Document K529kv58DYxp88BQYdxwjnbX

MEMBER AGENCIES Council on Envfmnmantat Quality I'--Narimant of Commorco onmcntsl Protaction Agency . onal Concor Inatltut# National Institute of Environmental Hooftti Scloncoo National Institute for Occupational Safety and Health National Science Foundation Occupational Safety and Health Administration TOXIC SUBSTANCES CONTROL ACT INTERAGENCY TESTING COMMITTEE 401 M Street, SW Washington, DC 20460 UAiSON AGENCIES Consumer Product Safety Commission Department of Agriculture Deportment of Dofanso Department of tho Interior Pood and Drug Administration National Toxicology Piugram RECElVtD SEP 2 881 Mr. James Hall Conoco Chemicals Box 2197 Houston, Texas 77001 Dear Mr - Hall: Per our telephone conversation of September 1, 1981 I am pleased to enclose copies of the following Hazard Information Reviews prepared for the ITC by its technical support contractor: IR-235: Mono(Ciq-16)Alkylbenzenes IR-236: Mono(10-I6)Alkylbenzenesulfonic Acids and their Sodium Salts I wish to thank you for your cooperation in providing input of technical data to IR-235. Enclosures (2) Executive Secretary ITC SAL 000020031 HAZARD INFORMATION REVIEW WORKING DRAFT- Mono(Cio-i6)Alkylbenzenes IR-235 July 15,1981 Prepared under EPA Contract No, 68-01-5789 for: TSCA Interagency Testing Committee Prepared by: Enviro Control The Dynamac Building 11140 Rockville Pike Rockville, MD 20852 SAL 00020032 HAZARD INFORMATION REVIEW WORKING DRAFT Mono(Cio-i6)Alkylbenzenes IR-235 July 15,1981 Prepared under EPA Contract No. 68-01-5789 for: TSCA Interagency Testing Committee Prepared by: Enviro Control The Dynamac Building 11140 Rockville Pike Rockville, MD 20852 SAL 000020033 N___ 0 T I C E THE INFORMATION CONTAINED IN THIS REVIEW WAS COMPILED FROM COMPUTERIZED DATA BASES, TECHNICAL LIBRARY RESOURCES, AND NONCONFIDENTIAL INFORMATION IN GOVERNMENT FILES OR PROVIDED BY THE PRIVATE SECTOR. THE PREPARATION OF THIS WORKING DRAFT IS JUST ONE STEP IN THE STUDY OF POSSIBLE HEALTH AND ENVIRONMENTAL HAZARDS OF THE CHEMICAL OR CATEGORY OF CHEMICALS DESCR I BED- HERE IN . THE EXISTENCE OF THIS REVIEW DOES NOT NECESSARILY IMPLY THAT THE ITC WILL RECOMMEND THE CHEMICAL TO THE EPA FOR TESTING RULES PROPOSAL . SAL 000020034 Mono(Cio-l6)Alky1benzenes CONTENTS Pa^e PREFACE........................ "......................................................................... 11 AN OVERVIEW .......................................................................................... Iv I. CHEMICAL AND PHYSICAL PROPERTIES .................................... 1 A. Identification........... ............ *................................................ 1 B. Formulas and Molecular Weights .......................................... 1 C. Physical Properties .................................................................. 1 D. Chemical Properties ....................................... .......................... 1 E. Exposure Estimates ............................................................. .. 4 F. Scores from 1980 ITC ScoringExercise............................. 9 II. BIOCHEMICAL INFORMATION .......................................................... 11 A. Metabolism...................... 8. Effects on Enzymes and Other Biochemical Aspects................. 11 12 III. TOXICOLOGICAL INFORMATION ...................................................... 12 A. Carcinogenicity........................................................................... 12 B. Mutagenicity................................................................................. 13 C. Teratogenicity, Embryotoxiclty, and Fetotoxlclty .. 13 D. Special Studies............................ ............................................ 13 E. Toxicity..................................... 13 IV. OBSERVATIONS IN HUMANS ............................................................ 16 V. ENVIRONMENTAL INFORMATION..................................................... 15 A. Environmental Release and Concentrations .................... 16 B. Environmental Fate *............... 17 C. Ecological Effects .................................................................... 20 VI. DATA BASES SEARCHED AND AUTHORS........................................ 22 A. Data Bases Searched.................................................................. 22 B. Authors ............................ 23 VII. TOXICOLOGICAL AND ECOLOGICALSUMMARY ................................. 24 ENCLOSURES .............................................................................................. 27 CITED REFERENCES ................................................................................. 31 SAL 000020035 MonpICj q. ] g)AI kyl benzenes PREFACE This Information Review covers the commercial compounds known as "detergent al plates." These compounds are produced and used as mixtures* The TSCA Inventory lists some of the components of the mixtures as well as the mixtures themselves* Components of Detergent Alkalate Mixtures Listed In TSCA Inventory Empirical Formula CAS No. Name c1626 a,b 104-72-3 Oecylbenzene C17H28 a'b 6742-54-7 Undecylbenzene C18H30 a*b 123-01-3 Dodecylbenzene C19H32 .b 123-02-4 Trldecylbenzene C20H34 a-b 1459-10-5 Tetradecylbenzene c2lH36 a c2238 4 C23H40 c C24H42 c C25H44 c 2131-18-2 1459-09-2 14752-75-1 4445-07-2 29136-19-4 Pe ntadecy1benzene He xadecylbenzene Heptadecylbenzene Octadecyl benzene Novadecylbenzene Normal 'detergent alkylate* range. ^High-production chemicals selected for study by 1TC In Third 1TC Scoring Exercise, delated co^ounds. Detergent Alkalate Mixtures Listed In TSCA Inventory Empirical Formulas CAS No* Name Ci8H30-C24K42 68890-99-3 Hono-Ci2-Ci8-alky1 benzenes C16H26-C19H32 6 7774-74-7 Cl$H26-C22-H38 68648-87-3 11 SAL 000020036 Mono{ C*| o-16 )A1 Kyi benzenes The production of these compounds and their relationships to the linear