1985). .
The processing of the trialkyl phosphates mainly involves the mechani-
cal transfer of pure material, as received from the manufacturer, to a
blending operation .to produce polishes, plastic articles, or hydraulic
fluids (USEPA 1985). Incidental dermal exposure is possible, but not
likely, because the equipment is generally highly automated. Inhalation of
tributyl phosphate could occur during the packaging of hydraulic fluids
containing the ester.
The industrial use of the phosphate esters that probably has the
highest potential for worker exposure via dermal contact is in aircraft
maintenance involving the routine filling/draining. of hydraulic fluids,
which is a manual operation (USEPA 1985). The inhalation of tributyl phos-
phate vapors could also occur here. In ore extraction and plastics fabri-
cation, less exposure is expected due to the use of automated procedures
(USEPA 1985). The number of processing and use sites and the number of
workers potentially exposed during these activities is not known (USEPA
1985) .
Tributyl phosphate, commonly used as an extractant in the dissolution
process in conventional nuclear fuel reprocessing plants, can be released
to the off-gas stream under certain conditions (Parker 1980). This
release, which occurs when recycled acid is used in the dissolution process
(causing a build up of tributyl phosphate), could result in worker expo-
sure. An industrial hygiene report from Los Alamos Scientific Laboratory
indicates that irritating fumes may form when tributyl phosphate is heated,
necessitating ventilation of the work area (Hyatt and Milligan 1953).
Tributyl phosphate isomers were detected by gas chromatography-mass
spectrometry as impurities in the pesticide grade solvent, cyclohexane, at
levels of 0.89 and 2.9 ng/mL (Bowers .et a!. 1981). This grade of cyclohex-
ane is commonly used in gas chromatographic analytical procedures for
detecting trace levels of organic compounds in environmental samples.
Workers who perform these analyses could be exposed to small amounts of
tributyl phosphate.
No information or estimates of worker exposure were. available on poly-
1 and poly-2.
2.
Consumer Exposure
An abstract of a Russian article indicates that tributyl phosphate is
released into the a~omsphere from floor coverings made from poly(vinyl

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14
chloride) used in housing (Antonyuk 1973. as reported in Chem Abstr
8 0 : 30315 a) .
A patent has been issued for a coSmetic oil that contains ascorbic
acid fatty esters (70.) and trialkyl phosphates (30.) (Takemoto and Otani
1980. as reported in Chem Abstr 93:79878u). The trialkyl phosphates sug-
gested for use in this formulation included tributyl phosphate and
tri(ethylhexyl) phosphate. This indicates the potential for direct consu-
mer exposure to these phosphates; however. evidence for the commercial use
of such oils was not found.
Tri(ethylhexyl) phosphate at concentrations ranging from 60-200 ~g/mL
were detected in human blood stored for 2-6 months in a certain brand of
commonly used evacuated collection tubes (Missen and Dickson 1974). The
contamination was attributed to the leaching of the plasticizer from the
rubber stoppers of the tubes. The presence of tri(ethylhexyl) phosphate in
the blood interferes with the gas chromatographic anaylsis of blood for a
variety of drugs (Missen and Dickson 1974. Dusci and Hackett 1976).
Tri(butoxyethyl) phosphate and tri(ethylhexyl) phosphate were detected
among 13 other pollutants in aerosol collected from a six-story building
housing approximately 4000 employees in Holmdel. N1 (Weschler 1980). The
samples were collected on the sixth floor. In the building. a central air
handling system removes most outdoor particles larger than 2~ in diameter
and about 10. make-up outside air is added to the recirculated air. Con-
centrations of the organics were not reported. Tri(butoxyethyl) phosphate
was a component of the floor polish (-1~ by weight) used every 3 months in
the building. The phosphate was apparently introduced into the aerosol
during the routine stripping and buffing operations. and this was thought
to be the sole source of the compound. The source of the tri(ethylhexyl)
phosphate could not be determined.
In a later study. Weschler (1984) again identified tri(butoxyethyl)
phosphate and tri(ethylhexyl) phosphate associated with indoor airborne
particles in two office buildings. one in Lubbock. Texas. and one in
Wichita. KaJ.s~s. The average concenlr~tions of tri(butoxyethyl) phosphate
were 4 ng/m 1n Witchitaand 2S ng/m 1J Lubbock; the average concentration
of tri(ethylhexyl) phosphate was 6 ng/m for the Wichita location only. .
These compounds were not detected in the outdoor air samples. The organic
compounds .associated with indoor samples from the two locations were nearly
identical. indicating .similar source sat each location. JrHbutoxyethyl)
phosphate was detected in highest concentration (-25 ng/m ) immediately
after night crews had polished the floors.
Tri(butoxyethyl) phosphate has also been detected in the water-soluble
portion of smoke condensate collected from non filtered cigarettes smoked
under standard condi tions (Schumacher et a!. 1977).'
No information or estimates were available on consumer exposure of
poly-1 and poly-2.

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15
3.
Environmental Exposure
a.
Environmental Release
During production, trialkyl phosphates may be released to surface
waters in the decanting of the water used in the washing procedure (USEPA
1985). Small amounts of the phosphates could a150 be lost in distillation
bottoms and would subsequently be incinerated or landfilled.
. During processing of the esters, losses should be minimal (USEPA
1985). The only significant release to water may occur during the cleaning
of equipment used in formulating aqueous-based polishes.
During the industrial use of the triphosphates, some release could
occur during or~ extraction. The presence of tributyl and tri(butoxyethyl)
phosphates in industrial effluents (Shackelford et al. 1983) (Table 5) sug-
gests that these compounds may be released, eventually, into the aquatic
environment. There are usually no direct releases of the phosphates from
the materials into which they are incorporated (USEPA 1985).
Tributyl phosphate has also been found in a diverse number of smaller
surveys. Ellis et al. (1982) found tributyl phosphate in effluents from
three of the ten municipal secondary treatment facilities tested. Waggot
(1981) identified tributyl phosphate in concentrations usually less than
0.1 ~g/L and trimethyl phosphate in concentrations usually greater than 0.1
~g/L in sewage works discharges along the River Lee, North London, United
Kingdom. Tributyl phosphate was found in leachate from low-level radioac-
tive waste disposal sites in Maxey Flats, Kentucky, and West Valley, New
York, in concentrations ranging from 0.16 to 0.86 mg/L (Francis et al.
.1980b). Dunlap et al. (1975) identified tributyl phosphate in groundwater
underlying a landfill in Norman, Oklahoma. This compound was also deter-
mined in sludge from a wastewater management system receiving 7~ of its
influent from industrial sources (Demirjian et al. 1984). Schou et al.
(1981) found tributyl phosphate at a concentration of 0.9 ~g/L in an
effluent from a plant producing glue, paints, and wax resins in Norway. The
. effluent had undergone activated sludge treatment.
No information or estimates were available on environmental releases
of poly-1 and poly-2.
b.
Environmental Fate
There is little information on the various aspects of environmental
fate of the subject tri(alkyl/alkoxy) phospha~es. To round out these
topics, some information on trimethyl phosphate and tri(isobutyl) phosphate
is given. No information or estimates were available on poly-1 and poly-2.

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16
  Table 5. Alkyl/alkoxy phosphates in Aquatic Environmental Samplesa 
Compound Fr eq ue ncy Range Mean Source 
    (llg/L) (llg/L)   
 TBP 7 60.71 - 10029.50 1879.66 Paint' ink  
 TBP 6 6.86 - 500.21 55.75 Printing, publishing 
 TBP 3 149.00 - 13516.71 303 .50 Organics " plastics 
 TBP 9 6.62 - 299.93 146.23 Pulp, paper  
 TBP 2 53.80 - 143.48 98.64 Pha rmace ut i cal s 
 TBP 2 36.76 - 86.76 61. 76 Explosives  
 TBP 2 71.22 - 79.10 75.16 Foundries  
 TBP 1 222.18  222.18 Aluminum  
 TBP 1 762.30 762.30 Electronics  
 TBP 20 11.54 - 311.28 55.57 Organic chemicals 
 TBP 1 33.20  33.20 Transportation equipment 
 'mP 5 10.13 - 36.43 14.79 Publicly owned treatment works
 TBEP 1 7.32  7.32 Leather tanning 
 'mEP 1 1607.12 1607.12 Printing aDd publishing 
 'mEP 3 7.31 - 37.46 28.18 Rubber processing 
 TBEP 1 38.43  38.43 Mechanic~l products 
 'mEP 1 14.64  14 . 64 Transportation equipment 
 TBEP 42 0.97 - 269.62 7.52 Publ ic1y owned treatment works
a   et a1. 1983     
 Shackelford     
b         
 TBP = tributyl phosphate     
 TBEP = triCbutoxyethyl) phosphate    

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17
i.
Persi stence
(a)
Biode grada tion
In river die-away studies. Saeger et al. (1979) observed complete pri-
mary degradation of tributyl phosphate in less than seven days. They
recorded a similar trend in semicontinuous activated sludge studies that
qualitatively simulate secondary sewage treatment. At a feed rate of 3
mglL per 24 hours for tributyl phosphate. more than 96~ was biodegraded
during a 13 week test. At the same feed rate. approximately 20. of
tri(ethylhexyl) phosphate was biodegraded over a 34 week period. At a feed
rate of 13 mglL per 24 hour for tributyl phosphate. 56~ was biodegraded
over a 21 week test. In addition. CO2 evolution was measured and compared
to theoretical 'yield if the molecule were completely degraded. Results
differed between two tests in which initial tributyl phosphate concentra-
tions we're 20.0 and 19.4 mg/L. respectively. In the former. 0.9" of the
theoretical CO2 production occurred by test day 7. while 3.3~ occurred by
day 28. In the ,latter test. 30.4" occurred by day 7 and 90.8" by day 28.
The authors suggested that a difference in the ratio of tributyl phosphate
concentrationlactive biomass may have affected the results. They saw no
evidence of nonbiological degradation in sterile water controls. From
their st,udies with tributyl phosphate and 10 other trialkyl. alkyl aryl;
and triaryl phosphate esters. Saeger et al. concluded that phosphate esters
readily undergo primary and ultimate biodegradation by microbial popula-
tions that occur naturally in the aquatic environment. and that the shorter
the alkyl chain. the more biodegradable the ester;
Hattori et al (1981. as reported in Chem Abstr 96:91393b) found that
degradation rates for phosphate esters are faster in polluted seawater than
in clean seawater and were similar to rates in river water. Tributyl phos-
phate degraded more slowly than some of the phenyl esters but more rapidly
than esters possessing longer alkyl chains.
Francis et al. (1980a) examined anaerobic degradation of tributyl
phosphate present in trench leachates from a low-level radioactive disposal
sit~ in Maxey Flats, Kentucky. A mixed cuI tureof bacteria isolated from
the trenches failed to reduce the initial concentration of tributyl phos-
phate (0.24 mg/L) after 30 days of incubation at 28°C. In another report,
tributyl phosphate at an initial 'concentration of 0.7 mglL was reduced 13~
after aerobic incubation with trench leachate bacteria (Francis 1980).
Dick and Tabatabai (1978) studied the hydrolysis of organic and inor-
ganic phosphorus compounds added to soil at a rate of 500 ppm phosphorus
and incubated for 20°C under aerobic and waterlogged conditions. Rates of
hydrolysis were somewhat faster under aerobic conditions. Within seven
days, 30-98~ of the organic phosphates hydrolyzed.
(b)
Photodegradation
In discussing environmental transformation of simple trialkyl phos-
phates in the atmosphere, Radding et al. (1977) stated that direct photo-
chemical processes are probably not important.

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18
(c)
Hydrolysi s
Trialkyl phosphates hydrolyze in water by a bimolecular process
invol ving nucl eophil ic attack at the phosphorus '(Vernon 1957. as reported
in Penman and Osborne 1976). Wolfe (1980) estimated hydrolytic stability
using 1 inear free energy rel ationships. He cone! uded that acid-ca tafyzed
hydrolysis is too slow to be 'of environmental significance and that tri-
alkyl phosphate esters undergo alkaline hydrolysis very s~owly at most
environmental pH's.
BarnaEd et al. (1955) discussed the hydrolysis of trimethyl phosphate
that. in the presence of sodium hydroxide. yields second order kinetics and
occurs by the breaking of the oxygen-phosphorus bond. Dimethyl phosphate is
formed and is stable in alkaline solution at 35°C. In neutral or 'acidsolu-
tion. the dimethyl phosphate undergoes further hydrolysis. At 25°C and pH
7. the rate constant for the hydrolysis of trimethyl phosphate is 1.8 x 10-8
and the hydrolytic half-life is 1.2 years (Mabey and Mill 1978).
In a discussion of the esters of organic phosphorus compounds. Sand-
meyer and Kinin (1981) generalized that the stability of hydrolysis
increases with increasing degree of oxygenation and esterification. there-
fore. acidic mono- and diesters hydrolyze more readily than
tri(alkyl/alkoxy) phosphates. .
Coincidental with a series of toxicity assays. Newell et ale (1976)
determined that trimethyl phosphate was acceptably stable in drinking water
for at least five days.
(d)
Other routes of degradation
Zoetman et al. (1981) estimated a half-life of 0.1 years for
tri(isobutyl) phosphate in groundwater. Zyabborova and Teplyakova (1969)
indicated that formation of inorganic phosphorus from tributyl phosphate in
simulated bodies of water is sluggish. At test. concentrations of 10 and 50
mg/L. inorganic phosphorus did not appear until the 20th day. The route of
degradation is not clear in either study.
The estimated ratr of oxidation of trimethyl phosphate by HO radical
is <0.1 x 10-9 (M-l s- ); the half-,1ife for trimethyl phosphate degraded by
this route is )230 hours (Radding et al. 1977).
(e)
Bioaccumul a ti on
Octanol/water partition coefficients have been used to predict bioac-
cumulation. Sasaki et al. (1981) experimentally determined octanol/water
partition coefficients for tributyl phosphate of 9720 (log P = 3.99). They
determined bioconcentration ratios for killifish aDd goldfish exposed to 4
ppm tributyl phosphate of 30-35 aDd 6-11 respectively. The difference in
bioconcentration ratio may be caused by the differences in metaDolic
behavior of the toxicant in the two species. Killifish appear to more
actively absorb and metabolize tributyl phosphate. Sasaki et al. (1982)
observed bioconcentration ratios of 21-35 for killifish exposed to tributyl
phosphate in a continuous flow system. Uptake was rapid and fish attained

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19
a steady-state .concentration within one day. They concluded that concen-
tration ratios are independent of exposure concentration and test type
(static or flow through systems). .
Saeger et al. (1979) reported octanol/water partition coefficients for
commercial preparations of triCethylhexyl) phosphate of 16,800 (log P =
4.23) and tributyl phosphate of 10,100 (log P = 4.0). They calculated
bioconcentration factors of 250 for tri(ethylhexyl) phosphate and 190. for
tributyl phosphate, based on the octanol/water partition coefficient, and
concluded that phosphate esters have a moderate potential to.bioaccumulate.
Additional evidence of bioaccumulation was presented by LeBel and Wil-
liams (1983b) who developed a method for determining trialkyl phosphates in
human adipose tissue. -The method was inadequate for the separation of
tri(ethylhexyl) phosphate. Tributyl phosphate (9.0 ng/g extracted fat) was
measured in one of nine samples of human fat tissne. Tri(butoxyethyl)
phosphate was detected in four of twelve samples at concentrations ranging
from 4.0 to 26.8 ng/g. The fat tissue was obtained at autopsy and had been
frozen at -20°C but no information regarding the history of the sample was
given; however, the study was conducted in Ottawa, Canada.
ii. Transport
(a)
Air
Tributyl phosphate has been reported in precipitation in Norway after
having been transported in defined air masses with global trajectories
(Lunde et al. 1977).
(b)
Water
No data were found.
(c)
Soil
Tributyl phosphate migrates into ground water by dissolving in water
passing through landfill. sites. Reinhard et a1. (1984) examined a leachate
plume under a landfill in Waterloo, Ontario. No tribntyl phosphate was.
detected in a background sample outside the leaohate plume. Concentra~ions
of 1.2 J1g1L and 0.4 J1g/L were found, respectively, in the middle and near
the bo~dary of the plUme. The reduction in concentration with distance
from the landfill indicates some effectiveness of attenuating factors such
as dilution, biodegradation, and sorption. Tributyl phosphate has also
been detected in leachates from low-level radioactive waste disposal sites
(Francis et al. 1980b) and these are discussed further under Section
I.C.3.e, Environmental Occnrrence.
(d)
Biota
Octanol/water partition coefficients and bioconcentration data for
trimethyl phosphate, tri(ethylhexyl) phosphate, and tributyl phosphate (see
se~tion I.C.3.b, Environmental Fate, Bioaccumulation) suggest that the com-

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20
pounds have moderate to high potential to bioaccumulate and therefore may
undergo environmental transport in biota to some extent.
c.
Environmental Occurrence
Several monitoring studies have documented the presence of tributyl
phosphate and tri(butoxyethyl) phosphate in drinking water. suggesting that
these compounds may be present in the sources of the potable water sup-
plies. One study also reported an occurrence of tri(ethylhexyl) phosphate.
Tributyl phosphate has been found in finished drinking water in a
number of locations in the U.S. (Shackelford and Keith,1976). Millington
et al. (1983) analyzed organics adsorbed by granular activated carbon (GAC)
during treatment of water for an unidentified urban location in the U.S.
and found tribu~yl and tri(butoxyethyl) phosphates in extracts of the GAC
filter. Sulfet et al. (1980) identified tributyl phosphate in two of three
samples of finished drinking water processed from Schuykill River (near
Philadelphia) during 1975-76. and in seven of eight samples of finished
water. taken during 1975-1977. from a treatment plant using the Delaware'
River as its water source. Hites et al. (1979) studied the Delaware River
because it is a maj or source of drinking water and the incidence of cancer
is high in areas adj acent to it. Concentrations of tri(butoxyethyl) phos-
phate were 0.3-3 ppb for winter and 0.4-2 ppb for summer.
Williams et al. (1982) reported concentrations of tributyl phosphate
and tri(butoxyethyl) phosphate in finished drinking water for Canadian mun-
icipalities that obtain raw water from the Great Lakes. Tributyl phosphate
varied among locations and sources from 0.8 to 29.5 ng/L. Tri(butoxyethyl)
phosphate ranged from 1.6 to 271.6 ng/L. The apparent increase in tributyl
phosphate levels extended through the lake system from Lake Superior to
Lake Ontario.
LeBel et al. (1981) identified trialkyl phosphates in water produced
by six eastern Ontario water treatment plants during 1978. Valu~s among
the treatment plants varied from 0.5 to 11.8 nglL for tributyl phosphate.
Tri(butoxyethyl) phosphate varied from 0.9 to 75.4 nglL among the plants. ,
Tri(ethylhexyl) phosphate was only reported for one location with a concen-
tration of 0.3 ng/L. The authors reported a concentration of 6 ~g/L for
tri(butoxyethyl) phosphate in water that had been standing in the pipes and
200 nglL for samples obtained after flushing about 30 L through the pipes.
, O-rings and a rubber seal in the tap were the source of some of this phos-
phate and a potential source 'of error in reporting concentrations of
tri(butoxyethyl) phosphate.
Later work by LeBel and Williams (1983a) confirmed the observation of
increased levels of tri(butoxyethyl) phosphate in tap water that had been
standing in the pipes. The investigators measured concentrations of
tri(butoxyethyl) phosphate ranging from 11.8-34.9 nglL for first grab water
samples of domestic taps in Ontario. Canada. after non-use of the tap for
16 hours. Flushing the domestic taps with 60 L of water prior to taking a
sample resul ted in levels of tri(butoxyethyl) phosphate (lLO to 16.3 ng/L)
comparable to those found in raw water at the treatment plant and treated
water at a pumping station in the distribution system. LeBel and Williams

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21
(1983a), a1 so detected level s as high as 5400 nglL for a first draw sample'
of a laboratory tap that had not been used for 65 hours. They cited a sur-
vey (Environmental Health Directorate 1982, as reported in LeBel and Willi-
ams 1983a) indicating that ,17~ of Canadian consumers seldom or never flush
taps before drawing water for drinking or food preparation. '
Williams and LeBel (1981) reported concentrations of tributyl phos-
phate from municipal sources across Canada ranging from 0.2 to 62 nglL and
concentrations for tri(butoxyethyl) phosphate of 1.1-560 ng/L., The fin-
ished water contained higher levels of phosphates when water was obtained
from a river rather than from a lake. Groundwater sources usually gave the
lowest concentration. The highest concentrations of phosphates in finished
water were observed in St. Lawrence, Great Lakes, and Lake Winnipeg'
drainage basins with values ranging from 5.8 to 8.4 nglL for tributyl and
120 to 130 nglL for tri(butoxyethyl) phosphates. The Colum~ia, Pacific
Seaboard, and Atlantic Seaboard drainage basins showed the lowest values
with concentrations of tributyl phosphate ranging from 0.3-0.7 nglL and
tri(butoxyethyl) phosphate ranging from 32 to 84 ng/L. The authors could
not fully discount rubber seals and gaskets to which water was exposed dur-
ing treatment as a source of some of the tri(butoxyethyl) phosphate.
Tri(butoxyethyl) phosphate (a t level s of 4.0 to 26.8 ng/g)" was found
in 4 of 16 samples of human adipose tissue examined for the presence of
certain organic phosphatetriesters; tributyl phosphate (9.0 ng/g) was
found in one sample. These levels were calculated on the basis of
extracted fat (leBel and Williams 1983b).
Piet and Morra (1979) reported a maximum concentration of 30 nglL for
tributyl phosphate in tap water processed by bank filtration of water from
the Rhine River in th~ Netherlands. Piet et al. (1981) identified tributyl
phosphate (100 ng/L) in drinking water processed from surface water using
bank infiltration. This compound was not detected in water, before infiltra-
tion. Schou et al. (1981) detected 100 nglL for tributyl phosphate down-
s~ream from a plant producing glues, paints, and wax resins on the River
Nitelia in Norway. Concentrations of tri(butoxyethyl) phosphate were 0.3-3
ppb for winter and 0.4-2 ppb for summer. Zoetman et al. (1981) found a
maximum concentrat~on of 300 nglL for tributyl phosphate in contaminated
groundwaters in the Netherlands. Dunlap et al. (1975) estimated a concen-
tration of 1700 nglL for tributyl phosphate in groundwater Under a land-
fill. Due to quantitative inadequacies in their procedures, they con-
sidered this value to be a minimum (Dunlap et al. 1975). Grob and Grob
(1974) determined the concentrations of organic compounds in Lake Zurich,
spring, ground, and tap waters during October, 1973. Drinking water in
Zurich, Switzerland comes from this mix of sources with Lake Zurich being
the primary source. Tributyl phosphate occurred in concentrations of 82
nglL at the lake surface, S4 nglL at 30 m, 10 nglL in ground water, and 14
nglL in tap water. It was not detected in spring water. Zurcher and Geiger
(1976) found tributyl phosphate in the River Glatt in Switzerland during
May, 1975, but it was not among the compounds found in greatest quantity.
Shinohara et al. (1981) detected 7.8 parts per billion for tributyl
phosphate in tap water in,Kitakyushi, Japan. Keumochi et al. (1981, as
reported in Chem Abstr 99: 68978z) identified several organophosphates,

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22
including tri(butoxyethyl) phosphate, in river.waters, sewage sludge and
fish «0.005-0.019 mg/kg) from Okayama Prefecture, Japan.
Seasonal comparisons of concentrations are few. leBel et ale (1981)
reported values for tributyl and tri(butoxyethyl) phosphates that did not
vary appreciably between summer and winter samples. Hites e~ al. (1979)
noted higher concentrations for many organics, including tributyl phos-
phate, in winter. They suggested reduced efficiency of waste treatment
systems because of the colder temperatures and the presence of much surface
water runoff resulting in high levels of suspended organic matter that
adsorb organics as possible causes of this difference between summer and
winter concentrations.
Alkyl phosphates have also been identified in trench leachates from
waste di~posal sites, precipitation, and indoor air. Lunde et ale (1977)
reported tributyl phosphate in the water fraction of precipitation from
southern Norway. . Weschler (1984) found trHbutoxyethyl) and trj(ethyl-
hexyl) phosphate.s at average concentrations ranging from 4 ng/m to 2S
ng/m associated with indoor air particles. He did not find the compounds
in outdoor air. Kenmochi et al (1981, as reported in Chem Abstr 99:68978z)
identified trace amounts of tri(butoxyethyl) phosphate in atmospheric aero- .
sols in ~he Okayama Prefecture, Japan. .
No information or estimates were available on the environmental
occurrence of poly-l and poly-2.
D.
Heal th Effect s
(While the previous sections on Chemical Identity, Physical and Chemical
Properties, and Exposure are restricted to five selected tri(alkyl/alkoxy)
phosphates, this section includes information on other compounds in this
class as appropriate.)
1.
Metabol ism
a.
Absorption
The lethality data in Table 6 indicate that tri(alkyl/alkoxy) phos-
phates may b~ absorbed following dermal, oral, or respiratory exposure.
However, the low vapor pressure values of the class of compounds, in gen-
eral, indicate that inhalation exposure would not.be significant under nor-
mal conditions (Sandmeyer and Kirwin 1981).

