CHEMICAL HAZARD INFORMATION PROFILE*
DRAFT REPORT
. Noaylphenol
25154-52-3
September 17. 1945
DISCLAIMER
This document is a preliminary draft and has not beeu formally peer and admin-
istratively reviewed within the Office of Toxic Substances. Office of Pesti-
cides and Toxic Substances, U.S. Environmental Protection Agency (USEPA).
This draft report has been prepared under contract to USEPA 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.
ifcration of trade names or commercial -products does mot constitute Agency endor-
sement 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 ia
the 1977 TS£A Chemical Substance Inventory, and enables OTS to decide on a
disposition for the subject -chemical regarding level of concern and the aeed
lor further asaessment. The Of IP contains a summary of readily available
health, environmental effects, and exposure data. In general, little or ao ia
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.
-------
DRAFT REPORT
CHEMICAL msAan INFORMATION PROFILE
Subject? Nonylpnenolj 4-Nonylpnenol; 2-Nonylphenol
Prepared by: Elizabeth L. Etnier
Chemical Effects Information Group
Information Be search and Analysis
Oak Jtidge National laboratory
Chemical Name: Nonylphennl (adzed isonexs)
(CAS No. 25154-52-3)
4-Nony 1 phenol
(CAS No. 104-40-5)
.2-Nonyl phenol
(CAS No. 136-83-4)
September 17. 1985
Rationale for Select ion: La* LCso values reported for aquatic
invertebrates and fish (Table 9); very
high concentrations of nonylphenol
found in sewage sludge (Giger et al. 1984);
high production Tolame.
.EXUUUT1VE SUMMARY
A. Exposure
Technical grade nonylphenol is a mixture of monoalkyl phenols, predom-
inantly para—substituted. The side chains are isomeric branched nonyl groups.
The i some*, or mixtures xited In the literature axe not always specified.
Recent production figures fox nonylphenol indicate Otat 140 million
pounds were produced in the United States in 1982, and consumption will
increase to 165 million pounds by 1987. Nonylphenol is currently produced by
10 companies, at 13 aites, with no importation occurring.
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Industrial manufacture of nonylphenol is by liquid-phase alkylation of
phenol with sized isomeric nonenes in the presence of an acid catalyst. Fol-
lowing production, nonylphenol is stored in dims for latex shipment in 55
gallon dnsis ox tank cars. Nonylphenol is rarely -used alone as an end pro-
duet. However, it is used extensively in the production of nonionic ethoxyla—
ted surfactants, and to * lesser extent in the mansfacture of phosphate
antioxidants, oil additives, synthetic lubricants, and corrosion inhibitors.
One of the 13 production sites reports no worker exposures to nonylphenol
during 10 years of production and use. No data are available regarding worker
exposure to nonylphenol ox its isomers at the other 12 prodnction sites,
although it is estimated that up to 4 workers/site are dentally exposed during
sampling and drumming. - Inhalation exposures are expected to be low.
Occupational -exposure to -nonylphenol during the prtd-actioir of nonylphenol
exhoxylates and phosphite antioxidants will be similar, although the latter
will be produced at only three sites. Potential exposure may occur while
undrnsuBing and charging the nonylphenol to a reactor, and during sampling
activities. It is estimated that up to 4 worker a/site would be exposed for
less than 1 hr/day during these activities, for about 330 days/year. Dermal
exposure to nonylphenol would remain low if protective gloves are worn.
Inhalation exposure -would again be negligible.
Here ia no information available on consumer exposure to nonylphenol.
Consumer exposure to products that may contain nonylphenol can occur during
the -use of cosmetics, detergents, pesticides, etc. One study detected low
levels of nonylphenol in two office buildings, but the source(s) of the nonyl-
phenol was not identified.
A few measurements of nonylphenol in wastewaters have been reported in
the literature,., and range from 0.002 to 4 :ng/L (4-nony 1 phenol). It ias been
estimated that only 30 kg/yr will be released during the manufacture of nonyl-
phenol. High levels of 4-nonylphenol were found in stabilized sewage sludge
containing surfactants, suggesting origination from anaerobic degradation of
alkylphenol ethoxylatea. Ximited studies indicate that nonylphenol itself Is
slowly biodegradable.
Although the log P (octanol—water) for nonylphenol is relatively high
(4.10), bioconcentration factors in the saltwater mussel, Mytilus edulis were
low, ranging from 1*4-13.. Studies .measuring downstream effluent wastes indi-
cate that nonylphenol is dispersed by the water body and-does not accumulate
in sediments.
B. Health Effects
A phsAaeokinetics study in rats following oral and istraperitoneal
administration of ^C-nonylpheuol showed the animals excreted the label in
urine (19%) and feces (701). but not as exhaled C02. Ion exchange ehromato-
graphy indicated that 22% of the urinary metabolites were neutrals, and that
: the.remainder were mainly glnonronie acid conjugates of nonylphenol.
The reported oral ID50 for rats ranges from 580 to 1537 mg/kg a-nd the
dermal IDfO-fox xabbits xanges f ron 2031 to <3160 .Kg/day. Mixed nonylphenol
ii
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caused moderate necrosis (graded 6 on a scale of 1-10) when applied at a
strength of 10 mg/24 hr to rabbit skin. It caused severe corneal damage (gra-
ded 10 oa a acale of 1-10) as a 1* solution applied to rabbit eyes.
No information was found on the testing of nonylphenol for oncogenicity,
genotoxicitjr, or teratofeaicity/reproductive -effects.
C. JEnvironsiental Effects
Nonylpheaol was found to be -very toxic to all aquatic organisms studied,
with EC-, and LC_0 values ranging from 0.13 to 5.0 mg/L. The two bivalves
studied, a nonmocile alga, and the freshwater ide appear to be the most resis-
tant to nonylphenol toxicity, with all other organisms tested exhibiting LQso
values below 1.0 mg/L. Adverse behavioral effects and swollen bodies with
hemorrhaged areas .have been observed in fish undergoing acute toxicity tes-
.ting.
The uptake and excretion of 4-nonylpnenol and nonylphenol were studied in
two saltwater species. Tae uptake of 4-nonylphenol in Salao salar increased
rapidly for the first two days of exposure (mean nonequilibrinm bioconcentra-
tion factor about 200), and then decreased by one order of magnitude after 4
days. Excretion was almost complete four days following exposure. „ In the
mussel, ifvtilus edulis. maximum concentrations were found to occur at 0.4
days, with an estimated half-time for clearance of 0.3 days. No .other data on
metabolism in aquatic organisms was fonnd.
Nonylphenol was found to depress the growth rate of cultures of Chlorella
ovrenoidosa at 0.025 Bg/mL, and to kill 100% of the cells at 25 ug/mL. In the
same study, nonylphenol was found to produce ultrastructural changes in the
cell walls, and distort the flagellae of Chlamvdomonas reinhardii.
iii
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TABLE OF CONTENTS
Chemical Hazard Information Profile
Nonylphenol
JE3EOJIIVE SUMMARY . i
3, SummaTy of Available Data ........................................... 1
A. Chemical Identity M..^. .........,._..« 1
B. Physics! and Chtaical Properties .................................... 1
C. Exposure 1
1. Worker Exposure 1
2. Consumer Exposure 10
3. Environmental Exposure 10
J>. Health Effects ... 18
1. Metsbolisa ..... ,..._ 18
2. Lethality 18
3. Oncogen!city 18
4. Genotoxicity . 18
5. Teratogenicity/Reproductive Effects ... 18
6. Other Effects 18
7. Case Reports and Epidemiologies! Studies 20
E. Environmental Effects 20
1. Metabolism ..- . 20
2. Lethality ... 20
3. Reproduction 22
4. Behavior and Growth 22
5. Population Effect* „.. 23
6. Other Effects 24
7. Abiotic Effects 24
P. Existing Standards. Regulations, and Recommendations .............. 24
II. Iteferenoes ~».. 23
A. Literature Cited 25
B. Supplemental Information .......................................... 32
C. Secondary Sources Searched ........................................ 34
1. Books ^ 34
2. Data Bases 39
3. Search Strategy 39
D, Chemical Specific Sources Searched ................................. 40
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I. Summary of Avail abl e D a ta
Technical -grade nonylphenol is a mixture of-monoalkyl phenol*, predom-
inantly para-substituted (Hawley 1981). He substitutions occur vita various
iaoaexic branched—chain nonyl groups (Seed 1978). Hie iaomer or mixture used
ia stsdie* reported in the literature is not always specified. In this
report, nonylphenol (sized isosers) and the unidentified isomers will be dis-
cussed as nonylphenol, and when identified as such in the literature, the par-
ticular isoner (4- or 2—nonylphenol) will be Indicated.
