February 20, 2012 

Document Control Office (DCO) (7407M) 

Office of Pollution Control and Toxics (OPPT) 

U.S. Environmental Protection Agency (EPA) 

1200 Pennsylvania Ave NW 

Washington, D.C. 20460 

Attn: 40 CFR 799.5089 (Docket # EPA-HQ-OPPT-2009-0112) 

Re: Notice of Proposed Test Plan 

Dear Sir or Madam: 

Dover Chemical Corporation has committed to respond to this notification for the hazard assessment 

and this letter serves as a proposed test plan under the above TSCA Section 4 Test Rule covering 

CAS # 72162-15-3 (1-Decene, sulfurized). The attached summary shows data availability and 

proposed testing on 1-Decene, sulfurized and is committed to respond if approved. 

Please consider our detailed summary and reasoning for our proposed testing. If you have any 

question, please contact me at 330-365-3610. 

Sincerely, 

Tim Nowicki 

Manager Product Compliance 

Dover Chemical Corporation 

tnowicki@doverchem.com 
Dover Chemical Corporation – HPV Additional Testing 

February 20, 2012 

Page 1 of 10 

TSCA 4 issue on Sulfurized, 1-Decene, 

The US EPA has promulgated (effective November 21, 2011) a test rule 

under TSCA 4 for the chemical 1-Decene, sulfurized (CAS #72162-15-3). Dover 

Chemical Corporation has committed to respond to this notification for the hazard 

assessment. The chemical was originally entered into the EPA’s HPV Challenge 

program in the Group 1 Alkyl Sulfides class, but was withdrawn from the ACC’s 

HERTG’s efforts before completion of its HPV efforts. A final submission on alkyl 

sulfides related to sulfurized, 1-Decene was submitted to the Agency on May 18, 

2005. This report provides substantial information relevant to completion of the 

hazard characterization of this chemical. 

The EPA has specified various testing needs for this chemical as follows: 

Physical/Chemical Elements

1) Boiling point 

2) Vapor pressure 

3) Partition coefficient 

4) Water solubility 

Environmental Fate and Pathways Elements 

1) Biodegradation 

Ecotoxicity Elements 

2) Chronic daphnia 

3) Algal 

Health Elements 

1) Acute toxicity (up-down) 

2) Bacterial reverse mutation - Ames 

3) Genetic toxicity in vivo (chromosomal aberrations) 

4) Combined repeated dose with developmental toxicity/teratogenicity screen 

Composition of Sulfurized, 1-Decene Product 

 This substance is manufactured by reacting molten sulfur with 1-decene. 

The decene feedstock is a mono-unsaturated highly branched C10 hydrocarbon. 

The reaction product consists of multiple sulfurated alkane and alkene 

components with the lowest plausible molecular weight member (with possibly 

higher biological reactivity) being the decyl decenyl monosulfide compound with 

MW = 312. Higher molecular weight constituents contain multiple sulfur atoms 
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February 20, 2012 

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with decyl oligomers, many resulting in chemical entities with molecular weights 

exceeding 1000. 

Gel permeation chromatographic analysis has been performed on this 

product. It shows the weight fraction above 1000 MW is 82.4% while the weight 

fraction below 500 MW is 3.8%. The Weight Average (Mw) for the substance = 

1332 and the Number Average (Mn) = 560. The high molecular weight 

constituents contain sequences of 1-6 or more sulfur atoms at multiple locations 

within the constituents’ structures. Overall, this product is one, that by virtue of 

its composition being primarily chemical entities >500 molecular weight, will 

possess diminished likelihood that elevated bioavailability and toxicity will be 

characteristics of this substance. 