Marzulli et al. (1965), demonstrated that 32p- and 14C-labeled
phosphorus-containing compounds can penetrate sheets of human stratum cor-
neum conjunctum in diffusion cells. From in vitro measurements of steady
state rates of penetration, the investigators were able to predict in vivo
skin penetration rates for phosphoric acid and a group of related phosphate
esters. With tri-n~butyl phosphate, this in vitro. model gave essentially
the same results as tests on anterior forearms of three human subjects.

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 Table 6. Lethality of Tri(altyl/altoxy) Phosphates in Esperimental Animals  
Pholphate Speoiea Route' Parameter Ooae (.l/tl) Reference   
    LDSO  2,004a   b 
Tri.ethyl Rat Oral  Deichmann and litherup 1946 
(512-S6-1) Rat Oral LDSO  1,110 Verachoyle and Cabral 1982 
 Rat Oral LDSO  840 Su 1984   
 Rat Oral  0 Faaaett 1963   
 LDSO  -I,6S0d   
 Rat 01'81 LDSO  3,390 Smyth et al. 1969  
 Rat Ipe ~~odied 800 Su 1984 1972f  
 Rat Ipe 1,000 Dean and Thorpe  
   Ipe by day 7   1972 f  
 Rat 4/8 died 2,000 Dean and Thorpe  
    by day 7     
 Mouao Oral LD  3,610 Newoll et a1. 1976  
 Mouao Oral LOSO  1,470 Su 1984'  1946b 
 Guinea Pil Oral LDSO  1,1421 DoichmanD and litherup 
 Guinea PiS Oral ~O  940 Su 1984   
 Guinea PiS Oral LDo  <1,40?: Fassott 1963  1946b 
 Rabbi t Oral LDSO  1,27S Oeich.ann and Witherup 
 Rabbi t Oral LDSO  1,0SOd Su 1984   
 Rabbit 001'llal LDSO  3,388 Smyth et al. 1969  
    SO     b 
Tributy I Rat 'Oral LDSO  3,000 Smyth, and Carpentor 1944 N
 eN
(126-73-8) . Rat 01'81 LDSO  1,400 lohannsen et al. 1977  
 Rat 01'81 LDSO  1,200 Roh. and Daas 1985  
 Rat (II) Oral LD  1,390 Mitomo et al. 1980  
 Ra t (f) Oral LDSO  I,S30 MItOllo ot al. 1980  
 Rat 01'81 LDSO  <20,000 DC 1985 a   
 Rat Ipe LDSO  800-1,6000 FUle tt 1963   
 Rat Ipo LOSO (96 h) SOO-I,OOO Oayo aDd Lidman 1978  
 Rat tom 0  LOSO  1,400 Teplyatoya 1968   
 Rat IVe LDSO  100 3 MEDLARS II (RYECS) 1985  
 Rat Inhal . L~~  -28,000 .1/. . FMC 1985 a   
 Mouae (.) Oral LDSO  1,240 MitOllo et a1. 1980 .  
 Mouso (f) 01'81 LD  900 Mitomo ot al. 1980  
 Mouae Ipo LDSO  63 MEm.ARS II (RDCS) 1985  
 Moulo tom 0  LOLo  1,200 Zyabbarova and Teplyakoya 1968 
 Guinea pll tom 0  2/iOdeatha 973/d s 4 dl FaSlett 1963 .   
 Rabbit Oe I'll al  LDSO  )3,100 10haDDsen et al. 1977  
 Rabbit Oormalt LD  >10,000 Rohm and Daas 1985  
 Rabbit Dermal LOS 0   >10,000 DC 1985 a   
 SO    

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Phosphate
  Table 6. continued   
Spec Ie s Routo Parametor DosoCmg/kg) Roforenco  
Rat Oral LDSO 3,200-6,400c Fassott 1963  
Rat Ipo LDSO 800-1,600c Fassott 1963  
Rat Oral LDiO 37,080 Doichmann and Gorard 1969b 
Rat Oral 21 deaths 36,800 MacFarland and Punte 1966 
Rat Ipo LDS9 0 Fassott 1963  
-30,0003  
Rat Inhal. No eaths 447 mg/m MacFarland and Punto 1966 
    for 210 min   
Mouso Oral LD >12,800c Fassett 1963  
Mouso Ipo LDSO 3,200-6,4000 Fassott 1963  
Rabbit Oral LDSO 46,000j MacFarland and Punte 1966b 
Rabb i t Donal LDSO -18,520 Doichmann and Gerard 1969 
Rabbit IVo 2/iOdeaths 3S8 MacFa~land and Punte 1966 
Rabbi t ITro 1/6 deaths 690 MacFarland and Punte 1966 
Rabbit ITro 1/6 deaths 1,810 3 MacFarland and Punte 1966 
Guinea pia Inhal. 6/10 deaths 283 maIm MaoFarland and Punte 1966 
    for 180 min   
Rat Oral LDSO 3,000 MEDLARS II CR'mCS) 1985 
Rat Oral LDSO 4,700 Monsanto 1985 a  
Rat Donal LD >S,OOO Monsanto 198.5a  N
MoulO IVo LDSO 180 -DLARS II CR'mCS) 1985 ~
Guinea Pia Oral LDSO 3,000 IIBDLARS II CR'mCS) 198.5 
SO 
Mouso Ipo LD.50 2.50-.5000 Fa..e tt 1963  
Mouso IVe LD.50 710 Fa..ett 1963  
Mouse Ive LD.50 320 IIBDLARS II CR'mCS) 198.5 
TriC isobutyl)
(126-71-6)

TriCe thyl huyl)
C78-42-2)
TriCbutoxyethyl)
C78-51-3)
TriaUyl
(1623-19-4 )

Tetrahydro-
ruaamethanol
(10421-00-6) .
a
bCaloelated, based on LD.50 of 1.65 .t/kS and density
As reportod -in Sandmeyer and Kirwin 1981
o
dReported by Fassett (1963) as -8L or-g/ks-
oCaloulated, based on LDSO of 2.83 mL/kl and density
IP .. Intraperitoneal in.J eoHon .
IV .. Intravenous inj eotion
fNO .. Not liven
As reported in Conner 1979
:Calou18ted, based on LD.50 of
iCalculated, based on LDSO of
jCaloulated, based on LDSO or
kCaloulated, basod on LDSO of
Abraidod and intact akin
of 1.2144 lId. Ca t 20'C)
of 1.191 lId. Cat 19.5'C)
0.94 d./ts and density of 1.2144 I/mL Cat 20'C)
1.05 .t/tl and density of 1.2144 s/mL Cat 20'C)
1 mL/kS and density of 0.9727 I/mL Cst 25'C)
-20 .llkl and donsity of 0.9260 I/mL Cat 20'C)

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25
The penetration rates for (1) trimethyl, (2) triethyl, (3) tri(isopropyl),
(4) tri-n-propyl (5~ tributyl, and (6) tri-o-cresyl phosphates in terms of
JllDoles/cm2/min x 10 were as follows: (1) 1.047, (2) 0.623, (3) 0.350, (4)
0.288, (5) 0.067, and (6) 0.0007: The rate increased as solubilities in
water and benzene increased, and as molecular weight and boiling point
decreased. The skin penetration rate was also related to the benzene/water
distribution of the esters. In addition, it appeared that neutral
molecules pass easily through the skin while ionized forms do not.
b.
Di stribution
The distribution of tri(ethylhexyl) phosphate iJ rats was studied by
MacFarland and Punte (1966) following exposure to a 2P-labeled aerosol of
the compound (0.72-0.91 mg/L) for twenty minutes. The animals were sacri-
ficed at variou~ time intervals up to 70 hours. Most tissues had maximum
retention in the first few hou~s followed by a progressive decay. Peak
activity was observed earliest in the lungs (13~ retention) at five
minutes, followed by peak activities in the brain (9~) and liver (16~) at
30 minutes, and then in the stomach (50-64~) at one hour. The spleen, kid-
neys, bone, muscle, and fat never retained more than 2~ of the radioac-
tivity. Urinary and fecal excretions were 7~ at 17 hours (time of first
measurement), and then declined steadily~
c.
Biotransf ormation and Excretion.
Trialkvl nhosnhates
The same general metabolic patterns were observed by Jones (1970) for
triethyl phosphate, tri-n-butyl phosphate, tri-isopropyl phosphate, and
tri-n-propyl phosphate. He concluded that trialkyl phosphates are metabol-
ized to the corresponding dialkyl phosphates and the S-alkyl cysteines.
Jones further concluded that monodealkylation appears to be a common route
of metabolism for this class of compounds, most likely occuring through
enzymatic hydrolysis (P-O cleavage) and de-o-alkylation (C-O cleavage, with
reduced glutathione acting as a methyl receptor).
The transformation of a number of trialkyl phosphates to dialkyl phos-
phates and the corresponding S-alkyl-L-cysteines has. also been reported by
Jackson and Jones (1968) and Jones and Jackson (1969). In addition to the
dialkyl phosphates, Nomeir et al. (1981, as reported in NTP 1984) and
Nomeir and Matthews (1983, as reported in NTP 1984) identified monoalkyl
phosphates and the respective. al cohol s as important metabol i tes.
Biotransformation and excretion of specific tri(alkyl/alkoxy) phosphates
are described below.
Trimethvl nhosnhate
Jones (1970) concentrated his studies on the metabolism of trialkyl
~~osphates in mice and rats on that of trimethyl phosphate, administering
P-trimethyl phosphate orally (100 mg/kg)3~r intraperitoneally (1 g/kg) to
the animals. Chromatograms revealed that P-dimethyl phosphate was
excreted in the urine in both species. Unchanged trimethyl phosphate was
detected in trace amounts only in rat urine within 6 hours of

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26
intraperitoneal inj ection. SimilJ~lY. mouse bladders cannulated 1 hour.
after oral dosing contained only P-dimethyl phosphate. which was excreted
unchar!ed. with no production of monoalkyl phosphate or phosphoric acid.
When C-trimethyl phosphate was administered. two additional metabolites,
S-methyl cysteine and its N-acetate, were detected in the urine. indicating
that dealkylation occurs during detoxification.
Tributvl nhosnhate
,
The metabolism of tributyl phosphate has been studied in vivo
ing its intraperitoneal and oral administration to rats (Suzuki et
1984a. 1984b), and in vitro in rat liver homogenate (Sasaki et al.
f 011 ow-
a1.
1984 ) .
Eleven phosphorus-containing metabolites were identified in a 24-hour
urine sample from rats following intraperitoneal injection of 250 mg/kg of
the ester (Suzuki et al. 1984a). The major metabolites inciuded dibutyl
hydrogen phosphate. butyl dihydrogen phosphate. and butyl bis(3-hydroxy-
butyl) phosphate. Small amounts of derivatives hydroxylated at other car-
bons of the butyl groups were al so de teet ed. The maj or. metabol ic inter-
mediates were considered to be dibutyl 3-hydroxybutyl phosphate and dibutyl
3-oxobutyl phospha.te.
In a follow-up study to determine whether these metabolites are formed
by mixed-function oxidases. by esterases, or by glutathione S-transferase,
Suzuki et al. (1984b) identified sulfur-containing metabolites of tributyl
phosphate. The authors hoped to determine whether the butyl moieties are
removed intact or in an oxidized form. In this study (Suzuki et ale
1984b). the major urinary metabolites following a single intraperitoneal
injection of tributyl phosphate were (3-oxobutyl)- and (3-hydroxybutyl)-
mercapturic acid. Traces of 2-oxobutyl- and (2-hydroxybutyl)mercapturic
acids were al so de tected.
Sasaki et al. (1984) determined the in vitro metabolic pathway of tri-
butyl phosphate. using liver homogenate, as being first to tributylhydroxy-
phosphate and then to tributyl djhydroxyphosphate (with dibutyl phosphate
being only a minor dead-end point in the in vitro pathway). .

.. 14
Following a singl~ oral dose of C-tributyl phosphate (14 mg/kg) to
male rats, SO. 10. and 6% of the label were excreted in the urine. exhaled
air, and feces, respectively, within 24 hours (Suzuki et a1.. 1984a). Fol-
lowing a single intraperitoneal injection (14 mg/kg), 70, 7, and 4~ were
excreted in the urine. exhaled air, and feces. respectively. within 24
hour s.
Triallvl nhosnhate
Kaye and Young (1970) and Kaye (1973) studied the metabolism of trial-
lyl phosphate in the rat and found that. after intraperitoneal or subcu-
taneous injection, or oral intubation of the ester. the main metabolites
~etected in the urine sample collected during the next 24 hours were ally1-
mercapturic acid, allylmercapturic acid sulfoxide ~nd a hydroxypropylmer-
capturic acid. Similarly,. when triallyl phosphate was injected into rats,

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27
3.9~ of the administered compound was detected as allylmercapturic acid in
the urine within the first 24 hours (Kaye, and Young 1970).
2.
Le thal i ty
Acute lethality data for tria1ky1 phosphates are reported in Table 6.
The oral LD 0 values in the rat vary from 0.84 g/kg for trimethy1 phosphate
(Sax 1984) Ł0 37.08 g/kg for tri(ethylhexyl) phosphate (Deichman a~d Gerard
1969, as reported in Sandmeyer and Kirwin 1981). These values indicate
that, according to the scale of Gosselin et a1. (1984), the compounds are
generally of low to moderate 0~a1 toxicity.
Dean and Thorpe (1972, as reported in Conner 1979) reported that rats
given 5 oral doses of 500 mglkg of trimethyl phosphate survived, ,but that,
rats given 4 oral doses of 1000 mg/kg did not. Similarly, Vandekar (1957,
as reported in Conner 1979) reported that 1800 mglkg of trimethy1 phos-
phate, inj ected intravenously, was tolerated by rats, while 2400 mg/kg pro-
duced transient anesthesia and then death at 24 hours.
Smyth et a1. (1969) reported that rats could inhale concentrated
vapors of trimethy1 phosphate for 8 hours, maximum, with no deaths occur-
ring, 'and Fasset (1963) reported that rats could inhale 122 PlD of
tri(isobuty1) phDsphate for 6 hr with no deaths.
3.
Carcinogenici ty
a.
Type of Test:
Carcinogenicity of trimethy1 phosphate (NCI 1978)
Species:
Fischer 344 rats; SO rats of each sex per dose group,
20 rats of each sex for vehicle controls
Do se I Rout e :
0, SO, or 100 mg/kg of trimethyl phosph~te in distil-
led water by gavage 3 dayslweek for 104 weeks

Necropsies of all major tissues, organs, or gross
lesions were performed at the termination of the experi-
ment or at the death of the animal~ Kaplan and Meier
curves were. used to estimate probabilities of survival
and and' the Tarone test was used to determine positive
dose-related trends in survival. Statistical methods
used to analyze tumor incidences are briefly explained
in the footnotes to Tables 7 and 8.
Protocol:
Results:
Mean body weights of the treated rats were slightly
lower than those of the controls and the reductions in
weight were dose-related. No significant positive dose-
related trend in mortality was observed in either sex.
Sufficient numbers of rat~ survived to beat risk of
late-appearing tumors. The incidences of neoplastic and
nonneoplastic lesions are summarized in Tables 7'and 8
for males and females, respectively.

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28
Table 7.
Incidences of Lesions in Trimethyl Phosphate-Treated Male Ratsa
Type of Lesion
o mg/kg
50 mg/kg
100 mg/kg
Subcutaneous ti ssue    
Fibroma      
 Overall ra te sb  0/20(0WI) 2/50(4-.) 9/4908-.)
 Cochran-Armitage ~estC P=0.006  
 Fisher exact test   N. S. P=0.036
 Relative Riske   Inlini te Infinite
 Lower Limit    0.123 1. 119
 Upper Limit    Infinite Infinite
Lung       
Alveolar/bronciolar    
adenoma or carcinoma   
 Overall rates   0/19 (011) 2/49 (4..) 5/46(11..)
 Cochran-Armi tage test N. S.  
 Fisher exact test   N.S N. S.
 Rela U ve Risk    Inlini te Infinite
 Lower Limit    0.119 0.545
 Upper Limit    Inf in! te Inf inite
Hematopoietic system    
Leukemia or Lymphoma   
 Overall rates   8/20(40lIl) 20/50 (40lIl) 25/49(51111)
 Cochran-Armi tage test N. S.  
0 Fi sher exact test   N. S. N. S.
 Relative Risk    1.0 1.276
 Lower     0.529 0.703
 Upper     2.242 2.746
Pituitary      
Chromophobe Adenoma    
 Overall rate s   4/16(25,*,) 13/44 (30W1) 8/38 (21,*,) 
 Cochran-Armitage test N. S.  
 Fi sher exa ct test   N. S. N. S.
 ReI a ti ve Risk    1.182 0.842
 Lower Limit    0.450 0.276
 Upper Limit    4.430 3 . 4 06

-------
Ta bl e 7.
29
(Continued)
100 mg/kg
Type of Le si on
o mg/kg
50 mg/kg
Adrenal
Pheochromocytoma
Overall rate s
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limi t
Upper Limit
Thyroid
C-cell Adenoma or
Carcinoma
Overall rate s
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limit
Upper Limit
Te st i s
Interstitial-cell Tumor
Overall rate s
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limi t
Upper Limit
1/ 20( S'i) 4/48(8") 7/47(15..)
N. S.  
 N. S. N. S.
 1.667 2.979
 0.182 0.429
 80.315 131. 059
1/19 (5..) 3/45(7..) 2/46(4")
N. S.  
 N. S. N. S.
 1.267 0.826
 0.112 0.047
 64.997 47.694
11/16 (69..)
. N. S.
33/46(72CJb)
25/46 (54%)
N. S.
1.043
0.742
1. 722
N. S.
0.791
0.544
1. 393
a .
Source:
NCI 1978
bNumber of tumor-bearing animal s/number .of animal s examined
(percent)

'cThe Cochran-Armitage test identifies positive dose-related
trends in tumor incidence. The test is for significant posi-
tive trend with dose unless noted otherwise. Beneath the
control incidence are the P values associated with the trend
test; N. S. = not significant

-------
30
~e Fisher exact test was used to compare the incidence of
tumors in the dosed groups to those of the controls. Beneath
. the dosed groups incidence are the Pvalues corresponding to
the pairwise comparisons between that dosed group and the
controls. .
e The 9~ confidence interval of the relative risk between
each dosed group and the vehicle-control groups. Approxi-
matly 95% of a large number. of identical experiments should
be within the interval calculated from this experiment. No
significant difference in tumor incidence exists when the
lower limit is (1; but if the upper limit is >1. the theoret-
ical possibility exists for induction of a tumor. Differences
between control and dosed groups are statistically signifi-
cant if the lower limit is >1.

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31
Table 8.
Incidences of Lesions in Trimethyl Phosphate-Treated Female Rats&
Type of Lesion
100 mg/kg
o mg/kg
50 mg/kg
Lung
Alveolar/bronchiolar
adenoma or carcinoma
Overall ratesb
Cochran-Armitage ~estC
Fi sher exa ct test.
Relative Riske
Lower Limit
Upper Limit
Hematopoietic System
Lymphoma or Leukemia
Overall rates
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limi t
Upper Limi t
Pi tui ta ry
Chromophobe adenoma
Overall rate s
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limit
Uppe r Limi t
Thyroid
C-cell carcinoma
Overall rates
Cochran-~itage test
Fisher exact test
Departure from linearityf
Relative Risk
Lower Limi t
Upper Limit
0/20( 011)
N. S.
3/20( 1~)
N. S.
9/20(45...)
N. S.
2/ 19 (11...)
N. S.
P=0.044
0/ 50( 011)
N. S.
14/50(28...)
N. S.
1.867
0.609
9.359
21/48(44"')
N. S.
0.972
0.544
2.025
0/47(011)
N. S.
0.000
0.000
1. 3 57
3/45(7...)
N. S.
Infinite
0.278
Infinite
12/ 49 (24...)
N. S.
1.633
0.513
8.342
18/41(44...)
N. S.
0.976
0.532
2.049
2/ 43 (5...)
N. S.
0.442
0.035
5.796

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Ta bl e 8.
Type of Lesion
Thyroid (continued)
C-cell adenoma or
carcinoma
Overall rate s
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower 'Limi t
Upper Limit
Mammary gl and,
Fibroadenoma
Overall rates
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limit
Upper Limit
Uterus
Endometrial stromal
polyp
Overall rates
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limi t
Upper Limit
32
(Continued)
o mg/kg
50 mg/kg
100 mg/kg
5/43 (12-.)
N. S.
1.105
0.205
10.982
5/49 (1m.)
N. S.
1. 020
0.188
10.204
0/44(m.)
N. S.
0.000
0.000
1. 524
a '
-Source: NCI 1978
2/ 19 (11-.)
N. S.
6/47(13%)
b
Number of tumor-bearing animals/number of animals examined
(percent)

cThe Cochran-Armitage test identifies positive dose-related
trends in tumor incidence. The test is for significant posi-
tive trend with dose unless noted otherwise. Beneath the'
control incidence are the P values associated with the trend
test; N. S. = not significant
N. S.
1.213
0.247
11. 660
2/20(1m.)
N. S.
3/50(6,*,)
~e Fisher exact test was used to compare the incidence of
tumors in the dosed groups to those of ,the control s. Beneath
the dosed groups incidence are the P values corresponding to
N. S.
0.600
0.076
6.860
2/20(1m.)
P=0.043Ng
1/45("")
N. S.
O. 222
0.004
4.077

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33
.the pairwise comparisons between that dosed group and the
control s.
The 9S1W1 confidence interval of the relative risk between each
dosed group and the vehicle-control groups. Approximatly 9~
of a large number of identical experiments should be within
the interval calculated from this experiment. No' significant
difference in tumor incidence exists when the lower limit is
<1; but if the upper limit is >1, the theoretical possibility
exists for induction of a tumor. Differences between control
and dosed groups are statistically significant if the lower
fl imit is >1.
The Cochran-Armitage test also provides for a two-tailed test
of departure from linear trend.
gN =. negative trend, lower incidence in dosed group than in
control

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34
The authors concluded that. under the conditions of the
bioassay. trimethyl phosphate was associated with a dose-
related. statistically significant increase in the
incidence of benign sub~utaneous fibromas in male rats.
Female rats exposed to trimethyl phosphate did not exhi-
bi t signif icanUy increased incidence s of tumors.
b.
Type of Test: Carcinogenicity of

Species: B6C3F1 mice; SO mice of
20 mice of each sex for
each sex per dose group.
vehicle controls
trimethyl phosphate (NCI 1978)
Dose/Route:
O. 2S0. or SOO mg/kg of trimethyl phosphate in dis-
tilled water by gavage 3 days/week for 103 weeks

Necropsies of all major tissues. organs. or gross
lesions were performed at the termination of the experi-
ment or at the death of the animal. Kaplan and Meier
curves were used to estimate probabilities of survival
and the Tarone test was used to determine positive dose-
related trends in survival. Statistical methods used to
analyze tumor incidences are briefly explained in the
footnotes to Tables 9 and 10.
Protocol:
Re sul t s :
Mean body weights of female mice in the dosed groups were
lower than those of the controls and the reduction in
weight was dose-related. Mean body weights of the male
mice exposed to trimethyl phosphate were comparable to
those of the controls. A significant dose-related trend
in mortality was not observed in either sex. Sufficient
numbers of mice survived to detect late-appearing tumors.
Incidences of neoplastic and nonneoplastic tumors are
summarized in Tables 9 and 10 for male and female mice.
respectively.
Significant increase in the incidence of tumors in
male mice was not observed. In female mice. however.
there was a statistically significant higher incidence of
adenocarcinomas of the endometrium in the high-dose .
group. than in vehicle controls. and the trend ac~oss all
groups was also significantly dose-related. The uterine
adenocarcinomas were described as highly malignant with
vascular involvement and pulmonary metastases in one low-
dose and four high-dose mice. Metastases were more fre-
quent in the high-dose groups; hence the tumors appeared
more aggressive in these animals. Thus. under the condi-
tions of the bioassay. the authors concluded that
trimethyl phosphate was carcin~enic in female mice as
evidenced by the induction of adenocarcinomas of the
uterus/endometrium.