alKylbenzenesulfonate detergents (LAS), which are the subject of IR-236, are sunmarlzed In the following scheme. Ethylene Dodecene from kerosene Polymerlzatlon v Linear alkyl chloride or olefin (mixture) Alkylation of benzene Linear alkvlbenzene (mixture) Reviewed In this IR Sulfonatlon \ Linear alkyl benzene sulfonic acid (mixture) Meutrallzatlon \' Linear alkyl benzene sulfonate salt (mixture) Detergent formulation Revised In IR-236 Before 1965, tetrapropylene (branched chain) was used to alkylate benzene. The detergents resulting from this process were not bio degradable and caused extensive foaming of wastewaters. ill SAL 0020037 Mo no(Cio-l6)Alkylbenzenes I. CHEMICAL AND PHYSICAL PROPERTIES A. IDENTIFICATION Refer to Table 1. B. FORMULAS AMD HXECULAR HEIGHTS Refer to Table 1. C. PHYSICAL PROPERTIES Comment Physical properties for linear alkylbenzenes In this group are relatively scarce because the compounds are produced and used as mixtures. They are liquids or waxy solids with low solubility in water and boiling points above 2550 c. The few data found appear to be for mixtures of Isomers and compounds. Decylbenzene Dodecylbenzene Boiling Point: 255-280OC (TDB) 290-41OOC (TDB) Specific Gravity: 0.9 (TDB) 0.9 (TDB) Log P octanol/water: est. 7 (Leo et al., 1971) est. 8 (Leo et al,, 1971) Impurl ties: See Production Section I.E.l D. CHEMICAL PROPERTIES Comment: Linear (C-|o-l6)alkylbenzene should exhibit most of the reactions of linear alkanes and alkyl-substituted aromatics (e.g., toluene). Electrophilic substitution on the aromatic ring (e.g., nitra tion, sulfonatlon, and alkylation) is an Important industrial reaction. The alkyl substituent on the benzene ring should activate the ring toward electrophyllc substitution relative to benzene (Roberts and Caserlo, 1964). However, the large alkyl group may tend to Inhibit substitution due to sterlc effects. -1- SAL 000020039 )Alkylbenzenes SAL 0 0 0 0 2 0 0 4 0 Table 1. Identification, formulas, and molecular weights of mono(C10_16}alkylbenzenes. Kane Decylbenzene Undecylbenzene Dodecylbenzene Trldecylbenzene Tetradecylbenzene Pentadecylbenzene Nexadecylbenzene CAS Ho. 104-72-3 6742-54-7 123-01-3 123-02-4 1459-10-5 2131-18-2 NIOSHNo. - - - -- - - - -- -------- -------- - - - None found ------------- -- Synonyms ............................................................ Detergent alkylates, linear alkylbenzenes, LAB --------- Structural formula ch3(ch2),,ch(ch2)bch3 6 where n + m 7 to 11 {n * 0 to 11, m > 0 to 11) See Table 2 for Isomer distribution. rio Empirical formula ' C16H26 Molecular weight 218.39 C17H28 232 C18H30 246.48 C19H32 260 C20H34 274 C21H36 288 1459-09-2 C22H38 302 o> Mono(Cio-16)AlKyibenzenes According to Papp et al. (1979), sulfonatlon of dodecylbenzene at 60OC yielded 5% para Isomer, whereas sulfonatlon at 12QC yielded 15% para Isomer. The remaining product In each case was the ortho 1somer. Comment: The source of these data Is Chemical Abstracts; the ratio of ortho to para is different from the expected ratio as Is shown below for nitration. According to Brandt and Verbesselt (1972), nitration of alkylbenzenes results In a pre dominance of para Isomers even though there are two positions to be substituted. O nitration CH3 (Toluene) C2H5 (Ethylbenzene) C8Hi7 (Acetylbenzene) c10H2l (Oecylbenzene) c12H25 (Dodecylbenzene) C16H33 (Hexadodecylbenzene) ortho Isomer para Isomer Percent yield from nitrogen 63% 37% 49% 51% 46% 54% 47% 53% 46% 54% 43% 52% -3SAL 000020041 Mono(C]o-16)A1 ky 1 benzenes E. EXPOSURE ESTIMATES The detergent alkylates are available commercially as complex mixtures of Isomers and homologs In proportions dependent on starting materials and reaction conditions. The alkyl chains of conmenclally available alkylbenzene mixtures generally range from 10 to 14 carbons In length. The phenyl groups are attached at various Internal carbon positions on the alkyl chain as In dicated In Table 2 (A.O. Little, 1977). The commercial alkyl benzene product of most Importance is referred to as "dodecylbenzene" (CPS, 1979), not to be confused with the compound dodecylbenzene (CAS No. 123-01-3). 1. Production "Dodecylbenzene- Is produced by alkylation of benzene with dodecene or dodecyl chloride In the presence of aluminum chloride, liquid hydrochloric acid, or sulfuric acid. Until 1965, dodecene was produced solely by polymerizing propylene with a phosphoric acid catalyst, which resulted in a branched chain dodecene. A branched chain dodecene Is undesirable for environmental reasons, and since 1965 a linear dodecene has been used Instead (Klrk-Othmer, 1978). The most Important source of the linear compound is dodecane, which Is removed from kerosene by molecular sieves. Linear dodecene may also be made by polymer!zatlon of ethylene or by the thermal cracking of paraffin wax to alpha-olefins (CPS, 1979). The alkylation of benzene produces a number of side re actions resulting In products as shown in Figure 1. The linear monoalkylbenzene 1$ purified by passing the reaction mixture through a series of three fractionating columns. The dlphenylalkanes and dialkylbenzenes boll at temper atures sufficiently above those for the linear monoalkylbenzenes that they are readily removed. However, some of the other dialkyl benzene materials cannot be separated from the primary product with ease, and they remain In the connerclal product. Dlalkyltetralin, dial ky lindane, and dialkylnaphthalene moieties may represent as much as 9-10% of the final product (A.O. Little, 1977). Table 3 lists the 1977 production volumes of the alkylbenzenes as reported by the manufacturers to the TSCA Inventory (1981). Although the detergent alkylates are produced and sold as complex mixtures, several companies reported the production of the alkylates as Individual com pounds. Nonetheless, the aggregate production