 

QSAR data for plausible structures of lower molecular weight decyl 

sulfides were developed using the EpiSuite models. Structural homologs varied 

according to sulfur content, branching and cyclicity. Findings for important 

endpoints are presented below: 

Chemical 

(SMILES) MW 

BP 

(C) 

Water 

sol 

(mg/L) 

log 

Kow 

Algal 

EC50 

(mg/L) 

Chronic 

Daphnid 

ChV (mg/L) 

Biodegradation 

Biowin 2 & 3 

CCCCCCCCC(C) 

SCC=CCCCCCCC 

Monosulfide n-alkyl 

312 364 8 x 10-5 9.5 0.00133* 4.1x10-5 0.905 & 3.1 wks 

CCCCCCCCC(C) 

SCC=CCCCCCCC 

Monosulfide, branched 

312 320 3 x 10-3 9.4 0.0015* 4.9 x10-5 0.0014 & 1.9 mo 

CCCCCCCCC(C) 

SSCC=CCCCCCCC 

Disulfide n-alkyl 

345 397 8 x 10-6 10.4 0.00037* 8.9 x 10-6* 0.858 & 3.0 wks 

CCCCCCCCC(C) 

SSSCC=CCCCCCCC 

Trisulfide n-alkyl 

376 431 7 x 10-6 10.4 0.00040* 9.7 x 10-6* 0.793 & 2.9 wks 

CCCCCCCCC(C)SSS 

SSSCC=CCCCCCCC 

Hexasulfide n-alkyl 

473 531 5 x 10-6 10.4 0.00040* 1.2 x10-5 0.495 & 2.7 wks 

CCCCCCCCCC1SCC 

(SC1)CCCCCCCC 

Disulfide, cyclic 

345 400 5 x 10-5 9.1 0.003* 8.7 x10-5 0.858 & 3.0 wks 

CCCCCCCCCC1SSCC 

(SSC1)CCCCCCCC 

Tetrasulfide, cyclic 

409 466 5 x 10-7 11.0 0.00019* 3.9 x 10-6* 0.709 & 2.9 wks 

* Chemical solubility is below these estimated toxic concentrations, and thus, chemical 

unlikely to be toxic even at saturated levels in aquatic environments. 

The results above indicate most importantly the extremely low water 

solubilities for all structures within a wide range of molecular weights. This is in 

concert with findings that all exhibit partition coefficients in excess of 6.0. Aquatic 

toxicity estimates indicate that for the 2 species (algae and daphnia), actual 

toxicities are not likely to be observed due to the extremely low limits for water 

solubilities of these substances. Biodegradation estimates show some prospect 
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February 20, 2012 

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for this activity in microbial environments except for the branched compound 

which best represents the subject chemical. Low potential for biodegradation 

(driven by alkyl branching) often parallels fact that such substances are less 

likely to be metabolized in animal models, lowering possibility of bioactivation by 

metabolic means. Given the lack of reactive functional groups in alkyl sulfides 

plus the high degree of branching that exists on alkyl groups, these substances 

exhibit low potentials for biological activities including toxicity. 

 

Application of HPV Alkyl Sulfide Data to Sulfurized, 1-Decene 

The subject chemical sulfurized, 1-decene (CAS 72162-15-3) was 

withdrawn from the ACC’s HPV project on alkyl sulfides that was completed and 

reported to the Agency on May 18, 2005. The report, however, does contain 

data relevant to the assessment of sulfurized, 1-decene given the numerous 

similarities in structures and composition of those products. The tables below 

present summaries of data on structurally-related alkyl sulfides along with 

endpoint estimates for the TSCA 4 chemical. 

The relevance of these data to this chemical lies in the fact that: 

 All are primarily composed of highly branched alkanes, 

 Most exhibit mean molecular weights above 400, 

 They lack reactive functional groups, and 

 Members of this chemical group share high boiling points/low volatility, 

low water solubility, and high partition coefficients. 

The sulfurized 1-decene chemical has its most closely-related substances as #2 

& #3 below derived from C8 and C15-18 alkenes, respectively. 
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February 20, 2012 

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TABLE 1. Estimated Physicochemical Properties of Structurally-Related Alkyl 

Sulfides and Estimate for Sulfurized, 1-decene 

CHEMICAL 

Molecular 

Weight 

(mean) 

Boiling 

Point 

Water 

Solubility 

(mg/L) 

Vapor 

Pressure 

(Pa) 

Partition 

Coefficient 

(log Kow) 

#1 

1-Propene, 2-

methyl-, sulfurized 

160-1600; 

(480) 

Decomp. 

