Environmental Protection Agency
Office of Enforcement
TOXICITY OF ORGANIC COMPOUNDS
FOUND IN
PETROCHEMICAL EFFLUENTS
August 1976
National Enforcement Investigations Center
Denver, Colorado
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CONTENTS
INTRODUCTION 1
TOXICITY INFORMATION 4
Acenaphthene 4 1-Methylnaphthalene ... 12
Butyl phenol 4 Naphthalene 12
2-sec-Butylcyclohexanol ... 4 n-Nonacosane 12
Cyclohexanone 5 2-Nonanone 12
2-Cyclohexylcyclohexanone . . 6 n-Octacosane 13
Cyclohexyl chloride 7 n-Pentacosane 13
Dichlorobenzene 7 Phenanthrene 13
1,4-Dimethylcyclohexane ... 8 Phenyl Ether 13
3,6-Dimethyl-6-isopropyl- RDX 13
2-cyclohexanone 8 stilbene 15
2,5-Dimethyltetradecane . . 8 styrene 16
Diphenyl 9 TNT _ _ 17
w-Dotriacontane 9 n_Je'tr'ac'os'an'e ' .' .' .' .' \ 19
Ethoxyethyl acetate 9 n.TetratriaContane ... 19
Ethyl phthalate 9 T . . nn
J K n-Tnacontane 19
Bis-(2-ethylhexyl) Fumarate .10 _ . ., .,. 0_
J J Trichloroamline .... 20
n-Hentriacontane 10 T . ,, , _.
Trichlorobenzene .... 20
n-Heptacosane 10 T . .,
n-Tricosane 21
n-Hexacosane 10 _ .. . . 0_
n-Tritriacontane .... 22
1-Methylfluorene 10
Methylindole 11
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INTRODUCTION
The National Enforcement Investigations Center has assessed the
toxicity of organic compounds found in effluent discharges from the
petrochemical industry. Among the on-line, bibliographic computerized
data bases used to locate information on the various compounds were
ENVIRONS, TOXICON, AMIC, MEDLINE, WIRSIC, EIS, Biological Abstracts and
Chemical Abstracts. A profile was created in which the compound names
were weighted against these terms:*
Aquatic
Bay
Bays
Biochem Oxygen Demand
Biochemical Oxygen Demand
Biol Oxygen Demand
Biological Oxygen Demand
B.O.D.
BOD
Brook*
Canal
Canals
Chem Oxygen Demand
Chemical Oxygen Demand
Coast
C.O.D.
COD
Contaminated Discharge*
Creek*
Delta
Deltas
Degener*
Degrad*
Disposal
Effluent*
Environmental Hazard*
Estuar*
Fate
Fresh Water*
Freshwater*
Gulf
Houston Ship Channel
Industrial Discharge*
Intertidal
Lagoon*
Lake*
Legal Tolerance*
Littoral
Marine*
Municipal Discharge*
Natural Water*
Ocean*
Outfall*
Persistence
Pond
Ponds*
Residue*
River*
Rivulet*
Salt Water*
Saltwater*
Sea
Seas
Seawater*
Sewage
Sewerage
Shallow water*
Stream*
Surface Water*
Surfacewater
Tidal
Tide
Tides
TOD
T.O.D.
Total Oxygen Demand
Tributar*
Water Way*
Waterway*
Waste*
Water Pollut*
Waters*
* Words followed by an asterisk received a "stem search* " meaning that
all endings such as singular^ plural^ participial and adverbial were
searched.
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Of the 108 references found for 70 compound names, 13 names were
cross-referenced and no specific information was found for 30 compounds.
This report contains information available as of July 1974 on the
adverse effects of these 40 compounds:
t
Acenaphthene
Butyl phenol
2-sec-Butylcyclohexanol
Cyclohexanone
2-Cyclohexylcyclohexanone
Cyclohexyl chloride
Dichlorobenzene
1,4-Dimethylcyclohexane
3,6-Dimethyl-6-isopropyl-2-cyclohexanone
2,5-Dimethyltetradecane
Diphenyl
n-Dotriacontane
Ethoxyethyl acetate
Ethyl phthalate
Bis-(2-ethylhexyl) Fumarate
n-Hentriacontane
ft
n-Heptacosane
rc-Hexacosane
1-Methylfluorene
Methylindole
1-Methylnaphthalene
Naphthalene
n-Nonacosane
2-Nonanone
n-Octacosane
n-Pentacosane
Phenanthrene
Phenyl Ether
RDX
Stilbene
Styrene
TNT
n-Tetracosane
n-Tetratriacontane
n-Triacontane
Trichloroaniline
Trichlorobenzene
n-Tricosane
4-4.
n-Tritriacontane
Xylene
t Cross-referenced under Cyclohexanona
tt Cross-referenced under n-Tricosane
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There was no specific information for these 30 compounds, even
though they were found in discharges from the petrochemical industry:
Acenaphthalene
1-Bromo-2-chlorobenzene
Cadalene
m-Chloroaniline
Chloroheptadecane
Chlorohexadecane
Diisobutyl phthalate
1,4-Dimethylnaphthalene
1,6-Dimethylnaphthalene
2,2-Dimethyloctanol
4,4-Dirnethyl -1 -pentene
Di-n-butylketone
Di-n-octyl-phthalate
Di-(-2-ethylhexyl)adipate
1,11-Dodecadiene
2-Ethyl-l-Hexanol
FT uorocyclohexane
Hexamethylbenzene
Indene
2-Isopropyl-l,3-dioxolane
Isopropylnaphthalene
1-Methoxy-1-octooxyethane
3-Methylindene
2-Methylindene
Methyli sopropylnaphthalene
2-Methylnaphthalene
p-(l,1,3,3-tetramethylnaphthalene)-Phenol
Trimethylnaphthalene
2,3,4-Trithiopenthane
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TOXICITY INFORMATION
ACENAPHTHENE Used as an insecticide and fungicide.