figures In the TSCA Inventory (1981) for the pure compound and the mixtures compares well with the production figures for the comnerclal product reported by CPS (1979) (Figure 2). -4- SAL 000020042 Mono(C10_i6)A1kylbenzenes Table 2. Composition of representative commercial LAS products.4 Carbon chain length ____________________________Percent of Total Supplier "A Supplier B Product product Product Product 12 12 Supplier C Product " Product 12 Phenyl position 2-phenyl alkane 3-phenylalkane 4-phenyl alkane 5-phenylalkane 6-pher\yla1kane 7-phenylalkane Tetralins and byproducts 32 30 25 25 33 29 NA NA NA NA 20 17 NA NA NA NA 18 16 NA NA NA NA 18 17 NA NA NA NA 11 15 NA NA NA NA 6 6 7 NA NA 6-10 6-10 Manufacturers' specifications. Note that the data are for the finished linear alkylbenzenesulfonates (LAS), which reflect the composition of the starting materials (l.e., alkyl benzene). Maximum percentage. Adapted from A.D. Little (1977). -5 SAL 000020043 Mono(C1Q_lg)A1kylbenzenes cYcV/VH(CH*,CHi Q CVCVyCVN(CV,CKJ OfttkjrlMflitn* (fw-i CO <CV,S CHjWKjJCHrCn^eHj 06 0<phanj>U1kaM CX7(CV^ DUlkyllAtfiiw Ot> (Ch,)xi OlilkylntplithiltM Figure 1. Products resulting from side reactions in the manufacture of linear a1kylbenzenes. From A.D. Little (1977). Figure 2. Production of commercial "dodecylbenzene" from 1960 to 1979 (CPS, 1979). -6- SAL 000020044 MonofCi q-]6 )A1 Kylbenzenes As Is indicated In Figure 3, the production of "dodecylbenzene" has been static or slightly declining over the past 10 years. This trend Is expected to continue (CPS, 1979). Table 3. Production of the alkylbenzenes, 1977. Compound Production In millions of pounds Decylbenzene Undecylbenzene Dodecylbenzene Tri decylbenzene Tetradecylbenzene Pentadecylbenzene Hexadecylbenzene Heptadecylbenzene Octadecylbenzene Nonadecylbenzene Mono- C-|2-Cjg-Alkylbenzenes C10"cl3"A1Kyibenzenes C10"cl6'A1Kyibenzenes 11 to 60 61 to 160 61 to 160 12 to 70 10 to 50 1 to 10 0 to 0.001 0 to 0.001 0 to 0.001 0 to 0.001 100 to 1CI to> 50 100 to 500 ooin Adapted from TSCA Inventory (1901). Figure 3. Flow diagram for "dodecylbenzene- manufacture using propylene tetramer. Substitution of dodecene for propylene tetramer should not alter the process (RiegeV s, 1974). -7- SAL 000020045 Mono(Ci o-l6)A1kylbenzenes 2. Use (CPS, 1979) "Dodecylbenzene" is used almost exclusively to produce dodecylbenzenesulfonlc acid and sulfonate salts, which are widely used as anionic surfactants In heavy-duty home laundry detergents and Industrial cleaners. The small amount of branched chain alkylbenzene produced Is used in the manufacture of the sulfonate used In the United States as industrial detergents or In glass slurry processes, but not In household detergents or in any applications In which It could enter rivers or streams. Small amounts of "dodecylbenzene" are used in the manufacture of dodecyl- nitrobenzene, dodecyl aniline, and dodecyl benzyl chloride. The 1973 estimate of the end use pattern Is as follows: Derivatlve Percent Detergent alkylate Sodium salt Acid Other salts 50 28 15 Miscellaneous and Exports 7 3. Occupational Exposure NOHS (1981) estimates that 13,961 workers are exposed to coranercial "dodecylbenzene." Wltco (1981) reported that "dodecylbenzene" 1$ manufactured In a closed continuous system. In addition, the company reported that the per sonnel at Wltco have not shown any adverse effects from "dodecylbenzene," and the company has been manufacturing the compound at an annual rate of 45 million pounds since 1966 (Wltco, 1981). Coirwent: The most likely route of exposure would be during the sulfonatlon process. Many manufacturers (greater than 25) purchase "dodecylbenzene" and sulfonate the compounds In preparation of the end product detergent. 4. Release Rate Comment: Although Wltco (1981) reports that alkylation hydrocarbons are manufactured In a closed continuous process, there mey be pathways of release. The crude product of the reaction of benzene and dodecene Is distilled three times: first through a benzene fractionator, then through an Intermediate fractionator, and finally through a "dodecylbenzene" fractionator (see Figure 3). Two -8 SAL 000020046 MonofC^o-i6)A1kyl benzenes byproducts of "dodecylbenzene" are collected during this process: a light alkyl aryl hydrocarbon cut and a heavy alkyl aryl hydrocarbon cut. These byproducts may be used In either fuel or asphalt or may be disposed of. One manufacturer reported to the TSCA Inventory (1981) that a Ci0-12 alkyl benzene distillation residue was manufactured In 1977 at levels between 1 million and 10 million pounds. 5. Manufacturers CPS (1979) reports the following manufacturers of the commercial product "dodecylbenzene": Conoco Baltimore, Maryland Monsanto Alvin, Texas Union Carbide Institute, West Virginia Witco Carson, California The manufacturers of the detergent alkalates reported In the TSCA Inventory are listed In Table 4. F. SCORES FROM 1980 ITC SCORING EXERCISE 1. Occupational and Consumer Exposure The exposure scores for the mono(Cio-l6)alkYlbenzenes (normalized from 0.0 to 1.0) are as follows: Decyl Undecyl Oodecyl Trl decyl Tetradecyl Occupational -Exposure Index 0.63 ---- ---- Environ- mental/ Consumer Exposure Index 0.38 0.42 0.39 0.38 -9SAL 000020047 Mono(0*10-16 )A1 Kyi benzenes Table 4. The manufacturers of the alkylbenzenes, as reported In the TSCA Inventory (1981). Conoco, Baltimore, MD >> >U<u o ai -o 0) c o Q =S a p-- >. u >(J> >i > o > > >> Q) 0) o T3 *o <j a> a o o U93 CO a -o mu ns 4-> *o ra -4(-O> T> TS fO < 4- e X & 4-* c o s_ 0) h- 0) Q. aj z 0) Z U o zo tH CJ **** a o o o <_> c o z oo o eg <_> o c o z Chevron, Richmond, CA Wltco, Carson, CA *! Union Carbide, Institute, WY Humphrey Chemical, North Haven, CT * l* Monsanto, Alvin, TX Gulf Oil, Houston, TX Stauffer, Akron, OH ICl America, Wllml ngton, DE 'Manufacturer. -10- SAL 