>200 C 

1.29 <1 x 10-3 >6.0 

#2 

Pentene, 2,4,4-

trimethyl-sulfurized 

594-658 Decomp. 

>200 C 

2.35 x 10-6 m <1 x 10-3 >6.0 

#3 

Alkenes, C15-18, 

alpha, sulfurized 

520 Decomp. 

>200 C 

1.59 x 10-10 m <1 x 10-3 >6.0 

1-Decene, 

sulfurized 

Mn = 560 

Mw = 1332 

<500 Mw = 

3.8%

Decomp. 

>300 C 

<2.0 x 10-5

 <1 x 10-4 >6.0 

Rationale for 1-

Decene, sulfurized 

values 

GPC 

assessment 

(report 

attached) 

Bridging from 

Chemicals 

#1 – 3 plus 

modeling* 

Bridging from 

Chemicals 

#2 – 3 plus 

Modeling* 

Bridging 

Chemicals 

#1 – 3 plus 

modeling* 

Bridging from 

Chemicals 

#1 – 3 plus 

modeling* 

* EpiSuite modeling of a sulfurized, 1-decene dimer which is low MW entity in this 

reaction product. SMILES formula CCCCCCCCC(C)SSSCC=CCCCCCCC 

m – modeled data 

The above projected values for the subject chemical appear to be reliable 

estimates given the outcomes for these related compounds with the exception of 

water solubility for #1. Modeling would project a much lower value that what was 

reported for this substance.
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February 20, 2012 

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TABLE 2. Environmental Fate of Structurally-Related Alkyl Sulfides and Estimate 

for Sulfurized, 1-decene 

CHEMICAL 

Biodegradability Hydrolysis 

#1 

1-Propene, 2-

methyl-, 

sulfurized 

0.3% biodegraded after 28 

days 

Not applicable 

1-Decene, 

sulfurized 

Not biodegradable Not applicable 

Rationale for 

1-Decene, 

sulfurized 

value 

Bridging from chemical #1 plus 

modeling*. Fact that highly 

branched alkanes tend to be 

non-biodegradable 

Chemicals contain no hydrolyzable functions 

* EpiSuite modeling of sulfurized,1-decene dimer which is low MW entity in this reaction 

product. SMILES formula CCCCCCCCC(C)SSSCC=CCCCCCCC 

All indications are the TSCA 4 compound would not biodegrade due to results 

from #1 chemical. This is supported by low potential estimated by BIOWWIN 

modeling of the above structure. In addition, the extremely low water solubility of 

the compound would prevent evidence of significant degradation in standard lab 

assays. 

TABLE 3. Ecological Toxicity Structurally-Related Alkyl Sulfides and Estimate for 

Sulfurized, 1-decene 

CHEMICAL 

Acute Toxicity 

in Algae 

Acute Fish Acute Daphnia Chronic 

Daphnia 

#1 

1-Propene, 2-

methyl-, 

sulfurized 

EC50 >100 

mg/L, WAF 96 

hr method 

>1000 mg/L, 

WAF 96 hr 

>1000 mg/L, 

WAF method 

None 

1-Decene, 

sulfurized 

>100 mg/L Negligible 

toxicity 

Negligible 

toxicity 

2.2 x 10-5 

mg/L

Rationale for 1-

Decene, 

sulfurized value 

Bridged from 

Chemical #1 plus 

modeling* 

(indicates toxicity 

below solubility 

limit) 

Bridged from 

Chemical #1 plus 

modeling* 

(indicates toxicity 

below solubility 

limit) 

Bridged from 

Chemical #1 plus 

modeling* 

(indicates toxicity 

below solubility 

limit) 

Modeling* 

(indicates 

toxicity below 

solubility limit) 

* ECOSAR modeling of sulfurized, 1-decene dimer which is low MW entity in this 

reaction product. SMILES formula CCCCCCCCC(C)SSSCC=CCCCCCCC 
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February 20, 2012 

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All results on similar alkyl sulfides point to lack of aquatic toxicities to several 

species under conditions that employ means to achieve maximal aquatic 

chemical concentrations. This is further supported by modeling results that 

indicate toxicities may occur at aquatic levels only in excess of the chemical’s 

solubility limit. 