Merck Index, 1970
N. Marimuthammal. Mutagenesis of Sugar Cane. 1.
Effects of Chemical Mutagens. Proceedings of Indian
Academy of Science Section B 68(S):131-142, 1968
J. F. Mesquita. Alterations of Cell Division in
Allium cepa Root Meristen Cells Treated with Acenaph-
thene, C. R. Academy of Sci. Ser. D 265(4): 322-325,
1967
BUTYLPHENOL May be irritating to eyes and mucous membrane.
Merck Index, 1970
2-sec-
BUTYLCYCLOHEXANOL
This compound is a metabolite of butylcyclohexanone.1
Cyclohexanol, like cyclohexanone, is a moderately
toxic compound that possesses a high degree of
cytogenetic activity. Savelova, Bruk, Klinkinan and
Russkikh, based on toxicological considerations,
recommended 0.5 mg/1 of cyclohexanol in water be
adopted as the limit of allowable cyclohexanol
concentration in natural basin water.2 However,
more recent experiments have shown that cyclohexanol
is a cytogenetic metabolite of cyclamate which has
been banned for human consumption. In vitro ex-
periments on human leukocyte cultures with cyclo-
hexanol showed the cytogenetic effects of chromosome
breaks, deformities, size abnormalities and achroma-
tism.3 Cyclohexanol had a thermodynamic activity in
the range of 0.001 to 0.1 which gave a threshhold
narcosis 50 toxicity to barnacle larvae with active
appendages, but no forward movement in Elminius
modistus larvae after 15 minutes.4
1 K. L. Cheo, T. H. Elliott and H. C. Tao. The
Metabolism of Isomeric Tertbutylcyclohexanones. J.
of Biochemistry, 104:198-2043 1967
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2 V. A. Savelova, E. S. Bruk, M. V. Klinkinan and
V. V. Russkikh. Experimental Determination of the
Limit of Allowable Cyclohexanol Concentration in
Natural Basin Water. USSR Literature on Water
Supply and Pollution Control, 5:40-58, 1966, US
Dept. of Commerce
3 J. P. Collin, E. P. Gondry, J. Lederer and A. M.
Pottler-Arnould. Cytogenetic and Teratogenio Action
of Cyclamates and its Metabolites. J. of Thera-
peutique, 47:357-363, 1971
J. P. Collin. Cytogenetic Effect of Sodium
Cyclamate, Cyclohexanone, and Cyclohexanol, in
French. Diabete, 19:215-221, 1971
14 D. J. Crisp, A. 0. Christie, and A. F. Ghobashy.
Narcotic and Toxic Action of Organic Compounds on
Barnacle Larvae. Compendium of Biochemistry and
Physiology, 22:629-649, 1967
CYCLOHEXANONE Cyclohexanone has rather moderate toxicity but it is
extremely potent cytogenetically. For example, its
median lethal dose to rabbits is 1,000 ppm, to mice
1,950 ppm, and to rats 3,460 ppm.1 Vertebnaya and
Mozhaev likewise reported cyclohexanone to be a
ketone of low sanitary-toxicological characteristics
and suggested a limit of 1 mg/1 in water basins.2
However, more recent experiments have shown that
cyclohexanone is a cytogenic metabolite of cyclamate
which has been banned for human consumption. In
vitro experiments on human leukocyte cultures with
cyclohexanone showed the cytogenic effects of
chromosome breaks,' deformities, size abnormalities
and archromatism.3 In animal experiments, cyclo-
hexanone has been found to be a potent inducer of
cataracts.H With a thermodynamic activity in the
range of 0.001 to 0.1, cyclohexanone gave a thresh-
old narcosis 50 toxicity to barnacle larvae with
active appendages but with no forward movement in
Elminius modestus larvae after 15 minutes.5 The
biochemical purification of caprolactani wastes
in the presence of domestic sewage reduced the con-
centration of cyclohexanone from 180 mg/1 to nil.6
In die-away tests at about 18°C in a dilution water
seeded with acclimatized activated sludge, 60 or 200
mg/1 of cyclohexanone as sole carbon source was
readily degraded, and COD removal was 96% in 2
days.7
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1 Technical Assistance Data System: 72T16661,
ENVIRONS, EPA
2 P. I. Vertebnaya and E. A. Mozhaev. Limits of
Allowable Concentrations of Methylethylketone and of
Cyclohexanone in Water Basins, USSR Literature on
Water Supply and Pollution Control, 2:30-34, 1962,
US Department of Commerce
3 J. P. Collin, E. Condry, J. Lederer and A. M.
Pettier-Arnould, Cytogenetic and Teratogenic Action
of Cyclamate and its Metabolites. Therapeutique,
47:357-363, 1971
J. P. Collin, Cytogenetic Effect of Sodium Cyclamate,
Cyclohexanone, and Cyclohexanol, in French. Diabete,
19:215-21, 1971
** R. H. Rengstorff, J. P. Petral and V. M. Sim.
Cataracts Induced in Guinea Pigs by Acetone, Cyclo-
hexanone and Dimethyl Sulfoxide. Am. J. Optom.,
49:308-29, 1972
5 D. J. Crisp, A. 0. Christie and A. F. Ghobashy.
Narcotic and Toxic Action of Organic Compounds on
Barnacle Larvae. J. Compendium of Biochemistry and
Physiology, 22:629-649, 1967
6 E. M. Arnoldov. Purification of Waste Waters and
the Construction of Purification Installations at
Enterprises of the Chemical Industry of the Donets
Council of National Economy. Ochistka Ispolz. Stochn.