000020048 Mono(Cio-16)A1ky1benzenes 2. Health and Environmental Effects Health and environmental effects were scored on a scale from 0 to 3 (minus assigned If score Is based solely on judgment In the absence of experimental data). Individual factor scores for the mono(C10_16)alkylbenzenes: Decyl Undecyl Dodecyl Trl decyl Tetradecyl Mutagenicity -1.0 -1.0 -0.8 -1.0 -1.0 Carcinogenicity -1.1 -1.1 -1.3 -1.1 -1.1 Teratogenicity -1.3 -1.3 -1.7 -1.3 -1.3 Reproductive effects -1.3 -1.3 -1.3 -1.3 -1.3 Acute toxicity -1.0 effects -1.0 0.3 -1.0 -1.0 Other toxic effects -1.5 -1.5 -1.5 -1 5 -1.5 Bloaccumulatlon 2.0 2.0 2.0 2.0 2.0 Ecologlcal -2.0 -2.0 -2.0 -2.0 -2.0 II. BIOCHEMICAL INFORMATION A. rCTABOLISM "Dodecylbenzene" (of unspecified Isomeric composition) adminis tered to rats (5 ml/kg, subcutaneously) did not Increase the urinary output of ethereal sulfate (Gerarde, 1960). This obser vation Indicated to the author that the benzene ring Is not hydroxylated In the metabolism of dodecylbenzene. However, In creased output of ethereal sulfate has been observed by Gerarde and Ahlstrom (1966) In the metabolism of the lower molecular weight linear alkylbenzenes (C]-C$). This reaction occurs as an alternative pathway as the dose is Increased. The main pathway 1$ side*chain oxidation. Comment: By analogy with the lower alkyl benzenes, n-butylbenzene (El Masry etal., 1955), and fc-pentyl- and n-hexylbenzene (Thlerfelder and Klenk, 1924), some degree of oxidation of the alkyl side chain of the detergent alkylates may -11- SAL 000020049 MonofCio-16)Alky1benzenes be expected. The scheme proposed by El Masry et al. (1956) for the oxidation of n-butylbenzene In the rabbit Is shown In Figure 4. Three possible pathways are shown fn this figure. The first pathway (a) Involves oxidation of the chain at the penultimate carbon, (to-1 )-ox1dat1on, with production of an alcohol, which Is excreted as a glucuronlde conjugate. The second pathway (b)"Involves oxidation at the terminal carbon, w-oxldatlon, to produce a carboxylic acid group. The third pathway (c) Involves oxidation at the carbon adjacent to the benzene ring (a-oxldation). The corresponding alcohol may then undergo conjugation to form a glucuronlde. Notice in Figure 4 that both (w-l )-ox1dat1on (pathway a) and co-oxidation (pathway b) may result In eventual shortening of the carbon chain. In the case of n-butylbenzene, the degradation product shown In Figure 4 is phenaceturlc acid, a conjugation product of phenyl acetic acid and glycine. Thlerfelder and Klenk (1924) also observed phenaceturlc acid In the urine of rabbits dosed with n-hexylbenzene. , PhCH-CH-CHjCH, v / V * () :o>) (c)-- PhCH-CH,CM(OH)CH, PHCH-CH.CH-COOH PhCH(OH)CH,CH,CH, l^ i i PhCH2CH2CH(OS)CH3 PhCHjCO-glycin* PhCH(06)CH2CH2CH3 Figure 4. Oxidation of n-butylbenzene. The broken arrow Indicates that there was no direct evidence for this pathway. (Ph * phenyl group, G * glucuronic acid residue). Adapted from El Masry et al. (1956). S. EFFECTS ON ENZYMES AND OTHER BIOCHEMICAL ASPECTS No information available III. TOXICOLOGICAL INFORMAT ION A. CARCINOGENICITY Dodecylbenzene (unspecified composition) Is cocarclnogenlc In nonhunan primates. No Information Is available on other monoalkyl benzenes. -12- 0020050 SM- 00 Mono(Cio-16)A1kylbenzenes Skin Carcinogenesis In Honhunan Primates Chemically Induced cutaneous carcinogenesis In nonhuman primates was studied by Im (1968), Adachl et al. (1969), and Palotay et al. (1976). 7,12-Dlmethylbenzanthracene (DMBA) combined with UV light and/or dodecylbenzene (DOB) was oncogenic when applied to the skin. Table 5~sunuiar1zes the results of cocarcinogenesis studies with dodecylbenzene in nonhuman primates and other mammals. No evidence was found to Indicate that the compound Itself Is carcinogenic. B. MUTAGENICITY Dodecylbenzene Is not mutagenic per se In cultured cells. However, It enhances the mutagenic effects of methylazoxymethanol. No Information Is available on other monoalkyl benzenes. Mutagenic Effects on Cultured Cells The potential of dodecylbenzene (unspecified composition) to enhance mutagenesis Induced by the carcinogen methylazoxymethanol at the ouabaln-reslstance locus was examined by Lankas et al. (1978*b). Dodecylbenzene at a concentration of 0.7 mM enhanced the frequency of methylazoxymethanol-lnduced mutations In the cultured cells. The compound did not show mutagenic activity per se nor did It affect the cell survival rate. C. TERATOGENICITY, EMBRYOTOXICITY, AND FETOTOXICITY No Information available D. SPECIAL STUDIES No Information available E. TOXICITY The toxicity of a single dose of 2.5 ml of a mixture of "dodecylbenzene" In olive oil (1:1 v/v) to fasted rats weighing approximately 225 g was tested by Gerarde (1959). No deaths *An asterisk attached to a reference denotes that a Toxicological and Ecological Summary of the study Is given in Section VII. -13- SAL 000020051 Mono(CjQ_jg)Alky1benzenes SAL Table 5. Cocarcinogenesis by "dodecylbenzene" (unspecified) In nonhuman primates and other mammals. Species Rout* Mo. of anlaals test group (control) Dose Effects Reference Mouse (C3H/He) ttouse (Svlss) ska Mouse (S78L) Rabbit (Mew Zealand albino) scu skn 10-15* (20) 10-60 (50 F) 30 W (~) 3-5* (-) 0.05. 0.10. 0.205 benzo(a) pyrene In 01 to 1001 000. 