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### KELLER AND HECKMAN LLP ServingBusiness through Law andScience®
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April4, 2014 

### Via E-mail and Certified Mail
OPPT CDR Submission Coordinator Mailcode 7407M Attn: Inventory Update Reporting and Chemical DataReporting Office ofChemical Safety and Pollution Prevention Environmental ProtectionAgency 1200 PennsylvaniaAve., NW. Washington, DC 20460 Writer's DirectAccess Herbert Estreicher, J.D., Ph.D. (202) 434-4334 estreicher@khlaw. com



### Re: Request ForExemption OfEpoxidized Soybean Oil From TSCA ChemicalDataReporting (CDR) ProcessingAnd Use Information ReportingRequirements In2016
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 ofthe reporting form, Form U) pursuantto 40 C.F.R. 711.15(b)(2)(iii). ESBO is oflowriskto humanhealth and the environment. I. 

### BASIS FORPETITION
EPA regulations at 40 C.F.R. § 711.15(b)(2)(iii) permit any personto requestthat the EPA amend the list ofsubstances 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 ofwhetherthis 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 ofthe six exemption considerations for ESBO. Most importantly, ourpetition demonstrates that there is "low current interest" in CDRprocessing and use data for this productbecause it is oflowpotential 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 Page 2

particularthe U.S. Food and Drug Administration; has a long history ofsafe 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 confidentthat the EPA will conclude that this substance should be added to the list ofCDRpartially exempt substances.


### II. TSCA REGULATED USES According to the SIDS Initial Assessment Report (SIAR), ESBO is approved for use as an inert ingredient inpesticides; the product is used as an acid scavengerto protectthe application equipment from corrosion, rather than as an active ingredient inthe pesticide. Itis also used as a plasticizer in PVC for a wide range ofapplications including food-contact materials and has approvals under EU and FDA regulations.
Eventhough the subjectrequest is to partially exempt ESBO for the 2016 CDRreporting cycle, NOPA requests that the EPA provide its response to this petition within the 120 days contemplatedunder 40 C.P.R. 711.15(b)(2)(iii)(A). 

## * * * Sincerely yours,



# ~~

Herbert Estreicher, Esq.
Enclosures

### CDRJ>etition for Certain Food-Use Substances 40 C.F.R. §711.415(b)(2)(ii)(A) CriterionInformation (Whetherthe chemical qualifies orhas qualified inpastIURcollections 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 whetherthe substance meets the criteriaof "whether the chemical qualifies or has qualified inpast IURcollections for the reporting of information described in §711.15(b)(4)." See 40 C.P.R.§ 711.15(b)(2)(ii)(A). Itwas reported in the 2006 IUR and the 2012 CDR. Processing and use data were providedby 18 companies in the 2012 CDR. The 2012 CDR volume wasreported as 148,763,647lbs.peryear. Datareported to EPA on a confidential basis for purposes ofIURor CDR are not necessarily reflected in this submission. The Agency is respectfully requested to reviewthe IUR orCDRdatabase for confidential data to supplement the dataprovided. 

### CDRPetition for CertainFood-Use Substances 40 C.F.R. § 711.415(b)(2)(ii)(B) CriterionInformation (The chemical substance's chemical and physical properties orpotentialfor persistence, bioaccumulation,health effects, orenvironmental effects (considered independently ortogether))
Extensive datawere developed by EPAfor ESBO in the OECD SIDS Initial Assessment Report for the Epoxidized Oils and Derivatives (EOD) Category, which is provided as an attachmentto this document. The following provides a summary ofthe datafrom this report.


### DataAvailable onEpoxidized Soybean Oil (ESBO) (CASRN 8013-07-8) from the OECD SIAR 1) Substanceidentity profile

a. Substance identifiers

CAS name: Epoxidized soybean oil (ESBO) Othernames: Epoxidized soy oils Epoxidized soya oils Fatty acid, soybean oil, epoxidized Soybeanoil, epoxidized CASRN: 8013-07-8

