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April4, 2014 

Via E-mail and Certified Mail 

OPPT CDR Submission Coordinator 

Mail code 7 407M 

Attn: Inventory Update Reporting and 

Chemical Data Reporting 

Office of Chemical Safety and Pollution 

Prevention 

Environmental Protection Agency 

1200 Pennsylvania Ave., NW. 

Washington, DC 20460 

Writer's Direct Access 

Herbert Estreicher, J.D., Ph.D. 

(202) 434-4334 

estreicher@khlaw. com 

Re: Request For Exemption Of Epoxidized Soybean Oil From TSCA 

Chemical Data Reporting (CDR) Processing And Use Information 

Reporting Requirements In 2016 

Dear Sir or Madam: 

The National Oilseed Processors Association (NOPA) hereby requests the U.S. 

Environmental Protection Agency (EPA) to exempt "Epoxidized Soybean Oil" (EPSO, CASRN 

8013-07-8) from the Toxic Substances Control Act (TSCA) Chemical Data Reporting (CDR) 

processing and use reporting requirements (Part III of the reporting form, Form U) pursuant to 40 

C.F .R. 711.15(b )(2)(iii). ESBO is of low risk to human health and the environment. 

I. BASIS FOR PETITION 

EPA regulations at 40 C.F.R. § 711.15(b)(2)(iii) permit any person to request that the 

EPA amend the list of substances of "low current interest" that are partially exempt from CDR 

requirements, specifically from the processing and use reporting requirements contained in 40 

C.F.R. § 711.15(b)(4). EPA states that in making the determination of whether this partial 

exemption should apply to a particular chemical substance, EPA will consider the totality of 

information available for the chemical substance in question, including but not limited to, certain 

enumerated considerations at 40 C.F .R. § 711.15(b )(2)(ii). 

The supporting attachments to this petition address each of the six exemption 

considerations for ESBO. Most importantly, our petition demonstrates that there is "low current 

interest" in CDR processing and use data for this product because it is of low potential human 

and environmental risk; is comprehensively regulated by other state and federal agencies, in 

Washington, D.C. Brussels San Francisco Shanghai 

www.khlaw.com 
KELLER AND HECKMAN LLP 

OPPT CDR Submission Coordinator 

April4, 2014 

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particular the U.S. Food and Drug Administration; has a long history of safe use in food-contact 

and non-food products; and offers great promise for environmentally beneficial and sustainable 

alternatives to traditional synthetic chemistry. 

Based on these and the other considerations discussed below, we are confident that the 

EPA will conclude that this substance should be added to the list of CDR partially exempt 

substances. 

II. TSCA REGULATED USES 

According to the SIDS Initial Assessment Report (SIAR), ESBO is approved for use as 

an inert ingredient in pesticides; the product is used as an acid scavenger to protect the 

application equipment from corrosion, rather than as an active ingredient in the pesticide. It is 

also used as a plasticizer in PVC for a wide range of applications including food-contact 

materials and has approvals under EU and FDA regulations. 

Even though the subject request is to partially exempt ESBO for the 2016 CDR reporting 

cycle, NOP A requests that the EPA provide its response to this petition within the 120 days 

contemplated under 40 C.P.R. 711.15(b)(2)(iii)(A). 

* * * 

Sincerely yours, 

~~ Herbert Estreicher, Esq. 

Enclosures 
CDR J>etition for Certain Food-Use Substances 

40 C.F.R. § 711.415(b)(2)(ii)(A) Criterion Information 

(Whether the chemical qualifies or has qualified in past IUR collections for the reporting of 

the information described in§ 711.15(b)(4)) 

Publicly available information on the 1986-2006 IUR database and the 2012 CDR 

database was searched for ESBO to determine whether the substance meets the criteria of 

"whether the chemical qualifies or has qualified in past IUR collections for the reporting of 

information described in §711.15(b)(4)." See 40 C.P.R.§ 711.15(b)(2)(ii)(A). It was reported in 

the 2006 IUR and the 2012 CDR. 

Processing and use data were provided by 18 companies in the 2012 CDR. The 2012 

CDR volume was reported as 148,763,647lbs. per year. Data reported to EPA on a confidential 

basis for purposes of IUR or CDR are not necessarily reflected in this submission. The Agency is 

respectfully requested to review the IUR or CDR database for confidential data to supplement 

the data provided. 