2 x wk. Single application of a 11 sol. Of 7.12-0MBA followed by repeated applications of pilot plant saaplo of alkylbanzeno or cwarclal samples of alkylbertzenes. Single Injection of a 1001 sol. of cnaaerclal saapla of alkylbanzene. Twice weekly application of a 1001 sol. of two coamerclal saaples of alkylbenzene. Effects of 0.05 and 0.201 benzo(a)pyrena were Indistinguishable when dodecylbenzene was used as a solvent (Enclosure 1). No carcinogenic activity seen In comnerclal saaples. However, promoting activity was shown by most of the saaples (Enclosure 2). No carcinogenic activity noted (Enclosure 3). Binghaa and Fall (1969) Safflottl at al (1962) Rhesus aonkey (Nacaca aulatte) m 3 H. 3 F (-) 1.01 7,12-OHBA (total dose 20.20 g) 1001 DOB 3 x wk for 6.5 yr + UV light for S atn. 3 x wk for 6.5 ao. Ton years after the treatment, deraal melanosis (1), papillomas (6), basal cell eplthelloaa (3). and mesoderaal sarcomas (2) developed. However, use of control animals was not stated. Pilot*/ et al. (1976) % 6* Two parts of the experl aan- Small papillomas on the skin at 2.5 ao and la (1968) (6 m tal area ware painted with keratoacanthoaas at 8 ap. Mirfced Quanti 0.8 ml of 11 solution of 7, tative changes In G6P0H5 and 6PH 12-0M9A In acetone 1 al of activities were found between treated (tu- of 1001 008. Prior to the aor and hyperplastic) and normal tissues. treatment one of the too experimental areas was exposed to IN light (2 x 10* ergs/cm2). One of the two control areas was treated with 0.S ml of DOB and acetone after IN Irra diation. Other control area was treated only with acetone after exposure to UV light. Anlaals wera painted 3 x 3k for S ao and 2 x wk for the next 7 ao. O O Sex not stated. o bG1ucose-6-phoaphate dehy<b*ogenase. 1S> C6-Pt)osphogluconate dehytoogenase. n o (continued) Table 5 Cocarcinogenesis by "dodecylbenzene (unspecified) in nonhuman primates and other mammals (continued). Mono(CjQ-j 6 )A1kylbenzenes SAL 000020053 Species Route No. of animals test group (control) Dose Effects Reference Galagos (Galaoo erassl- caudauis) sfcn 4 H. 4 F (4 K, 4 F) 2.5% 7,12-MBA (total dose 2.22 gk 100% DOB 3 x wk for 9 wk. then 100% 001 2 x wk for 4 yr. Control site (lower third) was treated with acetone * 000. 3 papulous, 2 basal cell epitheliomas, and 4 cases of basosquaaous coll epi dermal tumors wore found In 7 of 8 animals 6 yr after treatment. Palotay et al. (1976) II 4 H. 4 F 0.2 el of 2.5% 7,12-OHBA In After 4-5 wk, animals developed pseudo- Mch1 *t lie (196$) (4 M. 4 F) acetone 0.5 ml of D06 3 x epltheliamatous hyperplasia. G6PCH and wk. Control area was 6PG0H activity was higher In hyperplastic treated wl th acetone and than In normal epidermis. DM 3 x wk. Pottos (Perodlctlcus potto) ) N, 4 F cn i 2.5% 7,12-OMBA (total dose 0.135 G) + 100% DOB 3 x wk for 9 wk. Control site (lower third) was treated with acetone * DOR. 6 of the 7 animals died by 9 wk. Sur vivor showed no cutaneous lesions. Palotay et al. (1976) Sex not stated. hGlucose-6-pfcosphata dehydrogenase. c6-ftiosphogluconate dtfgrtfojHiM. /1ono(C-| Q_i6 )A1 1 benzenes occurred In the 10 rats dosed, Gerarde (I960), citing his 1959 study* Indicated that the acute oral toxicity of "dodecylbenzene" (unspecified composition) is greater than 5 ml/kg for the male rat. The direct aspiration of "dodecylbenzene" Into the lungs of tracheoctomlzed rats caused chemical pneumonitis, pulmonary hemor rhage, and death (Gerarde, 1960). Based on analogy with similar hydrocarbons, Gerarde (1960) suggests that prolonged exposure to "dodecylbenzene" vapor or mist at relatively high atmospheric concentrations would cause local Irritation of the mucous membranes of the nose, throat, and eyes. Similarly, prolonged or repeated contact of a detergent alkylate (i.e., "dodecylbenzene") with the skin may cause dermatitis due to drying and removal of the natural fats from the cutaneous tissues (Gerarde, 1960). IV. OBSERVATIONS IN HUMANS Witco (1981), Indicated that Dodane-S (composed of alkylbenzenes, CiQ-14) has been handled and produced since 1966 at an annual rate of 45 million pounds In a closed system without adverse effects on the personnel Involved. Witco Indicated that some people may have an allergic response to Dodane-S and Trldane-S (alkylbenzenes, Cn^is). V. ENVIRONMENTAL INFORMATION A. ENVIRONMENTAL RELEASE AND CONCENTRATIONS 1. Environmental Entry Cjo-15 linear alkylbenzenes are prepared in continuous closed processes (Witco, 1981). The compounds are used as Intermediates In the formation of linear alkylbenzenesulfonates. The alkylbenzenes are not used In any consumer products (Conoco, 1981) and potential exposure Is limited to the plants where they are manufactured and processed. 2. Environmental Concentrations Somaln et al. (1980) reported results of monitoring Indus trial discharges along the Illinois River. Ciq-Cis alkylbenzenes were observed at one source only, which was described as a manufacturing site for surfactants, deter gents, plastic moldings." In this sample, they found traces of "dodecylbenzene" and pentadecylbenzene. It Is noteworthy that these compounds were not observed In effluents from petrochemical plants and refineries. -16- SAL 000020054 Mono(Cjo-l6)A1ky1 benzenes B. ENVIRONMENTAL FATE The following comments give our projection of the environmental fate of linear alkylbenzenes based on certain experimental results and our judgment of how these results relate to environ mental processes. 1. Partitioning Among Environmental Compartments The methods of production and use of linear alkylbenzenes suggest that they are mainly released Into water effluents or "solid*1 waste. Their low volatility limits vaporization into the air. Their octanol/water partition coefficients are estimated to be very high (e.g., log P * 7-10, Leo et al., 1971), which Implies low solubility in water and a strong tendency to sorb to humic materials In soil and sediments. 2. Aquatic Chemistry Because of the strong tendency of these substances to sorb to sediments, photolysis and related reactions, which often destroy organic compounds in water, may be Inhibited (Oliver et al., 1979). 3. Atmospheric Chemistry Because of their low volatility, C]o-Ci6 alkylbenzenes are most likely to enter the atmosphere in the form of aero sols. Photolysis or hydroxyl radical oxidation of these materials as aerosols is expected to be rather slow. However, the alkylbenzenes as a class are regarded as readily degradable by hydroxyl radical oxidation (Darnell et al., 1976). 