A. Chemical Identity
He chemical identities of nonyl phenol (-adzed isomers).,'4-nonylpheaal.
and 2-nonylphenol are listed in Table 1.
S. Physical sad Cheaiical Properties
Nonylphenol is a viscous liquid, pale yellow la color, with a slightly
phenolic odor (Hawley 1981). Dietz and Traad (1978) list an odor threshold of
1000 ug/L for p-nonylphenol. The physical and chemical properties of nonyl-
phenol (aiized isomers), 4-nonylphenol, and'2-nonylphenol are listed in
Table 1.
C. . Exposure
1. Worker Exposure
a. Production/Importation
Estimated production of nonylphenol for 1982 was 140 million pounds (SKI
1984, as reported ia USEPA 1985a). Consumption is expected to increase to 165
million pounds *y 1987 (Maansrille 1982, as reported in USEPA 1985a).
A review of the production range (includes importation volumes) statis-
tics for 4-aonylphenol (CAS No. 104-40-5) and nonylphenol, aiized isomers (CAS
No. 25154-52-3) which are listed in the initial TSCA Inventory (USEPA 1983),
has shown that between 3 and 30 million pounds of 4-nonylphenol and between 11
and 60 million pounds of agnylphenol (sized isomers) were reported as
prod need /imported in 1977. SCI (1985) reports that approximately 18 million
pounds of 4-nonylphenol were manufactured ia 1984 for sale aad internal use.
*
A review of the production range (includes importation-volumes) statis-
tics for 2-nonylphenol (CAS No. 136-83-4) which are listed ia the initial TSCA
Inventory (USEPA 1983). has shown that no 1977 production/importation was
reported or that all of tlie .production range data reported were claimed as
* This prod-notion range information de«s aot include any
l>rcdnction/importation data claimed aa confidential by the person(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 subject to the limitations contained in the Inventory .Reporting
Regulations (40 CFR 710).
-------
eaiMl Idtatlty
of
fefistc*
i.
i.
It
I.
4. IttMttrti
Moitctlar toravlti
i. MftJMl Bttt*:
I. MMtU| Poist (*C):
4. MoiIi«B Polit (*C):
jl. Mobilities in
(1) lit.*
(b)
I. DUIociitloB tok«ti»t:
). Pitiltioo CokffieUat (lo| P)
(Oct«iol/t«t»t):
I. teBiity (|/o«3):
i. Volttlllty:
JJ154-SJ-J
l. »o«yl- (IC1X9C1)
i•<)••*•)i NoByl-
Pr*rostl*l VoB-100|
ipt?lpk»Mi (e
No.
220.1
Civtn •t»**-eolor«d vitooc*
295-)20
101.1
ioluble»i
5 M/L it 20-2S*C';
8H|ktly solokle in
dilnt* tqoeottl N«0fle
Soluble !• btniene, «bl or luted »ol-
v«Bt». tall in*, tiepttne,
•Icokoll. etbylen*
Net FotMd
4.10'
0.949^
prexore -
104-4&-J
- (90)
C.H.,
220. S
tolnble U mot or
cold ••t«t «*d iqMOK* alkali
Not Fotmd
Ke.ol, o-.o^l- (ICJ)«
220. S
Not Pooad
23 M
-------
T«bl> 1. (Contlntud) Miyaical j Chemical Proper11e» .of Nonylphtnol
10. Otner
•
0
d
a
t
1
h
•efraetive indat (oJfi)t
Vapor dantity: a* reported in ttann and Jenton 1974
WlBdholt at al. 1983
ifeitt 1980
Jttitco 19851
-------
confidential by ^h* manufactured s) and/or importers and cannot be disclosed
(Section 14U) of the ISCA. TJ.S.C 2fii3(a)).
h. Prod ueexa/ Importers
Domestic producers of 4—nonylphenol and nonylphenol < mixed isaners) fox
1977, their addresses, end the reported "production, as liated in the public,
non-confidential poxtion of the TSCA Inventory, axe given in Table 2 and 3,
respectively. One unidentified manufacturer fox 2-nonylphenol is listed in
USEPA (1983), with the plant site not on file, and production -volume not
reported fox 1977.
Nonylphenol ia cvxxently masnfactnxed by 10 .companies at 13 sites In the
United States, with limited ox no importation of nonylphenol occurring. Leas
•than 101 of -the cnxrent market is exported (SRI 1984, as xeported in USEPA
1985a), Table 4 liats the location and production capacity of each of the
plants. Listed capacity ia principally that of nonylphenol and dodecylphenol,
although other alkylphenols axe generally produced with the same equipment
(TJSEPA 1985a). SCI (1985) xepoxta that they manufactured approximately 18
million pounds of nonylphenol in 1984 fox sale and internal use.
e. .Pxodnction Methods
Industrial manufacture of nonylphenol is by liquid-phase alkylation of
phenol with nixed isoaeric nonenes (propylene trimez) in the presence of an
acid catalyst. This catalyst may be snlfnxio acid, aluminum trichloride, or
boron triflnoride. Material requirements for a yield of one metric ton of 4-
nonylphenol are 620 kg phenol* 450 kg nonene, and a small amount of catalyst.
Premised phenol and nonene are fed to an agitated, jacketed tank reactor where
they xeact at 50 to 100° C fox 30 to 120 min, and yield a mixture of isomers,
mostly para—, with some ortho- and 2,4-dinonyl substitution (Lowenheim and
Koran 1975). The crude prod-net is washed several times and heated under
vacuum to remove traces of reactants and water. In the final step, nonyl-
phenol is sepaxated by vacuum distillation at 10 to 20 mm fig. Nonylphenol is
recovered at the top of the distillation column, stored, ox shipped in 55 gal-
lon drums ox tank caxa. Oinonylphenols are recovered as bottoms (USEPA
19B5a). The yield of nonylphenol is about 75-80%, and the yield of dinonyl-
phenol ia about 10-20% (Lowenheim and Jfoxan 1975).
d. Industrial/Occupational Uses
The pxineiple -use of -nonylphenol ia as an intermediate in the production
of nonionic ethoxylated surfactants. About 70% of the nonylphenol produced is
used in this fashion (Lowenheim and Jfoxan 1975), and nonylphenol ethoxylate is
the dominant alkylphenol ethoxylate surfactant (USEPA 1985a). However, this
use is not expected to expand im the United States aa nonylphenol-derived
detergents have poor biodegradability, and axe not used in household clean-
sers. In Europe they -axe still used im cleansers (Lowenheim and Koran 1975).
.* The data submitted for "the ISCA Inventory including production-range
information, are subject to the limitations contained in the Inventory
fiepoxting ftegnlatioms (40 CFB 710).
-------
Table 2. 1977 Product ion of 4-Noorylphenol
Company Production*
Perro Corp. KEb
Pzodsctol Chem. JHv,
10051 fioaandel Ave.
Scuta Pe Springs, CA
TJni royal. Inc. 1-10
Bni royal Chem. Div.
Elm Street
Nangatnck* CT
£ch«nectadjr Cham,. lac. 1-10
Honte 5S
fiotterda Jet, TO
Sohmectady Chea., Inc.
P.O. Box 2830
Treeport, TZ
GAP Corporation ~* NR
P.O. Box 12
Linden, NT
GAP Corporation NS
P.O. Box 37
Cmlvert City, XY
•Million* of -pounds.
**Not reported.
Source: USEPA 1983 a.
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T«ble3. 1977 Production of Nonylphenol (JLLzed Isoaers)
CoBpany
Production11
Union Carbide Corp.
iiver Road
"Boand Brook, NT
Borg-Wmrner Chen.
P.O. Box 816
Morgantovn, W
Montedison USA*
1114 Are. of tie A« ericas
Nev Ibrk, NT
-RoJun ? Haas
5000 Eiehaond St.
Philadelphia,. PA
Robm f Haa«
P.O. Box 672
Deer Paxk, TX
Continental Oil Co.
191 Dorenns Ave.
Newark, NT
Benlry ^ Co., Inc.c
750 third Ave.