Vod. prom. Vybrosov, Kiev, in Russian, 1964, 40-45;
Chem. Abstr. 63:11158, 1965
7 P. Fitter and M. Kozderkova. Relation Between
the Molecular Structure and Biological Degradability
of Organic Compounds. 1. Biodegradability of
Hydroaromatic and Cycloaliphatic Compounds by
Activated Sludge. Sb. vys. 3K. Chem.-Technol. Prase
16:53-72, 1971
2-CYCLOHEXYL- See CYCLOHEXANONE
CYCLOHEXANONE
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CYCLOHEXYL Has suffocating odor.1 The mosquito fish, Gambusia
CHLORIDE affinis had a TLM96 of 15 ppt.2 Experimental
animals exposed to 0.25 to 25 mg/1 for six months
exhibited disturbed conditioned reflexes.3
i
Merck Index, 1970
2 J. E. Wallen3 W. C. Greet? and E. Lasater. Stream
Pollution Toxicity to Gambusia affinis of Certain
Pure Chemicals in Turbid Waters. Sewage and In-
dustrial Wastes 29(6):695-7113 1957
3 V. N. Orlavskii. Effect of Chlorocyclohexane on
the Organoleptic Properties of Water and the Sani-
tation Conditions of Water Basins (in Russian).
VOPR3 Gig. NASELEN. NEST. 4:199-203, 1963
DICHLOROBENZENE
Can cause injury to livers and kidneys. High con-
centrations cause CNS depression.1 In pure cultures
of the following marine plankton, no growth occurred
but organisms were viable at 13 ppm: Protococcus
sp., Chlorella sp., Dunaliella euchlora, Phaeo-
dactylum tricornutum, and Monochrysis lutheri.2 The
toxicity of chlorobenzene and cichlorobenzene is on
the same level; increasing the 'tuber of chlorine
atoms in a benzene molecule do, not affect the
toxic action but affects only the degree of ex-
pressivity. In larger doses, the toxicity of di-
chlorobenzene depends more on the spatial dis-
tribution of chlorine atoms rather than their number;
e.g., the ortho-isomer is more toxic than the para-
isomer. In determining the maximum permissible
concentrations of these compounds in bodies of
water, chronic experiments were conducted with white
rats to study acute intoxication, their effects on
higher nervous activity, erythropoiesis, urinary 17-
ketosteroids, and carcenogenic action. The action
of the compounds was practically the same. Con-
ditioned reflex activity was depressed showing a
cerebral cortical effect; erythropoiesis was sig-
nificantly decreased, with chlorobenzene producing
eosinophila and ortho-dichlorobenzene, neutropenia.
Ortho-dichlorobenzene, more than chlorobenzene, led
to a sharp rise in urinary steroids. Although both
benzenes increased, tissue acid phosphatase and
sharply decreased tissue alkali phosphatase, no sign
of carcenogenic action was found macroscopically,
histologically, or histochemically. The maximum
permissible concentration according to organoleptic
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effect for chlorobenzene was determined to be 0.01
mg/1; for ortho-dichlorofaenzene, 0.002 mg/1; and for
para-dichlorobenzene, also 0.002 mg/1.3
1 Merck Index, 1970
2 R. Ukeles. Growth of Pure Cultures of Marine
Phytoplankton in the Presence of Toxicants, Applied
Miorobio. 10(6) :532-53?', 1962
3 5. P. Varshavskia. The Comparative Sanitary and
Toxicological Characteristics of Chlorobenzene and
Diehlorobenzene (Ortho- and Para-Isomers) from the
Point of View of Sanitation of Water Reservoirs. In
Russian, Gigiena i Sanit. 33(10):15-21, 1968
1,4-DIMETHYL-
CYCLOHEXANE
No information has been received on this compound.
However, its toxicity will be similar to that of
cyclohexane. Fathead minnows had a TLM96 of 30 ppm
to cyclohexane; bluegills had a TLM96 of 31 ppm;
goldfish had the TLM96 of 33 ppm; and guppies had a
TLM96 of 48 ppm.
Technical Assistance Data System:
VIRONS, EPA
72T16659, EN-
3,6-DIMETHYL-
6-ISOPROPYL-
2-CYCLOHEXANONE
2.5-DIMETHYL-
TETRADECANE
2-cyclohexanone is a fungal metabolite of cyclo-
hexene which can be further reduced enzymatically.
P. K. Bhattacharyya and K. Ganapathy. Micro-
biological Trends, Formations of Terpenes. VI.
Studies on the Mechanism of Some Fungal Eydroxy-
lation Reactions with the Aid of Model Systems. The
Indian J. of Biochemistry, 2:137-145, 1965
E, Boyland and L. F. Chasseaud. Enzymes Catalyzing
Conjugations of Glutathione with Alpha, Beta-Un-
saturated Carbonyl Compounds. Biochemistry J.,
109:651-661, 1968
See n-TRICOSANE
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DIPHENYL CNS depression, paralysis, and convulsions have
been observed in experimental animals.
Merck Index, 1970
Additional information:
R. Viviani, G. Crisetig, V. Petruzzi, and P. Cortesi,
Residues of Polychlorinated Biphenyls in Muscle
Tissue of Clupeoid Fish in the Adriatic Sea. In
Italian, Atti Soc. Ital. Sci. Vet. (ASISAI) 25:429-
433,, 1971
J. L. Mosser, N. S. Fisher and C. P. burster. Poly-
chlorinated Biphenyls and DDT Alter Species Composition
in Mixed Cultures of Algae, Science 176(4034):533-
536, 1972
D. J. Wilpish. Poly chlorinated Biphenyls (PCBs) in
Seawater and Their Effects on the Reproduction of
Gammarus oceanicus, Bulletin of Environmental
Contamination and Toxicology 7(2):182-187, 1972
n-DOTRIACONTANE See n-TRICOSANE
ETHOXYETHYL
ACETATE
This compound is commonly known as Cellosolve
acetate. It is produced by the Dow Chemical
Company, Midland, Michigan; Eastman Kodak Company,
Kingsport, Tennessee; Union Carbide Corporation,
South Charleston, South Carolina; and the 01 in
Corporation, Brandenburg, Kentucky.1 In spite of
its intensive production and common availability, no
references to its aquatic toxicity have been located.