TABLE 4 . Acute Toxicities of Structurally-Related Alkyl Sulfides and Estimate 

for Sulfurized, 1-decene 

CHEMICAL Acute Toxicities 

#1 

1-Propene, 2-methyl-, sulfurized 

Oral LD50 >5000 mg/kg (rat) 

Inhalation LC50 >0.39 mg/L (rat) 

#2 

Pentene, 2,4,4-trimethyl-sulfurized 

Oral LD50 >5000 mg/kg (rat) 

Dermal LD50 >2000 mg/kg (rabbit) 

3 inhalation tests – LC50 >4.3 mg/L 

rats, mice, guinea pigs 

#3 

Alkenes, C15-18, alpha, sulfurized 

Dermal LD50 >2000 mg/kg (rabbit) 

1-Decene, sulfurized Very low 

Rationale for 1-Decene, sulfurized value Bridging from Chemicals #1-3 

Empirical information on the 3 related chemicals demonstrate low toxic potentials 

by all routes of administration. This is consistent with findings for high molecular 

weight alkyl compounds lacking reactive functional groups. 
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February 20, 2012 

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TABLE 5. Repeated Dose and Reproductive/Developmental Toxicities of 

Structurally-Related Alkyl Sulfides and Estimate for Sulfurized, 1-decene 

CHEMICAL Repeated Dose Toxicity Reprod/ Devel. 

Toxicity 

#1 

1-Propene, 2-

methyl-, 

sulfurized 

Study 1 

13-wk dermal (rat), doses 10 – 2000 mg/kg-day. 

LOEL = 250 mg/kg for dec. body wt, dec. RBCs, 

incr. neutrophils, spleen size with pigmentation, 

incr. WBC production in spleen and bone 

marrow, NOEL = 50 mg/kg (systemic) with 10% 

dermal irrritation. 

Study 2 

28-day dermal (rabbit), doses 200 or 2000 

mg/kg-day (intact & abraided skin). >200 mg/kg 

– severe skin irritation, 2000 mg/kg – decr. Body 

wt and food consumption. NOEL <200 mg/kg 

Study 3 

21-day dermal (rabbit). 140, 560, 2240 mg/kgday. 

>140 mg/kg – severe erythema, slight/moderate 

edema, epithelial hyperplasia in all animals 

NOEL <140 mg/kg. 

None 

#2 

Pentene, 

2,4,4-trimethylsulfurized 

Study 1 

28-day inhalation (rat) 15, 50, 150 mg/m3

. Trend 

toward decr. body wt gains at >15 mg/m3

. Incr. 

kidney wts (males) with hyaline droplet formation 

in proximal tubules, increased liver wts (highdose male & females, mid-dose males); 150 

mg/m3 – decr. hemoglobin concentration. NOEL 

<15 mg/m3 

Study 2 

28-day dermal (rat) 1000 mg/kg-day. Irritating 

to skin with erythema, mild multifocal eschar and 

mild hemorrhage in underlying dermis. NOEL 

<1000 mg/kg 

None 

1-Decene, 

sulfurized 

Very low potential for repeated dose toxicities. Low potential for 

reproductive, or 

developmental 

effects

Rationale for 

1-Decene, 

sulfurized 

value 

Bridging from Chemicals #1 & 2, fact that this 

chemical class has high molecular weights, and 

exhibit negligible effects in other toxicity tests 

(e.g., acute toxicity, genetic, and aquatic testing) 

Same as repeated 

dose toxicity 

rationale 

Toxicity exhibited in these repeat dosing tests following dermal exposures 

indicate skin irritation effects in rats and rabbits. Some evidence of systemic 

effects (blood, splenic parameters) was observed in one study. Inhalation 
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February 20, 2012 

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exposure (#2) induced evidence of kidney lesions in male rats (hyaline droplets) 

which are considered not relevant to human health. 

Application of these data to project potential effects associated with the 

subject chemical results in conclusion that (a) the systemic effects are mild and 

likely reversible, and (b) suggest sulfurized, 1-decene is irritating to the dermal 

surface of rodents and rabbits. These findings are consistent with expected 

results from high exposures to higher alkanes and other low reactivity 

substances following high exposures. 