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35
Table 9.
Incidences of Lesions in Trimethyl Phosphate-Treated Male Micea
Type of Le si on
o mg/kg
50 mg/kg
100 mg/kg
Lung     
Alveolar/bronchiolar   
carcinoma     
Overall ratesb  2/20( l(J11) 8/50(16") 3/49 (6%)
Cochran-Armitage !estC N. S.  
Fisher exact test   N. S. N. S.
Rela tive Riske   1.600 0.612
Lower Limit   0.364 O. 078
Upper Limit   14.699 6.996
Alveolar/bronchiolar   
adenoma or carcinoma   
Overall rates  3/20(15%) 11/50(22%) 9/49 (18% )
Cochran-Armitage test N. S.  
Fi sher exact test   N. S. N. S.
ReI ative Risk   1.467 1.224
Lower Limit   0.450 0.354
Upper Limit   7.594 6.533
Bema topoi eti c System    
Lymphoma or Leukemia   
Overall rates  3/20(15%) 5/50(10%) 9/49(18%)
Cochran-Armi tage test N. S.  
Fisher exact test   N. S. N. S.
Relative Risk   0.667 1.224
Lower Limit   0.147 0.354
Upper Limit   4.014 6.53~
Liver     
Bepa tocellul ar    
carcinoma     
Overall rate s  4/20(2(J11) 9/48 ( 19%) 8/49(16")
Cochran-Armitage test N. S.  
Fisher exact test  N. S. N. S.
Relative Risk   0.938 0.816
Lower Limit   0.307 0.255
Upper Limit   3.804 3.392

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36
Ta bl e 9.
(Continued)
Type of Le si on
o mg/kg
50 mg/kg
100 mg/kg
Hepa tocellular
adenoma or carcinoma
Overall rates
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limit
Upper Limit
4/20(2OCL)
N. S.
10/48 (21..)
8/49 (16..)
N. S.
1.402
O. 3 53
4.148
N. S.
0.816
0.255
3.392
a
Source:
NC! 1978
b
Number of ttDDo~bearing animal s/ntDDber of animal s examoined
(percent)

cThe Cochran-Armitage test identifies positive dose-related
trends in tumor incidence. The test is for significant posi-
tive trend with dose unless noted otherwise. Beneath the
control incidence are the P values associated with the trend
test; N.S. = not significant
~e Fisher exact test was used to compare the incidence of
ttDDors in the dosed groups to those of the controls. Beneath
the dosed groups incidence are the P values corresponding to
the pairwise comparisons between that dosed group and the
control s. .
eThe 95.. conf idence interval of the rei a ti ve risk be tween each
dosed group and the vehicle-control groups. Approximatly 95..
of a large number of identical experiments should be within
the interval calculated from this experiment. No significant
difference in tumor incidence exists when the lower limit is
<1. but if the upper limit is >1 the theoretical possibility
exists for induction of a ttDDor. Differences between control
and dosed groups are statistically significant if the lower
I imit is > 1.

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37
Table 10.
Incidences of Lesions in Trimethyl Phosphate-Treated Female Micea
Type of Les~on
o mg/kg
50 mg/kg
100 mg/kg
Lung    
Alveolar/bronchiolar   
adenoma or carcinoma   
Overall rates  3/20(15'W1) 0/48(0.) 6/45 (13CW1)
Cochran-Armitage test N. S.  
Fisher exact test   P = 0.023(N)g N. S.
Departure from linearityf P = 0.008  
Rela tive Risk   0.000 0.889
Lower Limit   0.000 0.218
. Upper Limit   0.686 5.104
Hematopoietic. System    
Lymphoma or Leukemia   
Overall rates  5/20(25..) 14/50(28") 11/47(23..)
Cochra~Armitage test N. S.  
Fisher exact test   N. S. N.S.
Relative Risk   1.120 0.936
Lower Limi t   0.457 0.358
Upper Limit   3.556 3.080
Liver    
Hepa toce1lul ar    
adenoma or carcinoma   
Overall rates  2/ 20(10lIl) 4/50(8") 0/44 (011)
Cochran-Armitage test N. S.  
Fisher exact test   N. S. N. S.
Relative Risk   0.800 0.000
Lower Limit   0.128 0.000
Upper Limit   8.436 1. 524
Uterus/Endometrium    
Adenocarcinoma    
Overall rates  0/16( OWl) 7140(18..) 13/37 (35'W1)
Cochran-Armitage test P = 0.003  
Fi sher exact test   N. S. P = 0.004
Relative Risk   Inf ini te Inf inite
Lower. Limit   0.825 1.850
Upper Limit   .Inf ini te Inf inite

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38
Tabl e 10.
(Continued)
Type of Le si on
o mg/kg
SO mg/kg
100 mg/kg
Uterus:
Endometrium
Stromal polyp
Overall rates
Cochran-Armitage test
Fisher exact test
Relative Risk
Lower Limin
Upper Limit
'0/16 (011) 2/40( S") 1/37(3")
N. S;  
 N. S. N. S.
 Infinite Inf inite
 0.12S 0.024
 Infinite Infinite
a
Source:
NCI 1978
b
Number of tumor-bearing animals/number of animals examined
(percent)
c
The Cochran-Armitage test identifies positive dose-related
trends in tumor incidence. The test is for significant posi-
tive trend with dose unless noted otherwise. Beneath the
control incidence are the P values associated with the trend
test; N.S. = not significant

~e Fisher exact test was used to compare the incidence of
tumors in the dosed groups to those of the controls. Beneath
the dosed groups incidence are the P values corresponding to
the pairwise comparisons between that dosed group and the
control s.
eThe 9S" confidence interval of the relative risk between each
dosed group and the vehicle-control groups. Approximatly 9S"
of a large number of identical experiments shouid be within
the interval calculated from this experiment. No significant
difference in tumor incidence exists when the lower limit is
<1, but if the upper limit is >1 the theoretical possibility
fexists for induction of a tumor. Differences between control.
The Cochran-Armitage test also provides for a two-tailed test
of departure from linear trend.
gN = negative trend, lower incidence in dosed group than in
control

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39
c.
Carcinogenicity of tri(ethylhexyl) phosphate
(NTP 1984)

Species: F344/N rats, SO males and SO females/dose group

Dose/Route: Males - 0, 2,000, or 4,000 mg/kg of triethyl-
hexyl phosphate in corn oil by gavage

Females - 0, 1,000, or 2,000 mg/kg of triethyl-
hexyl phosphate in corn oil by gavage

All doses administered S days/week for 103 weeks
Type of Test:
Protocol:
Necropsies were performed on all animals and numerous
tissues were examined microscopically. Four methods of
statistical analysis of tumor incidence were employed:
the life table analysis, the incidental tumor analysis,
the Fisher's exact test, and the Cochran-Armitage linear
trend test. Brief descriptions of the tests are in the
footnotes of Table 11.

The mean bodY weights of treated males were
notably lower than those of the controls throughout the
study. The mean body weights of the high dosed females
were only s1 ightly lower than those of the .control s, and.
no compound-related clinical symptoms were noted. No
significant differences in survival were observed between
the treatment and control groups of males or females.
Results:
The data in Table 11 demonstrate compound-related
increases in the combined incidences of adrenal pheochro-
mocytomas and thyroid neoplasms in male rats. The
increase in the adrenal tumors was dose-related and sta-
tistically significant when compared to that of the con-
trols (P=0.026, low dose; P=0.004, high dose). However,
the incidence of these tumors in the vehicle controls of
this study was low (4~) when compared to that of the con-
trols in two previous studies (2") or with the histori-
cal incidence of. the tumor observed throughout the bioas~
say program (18~). For this reason, the induction of
adrenal pheochromocytomas was considered to be equivocal
evidence for the. carcinogenici ty of triCe thylhexyl) phos-
phate. The trend-wise increase in the incidence of thy-
roid neoplasms (combined) across all groups was signifi-
cantly dose-related, but pair-wise comprisons to vehicle
controls were not statistically significant.
The investigators concluded that under the conditions of
the study, there was" equivocal evidence of carcinogeni-
city" (as evidenced by adrenal' pheochromocytomas) in male
F344/N rats given 2,000 or 4,000 mg/kg tri(ethylhexyl)
phosphate, and "no evidence of carcinogenicity" in female
rats given 1,000 or 2,000 mg/kg of the compound;

-------
40
Tabl e 11.
Incidences of Lesions in Tri(ethylhexyl) Phosphate-Treated Rats
TYpe of Lesion (Sex)
High Dose
Adrenal Lesions (Males)

Adrenal/medulla hyperplasia
Overall rates
Pheochromocytoma
Overall ratesa
Adjusted ratesb
Terminal ra tesC
Life table testsd
Incidental tumor testsd
Corchran-Armitage trend
Fisher's exact test
testd
Thyroid Lesions (Males)

Follicular cell h„perplasia
Overall rates

'Foll icul ar cell ade nCID a,
cystaden(IDa, or
carcin(IDa
Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table testsd
Incidental tumor testsd
Corchran-Armitage trend testd
Fisher's exact test
Pa~creatic Lesions (Males)

Acinar cell h„perplasia
Overall rates
Acinar cell adenCIDa
Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table testsd
Incidental tumor testsd
Corchran-Armitage trend
Fisher's exact test
testd
Control
1/ 50( 2tJI)
2/50(4")
5.ocr.
2/40( ,.)
P=0.004
P=O.OOS
P=0.004
2.46 (4..)
1/46(24i) f,
2.6"
1/39 (3')
P=0.028
P=0.032
P=0.034
9/50(18..)
14/ 50( 28..)
35.0..
14/40( 3,")
P
-------
41
Tabl ell.
(continued)
Type of Lesion (Sex)
Control
Low Do se
High Dose
Mammary Gland Tumors (Females)
Overall ra te sa
Adjusted ratesb
Terminal ra tesC
Life table testsd
Incidental tumor testsd
Corchran-Armitage trend testd
Fi sher' s exa ct te st
11/50(2~)
28.8"
9/36(2S111)
P=0.248N
P=0.189N
P=0.152N
2.50(4")
5.4"
1/34 (3")
P=0.013N
P=O.OISN
7.50(14")
19 . 5"
3130(1~)
P=0.359N
P=0.308N
P=0.008N
P=0.218N
aNumber of tumor-bearing animals/number of animals examined at the site
b
Kaplan-Meier estimated tumor incidence at the end of the study after
adjusting for intercurrent mortality

cObserved tumor incidence at terminal kill

'1Jeneath the control incidence are the P values associated with the trend
test. Beneath the dosed group incidence are the P values corresponding to
pairwise comparisons between that dosed group and the controls. The life
table analysis regards tumors in animals dying prior to terminal kill as
being (directly or indirectly) the cause of death. The incidental tumor
test regards these lesions as nonfatal. The Cochran-Armitage and Fisher's
exact test compare directly the overall incidence rates. A negative trend
or lower incidence in a dosed group is indica ted by N.
e
Two other male rats had malignant pheochromocytomas.

fFollicular cell carconoma

gOne follicular cell adenoma or cystadenoma. one follicular cell carcinoma

~ree follicular cell adenomas or cystadenomas. three follicular cell
carcinomas
Source:
NTP (1984)

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42
d.
Type of Test:
Carcinogenicity of tri(ethylhexyl) phosphate
(NTP 1984)
Species: B6C3F1 mice. SO males and SO

Dose/Route: 0, 500. or 1,000 mg/kg of
in corn oil. administered
103 weeks.
females per group

tri(ethylhexyl) phosphate
by gavage'5 days/week for
Protocol:
Resul ts:
Necropsies were performed on all animals and numerous
tissues were examined microscopically. Four methods of
statistical analysis of tumor incidence were employed:
the life table analysis. the incidental tumor analysis.
the Fisher's exact test. and the Cochran-Armitage linear
trend test. Brief descriptions of the tests are in the
footnotes of Table 12.

Mean body weights for treated male and female mice were
within 10. of control weights all during the study; and
survival rates of the treated groups were not signifi-
I
cantly different. from those of the control groups. While
the trend-wise increase in the incidence of hepatocellu-
lar carcinomas across all groups was significantly dose-
related. pair-wise comparisons to vehicle controls.were
significantly higher only in the female high-dose group
(Table 12). A statistically significant increase for
these carcinomas in males was not observed. Thyroid fol-
licular cell hyperplasia was observed in both males and
females at increased incidences. and follicular cell
adenomas were seen in one. high-dose male and in two low
dose females. but not in the controls.
The investigators concluded that under the condi-
tions of this study. there is "some evidence of carcino-
genicity" (as evidenced by hepatocellular carcinomas) in
female mice treated with 1.000 mg/kg of tri(ethylhexyl) .
phosphate.
Driesbach (1983) classifies triallylphosphate as a carcinogen; how-
ever. no other information was found to conf irm this.
4.
Genotoxi city
a.
Mutagenicity
According to Lawley and Brookes (1963. as reported in Dean 1972)
alkylating agents such as trimethyl phosphate produce gene mutations mainly
through base substitution by alkylation of DNA bases (see section I.D.4.b).
The data in Table 13 demonstrate that trimethyl phosphate is mutagenic in
the Ames Salmonella reversion assay and in the~. Coli DNA repair test (De
Flora et ale 1984). This effect has been descr~bed as weak (De Flora 1981.
Dean 1972). Metabolic activation slightly increases the response in Sal-
monella (De Flora 1981). Trimethyl phosphate has also been described as a
"weak mutagen" in the mouse dominant lethal assay, in the. bone marrow

-------
43
T4bl e 12.
Incidences of Lesions in Tri(ethylhexyl) Phosphate-Treated Mice
TYpe of Lesion (Sex)
Liver T1DDors (Females)

AdenClDa
Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table testsd
Incidental t1DDor testsd
Corchran-Armitase trend
Fisher's exact test
CarcinClDa

Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table tostsd
Incidental t1DDor tostsd
Corchran-Armitase trend
Fi sher' s exa ct to st
AdenCDa or
carcinoma

Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table testsd
Incidental t1DDor testsd
Corchran-Armitaso trend
Fisher' sexact test
Circulatory System
Tumors (Hemansio-
sarcomas) (Males)

Overall ratesa
Adj usted ratesb
Terminal ratesC
Life table testsd
Incidental t1DDor tostsd
Corchran-Armitase trond
Fi sher' s exact test
testd
,

testd
testd
testd
Control
2/48(4'11)
5.5"
1/32(3..)
P=0.S17
P=0.S10
P=0.436
0/48 (011)
0.0'11
0/ 32( 0.)
P=0.012
P=0.006
P=0.007
2/4S(4'11)
5.5"
1/ 32( 3'11)
P=0.031
P=0.020
P=0.016
7/ SO (14..)
17 .S"
4/34 (12'11)
P=O.OOSN
P=0.008N
P=O.OOSN
Low Do se
4/S0(S..)
9.5'11
4/42(10lIl)
P=0.4S3
P=0.404
P=0~3 59
4/50(8..)
9.5"
4/42( H»tt)
P=0.103
P=0.103
P=0.~64
8/S0(16..)
19..
8/42(19'11)
P=0.10S
P=0.OS7
P=0.OS3
0/ SO( 011)
0.0lIl
0/28 (0lIl)
P=0.020N
P=O.OllN
P=0..007N
High Dose
3/S0(6cr.)
7.5"
3/40(7..)
P=0.S91
P=0.SS1
P=0.520
7/ SO( 14")
16.7"
S140( 13..)
P=0.019
P=0.007
P=0.007
10/50(20lIl)
23.S"
S/40(20111)
P=0.039
P=0.020
P=0.017
1/49 (2IJI)
2.6"
1/3S(3..)
P=0.030N
P=P=0.041N
P=0.032N

-------
44
Tabl e 12.
(Continued)
Type of Lesion (Sex)
Control
Low Dose
High Dose
Hematopoietic Tumors    
(Malignant Lymphoma)    
(Females)     
Overall ratesa   14/49(29..) 10/ SO( 20i) 6/S0(12..)
Adj usted ratesb   3 S . S.. 23.3" 13.8"
Terminal ratesC   7/32(22CW1) 9/42(21..) 4/40(10i)
Life table testsd  P=0.012N P=0.103N P=0.020N
Incidental tumor testsd testd P=0.024N P=0.461 P=0.021N
Corchran-Armitage trend P=0.027N  
Fisher's exact test   P=0.224N P=0.03SN
Pituitary Adenomas (Females)    
Overall ratesa   6/41( 1,.) 8/47(17") 2/47(4..)
Adj usted ratesb   22.2" 20.Oi S.Oi
Terminal ratesC   6/27 (22CW1)  8/40(20i) 2140(")
Life table testsd  P=O.030N P=0.S34N P=0.04IN
Incidental tumor testsd testd P=0.030N P=0.S34N . P=0.04IN
Corchran-Armitage trend P=0.082N  
Fisher's exact test   P=0.496 P=0.094N
a
Number of tumor-bearing animals/number of animals examined at the site

bKaplan-Meier estimated tumor incidence at the end of the study after
adjusting for intercurrent mortality

cObserved tumor incidence at terminal kill

~eneath the control incidence are the P values associated with the trend
test. Beneath the dosed group incidence are the P values corresponding to
pairwise comparisons between that dosed group and the controls. The life
table analysis regards tumors in animals dying prior to terminal kill as
being (directly or indirectly) the cause of death. The. incidental tumor
test regards these lesions as nonfatal. The Cochran-Armitage and Fisher's
exact test compare directly the overall incidence rates. A negative trend
or lower incidence in a dosed group is indica ted by N. .
Sour ce :
NTP 1984

-------
Table 13. Genotozicity of Tri(alkyl/alkozy) Phosphates
Species/Cell System
Ref erence
Do ie I
Concentration
Metabolic
Activation
Reanl ts
TRIMEIBYL PBOSPHATE
Microbial Aasay.
Salmonella tvuhimuriu.
(reversion as.ay)

TAl5S!. TAl 537 . '
TAl538. TA98. and
TAl 00

TAl535. TAl 537 .
, TAlOO. TA98
Salmonella tvuhimurium
(reversion assay)

hi1C117. hisG46.
TAl530. TAl5S!