4. Biodegradation Two types of compounds must be considered for biodegra dation: compounds with the phenyl ring attached to the end of the linear alkyl chain, and compounds with the phenyl ring attached to a secondary carbon In the linear alkyl chain (e.g., usually adjacent to the end carbon). a. Linear alkylbenzenes with the phenyl group attached to an end carbon Sariaslanl et al. (1974) described results of the degra dation of linear 1-alkylbenzenes. When Nocardla salmonlcolor was grown on (linear) 1-dodecylbenzene as tne sole carbon source, there were two periods of growth. Each period was preceded by a lag phase during which enzyme Induction occurred. -17- SAL 000020055 Mono(Cj 0-16)A1Kyi benzenes The Initial metabolism of "dodecylbenzene" Involved oxidation of both the aromatic ring and the side chain. The metabolites that accumulated In the growth medium during this phase Included 4-phenyl butyrate, 4-phenylbut-3-enoate, 4-phenylbut-2-enoate, 3-phenyl propionate, clnnamate, and phenyl acetate. These compounds were con sumed as the first growth phase came to an end and rlng-hydroxylated compounds were produced. Rlnghydroxylated metabolites Included 4-(2-hydroxyphenyl) but-3-enoate and 4-(2-hydroxyphenyl) butyrate. The second growth phase Is accomplished by cleavage of the aromatic ring and oxidation to acetoacetlc acid and fumaric acid. The most important features of the scheme observed by Sarlaslani et al. (1974) are shown in Figure 5. b. Linear alkylbenzenes with the phenyl group attached to a secondary carbon Detergent alkylates are mixtures of Isomers In which the phenyl group Is almost always substituted on a secondary carbon of the alkyl chain (l.e., almost never on the terminal carbons). Degradation of these struc tures by the u>-ox1dation pathway shown In Figure 5 would yield structures of the type: CH3(CH2)xCH(CH2)yC02H Leldner et al. (1980) reported on the biodegradation of some phenylalkylcarboxyllc acids. Some structures seem to be more resistant to degradation than others. For example, within 16 days In mixed culture induced with readily degradable phenylalkylcarboxyllc acids, the two compounds CH3CHCH2COP2H and CH3CHCH2CH2CO2H -18- SAL 000020056 Mono(Cj0_jg)Alkylbenzenes (CH,)nCH, (CHt),,CH, n * even n odd I l - and 6- oxidation I 1 CH=CH COOH a- oxidation I (u- and 8- oxidation i steps (cHa)3COOH i elimination ch=chch2cooh Cinnamic acid i a- oxidation CH,COOH Phenylacetic acid 4-Phenylbut-3-enoic acid ^ (a) ring hydroxylation (b) ring cleavage Figure 5. Microbial degradation of alkylbenzenes with benzene attached to terminal carbon. -19- SAL ooo 020057 MonofC]o-i6)Alky1benzenes Figure 6. Projected environmental fate of (Cio-16)alKylbenzenes. These compounds are expected to partition Into soil, sediment, and fatty tissue. The rate of biodegradation does not appear to be great enou^i to prevent accumulation In the compartments as Indicated by the hatching. -21- SAL 000020059 Mono(C}o-l6)A1kylbenzenes VI. DATA BASES SEARCHED AND AUTHORS A. DATA BASES SEARCHED fCDLARS fCDLINE CHEfllNE RTECS TDB (Toxicology Data Bank) TOXIINE TOX 65 TOX 74 CANCERLINE CAMCERPROJ 1966-present 1968-present 1977-present 1977-present 1977-present 1965-1973 1974-1976 1967-present 1967-present ORBIT APILIT APIPAT BIOSIS 310SIS 7479 CAS67 CAS72 CAS77 CIN (Chem. Indust. Notes) COM'ENDEX CDI (Comprehensive Dissert. Index) CONFERENCE PAPERS INDEX ENVIROLINE FSTA (Food Scl. Technology Abs.) NT IS OCEANIC PAPERCHEM P/E NEWS POLLUTION ABSTRACTS SAFETY SSIE (Social Science Citation Ind.) TITUS 1964-present 1964-present 1979-present 1974-1979 1967-1971 1972-1976 1977-present 1974-present 1970-present 1861-present 1973-present 1971-present 1969-present 1970-present 1964-present 1969-present 1975-present 1972-present 1975-present 1979-present 1967-present -22- SAL 000020060 MonofCjg)A1kylbenzenes DIALOG AGRICOLA APTIC AQUACULTURE AQUALINE AQUATIC SCIENCE FISHERIES ABSTRACTS CAB ABSTRACTS CLAIMS/US PATENT ABSTRACTS CRIS/USDA ENERGYLINE ENVIRONMENTAL BIBLIOGRAPHY EXCERPTA MEDICA FOODS ADLISRA IMSPEC INTERNATIONAL PHARM. ABS ISfCC IRL LIFE SCIENCES COLLECTION _ MANAGEMENT CONTENTS PHARM. NEWS INDEX PTS PROMT RAPRA ABSTRACTS SCI SEARCH SURFACE COATING ABSTRACTS NELDA SEARCH UORLD TEXTILES 1970-present 1966-1978 1970-present 1974-present 1973-present 1973-present 1971-present 1974-present 1971-present 1974-present 1974-present 1974-present 1969-present 1970-present 1973-present 1978-present 1974-present 1975-present 1972-present 1972-present 1974-present 1976-present 1967-present 1970-present B. AUTHORS This Information Review was prepared by a multidisciplinary team of scientists and technicians. Dr. Satlsh Bhalla was the principal author and compiler. -23- SAL 0C0C2G061 Mono(CjQ_jg)A1kylbenzenes VII. TOXICOLOGICAL AND ECOLOGICAL SUMMARY From Lankas et al. (1978). -24- SAL 000020062 Mono(C]o-l6)A1ky 1benzenes TOXICOLOGICAL AND ECOLOGICAL SUMMARY Authors: Date: Title: Journal: Lankas GR, Baxter C$, Christian RT 1978 Effect of alkane tumor-promoting agents on chemically Induced mutagenesis In cultured Y79 Chinese hamster cells J. Toxicol. Environ. Health 4:37-41 Chemical: Dodecylbenzene (unspecified composition) Biological Parameter Examined: Mutagenicity Species/Tissue: Chinese hamster cells V79 Technique: Y79 Chinese hamster cells were grown In Eagle's minimum essen tial medium supplemented with 1.5 X vitamins and amino acids and 10% fetal calf serum. For routine culture the cells were grown In 75 cm2 plastic tissue culture bottles without antibiotics In an atmosphere of 95% air and 5% CO2. For the mutagenesis assay 2 x 105 cells were seeded In 100-mm plastic petrl dishes In 10 ml growth medium supplemented with 100 units penicillin and streptomycin at 100 ^g/mL. After 2-4 