Nev Xork. NT
Filo Chem. Corp.c
347 Madison Ave.
New Tork, NY
Monsanto Company
Pennsylvania Are.
Eearny, NT
Kalaaa Chen., Inc.
1296 N.Y. 3rd St.
Ealaaa, WA
Jefferson Chen. Co.
P.O. Box 847
Port Necaes. IX
Ferro Corp.
Productol Che. Div.
10051 Ronandel Ave.
Santa Fe Springs, CA
None
NR
None
N£
None
19-50
1-10
NB
-AMjLllions of.'.ponnds.
*Not reported.
cl«porters.
Source: USEPA 1983 a.
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Table 4. Plant Capacity for U.S. Producers of Nonylphenola,b,c
Company
Standard Oil
of CA
ScJtenectady
Bori-farnex
lionsanto
Exxon
*ok» f Haa*
Rohm «• Haas
Texaco
SchenectAdy
GAP
Ealaaa
GAP
Uni royal
Location
-Belle Chaste, LA
Oystex Creek. 13
Koxgantown, W
Eeamy. NT
Sayvay. NT
Deer Park, IX
Philadelphia. PA
Port Neches.TX
lotterdaa Jet. NI
Linden. NT
Kalana, WA
Calvext City. KT
Navgatucl. CT
Capacity
Onillion Ib)
86
75
€0
45
40d
40
40
35
25
20
20
15
10d
«HSEPA 1P85.
bA§ of January 1983.
cIncludes production of dodecylphenol and other alkylphenols.
^Captive use.
-------
In producing these surfactants; nonylphenol is reacted, generally in a
batch process, with ethylene oxide in the presence of a basic catalyst, to
yield ethoxylates of various polyethylene oxide chain lengths (USEPA 1985a).
By changing the Jttles of ethylene oxide, the ase and solubility of the surfac-
tant changes (the water solubility increases as chain.length increases).
Earalsifiers for grease and oil axe produced with 4 to € sales of ethylene
oxide per molecule of nonylphenol, laundry detergents with 7 to 11 soles.
emnlsifiers for solvents and pesticides with 13 to 15 moles, and emulsion
polymerization of latex is achieved with 30 to 40 moles of ethylene oxide
(USEPA 1985a). He 8 and 9 mole ethoxylates fora the basis of high perfor-
mance detergents, particularly for textile scouring, but they have been repla-
ced by straight chain C.--C,. alcohol ethoxylates in household detergents
(feed 1978). " **
-. Pif teem vompaniee produce -these alky lphenol-«xhoxy late surfaetaats, -using
about 97.5 to 112.5 million pounds of nonylphenol. for use priaarily as indus-
trial or agricultural cleansers (USEPA 198Sa). One to their lack of sudsing
ability, these surfactants are rarely used as laundry detergents or as con-
sumer products, however, an increase in its use has appeared in private label
asd generic household cleaning prod-nets (USEPA 1985a).
Alyklphenol exhoxylate .surfactants are produced by GAT. ttomsanto, Bohsi 1
Baas, Texaco. Union Carbide. BASF. Diamond Shamrock. ICI Americas. Mil liken,
Millmaster Onyx, Jf f T Chemicals, National Distillers, Stephan, Thomp.son-
Hayward. and Vitco (SRI 1983. as reported in USEPA 1985a).
Ihe second largest -use of nonylphenol is in the plastics and rubber
industry, where it is used as an intermediate in the manufacture of phosphite
antioxidant s. Approximately 15% of the nonylphenol produced was used for this
purpose in 1975 (Lowenheim and Noran 1975). The principle use of nonylphenol
as a phosphite antioxidant is in the form of tris-4-nonylphenol. phosphite
(TNPP), produced by Borg-ffagner. GAP, said 01 in Corporation (SRI 1983, as
reported in USEPA 1985m). The TNPP is produced through esterification of
nonylphenol in the presence of phosphoric acid, stored, then drummed in 55
gallon drums. Estimated production volume is 14 million pounds at the three
sites (USEPA 1985a). TNPP is used principally as a liquid stabilizer system
for polyvinyl chloride resins, and secondly as an antistaining antioxidant for
other plastics and elastomers. Phosphites have been approved for indirect
food use (SH 1983. as reported in USEPA 1985a).
About 10% of thejnonylphenol produced is reacted with formaldehyde to
form compound a -useful as oil additives and synthetic lubricants. The
remaining use of nonylphenol (5%) is as an intermediate in the manufacture of
polyvinyl chloride plasticizers. in Pharmaceuticals, and as corrosion inhibi-
tors (Lowenheim and Koran 1975).
Nonylphenol by itself does mot appear to nave any direct «nd -uses (Seed
1978; SCI 1985) although one significant application is in an admixture with
diisobutyl phthalate for marking fuel oil for taxation purposes (Reed 1978).
Nonylphenol is labelled as a major inert component (50.5%. acting as a surfac-
tant) of the pesticide, Matacil 1.8-fi, nsed in control 1 ing - spruce budworm in
eastern Canada (Snndaram et «1. 1980). Although not confirmed by other
reference sources, Weinberger, and -Re* (1982) state that nonylphenol is a
-------
widely used constituent of paints, inks, and shampoos, and fiantuccio et al.
(1984) note lhat nonylphenol la used in cosmetic*.
e. Detection Method*
Nonylphenols are Jiot detectable by tie -standard -methods n*ed fox the col-
lective determination of nonionic surfactant* (Giger et al. 1981). High reso-
lution gaj chromatography has been successfully used to separate technical
grade 4-nonylphenol into nine major peaks identified as para-substituted com-
pounds as well a* a minor amount of ortho-substituted compounds. Nonylphenols
can also be identified by their fragmentation patterns with mass spectreaietry.
Anstern et al. (1975) de-vised a method of detecting low levels of nonyl-
phenol in wastewater. This method includes extraction with freon, concentra-
tion of the extract ±m a EM eras-Danish apparatus, ami gas chromatography -with
.a hydrogen flame detector. Recovery from spiked raw and txeated wastewaters
•was 99.9 ± 3,5%. with the minimum detectable quantity being 2.2 ng.
. f. Woxker Exposure
No data are available regarding worker exposure to nonylphenol during its
sunuf acture. However, worker exposure scenarios have been developed, based on
models presented by USEPA (1984, as reported in TJSEPA 1985a), utilizing
parameters such as vapor pressure* form of the material, and concentration of
the material. Since the preparation of nonylphenol takes place in a closed
reactor system, there is not likely to be any occupational exposure during
this step in its manufacture. There is, however, a potential for exposure to
nonylphenol during the activities of sampling and loading the product (Mon-
santo 1985a). The USEPA (1985a) estimates that np to 4 workers/site could be
exposed in this fashion for np to 4 hr/day for 250 days/year. If the workers
wear gloves, dermal exposure would be low. Due to. the low vapor pressure of
nonylphenol, inhalation exposure*- are expected to be negligible (TJSEPA 1985a).
Occupational exposure during the production of nonylphenol ethoxylates
and phosphite antioxidant* will be similar, although the latter will be produ-
ced at only three sites. Potential exposure may occur while nndrnmming and
charging the nonylphenol to the reactor, and during sampling activities.
USEPA <1985a) estimate* that up to 4 workers/site would be exposed for less
than 1 hr/day during these activities, for about 330 days/year, dermal expo-
sure would remain low if protective gloves axe worn, but would be similar to
'that during manufacture if gloves are not worn. Inhalation exposure would
again be negligible (USEPA 1985m).
SCI (1985) state that in 10 years of making, handling, and -using nonyl-
phenol, no employee exposure problems attributable to nonylphenol have been
experienced.
Ikeda et al. (1970) suggest the possibility that a certain-portion of
•nonylphenol used to produce nonionic surfactant* used in detergents might
remain nnreacted, and appear as a contaminant in the final detergent product.
They also suggest the possibility that the polyoxyethylene alkylphenylethers
used in the detergents may decompose to yield free aUcylphenol.
-------
10
2. Consumex Exposure
Consumers might be exposed to nonylphenol daring the handling and use of
various products to which it is reportedly added. These include cosmetics
(Rantnccio et al. 1984, Weinbnrger and Rea 1982), the pesticide Matacil (Sna-
dazam et al. 1980), .amd paints and inks (Weinburgex and Rea 1982).