1 Technical Assistance Data System:
ENVIRONS, EPA
72T16721,
ETHYL The lethal dose orally in rabbits is 1.0 g/kg.1
PHTHALATE Chronic toxicity tests with phthalic acid, to which
ethyl phthalate will hydro!ize in water, on lab-
oratory animals at an exposure rate of 0.56 mg/kg
daily for 6 months reduced thrombocyte concentra-
tions, increased bilirubin excretion and caused
morphological changes in internal organs. Based on
this test, a maximum permissible level of phthalic
acid in reservoir water was set at 0.5 mg/1.2
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1 Merck Index, 1970
2 K. F. Meleshchenko, N. V. Mironets, and R. K.
Rozhkoveiskaya. Experimental Data to Substantiate
the Maximum Permissible Concentration of Phthalic
Acid (Phthalic Anhydride) in Water Reservoirs. In
Russian, Gigiena i Sanit. 32(8):12-15, 1967
Additional Information:
K. F. Meleshchenko. Maximum Permissible Concentration
of Phthalic Acid (Phthalic Anhydride) in Water
Bodies. Gigiena i Sanit. 22:167-171, 1967
bis-
(2-ETHYLHEXYLT
FUMARATE
This compound is an ester which is an extremely
effective mosquito repellent, having a space residual
time of at least 100 days.
H. Gouck, T. P. McGovem and M. Beroza. Chemicals
Tested as Space Repellents Against Yellow Fever
Mosquitoes. I. Esters. J. Econ. Entomol., 60:1587-
1590, 1967
n-HENTRIACONTANE See n-TRICOSANE
n-HEPTACOSANE See n-TRICOSANE
rc-HEXACOSANE See n-TRICOSANE
1-METHYLFLUORENE
This compound, also known as ortho-biphenylenemethane,
biphenylenemethane or 2, 2-p-methylenediphenyl (CAS
Registry No. 1730376), has intense antitumor activity
in many of its derivatives.
K. Agrawal. Fluorene Derivatives for Antitumor
Activity, J. Med. Chem. 10(1):99-101, 1967
E. L. Pan and T. L. Fletcher. Derivatives of Fluorene
XXI. New halogenofluorenes. II. Further Potential
Antitumor Agents, J. Med. Chem., 8(4).: 491-497, 1965
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H. L. Pan and T. L. Fletcher, Derivatives of Fluorene
XXX. Rearrangement and Antitumor Activities on Some
9-Oxo-fluorene Oximes. 1. 6 5H~Phenanthridinones,
J. Med. Chem., 12(5) :822-825, 1969
METHYL INDOLE There are several methylindoles, the most common
being 3-methylindole, also known as skatole, which
is infamous because it is the aromatic fraction
which gives feces their distinctive aroma.1 In
addition to the distinctive aroma, indoles have been
implicated in arthritis. A single injection of 0.26
ymoles of skatole once a week for 6 weeks elicited
chronic arthritis. The arthritogenic effect of
indolic substances is related to their lipophilic
activity, which facilitates the diffusion of such
substances into the synovia! membranes.2 The
indoles have a negative effect upon tissue respir-
ation by inhibiting cerebral oxygen consumption at
concentrations below the pathological range.3 In
carefully controlled studies, compounds similar to
the indoles which might be suspected of producing
the noted effects were found not to have arthrito-
genic properties.4 The indoles have also been
implicated in pulmonary edema and emphysema.5
1 Technical Assistance Data System: 72T16884,
ENVIRONS,, EPA
2 J. Nakoneczna, J. C. Forbes, and K. Rogers.
Arthritogenic Effect of Indole, Skatole, and Other
Tryptophan Metabolites in Rabbit . Amer. J.
Pathol., 57.-523-538., 1969
3 P. T. Lascelles and W. H. Taylor. The Effect
Upon Tissue Respiration in vitro of Metabolites
Which May Accumulate in Hepatic Coma. J. Olin.
Sci., 35:63-71., 1968
4 K. S. Rogers, J. C. Forbes and Nakoneczna.
Arthritogenic Properties of Lipophilic., Aryl Mole-
cules. Proc. Soc. Exp. Biol. Med., 131:670-672,
1969
5 J. R. Carlson, M. T. Yokoyama and E. Dickinson.
Induction of Pulmonary Edema and Emphysema in Cattle
and Goats with 3-Methylindole. Science, 176:298-
299, 1972
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1-METHYL-
NAPHTHALENE
Probably toxic.
Merck Index, 1970
NAPHTHALENE
A large dose by ingestion, inhalation, or skin
absorption causes nausea, vomiting, headache,
diaphoresis hematuria, hemolytic anemia, hepatic
necrosis, convulsions and coma.1 The fish, Gambusia
affinis, in static acute bioassay had a TLI\8 of 165
ppm.2
i
Merck Index, 1970
2 I. E. Wallen, W. C. Grier and R. Lasater.
Toxicity to Gambusia affinis of Certain Pure Chemi-
cals in Turbid Waters, Sewage and Industrial Waste
29(6):695-711, 1957
Additional Information:
B. De Jong. Contamination of Ground Water by
Organic Substances in the Intake Area of Two Water
Works. In German, Vom Wasser (VJWWAU) 38:141-156,,
1971
n-NONACOSANE See n-TRICOSANE
2-NONANONE This compound has very potent biological activity as
it is closely related to an alarm pheromone produced
by the ant, Iridomyrmex pruinosus. 2-heptanone is
produced by this species as an alarm pheromone.
Laboratory and field studies with 2-nonanone showed
it to be an alarm behavior-producing agent of
similar activity to 2-heptanone.1 In studies on the
growth of the fungus Dipodascus aggregatus in
culture media containing 2-nonanone there was an
insignificant increase in growth.2
1 M. S. Blum Thomas, S. L. Warter and J. G. Trayn-
ham. Chemical Releasers of Social Behavior. VI.
The Relaxation of Structure to Activity of Ketone as
Releasers of Alarm for Iridomyrmex pruinosus. J.