Page 1Molecular structure: Soybean oil, the natural productfrom which ESBO is derived, is a triglyceride, with a typical fatty acid distribution oflinoleic (49-57%), oleic (26-36%), and linolenic (1-2%) acids constitutingthe major unsaturated fatty acid components. Saturated fatty acid components constitute about 14% ofthe mixture. Epoxidation at most or all ofthe points ofunsaturation (double bonds between carbon atoms) in the fatty acid chains gives a variety of products collectively known as epoxidized soybean oil. The alcohol portion ofthis 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 whichESBO is derived, is a triglyceride, with a typical fatty acid distribution oflinoleic (49-57%), oleic (26-36%), and linolenic (1-2%) acids constituting the majorunsaturated fatty acid components. Saturated fatty acid components constitute about 14% ofthe mixture. Epoxidation at most or all ofthe points ofunsaturation (double bonds between carbon atoms) inthe fatty acid chains gives a variety ofproducts collectivelyknown as epoxidized soy bean oil. ESBO maybe producedby oxidation ofsoybean oil withhydrogen 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 scavengerto protectthe application equipment from corrosion, rather than as an active ingredient inthe pesticide. Itis also used as aplasticizer in PVC for a wide range ofapplications. FDAregulates ESBO as a direct additive for use in brominated soybean oil and as an indirect additive for a variety ofuses 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 expectedto be absorbed and metabolized, resulting in the release offree epoxidized fatty acids and lesser substituted alcohols or glycerides. Lipase is an enzyme that assists in the breakdown and digestion offat in the body. Pancreatic lipase works atthe oil/waterinterface, because triglycerides are insoluble. During metabolism inthe 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. Otherproducts ofmetabolism 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 shownto hydrolyze propylene glycol monoesters and diesters in vitro. The absorption, metabolism and hydrolysis of propylene glycol distearate were studied inrats using isotopically labelled compounds. These processes for the propylene glycol esters were found to be similarto those ofthe glycerol esters. So, there is evidence that the propylene glycol esters offatty 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 inrabbits 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; howeverthe 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 inrats fed ESBO at 1% or 5% in diet. Gross findings indicated a test article-related effect ofESBO 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 ofthree 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% ofthe diet. Further, the
Page 3NOAEL was 2.5%, providing an average daily intake ofapproximately 1.0 g/kg bwin males and 1.4 g/kg bwin females. There were no treatment-related histopathologic lesions and there was no evidence ofcarcinogenicity ofESBO in groups ofmale and female rats given ESBO inthe 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:
"Acutetoxicity 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 shortertime periods than currently specified in the OECD guidelines, for the time periods examinedthere was no orminimal evidence oftoxicity observed at the limit ofwater solubility. In the algae study with ESBO, onthe basis ofbiomass, the median effective concentration was 72 h EbC50 > 8 mg/L and 72 h NOEC = 2.3 mg/L. Effects are not expectedto be observed belowthe water solubility of these materials. Based onthe physicochemical properties ofESBO (very lowwater solubility, log Kow values > 6.2, and readily biodegradable), it is unlikely to be bioavailable to aquatic organisms." 

### 3) Environmental Fate
Data from the SIARon environmental fate are as follows:
"The melting point ofis 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. Itis the nature ofthe epoxidized oils to form an emulsionuponmixing in water. They do not dissolve and they do notremain as individual molecules in solution, which reflects the difficulty with whichthe undissolved microemulsion is separated from true aqueous solution. The actual water solubility ofEOD substances is lowerthanreported. The log Kow value is estimated to be greater than 6.2 according to the OECD Guideline No. 117: HPLC Method. Estimatedhalf-lives for the indirectphotolysis 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 notbe 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 lowvaporpressure ofthese materials), shows the primary distributionto sediment (69%) and soil (27%). Biodegradation studies with ESBO indicatethat these materials are readily biodegradable (70% within 28 days, OECD 301F test). ESBO exhibited> 79% degradation over28 days in the OECD 301B test. A previous study

Page4showed a lesser extent ofbiodegradation (0% ofESBO after 20 days). The discrepancy in results betweenthese biodegradation studies canbe attributed to differences in inoculum density, and more importantly, the degree to which the insoluble test substance is dispersed inthe 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 hinderedby their large molecular size. Iftaken up by fish, these carboxylate ester-containing substances are expectedto be readily metabolized and excreted. Thus, the bioaccumulationpotential is expectedto be much lowerthan predicted from log Kow alone." 

### 4) Otherinformation
The SIDS Initial Assessment Report is attached to this document. Itconcludes that no further work is recommended on Epoxidized Oils. The SIARincludes detailed data and references supporting the conclusion.