Only one study was found which measured consumer exposure to nonylphenol
isomers (Weschler 1984). Indoor-outdoor measurements of noapolar organic con-
stituents of aerosol particles were made in two office buildings* Average
indoor concentrations of nonylphenol isomers were 15 and 30 ng/m , whereas
associated outdoor measurements of nonylphenol were not detected. The author
could not identify the actual source of the isomexs in eithex of the offices
sampled.
3. Environmental Exposure
a. Environmental Release
.Limited information on environmental -releases of noaylphenol during
manufacture or use was located. Table 5 lists levels of nonylphenol which
have been measured in wastewater effluents or untreated waste from various
manufacturing facilities. Garrison and Hill (1972) reported concentrations of
p-nonylphenol in wastes and receiving waters from a carpet yarn mill (Table
5). The authors found an eighty-fold increase in the concentration of 4-
nonylphenol between the treatment pond influent and effluent, which they
attributed to the possible anaerobic bi(degradation of a nonionic surfactant
used in the-washing and drying processes. Shackelford et al. (1983) detected
4 nonylphenol in'.li water samples associated -with various industrial sources
(Table 6), at concentrations ranging from 2 to 1,620 fig/L.
Borg-Warner (1985) reports jig/L levels for 4-nonylphenol in effluent
discharges into the Monongahela River. However, since the effluent is
discharged into the river at a rate of 200 to 450 gal/min. with river flow
averaging 4390 ft^/sec, Borg-Warner (1985) indicate that the effluent is sub-
stantially diluted. Several other studies have identified noaylphenol in
secondary effluents from municipal treatment plants (Ellis et al. 1982), or in
rivers receiving wastewatera from various chemical industries (Moore and
Harasak 1984)- Quantitative determinations were not made in these studies.
Releases of nonylphenol to the environment during the manufacture of
nonionic surfactants will probably occur during the disposal of used noayl-
phenol drums, and the cleaning of equipment fDSEPA 1985a). Used nonylphenol
drams-will probably be landfilled or incinerated. There are no estimates of
the quantities of noaylphenol .that might be released during these processes
(USEPA 19&5a).
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table 5. Levele of Nonylpheftol in Waate*ater Effluent*
So we*
Staple
Reference
10-35 ua/L
0.05 «|/L
0.05
0.06
4.0 »a/L
(4-aonjrlpnehol)
Unknown
Smug* tt«at*«nt platttt
Specialty oheaical
plant
Carpet jratn aiill
tire ttanofaotof ittf
plant
tar pet jam Hill
AWT* Municipal sewage
Secondary effluent
faiterator efflvent
Untreated »a»te
ffaetewater effluent
treatment pond
effluent
Lin et al. 1981
Stephaaon and Oiger 1982
ttitea et al. 1979
Oarrllod and Hill 1972
et al. 1976
Oarriaon and Hill 1972
•Approtieiate concentration.
b Aft « Adrahoed waate treatatent water.
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12
Table 6. Occurrence of 4-Nonylphe«ol in EnviroaBental Saaples (fig/L)
Industry
NonfeTTons metals
Paint -and -Ink
Organic* and Plastics
Inorganic diemicals
Knbber processing
Ante and other
laundries
Alnsiinnsi
Organic -eheBicals
Public-owned
treatnent -votis
NA
.Industry unknown
Frequency
8
2
9
3
. 1
2
3
•4
11
. 1
2
High
Cone.
120
79
469
3
1«17
270
13
109
51
45
32
Median
Cone.
48
44
132
2
1617
242
11
91
4
45
26
Low
Cone.
10
8
8
2
1617
214
7
36
.2
45
20
•NA « not available.
Source: Shaclelford et al. 1983,
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13
Bel cases of nonylphenol during the manuf acture of -phosphite antioxidant
intermediates are expected to be low.. Loases that night occur fxoa storage
drums or equipment cleaning would be to landfill (DSEPA 1985).
b, Jtavironmental fttte
i. Persistence
{*) Biodegradstion
Fischer et ml. (1974. ms reported la IBEMFA3E 1985) studied the bifidegre-
tion of nonylphenol in a closed bottle test for BCD. Iwo ppm nonylphenol was
tested at 20*C with sampling at 0, 5, 15, and 30 days. Zero to 3% BO) removal
-was observed, indicating little ear no degradation.
6af.fney (1976) -reported no degrade-tie*-of 1 mgAL nonylphenol after 135 hr
in doneatic wastewater. or after 24 hr in industrial wastewater, bat he found
45% degradation of the nonylphenol after 135 hr incubation in the industrial
wastewater.
Sundaram aid Szeto (1981) studied the dissipation of nonylphenol in
stream and pond water when incubated in open and closed flasks. Hey found no
transformation -products after open incubation, but an unidentified transforma-
tion product(s) was detected via EFLC in both pond and.stream water after 3
days incubation in the closed system. Photo-oxidation or aicrobial hydroxyla-
tion were suggested as the possible mechanism of transformation. In the same
study the authors found that nonylphenol was rapidly dissipated from poad
water in the presence of sediment, with about 50% of the nonylphenol appearing
in sediment after 10 days, and the remainder undetected in water or sediment.
About 60% of the nonylphenol translocated to the sediment was degraded in 70
days, with no degradation occurring in autoclaved water and sediment samples.
4-Alkylphenol polyethoxylate surfactants are bicdegraded during aerobic
treatment of wastewater by activated sludge to yield 4—alkylphenol mono- and
diethoxylates. Giger et al. (1984) postulate that high levels of 4-
oonylphenol measured in stabilized sewage sludge originate from the alkyl-
phenol ethoxylates. Giger et al. (1984) suggest that the 4-alkylphenol mono-
aad diethoxylates formed during microbial anaerobic degradation of the alkyl—
phenol polyethoxylate surfactants are less biodegradable, and less •water-
soluble, and are partially removed from wastewater by sorption to lipophilio
floes of sludge. To test their hypothesis that anaerobic environments favor
the accumulation of 4—nonylphenol, Giger et al. (1984) conducted controlled
batch experiments with raw and anaerobically stabilized sludge and observed a
4- to 8-fold increase in the concentration of 4—nonylphenol in the stabilized
sludge relative to that originally present in the raw sludge. Batch exper-
iments involving aerobic incubation resulted in increases in 4—nonylnhenol
concentration by only a :f actor of -two.
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14
(b) . Photode gradation
No iarformation regarding the photcdegradation of nonylpienol and its
isomers was found.
(e) Bydxolysi*
No information regarding tie hydrolysis of nonyl;ienol and its isoaers
was f ound.
(d) Other route* of degradation
No other inforstation regarding tie environmental fate of nonylpienol
its isomers was found.
(e) Bioaccamla tioa
Although tie lof P of nonylphenol (4.10) suggests that bioaccaaulation
may occur, tie study of McLeese et al. (1980*) indicates a low bioaccumulation
of nonylphenol in tie saltwater musael, Mvtilus ednlis. Mussel* with valve
leagtis of about 5.0 en were exposed fox four days in static tests at 15°C to
nonylpienol at nominal concentrations of 0.1 and 1*13 mgJL. Nonylpienol in
the «a**els reached a vazivan concentration between one. and two days, and
decreased by four days. Estimated bioconcentration factors (BCF) ranged from
1.4-13. The anthors conclade that due to the low calculated bioooncentration
coefficient (nptake/ezcretion). jionylphenol concentrations in aeawater of leas
than 0.01 ttg/L are not likely to reanlt in significant accumulation in
mussels.
Kawasaki (1980) report* a bioconcentration factor of about 100 for nonyl-
phenol isomers, while Sasaki (1978) listed it as a chemical known to have
little or no bioaccnmnlation.
ii. Transport
(a) Air
No .data were found.
(b) Water
Bite* et al; (1979) measured levels of nonylphenol in treated waatewater
from a specialty chemicals plant which manufactured many products, including
surfactants. Samples were also taken at various stations up- and downstream
from the point where the wastestream entered a river, end in river sediment.
Level* of 0,05 ppm nonylpheuol were measured in the wastewater, bat no nonyl-
phenol waa detected la .either river water or aedimeat aamplea.
Table 7 list* measurement* of nonylphenol in receiving water* downstream
from a carpet yarn mill (Garrison and Hill 1972). The rapid dissolution of
aonylpheaol as it moved downstream from the discharge point indicates dilution
by the water body.