CDR Petition for Certain Food-Use Substances 

40 C.F.R. § 711.415(b)(2)(ii)(B) Criterion Information 

(The chemical substance's chemical and physical properties or potential for 

persistence, bioaccumulation, health effects, or environmental effects (considered 

independently or together)) 

Extensive data were developed by EPA for ESBO in the OECD SIDS Initial Assessment 

Report for the Epoxidized Oils and Derivatives (EOD) Category, which is provided as an 

attachment to this document. The following provides a summary of the data from this report. 

Data Available on Epoxidized Soybean Oil (ESBO) (CASRN 8013-07-8) from the 

OECD SIAR 

1) Substance identity profile 

a. Substance identifiers 

CAS name: Epoxidized soybean oil (ESBO) 

Other names: Epoxidized soy oils 

Epoxidized soya oils 

Fatty acid, soybean oil, epoxidized 

Soybean oil, epoxidized 

CASRN: 8013-07-8 

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Molecular structure: 

Soybean oil, the natural product from which ESBO is 

derived, is a triglyceride, with a typical fatty acid 

distribution of linoleic ( 49-57% ), oleic (26-36% ), and 

linolenic (1-2%) acids constituting the major unsaturated 

fatty acid components. Saturated fatty acid components 

constitute about 14% of the mixture. Epoxidation at most 

or all of the points of unsaturation (double bonds between 

carbon atoms) in the fatty acid chains gives a variety of 

products collectively known as epoxidized soybean oil. 

The alcohol portion of this molecule is glycerol. 

b. Physical-chemical properties' 

Physical state liquid 

Melting point: -2.2 degC 

Boiling point: Decomposes at 201 degC 

Relative densitv 0.9875- 0.9930 g/cm3 at 25 degC 

Vapour pressure <0.001 Pa at 25 degC (estimated) 

Partition coefficient (log Kow) Log Pow= -1.72 at 20°C 

Water solubility: 0.00099 g/L at 20 degC (estimated) 

Partition coefficient n-octanol/water >6.2 (estimated) (log value) 

Saturated fatty acid components(%) 14 

Epoxy values(%) 6.8-7.1 

c. Manufacturing 

Soybean oil, the natural product from which ESBO is derived, is a triglyceride, with a 

typical fatty acid distribution oflinoleic (49-57%), oleic (26-36%), and linolenic (1-2%) 

acids constituting the major unsaturated fatty acid components. Saturated fatty acid 

components constitute about 14% of the mixture. Epoxidation at most or all of the points 

ofunsaturation (double bonds between carbon atoms) in the fatty acid chains gives a 

variety of products collectively known as epoxidized soy bean oil. ESBO may be 

produced by oxidation of soybean oil with hydrogen peroxide. 

d. Uses 

According to the SIAR, ESBO is approved for use as an inert ingredient in pesticides; the 

product is used as an acid scavenger to protect the application equipment from corrosion, 

rather than as an active ingredient in the pesticide. It is also used as a plasticizer in PVC 

for a wide range of applications. FDA regulates ESBO as a direct additive for use in 

brominated soybean oil and as an indirect additive for a variety of uses in food-contact 

materials. 

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2) Toxicological profile 

a. Human Toxicity 

Information about the toxicology and environmental effects and fate ofESBO is 

summarized in the OECD SIAR. 

In mammalian species, ESBO is expected to be absorbed and metabolized, resulting in 

the release of free epoxidized fatty acids and lesser substituted alcohols or glycerides. 

Lipase is an enzyme that assists in the breakdown and digestion of fat in the body. 

Pancreatic lipase works at the oil/water interface, because triglycerides are insoluble. 

During metabolism in the GI tract, pancreatic lipase preferentially hydrolyzes 

triglycerides to release the free fatty acids from the SN-1 and SN-3 (terminal) positions of 

the glycerol backbone. Other products of metabolism are mono- and diglycerides. The 

monoglycerides, diglycerides, and fatty acids can be absorbed. In a similar manner, 

pancreatic lipase and other digestive enzymes have been shown to hydrolyze propylene 

glycol monoesters and diesters in vitro. The absorption, metabolism and hydrolysis of 

propylene glycol distearate were studied in rats using isotopically labelled compounds. 