### CDRPetition for Certain Food-Use Substances 40 C.F.R. 

### § 711.15(b)(2)(ii)(C) CriterionInformation (The information needs ofEPA, otherfederal agencies, tribes, states, and local governments, as well as members ofthe public) Epoxidized soybean oil has not been the subject ofor considered for information collection requirements by EPAunder TSCA (other than the TSCA CDR), the Interagency Testing Committee (lTC), orthe Agency for Toxic Substances and Disease Registry (ATSDR). Epoxidized soybean oil has not been or is not the subject ofany proposed or final regulation by the EPAunderthe following programs: TSCA 4 Test Rules TSCA 4(F) Required Actions TSCA 5(A)(2) Chemicals Subjectto SignificantNewUse 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 Subjectto Reporting Rules on Production TSCA 8(A) CAIR Comprehensive Assessment Information Rules TSCA 8(A) Pair Preliminary Assessment Information Rules TSCA 8(C) Records ofAllegations ofSignificantAdverse Reactions TSCA 8(D) Health and Safety Reporting Rules TSCA 8(D) Health and Safety Reporting Rules Termination TSCA 12(B) Notices ofExport SARA 313 Chemicals Regulated Under §313 ofEPCRA See http://www.epa.gov

### I opptintr/CORR/index.htm. The petitioning association is not aware ofany unmet information needs ofthe EPA, other federal agencies, tribes, states, local governments, or members ofthe public in light of:

Page 50 FDA regulatory clearances currently available for the petitioned substance which acknowledge that their use in food applications is safe; [ I The extensive data onthe substance published onthe ECHA website. See http:/ /apps.echa.europa.eu/registered/data/dossiers/0ISS-9eba 7e32-77de-006ee044-00144f67d031/DISS-9eba7e32-77de-006e-e044-00144f67d031 DISS9eba7e32-77de-006e-e044-00144f67d03l.html
The petitioning association would like the opportunityto respond and submit additional informationneeds identified by EPA during thepetitionprocess, ifany, prior to EPA's final action onthe petition request. CDR Petition for Certain Food-Use Substances 40 C.F.R. § 711.15(b)(2)(ii)(D) Criterion Information (The availability ofother complementary risk screening information) The following table provides the status ofthepetitioned substance onthe Annex IV exemption determinations by the European Union for the REACHprogram; 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 InertListing 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 withinthe scope ofthe HPV Challenge Program and maybe sponsored. 1 = Chemical is not considered a candidate for testing underthe HPV Challenge Program, based onpreliminary EPA review indicating that testing using the SIDS base set would not further EPA'sunderstanding ofthe 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 subjectto the HPV Challenge Programbecause it is a polymer or inorganic substance. 4 = A company or consortium has clearly indicated to and has had confirmed bythe International Council ofChemical Associations (ICCA), its sponsorship ofthis chemical in the Global HPV Initiative ofthe ICCA, and all information essentially equivalent to a Full Commitmentunderthe HPV Challenge Program (i.e., chemical name, CAS number, start year for each chemical, technical contact person and telephone number) has beenprovided to EPA. Thekey to EPA's Pesticide and Inert listings is as follows:
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### = Inert Ingredients ofToxicological Concern. 2 = Potentially Toxic Inert Ingredients/High Priority for Testing Inerts. 3 = Inerts ofUnknownToxicity. 4A

### = Minimal Risk Inert Ingredients. 4B 

### = Inerts which have sufficient datato substantiate they canbe used safely in pesticide products.
CDRPetition for Certain Food-Use Substances 40 C.F.R. § 711.15(b)(2)(ii)(E) Criterion Information (The availability ofcomparable processing and use information) Processing and use ofthis substance are well characterized. TSCA-regulated exposures associated with this substance are comparable to, or less significantthan, the food-use exposures associated with these substances which have already been shownto be "safe." More-specific processing and use information is included in the data summaries in the section ofthis petition that discusses (B) Criterion Information. CDRPetition for Certain Food-Use Substances 40 C.F.R. § 711.15 (b)(2)(ii)(F) Criterion Information (Whether the potential risks ofthe chemical substance are adequately managed by EPA or another agency or authority)
NOPA is not aware ofany information to suggest that any agency is inadequately managing the safe use ofEpoxidized soybean oil.
The manufacturing and use ofthis substance primarily fall within thejurisdiction 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 ofthe petitioned substance as well. In addition, state environmental protection agencies have authority over facilities within theirjurisdictions.
As previously indicated, food uses ofthe petitioned components far exceed TSCAregulated uses. Activities related to TSCA-regulatedprocessing anduse ofthe 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 EPAprograms 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; andthe Spill Prevention, Control and Countermeasures (SPCC) Program. Relevant FDAregulations for the petitioned substances are providedbelow.

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 inpesticides when usedpreand post-harvest and is exempt from the requirements ofa tolerance. See 40 C.P.R. Sec. 180.910. See also 40 C.P.R. 180.930 (Inert ingredients appliedto animals exemptions from the requirement ofa tolerance.)

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