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15
Table 7. -Concentration of 4—Nonylpnenol in Textile Waste
and Receiving Waters
Sample Location Concentration (mg/L)
Plant total untreated waste
Treatment pond effluent
Saiall creek
(1 mi) «
Small river
(1.5 mi)«
Small river
(4.5 »i)«
Savannan River
(6 mi)a
0.05
4.0
3.0
0.2
0.03
0.002
*Distance belov pond discharge.
Source: Garrison and Hill 1972.
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16
In order to study "the fate and persistence of nonyphenol under field con-
ditions, Snndarsm et al. (1980) applied 0.47 L nosy 1 phenol/ha (equivalent to
the seasonal allowable •axiom of Matacil formulations containing nonyl-
phenol) aerially to a mixed coniferous forest. Jtanyl phenol was detected in
water frest a treated streasi immediately following application, sad persisted
for 5 days. .The .highest concentration of nonylphenol detected was 9.1 ppb one
hour after spraying, which decreased to <2.0 ppb in tf hr, and was not detected
at 24 hr. Under the field conditions tested, the estimated half-life of
nonylphenol was about 2.5 hr. The authors assume that the rapid dissipation
of nonylphenol residues in streasi water was due to dilution by water flow.
Other factors which could have contributed to dissipation were suggested as
-surface evaporation, .and codistillation. Nonylphenol WAS detected in only one
streasi sediaient sample (less than 0.10 ppm) four hours following application,
indicating to the authors that diffusion of nonylphenol downward, in'the water
col nan 'would be minimal.
East et al. (1980) fonad sunny Iphennl to disappear rapidly frost aqueous
solution in open tanks, with up to a 90% loss occurring within 48 hr. The
apparent correlation of nonylphenol disappearance with surface area/volume
ratios, aeration, and stirring, suggests that volatilization is the primary
route of dissipation.
Sundaram and Szeto (1981) studied the behavior of nonylphenol in static
aquatic environments using open and closed systems. They found that nonyl-
phenol dissipated in spiked samples of both pond and stream water in open
flasks-with a half-life of 2.5 days. Persistence in closed systems was
longer, with a half-life of 16.5 and 16.3 days estimated for stream and pond
water, respectively. The authors feel that these findings support the con-
clusion that dissipation of nonylphenol in aqnatic systems results from sur-
face volatilization and redistillation.
(c) Soil
Ilngsbary et al. (1981) applied nonylphenol to terrestrial ecosystems at
a rate equivalent to the quantity of nonylphenol applied in allowable maxismm
seasonal sprayings of Hatacil . They were unable to detect nonylphenol in
soil samples from a study plot well exposed to the aerial deposition of nonyl-
phenol. They suggest that nonylphenol .disappears very rapidly from soil via
physical, chemical* or biological processes.
(d) Biota
In the study by Sundaram et al. (1980) nonylphenol residue in -white
spruce foliage reached its highest concentration (18.9 ppm) one hour after
spraying with nonylphenol. Residues declined steadily, and were node testable
after 62 days, with a Aall-life of 2.8 -hr. Quantities of nonylphenol on the
forest floor, if present, were below the levels of detection, indicating a
filtering affect from the foliage (Snadaram et al. 1980).
c. .Environmental Occurrence
A few measurements of nonylphenol in rivers or tributaries; exist -in the
literature, and these are smomarized in Table 8. .Measured values range fa
-------
Table 6. Environmental Levels of Nonylphenoi
Level
Source
Saiaple
Reference
1-2 ppb (winter)
323 ppb
(4-nonylpheaol)
0.5-2.0 ug/La
1.0 ftf/L
Unknowd
0.04-i ppb (stta*er) Onknowtl
Unknown
10 iranicipil
ttettaent piAnti
Wool toooring
plint
Delnrtre It.,
Philadelphia. PA
Delaware ft. •
Philadelphia, PA
Lover Tennessee ft.,
below divert City, tt
Olatt ft.,
Switxerland
Savannah ft. ttibtttarjr
Kites et al. 1979
Bites at al. 1979
Ooodley and Gordon 1976* as reported
ifl CBEKFATfc 1983
Ahel at al« 1983
Gustafson 1970, as reported
in Garrisok and Kill 1972
•Approximate concentration
-------
18
40 ng/L to 1 mg/L. Holies and Xlngsbury (1980* is -reported in Moody et al.
1983) found levels of nonylphenol op to 1.1 ppm in stagnant -water following
operational pesticide spray program in Ontario.
D. Heal-th ^Effects
1. Metabolism
One pha-rmsBoH ue tics study exists (Ebaak «t ml. 1966) describing the
• excretion of G-nonylphenol when administered orally or intraperitoneally to
150 f male rats (Farms-Elias stock). Daily urine and fecal samples were col-
lected and analyzed for a period of 7 days* and 002 samples were collected and
analyzed for 4 days. By day 4 of the 7-day sampling period, the majority of
the labelled nonylphenol -was excreted in urine (19%), and feces (70ft). No
radiolahelled 00, -was detected, identical results were obtained -with both
methods of administration. First-day urine samples were analyzed with ion
exchange chromatography. and 25% of the urinary metabolites of C-nonylphenol
chromatographed as neutrals. The remaining C chromatographed as acids after
the neutrals, and were believed to be mainly glncuronic acid conjugates (75%)
of nonylphenol.
2. Lethality
Smyth et al. (1962, 1969) -report for the mixed isomers an oral ID-0
of 1.62 mL/kg (1537 ag/kg based on a density of 0.949 g/cn) «nd ad
for
rats of 1.62 mL/kg (1537 ag/kg based on a density of 0.949 g/cnf) and a~der»al
ID5Q for rabbits of 2.14 mL/kg (2031 mg/kg based on a density of 0.949 g/cm ).
They list 4 hr as the maximum time to death for rats inhaling a concentrated
vapor. Texaco (1985*) and Monsanto (1985b) list an oral ID., for rats of 0.58
g/kg, and 1300 mg/kg, respectively. Monsanto (1985b) lists a dermal ID_n for
rabbits of X200« mj/kg and" <3160 mg/kj.
3. Oncogenicity
No information.
4. Genotaxicity
No information.
5 . Teratogeni ci ty/fieprcdnctiTe Effect a
Mo information.
6. Other £ffecta
a. Skin -and -Eye Effects
Nonylphenol caused necrosis (graded 6 on a scale of Jr-10) -when applied at
a strength of 10 mg/24 hr to shaved rabbit skin. It caused severe corneal
damage (graded 10 on a scale of 1—10) as a 1% solution applied (0.5 mL) to
rabbit eyes (Smyth et al. 1962. 1969). Nonylphenol produced moderate
-------
19
irritation when 500 ag was applied to -rabbit xkin (UCD8 1959, as reported in
Sax 1984).
Bantuocio et al. (1984) s tidied the irritant potential of nonylphenol
when passaged into shaved rabbit akin daily for 30 days. A 10% solution of
nonylphenol in water (0.5 aL/day) iraa found .to give rise to increased layers
of epidermal cells and increased cells in the superficial deraiis. The abso-
lute f ibroblast count was raised 52ft although the relative count was not
raised. The basement ateabrane was unaltered and the fibers of the den is
showed no gross changes* Elastic fibers had alaiost disappeared. Although
nonylphenol induced changes in the form of increased numbers of epithelial
cell layers* and dermal cell count* the anthors note the difficulty in evalua-
ting the reanlta, and in extrapolating them to .human tissues.
Texaco (19B5b) applied 0.3 j& nonylphenol directly to tie .shared akin of
one male and one female rabbit. The material /remained in contact with the
akin for 4 hr. and akin necroaia waa visible In both rabbits at 48 Jtr after
the application. Texaco (1985a) and Xonsanto (1985b) list a akin irritation
index (based on the Draize Method) for nonylpnenol of 8.0/8.0 and an eye irri-
tation index of 57/110 and 58/110, respectively, for rabbits. Nonylphenol is
listed as a corrosive agent which nay cause burns and blistering to the akin.
It is axtreaely irritating to the eyes, and may cause permanent eye injnry
(Texaco 1985a).
The acute toxicity of 20 conpound a used by the Air Force was studied to
establish safe handling guidelines (Gaworaki et al. 1979, as reported in
MDLARS II [TQXBACK76] 1985). Nonylphenol was reported to canse a skin sensi-
tization reaction in 18 of 20 animals dosed (level of dosing and type of
animals tested not given in abstract)..