LT2 hhG46.
LT2 hhG46
(I-Utrecht) .
TAl530
Bscherichia ~
(DNA repair)

Ifl
1"7
at871
11'2. lP2uvrA
01561. 01571.
(]I 611. IP67. IP12
Standard
+ and -
0.05-500Pl/plate
+ and -
Standard
70 pmol
~b
+ and -
+ and -
+ and -
Standard
POI. in TAlOO. only.
with and without 89;
0.0003 rev./Dllo1ea

POI.. 0.0009 rev./nmolea
in TAlOO with S9
POI. in hi1C117. only
Rev. in R-Utrecht Itrain
only'
MICc = 12.000 PI
with and without S9
MIC = 12.000 PI
without S9~ 8.000
PI with S9
IIIC co 1.500 PI
without. 3.000 PI
with S9; potency =
0.0005 ICs/Dllole

Pos. in .11'2.
I1'2uvrA. 01611. 'P67.
IP12
De Flora et ale 1984;
De Flora 1981
Bruce and Oeddle 197~
Banna and Dyer 1975
MacPhee 1973
~
(J'1
De Flora et al. 1984
Banna a~d Dyer 1975

-------
SpeciellCel1 s,ltem
TRIKEIBYL PHOSPHATE
lIicrobial AuaYI
(continued)
Phaae "T4B
Schiaolaccharomvcel
1)ombe
Serratia marcelcenl
aU
a21
lIicronucleul Allay
lIoule (C57BL/6 J: C3B/He)Fl
Speftl Abnormal i ty Auay
IIoUI. (C57B1/6 J: C3B/Be)Fl
. Do Ie I
Concentration
Not char
(pouibly 0.08411)
NJb
25-100 ma/rrL
25-100 ma/IL
Fractionl of LDSO
Fractionl of LD50
10G-I000 milk,. Ipe
5 conlec. daYI
Table 13. continued
lIetabol ic
Activation
NAd
NAd
NAd
Re sui ta
4.7 mut./I000.
47 J: control (24
houri UpOI.);
0.4 mut./IOGO.
4 J: control (48
houri expos.)
POI.
188 (PiO.Ol> to
535 (PiO.001)
~ of control mean
nO. of telt coloniel
107 to 183 (PiO.001)
~ of control m.an
no. of t.st colonies
POSe
POSe

POI.: 4 and 5'r.
abnoftlal lperm at
1 wk after -700 and
1000 ml/ka. relpectively
Reference
Kononova and Gumanov 1971
Barale et al. 1979
Dun 1972
~
~
Bruce and Heddle 1979
Bruce and Heddle 1979
Iyrobek and Bruce 1975

-------
Table 13. continued
Species ICe 1 1 System
Do se I -
Concentration
Reference
Metabol ic
Activation
ReBUl ta
TRIIIETBYL PHOSPHATE
(oontinued)
Host Mediated Assay
Mou,e
1250-1750 malta, I~
CY~oaenetic Bffeots
Mouse (Q strain)
1000 malta, Ipe
(biabest tolerated
do se )

1250-1750 ma/ta
Mouse (strain
not identified)
Rat (Osborne-Mendel)
20'00 malta, Ip8;
1000 ma/ta/day z 5, Ipe
2000 mslta, orally
1000 ml/ts/day. orally,
z 5
NAd
NAd "
NAd
NAd
NAd
NAd
r,/
NAd
Nea.
Nea. - no cbromo-
some damaae in pri-
mary spermatocytes

Pos. Dose response,
msd.1III ef feet s
48 bours after
tree hlent (aaps
not iDol uded)
At 24 b after
trea hlent. 18.9t1
of cells bad aber-
rations (aaps not
inol uded

fAt 6 b after treat-
.ent, 13.12t1 of cells
bad aberrations; 0.5t1
of Dea. controls bad
aberratiops (aaps
not inoluded)

"SAt 24 b after tre~t-
ment, 10.5t1 of cells
bad aberrations (saps
not inoluded) "

fAt 6 b after treat-
.ent 8.7t1 of cells bad
aberrations; 1.7t1 of
Del. controls bad
aberrations (aaps
not iDol uded)
Farrow 1975
Dearaeve et al. 1984
Farrow 1975
Leaator et al. 1973
~
'-I

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SpociealCell System
TRIMETRYL PBOSPHATE
CytoseneUc Bffects
(oontinued)
Human lymphooytel
(Blood)
Chicken embryo
Dominant Lethal Allay
Moule
Table 13. continued
Dolel
Concentration
Treated in vitro with
10-5 to 1 . for 5 or
. 24 h
15001lS
1000 ms/ts
500 ms/ts, orally,
for 5 daYI

1250 ms/tl, Ire, once

500-2000 ml/tl, Ire:
500-10~0 ms/tl, orally
x 5
5-day treatment
at or near .ax.
to1. dOle.. orally
Metabol ic
Activation
NAd
NAd
NAd
HAd
HAd
NAd
. Relul ts
Dole-related increases
in anaphase aberrations
at 1-100 ...
dOle-related increases
metaphase aberrations:
breatl - 0-2~ and
2.7-6" with 1-100 8M
for 5 hand 0.01-50
8M for 24 h,. relpectively

POI.. lowelt dOle
producinl Iii. inc. in
lilter chromatid exchanlel
(P(O.OI); no chromosomal
breab
Bi.h muta'8nicity,
particularly at
poltmieotic Itasel

POI. in wts 1 and 2
of maUnl

POI., wt 2 of matins

POI.; lilDificant
Ume- and do se-
related effeots on
number of i.plantl,
early deathl, and
pre.nancy ratel,
maUn. wta 1-3

POI. for 2 weets after
treatment
Reference
Soderman 1972
Bloom 1982.
.f:o
CD
Desreave et al. 1979
Parrow 1975
Parrow 1975
Bpltein et al. 1972
Newell et al. 1976

-------
Table 13. continued
Species/Cell System
Dose/
Conceniration
Metabol ic
Ac.ti va ti on
Renl ts
Reference
TRIMETBYL PHOSPHATE       
(continued)         
Recessive Lethal Assay       
DrosoDhila         
lIelanoRalter     NAd    
(Larvae)   Ni  POI., 83~ lethals Hanna and Dyer 1975 
      (p = 0.001)  
(Exposed from  0.001-0.005M NAd 5.7-7 . 7~ le thIs Dyer 1975 
18rv ae to add t) (in medium)  NAd 6. 7-7 .5~h  
   0.01-0.025 M     
   (in lIedium)  NAd    
   Controls  0.4~ lethal I   
(Adul ts)   Ni (fed)  NAd POI. at one or Valencia 1977. al reported 
      more expoure levels in Lee et al. 1983 
         ~
Plant Assay s         \0
Tradelcantia clone 4430 13 ppm (vapor) i  POI. (P=0.02) Van't Boff and Schairer 1982 
   for 6 hra      
Barley (seedl)  S1JI for 5-22 hra  leakly poI. !ruson 1973 
TRIBDTYL PHOSPHATE       
Miorobial ASlaYI        
Salmonolla tvohimuriull       
hbC117, hhG46, Standard   NoS.  Banna and Oyer 1975 
TAl530, TAl534       
TA98, TAlOO,  -97 -97 ,000 PI/p.htek + and - NeS.  FlfC 1985b 
TAl 535 , TAl537       
TAl 538          
g. ooli         
IP2, IP2uvrA  Standard   NeS.  Hanna and Dyer 1975 
0061, 0071,        
CM611, WP67, WP12       
DrosoDhi1a   mb  NAd NeB., 11.1~ lethal I  Hanna and Dyer 1975 

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Table 13. continued
Species/Cell System
Oo'se/
Concentration
Metabol ic
Activation
Resul ts
Reference
TRI (ETBYLIIEXYL) PHOSPHATE
Microbi,al Assay s

Salmono11'a tvuhimuriumJ
TA98, TAlOO,
TAl 535 , TAl537
106-10,000 Ps/plate
+ and -
Nel.
Zieser et 81. 1982;
NTP 1984
TRI (01TfOUETBYL) PHOSPHATE
Microbial Assays
Salmonella tvuhimurium
TAU, TAlOO,
Ta1535, TAl537

TA98, TAlOO,
TA1535, TA1537
mb
+ and -
Nel.
NTP 1985
0-10,000 PI/plate
+ and -
Nes.; toxicity at
5,000 and 10,000
PI/plate
Monsanto 1985 a
U1
o
a
bRev. '" reversions
NO .. Not siven
cMIC .. Minimum inhibitory concentration;
for sodium ohloride were >3000 for all
d >300. The potency for sodium chloride
NA = Not applioable
elP .. Intraperitonul inj ecHon
fiM '" Intramuscular injeotion
These results are oombined data from 4 different laboratories. The
aberrations inolude chromosomal laps. breaks, and rearranlementl.
IThese relults are oombined data from 4 different laboratories, at the
time of maximum effeot. The aberrations inolude ohromolomal sapI, breaks,
and rearranSement s. '
hfbe frequency of lethals at low dOles, equal to or Ireater than the
frequency of lethals at the hisher dOle I il luSselted by the author I to be
due to the faot that the kill inS of mutasen-senlitive oelll il .uoh lell at
ilower dOles.
Lowest ooncentration at which effeot oocurred. This syltem il uniquely
Buited for the detection of saBeous muta8ens.
Jpreinoubation modifioation of Ames et al. (1975, as reported in Zeiler et
kal. 1982). Tested in 3 different laboratories.
Calculated from concentrations of 0.1-100 pL/plate and density of
0.9727 at 25°C
for comparilon, the MIC values
except eM871 wihout S9, which was
(AMICI/Dllole) is <0.00001.

-------
Sl
cytogenetic assay (Farrow et al. 1976), and in the mouse sperm abnormality
test (Wyrobek and Bruce 1975)r and was negative in the host-mediated assay
. (Farrow etal. 1976). Trimethyl phosphate has been used or suggested for
use as a positive control in the mouse dominant lethal and bone marrow
assays (Farrow et al. 1976, Legator et al. 1973).

Tributyl phosphate was negative for mutagenicity in. Salmonella  and j.
~ (Hanna and ~er 1975); tri(ethylhexyl) and tri(butoxyethyl) phosphates
were negative in Salmonella (Zieger et al. 1982, NIP 1985, Monsanto 1985a).
Mutagenicity data for other compounds were not ~ound.
b.
mA Alkylation
Trimethyl phosphate, an industrial alkylating agent, alkylates nucleic
acids preferentially at the N-7 of guanine (Mailing and Wassom 1977, as
reported in Bemminki 1983). In a test system utilizing 4-(p-nitrobenzyl)-
pyridine to detect alkylating agents, the alkylating activity of trimethyl
phosphate was increased almost lo-fold by a chemical activation system
(Archer and Eng 1981). Debruin (1976) de scribe s trimethyl phosphate as an
alkylator of relatively weak potential. In comparison to triethyl phos-
phate, another trialkyl phosphate of only one carbon longer, trimethyl
phosphate's alkylating capacity is 600 times greater (Braun 1966, as
reported in Kononova and Gumanov 1971). Kononova and Gumanov (1971) demon-
strated the alkylation of T4B phage mA by trimethyl phosphate on the basis
of the production of 7-methylguanine along with other products of alkyla-
tion.
c.
Cytotodci ty
Trimethyl phosphate, at the concentration of 2.5 x 10-S M was lethal
to BeLa cells in culture, but had no antimitotic activity; 10-S M was not
lethal and had no antimitotic effects (Deysson et al. 1966, as reported in
Chem Abstr 6S:9S43b). At 10-4 M, trimethyl phosphate inhibited growth and
mitosis in pea roots, but did not produce abnormal mitosis; 2.S x 10-4 M.
trimethyl phosphate inhibited mitosis followed by cell death within 24
. hours. .
S.
Teratogenicity/Repr~ductive Effects
a. . Effects of Alkyl Phosphates
Developmental toxicity and reproductive effects data, found primarily
for trimethyl phosphate and tributyl phosphate, are summarized in Table 14.
Treatment with trimethyl phosphate results in a temporary period of reduced
fecundity or infertility (supporting data in Table 14). The magnitude of
the reduction in fecundity and the duration of the period of sterility are
a function of dose and duration of exposure. Tributyl phosphate was
"s1 ightly teratogenic" in hens, while trHo-cresyl) phosphate was not
(Roger et al. 1969).

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Table 14.
Reproductive aud Teratoaenic Effects of Alkyl Phosphates
Compounda
Reference
Species
(Sn: Treated)
Dose/Routeb
Effects
nIP
Hanna and Kerr 1981
TMP
TMP
TIIP
nIP
TIIP
Rats
(M)
Rats
(M)
Rats
(M)
Mice
(M)
Mice.
(M)
Rabbi h
(M)
250 ma/ka. 5 days/week for 30 days
or 6 dayslweek for 60 days; oral
100 ma/ka. 5 dayslweek for
1 month. 600 ma/ka. 5 days;
750 ma/ka once weekly.
"ohronic" exposure;
1. p. or aavaae
100 or 250 ma/ka in
5 daily doses;
oral
1 a/ka. 5 daily doses;
i. p. or oral
750 ma/ka aiven for 5 days;
1.5 a/ka for 5 days; 1.5 a/ki
for 5 days/week for 1 month;
i.p~ or by Savaae
200 or 325 sa/ka for
13 weeks or 750.ma/ka in 1 dose;
.1. p. or by aavaae
Infertility; abnormal
speraatoaenesis; loss
of aerm cell aotivity
(60 day aronp)
Fecundity. dependent on
dose and duration of
treatment. ranaed from
0-2" of normal first
week after treatment
stopped; 600 ma/ka for
5 d and 750 ma/ka. chronic
eJ:Posure. produced most
severe effects; fertility
returned 2-12 wks after
treatment; no ohanae in
histology of testis or
in speraatoaenesis
Infertile 2 to 5 wks
after treatment. depend-
inS on dose; spera in-
COlipe tent
Sterility in weeks 1-2
follOlJ inS eJ:Posure by
ei ther route
Reversible sterility;
severity and duration
of effeot dependent on
dose and duration of treat-
ment; with 1.5 ,Ik for 1 80.
sterility persiated for 2 wks
post teraination of treat-
ment then returned to nor-
881 within 6 weeks. Hist-
o . .. .
oloay and lpermatoaenesis
noraal
200 s,/k, reduced feoundity
to 501 by wk 3; 325 ma/ka
oaused sterility from week
5-13; 750 ms/k, reduced fe-
cundity to 34" durina wk 1
pOlt treatment; fertiliy re-
turned wk 1 or 2 after treat-
treatment; no ohanae in testis
or speraatoaenelis
Harbison et al. 1976
1 aokson and lone s 1968
(J1
N
laokson and 10nes 1968
Harbhon et al. 1976'
Harbilon et al.1976

-------
Table 14.
continued
Compo 1IJI da
Species
(Su Tree ted)
Ref erence
Dose/Routeb
Effects
'IMP
Toad
(Xenollus ~)
Toad
(Xenollus !uW)
spematoz.oa
nIP
DrosollhU fa
melanoaaster
(II and F)
TIP
DrosollhU fa
melanoaaster
(II and F)
. TIP
DrosollhUia
(II)
'lBP
Rats
(I and F)
11IP
Ben
TOCP
Ben
120 ms/mL for 30 minutes
20. 40. 80 81/L
for 0.5. 1. or 2 hours
13.8-20.2 IlkS;
i. p. to adul ts
Larvae ezposed to
0.001-)0.005 II
TEP in medium
0.003-0.005 II;
or Ireater ill medium
.170 or 510 IIl/klc
for 14 days; savale
5 81/ell; injectioll
10 IIl/ell; iuJectioll
49' reductioll ill ova under-
soilll cleavale; reductioll
ill spem lIotility
Fol109inl fertilizatioll with
1IJIezposed ova. furr09inl of
allillal pole without cleavage
at 40 and 80 IIIg/.. after
1 hour. alld at 20 and 40
mg/mL after 2-hour exposure
II-day sterility with
19.4 and 20.2 IlkS;
6-day sterility with
13.8 alld 15.8 I/kl;
no effect 011 fOllales
11 day sterility ill
adult .ales ezposed to
0.002-0.003 II TEP; alld
ill all .ales ezposed to
0.004-)0.005 II; exposure
durilll last day of larval
stale necesaary to produce
only temporary effects
Ezposure of larvae caused
reversible infertility
lIicroscopic delellerative
challies in.semilliferous
tabules of 1 of 4 hilh
do se lIIal e s; no challie s
ill ovaries of fOllales
H Slilhtly tera" tOlellic ;
reductioll ill body lellith.
les lellith. weilht. alld
, hatch
No embryonic abllomal-
ities lIor aay muscular
weakness or other ab-
lIormalities ill hatched
chicks
Hemsworth alld Wardhansh 1978
10lles alld lacksoll 1974
Hanna 1980
Hanll8 1980
U'1
(N
Dyer 1975
Laham et al. 1984c
Roler et al. 1969
Roger et al. 1969
aTlfPbtrimethyl phosphate
TBP=tribatyl phosphate
TOCP=tri(o-cresyl) phosphate
b
i. p." intraperitoneal inj ection

cCalculated fram doses of 0.14 mL/kl alld
0.42 mL/kg and dens! ty of 1.2144 at 200C

-------
54
b.
Mechanisms of Action of Trimethyl Phosphate
. Three mechanisms potentially responsible for the sterility effect of
trimethyl phosphate have been proposed: (1) reduction in acetyl transferase
activity resulting in reduced sperm motility; (2) reduction in circulating
testosterone; and (3) disruption of normal loop formation on the Y-
chromosome. Significant reductions in choline acetyl transferase activity
(Harbison et al. 1976) and in carnitine acetyl transferase activity (Adatsi
et al. 1984) have been observed in caudal spermatozoa of rats. A marked
. reduction in sperm motility was also noted (Harbison et al. 1976. Adatsi et
al. 1984). Harbison et al. (1976) proposed that suppression of acetyl-
transferase may affect sperm motility through its effect on intracellular
concentrations of acetylcholine. Adatsi et al. (1984) stated that the
presence of the choline acetyltransferase system in spermatozoa is in
doubt. The carnitine acetyltransferase system stimulates spermatozoal
respiration and motility and its reduction by trimethyl phosphate may be
the mechanism of sterilization in rats.
In support of the second proposed mechanism. Carstensen (1971)
reported a 401 reduction in circulating testosterone in rats receiving 100
mg/kg trimethyl phosphate for 5 days by gavage. The rats also showed a
significant decrease in the prostate weight/body weight ratio. No diff.er-
ences between control and treated rats were observed for pituitary. testes.'.
and seminal vesicle weights. Carstensen concluded that reduction in circu-
lating testosterone produced by the testes. induced by trimethyl phosphate.
was a reasonable cause of the decreased prostatic weight. However. because
spermatogenesis proceeded normally. the question of the cause of functional
steril ity remains. .
Thirdly. Hanna (1981) proposed that infertility in Drosouhila hvdei
may result from the disruption of the normal loop formation on the Y-
chromosome in Drosouhia. This condition is similar to that observed in X/O
sterile Drosouhila males.
6.
Other Effect s
a.
Human Toxici ty
Based on human experience. Monsanto (1985b) suggests that alkyl phos-
phate esters may cause skin. eye. and respiratory irritation in exposed
indiv idual s.
Tributyl phosphate is classified as a strong skin. eye. and respira-
tory irritant (Monsanto 1985a) (also see Table 19. p. 62). Workers exposed.
to 15 mg/m3 of tributyl phosphate vapor had headache and nausea (Mastromato
1964. as reported in ACGIH 1984); hot vapor caused severe eye and throat
irritation (Mackison et al. 1981). Undiluted tri(ethylhezyl) phophate
(single application) was slightly irritating to the skin of volunteers
(Weigand et al. 1969).
. According to Union Carbide (1957. as reported in MacFarland and Punte
1966). Sill of 200 subj ects tested with tri(ethylhexyl) phosphate had a "son-
d tivity reaction" in the pa tch test. No details were given. .

-------
55
T~i(butoxyethyl) phosphate (12 applications) were slightly irritating
to the skin of volunteers, but subsequent challenges with tri(butoxyethyl)
phosphate did not el~cit a sensitizaion reaction (Monsanto 1985a).
No information was found regarding the toxicity of triallyl phosphate
in humans. Allyl esters in general can be (1) absorbed through the skin;
(2) are irritating to the eyes, lips, and other sensitive areas; (3) are
skin sensitizers in susceptible individuals; and (4) upon heating, release
allyl alcohol, which is irritating in small quanti ties (Beacham 1978 r.
b.
Animal Toxicity
In order to compare the effects of the tri(alkyl/alkoxy) phosphates in
experimental systems, the data are summarized according to acute, subacute
and subchronic exposure in Tables 15, 16, and 17, respectively. . The
results of in vitro and irritation studies are summarized in Tables 18 and
19, respectively. The effects oftrHalkyl/alkoxy) phosphates are also.
summarized below according to target organ or system.
Anticholinesterase Activitv and Neurotoxicitv
- Trimethyl phosphate does not have anticholinesterase activity as do
some organophosphorus compounds (lackson and lones 1968, as reported
in Conner 1979; Oishi et al. 1982, Table 17). A narcotic effect and
paralysis have been described following dosing with trimethyl phos-
phate (Deichmann and Witherup 1946, as reported in Verschoyle and
Cabral 1982, Vandeker 1957, Fasset 1963) (Table 15). Functional and
morphological changes in the nervous system (such as impairment of
neuromuscular impulse transmission, impairment of conduction velocity
of sensory fibers, and degeneration of spinal tracts and peripheral
nerve fibers) were observed in dogs treated with trimethyl phosphate,
particularly at doses causing severe morbidity (Schaeppi et al. 1984,
as reported in DIALOG [BIOSIS Previews] 1985) (Table 15). Compound-
related neurological symptoms in other species included anesthesia and
coma in rats (Vandekar 1957), paralysis in rabbits (Fassett 1963)
(Table 15 and. 16). Trimethyl phosphate did not cause delayed neuro-
toxicity in hens in subacute doses of 50 mglkg (Bollingshause et al.
1981) (Table 16).
- Tributy1 phosphate has weak anticholinesterase activity (Kalinina
1971, Sabine and Bayes 1952) in human, but not bovine, serum (Oishi,
unpublished observations, as reported in Oishi et al. 1980), and in
human RBC and plasma (Sandmeyer and Kirwin- 1981). The compound has
definite neurotoxic effects in rats that include (1) cholinergic symp-
toms and (Sabine and Bayes 1952); (2) hyperemia of the brain and
disintegration of the nerve cells of the cerebral cortex (Pupesheva
and Peresedov 1970, as reported in MEDLARS II [TOXBACK '65] 1985); (3)
twitching, paralysis, and coma (Sabine and Bayes 1952);. and (4)
anesthesia (Vandekar 1957). &ci tabU ity was 1 isted by Kallnina
(1971) as a symptom of tributyl phosphate poisoning, but the species

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Phosphate/Species
Treatment
Acute Toxicity of Tri(alkyl/altosy) Phosphates
Effect s
Reference
Table 15.
TRIJIETIIYL
Rat
Rats
TRIB1Tl'YL
Rats
Rats
Rats
Rata
Rata
Mice
Chickens
Chickens
Chickens
140 IIS/taa, Ipb
(a) 1.8 a/ta,. IVb
(b) 2.4 a/ta, IVb
Larse oral or Ipb doses
(.) 70 or 140 mac, Ipb
(b) 70 mac, Iltb
(c) 140 mac, orally
(a) 80 ma/ta, IVb
(b) 100 ma/ta, IVb
266 ms/tad, IY'
Inhalation of
x 6 hr

1 a/ta, Ipb
123 ppm
3.68 ma/ta, orally
(cumulative dose)
1.84 altaId x 2,
orally; sacrifice d 42
(LD50 = 1.84 S/tS)
100 s/kS. orally
2-fold increase in serum
B-slucuronidase activity
3 h post treatment

(a) Sublethal dose; inco-
ordination, weatness
(b) Lethal dose; deep anes-
thesia, dyspnea, weatness,
sleepiness, coma
Weatness, dyspnea, pulmonary
edema, twitchina; no para-
lysis in survivors,

(a) TwitchinS, paralysis, coma
(b) Pa ralysts
(c) Labored breathina, hyper-
sa! ivaUon

(a) Sublethal dose; incoordin-
ation, mild anesthesia,
weatne'ss
(b) Lethal dose; anesthesia,
dyspnea, respiratory failure

90-fold increase in serum
B-slucuronidase activity
3 hr post treatment; 27-fold
increase at 6 hr. No effect
On cholinesterase activity
0/3 deaths
Paralysis comparable to that of
0.5 malt, of d-tubocurarine

No delayed neurotoxioity
No behavioral or histoloai-
cal sisns of neurotoxioity
Delayed neurotoxicity
Suzuki et al. 1977
Vandeb r 1957
Fassett 1963
Sabine and Bayes 1952
(}1
'"
Vandeb r 1957
Suzuti et al. 1977
Fassett 1963
Chambers and Casida 1967e
Bollinsshaus et al. 1979f
10hannsen et al. 1977
Abou-Donia, unpublished
resul tse

-------
Table 15.
continued
Phosphate/Species
Effech
Reference
Trea tment
n!(ISOBOTYL)
Rats
Large oral or Ipb doses
Weakness. dyspnea. pulllonary
edella. twitching; no para-
lysis in surv ivors.
TRI (ETIIYLBEXYL)
Mice and rats
Lethal doses
434 IIg/kg. Ipb.g
Delayed deaths; no paralysis

3.2-fold increase in serum
B-glucuronidase activity
3 hr post treat8ent; no
increase at 6 hr.

No neuropathological effects
Rat.
Chickens
2.500 mg/kg. crop
inj ection
TRI(B1ITOXYETHYL)
Guinea pigs
"Large dose"
Ataxia. muscular flacoidity.
lOll of reflexes

Convul sions. tremors. hypo-
thermia. increased secretions.
tear formation
Rats
Ipb inj ect!on.
dose not given
TRIALLYL
Mice
Le thai do se
(0.5 g/kg. Ipb)
Ataxia and dyspnea; no paralysis;
no delayed deaths
Fassett 1963
;Calculated ftom administered dose of 1 mmole/kg and II.W. 140.08
IP = Intraperitoneal inj ection
1M = Intramuscular injeotion
IV = Intravenous inj ection
c70 mg calc.ulated from administered dose 0.1 mL and "density of 0.9727 g/rrL at 250C;
d140,mg calculated from administered dose 0.2 mL and density of 0.9727 g/mL at 250C
Calculated from administered dose of 1 mmole and m.w. 266.32
e
fAs reported in ACGIB 1984
As reported in Abou-Donia 1981
~Calculated from' administered dose of 1 mmole/kg and II.W. 434.64
As reported in Laham et al. 1984b

.Componnd identified only as "trioctyl phosphate". Could be CAS No. 1806-54-8
Fassett 1963
Fasse tt 1963
Suzuki et ale 1977
MacFarland and Punte 1966
Lefaux 1968h
<.T1
-...J
Laham and Long. nnpublished
observationsg

-------
Tabh 16.
58
Trea bunt
Subaoute Tozioity of Tri(alkyl/alkozy) Phosphatea
Effeots
Phosphate/Speoies
Reference
TRIJIETIIfL
Rabbi t
Bens
TRIB1Tl'YL
Spraaue-Dawley rats
Sprape-Dawley rat'
Spraaue-Dawley rat
m ( B'l'IIYLIIEXYL)

F344/N rata;
5 lIahs, 5 f_ale.
per aroup
Rata
Rat.
B6C3Fl lIice;.
5 lIale., 5 f-ale.
per aroup
Rabbit
m( B11l'O:mmm.)

