CBIC Control Number 

# 362737 R.ECEIVED GREENWICH CHEMICAL CoNSULTING,

### QfJ~-f=881C

November 21, 2014

By FederalExpress 33oo PGA BouLEvARD. surTE 635 

## ZOI'-I·lov 24 A 1 , 111 : 11 PALM BEACH GARDENS, 

### FL 33410**~** .**~** TELEPHONE 561.578.8110 FACSIMILE 561.578.8120

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OPPTDocumentControl Office U.S. EnvironmentalProtectionAgency EPA EastBuilding RoomE6428 1201 ConstitutionAve., NW Washington, DC 20004 Attn.: TSCA Section 4

Re: Significant Technical Issue Encountered with Testing Conducted by Univar USA under the TSCA Section 4 Test Rule on the 

### Testing ofCertain High Production Volume Chemicals: SecondGroup of Chemicals D-erythro-Hex-2-enonic acid, .gamma.-lactone, monosodium salt CAS RN 6381-77-7 

### (Sodium erythorbate) Docket Identification No. EPA-HQ-OPPT-2007-0531; 40 CFR 799.5087 Dear Sir/Madam: On behalf of its client, Univar USA Inc. (Univar or the Company), Greenwich Chemical Consulting, Inc. (Greenwich Chemical Consulting) submits to the U.S. Environmental Protection Agency (EPA or the Agency) information on a significant technical issue encountered during testing conducted on the chemical substance, D-erythro-hex-2-enonic acid, .gamma.-lactone, monosodium salt [CAS RN 6381-77-7] which is currently subject to aU.S. Environmental Protection Agency November 21,2014 Page 2 CONTAINS NO CONFIDENTIAL BUSINESS INFORMATION

Toxic Substances Control Act (TSCA) Section 4 test rule. 1 Specifically, as part of the laboratoty's method development work ahead of the required ecotoxicity testing, it was determined that the test material undergoes rapid hydrolysis when placed in water. The material was found to be unstable in water and hydrolysis occurs in a matter ofa few hours. Through this letter, Univar requests technical guidance from EPA on how to proceed with this testing. I. General Background As a matter of background, this test rule addresses 19 high production volume (HPV) chemicals that went unsponsored under the Agency's voluntaty HPV Chemical Challenge Program. One of the 19 chemicals identified in the rule is D-etythro-hex-2-enonic acid, .gamma.-lactone, monosodium salt which is identified herein as 

### sodi11111 erythorbate. The rule requires manufacturers andimporters ofthese HPV chemicals, including sodium erythorbate, to conduct testing to obtain screening level data for human health effects, environmental effects, chemical fate, andphysical/chemical properties. TheAgency has issued dlis test rule underits TSCA Section 4(a)(1)(B) aud1ority based on its determination that HPV compounds, including sodium erythorbate, are "produced in substantial quantities; there is ormaybe substantialhuman exposure tothem; existing data are insufficient to determine or predict their health and environmental effects; and testing is necessaty to develop such data."2 The final rule identifies the following studies and test protocols on sodium etythorbate:

• n-Octanol/WaterPartition Coefficient [40 CFR 799.6755, ASThi E 1147-92, or 40 CFR 799.6756] • Ready Biodegradation' • AquaticToxicityTesting4: Acute toxicity to fish [ASTM E 729-96] Acute toxicity to 

### Daph11ia [ASTM E 729-96] Toxicity to plants (algae) [ASTM E 1218-04d] HarlanLaboratoriesLtd. (HarlanLaboratories) was selected to conduct all ofthese tests. Also, Greenwich Chemical Consultingis se1ving as the study monitor for this testing.

I Januaty 7, 2011; 76 Fed. Reg. 1067. 2Id. at 1069. 3 The test rule identifies six ISO protocols and one ASTivi standard for biodegradation testing. The protocol selection depends on the test substance's physical and chemical properties. 4 Because the n-octanol/water partition coefficient is expected to be significantly less than 4.2 based on the compound's high water solubility, Test Group 1 is expected to apply.U.S. EnvironmentalProtectionAgency November 21,2014 Page 3 CONTAINSNO CONFIDENTIAL BUSINESS INFORMATION