These processes for the propylene glycol esters were found to be similar to those of the 

glycerol esters. So, there is evidence that the propylene glycol esters of fatty acids are 

hydrolyzed to propylene glycol and fatty acids. Further hydrolysis can also occur via 

carboxylesterase activity. 

Acute toxicity studies have been conducted with ESBO via the dermal and oral route of 

exposure. The dermal LD50 in rabbits is greater than 20 mL/kg bw. The oral LD50s in 

rats is up to 41.5 mL/kg bw. There is no valid definitive skin irritation study for ESBO; 

however the results from a dermal toxicity study indicate transient erythema and 

desquamation (no to slight skin irritation). An eye irritation study indicates no damage is 

observed. A skin sensitization test indicates that ESBO is not a sensitizer. 

In a 90-day subchronic study, male and female rats were given 0.04, 0.2, 1.0 or 5.0% (5% 

is approximately 1.25 g/kg bw/d) ESBO. Liver weights were increased in rats fed ESBO 

at 1% or 5% in diet. Gross findings indicated a test article-related effect of ESBO on liver 

and kidney at 1% and 5%. The NOAEL was 0.2% ESBO; the LOAEL was 1% ESBO. In 

a 2-year rat feeding study, a LOAEL of 1% ESBO was described based on increased liver 

and kidney weights. No effects were observed at 0.5% ESBO. Rats were given diets 

containing up to 5% ESBO for 15 weeks. Temporary slowed growth and liver and kidney 

enlargement at concentrations greater than 1.5% were observed. The LOAEL was greater 

than 1.5% ESBO. Groups of three dogs were fed up to 5% ESBO once per day for one 

year. Dogs fed 5% ESBO lost weight, and fatty liver changes (fatty infiltration) in one 

dog given 5% ESBO were observed. Food intake and body weight were decreased at 5% 

ESBO. The LOAEL was 5% ESBO. In vitro, ESBO was negative in bacterial or 

mammalian gene mutations assays. ESBO did not induce chromosomal aberrations in 

Chinese hamster V79 or human lymphocyte cells. 

Chronic/carcinogenicity studies were conducted with ESBO by the oral route (dietary). 

ESBO was not carcinogenic when fed to rats at up to 2.5% of the diet. Further, the 

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NOAEL was 2.5%, providing an average daily intake of approximately 1.0 g/kg bw in 

males and 1.4 g/kg bw in females. There were no treatment-related histopathologic 

lesions and there was no evidence of carcinogenicity of ESBO in groups of male and 

female rats given ESBO in the diet at 0, 0.1, 0.5, 1.0, 2.5, and 5.0%. 

ESBO has been evaluated for the potential to cause developmental toxicity in rats and 

was not teratogenic, nor did it demonstrate reproductive toxicity. Daily administration of 

ESBO up to 1000 mg/kg bw/d did not induce any toxic effect in parent male or female 

animals, did not disturb their capacity for reproduction and did not impair development of 

the F1 offspring. 

b. Ecological Toxicity 

As summarized in the SIAR: 

"Acute toxicity tests with fish (48 hr.) as well as tests with both freshwater and marine 

crustacea (24 hr.), and algae (72 hr.) have been conducted with ESBO. Although the fish 

and invertebrate studies were conducted for shorter time periods than currently specified 

in the OECD guidelines, for the time periods examined there was no or minimal evidence 

of toxicity observed at the limit of water solubility. In the algae study with ESBO, on the 

basis of biomass, the median effective concentration was 72 h EbC50 > 8 mg/L and 72 h 

NOEC = 2.3 mg/L. Effects are not expected to be observed below the water solubility of 

these materials. Based on the physicochemical properties ofESBO (very low water 

solubility, log Kow values > 6.2, and readily biodegradable), it is unlikely to be 

bioavailable to aquatic organisms." 

3) Environmental Fate 

Data from the SIAR on environmental fate are as follows: 

"The melting point of is ESBO is -2.2 C. As it decomposes at 201 C, boiling points are 

not applicable. The vapor pressures is estimated to be <0.001 Pa. The reported vapor 

pressure value is presumed to reflect the influence from minor impurities having 

relatively low boiling impurities. The estimated water solubility is estimated at 0.99 

mg/L. It is the nature of the epoxidized oils to form an emulsion upon mixing in water. 

They do not dissolve and they do not remain as individual molecules in solution, which 

reflects the difficulty with which the undissolved microemulsion is separated from true 

aqueous solution. The actual water solubility ofEOD substances is lower than reported. 