Spraaue Dawley
rat.
364 IIs/ka/d z 6 d;
or.lly; 2429 IIs/ka/da
z 20 d on .kin

50 IIS/kS/d z 10 d,
IP
0, 130 or
3S9 IIs/kab
orally for 14
48ys
0, 260 and 3S9 lIa/ka/dd
orally, for 14 days
140 or 200 s/ka/d
for 7 d, by savaae
0, 375, 750, 1,500
3,000 or 6,000 lIa/ka
in corn oil by savase
14 consec. 48ys
400 IIS/kS in diet for
30 d

430 or 1,550 IIs/ka in
"subacut." duraUon
0, 375, 750, 1,500
3,000 or 6,000 lIa/ks
in corn oil by aavase
14 consec. cI8ys

92.6 lIaf applied to skin
5 d/-k for 2 or 4 wb
816 and 1,142 IIs/kac,
femaln; 0.80 and 2.24
IIL/ka, lIale. for 14 d,
by savase
Flaooid and spasUc paralysis
No delayed neurotozioity
Fellales: Sisnificant (P<0.05)
decrease in hemoslobin (P<0.05)
and spleen wat. (P<0.05) in
hish dose sroup; deoreased
lIean corpusoular hemoslobin
and lIean corpuscular haD-
slobin ooncentration (P<0.05)
in low dose sroup. Increased
'liver wst. (P
-------
Table 17.
Phosphate/Species
Treatment
Subchronic TOIicity of Tri(alkyl/alkozy) Phosphates
Reference
Effects
TRIIIETBYL
Doss (5)
1.214 IISa daily
for 1-4 110..
rout e not
stated
DoS (1)
14.573 IISC daily.
duration not
cl ear. route
. uot sta ted
lQ.-lhtar rats
o or 0.5~ in diet
for 9 wks
TRIBUTYL
lQ.-'htar rats
O. 0.5. or l,()II,
in diet for 10 wks.
iQ.-lhtar rats
o or 0.5~ in diet
for 9 wks
lQ.-'htar rats.
ddy mice
O. 0.05. 0.2. or 1~
in diet for 3 80.
At 4 wks. 
-------
Phosphate/Species
Treatment
Table 17.
cont~
~ffects
Reference
TRIBuTn
(continued)
Sprasue-Dawley rats,
15 .alel, 15 females
per aroup
Sprasue-Dawley rats,
12 .ales and 12 females
per sroup
TRI (ETBJIIIR1:YL)

F344/N rats;
10 .ales, 10 females
per sroup
B6C3FI mice;
10 .a es, 10 females
per sroup
'Ouinea piss,
20 .al u/aroup
Doss,
2/aroup
m (,BUTOIYE'l1IYL)

Spraaue-Dawley
rats
o. S, 40, 200,
1,000, or 5,000 ppal'
in diet for 13 wks
0, 191.5, or 340.5
.s/ka by savase
for 18 wks
0, 250, 500, 1,000
2,000 or 4,000 ms/ks
in corn oil by savase
5 d/.k for 13 wk.

0, 500, 1,000, 2,000
4,000 or S,OOO ms/ks
in corn oil by savase
5 d/.k for 13 .k
0, 1.6 or 9.6 .s/.3,
6 hrld, 5 d/.k, iDhal.
for 12 .b
0, Ig.8, 26.4, or 85
.s/. , 6 hra/d, 5 dlwk,
for 12 .b
255 or 510 .s/kad
by savaae, 5 d/.k
for 18 .b
No deaths; effeotl at two hiah-
est doses: lisnificant increases
in prothrombin aDd aotive partial
thraaboplastin ti.es and in SGPTe
and SGG~ activitiel; elevated
cholesterol and calcium levels;
urinary bladder hyperplasia; de-
pressed body wst and food con-
sumption. No effect levels: 13.8
mS/k/d for .ales, 80.9 ma/ka/d for
females.

Diffuse urothel hi hyperplada
of the urinary bladder in all
treated .alel and females.
Fooal nodular hyperplasia
in sOllIe males at both doses.
some .ales at both doses.
No deaths. Wst. loss in .alel
at 4,000 ms/ka, in f..a1es at
2,000-4,000 .s/ka. No other
effects noted at necropsy.

No deaths. Wat. depreued in
in .ales It 8,000 .a/ka, in,fe-
.ales at 4,000-8,000 .a/t.. In-
flammation of aastric .ucosa,
all aroups;u1ceration of fore-
stomaoh in 1/10 .alel at 2,000
and 8,000 .a/ka, and in 1110
and 3/10 f..alel at 4,000 and
8,000 .a/ks, respeotively.

Lunl con,estion; sianificantly
increased terminal body wats;
decreased kidney to body wat
ratiol
Dole related deterioration in
conditioned avoidance technique
Reduotion in nerve conduction
velocity (P(O.OOI), increase
in relative and ablolute re-
fractory period (P(O.OOI). Be-
aeneration of myelin aheath,
azonal nellinl.
FIIC 1985c;
Cascerl et aI. 1985
Laham and Lons 1984
NTP 1984
NTP 1984
0'1
o
MacFarland and Punte 1966
MacFarland and Punte 1966
Laham et al. 1984b
a
bCalculated frOll administered dose of 1 aL and
cAI reported in DIALOG (BIOSIS Previews) 1985
dCalculated from administered dose of 12 mL and
Calculated from administered doses of 0.25 and
eSGPT = serum alutamic pyruvic transa.inase
fSGGT = serum y-sluta.yl transpeptidase
P.'~"'.._A #~~ aA.~"~.....A Anses of 0.2 and
dud ty of 1.2144 s/mL at 20.C
density of 1.2144 a/aL at 20.C
0.50 mL/kS and density of 1.02 s/mL at 20.C
n ~c -, ...... A.............. ,..# no",.,,,, ..t.".T .... ?~Or

-------
Phosphate/Cell TYpe
Treatment
In Vitro Effects of Tri(alkyl/alkozy) Phosphates
Reference
Table 18.
Effects
TRIMETBYL
HeLa cell s
NA
TRIBUTYL
HeLa ce lls

Human red cell
hemolysa te
NA

486 mgb tribu~yl phosphate
added to 90 l1li. hemolysa te
containing acetylchol ine
as substrate

Details not provided
Human se rum
chol inesterase
Rat brain and
1 iver homogena te s.
. se rum
10-7 -10-2 MC
TRI ( ETIIYLIIEXYL)
HeLa cells-
NA
7-day IC a = 2.1 g/L
50
7-day IC50a = 1.5 g/L

5-7~ inhibition of cholin-
esterase activity
Dose-dependent inhibition
No change in cholinesterase
activity
7-day minimal inhibitory
concentration. 4.8 mg/mL
for total inhibition
Ekwall et al. 1982
Ekwall et al. 1982
Sabine and Hayes 1952
Oishi et al. un-
published observations.
as reported in Oishi
et aI. 1980

Oishi et al. 1980
~
.....
Ekwall et al. 1982
.
IC~O = Geometrical mean between the 7-day total inhibitory and no
beffect concentration. .
Calculated from administered dose of 0.5l1li. and density of 0.9727 1/l1li. at 25°C
cThil is ~he concentration given in Figure 2 of the Oish!2et !~. (1980)
paper. The methods section of the paper states that 10 -10 ~
.01 ut ions were used.
-Compound identified only as "trioctyl phosphate." Could be CAS No. 1806-54-8.

-------
62
Pholphate/Type of Teat
Skin Ind Eye Irritltion Studiel with Tri(a1~1/a1to~) Pholphatel
Effeotl
Table 19.
Speoiel
Treataent
Reference
TRIIIE'l'IIYL
Irritation. Ikin
Irritation. eye
TRIBtrl'YL
Irritation. Ikin
Irritation. Ikin
Corrodon. Itin
Irritation. eye
II! (RTIIVT.II1m'I.1
Irritation. Itin
Irritation. .tin8
Irritation. .tin
Irritatiou. eye
Irritation. eye
II! (BUl'OXYETIIYL)

Initatiou/
lenliti.atiou. .tin
Irritatiou. .tin
Irritation. eye
Rabbit
Rabbit
Rabbi ta
Rabbitl. ratl.
.uiua pi.1
Rabbit
Rabbi ta
Rabbi t
a_an (30)
vol unteers)
a_an
Rabbit
Rabbit
a_an (209
vol unteerl)
Rabbit I
Rabbitl
Not ,Iven
Not .iven
Sinl1e app1ioation (0.'1)
to intaot and abrad-
ed stin; oooluded
for 24 hrl; 24 and
72 hr observation
(2 studiel)

Sinl1e or repeated
(daUy for 2 wta)
IUn app1ioation
200 ml/tl. 4 houl

Sinl1e app1ioation
to intact .tin.
oocluded for 4 hra;
observation at 4
nd 48 hrs
0.1 . iutUled
with observations
at 24. 48. 72 hra
and 7 d later;
eyel of ou 8roup
walhed 4 leo after
instillation.
2'0 ml on shaved
sUn
1-1~ in propy1eu
.lyoo1. applied al drOPI
or on uuoovered patoh to
the fonhead

Not .hen
9.26-463 m.b in
coDjunotival uo
Not .iven
12 app1 ioa tienl.
24 hr eaoh ewer
3 wts; 4 ohallenle I
duriDl wt 4

0.5 Illite
in oontact for
4 or 24 hra

0.1 8L in.ti11ed
in au eye; obler-
ved for 21 d
Ra ted 4 on 10al e
of 1-10 (10 mOlt
levere!"

Ra'ted 2 on 10810
of 1-10 (10 mOlt
severe)
Severe irritant;
eryth..a aud edema
in all 6 animals
iD study #1.
Mild irritaut iu
ltudy #2.

Seven iDf1...atory
reaotions in all
animal I
Not oorrosive
Mild. tunsient
irritation without
walhinl; washinl
prevented iDjury.
Mode'rate erythema
within 24 hrl. 1altin,
-1 wt

Mild and variable sen.ationl
iD a few .ubj eot I; mild
imaediate eryth..a in ou
,.. of 200 sabj eot I had
sensi tivity reaotion iD
patch telt

Slipt (at 9.26 to
46.3 m8) to moderate
(at 92.6 to 463 m.)
coDjunotivith

Rated 1 on 10810
of 1-10 (10 molt
severe)
Slipt irritation;
no s.nsiti.ation
Sliaht1y irritatinl
Sliaht1y irritatinl
Smyth et a1. 1969
Smyth et a1. 1969
FMC 1985a
Ka1 inill4 aud Peusedov 1970.
II reported iD Chem Abstr
75: 18020q
FMC 198'a
FMC 1985a
MaoFadnd and Punte 1966
Wei.aud et al. 1969
Uniou Carbide 19'7a
MaoFar1aud snd Punte 1966
Gunt 19740
Manunto 1985a
Monlauto 1985a
Manuuto 198's
a
bAa reported iu MaoFar1and aud Puute 1~66
oCa1culated fraa ad8iniltered dole of 0.01-0.' mL aud density of 0.9260 ./mL at 20'C
A. reported iD IIBILAiS II (TIB) 1985
'C01Ipouud identU bd ouly II .. tdooty1 phosphate." Could be CAS No. 1806-'4-8.

-------
63
tested was not clear. Neurotoxicity was not observed in chickens fed
3.7 g/kg (LDSO x 2) (Johannsen et ale 1977) (Table 1S).

- Tri(ethylhexyl) phosphate, tested ~n acute toxicity assays (Table 15),
had neither a demyelinizing effect in chickens (MacFarland and Punte
1966, as reported in Sandmeyer and Kirwin 1981) nor a paralyzing
effect in mice and rats (Fassett 1963). Dogs, exposed subchronically
(Table 17), however, showed deterioration in conditioned avoidance
(MacFarland and Punte 1966).
- Tri(butoxyethy1) phosphate, administered to rats in subacute (Table
16) and subchronic toxicity assays (Table 17), was neurotoxic, causing
a significant reduction in nerve conduction velocity and increase in
refractory period (Laham et ale 1984a). In acute tests (Table 1S),
the compound caused ataxia, muscular flaccidity, loss of reflexes in
guinea pigs (Lefaux 1968, as reported in Laham et ale 1984b), and
caused convulsions, tremors and hypothermia in rats (Laham and Long
unpubl ished observations,' as reported in Laham et a!. 1984b).
'Heoatotoxicitv
- Trimethyl phosphate produced an increased serum glucuronidase activity
in rats (Suzuki et a1. 1977) (Table 1S).
- Tributyl phosphate produced liver necrosis in rabbits given 0.2 or 0.5
mglkg and in rats given 0.2-S.0 mglkg in a long term study (Zyabbarova
and Teplyakova 1968). Liver necrosis was also observed in rats, along
with increased liver weights" following multiple, unspecified doses of
tributyl phosphate (Pupysheva and Peresedov 1970, as reported in
MEDLARS II [TOXBACK '6S] 1985). Kalinina (1971) observed an increased
retention of bromosu1faleine, indicative of liver toxicity, following
chronic treatment with tributyl phosphate (species not given in trans-
lation). The compound has also caused elevated serum B-glucuronidase
activity in rats, thought to be due to the release of the enzyme from
liver microsomes (Suzuki et ale 1977) (Table 15). .
Neohrotoxic i tv,
Tributyl phosphate-induced urinary bladder hyperplasia was observed in
male male rats given 1,000 and 5,000 ppm and in female rats given
5,000 ppm in the diet for 13 weeks (FMC 1985c). Tributyl phosphate
has also caused increased blood urea nitrogen levels (indicative of
kidney toxicity) in animals treated subchronically (Oishi et ale 1980
[Table 17]) and. chronicallr (Kalinina 1971t and has increased kidney
weights and dystrophy of the convoluted tubules in rats treated with
mul tiple unspecified doses (Pupysheva and Peresedov 1970, as, reported
in MEDLARS II [TOXBACK '6S] 1985).

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.64
Irritation
Skin and eye irritation st.udies with trialkyl phosphates in humans and
animals are summarized in Table 19. The four esters for which data were
found appear to be irritating. to some extent. to both humans and animals.
The degree of irritation varies from slight for tri(butoxyethy1) phosphate
(Monsanto 1985a) to severe for tributy1 phosphate CKa1inina and Peresedov
1970. as reported in Chem Abstr 75:18020q. Sandmeyer and Kirwin 1981. FMC
1985a). Hawley (1981) describes trimethy1 phosphate as a strong irritant.
while Smythe et a1. (1969) and Sax (1984) rated it moderately irritating.
Limited toxicity data were found for tri(isobuty1) phosphate and tri-
allyl phosphate. According to Sandmeyer and Kirwin (1981). tri(isobutyl)
phosphate is expected to exhibit toxicological properties similar to those
of tributy1 phQsphate. and the toxicity of tria11y1 phosphate is likely to
be similar to that of C-2 and'C-3 alkyl derivatives. .
7.
Case Reports and Epidemiological Studies
No data were found.
E.
Environmental Effects
1.
Metabolism
Sasaki et a1. (1982) examined uptake and elimination of tributy1
phosphate in the killifish. Orvzeas 1atines. and found that it was rapidly
taken up and reached a steady-state concentration in one day. The phos-
phate was also rapidly eliminated with a biological ha1f~life of 1.25
hours. Tributy1 phosphate was not detectable in fish after 24 hours in
clean water.
2.
Lethality
Data on the lethality of tributyl phosphate (Table 20) suggest that
the phosphate esters may be moderately to highly toxic for aquatic species.
Trimethy1 phosphate was of low toxicity in the quail (Schafer et ale 197~).
3.
Reproduction
The reproductive effects of trialky1 phosphates in environmental
species are summarized in Table 21. Trimethy1 phosphate. tested in males
or on sperm of several species. caused disruption of spermatogenesis in
guppies at the pre-meiotic stage (Hanna 1982). reduced the percentage of
cleavages of ova. caused furrowing of the animal pole without cleavage of
the vegetal pole. interfered with the sperm motility of Xenonus (Hemsworth
and WaIdhaugh 1978. Jones and Jackson 1974). and reduced fertility in
quails by acting mainly on spermatids and spermatozoa (Jones et a1. 1972).

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   Table 20.' Lethality of Phosphates to EnviroDDental Species      
Compo un da  Speoies  Lethal ity Concentration Condi ti ons   Reference 
    Cd tarion           
TMP Qua il  7 day LDSO 7S0 ms/ks dosed by savase  Schafer et al. 1976 
 (Coturnb ooturnb)           
 Housefly (2-S d. old) 24 hr LDSO >1000 psI jar  adult females   Plapp and Tons 1966 
 (Musoa domestioa)            
 Mosqu! to  24 hr LCSO >1ppm 4 th hstar, larvae  Plapp and Tong 1966 
 (Culex tarsalis)            
'mP "a ter flea  24 hr LCSO 12.8 mgIL sta tic. 2o-230C  Dave et al. 1981 
 (Daub!a muna)            
    48 hr LCSO 3.6S mgIL sta tic. 2o-230C  Dave et al. 1981 
    48 hr LCSO 9.0 mgIL      Monsanto 1985a  
    48 hr LCSO 7S ms/L static     Monsanto 1985a  
    ?2 hr LCSO 2.1 mg/L statio. 20-230C  Dave et al. 1981 
 Zebrafhh  24 hr LCSO 11.4 mslL static. 2SoC   Dave et a1. 1981 
 (Brachvdanio rer!o)            0'\
    48 hr LCSO           CJ'1
    11.4 mgIL sta tio. 2SoC   Dave et al. 1981 
    96 hr LCSO 11.4 mg/L sta tic, 2SoC   Dave et al. 1981 
    144 hr LCSO 11.4 mg/L sta tio, 2SoC   Dave et al. 1981 
    'IT' 13.S mg/L embryo-larval stage  Dave et al. 1981 
      static, 2SOC       
 Golden orfe  LCSO 7.6 ms/L      1unke and Ludemann 1978 
 (Leucisoua ~ melanotus)           
 K:illifish  96 hr LCso 9.6 mg/L static. 2SoC   SasaU et a1. 1981 
 (Orvaias latiuea)            
 Goldfish  96 hr LCsO 8.8 mg/L static. 2SoC   SasaU et a1. 1981 
 (Carasaius auratus)           
 Fa thead minnow  96 hr LCSO 6.4 mgIL      Monsanto 1985a  
 Pimeuhales uromelaa)           
 Rainbow trout  96 hr LCSO 11.0 mgIL      Monsanto 1985a  
 (Salmo .airdneri)            
    48 hr LCSO 14.6 mg/L fry stage. static. SOC Dave et al. 1979 

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    Table 20.~ntinued            
Componnda Species  Lethal ity Concentration  Condi tions   Reference  
    Cd te ri on             
'lBP  Rainbow trout   96. hr LC50 9.4 mgIL    fry stage. sta tic. 5°C 
(Salmo Aairdneri)               
    120 hr LC50 6.8 mgIL fry stage. sta ti c. SOC Dave et a!. 1979  
    48 hr LC50 14.0 mg/L fry stage. static. 10°C Dave et a!. 1979  
    96 hr LC50 11.8 mgIL fry stage. static. 10°C Dave et a!. 1979  
    120 hr LC50 10.5 mg/L fry stage. sta ti c. 100e Dave et a!. 1979  
    48 hr LCSO 12.0 mg/L fry stage. static. Isoe Dave et a!. 1979  
    96 hr LCSO 8.2 mg/L fry stage. static. ISoC Dave et a!. 1979  
    120 hr LC50 7.2 mgIL fry stage. static. ISoe Dave et a1. 1979  
    48 hr LC50 5.0 mg/L fry stage. static. 200C Dave et a!. 1979  
    96 hr LC50 4.2 mg/L fry stage. static. 200C Dave et a!. 1979  
    120 hr LC50 4.2 mg/L fry stage. static. 200C Dave et al. 1979  
    nb 8.3 mg/L embryo-larval stage  Dave et al. 1981  
      static. 80C         
    96 hr LC50 11.5-13.5 mg/LO 20 g size. statio  Dave and Lidman 1978 0"1
            0"1
TOP  Housefly (2-5 d. old) 24 hr LD50 >1000 I1gl jar adul t femal es   Plapp and Tong 1966  
  (Musoa domestioa)              
  Mosquito  24 hr LC50 >1. ppm 4 th instar larvae  Plapp and Tong 1966  
  (Culn tarsal h)              
TIIIIP  Housefly (2-5 d. old) 24 hr LD50 >1000 1181 jar adult females   Plapp and Tong 1966  
  (Musoa domestioa)              
  Mosqui to  24 hr LC50 >1ppm 4 th instar larvae  Plapp and Tong 1966  
  (~ tarsalis)              
1BEP  Fa thead minnow  96 hr LC50 16.0 mg/L sta tio. 22°C   Monsanto 1985a  
  (PimeDhales Dromelas)             
  Housefly (2-5 d. old) 24 hr LD50 >1000 I1gl jar adul t females   Plapp and Tong 1966  
  (~ domestioa)              
  Mosqui to  24 hr LC50 >1 ppm 4th instar larvae  Plapp and Tong 1966  
  (Coin tarsalh)              
TAP  Housefly (2-5 d. old) 24 hr LD50 >1000 I1gl jar adul t females   Plapp and Tong 1966  
  (Musoa domestioa)              
  Mosqui to  24 hr LC50 >1 ppm 4 th instar la~V8e  Plapp and Tong 1966  
  (Culex tarsalis)              
aTBP = tributyl phosphate; TMP = .trimethyl phosphate; TBHP = tri(butoxyethyl) phosphate; TEHP = tri(ethylhexyl) phosphate;
TAP = triallyl phosphate; TOP = triootyl phosphate (CAS No. not given)
b
TT = toxioity threshold. lowest dose reduoing mean survival time

°The nominal conoentration is given in the table; the measured oonoentration ranged from 5-9 mg/L during the tests

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Tab! e 21.
Reproductive Effeotl of Alkyl Pholphatel on EnviroDDental Animal,Speciel
Compo un da
Reference
SpeoiOi
Dose I Route
Effeotl
nIP
TBP
TIP
TAP
.nIP -=
1BP-=
TIP-=
TAP -=
Guppy
(Poec il fa
reticulate)

Toad
(XenoDul ~)
Toad
(XenoDul illW)
Ipermatozoa
Qua il
( Coturnb:
ooturnb:)

( Coturnh:
coturnh:
laDonica)

TWo-lpotted spider mite
(Tetranvohus '
urticae)
TWo-lpotted spider mite
(Tetranvchus
urticae)

TWo-spotted spider mite
(Tetranvchus
urtioae)
TWo-spotted Ipider mite
(Tetranvchus
urtioae)

trJmethyl phosphate
tributyl phosphate
tri(isobutyl) pholphate
triallyl phosphate
2.43 S/L for 100 days
120 ms/mL for 30 minutes
20. 40. 80 msIL
for 0.5. 1. or 2 hours
562 ms/ks to males
by savase
250 ms/ks. 5 daily
oral dose I to males
2.51i
0.1-0.21i
0.1-0.21i
0.1-0.21i
Lou of testicular volullO;
patholosical chansel; no normal
meiotio or post-meiotic cYsts

494ft reduotion in ova under-
soinl cleavase; reduction
in sperm .otility

Followins fertilization with
unezposed ova. furrow inS of
ani.al pole without cleavase
at 40 and 80 ms/'" after
1 hour. and at 20 and 40
ms/'" after 2-hour ezposure

Reduction in ess fertility
Sterile daYI. 10-17 from
firlt dole; alpermic at
day 11 fro. firlt dose

21.31i of ess. hatched compared
with 95.51i of oontrol esss; 10.8
ess. laid oompared to 27.3 for
control.