Insect Physiology, 12:419-427, 1966
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2 A. Hyman. Affect of Various Aliphatic Aldehydes
and Related Compounds on the Growth of Dipodascus
aggregatus. 3. Physiology of Plants, 22:1322-1328,
1969
n-OCTACOSANE See n-TRICOSANE
n-PENTACOSANE See n-TRICOSANE
PHENANTHRENE
Compound can cause photosensitization of skin and is
considered a carcinogen.
Merck Index, 1970
Additional information:
B. H. Grossmann. Therapeutic Effects of Fluorene,
Phenanthrene, and Xanthrene Derivatives on Fungal
Diseases of Tomato, Nature 227(5264):1267-1268, 1970
PHENYL ETHER
Chronic toxicity to warm blooded animals of 2.0 mg/kg
daily was an ineffective dose during sanitary
toxicological tests.
G. F. Amirkhanova and Z. V. Latypova. Experimental
Basis for the Maximum Permissible Concentration of
Diethyl Ether in Reservoir Waters. In Russian,
Prom. Zagryazneniya Vodoemov No. 9:148-157, 1969
RDX RDX is also known as Hexahydro-1,3,5-trinitro-s-
triazine, cyclotrimethylenetrinitramine, cyclonite,
and hexogen. In a case of accidental industrial
poisoning with RDX, human subjects lapse into un-
consciousness with no advance warning. Unconscious-
ness lasted from several minutes to 24 hours, and
upon recovery there were headaches, periods of
stupor, nausea, disorientation, vomiting and weak-
ness. No other abnormal physical findings were
found, and there were no changes in the blood or
urine. Treatment was supported and recovery was
apparently complete with no sequelae.1 Data con-
cerning toxicological effects of RDX to humans are
extremely limited. Seventeen cases of toxic re-
actions which occurred between 1939 and 1942 in
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14
Italian workers handling powdered RDX in the drying,
cooling, sealing and packing process of its manu-
facture have been described.2 Ten had generalized
convulsions of clonic-tonic type followed by postictal
coma; four had loss of consciousness without con-
vulsions; two had vertigo; and one had vomiting and
confusion. Similar cases in German workers handling
finely pulverized RDX powder have been described.3
The author experienced no fatal cases; however, he
alluded to German newspaper reports in the post
World War II period that paper bags used for wrap-
ping food after having been used for packaging RDX
caused four deaths. Oral ingestion of RDX by rats
or dogs resulted in hyperirritability, viciousness,
generalized convulsion of a clonic-tonic type and
death.1* Similar symptoms have been noted.5 In
acute toxicity studies of rats the LDs0 was found to
be approximately 200 mg/kg in non-fasting rats, and
50 to 100 mg/kg in fasting rats. In chronic toxicity
studies, the LD^ was approximately 50 mg/kg in-
gested daily, with a wide variation in the total
dose that was fatal. In cases of acute poisoning,
the vascular supply of the central nervous system
appeared affected through changes in the fibrous
material of the vessel wall; degeneration of the
nerve cells was also observed. The most affected
area was the spinal cord; less so the brain stem;
and least the cortex. In chronic exposures, not
only the central nervous system but also the liver,
lungs, and heart were involved. Principal changes
occurred again in the fibrous material blood ves-
sels, leading to impaired blood circulation and
metabolism. The fatty acid metabolism especially
was affected, and secondary degeneration occurred
throughout the organ systems. It was found that RDX
injected intraperitoneally caused convulsions and
death in rats in 9 to 121 minutes; subcutaneous and
intravenous injection of RDX also caused a rapid
onset of convulsions. Doses as low as 10 mg/kg
intraperitoneally and 18 mg/kg intravenously caused
death. Thus, relatively small quantities of RDX, if
absorbed, are capable of causing toxic symptoms and
death in laboratory animals.
1 A. S. Kaplan, 0. F. Berghout and A. Peozenik.
Human Intoxication from RDX. Areh. Environ. Health,
10.-ISS 6, 877-883, 1965
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15
2 M. Barsotti and G. Crotti. Epileptic Attacks as
Manifestations of Industrial Intoxication Caused by
Trimethylenetrinitroamine, Lavoro 40:107-112, 1949
^ V. Vogel. Hexogen Poisoning in Human Beings, in
German. Zbl Arbeitsmed 1:51-54, 1951
** W. F. Von Oettingen, et al. Toxicity and Potential
Dangers of Cyclotriethylenetrinitramine. J. of
Industrial Hygiene, 31:21-31, 1949
5 F. W. Sunderman, J. K. Clark and E. S. Bills.
Compilation of Informal Monthly Reports on Hazards
to Health of Individuals Working with RDX, May 1943-
June 1944, National Defense Research Committee of
the Office of Scientific Research and Development,
NORC Contract No. OEM sr-962, unclassified, 1944
STILBENE This compound, also known as bibenzal, or bibenzylidene
(CAS Registry Number 588590), is isosteric with
azobenzene. In view of the apparent importance of
molecular shape in compounds having carcenogenic and
tumor inhibitory activity, stilbene derivatives
should have such activity. In fact, stilbene was
first produced because it was suspected that it
would have an acaricidal activity.1 Because
stilbene is estrogenic it was thought that it might
prevent heart failure in middle-aged males without
producing secondary female sex characteristics. This
was found to be the case. Stilbene itself is
considered to be non-carcenogenic.2 In addition to
the intense estrogenic activity,3'4'5 stilbene
derivatives have biocidal properties such as anti-
fungal6 or cancerostatic.7
1 W. A. Sexton. Chemical Constitution and Bio-
logical Activity, pp 409-410, D. Van Nostrand Company,
1963
2 G. E. Mikhailovskii and Yup Kozlov. Inclusion of
Polycyclic Hydrocarbon Molecules into the Respiratory
Chain as one of the Basic Mechanisms of Chemical
Carcinogenesis, Biofizika 12(5):938-941, 1967
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16
^ R. L, Preston, J. E. Martin, J. E. Blakely, and
W. H. Pfonder. Structural Requirements for the
Growth Response of Certain Estrogens in Ruminants,
J. Anim. Sci., 24(2):338-340, 1964
** N. P. Buu-Eoi, G. Saint-Ruf, and G. Beauvillain.
Differences in Estrogenic Activity Between Trans-
Stilbene and Trans-Ar-Decadeuteriostilbene, C. R.