II. Significant Technical Issue during Method DevelopmentWorkAhead ofEcotoxicity Testing Harlan Laboratories recently advised Greenwich Chemical Consulting that in the method development work preceding ecotoxicity testing, it was determined that the sodium erythorbate rapidly hydrolyzes in water. Specifically, the laboratory reports that a 100 mg/I. aqueous solution undergoes 60% hydrolysis within tlttee (3) hours. In addition, a 10 mg/L aqueous solution undergoes 100% hydrolysis within this same time period. See attached ftle containing the report from Harlan Laboratories describing tl1is technical issue. As discussed in the report, the laboratory undertook additional efforts to stabilize the material in water. However, none ofthese efforts were successful. A conference call between the laboratory and Greenwich Chemical Consulting was subsequentlyheld to discuss this issue. Duringthe call tl1e laboratory indeedconfirmed thatit was notpossibleto sufficientlystabilize thetestiteminwatertoenable thequantitative analysis to be performed during ilie planned ecotoxicity testing. Moreover, Harlan Laboratoryhad no suggestions on how to stabilize the material in water despite its significant experience io conductingecotoxicity testing. Therefore, tlrrough iliis letter, we are requesting technical guidance from ilie Agency onhow to proceed on iliis matter. In tl1e absence of EPA being able to provide such technical guidance. Univar requests iliat EPA give every consideration to eliminating the iliree (3) ecotoxicity studies from the tests requiredunder ilie TSCA Section 4 testrule. Thisis because iliere is no practical reason or scientific justification for measuriog the ecotoxicity of a substance iliat inttnediately hydrolyzes inwater. III. Likely Extension Request Based on ilie significant technical issue described above and in ilie case where this issue can be resolved and ilie three (3) ecotoxicity tests performed, it is highly likely iliat an extension requestbeyondiliePebruary 11,2015 deadlinewill beneeded. Underiliis scenario, Greenwich Chemical Consultingwill submit such an extensionrequest to EPA onbehalfofUnivar.U.S. Environmental Protection Agency November 21,2014 Page 4 

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### Univar thanks the Agency for its consideration in this matter. For all questions, comments, and determinations concerning this matter, please use the contactinformation given below. Mr. John V. Massingale Greenwich Chemical Consulting, Inc. 3300 PGA Boulevard, Suite 635 PalmBeach Gardens, FL 33410 Telephone: (561) 578-8110 Facsimile: (561) 578-8120 E-mail: john@grcci.com Sincerely,

JohnV. Massingale Principal

cc: Ms. K. 

### Gilje- Univar Ms. S. Lilley- Univar Mr. ]. Schaeffer

- EPAStudy Number: 41401176 Summary ofmethod development for d-erythro-llex-2-enoic acid, gamma lactone, monosodium salt.

+ Na

# ~~oyo HO

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HO OH Figure 1: Chemical structure ofthe test item Itwas suspectedthat given the structure ofthe test item that it was likely to undergo rapid hydrolysis when exposedto aqueous media. Thetest item was initial dissolved in RO water andil\iected on a Cl8 column looking at 245 nm. It was run isocratic at 50/50 0.1% formic acid in RO/MeCN. Thepeak was notretained, a gradient starting at 95% aqueous to I00% organic andthe peak was still notretained. Other columns were tested however no retention was possible. The test item solution was scanned in positive mode on amass spectrometer and aresponse at 199 mlz was seen, this correlates to the sodium adduct ofthe test item. After 24 hours another scan was carried out ofthetest item solution and the 199 ion was not seen, a fi·esh standardwas prepared and the 199 ion couldbe seen. No other ions were seen in the old standard thatwere not present in blank spectrum. A UV scanbetween 200 to 400 nm was carried out onboth the fresh and the old standard. A large response was seen at 245 run for the fresh standard howevertheresponse had significant decreased in the old standard. This data COJTelates with the idea that the test item is rapidly hydrolysing and the standard solution is not stable. The test item was found to be soluble inMethanol, standards were prepare in at 100 and I0 mg/L. These were then analysed by LC-UV and**after~** 3 hours the response for the 100 mg/L standard was approximately 40% oftheoriginal response, afterthe same period oftime the I0 mg/L standard was undetectable. This implies that the test item is not stable in MeOH. Other solvents were tested to see ifitwas possible to obtain a solution which was stable. It was seen thatthetest item was insoluble in Acetonitrile, THF, Hexane, MTBE and DCM. As itwas insoluble in other solvents, an attempt was made to stabilise the test item in a water solution by acidifying to the solution with 5% acetic acid, the UVresponse dropped by approximately I 1% over 2.75 hours. This is still not acceptable for areproducible analysis. A further attempt was made by the addition ofphosphoric acid (3%). A 100 mg/L standard was prepared in this phosphoric acid solution, this was then analysed byLC-UV, the response droppedby II% over 90 minutes and was approximately 52% ofthe original response after 4 hours. Therefore the test item is not stable in an acidic solution. Dueto the fact that no way ofstabilisingthe test item in solution could be found and thatnoresponse eitherbymass spectromehy or UV detection could be identified for a degradation product itis not possible to analyse for the presence ofthis test item in the ecotoxicology analysis samples.