Nontoxio and no effect on
steril ity
Nontoxic and no effect on
sterility ,
Nontoxic and no effect on
lterility
Kanua 1982
Homsworth and lardhaugh 1978
lone. and Iaokson 1974
Schafer et al. Ig76
Iones et al. Ig72
0\
.....,
PeDDan and O.borne In6
PeDDan and O.borne 1976
,PeDDan and Osborne Ig76
PeDDan and Osborne In6

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~.
Trimethyl phosphate, at 2.5~, also reduced the number of eggs laid and per-
cent hatch of eggs of the two-spotted spider mite, while lower concentra-
tions (0.1-0.2~) of tributyl phosphate, tri(isobutyl) phosphate, and trial-
lyl phosphate had no effect on repioduc~ion (Penman and Osborne 1976).
Trimethyl phosphate also depressed fertilization and the rate of
embryonic development in the plant Niaella damascena (Phan 1976b; Phan and
Andreev 1976). The exact procedures used are not clear. Flowers (140 for
each variant tested) were treated with 0~01~ trimethyl phosphate immedi-
ately after pollination for either 8, 12, or 16 hours. The mean percentage
of seeds obtained from treated seed buds was 15.67 compared to 70.3~ for
controls (Phan 1976b). A mean mutant frequency in the M generation was
5.15 for treated versus 0.12 for control Niaella (Phan t976a). Treatment
significantly retarded the onset of mitosis and prolonged the mitotic cycle
(Phan and Andreev 1976). Chromosome aberrations were examined and the max-
imum number of cells with aberrations was observed 22-28 hours after treat-
ment, but new aberrations were observed up to 80 hours, the maximum period
studied after treatment. Therefore, mutations were induced in almost com-
pletely formed embryos. The maximum number of chromosome aberrations
observed after treatment with trimethyl phosphate was 23.7~. Phan (1976b)
.was also concerned with chlorophyll mutations because their presence may
reflect ability of a mutagen to produce point mutations. Of the five
mutagens studied, trimethyl phosphate induced the fewest chlorophyll muta-
tions (13.22~ ~ 6.59).
4.
Growth and Behavior
Data on inhibition of growth by tributyl phosphate, the only trialkyl
phosphate on which data are available, are given in Table 22.
5.
Abiotic Effects
No data were found~
6.
Other Effects
Several researchers examined .the sublethal toxicity of tributyl phos-
phate.. Playne and Smith (1983) did not observe significant reduction in
gas production by facultatively anaerobic bacteria exposed to tributyl
phosphate in a concentration of 25 ~/mL. Torma and Itzkovitch (1976)
measured a reduction in oxygen consumption in Thiobacillus ferroxidans from
30.47 (control) to 19.64 ~/h per mg protein when grown in medium saturated
with tributyl phosphate. Ennis et al. (1946, as reported in Ross et al.
1979) observed no significant effects on the potato, Solanum tuberosum,
exposed in a spray chamber to a spray of 4~ tributyl phosphate at a rate of
5 mL/sq yard.
Bringmann and Kuhn (1982) determined EC values for immobilization of
Danhnia maana Straus. The ECSO for tributyl phosphate w~s 30 mg/L. The
ECO and EC100 were 5 and 41 mglL, respectively.

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Tabl e 22.
Growth Inhibition by Tributyl Phosphate in Enviroumental Species
Dose
mg/L
Species
Test
Cd terion
Condi tions
Reference
Axenic strains
of 13 algal species

Entosiphon sulcatum

Uronema parduzzi
Chilomonas paramecium
Pseudomonas putida
Scenedesmus quadricauda
Microcvstis aeruainosa
Chlorella emersonii
ChIarella emersonii
14 day EC100 a
1T>
1T>
nb
TTb
TTb
TTb

EC50

EC50
25-2.100
Blanck et al. 1984
sta tic, 20°C
14 static, 25°C Bringman and Kuhn 1980 
21 sta tic, 25°C Bringmann and Kuhn 1981 
42 sta tic, 25°C Bdngmann and Kuhn 1981 
>100 sta tic, 25°C Bringmann and Kuhn 1980 
3.2 sta tic, 270C Bringmann and Kuhn 1980 
4.1 sta tic, 270C Bringmann and Kuhn 1978 
10-50 inhibition during Dave et a!. 1979 
 exponential growth, 2980K   
5-10 2980K, standing Dave et 81. 1979 '"
1.0
 stock a t 48 hr     
 detectable      
 inhibition of     
a
14 day EC100 = Lowest concentration giving no
Arowth after 14 days. .
TT = toxicity threshold, lowest dose yielding
growth.

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70
F.
Standards, Regulations and Recommendations
3The current OSH~ standard for tributy1 ph?sphate is an average of 5
mglm measured over an8-hour work shift (Mack1son et a1. 1981). The ACGIH
has ~ecommended that the ThJesho1d Limit Value (TLV) be reduced from 5
mglm (0.4 ppm) !o 2.5 mglm (0.2 ppm)with a short term exposure limit
(STFL) of 5 mglm (0.4 ppn) (AOOIH 1984).
G.
Other Relevant Information
Two tria1ky1 phosphates not covered in this report, triethy1 phosphate
and triocty1 phosphate (1806-54-8), were tested for mutagenicity inSa1-
mone11a strains TAlOO, TAl535, TAl537, and TA98, and were negative with and
without metabolic activation (NTP 1985). .

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71
II.
Ref erence s
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72
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75
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90
B.
Supplemental Information
The following organizations responded to the Agency's request for
information on trialkyl/alkoxy phosphates for this Chemical Hazard Informa-
tion Prof it e:
Submitter Name: V.A. Fung. National Toxicology Program
EPA Document Control Number: FYI-OTS-0385-0380 FLWP. Seq. B
Information Types: Genotoxicity data for tributoxyethyl phosphate.
triethylhexyl phosphate. triethyl phosphate. and
trioctyl phosphate (CAS No. 1806-54-8)~ Carci-
nogenici ty bioassay resut ts for trimethyl phos-
phate and triethylhexyl phosp~ate. .
Submitter Name: National Institute of Occupational Safety and Health
EPA Document Control Number: FYI-OTS-0385-0380 FLWP. Seq. C
Information Types: NIOSH TIC database print~ut
Submitter Name: Rohm and Haas Company.
EPA Document Control Number: FYI-OTS-0385-0380 FLWP.. Seq. D
Information Types: Material safety data sheet
Toxicity summary from open literature
Submitter Name: Olin Chemicals Group
EPA Document Control Number: FYI-OTS-0485-0380 FLWP. Seq. E
Information Types: Letter to T. O'Bryan stating that the Brandenburg
facility has no unpublished information on tri-
alkyl/alkoxy phosphates
Submitter Name: Monsanto Industrial Chemicals Co.
EPA Document Control Number: FYI-OTS-0385-0380 FLWP. Seq. F
Information Types: Letter from H.M. Keating (4/4/85) containing
. mo~itoring data and information on euvironmental
fate and uses of tributoxyethyl- and tributyl
phosphates; material safety sheets for
tributoxyethyl- and tributyl phosphates; acute
toxicity studies in fish and mammals; and irri-
tation studies in humans
Submitter Name: Monsanto Indust~ial Chemicals Co.
EPA Document Control Number: FYI-OTS-038S-0380 FLWP. Seq. G
Information Types: Corrected copy of letter from H. JL Keating
. (4/5/85) regarding uses of tributyl- and
tributoxyethyl phosphate
Submitter Name: Eastman Kodak Co.
EPA Document Control Number: FYI-OTS-0385-0380 FLWP. Seq. H
. Information Types: Letter from L D. Gerwe (April 19.1985) stating
that Eastman has no ~nformation on trialkyl
phosphates other than that for TEP which was
previously submitted to USEPA.

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91
Submitter Name: FMC Corporation
EPA Document Control Number: FYI-OTS-058S-03805 Follow-up, Seq. I
Information Types: Acute oral, dermal, and inhalation toxicity studies;
eye and skin irritation studies; 13-week toxicity
studies (published and unpublished); and a genotoxicity
study, all on butyl phospha~e.
Submitter Name: Confidential Business Information (CDI)
EPA Document Control Number: FYI-OrS-0585-0380 S Follow-up, Seq. J
Information Types: CDI production/use information on tributyl and
tributoxyethyl phosphates
Submitter Name: E.I. du Pont de Nemours 'Co.
EPA Document Control Number: FYI-OTS-OS8S-0380 FLWP, Seq. K
Information Types: Physical/chemical properties and production data
for CAS Nos. 57344-10-1 and 57344-02-2

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92
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BACK66   0 0 0 0 0 0 0 
DIALOG           1.0
BIOSIS PREVIEWS 69-76 3 1 0 19 55 0 0 .. .......
BIOS IS PREVIEWS 77-80 2 2 0 16 43 0 1 .. 
BIOSIS PREVIEWS 81- 3 10 0 29 47 0 0 .. 
Chemical Ezposure 74- 0 0 0 0 0 0 0 .. 
Congressional Records Abstracts 77- 0 0 .0 0 0 0 0 .. 
Federal Register Abstracts 76- 1 0 0 0 2 0 0 .. 
Federal Research in Progress 8~- 0 0 0 1 2 0 0 .. 
NTIS 64-  4 0 0 191 13 0 0 .. 
CAS Onl ine  188 128 78 210. 85. 23 0 100 
Registry Fil e           
.DIALOG CA files searched; limited. ..Not searched. no hits in CAS Online     

-------
  Databases Searched     
Da taba se 4200-55-9 4889-45-6 6163-73-1 7332-46-9 10427-00-6 56827-95-3 57344-01-1 5734-02-2 
MEILARSII         
1'OXLINE 79- 2 0 1 0 0 1 0 0 
TQX76 1 0 1 0 0 1 0 0 
1'OX65 0 0 0 0 0 2 0 0 
CANCERLINE 0 0 0 0 0 1 0 0 
CANmRPROJ 0 0 0 0 0 0 0 0 
CUE" INE 1 1 1 1 1 1 1 1 
R'mCS 0 0 0 0 1 0 '0 0 
TDB 0 0 0 0 0 0 0 0 
MEILINE 0 0 0 0 0 1 0 0 
BACKSO 0 0 1 0 0 1 0 0 
BACK77 0 0 0 0 0 1 0 0 
BACK75 0 0 0 0 0 1 0 0 1.0
BACK71 0 0 0 0 0 0 0 0 00
BACK66 0 0 0 0 0 0   
DIALOG         
BIOSIS PREVIEWS 69-76 0 0 0 0 0 0 0 0 
BIOSIS PREVIEWS 77-80 0 0 0 0 0 0 0 0 
Chemical Exposure 74- 0 0 0 0 0 0 0 0 
Consressional Records Abstracts 77- 0 0 0 0 0 0 .0 0 
Federal Resister Abstracts 76- . 0 0 0 0 0 0 0 0 
Federal Research in Prosress 82- 0 0 0 0 0 0 0 0 
NTIS 64- 0 0 0 0 0 0 0 0 
CAS Onl i ne 30 12 4 8 7 6 1 1 
Resistry Fil e         

-------
    Databases Searched     
Da ta ba se   64131-07-3 64131-08-4 64131-09-5 64131-10-8 64131-18-6 64502-13-2 73070-47-0 74049-24-2 
MEILARSII           
TOXLINE 79-   0 0 0 0 0 0 0 0 
TOX76   0 0 0 0 0 0 0 0 
TOX65   0 0 0 0 0 0 3 0 
CANCERLINE   0 0 0 0 0 0 0 0 
CANCERPROJ   0 0 0 0 0 0 0 0 
CBIM.INE   1 1 1 1 I I I 1 
R'mCS   0 0 0 0 0 0 0 . 0 
TDB   0 0 0 0 0 0 0 .0 
MEILINE   0 0 0 0 0 0 0 0 
BACK80   0 0 0 0 0 0 0 0 ~
BACK77   0 0 0 0 0 0 0 0 ~
BACK75   0 0 0 0 0 0 0 0 
BACK71   0 0 0 0 0 0 0 0 
BACK66   0 0 0 0 0 0 0 0 
DIALOG           
BIOSIS PREVIEWS 69-76  . . . . . 0 0 0 
BIOS IS PREVIEWS 77-80  . . . . . 0 0 0 
Chemical Exposure '74-  . . . . . 0 0 0 
Congressional Records Abstracts 77- . . . . . 0 0 0 
Federal Register Abstracts 76- . . . . . 0 0 0 
Federal Research in Progress 82- . . . . . 0 0 0 
NTIS 64-   . . . . . 0 0 0 
CAS Online   0 0 0 0 0 1 0 2 
Registry Fit e           
.Not searched. no hits in CAS Online.         

-------
100
3.
Search Strategy
The databases were searched on the basis of CAS No.. chemical name.
and synonyms as listed in CHEMLINE. The Chem Abstr files for trimethyl
phosphate and tributyl phosphate were limited to non-patent references; all
other fil es were" dumped" and scanned for pertinent reference s.
D.
Chemical Specific Secondary Sources Searched
Brandrup J. Immergut EH.
Publ ishers.
1966.
Polymer handbook. New York:
Interscience
Browning E. "1965. Toxicitr and metabolism of industrial solvents.
York: Elsevier Publishing Company.
New
Englund A. Ringen K. Mehlman MA. 1982. Advances
toxicology. vol 2: Occupa Honal heal th hazards of
Princeton Scientific Publishers Inc.
in modern environmental
solvents. Princeton. NT:
Frados J. ed. 1976. Plastics engineering handbook. 4th ed.
Van Nostrand Reinhold Co.
New York:
Lefaux R.
Press.
1968.
Practical toxicology of plastics.
Cleveland. OR:
CRC
Mellan I. 1977. Industrial solvents handbook. 2nd ed.
Noyes Data Corporation.
Park Rid.ge. NT:
Overcash MR. ed.
pounds in soil s.
1981. Decomposition of toxic and nontoxic organic com-
Ann Arbor. MI: Ann Arbor Science.
Plastics International.
materials and processes.
1963. An industrial guide and catalogue of plant.
London: Temple Press Books.

-------
APPENDIX A
Chemical Identity, Physical and Chemical Properties
and
Production, Exposure, and Uses Data.
f~
Minor Tri(alkyl/alkoxy) Phosphates

-------
Table 1.
Phyaical , Chemical Proper tie a aad ~aare Data for Kiaor Tri(alkyl/alkozy) Pholphatea
A.
Chemical Ideatity
1.
CAS Reliatry Namber
126-71-6
2.
Chemical Nue:
Phoaphoric acid.
tril(1-aethylpropyl)
eater
3.
Syaoay.a:
Phoaphoric acid.
triiaobatyl eatera
4.
OBu -i
i -euOPOBu-;
o
Stractaral foraala:
5.
C12~704pa
Koleoalar foraa~a:
B.
Phyaical aad Cheaical Propertiea
1.
Moleoalar .eilht:
166.31
2.
Phyd cal ata te:
Not foaad
3.
Keltial POiDt (OC):
Not foaad
4.
264d
Boilia, POiDt (OC):
5.
Solabilitiel fa
Aqaeoaa:
Solabled
Noa-aqaeoaa:
Solable ia alcshol.
ether. beaseae
6. Di noct ~ ti oa ooaataat:
7. DeDd ty:  
8. Volatility:  
9. Other  
 a. Rof raot 1"0 IDde.:
Not foaad
0.9681 at 20lCd
Not foaad
1.4193 at 200Cd
b. PartitioD coefficieDt
(101 P) ootaDol/.ator:
cyclohe.aDe/.ater:
10. Reactivity: ID aoldic aolatioD. all phoaphate
.olutloa oDly trialkyl phoaphatea are hydroly.ed by the
heated to the poiat of deooapoaitloa. trl(alkyl/alko.y)
phate caD eaplode oa diatillatloa (Sa. 1984).
Not foaad
eatera are
r_oval of
phoapha te a
512-56-1
Phoaphoric aci d.
triaethyl eater
Kethyl phoaphate;
Trlaethoayphoaphlae oalde;
Triaethyl orthophoarhate;
Triaethyl phoaphate
OM,
MIOPOMI
o
a
C3\04P
140.08
Colorleaa liqaidb
-46 (po.. pofaUo
197.1c
100 parta ia 100
parta .ater at 151Ce

Solab~e ia laaoliae:.
ether. aad alcohol
Not foud
1.197 at 19.5IC.
1.1144 at 20'Cd
Not foaad
1.397 at 200cb
1613-19-4
Phoaphoric aoid.
tri-1-propeayl eater
Allyl phoaphate;
Phoaphoric aold.
trhllyl eater;
Triallyl orthophoafbat.;
Trhllyl pholphate
OCH,CH:CH,
H,C:CHCH,OPDCH,CH:CH,
o
a
C9H1504P
118 .19
Water-whit. liqaidb
< -50b
80 at 0.5 .. Rib
Not foud
Not foaad
Not foaad
1.064 at 251Cb
Vapor prell..e: b
0.5 .. HI at 80lC
1.448 at 2,Icb
-O.1Sf
-2.221
readily olea"ed to pboaphoric acid. bat iD alkaliD.
oaly ODe alko., Iroap (KorrlaoD aDd Boyd 1973). Whea
ealt toslo fDII.a of POa (Sa. 1984). Triallyl pboa-
Not fODDd
4100-55-9
Phoaphorio aold.
trll(decyl) .Iter
Pholphorlc lcid.
tridecyl eltera
DICH,J,Me
MeICH,I,OPDICH,I,M,
o
a
C30H6304P
......
o
N
518.80
Not foaad
Not foaad
Not fODDd
Not foaad
Not f oaad
Not foud
Not foud
Not foud
Not fOUAd
Not foaad .

-------
C.
126-71-6
Hzposure
1.
10-101h
(Appareatly all
I.ported)
Table 1.
Continued
1623-19-4
No da ta
Bor,-'araer~P)
SartC8u(P)
(1) Phosphorus ozy-
chloride + correspoad-
ID' allfhatlc alcohol
with I, + as catalYlt
oODtrolled tr.peratare
aad prenure

(2)loaotlon of PCI3
with allyl alcohol la
the preloace of tert-
Iary ..Iae. thon ozl-
dlaed by :Ir to the
pholphate
Ca talYltl. adhell oa
prC8oter9. labrl-
oatln, oil addltlvel0.
filler for artificial
bODel aad teeth
No data were fOllDd
Probably IIDderf~es
blod.,radatioa
4200-55-9
110-1100h
lor,aaton (10-100)(P)
Lubrlaol Corp. (No
data)(P)
DSM-USA (100-1.000)(I)h
(I) Phoaphorua oxy-
chloride + correlpoad-
la, allftatlo alcohol
with I, al catalyat
coatrolled tr.peratare
aad prealare
Major UIOI ladlcated by
patenta: eztractlon
lolveat. atabillaer
for pl..eata. peaetraat
for Jood-plaat herbi-
cide .
.......
C>
W
1977 Produotloal
I.por ta ti fa
(Lba z 10 )
2.
Produoeu (PH
l.porteu3 (I)
(Lba z 10 )
RASF 'yaadotte (10-100)(1)
lor,aatoa Plaat (0-1)(1)
A.erloan foechat Corp. (I)
(No data)
512-56-1
10-101h
Ualdeatlfled (0-1)(1)
Stauffer(I~100)(P)
FUo (0)(1)
(I) Pholphorul oxy-
chloride + correlpoad-
la, allftatlc alcohol
with I, al catalYlt
coatrolled tr.perature
aad prenare
Dye cC8poaltlon addi-
tive. ablolaalon In-
ducer; pol,...rlaa-
tlon oataly.t. lubri-
catln, 011 addlt~vJ .
alkylatln, a,eat' In
preparatio, of
DIchlorvtl . lalollne
additive. catalyat
for pollelter .anu- .
facture. fl..e re- 7 8
tardaat la pol,..erl. .
No data wer. fODDd
Bydrolytl!4half-Ilfe.
1.2 yearl . 1
Probably blode,raded 3
No data were fOllDd
Probably IIDderf~ea
blode,ndation
3.
Production Methodl
(I) PhOlphOruS ozy-
chloride + correapoad-
la, allftatlc alcohol
with II al catalYlt
controllrd te.perature
preslnre
4.
Unl
Corrollon Inhibitor.
peltlclde Interaldlate.
antistatic a,eat
5.
Monl toria, Da ta
'orker aad coalU8er
ezpolare data not
fOllDd. Deteoted In
,rollDdwater la the
NetherlaDdl (.,t.
conc. 10 p,/L)
6.
Buv ho_ontal
Fate
Balf-llfo In 'I~DDd-
water. 1.2 .oa .
Probably blode,raded13

-------
Table 1.
Continued
A.
Chemical Identity
, 1.
CAS Beailtry Number
9111-111-0
3033-37-1
, 48811-45-6
6163-73-1
1.
Cheaical Name:
, I-Butanol. 3-aethyl.
pholphate (3:1)(IICI)
Tridecanol.
pholphate (3:1)(8CI)
Pholphoric acid.
trioctadecyl eater (IICI)
Ethanol. 1-8Ctho~.
pholphate (3:1)(IICI)
3.
Synonym I :
PhOlphOriC acid.
triilopentyl elter (8CI)a
None I htod
None I hted
None Hlted
 4. Strnctural formula: ' OCH2CH2CHMI2 01 CH2'.2.1 DC CH2'.7" OCH2CH2OMI 
 .12CHCH2CH20f,OCH2CH2CHMI2 .ICCH2'.20f,0ICH2'.2.1 .11 CH2'.70POI CH2'.7" MoOCH2CH20POCH2CH2OMI 
       ,.. 0 
       0 0 0 
 5. Molecular ,formula:  C15H3304pa a a a 
  , C31111s104P C54HUI04P Cg~107P 
           ......
B. PhYlical and Chemical Propertiu     a
     ~
 I. Molecular weiaht:  308.40 645.05 855.45 171.14 
 1. Physical Ita to:  Not found Not found Not found Not found 
 3. Meltins point (IC): Not found Not found Not found Not found 
 4. Boil ina Point ("C): Not found Not found Not found Not found 
 5. Solabil it ~ ea in      
   Aqueoul:   Not found Nct found Not found Not found 
   Non-aqueoul:   Not found Not found Not found Not found 
 6. DillochUon constant: Not found Not found Not found Not found 
 7. Density:   Not found Not found Not found Not found 
 8. Vol aU H ty:   Not found Not found Not found Not found 
 II. Other       
  I. Refractive iudes: Not found Not found Not fcund Not found 
  b. ParU tion coefficient: Not found Not found Not found Not found 