Acad. Sci.3 Ser. D., 268(8):1221-1222, 1969
5 T. S. Danowski, N. R. Limaye, R. E, Cohn, B. J.
Grimes, J. 7. Narduzzi, and C. Moses. Species
Differences in Lipid and Endocrine Gland Response to
a Stilbene Derivative, J. Pharm. Sci., 55(6):635-
636, 1966
6 L. Drobnica^ M. Zemanova, P. Eemec, K. Antos,
P. Kristian, and A. Martvon and Zavokska. Antifungal
Activity of Isothiocyanates and Related Compounds.
III. Derivatives of Biphenyl, Stilbene, Azobenzene,
and Several Poly condensed Aromatic Hydrocarbons, Appi.
Microbiol., 16(4):582-587, 1968
7 K. Eorakova, L. Drobnica, P. Nernnc, P. Kristian,
K. Antos, A. Martvon. Cytotoxic and Cancerostatic
Activity of Isothiocyanates and Related Compounds. III.
Effect of Stilbene, Azobenzene, and Polycondensed Aromatic
Hydrocarbon Isothiocyanate Derivatives on Eela Colis,
Neoplasma 16(3):231-237, 1969
STYRENE Styrene may be irritating to eyes and mucous membrane,
and in high concentrations it is narcotic.1 In
acute static bioassay the following fish had TLM96 of:
Pimephales pronelas, 51 ppm; Lempomis macrochirus,
22 ppm; Carassius auratus, 68 ppm; and Lebistes
reticulatus, 68 ppm.2
1 Merck Index, 1970
2 Q. H. Pickering and C. P. Henderson. Acute
Toxicity of Some Important Petrochemicals to Fish,
J. Water Pollution Control Federation, 38(9):1419-
1429, 1966
Additional information:
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17
V. P. Shatalov, A. P. Titov, L. I. Kovtunenko, E. I.
Akovenko, G. P. Filinov, V. Y. Aleshina, and L. A.
Zadvornaya. Use of Sodium Alkylsulfonates for
Obtaining Butadienestyrene and Butadiene-methyl
Styrene Rubbers. In Russian, Prom. Sin. Kauch.
Nauch.-Tekh. Sb. (DSMMYC)No. 1, 1971:5-7
H. G. Keppler, L. Zuern, E. Stahnecker, and V.
Gruber. Purification of Wastewater from the Poly-
merization of Styrene. In German, Ger. Offen.
(GWXXBX) 2057743 (C 02C), 24 Nov. 1970, 8 p
N. Mosescu and E. Dacin. Determination of Benzene,
Ethyl-benzene and Styrene in Waste Waters by Ultra-
violet Spectrophotometry, Luor. Conf. Nat. Chin.
Anal., 3rd (24 UNAT) 2,63-68, 1971
V. S. Mirzayanov and Y. F. Burgov. Gas-Chromat-
ographio Determination of Organic Impurities in
Waste Waters. In Russian, Zavcd. Lab. (ZVDLAU)
38(6):6-56, 1972
H. G. Keppler, L. Zuem, and E. Stahneoker. Purifi-
cation of Waste Waters from the Polymerization of
Styrene. In German, Ger. Offen. (GWXXBX) 2064575 (C
08F), 30 Dec. 1970, 9 p
E. E. Hughes. Styrene Plant Waste Heat Utilization
in a Water Desalination Process, U. S. (USXXAM)
3691020 (203-24: R. OUD), 20 Aug. 1971, 5 p
TNT This compound is also known as 2,4,6-Trinitrotoluene
or s-Trinitrotoluene. TNT has been found to chemically
induce many degenerative diseases through long
periods of moderate exposure. 2,4,6-Trinitrotoluene
has been found to cause hepatitis, cataracts, fatty
liver, jaundice, dyspancreatism, and increased
glycolysis.1 In a study by Manoilova and Zakharovi
a total of 360 persons occupationally exposed to
this toxic substance for at least 5 years were
examined. In 45.3% an eye lesion taking the form of
a singular specific cataract was discovered, which
may appear as the first and only clinical mani-
festation of poisoning. No severe internal changes
were demonstrable. Most frequently occurring were
astheno-vegetative syndrome, chronic gastritis with
subnormal acidity and mild forms of hepatitis.2 One
hundred parts per million of TNT were found to
produce a complete kill of the algae, Microcystis
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18
aeruginosa, in five days.3 The anaerobic digestion
of sludge from sewage containing 60 mg/1 of TNT was
practically unaffected by the TNT.4 TNT can be
decomposed in sewage aerobically but only at con-
centrations of a few nig/1. It was found to be
utilized by infusoria and flagellates as nitrogen or
carbon sources; concentrations of 0.5-1.0 mg/1 only
slightly retarded the self-purification of water.
The limit suggested for sewage treatment was 10
mg/1.5 A concentration of 2 mg/1 of TNT reduced the
5-day BOD of sewage at 18.3°C by 6%, 5 mg/1 by 15%
and 20 mg/1 by 35%.6 In laboratory experiments
using percolating filters impregnated with Nocardia,
100 mg/1 of TNT was not decomposed, but slow de-
composition occurred anaerobically with the micro-
flora of domestic sewage.7 TNT at concentrations of
5 to 50 mg/1 was found to be destroyed during the
anaerobic digestion of sewage sludges at 36°C.8
100 mg/1 of TNT was slightly oxidized by phenol-
adapted bacteria in Warburg respirometer experiments
at 30°C.9
1 J. W. Goodwin. Twenty Years Handling TNT in a
Shell Loading Plant. Am. Ind. Hyg. Assoo. J.,
33:42-44, 1972
P. Hassman and J. Juran. Cataract in Persons
Working with Trinitrotoluene, in German. Int. Arch.