Texaco (1985c) tested nonylphenol for akin sensitization using ten male
albino guinea pigs and a modified Jfaehler test method. Under the conditions
of the study, no skin sensitization was observed.
Weiss (1980) states that nonylphenol causes -smarting of the akin and
first-degree burns on short exposure, and aay canse secondary burns on pro
longed exposure. The -vapors .cause a alight, temporary, smarting of the eyes
or respiratory ay stem if preaent in high concentrations.
Cell in et al. (1779) tested tie depigm rating rapacity of -various phenols,
including nonylphenol, using black guinea piga and black adult mice (strains
not given). They report that irritation was observed with all phenols, but
that nonylphenol did not induce depigmenxation.
b. .Biochemical Effects
.; The partitioning: ami interfaclal interaction of fi-adenosine -triphosphate
to various amphiphilea (lipophilic groups attached to amino acid residues) haa
been studied by Eideshima et al. (1977). It was found that 4-nonylphenol did
not directly react with nude otides. probably due to electrostatic repulsion.
In the presence of Ca , interaction did occur, although Mg did not enhance
nacleotide .interaction with nonylphenol.
-------
T. Ctse Seports and "Epidemiological Studies
In • case -report. Sherman (1985) describes multiple birth defects in a
3-week old male infant. Hie mother was exposed to a. polymeric material
applied with • aonylphenolic ethoxylated surfactant.dnrinf tie early part of
her pregnancy.
Xkeda et al. (1970) reported two cases of lencoderma in women engaged in
degreasing metal parts with synthetic detergents containing polyoxyethylene (3
to 16) nonyl- or octylphenylether. Analysis of the detergents rerealed con-
tamination with free alkylphenol, possibly nonylphenol or octylphenol, aid the
authors suspected that the 1 encoderat was caused by the free alkylphenols.
They hypothesized that either a certain portion of the alkylphenols added as a
starting material to fora the detergents remained vnreacted. or decomposition
of the detergents daring their nee yielded free alkylphenols. No posit ire
correlation between the cases of 1 encodetma and nonyl- or octylphenol were
made. No other case report* or epidemic!ogical studies were fonnd specifi-
cally dealing with nonylphenol.
JL. Environmental Effects
1. Metabolism
Uptake (Kl) and excretion (C2) rate constants, time to maximum concentra-
tion* and half—time for clearance of nonylphenol in the saltwater mussel.
Mytilus edulis. were estimated by McLeese et al. (1980a). MasseIs were
exposed for four days in static tests at 15°C to nonyphenol concentrations of
0.1 and 1.13 mg/L of sea water. Maximum concentrations occurred at 0.4 days,
with a II of 23/day. a 12 of 2.3/day. and a half-time for clearance of 0.3
days.
In a static test. McLeese et al. (1981) studied the uptake and excretion
of p-nonylphenol in Atlantic salmon (Salmo salar) that were placed for four
days in water containing p-nonylphenol and then transferred to clean water.
On the first day of exposure, the concentration of nonylphenol in the water
was 0.31 mg/L and the average tisane concentration (uptake) for two fish was
72.7 ftg/g of tissue (wet weight). On day 4, the concentrations had dropped to
0.17 mg/L in the water and 12.7 ng/g of tissue in the fish. Hie excretion of
p-nonylphenol. evaluated on the basis of tissue measurements that were made
after the fish had been placed in clean water, was almost complete by four
days. At that time; the average tissue concentration of nonylphenol had drop-
ped to 0.48 flg/g. No other data on metabolism in aquatic organisms were
found.
2. Lethality
Lethality data for freshwater and saltwater species are listed in
Table 9. It can be seen that nonylphenol is very toxic to all organisms stu-
died, with a range of LC_Q values from 0.13 to 5.0 mg/L. The two bivalves
studied (Anodonta and Mvai were relatively resistant.to nonylphenol toxicity.
Bringsann and Kuhn (1982) report an ECJO value (based on immobilization) of
0.18 «f/L ftff n«ylm4« ma ana. In contrast to. this. Monsanto (19&5a) lists a
-------
21
Table 9. lethality of Jfonylphenol in Environmental Species
Species
LC50
Dose (ag/L) Conditions Reference
Fathead ainaow
(Piaephales trromelas)
Rainbow trout
(Salmo «airdneri)
Brown trout
(Salve linns fontinalis)
Ide
(Leuciscns idns)
Freshwater claa
(Anodonta cataractae)
Water flea
(Daphnia magna)
(P. pulex)
Nonmotile alga
96 hr
96 hr
96 hr«
96 hr«
24 hi*
96 ire
RA
144 hr
24 hr
48 hr
48 hr
24 hr
0.133
0.3
0.23
0.56-0.92
0.484
0.145
1.3
J.O
0.48
0.44
0.14-0.19
1.5
NA»
NA
Si
S
HA
NA
S
HA
NA
S
S
Hoi combe et al. 1984
Monsanto 1985b
McLeese et al. 198 Ob
Ernst et al. 1980
Ernst et al. 1980
McLeese et al. 198 Ob
Knie et «1. 1983
•.
McLeese et al. 198 Ob
Monsanto 1985a
Monsanto 1985a
Ernst et al. 1980
Weinberger and Rea 1982
(Chlorella -pyrenoidosa)
SALTWATER
Atlantic salaon
(Salmo salar)
Sand shrimp
(Crangon seDteasoinosa)
Lobster
(Hoaarus aaericanns)
Soft-shelled clam
(Mva arenaria)
96 hrf
96
96 hr
96 hr
96 hr
0.13-0a9
0.9
0.30
0.40
0.20
360 Jcr >1.0
FT McLeese et al. 1981
S McLeese et al. 198Ob
S McLeese et al. 1981
S McLeese et al. 198Ob
S McLeese et al. 198Ob
McLee*e et al. 198Ob
•FT = flow through tests.
*>NA* not avail able.
cFingerlin$*.
dS = static testa.
eEmbryo*.
^Juveniles.
-------
.22
3. Byproduct!OB
No data were found.
4. Behavior and Growth
Weinberger and fea 119U) studied the -ultrastructural effects of nonyl-
phenol on * no tile flagellate, Chlamvdomouas reinhardii. Chi aired omonas was
exposed for 1 hr to 0.5 to 0.7 ppm nonylphenol added to the nutrient medium.
Nonylphenol was found to distort the flagellae asd to disrupt the.ultrastruc-
tnzal architecture of the cell vails of treated cells.
Matacil 1.8D is a pesticide consisting of the carbaaate aminocarb formn-
lated with nonylphenol asd a fnel oil distillate. 585 diluent oil. Weinberger
and Eea (1981. 1982) exposed Chlorella populations to concentrations of amiuo-
carb as high as 10 ngAmL and recorded growth stimulation, while the sane con-
centration of femulated aaiinocarb in Matacil 1.8D proved lethal to
Chlorella. Nonylphenol -was added to Chlorella culture* at concentrations of
0, 0.025, 0.25. 2.5. 7.5* or 25 fig/at. The average exponential growth rate
was depressed at the fonr lower concentrations, while at 25 ug/aL, 100% kill
was achieved. Frost these experiments a 24 hr LC.Q of 1.5 ug/mL was estimated.
Exposure of populations of Chlorella to diluent 585 oil concentrations as high
as 15 ug/aL resulted in no population growth effects. The authors conclude
that nonylphenol in the f omul a ted pesticide, Matacil 1.8D, is responsible
for the toxic affects seen in their algal growth studies.
Using the flnorcaietric determination of algal photosynthetic activity,
nonylphenol was tested for its ability to inhibit photosynthesis in the green
alga, Chlamvdomona reinhardii after 1 hr of treatment (Moody et al. 1983).
Inhibition of photosynthesis was 54.7% at 0.5 ppn nouyphenol, and 100% at 0.75
and 1.0 ppn. Equivalent concentrations of nonylphenol in the pesticide Mata-
cil 1.8-D produced very similar results, while the carbaaate Matacil . and
diluent 585 oil alone required concentrations of MOO and 30 ppm, respec-
tively, to produce 100% inhibition of photosynthesis.