-------
   Tabl e 1. Continued.  
   91!1-62-0 3033-37-2 488!1-45-6 6163-73-1
c. Exposure    
 1.. 1!177 Produotionl No da ta 10-100 0 No data
  IaportatiJn    
  (Lbs x 10 )    
 2. Prodllcersl Stauffer LP) Stauffer 01 in (P) Stauffer (P)
  I.porteu3 (No da ta) (10-100) (p)h  .(No da ta)h
  (Lbs x 10 )    
 3. Prodllction Methods  No da ta Has been prepared No da ta
   (1) Phosphorlls oxy-  fr08 trioctadeoyl 
   chloride + correspond-  iodide an1 silver 
   ina aliftatic alcohol  phOlpha te 
   with la as catalyst,   
   controlled tr.perature   
   and prellure   
......
o
(J'1
4.
Uses
No infor8ation to indicate
.ajor IIses . A .inor IIse
..y be in the preparation
of aelatin-free dispersiYJs
of photolraphic additive
No infor8ation to
indicate .ajor IIsesl
No infor8ation to
indicate .ajor IIsesl
No infor8ation to
indica te .aj or use sl
5.
IIonitorina Da ta
No data were fOllDd
No data wne fOllDd
No da ta wen f ollDd
No data were fOllDd
6.
Bav fro_ental
Fate
Probably IIDderfJes
biodeandation
Probably IIDderfJ.s
biodeanda tion
Probably IIDderfJes
biode.radation
Probably IIDderfJ.s
biodeanda tion

-------
A.
B.
Che8ical IdeDtity
1.
CAS Reliltry Number
2.
Chuical N..e:
3. . SYDoDyml:
7332-46-!I
BthaDol, 2-(2-buto~
ethory)-, pholphat; (3:1)
(!lCI)
NODe lilted
Table 1. CoDtiDued
10427-0~6
2-Furaa.ethaDol, tetra-
hydro-, pholphate (3:1)
(!lCI)
Furfuryl alcohol,
tetrahydro-, .pholphate
(3:1) (BCI)
qo
CHi
;,
6- CH.O~OCH. -()

C15H2707P
4.
OCH.CH.OCH.CH.OI CH.I,III
Struotural foraula: llel CH.IIOCH.CH.OCH.CH~OPOCH.CH.OCH.CH.OI CH.I,III
o
5.
JIoleoular foraula:
PhYlioal aDd Chemioal Propertiel
1.
Moleoular weiaht:
2.
Physioal atate:
3.
MeltiDI point (IC):
4.
BoiliDI PoiDt (IC):
5..
Solubilitiel iD
Aqueoul:
Non-aqueoul:
6.
DilaooiatioD coDltant:
7.
DODlity:
8.
Vola ti li ty:
9.
Other
a.
Refractive indo.:
PartitiOD coefficient:
b.
C24H5101oP
530.64
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
350.35
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
56827-95-3
I-Heodecanol,
pholpha te (3: 1)
(!lCI)
None lilted
01 CHal 'Ille
1111 CH.I "OPOC CH.I. ,lie
o
C4B~!l°4P
771.2!1
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta
No data
No da ta
No da ta
64131-07-3
I-HeooolaDol,
pholphate (3:1)
(!lCI)
NODe 1 ilted
OC CHa1n1l1
IIIICHal.80f.01 CHal a 8111
o
C78H15!1°16P
......
o
0\
1192.10 .
No da ta
No da ta
No da.ta
No data
No da ta
No da ta
No da ta
No da ta
No da ta
No da ta

-------
   Table 1.. Colitinued  
   7332-46-9 10427-00-6 56827-95-3 64131-07-3
C. Eaposure     
 1. 1977 Produotionl No 4atah I-lob Oh Oh
  lapor ta ti on     
  (Lba a 103)     
 2. Produoenl ICI AIIericu (P) Arol Chemical 01 in (p)h Olin (p)h
  Iaportera  U-l0)h  
  (Lba a 103)     
 3. Production Methoda No 4a ta No 4a ta Baa been prepared No 4a ta
      by the eaterification 
      of phoaphorio acid 
      with alkylha1iduj 
......
C.
""'-I
4.
Uses
No infor8atioD found
to indicate .ajor uaeal.
MiDor uaea .ay iDolDde:
iD polymerio reaina16.17
aDd iD floor cleaniDI
and poliahin, aleDta 8.19.
aa aDtifoa.in, alent iD
aluaina .annfaoture20
No infor8ation found
to iDdicate .ajor uaeal
No infor8ation found
to iDdicate .ajor uaeal
Minor uaea .ay iDolude:
-anti.tatio aleDt for
ther8oplaatic.21.
in liquid cryatal
display ce11.22.
to iaprove re.i.taDt
qualitie. of poly-
viDTl chloride fil..23
No infor8aUoD found
to indicate ..jor u~esl
5.
JIonitorinl Da ta
No 4ata wen found
No 4a-ta were found
No 4a ta were found
No 4ata were found
6.
BDvirouaental
Fate
Probably underfoe.
biodelra4ation 3
Probably underfoe.
blodeln4ation 3
Probably under,oe.
biodelra4ation13
Probably underfoe.
biodelra4atioD 3

-------
Table 1.
CoDthuod
A. Chomi cal IdoDti ty     
 1. CAS Reliatry Numbor 64131-08-4 64131-09-5 64131-10-8 64131-18-6 
 2. a.-ical Naae: I-TotracoaaDol. I-DocoaaDol. I-BicolaDol. 1-0ctacolaDol.
     phuphato (3: 1) pholphato (3:U phoapha to (3: U. . phoaphato (3: 1)
     (9CI) (IICI) (9CI) (9CI) 
 3. SYDoDyma:  NODo lilted No DO li lted NODO liated . No DO liated
 4. Structural foraula: DC CH.lu'" DC CH.' ..'" ~eCH.I,I,," DC CH.» .,... 
 ...eCH.'..Of-OCCH.'..". ...eCH.I..OPOCCH.»..", ...eCH.I.I0r,oeCH'».I'" ...(CH.I"0f,0ICH.I",," 
         ° 0 ° ° 
 5. Moleoular foraula:  C72B14704P C66B13504P C6oRl2304P Gl4B17104P 
             -
B. Phyaical IDdChnical ProporU 01     a
    00
 1. Moleoullr woiaht:  1107.94 1023.78 939.61 1276.26 
 2. Phyaical a ta to :  Not found Not found . Not found Not found 
 3. lie 1 ti DI poht ("C): Not fouDd Not found Not fouDd Not found 
 4. BoiliDI Polut (OC): Not fouDd Not found Not found . Not found 
 5. SolubiliUn h      
   AquoOUl:   Not found Not found Not found Not found 
   NOD-aquooua:   Not found Not found Not found Not fouDd 
 6. Dh,oohUOD OODltaDt: Not found Not found Not found Not found 
 7. DoDIUy:    Not found Not found Not found 
 8. Volatility:   Not fouDd Not fouDd Not found Not found 
 II. Otbor       
  a. Rof ract i vo i Ddo.: Not found Not found Not found Not found 
  b. PartitioD coofficioDt: Not fouDd Not found Not found Not found 

-------
    Tablo 1. CoDtiDued  
   64131-08-4 64131-09-5 6~131-1o-8 64131-18-6
c. Bspo811re     
 1. 1977 ProductioDI 0 0  0 0
  Iapor ta ti JD     
  (Lb. S 10 )     
 2. Producersl 01 h (p)h 01 h (p)h 01 iD (p)h 01 iD (p)h
  Iaporters     
  (Lbs S 1(3)     
 3. ProductioD Jlethod. No. data No da ta No da ta No da ta
.....
a
\0
4.
Use8
No iDfo1'llaUoD fOUDd
No iDfonsaUoD fOUDd
No iDf onsa ti OD f oUDd
No iDfonsatioD fOUDd
5.
IIoDi todD, Da ta
No data were fOUDd
No data were fOUDd
No data were fOUDd
No data were fOUDd
6.
BDV iroD8ental
Fate
Probably UDderfoe8
.biode.radatioD 3
Probably UDderfoes
biode.radatioD 3
Probably UDderfoes
biode.radatioD 3
Probably UDderfoes
biode.radatioD 3

-------
Table 1.
Contln~
A.
Chemical Identity
1.
CAS ReSistry Number
64502-13..,2
7307H7-0
74049-24-4
2.
Chasical Name:
POly(0zy-l.2-ethanediyl).
. alpha.. . alpha. '.. alpha. ' '-
phosphinylidynetris(.08eSa.-
hydrozy- (9C1)
POly(ozy-l.2-eth8nediyl).
.alpha...alpha.'..alpha."-
phophinylidynetris(.08e.a.-
(tridecylozy)- (9CI)
Poly(0zy-l.2-ethanediyl
.alpha.. .alpha.'-(methozy-
phosphinylidyne)bis-
. O8esa. -hydrozy- (9CI)
3.
Synonyms:
None listed
None 1 h ted
None 1 hted
4.
Structural foraula:
Not found
Not found
Not found
 S. Molecular foraula:  (C2B40)mult-(C2B40)ault- (C2B40)aul t-(C2B40)aul t- (C2B40)aul t-(C211.4°)aul t- 
       (C2B40)mul t-B304P (C211.4°)81I1 t-C39Bal04P mSo4P 
B. Physical and Chemical Properties    
 1. Molecular weight:  )230 )777 )200 ~
  ~
          o
 2. Phydcal state:  Not found Not found Not found 
 3. lie 1 tinS point (ec): Not found Not founel Not founel 
 4. BoU In. Point (ec): Not founel Not founel Not founel 
 5. Solubilities In     
   Aqueous:   Not founel Not founel Not founel 
   NOlraqueous:   Not founel Not founel Not fOUlld 
 6.. muochtion constant: Not founel Not founel Not founel 
 7. Dend ty:   Not founel Not founel Not founel 
 8. Vola tU ity:   Not found Not found Not founel 
 9. Other      
  a. Ref ra cti ve hder: Not found Not founel N~t found 
  b. Partition coefficient: Not found Not founel Not found 

-------
   Table 1. Continued  
   64502-13-2 . 7307H7-0 74049-24--4 
c. B.zpoaaze    
 1. 1977 Produotionl No reoord o-lh No da ta 
  Importation    
  (Lbl J: 103)    
 2. . Produoenl No da ta Arol Che.ioal (o-l)(p)h Amerioan Boechlt Corp. (I)h
  Illporten    
  (Lbl J: 103)    
 3. Produotlon Methodl No de ta No da ta No da ta 
4.
Usel
,......
....
....
No laforaation found
to Indicate .ajor Ulel.
No laforaatlon found.
to indioate .ajor ulel.
No laforaatlon found
to Indicate .ajor U80I.
5.
IIonitodnl Data
No data were found
No da ta we re found
No data were found
6.
Bavlro_ental
Fate
Probably underfoe,
blodelradatlon 3
Probably underfoe,
biodelradatlon 3
Probably underfoe'
blodelradatlon 3

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112
F001NOTES FOR TABLE 1
Footnotes for Chemical Identity and Physical and Chemical Properties
:MEILARS II (CHEMLINE) 1985
Hawley 1981
c
~andmeyer and Kirwin 1981
-Weast et ale 1984-85
e
fDean 1979
Jaw and Hansch (unpublished. as reported in Pomona College 1984)
~olfenden and Williams 1983
-:USEPA 1983
1 .
Fernanda et ale 1972, as reported in Chem Abstr 79:91S82m
~omez and Sutaria 1974. as reported in Chem Abstr 85:1082S2c
fBloecker et ale 1980, as reported in Chem Abstr 94:17046h
Mitsui 1981, as reported in Chem Abstr 96:8507Sh
~odan and Baranaukas 1964, as reported Beacham 1978
Footnotes for Production, Exposure, Uses
~SEPA 1985
3Hinkamp and Warren 1958, as reported in NCI 1978
4Fi shbein 1979
,Martin 1968. as reported in Fishbein 1979
6Ehrenberg et ale 1974. as reported in Fishbein 1979
7Watanabe et ale 1973, as reported in Fishbein 1979
8M&tsunaga et ale 1975, as reported in NCI 1978
9 Well 1980
10Mowdood and Maxey 1982, as reported in Chem Abstr 98:736828
11Ashkinazi et ale 1983, as reported in Chem Abstr 99:215514a
12Tsunekawa et a1. 1982, as reported in Chem Abstr 98 : 546S4h
13Zoetman et ale 1981
14Radding et ale 1977
15Mabey and Mill 1978
, 16Seifert et a1. 1983, as reported in Chem Abstr 1983
17Warshawsky et a1. 1979. as r,eported in Chem Abstr 91: 58266m
18Warshawsky and Patchornik 1978, as reported in Chem Abstr 91:74510"
19Mizutan! et ale 1977, as reported in Chem Abstr 88:63522j
20Lima and Hopper 1969. as reported in Chem Abstr 71:72082s
21A1ufab 1973. as reported in Chem Abstr 80:72535c
22Vasilenok et ale 1976, as reported in CAS Online CA85:47472a
23Canon 1982. as reported in Chem Abstr 99:222497a
Achilles Foam Board Co., Ltd., as reported in Chem Abstr 99:141040u

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113
. PRomcrION/USE/EXPOSURE INFORMATION m MINOR TRIALKYL/ ALKOXY PHOSPHATES
Phosnhoric acid, tris(1~methv1nronv1) ester (126-71-6)
Synonym: Triisobuty1 phosphate
. .
A review of the production range (includes importation volumes)
statistics for triisobuty1 phosphate (CAS No. 126-71-6) which is listed
in the initial pub1!c (non-CDI) TS~ Inventory (USEPA 1983), has shown
that between 1 x 10 and 1.01 x 10 pounds of this chemical were
.
reported as produced/imported in 1977. According to the public, non-
confidential file of the TSCA Inventory (USEPA 1983), three U.S. com-
panies imported triisobuty1 phosphate in 1977. No companies were listed
as producers of the compound in the TSCA Inventory and there was no evi-
dence in Chem Sources (1982) or in the Directory of Chemical Producers
(SRI 1984) to indicate that the compound is currently produced in the
U. S.
Monitoring data to document worker and consumer exposure to triiso-
butyl phosphate were not found.
The major uses of triisobuty1 phosphate suggested by patents
include those of corrosion inhibitor, pesticide intermediate, and antis-
tatic agent (USEPA 1985). Therefore, the manufacturing and use of pes-
ticides, and the application of corrosion inhibitors and antistatic
agents could be potential sources of worker exposure to the compound.
Patents were found for other applications of the compound in the
preparation of powdered alkali blue pigments (Iyengar and Jesse 1984, as
reported in Chem Abstr 101:132579j); in the production of a glass-like
material (G1iemeroth et a1. 1984, as reported in Chem Abstr 101:42486x);
as an additive in plaster to impart rapid ~igh strength (Grad1 and Bey-
mer 1977, as reported in Chem Abstr 88:11067v); and as a solvent for
protective impregnation of wood with fungicides (Reuther et a1. 1970, as
reported in Chem Abstr 73:111155f); however, there is no evidence that
these are significant commercial uses. Triisobuty1 phosphate has also
been tested for use as an extractant in reprocessing spent nuclear reac-
tor fuel (Rozen et a1. 1984, as reported in Chem Abstr 101:45138w). .
Zoetman et a1. (1981) identified triisobuty1 phosphate in contam-
inated groundwaters in the Netherlands at a maximum concentration of 10
~g/L. This suggests that the compound, being water soluble (Weast et
a1. 1984-1985), can be transported through the soil and may persist, to
some extent, as an aquatic pollutant. The estimated half-life for tri-
isobutyl phosphate in groundwater.is approximately 1.2 months (Zoetman
et a1. 1981). The route of degradation in this instance was not clearly
. This production range information does not include any
production/importation data claimed as confidential by the ~erson(s)
reporting for the TSCA Inventory, nor does it include any information
which would compromise Confidential Business Information. The data
submitted for the TSCA Inventory, including production range
information, .are subj ect to the 1 imi ta tions contained in the Inventory
. Reporting Regulations (40 CPR 710).

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114
indicated. Information on the degradation of other phosphate esters
suggests that, if released to.the environment during its production or
use, triisobutyl phosphate would be 1 ikely to undergo biodegrada tion,
but would probably be stable to direct photolysis and chemical oxidation
(Saeger et al. 1979; Radding et al. 1977).
Phosuhoric acid, trimethvl ester (512-56-1)
Synonym: Trimethyl phosphate
A review of the production range (includes importation volumes)
statistics for trimethyl phosphate (CAS No. 512-56-1) which is listed in
the initial pu~lic (non-CBI) }SCA Inventory (USEPA 1983), has shown that
between 1 x 10 and 1.01 x 10 pounds of this chemical were reported as
produced/imported in 1977. (See footnote, page 113.)
According to the public, non-confidential file of the TSCA Inven-
tory (USEPA 1983), three U.S. companies produced/imported the chemical
in 1977. In 1978 ~t was reported that trimethyl phosphate was still
available commercially, but was no longer manufactured in the U.S. (Chem
Sources-U.S.A. 1977, as reported in NCI 1978).
Monitoring data documenting worker, consumer and environmental
exposure to trimethyl phosphate were not found. Manufacturing processes
for phosphate esters appear to be contained in closed systems (Fernanda.
et al. 1972, as reported in Chem Abstr 79:91582m; Arct 1975, as reported
in Chem Abstr 83:163757e; USEPA 1985) indicating minimal worker exposure
during production. HOwever, as with other phosphate esters (USEPA
1985), worker exposure to trimethyl phosphate could occur during the
transfer and packaging or drumming of the compound.
The major uses of trimethyl phosphate suggested by patents include
those of dye composition additive, abscission inducer, polymerization
catalyst, and lubricating oil additive (USEPA 1985). Trimethyl phos-
phate is also used as an alkylating agent (Hinkamp and Warren 1958, as .
reported in NCI 1978; Fishbein 1979); in the preparation of the insecti-
cide, Dichlorvos (Martin 1968, as reported in Fishbein 1979); as a gaso-
line additive (Ehrenberg et a!. .1974, as reported in Fishbein 1979); as
a catalyst for polyester manufacture (Watanabe et al. 1973, as reported
in Fishbein 1979); and as a flame retardant in polymers (Matsunaga et
al. 1975, as reported in NCI 1978; WeU 1980). The compound is patented
for use in the treatment of polyethylene containers to enhance storage
stability of a-cycanoacrylate adhesive (Takaoka Chemical Mfg. Co., Ltd.
1983, as reported in Chem Abstr 100:211222v) and has been proposed for
use as a stabilizer in the processing of polyethylene phthalate polymers
intended for food contact .(FDA 1980a, 1980b) (Sungkong Fibers Ltd. peti-
tioned the FDA to allow the use of trimethyl phosphate for this purpose.
The petition ~as later withdrawn by the company [FDA 1980b).
If released to the environment during its production or use,
trimethyl phosphate would likely undergo biodegradation, but would prob-
ably be stable to direct photolysis, hydrolysis and chemical oxidation
(Radding et al. 1977). The rate constant for the reaction of trimethyl

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115
phosphate with HO radical has been estimated to be <1 % 10-9 (Mrls-1)
with a half-life of >230 hours (Radding et a1. 1977); the rate constant
for hydrolysis has been estimated at 1.8 x 10-8 with a half-life of 1.2
years (Mabey and Mill 1978). . The log P (octano1/water partition coeffi-
cient) value of -0.52 for trimethy1 phosphate suggests that the chemical
will not bioaccumulate significantly (Radding et al. 1977).
l-Butano1. !-methv1-. nhosnhate (!:1)(9CI) (919-62-0)

Synonyms: Phosphoric acid. triisopenty1 ester (8CI); called triisopentyl
phosphate for this report.
A review of the production range (includes importation volumes)
statistics for triisopenty1 phosphate (CAS No. 919-62-0) which are
listed in the initial TSCA Inventory (USEPA 1983). has shown that no
1977 production/importation' was reported or that all of the production.
~ange data reported were claimed as confidential by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA.
.
U.S.C. 2613(a».
. One U.S. company was listed as a producer of triisopenty1 phosphate
in the public. non-confidential 1977 TSCA Inventory (USEPA 1983). .
Monitoring data documenting worker, consumer and environmental
exposure to triisopenty1 phosphate were not. found. Manufacturing
processes for phosphate esters appear to be contained in closed system~
(Fernanda et al. 1972. as reported in Chem Abstr 79:91582m; Arct 1975.
as reported in Chem Abstr 83:163757e; USEPA 1985). indicating minimal
worker exposure during production. However. as with other phosphate
esters (USEPA 1985). worker exposure to triisopenty1 phosphate could
occur during the transfer and packaging or drumming of the compound.
Searches of the literature and patents revealed no significa~t uses
for triisopenty1 phosphate. but some information was found regarding
minor or potential uses. One patent described a procedure in which the
compound was used in the preparation of gelatin-free dispersions of a
photographic additive (Seifert et a1. 1983. as reported in Chem Abstr
1983). The compound may also be used in the extraction of vanadium(V).
iron. thallium, and titanium from aqueous hydrochloric acid solution'.
(Singh et al. 1983. as reported in Chem Abstr 99:77711j; Pandey and
Rupaiuwar 1979. as reported in Chem Abstr 92:113089h; Xakkar and
. Rupaiuwar 1977, as reported in Chem Abstr 89:118539y; Singh and
Rupaiuwar 1982. as reported in Chem Abstr 97:79831f); in the extraction
of thorium and uranium from aqueous solutions (Iaiawa1 and Rupaiuwar
1983. as reported in Chem Abstr 101:178551%); and as an extractant for
reprocessing of spent fuel from nuclear reactors (Rozen et al. 1984. as
reported in Chem Abstr 101:45138w).
. The data submitted for the TSCA Inventory. including production range
information. are subject to the limitations contained in the Inventory
Reporting Regulations (40 CFR 710).

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116
. Information on the degradation of other phosphate esters suggests
that, if released to the environment during its production or use, tri-
isopentyl phosphate would be likely to undergo biodegradation, but would
probably be stable to direct photolysis and chemical oxidation (Saeger
et al. 1979; Radding et al. 1977).
Phosonhoric acid, tri-!-nronenvl ester (1623-19-4)
Synonym:
Triallyl phosphate
Triallyl phosphate has been commercially available for several
years and although it is a known reactive monomer, it has not yet become
commercially significant (Beacham 1978).
A review of. the production range (includes importation volumes)
statistics for triallyl phosphate (CAS No. 1623-19-4) which are lis~ed
in the initial TSCA Inventory (USEPA 1983), has shown that no 1977
production/importation was reported or that all of the production range
data reported"were claimed as confidential by the'mailufacturer(s) or
importer(s) and cannot be disclosed (Section 14(a) of the TSCA, U.S.C.
2613(a». (See footnote on page 115".)
One of the two domestic producers listed in the public, non-
confidential file of the 1977 TSCA Inventory, the Sartomer Company (a
subsidiary of Atlantic Richfield Co.), is also listed as a producer in
Chem Sources U.S.A. (1982); however, the chemical was not listed in the
Directory of Chemical Producers (SRI 1984), suggesting that current
annual production, if any, is less than 5,000 pounds or '5,000 in value.
Monitoring data documenting worker, consumer and environmental
exposure to triallyl phosphate were not found. Manufacturing processes
for phosphate esters appear to be contained in closed systems (Fernanda
et al. 1972, as reported in Chem Abstr 79:91582m; Arct 1975, as reported
in Chem Abstr 83:163757e; USEPA 1985), indicating minimal worker expo-
sure to triallyl phosphate during production. However, as with other
phosphate esters (USEPA 1985), worker exposur~ could occur during the
transfer and pa~kaginl or drumming of the compound.
The major uses of triallyl phosphate indicated by patents (USEPA
1985) include catalyst for several reactions (USEPA 1985); adhesion pro-
moter (Mowdood and Maxey 1982, as reported in Chem Abstr 98:73682g);
lubricating oil additive (Ashkinazi et &1. 1983, as reported in Chem
Abstr 99:215514a); and filler for artificial bones and teeth (Tsunekawa
et al. 1982, as reported in Chem Abstr 98: 54654h). The compound may'
also have minor or potential uses as an intermediate (Hawley 1981); as a
flame retardant for textiles (Drake et al. 1980); as a textile modifier
(Heger et al. 1981, as reported in Chem Abstr 96:164097v); and as an
additive to enhance the insecticidal activity of pyridaphenthion (Mitsui
Chemicals, Inc. 1982, as reported in Chem Abstr 96:176167f).
The various industrial applications of triallyl phosphate are
potential sources of worker exposure; its use in ar~ificial bones and
teeth could result in consumer exposure.