Gewerbepath, 24:210-218, 1968
P. Hassman and A. V. Hassmanov. Liver Steatosis
in a Subject Working for Several Years with Trini-
trotoluol, in German. Sborn Ved Prac Lek Fak Kariov
Univ., 12:561-564, 1969
P. Hassman and A. V. Hassmanov. Contribution to
the Problem of Early Diagnosis of Trinitrotoluene
Poisoning, in Czech. Sborn Ved Prac Lek Fak Kariov
Univ., ll:Suppl, 339-52, 1968
I. K. Manoilova and A. I. Zakharova. Clinical
Picture in Chronic Trinitrotoluene (TNT) Poisoning.
Gig Tr Prof Zabol, 15:28-32, 1971
A. Kleiner. Change in the Ammonia, Phosphate and
Lactic Acid Levels in the Gastric Juice of Dogs
During Chronic Trinitrotoluene Poisoning. Farmakol.
Toksikol, 32:578-579, 1969
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19
2 J. K. Manoilova and A. I. Zakharova. Clinical
Picture in Chronic Trinitrotoluene (TNT) Poisoning.
Gig Tr Prof Zabol, 15:28-32, 1971
3 G. P. Fitzgerald, G. C. Gerloff, and F. Skoog.
Studies on Chemicals with Selective Toxicity to
Blue-Green Algae, Sewage and Industrial Wastes,
24:888-896, 1952
** R. Wilkinson. Treatment and Disposal of Sewage
and Waste Waters from Shell-filling Factories. J.
Proc. Inst. Sew. Purif., Pt. 1:145-150, 1945
5 T. I. Rogovskaya. The Effect of Trinitrotoluene
on the Micro-organisms and Biochemical Processes of
Self-Purification of Water. Mikrobiologlya, 20:265-
272, 1951, in Russian
6 T. A. Larionova. The Effect of Trinitrotoluene
on the Biochemical Consumption of Oxygen and the
Oxidation Ability of Water. Gig. Sanit. 8:20-22,
1951, in Russian
7 G. Sringmann. Zum Biologischen Abbau Mehrwertiger
Phenole und Witrophenole. Gesundheitsingenieur
76:239-240, 1955
8 V. Madera, V. Solin and V. Vucka. The Biochemical
Reduction of Trinitrotoluene. The Reduction of
2,4,6-Trinitrotoluene and Its Products. Sb. vys.
Sk. Chem.-technol. Praze, 3: Pt. 1, 129-147, 1959,
in Czech
9 C. W. Chambers, E. H. Tabak and P. W. Kabler.
Degradation of Aromatic Compounds by Phenol-adapted
Bacteria. J. Wat. Pollut. Control Fed. 35:1517-
1529, 1963
n-TETRACOSANE See n-TRICOSANE
n-TETRA- See n-TRICOSANE
TRIACONTANE
n-TRIACONTANE See n-TRICOSANE
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20
TRICHLOROANILINE
Difluoroaniline, 4-fluoroaniline, and 3-bromoaniline
caused methaemoglobin formation in various animal
species lowering the level of intact haemoglobin.
S. McLean, G. A. Starmer and J. Thomas. Methaemoglobin
Formation by Aromatic Amines. J. Pharm. Pharmac.,
21:441-450, 1969
TRICHLOROBENZENE
The toxicity of chlorobenzene, dichlorobenzene and
trichlorobenzene is on the same level; increasing
the number of chlorine atoms in a benzene molecule
does not affect the toxic action, but affects only
the degree of expressivity. In determining the
maximum permissible concentrations of these com-
pounds in bodies of water, chronic experiments were
conducted with white rats. Conditioned reflex
activity was depressed showing a cerebral cortical
effect; erythropoiesis was significatnly decreased,
with chlorobenzene producing eosinophilia and ortho-
dichlorobenzene, neutropenia. Ortho-dichloroben-
zene, more than chlorobenzene, led to a sharp rise
in urinary steroids.1 Results of an investigation
by Gurfein and Pavlova indicated that 0.03 mg/1 of
either di- or trichlorobenzene could be recommended
as the limit of allowable concentration in water
basins. Such conclusions were arrived at on the
basis of the organoleptic index.2 For chloroben-
zene, Pickering and Henderson reported a TLM2tt of
29 ppm for fathead, 24 pprn for bluegills, 73 ppm for
goldfish, and 45 ppm for guppies.3 Exposure of
fresh water micro life to 100 ppm of trichlorobenzene
results in a 98% kill; chronic feeding has caused
loss of hair in experimental animals.4
1 S. P. Varshavskara. The Comparative Sanitary and
Toxicological Characteristics of Chlorobenzene and
Dichlorobenzene (Ortho- and Para-Isomers) from the
Point of View of Sanitation of Water Reservoirs, in
Russian. Gigiena I Sanit., 33:15-22, 1968
2 L. N. Gurfein, and Z. K. Pavlova. Limits of
Allowable Concentrations of Chlorinated Benzenes in
Water Basins. USSR Literature on Water Supply and
Pollution Control, Z:58-65, 1962. U. S. Department
of Commerce
3 Q. E. Pickering and C. Henderson. Acute Toxicity
of Some Important Petrochemicals to Fish. J. Water
Pollution Control Federation, 38:1419-1429, 1966
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21
4 Technical Assistance Data System: 72T16929,
ENVIRONS, EPA
n-TRICOSANE The long chain paraffin hydrocarbons generally
should have little if any effect on water quality
as they are all produced naturally and metabolized.
Excessive concentrations would of course have a
deleterious effect on BOD. For example, tobacco
produces the following straight chain hydrocarbons:
heptacosane, octacosane, nonacosane, triacontane,
hentriacontane, dotriacontane, tritriacontane, tetra-
triacontane and pentatriacontane.T From the stand-
point of water purification the behavior of these
long-chain hydrocarbons will be very similar to
their fatty acids which has been studied by Grin.