Six guppi-es and six snails (scientific names not given) were housed in
natural lake water to -which 0.5 ppm nonylphenol was added (Weinberger and £ea
1981). He behavior of the fish and snails was visually monitored. Ihe gup-
pies reacted immediately to the nonylphenol. showing an initial startle reac-
tion, and later some slight disorientation. accompanied by less vigorous
feeding. Iwo of the six gnppies died within 24 hr, and the others recovered
after 36 hr. The snails dropped from the inner surface of the tank and did
not emerge for 8 hr. Following .this, 5 of the snails returned to normal
feeding behavior.
Hoicombe et al. (1984) conducted flow-through acute toxicity tests with
Pimeahales oromelas. .Adverse behavioral effects-were fowmd in fish exposed to
concentrations of nonylphenol greater than the LC_Q (0.135 mg/L). At a con-
centration of 0.187 mg/L, surviving fish were lethargic, although still reac-
ted to outside stimuli such as tapping the tank. At concentrations as low as
0.098 ag nonylphenol/L, some loss of equilibrium was observed in the fish.
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23
Nonylphenol was found to significantly decrease (significant at the 1%
level) percent seed gemination in Jack pine (Finns banksiana) and white birch
(Betula nanvrifera) at 100 ppm, and increase percent seed germination (signi-
ficant at the 1% level) in white birch at 20 ppm (Weinberger and Vladut 1981).
latex uptake was significantly reduced (significant at the 1% level) In Jack
pine by 20 and 100 ppm nonylphenol (50 and 78% reduction, respectively).
I^ngj-fr of sprouts of Jack -pine seeds were decreased by 201 when treated with
100 ppm nonylphenol, and treated seeds gave rise to dwarfed seedlings. A
five-fold reduction (81% decrease) in length of sprouts of white birch
occurred following treatment with 20 ppm nonylphenol (the only level tested).
Axenically cvltnred fronds of Lemna minor were exposed to "ecologically
relevant" concentrations of nonylphenol* aainocarb, 585 diluent oil, and the
Matacil 1.8D foramlation containing all three constitnents (Weinberger and
lyengar 1983, as reported in Jffl)LARS II [MEDLINE] 198JK Frond growth., fresh
and dry weight, chlorophyll content, photosynthesis, and total A1P content
were significantly (level not reported) decreased by exposure to the Matacil
1.8D formulation, but not to aainooarb or 585 oil alone. The anthers arttribu—
ted the toxic effects to nonylphenol.
Inie et al. (1983) studied the effect of 4-nonylphenol on oxygen consamp-
tion in bacterial populations, and report an EC., of >10 ag/JL
Lewis and Jnrd (1972) studied the sporostatic activity of various
phenolic conpounds, including 4-nonylphenol, on Bacillus meaateriua ATCC
10778. 4-Nonylphenol inhibited germination of B. meaaterium in nutrient broth
(99% inhibition at 2 hr) at 32 |ig/-mL, and prevented outgrowth at 10 jig/aL. A
saturated solution of nonylphenol proved ineffective in inhibiting sporostatic
activity after 24 hr incubation. Sporostasis was reversed by washing. Non-
physiological (by-pass) germination was not inhibited. With 4-nonylphenol at
32 |ig/mL, the lysis of 30 to 90% of the spores stopped with a phase-grey
appearance, and the rest of. the spore* remained phase-bright. Based on the
complete inhibition of Sporostasis under good germination conditions at low
concentrations, and the failure to block nonphysiological germination, the
authors suggest that the sporostats studied reversibly. render some proteins
involved in physiological germination nonfunctional.
Term, and Itxkovitch (1976) studied the effects of nonylphenol on the
oxygen uptake of the bacteria Thiobaeillus ferrooridans used in biohydrometal—
lurgical treatment for metal recovery from low-grade sulfide-bearing materi-
als. Surfactants may be adsorbed on the mineral surface during treatment,
wetting the bacteria* and -preventing intimate contact of the bacterium with
the metal surface. They may also influence nutritive oz growth processes by
being adsorbed on the bacterial envelope or by changing the growth environ-
ment. Nonylphenol was found to reduce the surface tension of the reactive
medium and the rate of oxygen consumption of J. farro^MMi^ %y approximately
40%.
5. Population Effects
lingsbury et al. (1981) applied nonylphenol to terrestrial ecosystems at
a rate equivalent to the quantity of nonylphenol applied in allowable maximum
seasonal spraying* of Jfatacil . Ihey found that nonylphenol did not have any
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24
significant (level of significance not specified) effect on insect popula-
tions, forest songbiad populations* ox the ability of songbirds to defend
their breeding territories.
«. Drier Iffects
Borg-^Taraer (1985) studied the factor* affecting mortality in fathead
minnows (PJae-ohales uromelas) during 48-hr LC.Q teats. Grab samples of
effluent containing ug/L concentrations of phenol* 4-nonylphenol and other
nonylated isevers, tert-butylphenol, and amiti-bntylated phenols were used fox
the tests. The wastewater effluent tested is discharged into the Hbnongahela
Hirer.
Liver tissues from surviving fathead minnows exposed to either L(LQ or
LC^Q levels of diluted effluent (the actual concentrations tested are not
given) were studied using transmission electron microscopy. An increase in
lipid droplets and nuclear aberrations was observed. Pathological observa-
tions included expanded rough endoplasmic reticnlum, increased vacuolar and
lysosomal population, and nuclear evagination and distortion. Increased con-
centrations of effluent resulted in increased cellular changes,, indicating a
dose-response relationship. Byperplasia of gill tissue was also observed in
surviving fathead minnows. Because the effluent consisted of .a mixture of
chemicals, the effects observed could not he attributed to any specific agent.
Hoi combe et al. (1984) noticed hemorrhaged areas and bodies swollen with
fluid in Pimenhales uromelas treated with 0.187 mg nonylphenol/L in' acute
flow-through tests.
Dizer et al. (1984) studied the effect of pollutants -remaining in secon-
dary and tertiary treatment waters on adsorption of viruses to sand, an excel-
lent material, for the adsorption of pathogenic -viruses from, contaminated
waters. Experiments in the presence of nonylphenol seem to indicate that
nonylphenol substantially diminished the adsorption of viruses by disrupting
the hydrophobic bonds between the viruses and the substrate.
7. Abiotic Effects
lib data were found.
F. Existing Standards, Regulations, and Recommendations
Proposed guidelines exist which limit nonylphenol effluent discharges
into publicly owned treatment works (POIW) (USEPA 1985b). No other regula-
tions regarding occupational, public, or aquatic exposure to nonylphenol or
its isomers were found in the literature. A taste threshold of 0.001 sig/L for
nonylphenol is given in Daw son et Al. (1970, as reported in Anstern et al.
1975).
A red DOT shipping label is required -for drums, tank ears and tank trucks
containing nonylphenol (Lowenheim and Koran 1975).
-------
25
U, References
A. .Literature Cited
Note: Section 8(e) or TYI (Fox Tour Information) submissions cited in this
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-------
28
McLeeseDW, Zitko V, Met calf e O), Sergeant DB. 198 Ob. Lethality of aminocarv
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-------
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32
B. Supplemental Information
The followinj organizations responded to the Agency's request for information
on nonylphenol for this Chemical Hazard Information Profile:
Submitter Dame: Borg-Warner Chemicals. Inc.
EPA Document Control Number: FYI-OTS-0885-0438 INIT (Sequence A)
.Information Types: Results of studies observing factors affecting the
mortality of fish during acute static
LC10 *ad LCjQ.-testing.
Submitter Name: Occupational Physician
EPA Document Control Number: FYI-OTS-0585-0402 FLWP (Sequence V)
Information Types: Possible cause-effect relationship between product
containing nonylphenol and .multiple birth defects.
Submitter Name: National Institute for Occupational Safety and Health
EPA Document Control Number: FYI-OTS-0585-0402 FLWP (Sequence C)
Information Types: No information in the NIOSH Current Research File
Submitter Name: national Toxicology Program
EPA Document Control Number: FYI-OTS-0585-0402 FLWP (Sequence D)
Information Types: None of the nonylphenols tested or selected for testing
by the NIP.
Submitter Name: Borg-Warner Chemicals, Inc.
EPA Document Control Number: FYI-OTS-0685-0402 FLWP (Sequence E)
Information Types: Uses of nonylphenol
Submitter Name: Schenectady Chemicals, Inc.
EPA Document Control Number: FYI-OTS-0685-0402 FLWP (Sequence F)
Information Types: Production volume, uses, manufacture, and exposure to
nonylphenol
Submitter Name: Xonsanto Industrial Chemicals Co.