hours, to allow for cell attachment, methylazoxymethanol acetate (MAM) dissolved In medium without serum was added to the plates to a final con centration of 24 jig/mL. After 24 hours of exposure, the medium In the plates was removed and replaced by fresh medium plus the chemical being tested for promoting activity. Dodecylbenzene was mixed with acetone (20 uL/nL) to give a 0.2% v/v solution. Tetradecanoyl acetate diester (TPA) was dissolved in acetone to a concentration of 1 mg/mL. Aliquots of these solutions were added to the cultures after removal of the mutagen. The plates were gently swirled to ensure an even dis tribution of the chemical. Ouabain-resistant mutants were selected by adding growth medium containing inti ouabain 48-72 hours after dosing with MAM. The alkanes were again added so that exposure to the promoter continued throughout ouabain selection. After 2 weeks, the plates were washed, fixed with ethanol, and stained with Glansa, and the number of mutant colonies was determined. Replicates of 10 plates per point were made. Objective To test linear alkanes, an aryl derivative of dodecane and a phorbol ester, for their ability to enhance mutagenesis Induced by the chemical carcinogen MAM. -25- SAL 000020063 Mono(Cio_i5)A1Kyibenzenes TOXICOLOGICAL AMD ECOLOGICAL SUMMARY (continued) Effects Observed At a concentration of 0.7 nM, dodecylbenzene enhanced the fre quency of MAM-1nduded mutations In the cultured cells (Table 1). Dodecylbenzene neither showed mutagenic activity per se nor had an effect on the cell survival rate. Table 1. Comparison of effects of the tetradecanoyl acetate diester (TPA) of phorbol and 1-phenyldodecane on mutation frequency in Y79 cells. Treatment Survival (S) Avg. no. mutants per plate Mutants per 10^ survlvors Control TPA (1.6 jtf) 1-Phenyldodecane(0.7 nM) MAMb (24 iig/mL) MAM + TPAC MAM + 1-Phenyldodecane 90 88 41 29 27 29 1.0 +0.5 0.5 + 0.6 0.4 + 0.6 20.9 + 2.5 26.9 + 2.3 27.7 + 3.5 5.6 2.3 2.2 360 498d 479d aAverage + 95% confidence Interval (t-test). ^MAM - Methylazoxymethanol acetate. CTPA - Tetradecanoyl acetate diester. dp <0.05 -23- SAL 00020Q64 Mono(15)AT kylbenzenes ENCLOSURES Enclosure 1: Enclosure 2: Enclosure 3: From Bingham and Falk (.1969). From Bingham and Falk (1969). From Saffiottl et al. (1962). -27- Sal 00020065 Enclosure 1 From Bingham and Falk (.1969) Table 4.--77ia Cocarc?nogen/c Activity of Variout Concentrations of 1-phenyJdodecsne With Three Concentrations of Bemo[a]pyrene Concentration of Carcinogen and Cocarcincgen 0.05% Benzo[e)pyrene 2-phenyldodecana O to 20 30 40 50 70 too 0.10% Benzo(e)pyrene 1-phenyldodecane 0 to 20 30 40 50 70 too 0.20% Benzo(*)pyrene 1-phcnyldodecane 0 10 20 30 40 50 100 Original ' of Mice 20 15 15 15 15 10 10 10 20 15 15 IS IS 10 10 10 20 10 10 10 10 10 10 Final Effective No. of Mice IS 15 15 14 IS 10 B 10 18 14 15 14 15 9 8 10 20 10 8 8 10 9 10 No. of Miee Developing Tumors Malignant Benign 12 3 15 0 14 1 12 1 15 0 91 8o 91 15 3 11 0 12 3 14 0 IS 0 81 62 10 0 20 0 10 0 80 80 10 0 90 10 0 Av Interval Until Appearance (weeks) 60 29 23 22 18 16 13 11 47 25 23 20 18 18 13 . 12. .40 21 21 19 16 17 10 -28- SAL 000020066 Enclosure 2 From Bingham and Falk (.1969) TABLE skin Tests in Swiss Fi'i'LE Mire. L'sing Twift U'eekiy Topic vt Ah'ucatsvnj vr AtK\ LBtNiENti Initiator None DM B A- Alkvlbenzene sample O (pilot plant) O' O'-A B C u E F G 0 (pilot plant) O' O'A B C L) E __ 4 Initial number 01 animals 10 20 20 bO 40 40 4C 40 20 20 1C 20 JO :o '0 20 JO :o 50 Duration oi the experi ments (weeks} Number ol tumor- bearing animals 50 *6 55 69-76 74-S.5 74-50 6l-.<! 50-5A 61 4 1 0 0 1 0 2 1 0 t 50 6 7b 11 71 i 76 2 76 5 76 1 65 5 TO i 65 0 Total number oi tumors Benign Malignant &2 0l 00 00 r 0 2 l 0 5 ;) 24 .t 1 6 1 6 5 0- 0 0 V c 0 j 4 0 1 1 1 * 7 0 * One application oi a lO olutinn in mineral oil oi T.IJ-dimcthvlbenzIaJanlhraeerie. * Retested a/ter -lorate tor one year in presence oi air. r FIuoreKCM-tree. * Received only the sinclc application 01 OMBA. -29- SA*- 00002C067 Enclosure 3 From Safflottl et al. Cl962) TABLE 2- Skix Test* ix Rabbit*. I'sint. Twice Weekly Tx-hcal XrrLKWTtoxs or Alkylbexiexu and ABS r Sample Concen- Initial Duration of the Number Total number of expert- of tumor tumors iraiion number of mrnt bearing 8c- i't) animali> (weeks* animal* niun Malignant Alkylbenzene sample B Alkvlbenzene `ample D ABS made from sample D 100 100 10 ' aq.) 5 . nr 11C 11* i 0 c 10 c0 0c TABLE Sl'Brl"-T XNI.ul'a Tl.iT* IX Ki-mk Miri. ii <>i iow:n<, x Stvi.: l S l HI I T tvti'i.'i Ixii.ctio.n or \ 1`"i >i*H'TlllN |V Tkli M'KYLIX OF Ai XX LSI S/t \ ANO ABS Duration Sample Alkylbenzrne `ample D ABS made from ample D Initial number of animat* ;o A0 expert* ment (uerk-t of tumorbearir.s animals Total number >l tumors Bvnicn Malignant 95 0 0 0 9$ o 0 0 -30- SAL 000020068 Mono(Cjo-16)Alkylbenzene$ CITED REFERENCES Adachl K, Yamasawa S, Montgna M. 1969. Epidermal hyperplasia Induced by 7,12-d1methylbenz(A)anthracene In proslmlans. J. Natl* Cancer Inst. 42(11:61-68. Bingham E, Falk HL. 1969. Environmental carcinogens. The modifying effect of cocarcinogens on the threshold response. Arch. Environ. Health 19(6):779--783* Brandt L, Verbesselt R. 1972. Kettenlangeeffekte beialkylaryluerblndary. Tetrahedron 28:89-93. Conoco. 1981. Conoco Chemical Corp. Unpublished data on alkylbenzenes and their derivatives, provided by J.J. Hall, March 26, 1981. CPS. 1979. Chemical Products Synopsis. Dodecylbenzene. Mannsvllle, NY: Mannsvllle Chemical Products. Darnall KR, Lloyd AC, Winer AM, Pitts JN Jr. 1976. Reactivity scale for atmospheric hydrocarbons based on reaction with hydroxyl radical. Environ. Scl. Tech. 10(71:692-696. El Masry AM, Smith JN, Williams RT. 1956. The metabolism of alkyl benzenes: iv-propylbenzene and fi-butyl benzene with further observations on Ethylbenzene. Blochem. J. 64:50-56. Gerande HW. 1959. Toxicological studies in hydrocarbons. III. The biochemorphology of the phenylalkanes and phenylalkenes. A.M.A. Archives Industrial Health 19:403-418. Gerarde HW. 1960. Toxicology and Biochemistry of Aromatic Hydrocarbons. New York: Elsevier Pub. Co. Gerarde HW, AhlstromDB. 