### 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 respo nd to this notification fo r 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 a ttached summary shows data availability and proposed testing on 1-Decene, sulfurized a nd is committed to respond if approved.

Please consider our detailed summary and reasoni ng 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

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### TSCA 4 issue on Sulfurized, 1-Decene,

The US EPA has promulgated (effectiv e 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 res pond 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 The chemical was originally entered into the EPA’s HPV Challenge program in the Group 1 Alkyl Sulfides class, but was withdrawn from the ACC’s HERTG’s efforts before completion of its H PV efforts. A final submission on alkyl sulfides related to sulfurized, 1-Dec ene was submitted to the Agency on May 18, 2005. This report provides substantial in formation 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 Sulfur ized, 1-Decene Product

This substance is manufactured by reacting molten sulfur with 1-decene.
The decene feedstock is a mono-unsatur ated highly branched C10 hydrocarbon. The reaction product consists of mu ltiple sulfurated alkane and alkene components with the lowest plausible mole cular weight member (with possibly higher biological reactivity) being the de cyl decenyl monosulfide compound with MW = 312. Higher molecular weight cons tituents contain mult iple sulfur atoms

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### with decyl oligomers, many resulting in chemical entities with molecular weights exceeding 1000.

Gel permeation chromatographic anal ysis has been performed on this product. It shows the weig ht fraction above 1000 MW is 82.4% while the weight
fraction below 500 MW is 3.8%. The Wei ght 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’ struct ures. Overall, this product is one, that by virtue of its composition being prim arily chemical entities >500 molecular weight, will possess diminished likelihood that elev ated 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 im portantly 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 (a lgae and daphnia), actual toxicities are not likely to be observed due to the extremely low limits for water
solubilities of these substances. Biod egradation estimates show some prospect

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### for this activity in microbial envir onments except for the branched compound which best represents the s ubject 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 reacti ve functional groups in alkyl sulfides plus the high degree of branching that ex ists 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 sulfuriz ed, 1-decene (CAS 72162-15-3) was
withdrawn from the ACC’s HP V 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 asse ssment of sulfurized, 1- decene given the numerous similarities in structures and compositi on of those products. The tables below present summaries of data on structura lly-related alkyl su lfides 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 shar e 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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### TABLE 1. Estimated Physicochemical Pr operties 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 s ubject chemical appear to be reliable estimates given the outcomes for these re lated compounds with the exception of water solubility for #1. Modeling would pr oject a much lower value that what was reported for this substance.

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### TABLE 2. Environmental Fate of Structurally-Related Al kyl 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 support ed by low potential estimated by BIOWWIN modeling of the above structure. In addition, the extremel y low water solubility of the compound would prevent evidence of significant degradation in standard lab

assays.

TABLE 3. Ecological Toxicity Structura lly-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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### 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 furt her supported by m odeling results that indicate toxicities may occu r at aquatic levels only in excess of the chemical’s solubility limit.

TABLE 4 . Acute Toxicities of Structurally-Related Al kyl 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 chem icals demonstrate low toxic potentials by all routes of administration. This is consistent with findings for high molecular weight alkyl compounds lacking r eactive functional groups.

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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 321-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/m 3 . Trend toward decr. body wt gains at >15 mg/m 3 . Incr. kidney wts (males) with hyaline droplet formationin proximal tubules, increased liver wts (highdose male & females, mid-dose males); 150 mg/m 3 – decr. hemoglobin concentration. NOEL <15 mg/m 3 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 par ameters) was observed in one study. Inhalation

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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 dat a to project potential e ffects associated with the subject chemical results in conclusion t hat (a) the systemic effects are mild and likely reversible, and (b) suggest sulfuriz ed, 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-R elated 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 aga inst a genotoxic potential for sulfurized,
1-decene.

Summary

The subject chemical, sulfurized, 1-decene, has been characterized by GPC, and shown to be primarily compos ed of higher molecular weight (Mw = 1332, Mn = 560) constituents. 96+% of the product by weight has molecular weight >500. This chemical compositi on in addition to (a) data developed for related chemicals from the HPV reporting of Alkyl Sulfides, (b) a significant body

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### of information from QSAR modeling of lower molecular weight structures suggesting negligible potent ial for aquatic toxicity or biodegradation, and (c) knowledge that the alkyl gr oups 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 da ta for this chemical is not warranted.

Below is a table with a proposal fo r the status of current information on
this chemical as well as i ndications 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 developm ent appears to be very limited for the TSCA chemical based upon:

 Evidence of low biological activity fo r related compounds from tests assessing acute toxicity, aquatic effects in mult iple species, and genetic endpoints,

 The higher molecular weights for this and the related chemicals indicate a position that projects low potential for adverse biolog ical 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 specif ic chemical, Dover agrees to conduct the following tests.

 Water solubility

o New data can be used to characteri ze 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,

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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 acti vity for the substance.