EPA Document Control Number: 171-015-0685-0402 FLWP (Sequence G)
Information Types: Product description, environmental effects, worker and
environmental exposure, JCDS for nonylphenol
Submitter Name: Monsanto Industrial Chemicals Co.
EPA Document Control Number: FYI-OTS-0685-0402 FLWP (Sequence H)
Information Types: Production volume data claimed as confidential
Submitter Name; Texaco Chemical Co.
EPA Document Control Number: PYI-OTB-0685-0402 FLWP (Sequence I)
Information Types: Dermal toxieity data
Submitter Name: Occupational Physician
EPA Document Control Number: FYI-OTS-0885-0402 TLWP (Sequence J)
Information Types: Clinical report describing multiple birth defects
-------
in diild Trhose -mother was exposed to a chenical
containing ethylen* oxide; bibliography included
SnhBitter Nane: . Office of Pesticides Programs. U.S. -Environmental
Protection Agency
-Information Types: The OPP reports that polymeric aaterials containing
nosylphenol are used as inert ingredients in
pesticide femulations; no other inforaation
available on nonylphenol
He following costpaaie* stated, in response to theTJSEPA reqvest. that they
had no unpublished technical bulletins or reports on nonylphenol:
Celanese Corporation, New Tori* NT
E. I. Dn Pont Je Neaonrs 4 Co.. Wilmington. D£
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34
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Reznik RB, Eimutis EC, Delaney JL et al. 1978. Source assessment: priori-
tization of stationary water pollution sources. Washington. DC: U.S. Environ-
mental Protection Agency. J3PA-6 00/2-78—004 q..
"Ross RE, Kemp HT, Syon IE, Haamons AS, Ensminger JT. 1979. Chemicals tested
for paytotoxicity, vol. 1 and 2. Oak .Ridge. IN: Oak Ridge National Labora-
tory. QBNL/-EIS-1S5.
Sawicki E. 1982. Handbook of environmental genotoxicology, -vol. 1. Environ-
mental aspects. Cleveland, OH: Chemical Rubber Company Press.
Sax NI. 1984. Dangerous properties of industrial materials, 6th ed. New
York: Tan Nostxand Reinhold Company.
Sax NI. 1981. Caacer cansing chemicals. New York? Tan Nostrand Reinhold
Company.
Searle CE, ed. 1976. . Chemical carcinogens. ACS monograph 173. Washington,
DC: American Chemical Society.
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38
Shackelford WM, leith LE. 1976. Frequency of organic compounds identified in
water. Athens, GA: Office of Research and Development, U.S. Environmental
Protection Agency. EPA-600/4-76-062.
Shepaxd TEL 1980. Catalog of teratogenic agents. Baltimore, •>: Johns Hop-
kins University Press.
Sittif X. 1975. Environmental sources and emissions handbook. Park Ridge,
NT: NoyesData Corporation.
Sittif M, 1981. Handbook of toxic and hazardous chemicals. Park Ridge, NT:
Noyes Data Corporation.
Tatken £L, Lewis IT. Sr. 1983. Registry of toxic effects of ciemical snb-
. stances. Cincinnati, UH: National Institute fox Occupational Safety and
Health.
USEPA. 1976. U.S. Environmental Protection Agency. Chemicals-which hive
been tested fox nenrotoxic effects. Washington, DC: U.S. Emrironatental Pro-
tection Agency, EPA 560/1-76-005.
USEPA. 1979. U.S. Envixonnental Protection Agency. Tbxicology hand book.
•aamalian and aquatic data, books 1 and 2. Washington. DC: U.S. Environmen-
tal Protection Agency. £PA-540/9-79-003 JEk 1, Parts 1 and 2. and Bk 2. PB 80
196884.
USEPA. 1980. U.S. Environmental Protection Agency. Chemical hazard informa-
tion profiles (CHIPs). Angnst 1976 - August 1978. Washington, DC: U.S.
Environmental Protection Agency, Office of Pesticides and Toxic Substances.
EPA-560/11-80-011
USOSHA. 1983. U.S. Occupational Safety and Healtn Administration. Toxic and
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2nd ed. Now York: Tan Nostxand Reinhold Company.
Weast EC. Astle IT, eds. 1985. Handbook of data on organic compounds, vols.
I and Jl. Boca .Raton, XL: CKC Pxess.
Weber 1C, Parker PA, Bowser M. 1981. Vapor pressure distxibntion of selected
organic chemicals. EPA 600/2-81—021
Weiss 6. ed. 1980. flazazdons chemicals data book. Park Ridge, NT: Noyes
Data Corporation.
Williams HT. 1949. Detoxication mechanisms. The -metabolism of drugs .and
allied organic compounds. New Toxk: John Wiley .and Sons. Inc.
Windholz H, ed. 1983. The Merck Index. An encyclopedia of chemicals and
dxngs, 10th ed. Jtahway, NT: Merck and Company.
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39
2. Data Dares
File
Nosylphenol (aized isoners);
4—Nonylphenol; 2—Nonylphenol
HDLARS
T03L1NE 79-
TOI65
TOI76
KB)LIN£
BACKS 0
BJKX77
BACC75
BACC71
BACC46
CANCERL1NE
CANCEKPROJ
TDB
KTECS
CHEMLBJE
LOOHEH) DIALOG
BIOSIS PREVIEWS 69-76
BIOSIS PREVIEWS 77-80
BIOSIS PREVIEWS 81-
CHE1L EXP. 74-
CONG. KEC. ABSTR. 76-
FH>. SBB. ABSIR. 77-
FH). RES. FROG. 82-
NTIS 64-
Np«ber of References Pate of Search
83
40
64
2
3
0
1
0
0
0
0
2
1
3
6
14
24
0
0
0
0
5
April 1. 1935
3. Seardi Strategy
databases listed above vere searched using CAS Registry ttmbez. ch
ical naae, and synonyau listed in the CBEML1NB printout. ¥ith the exception
of the searches on the Cheat Abstr files which were limited to non-patent
references, all hits were 'Uaatped" aad computer printouts scanned-for per-
tinent references.
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40
D. Chemical Specific Sources Searched
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manufacturing air emissions - overview and prioritization. Washington, DC:
U.S. EnviTonmental Protection Agency. EPA 600/2-78-004d.
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Guenzi W, ed. 1974. Pesticides in soil and water. Madison, WI: Soil
Science Society of America.
Hayes WH Jx. 1975. Toxicology : Williams and
Wilkins Company.
Martin B, Worthing CR, eda. 1974. Pesticide manual. British Crop Protection
Council.
Menxie CM. 1969. Metabolism of pesticides. Special scientific report -
Wildlife No. 127. Washington, DC: U.S. Department of the Interior, Bureau of
Sport Fisheries and Wildlife.
Overcash MR, ed. 1981. Decomposition of toxic mad nontoxie organic compounds
in soils. Ann Arbor, MI: Ann Arbor Science.
Royal Society of Chemistry. 1983. The agrochemicals handbook. Nottingham,
England: Royal Society of Chemistry.
Thomson WT. 1982. Agricultural chemicals. Book 1 - Insecticides, acara-
cides, ovicides, .1982-1983 Revision. Fresno. CA: Thomas Publications.
USEPA. 1979e. U.S. Environmental Protection Agency. Water-related environ-
mental fate of 129 priority pollutants. A literature search. VI. Phenols.
cresols, and monocyclic aromatics. Draft report. Washington, -DC: U.S.
Environmental Protection Agency. Contract 68—01-3852.
USEPA. 1979f. U.S. Environmental Protection Agency. Water-related environ-
mental fate of 129 priority pollutants. A literature search. VII. Pesti-
cides. Draft report. Washington, DC: U.S. Environmental Protection Agency.
Contract 68-01-3852.
Vettoraxxi 6. 1979. International regulatory aspects for pesticide chemi-
cals, -vol. 1. Boca Raton, PL: CRC Press.
Wagner SL. 1983. Clinical toxicology of agricultural chemicals. .Pa-rk Ridge,
IL: NoyesData Corporation.
Ware GW. 1978. The pesticide book. San Francisco: W. B. Freeman and Com-
pany,
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41
ITinresser U. ed. 1976. Pesticide index. College P«xk. JO: Entomological
Society of
£EL 1979. Pe*ti«ide aumal, «ti ed. British Crop Protection Coim-
cil.
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