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117
Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use. tri-
allyl phosphate would be likely to undergo biodegradation. but would
probably be stable to direct photolysis and chemical oxidation (Saeger
et ale 1979; Radding et al. 1977). .
Tridecanol. uhosuhate (!:!)(8CI) (3033-37-2)
Synonym:
None.
A review of the production range (includes importation volumes)
statistics for tridecanol phosphate (3:1) (CAS No. 3033-37-2) which is
listed in the initial4Public ~non~CDI) TSCA Inventory (USEPA 1983). has
shown that between 10 and 10 pounds of this chemical were reported as
produced/imported in 1977. (See footnote. page 113.) .
According to the public. non-confidential file of the TSCA Inven-
tory (USEPA 1983). one U.S. company produced tridecanol phosphate (3:1)
in 1977. No data were found regarding current production. The chemical
was not listed in Chem Sources U.S.A. (1982). in the Directory of Chemi-
cal Producers. or in the Chemical Economics Handbook (SRI 1981-1982).
indicating that current domestic production. if any. is probably not
significant.
Monitoring data documenting worker. consumer and environmental
exposure to the compound were not found. No information was found
regarding production methods for or uses ,of the compound.
Information on the degradation of other phosphate esters and
alcohols suggests that. if released to the environment during its pro-
duction or use. tridecanol phosphate (3:1) would be likely to undergo
biodegradation. but would probably be stable to direct photolysis and
chemical oxidation (Saeger et al. 1979; Radding et al. 1977).
Phosuhoric acid. tris(decvl) ester (9CI) (4200-55-9)
Synonyms: Phosphoric acid. tridecyl ester (8CI); called tridecyl phosphate
for this report.
A review of the production range (includes importation volumes)
statistics for tridecyl phosphate (CAS No. 4200-55-9) which is listed in
the initial publjc (non-CDI) ~CA Inventory (USEPA 1983). has shown that
between 1.1 x 10 and 1.1 x 10 pounds of this chemical were reported as
produced/imported in 1977. (See footnote. page 113).
According to the public. non-confidential file of the TSCA Inven-
tory (USEPA 1983). three companies proguced/imported the chemical in
1977. The maJ.ority of this (1-10 x 10 pounds) was imported. One com-
pany was listed as a supplier of the compound in Chem Sources U.S.A.
(1982). but producers were not listed in either Chem Sources or the
Directory of Chemical Producers (SRI ~984). indicating that current
domestic production of tridecyl phosphate is probably not in

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118
commercially significant quantities.
the compound were not found.
Current importation figures for
Monitoring data .documenting worker. consumer and environmental
exposure to tridecyl phosphate were not found. Manufacturing processes
for phosphate esters appear to be contained in closed systems (Fernanda.
et.al. 1972. as reported in Chem Abstr 79:91582m; Arct 1975. as reported
in Chem Abstr 83:163757e; USEPA 1985). indicating minimal worker expo-
sure during production. However. as with other phosphate esters (USEPA
1985). worker exposure to tridecyl phosphate could occur during the
transfer and packaging or drumming of the compound.
Major uses of tridecyl phosphate indicated by patents include
extraction solvent. stabilizer for pigments. and penetrant for wood-
plant herbicide (USEPA 1985). Other patents have been issued for its
use as part of a polymer in film resistors (Larry 1978. a~ reported in
CAS Online CAB9:207993j); in preparing coatings on fingerprint paper
(Buerkley et al. 1980. as reported in CAS Online CA94:55970n); to reduce
fouling of metal in contact with petroleum ether (Dvoracek 1984. as
reported in CAS Online CAlOl:9883b); as a flame retardant in cellulose
acetate (Wood and Gibson 1970. as reported in Chem Abstr 73:36775c); as
a stabilizer for polyester (Kyo et al.. 1978. as reported in Chem Abstr
.90:72894a); as a binder in particle board (McLaughlin et al. 1981. as
reported in Chem Abstr 94:210595q); and in preparini influenza and
rabies virus vaccines (Alexander 1969. as reported in Chem Abstr
76:117500y). The use of tridecyl phosphate as an antistatic agent has
been studied (Vasilenok et al. 1976. as reported in CAS Online
CAB 5 :47472a).
Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use. tri-
decyl phosphate would be likely to undergo biodegradation. but would
probably be .stable to direct photolysis. hydrolysis and chemical oxida-
tion (Saeger et al. 1979; Radding et al. 1977).
Phosnhoric acid. trioctadecvl ester (8CI) (9CI) (4889-45-6)
Synonym: None. Called trioctadecyl phosphate for this report.
A review of the production range (includes importation volumes)
statistics for trioctadecyl phosphate (CAS No. 4889-45-6) which are
listed in the initial TSCA Inventory (USEPA 1983). has shown that no
1977 production/importation was reported or that all of the production
range data reported were claimed as confidentiai by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA.
U.S.C. 2613(a». (See footnote. page 115.)
One U.S. company was listed
public. non-confidential file of
There was no evidence of current
Sources 1982. SRI 1984).
as a producer of the chemic_l in the
the 1977 TSCA Inventory (USEPA 1983).
production of the compound (Chem

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119
Monitoring data documenting worker. consumer and environmental
exposure t~ trioctadecyl phosphate were not found.
Significant uses of the compound.were not found. Minor or poten-
tial uses of compound indicated by patents included in a binder for use
in aluminum casting (Hitachi Chemical Co.. Ltd. 1984. as reported in
Chem Abstr 101: 112S4r); as a heat stabilizer in thermoplastic resins and
polypropylene fibers (Denki Kagaku Kogyo K.K. 1983. as reported in Chem
Abstr 101:8190m; Yasumura et ale 1971. as reported in Chem Abstr
76:114668y); as a stabilizer for polyester (Kyo et a1... 1978. as
reported in Chem Abstr 90:72894a); as a lubricant for aromatic polyamide
fibers (Nagasawa et ale 1974. as reported in Chem Abstr 82:44935f); in
an antistatic coating for photographic films (Mayama' et al. 1972. as
reported in Chem Abstr 78:10155d); in preparation of greases (Saraceno
1967. as reported in Chem Abstr 67:83690g); and to improve resistance to
blocking. staining and weathering in polyvinylchloride films (Achilles
Foam Board Co.. Ltd.. as reported in Chem Abstr 99:141040u).

Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use.
trioctadecyl phosphate would be likely to undergo biodegradation. but
would probably be stable to direct photolysis and chemical. oxidation
(Saeger et al. 1979; Redding et ale 1977).
Ethanol. !-methoxv-. DhosDhate (i:!)(9CI) (6163-73-1)
Synonym: None. Called 2-methoxyethanol phosphate (3: 1) for this report.
A review of the production range (includes importation volumes)
statistics for 2-methoxyethanol phosphate (3:1) (CAS No. 6163-73-1)
which are listed in the initial TSCA Inventory (USEPA 1983). has shown
that no 1977 production/importation was reported or that all of the pro-
duction range data reported were claimed as confidential by the
manufacturer(s) or importer(s) and cannot be disclosed (Section 14(a) of
the TSCA. U.S.C. 2613(a». (See footnote. page 115.)
One U.S. company was listed as a producer of the chemical in the
,public. non-confidential file of' the 1977 TSCA IJiventory (USEPA 1983).
'Monitoring data documenting worker. consumer and environmental
exposure to 2-methoxyethanol phosphate (3:1) were not found. Manufac-
turing processes for phosphate esters appear to be contained in closed
systems (Fernanda et al. 1972. as reported in Chem Abstr 79:91582m; Arct
1975. as reported in Chem Abstr 83:163757e; USEPA 1985). indicating
minimal worker exposure during production of the chemical. However, as
with other phosphate esters (USEPA 1985). worker exposure could occur
during the transfer and packaging or drumming of the compound.
Information regarding major uses of the compound were not 'found.
Patents have been issued th~t suggest minor or potential uses of the
compound as a solvent in the preparation of riboflavin 5'-phosphate, .
(Yamauchi et ale 1979. as reported in Chem Abstr 92:42338w). and as a

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120
catalyst in preparation of nucleotides (Yamauchi et al. 1976. as.
reported in Chem Abstr 86:190415k).
Information ~n the degradation of other phosphate esters suggests
that. if released to the environment during its production or use. 2-
methoxyethanol phosphate (3:1) would be likely to undergo biodegrada-
tion. but would probably be stable to direct photolysis and chemical
oxidation (Saeger et a1. 1979; RIdding et al. 1977).
Ethanol. !-(!-butoxvethoxv)-. uhosuhate (!:!)(9CI) (7332-46-9)

Synonym: None. Tri[(2-butoxyethoxy)ethanol] phosphate (3:1)
report.
for this
A review of the production range (includes importation volumes)
statistics for tri[(2-butoXyethoxy)ethanol] phosphate (3:1) (CAS No.
7332-46-9) which are listed in the initial TSCA Inventory (USEPA 1983).
has shown that no 1977 production/importation was reported or that all
of the production range data reported were claimed as confidential by
the manufacturer(s) or importer(s) and cannot be disclosed (Section
14(a) of the TSCA. U.S.C. 2613(a». (See footnote. page 115.)
One U.S. compaBY was listed as a producer of the chemical in the
public. non-confidential file of the 1977 TSCA Inventory (USEPA 1983).
Significant uses of the compound were not found. Tri[(2-butoxyethoxy)-
ethanol] phosphate (3:1) may have minor or potential uses in polymeric
resins for selective removal of trace metal impurities (Warshawsky et
al. 1979. as reported in Chem Abstr 91: 58266m; Warshawsky and Patchornik
1978. as reported in Chem Abstr 91:74510.); in cleaning compositions for
household floors (Mizutani et al. 1977. as reported in Chem Abstr
88:63522j); as a leveling agent in floor polishing materials (Lima and
Hopper 1969. as reported in Chem Abstr 71:720825); and as an ant~foaming
agent in aluminum manufacture (A1ufab 1973. as reported in ahem Abstr
80:72535c). .
Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use.
tri[(2-butoxyethoxy)ethanol] phosphate (3:1) would be likely to undergo
biodegradation. but would probably be stable to direct photolysis and
chemical oxidation (Saeger et al. 1979; Radding et al. 1977).

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121
!-Furanmethanol. tetrahvdro-. nhosnhate (3:.1) (9CI) (10427-00-6)

Synonym: Furfuryl alcohol. tetrahydro-. phosphate (3:1)(8CI);
tetrahydr.ofurfuranmethanol phosphate (3: 1) for thi 5 report.
A review of the production range (includes importation volumes)
statistics for tetrahydrofurfuranmethanol phosphate (3:1) (CAS No.
10427-00-6) which is listed in the initial PJblic (nin-CDI) TSCA Inven-
tory (USEPA 1983). has shown that between 10 and 10 pounds of this
chemical were reported as produced/imported in 1977. (See footnote.
page 113.)
According to the public. non-confidential file of the TSCA Inven-
tory (USEPA 1983). one U.S. company produced the chemical in 1977.
Monitoring ~ata documenting worker. consumer and environmental
exposure to tetrahydrofuranmethanol phosphate (3:1) were not found. .
No information was found regarding the production methods used for
this cheaical~ Manufacturing processes for phosphate esters appear to
be contained in closed systems (Fernanda et al. 1972. as reported in
Chem Abstr 79 :91582m; Arct 1975. as .reported in Chem Abstr 83: 163757e;
USEPA 1985). indicating minimal worker exposure during production. How-
ever. as with other phosphate esters (USEPA 1985). worker exposure could
occur during the transfer and packaging or drumming of the compound.
Significant uses of the compound were not found. Patents have been
issued that incorporate the use of the compound in erasible ink formula-
tion (Seregely and Kidda 1976. as reported in Chem Abstr 85:22914h;
Seregely and Kidda 1974. as reported in Chem Abstr 83:62095g); in the
hardening of photographic emulsions (Stauner et al. 1974. as reported in
Chem Abstr 82:78768u); and in phosphate gel coating for air filters
(Hamilton 1968. as reported in Chem Abstr 69:45854x). .
Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use.
tetrahydrofuranmethanol phosphate (3:1) would be likely io undergo
biodegradation. but would probably be stable to direct photolysis and
chemical oxidation (Saeger et al. 1979; Radding et al. 1977).
1-Hexadecanol. nh~snhate (1:1) (9CI) (56827-95-3)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for hexadecanol phosphate (3:1) (CAS No. 56827-95-3) which
are listed in the initial TSCA Inventory (USEPA 1983). has shown that no
1977 production/importation was reported or that all of the production
range data reported were claimed as confidential by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA.
U.S.C. 2613(a». (See footnote. page 115.)

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122
According to the public, non-confidential file of the TSCA Inven-
tory (USEPA 1983), the one U.S. manufacturer of the chemical listed on
the Inventory did not produce it in 1977. No information was found
regarding .current production of the .chemical.
Monitoring data to document worker, consumer, and environmental
. exposure to hendecanol phosphate (3: 1) were not found.
The compound has been produced by esterification of phosphoric acid
with alkylhalides (Gomez and Sutaria 1974, as reported in Chem Abstr
85:108252c). Manufacturing processes for phosphate esters appear to be
contained in closed systems (Fernanda et ale 1972, as reported in Chem
Abstr 79:91582m; Arct 1975, as reported in Chem,Abstr 83:163757e; USEPA
1985), indicating minimal worker exposure during production. However,
as.with other phosphate esters (USEPA 1985), worker exposure to hexade-
canol phosphate (3:1) could occur during the transfer and packaging or
drumming of the compound.
Major uses of hexadecanol phosphate (3:1) were not found. Minor or
potential uses may include as an antistatic agent for thermoplastics
(Vasilenok et ale 1976, as reported in CAS Online CA85:47472a); in
liquid crystal display cells for controlling orientation (Canon 1982, as
reported in Chem Abstr 99:222497a); and to improve resistance to block-
ing, staining and weathering in polyvinylchloride films (Achilles Foam
Board Co., Ltd., as reported in Chem Abstr 99:141040u).
Information on the degradation of other phosphate esters suggests
that, if released to the environment during its production or use, hexa-
decanol phosphate (3:1) would be likely to undergo biodegradation, but
would probably be stable to direct photolysis and chemical oxidation
(Saeger et ale 1979; Radding et ale 1977).
1-Hexacosanol, DhosDhate (1:1) (9CI) (64131-07-3)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for hexacosanol phosphate (3:1) (64131-07-3) which are listed.
in the initial TSCA Inventory (USEPA 1983), has shown that no 1977
production/importation was reported or that all of the production range
data reported were claimed as confidential by the manufacturer(s) or
importer(s) and cannot be disclosed (Section 14(a) of the TSCA, U.S.C.
2613(a». (See footnote, page 115.) .
According to the public, non-confidential file of the TSCA Inven-
tory (USEPA 1983), the one U.S. manufacturer of the chemical listed on
the Inventory did not produce it in 1977. No information was found
regarding current production of the chemical.
. .
Monitoring data to document worker, consumer, and environmental
exposure to hexacosanol phosphate (3:1) and information regarding pro-
duction methods were not found. As w~th other phosphate esters (USEPA
1985), worker exposure to hexacosanol phosphate (3:1) c'ould occur during

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123
the transfer and packaging or drumming of the compound at the production
site.
No data were found regarding major. minor or potential uses of the
chemical.
Information on the degradation of other phosphate esters suggests
tha t. if rei eased to the enviromaent during its production or use. hex-
acosanol phosphate (3:1) would be likely to undergo biodegradation. but
would probably be stable to direct photolysis and chemical oxidation
(Saeger et ale 1979; Radding et ale 1977).
1-Tetracosanol. uhosuhate (1:1) (64131-08-4)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for tetracosanol phosphate (3:1) (CAS No. 64131-08-4) which
are Ii sted in the ini tial '!'SCA Inventory (USEPA 1983). has shown that no
1977 production/importation was reported or that all of the production
range data reported were claimed as confidential by the manufacturer(s)
or importeds) and cannot be disclosed (Section 14(a) of' the '!'SCA.
U.S.C. 2613(a». (See footnote. page 115.) . .
The publ ic. non-confidential file of the '!'SCA Inventory (USEPA
1983) indicates that the compound was not manufactured in 1977 by the
one U.S. producer listed on the Inventory. Current production informa-
tion was not found.
Monitoring data to document worker. consumer. and enviromaental
exposure to tetracosanol phosphate (3:1) and information regarding pro-
duction methods were not found. As with other phosphate esters (USEPA
1985). worker exposure to this compound could occur during the transfer
and packaging or drumming of the compound at the production site.
No data were found regarding major. minor"or potential uses of the
chemi cal.
Information on the degradation of other phosphate esters suggests
that. if released to the enviromaent during its production. or use.
tetracosanol phosphate (3:1) would be likely to undergo biodegradation,
but would probably be stable to direct photolysis and chemical oxidation
(Saeger et ale 1979; Radding et ale 1977).
1-Docosanol. uhosuhate (1:1) (9CI) (641~1-09-5)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for docosanol phosphate (3:1) (CAS No. 64131-09-5) which are
listed in the .initial '!'SCA Inventory (USEPA 1983). has shown that no
1977 production/importation was reported or that all of the production

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124
range data reported were claimed as confidential by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA.
U.S.C. 2613(a». (See footnote.. page 115.)

. The public. non-confidential file of the TSCA Inventory (USEPA
1983) indicates that the compound was not manufactured in 1977 by the
one U.S. producer listed in the Inventory. Current production informa-
tion was not found.
Monitoring data to document worker. consumer. and. environmental
exposure to docosanol phosphate (3:1) and information regarding produc-
tion methods were not found. As with other phosphate esters (USEPA
1985). worker exposure to this compound could occur during its transfer
and packaging or drumming at the production site.
No data were found regarding major. minor or potential uses of the
chemical.
Information on ~he degradation of other phosphate esters suggests
that. if released to the environment during its production or use.
docosanol phosphate (3:1) would be likely to under&o biodegradation. but'
would probably be stable to direct photolysis and chemical oxidation'
(Saeger et al. 1979; Radding et al. 1977).
!-Eicosanol. uhosuhate (!:!) (9CI) (64131-10-8)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for olcosanol phosphate (3:1) (CAS No. 64131-10-8) which are
listed in the initial TSCA Inventory (USEPA 1983). has shown that no
1977 production/importation was reported or that all of the production
range data reported were claimed as confidential by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA.
U.S.C. 2613(a». (See footnote~ page 115.) .
The public. non-confidential file of the TSCA Inventory (USEPA
1983) indicates that the compound was not ,manufactured in 1977 by the
one U.S. producer listed on the.Inventory. Current production informa-
tion was not found.
Monitoring data documenting worker. consumer. and environmental
exposure to eicosanol phosphate (3:1) and information regarding produc-
tion methods were not found. As with other phosphate esters (USEPA
1985). worker exposure to this compound could occur during transfer and
packaging or dr~ing.
No data were found regarding major. minor or potential uses of the
chemical.
Information on the degradation of other phosphate esters suggests
that. if released to the environment during its production or use.
eicosanol phosphate (3:1) would be likely to undergo biodegradation. but

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125
would probably be stable to direct photolysis and chemical oxidation
(Saeger et al. 1979; Radding et al. 1977).
1-0ctacosanol, DhosDhate (3:1) (9CI) (64131-18-6)
Synonym: None.
A review of the production range (includes importation volumes)
statistics for octacosanol phosphate (3:1) (CAS No. 64131-18-6) which
are listed in the initial TSCA Inventory (USEPA 1983), has shown that no
1977 production/importation was reported or that all of the production
range data reported were claimed as confidential by the manufacturer(s)
or importer(s) and cannot be disclosed (Section 14(a) of the TSCA,
U.S.C. 2613(a». (See footnote, page 115.)
The public, non-confidential file of the TSCA Inv.entory (USEPA
1983) indicates that the compound was not manufactured in 1977 by the
one U.S. producer listed on the Inventory. Current production informa-
tion was not found.
. Monitoring data to document worker, consumer, and environmental
exposure to octacosanol phosphate (3:1) and information regarding pro-
duction methods were not found. As with other phosphate esters (USEPA
1985), worker exposure to this compound could occur during transfer and
packaging or drumming.
No data were found regarding major, minor or potential uses of the
chemical.
Information on the degradation of other phosphate esters suggests
that, if released to the environment during its production or use,
octacosanol phosphate (3:1) would be likely to undergo biodegradation,
but would probably be stable to direct photolysis and chemical o~idation
.(Saeger et a!. 1979; Radding et al. 1977>. .
Polv(~l,!-ethanedivl), .alDha.,.alDha.',.alDha."-
DhosDhinvlidvnetris(.omeaa.-hvdroxv- (64502-13-2)

Synonym: None. Called Poly-3 for this report.
Production data were. not found for Poly-3. No information was
found to indicate major uses of the compound. One patent was found for
the use of Poly-3 to protect steel wool against dissolution during the
recovery of silver from used photographic solutions (Fisch 1977, as
reported in Chem Abstr 87:170983m). No other information was found for
this chemical.

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126
Polv(~!,!-ethanedivl), .aluha.,.aluha.',.aluha."-
uhosuhinvlidvnetris(.omeaa.-(tridecvlo%v)- (73070-47-0)

Synonyms: None. 'Called Poly-4 for this report.
A review of the production range (includes importation volumes)
statistics for Poly-4 (CAS No. 73070-47-0) which is listed in the ini-
tial public (non-CBlj TSCA Inventory (USEPA 1983), has shown that
between 0 and 1 % 10 pounds of this chemical were reported as .
produced/imported in 1977. (See footnote, page 113.)
According to the public, non-confidential file of the TSCA Inven-
tory (USEPA 1983), one U.S. company produced the chemical in 1977. No
information was found regarding production methods, current production
or uses of the compound.
Polv(~!,!-ethanedivl), .aluha.,.aluha.'-(metho%v-
phosphinylidene )bis( .omega.-hydroxy- (74049-24-4)
. .
Synonyms: None. Called Poly-S for this report.
A review of the production range (includes importation volumes)
statistics for Poly-S (CAS No. 74049-24-4) which are listed in the ini-
tial TSCA Inventory (U~EPA 1983), has shown that no 1977 production/-
importation was reported or that all of the production range data
reported were claimed as confidential by the manufacturer(s) or
importer(s) and cannot be disclosed (Section 14(a) of the TSCA, U.S.C.
2613(a». (See footnote, page lIS.)
One importer of this chemical is listed in the public, non-
confidential file of the 1977 TSCA Inventory (USEPA 1983). Data regard-
ing current production of the compound were not found.
Information was not found to indicate major uses of the compound.
Patents were found for minor or potential uses as light stabilizers in
poly(butylene terephthalate) fibers delustered with titanium dioxide
(Bloecker et ale 1980, as reported in Chem Abstr 94:17046h), and as a
binder in aluminum oxide storable refractories (Suganama et ale 1980, as
reported in Chem Abstr 93:30788a). .

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127
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128
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132
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