The log Kow value is estimated to be greater than 6.2 according to the OECD Guideline 

No. 117: HPLC Method. Estimated half-lives for the indirect photolysis in the 

atmosphere is (approximately) 1.9 hours. Abiotic hydrolysis is slow in part due to the low 

water solubility; the half-life ofESBO could not be determined. Level III Fugacity 

modeling, using loading rates for soil, and water of 1 000 kg/h and 0 kg/h for air (due to 

the very low vapor pressure of these materials), shows the primary distribution to 

sediment (69%) and soil (27%). Biodegradation studies with ESBO indicate that these 

materials are readily biodegradable (70% within 28 days, OECD 301F test). ESBO 

exhibited> 79% degradation over 28 days in the OECD 301B test. A previous study 

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showed a lesser extent of biodegradation (0% of ESBO after 20 days). The discrepancy in 

results between these biodegradation studies can be attributed to differences in inoculum 

density, and more importantly, the degree to which the insoluble test substance is 

dispersed in the aqueous test mixtures. Based on data ESBO is expected to be readily 

biodegradable. Whereas the estimated log Kow value of> 6.2 indicates a high potential 

for bioaccumulation, their uptake into fish is expected to be hindered by their large 

molecular size. If taken up by fish, these carboxylate ester-containing substances are 

expected to be readily metabolized and excreted. Thus, the bioaccumulation potential is 

expected to be much lower than predicted from log Kow alone." 

4) Other information 

The SIDS Initial Assessment Report is attached to this document. It concludes that no 

further work is recommended on Epoxidized Oils. The SIAR includes detailed data and 

references supporting the conclusion. 

CDR Petition for Certain Food-Use Substances 

40 C.F.R. § 711.15(b)(2)(ii)(C) Criterion Information 

(The information needs of EPA, other federal agencies, tribes, states, and local 

governments, as well as members of the public) 

Epoxidized soybean oil has not been the subject of or considered for information 

collection requirements by EPA under TSCA (other than the TSCA CDR), the Interagency 

Testing Committee (lTC), or the Agency for Toxic Substances and Disease Registry (ATSDR). 

Epoxidized soybean oil has not been or is not the subject of any proposed or final regulation by 

the EPA under the following programs: 

TSCA 4 Test Rules 

TSCA 4(F) Required Actions 

TSCA 5(A)(2) Chemicals Subject to Significant New Use Rules (SNURS) 

TSCA 5(B) Data Gathering Requirements 

TSCA 5(E) Testing Consent Order Chemicals 

TSCA 5(F) Immediately Effective Rules 

TSCA 6(A) Hazardous Chemical Control Rules 

TSCA 8(A) Toxic Substances Subject to Reporting Rules on Production 

TSCA 8(A) CAIR Comprehensive Assessment Information Rules 

TSCA 8(A) Pair Preliminary Assessment Information Rules 

TSCA 8(C) Records of Allegations of Significant Adverse Reactions 

TSCA 8(D) Health and Safety Reporting Rules 

TSCA 8(D) Health and Safety Reporting Rules Termination 

TSCA 12(B) Notices of Export 

SARA 313 Chemicals Regulated Under §313 of EPCRA 

See http:/ /www.epa. gov I opptintr/CO RR/index.htm. 

The petitioning association is not aware of any unmet information needs of the EPA, 

other federal agencies, tribes, states, local governments, or members of the public in light of: 

Page 5 
0 FDA regulatory clearances currently available for the petitioned substance which 

acknowledge that their use in food applications is safe; 

[ I The extensive data on the substance published on the ECHA website. See 

http:/ /apps.echa.europa.eu/registered/data/dossiers/0 IS S-9eba 7 e32-77 de-006ee044-00144f67d031/DISS-9eba7e32-77de-006e-e044-00144f67d031 DISS9eba7e32-77de-006e-e044-00144f67d03l.html 

The petitioning association would like the opportunity to respond and submit additional 

information needs identified by EPA during the petition process, if any, prior to EPA's final 

action on the petition request. 