1966. Toxicologic studies on hY^rocarbons. XI. Influence of dose on the metabolism of mono-n-alkyl derivatives of benzene. Toxicol. Appl. Pharmacol. 9:185-170. Im MJ C. 1968. Glucose metabolism In skin tumor and hyperplasia Induced In the rhesus monkey by 7,12-d1methy1benz(A)anthracene. J. Natl. Cancer Inst. 41(11:73-79 Klrk-Othmer Encyclopedia of Chemical Technology, Vol- 3. New York: John Wiley and Sons, p. 749. Lankas GR, Baxter CS, Christian RT. 1978a. Effect of alkane tumor promoting agents on chemically Induced mutagenesis In cultured V79 Chinese hamster cells. J. Toxicol. Environ. Health 4:37-41. -31- SAL 000020069 Mo no(C}o-16)A1ky1benzene s Lankas GR, Baxter C$, Christian RT. 1978b. Enhancement of chemically Induced mutagenesis In cultured Y79 Chinese hamster cells by alkane tionor-promotlng agents. Toxicol. Appl. Pharmacol. 45(1):222. Leldner H, Gloor R, Wuest D, Wuhrmann K. 1980. The Influence of the sulphonlc group on the blodegradabllIty of n-alKyibenzene- sulphonates. Xenoblotlca 10(1):47-56. ~ Leo A, Hansch C, Elkins D. 1971. Partition coefficients and their uses. Chem. Rev. 71(6):525-616. Little, A.D. Inc. 1977. Human safety and environmental aspects of major surfactants - a report to the Soap and Detergent Association. May 31, 1977. Monsanto. 1981. Monsanto Industrial Chemicals Co. Unpublished data on alkyl benzenes, provided by J.D. Wilson, Feb. 16, 1931. NOHS. 1981. National Occupational Hazard Survey. Cincinnati, OH: National Institute for Occupational Safety and Health. Oliver BG, Cosgrove EG, Carey JH. 1979. Effect of suspended sediments on the photolysis of organics In water. Environ. Scl. Tech. 13C 9): 1075--1077. Palotay JL, Adachi K, Dobson RL, Pinto JS. 1976. Carcinogen induced cutaneous neoplasms In nonhuman primates. J. Nat. Cancer Inst. (USA) 57(6):1269--1274. Papp L, Otvos I, Balthazar Z, Decsy Z, Barrha 8, Palyl G. 1979. Investigation of ortho/para Isometric distribution of dodecylbenzene sulfonic acids. (In Hungarian) Reviewed In Chem. Abstr. 91:22804w. Riegel's. 1974. Soap and Synthetic Detergents. In Riegel's Handbook of Industrial Chemistry, 7th ed. New York: Van Nostrand Reinhold Company, pp. 383-388. Roberts JD, Caserio MC. 1964. Basic principles of organic chemistry. New York, NY: UA Benjamin, 1315 pp. Safflottl U, Shublk P, Opdyke DL. 1962. Carcinogenesis tests on alkylbenzenes and alkybenzene sulfonates. Toxicol. Appl. Pharmacol. 4:763-769. Somaln SM, Teece RG, Schaeffer DJ. 1980. Identification of cocarcinogens and promoters In industrial discharges Into and In the Illinois River. J. Toxicol. Environ. Health 6:315-331. -32- o0oo2ocn0 SAL Mono(Cio_i6)A1kylbenzenes Sarlaslanl $, Harper DB, Higgins IJ. 1974. Microbial degradation of hydrocarbons, catabolism of 1-phenylalkanes by Nocardla salmonlcolor. Blochem. 0. 140:31-45. Thferfelder H, Klenk E. 1924. Weftere Untersuchungen iiber das verbal ten fettaromatischer verblndungen 1m tlerkorper. Hoppe-Seyl. Z. 141:13-28. (In German) Wltco. 1981. Wltco Chemical Corp. Unpublished data on alkylbenzenes, provided by J. Corinth, Feb. 19, 1981. -33SAL 000020071 Mono( C-| o-i 6 )A1 kyl benzenes Lankas GR, Baxter CS, Christian RT. 1973b. Enhancement of chemically Induced mutagenesis In cultured V79 Chinese hamster cells by alkane tumor-promoting agents. Toxicol. Appl. Pharmacol. 45(1):222. Leldner H, Gloor R, Muest D, Wuhrmann K. 1980. The Influence of the sulphonlc group on the blodegradabllIty of n-alkylbenzenesulphonates. Xenoblotlca 10O):47-56. Leo A, Hansch C, Elkins D. 1971. Partition coefficients and their uses. Chem. Rev. 71(5):525-616. Little, A.D. Inc. 1977. Human safety and environmental aspects of major surfactants - a report to the Soap and Detergent Association. May 31, 1977. Monsanto. 1981. Monsanto Industrial Chemicals Co. Unpublished data on alkylbenzenes, provided by J.D. Wilson, Feb. 16, 1931. NOHS. 1981. National Occupational Hazard Survey. Cincinnati, OH: National Institute for Occupational Safety and Health. Oliver BG, Cosgrove EG, Carey JH. 1979. Effect of suspended sediments on the photolysis of organics in water. Environ. Scl. Tech. 13(9J:1075-1077. Palotay JL, Adachl K, Dobson RL, Pinto JS. 1976. Carcinogen Induced cutaneous neoplasms In nonhuman primates. 3. Nat. Cancer Inst. (USA) 57(6): 1269-1274. Papp L, Otvos I, Balthazar Z, Decsy Z, Barrha B, Palyl G. 1979. Investigation of ortho/para isometric distribution of dodecylbenzene sulfonic acids. (In Hungarian) Reviewed In Chem. Abstr. 91:22804*. Riegel's. 1974. Soap and Synthetic Detergents. InRIegel's Handbook of Industrial Chemistry, 7th ed. New York: Van Nostrand Relnhold Company, pp. 383-388. Roberts JD, Caserlo HC. 1964. Basic principles of organic chemistry. New York, NY: WA Benjamin, 1315 pp. Safflottl U, Shublk P, Opdyke DL. 1962. Carcinogenesis tests on alkylbenzenes and alkybenzene sulfonates. Toxicol. Appl. Pharmacol. 4:763-769. Somaln SM, Teece RG, Schaeffer DJ. 1980. Identification of cocarcinogens and promoters In Industrial discharges Into and in the Illinois River. J. Toxicol. Environ. Health 6:315-331. -32- 0020070 sM- 00 Mono(C]o-16)A1kylbenzenes Sarlaslanl S, Harper DB, Higgins IJ. 1974. Microbial degradation of hydrocarbons, catabolism of 1-phenylalkanes by Nocardla salmonicolor. Blochem. J. 140:31-45. Thlerfelder H, Klenk E. 1924. Weltere Untersuchungen u'ber das verhalten fettaromatischer verblndungen 1m tlerkorper. Hoppe-Seyl. Z. 141:13-28. (In German) Wltco. 1981. Wltco Chemical Corp. Unpublished data on alkylbenzenes, provided by J. Corinth, Feb. 19, 1981. -33SAL 000020071