His experiments established that 0.1 mg/1 of the
fatty acids (range C5-C20) was the minimal con-
centration which effected the BOD. Therefore, this
concentration was regarded as the threshold BOD
effect in water. Tests had also shown that the
mineralization rate of domestic sewage type of
organic matter in the presence of 3 to 4 mg/1 of fatty
acids was the same as in the control tests. Fatty
acids lowered the rate of water auto-purification
processes beginning with 5 mg/1. Ammonia accumulation
was of a slower rate in the presence of fatty acids
in the test samples than in the controls during the
first six days; thereafter it gradually exceeded the
control rates. Nitrification rate varied with the
concentration and with the fraction type of the
fatty acid. The second nitrification phase, formation
of nitrites, manifested a higher sensitivity to the
arresting effects of fatty acids; the arrest intensity
was directly proportional to the fatty acid concen-
tration.2
1 Kaneda. Biosynthesis of Long-Chain Hydrocarbons.
I. Incorporation of L-Valine, L-Threonine, L-
Isoleucine, and L-Leucine into Specific Branched-
Chain Hydrocarbons in Tobacco. J. Biochemistry,
6:2023-2052, 1967
P. E. Kolattukudy. Tests Whether a Head-to-head
Condensation Mechanism Occurs in the Biosynthesis of
n-Hentriacontane, the Paraffin of Spinach and Pea
Leaves. J. Plant Physiol., 42:1466-1470, 1968
L. Hankl and P. Kolattukudy. Metabolism of a
Plant Wax Paraffin m-Nonacosane, by a Soil Bacterium
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Micrococcus Cerificons.
463,, 1968
22
J. Gen. Microbiol., 51:457-
P. E. Kolattukudy and L. Harikin. Metabolism of a
Plant Wax Paraffin m~Nonacosane in the Rat. J.
Nutr., 90:167-174; 1946
2 N. V. Grin. Experimental Determination of
Maximal Allowable Concentrations of Medium and High
Molecular Fatty Acids ^5-^20- USSR Literature on
Water Supply and Pollution Control, 5:175-180, 1966,
US Department of Commerce
n-TRITRIACONTANE See n-TRICOSANE
XYLENE TLM values for various fish are: Pimephales promelas -
TLM96 of 21 ppm; Lepomis machrochirus - TLMg5 of 22
ppm; Carassius auratus - TLM96 of 24 ppm; Lebistes
reticulatus - TLM96 of 39 ppm. Daphnia magna in
static acute bioassay had LD50 of 1 ppt.2 p-Xylene
had a thermodynamic activity in the range of 0.001
to 0.1 and gave a threshold narcosis 50 toxicity to
barnacle larvae with active appendages but with no
forward movement in Elminius modestus larvae after
15 minutes.3 Based on the combined results of
chronic sanitary-toxicological and organoleptic
experiments Rubleva, in 1962, concluded that 0.08
mg/1 should be adopted as the limit of allowable
concentration for xylene in water basins.4 This
value was lowered to 0.05 by Cherkinskii in 1966 on
the basis of additional test results.5 More recently
(1968) Kashin, Kulinskaya, and Mikhailovskaya found
that the prolonged effect of small concentrations of
m-xylene resulted in inhibition of agglutinin formation
and functional activity of the adrenal cortex,
disorders of acetycholin mediation and protein-
forming function of the liver and loss of weight.
They concluded that xylene possesses high toxicity
and the permissible concentration should be further
decreased.6
1 Q. H. Pickering and C. Henderson. Acute Toxicity
of Some Important Petrochemicals to Fish. J. Water
Pollution Cont. Fed., 38:1419-1429, 1966
2 B. F. Dowden and E. J. Bennett. Toxicity of
Selected Chemicals to Certain Animals. J. Water
Pollution Cont. Fed., 37:1308-1316, 1965
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23
3 D. J. Crisp, A. 0. Christie and A. F. Ghobashy.
Narcotic and Toxic Action of Organic Compounds on
Barnacle Larvae. J. Compendium of Chemistry and
Physiology, 22:629-649, 1967
^ M. N. Rubleva. Limit of Allowable Concentration
of Xylol in Water Basins. USSE Literature on Water
Supply and Pollution Control, 3:46-52, 1962, US
Dept. of Commerce
5 S. N. Cherkinskii. Conditions for the Sanitary
Discharge of Sewage and Waste Water into Natural
Water Basins. USSR Literature on Water Supply and
Pollution Control, 6:131-144, 1966, US Dept. of
Commerce
6 L. M. Kashin, I. L. Kulinskaya and L. F. Mikhai-
lovskaya. Changes in the Animal Organism Under the
Effect of Small Concentrations of Xylol, in Russian,
Vrachebone Delo, 8:109-112, 1968
Additional Information:
M. Ghirardoni and C. Thiella. Simultaneous Quali-
tative and Quantitative Determination of Aromatic
Hydrocarbons and Phenols in Industrial Wastewaters.
In Italian, Boll. Lab. Chim. Prov. (Bolaau) 22(6):
1024-1030, 1971
B. B. Shugaev. Concentrations of Hydrocarbons in
Tissues as a Measure of Toxicity, Archives of En-
vironmental Health (Chicago) 18:878-882, 1969
C. H, Hine and H. H. Zuiema. The Toxicological
Properties of Hydrocarbon Solvents, Industrial
Medicine and Surgery 39:215-220, 1970
S. W. Nielsen. Environmental Pollutants Pathogenic
to Animals, J. Am. Veterinarian Medical Assc.
159:1103-1107, 1971
G. Baurhenne. Removal of Xylene and Formaldehyde
from Waste Gas. In German, Ger. Offen. (GWXXBX)
2060802 (B.01D), 10 Dec. 1970, 7 p
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