TABLE 6. Genetic Toxicity Properties of Structurally-Related Alkyl Sulfides and 

Estimate for Sulfurized, 1-decene 

CHEMICAL 

Gene Mutations 

(bacterial) 

In Vitro Chromosomal 

Aberration 

In Vivo Chromosomal 

Aberration 

#1 

1-Propene, 2-methyl-, 

sulfurized 

Negative +/- S9 – Negative - chromosomal 

aberrations (mouse) 

Negative micronucleus 

(rat) 

#2 

Pentene, 2,4,4-

trimethyl-sulfurized 

Negative +/- S9 – 

 

Negative - chromosomal 

aberrations (mouse) 

#3 

Alkenes, C15-18, 

alpha, sulfurized 

Negative +/- S9 – Negative - chromosomal 

aberrations; test 

conducted 

on C12-16 analog 

1-Decene, sulfurized Negative Negative Negative 

Rationale for 1-

Decene, sulfurized 

value 

Bridging from 

Chemicals #1 – 3 

Bridging from in vivo 

results on Chemicals 

#1 – 3 

Bridging from Chemicals 

#1 – 3 

Three chemically-related substances were subjected to both Ames and in vivo 

chromosomal aberration testing, and none showed evidence of either mutagenic 

or clastogenic activity. These data plus the absence of reactive functional groups 

on this chemical argues convincingly against a genotoxic potential for sulfurized, 

1-decene. 

Summary 

 The subject chemical, sulfurized, 1-decene, has been characterized by 

GPC, and shown to be primarily composed of higher molecular weight (Mw = 

1332, Mn = 560) constituents. 96+% of the product by weight has molecular 

weight >500. This chemical composition in addition to (a) data developed for 

related chemicals from the HPV reporting of Alkyl Sulfides, (b) a significant body 
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February 20, 2012 

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of information from QSAR modeling of lower molecular weight structures 

suggesting negligible potential for aquatic toxicity or biodegradation, and (c) 

knowledge that the alkyl groups in this product are highly branched (diminished 

potential for biodegradation or bioactivation), all contribute to conclusion that this 

product has low-level biological reactivity of any kind. This outcome suggests 

development of significant amount of new data for this chemical is not warranted. 

 Below is a table with a proposal for the status of current information on 

this chemical as well as indications for new testing. 

Table 7. Data Availability and Proposed Testing for 1-Decene, Sulfurized 

Boiling 

Point 

Vapor 

Pres. 

Part. 

Coef. 

Water 

Sol. 

Biodeg. Chronic 

Daphnia

Algal Acute

Oral 

Ames Chrom 

Ab. 

Rep. 

Dose/ 

ReproDevelop. 

B, C B, C B, C B, C, 

T 

B, C, 

NA 

C, NA B, C, 

NA 

B, T B B B 

B – bridging 

C – computerized QSAR modeling 

NA – Not applicable based upon physiochemical properties of substance, primarily low 

water solubility which makes certain tests not feasible 

T – testing to be performed 

Overall, the need for test data development appears to be very limited for the 

TSCA chemical based upon: 

 Evidence of low biological activity for related compounds from tests assessing 

acute toxicity, aquatic effects in multiple species, and genetic endpoints, 

 The higher molecular weights for this and the related chemicals indicate a 

position that projects low potential for adverse biological activities, 

 QSAR results also provide support to indicate low water solubility limits with 

low aquatic dispersal, resulting in diminished toxic potential to aquatic 

species. 

In order to provide data on this specific chemical, Dover agrees to conduct 

the following tests. 

 Water solubility 

o New data can be used to characterize this endpoint for sulfurized, 1-

decene which has not previously been determined. Results will likely 

verify the product exhibits negligible solubility, negating need for further 

testing for aquatic toxicity, 
Dover Chemical Corporation – HPV Additional Testing 

February 20, 2012 

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 Acute oral toxicity (up-and-down test - rat) 

o Data to assess mammalian toxicity at high dose levels. Absence of 

toxicity would indicate substance lacks biological reactivity, thus 

providing evidence of minimal concern for repeated dose or 

reproductive/developmental activity for the substance.