CDR Petition for Certain Food-Use Substances 

40 C.F.R. § 711.15(b)(2)(ii)(D) Criterion Information 

(The availability of other complementary risk screening information) 

The following table provides the status ofthe petitioned substance on the Annex IV 

exemption determinations by the European Union for the REACH program; the REACH 

registration status; status under the voluntary EPA High Production Volume (HPV) Chemical 

Challenge Program; and safety determinations for low toxicity pesticide inerts. 

CAS Number Chemical Index Name EU REACH EUREACH HPV List Low Risk Inert Listing Exemption Registered 

8013-07-8 Epoxidized soybean oil No Yes 4 No 

The categorization for the 1990 and 1994 HPV lists is as follows: 

0 = Chemical is within the scope of the HPV Challenge Program and may be 

sponsored. 

1 = Chemical is not considered a candidate for testing under the HPV Challenge 

Program, based on preliminary EPA review indicating that testing using the SIDS 

base set would not further EPA's understanding of the chemical's properties. 

2 = Chemical is otherwise being handled under the Organization for Economic Cooperation and Development (OECD) Screening Information Data Set (SIDS) 

Program. 

3 = Chemical is not subject to the HPV Challenge Program because it is a polymer or 

inorganic substance. 

4 = A company or consortium has clearly indicated to and has had confirmed by the 

International Council of Chemical Associations (ICCA), its sponsorship of this 

chemical in the Global HPV Initiative of the ICCA, and all information 

essentially equivalent to a Full Commitment under the HPV Challenge Program 

(i.e., chemical name, CAS number, start year for each chemical, technical contact 

person and telephone number) has been provided to EPA. 

The key to EPA's Pesticide and Inert listings is as follows: 

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1 = Inert Ingredients of Toxicological Concern. 

2 = Potentially Toxic Inert Ingredients/High Priority for Testing Inerts. 

3 = Inerts ofUnknown Toxicity. 

4A = Minimal Risk Inert Ingredients. 

4B = Inerts which have sufficient data to substantiate they can be used safely in 

pesticide products. 

CDR Petition for Certain Food-Use Substances 

40 C.F.R. § 711.15(b)(2)(ii)(E) Criterion Information 

(The availability of comparable processing and use information) 

Processing and use of this substance are well characterized. TSCA-regulated exposures 

associated with this substance are comparable to, or less significant than, the food-use exposures 

associated with these substances which have already been shown to be "safe." More-specific 

processing and use information is included in the data summaries in the section of this petition 

that discusses (B) Criterion Information. 

CDR Petition for Certain Food-Use Substances 

40 C.F.R. § 711.15 (b)(2)(ii)(F) Criterion Information 

(Whether the potential risks of the chemical substance are adequately managed by 

EPA or another agency or authority) 

NOP A is not aware of any information to suggest that any agency is inadequately 

managing the safe use of Epoxidized soybean oil. 

The manufacturing and use of this substance primarily fall within the jurisdiction and 

authority ofthe FDA. However, the EPA, the Occupational Safety and Health Administration 

(OSHA), the National Institute for Occupational Safety and Health (NIOSH), and the Consumer 

Product Safety Commission (CPSC) regulate the manufacture and use of the petitioned substance 

as well. In addition, state environmental protection agencies have authority over facilities within 

their jurisdictions. 

As previously indicated, food uses of the petitioned components far exceed TSCAregulated uses. Activities related to TSCA-regulated processing and use of the petitioned 

substance will also result from food-processing activities. Indeed, the same production 

equipment, processing techniques, and feed stocks may be used. These activities and their 

resulting environmental effects are already controlled adequately under other regulatory regimes. 

With respect to EPA programs specifically, human and environmental exposures are adequately 

controlled through existing regulatory programs such as the Clean Water Act; the Clean Air Act; 

and the Resource Conservation and Recovery Act; and the Spill Prevention, Control and 

Countermeasures (SPCC) Program. Relevant FDA regulations for the petitioned substances are 

provided below. 

Petitioned Substance 

Epoxidized soybean oil 

CASRN 

8013-07-8 

Page 7 

FDA Regulation at 21 C.F .R. 

Sec. 172.723 (Direct food additive) 

Sec. 181.27 (Plasticizers) 
In addition, epoxidized soybean oil is approved as an inert in pesticides when used preand post-harvest and is exempt from the requirements of a tolerance. See 40 C.P.R. Sec. 

180.910. See also 40 C.P.R. 180.930 (Inert ingredients applied to animals exemptions from the 

requirement of a tolerance.) 

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