CBIC Control Number 

362737 

R.ECEIVED 

GREENWICH CHEMICAL CoNSULTING, QfJ~-f=881C 

November 21, 2014 

By Federal Express 

33oo PGA BouLEvARD. surTE 635 ZOI'-I·lov 24 A1,

111 : 1 1 PALM BEACH GARDENS, FL 33410 ~ . ~ 

TELEPHONE 561.578.8110 

FACSIMILE 561.578.8120 

CONTAINS NO CONFIDENTIAL 

BUSINESS INFORMATION 

OPPT Document Control Office 

U.S. Environmental Protection Agency 

EPA East Building 

RoomE6428 

1201 Constitution Ave., 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 of Certain High 

Production Volume Chemicals: Second Group 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 a 
U.S. Environmental Protection Agency 

November 21,2014 

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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 of a 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 and importers of these HPV chemicals, including sodium erythorbate, 

to conduct testing to obtain screening level data for human health effects, environmental 

effects, chemical fate, and physical/ chemical properties. 

The Agency has issued dlis test rule under its TSCA Section 4(a)(1)(B) aud1ority based on its 

determination that HPV compounds, including sodium erythorbate, are "produced in 

substantial quantities; there is or may be substantial human exposure to them; 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/Water Partition Coefficient [40 CFR 799.6755, ASThi E 1147-92, or 40 

CFR 799.6756] 

• Ready Biodegradation' 

• Aquatic Toxicity Testing4: 

Acute toxicity to fish [ASTM E 729-96] 

Acute toxicity to Daph11ia [ASTM E 729-96] 

Toxicity to plants (algae) [ASTM E 1218-04d] 

Harlan Laboratories Ltd. (Harlan Laboratories) was selected to conduct all of these tests. Also, 

Greenwich Chemical Consulting is se1ving as the study monitor for this testing. 

I Januaty 7, 2011; 76 Fed. Reg. 1067. 2 I d. 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. Environmental Protection Agency 

November 21,2014 

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II. Significant Technical Issue during Method Development Work Ahead 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 of these efforts were successful. 

A conference call between the laboratory and Greenwich Chemical Consulting was 

subsequently held to discuss this issue. During the call tl1e laboratory indeed confirmed that it 

was not possible to sufficiently stabilize the test item in water to enable the quantitative analysis 

to be performed during ilie planned ecotoxicity testing. Moreover, Harlan Laboratory had no 

suggestions on how to stabilize the material in water despite its significant experience io 

conducting ecotoxicity testing. 

Therefore, tlrrough iliis letter, we are requesting technical guidance from ilie Agency on how 

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 required under ilie TSCA Section 4 test rule. This is because 

iliere is no practical reason or scientific justification for measuriog the ecotoxicity of a 

substance iliat inttnediately hydrolyzes in water. 

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 

request beyond ilie Pebruary 11,2015 deadline will be needed. Under iliis scenario, Greenwich 

Chemical Consulting will submit such an extension request to EPA on behalf of Univar. 
U.S. Environmental Protection Agency 

November 21,2014 

Page 4 

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CONTAINS NO CONFIDENTIAL 

BUSINESS INFORMATION 

Univar thanks the Agency for its consideration in this matter. For all questions, comments, 

and determinations concerning this matter, please use the contact information given below. 

Mr. John V. Massingale 

Greenwich Chemical Consulting, Inc. 

3300 PGA Boulevard, Suite 635 

Palm Beach Gardens, FL 33410 

Telephone: (561) 578-8110 

Facsimile: (561) 578-8120 

E-mail: john@grcci.com 

Sincerely, 

John V. Massingale 

Principal 

cc: Ms. K. Gilje- Univar 

Ms. S. Lilley- Univar 

Mr. ]. Schaeffer - EPA 
Study Number: 41401176 

Summary of method development for d-erythro-llex-2-enoic acid, gamma lactone, monosodium 

salt. 

+ Na 

HO ~~oyo _ )=( 

HO OH 

Figure 1: Chemical structure of the test item 

It was suspected that given the structure of the test item that it was likely to undergo rapid hydrolysis 

when exposed to aqueous media. 

The test item was initial dissolved in RO water and il\iected on a Cl8 column looking at 245 nm. It 

was run isocratic at 50/50 0.1% formic acid in RO/MeCN. The peak was not retained, a gradient 

starting at 95% aqueous to I 00% organic and the peak was still not retained. Other columns were 

tested however no retention was possible. 

The test item solution was scanned in positive mode on a mass spectrometer and a response at 199 

mlz was seen, this correlates to the sodium adduct of the test item. After 24 hours another scan was 

carried out ofthe test item solution and the 199 ion was not seen, a fi·esh standard was prepared and 

the 199 ion could be seen. No other ions were seen in the old standard that were not present in blank 

spectrum. 

A UV scan between 200 to 400 nm was carried out on both the fresh and the old standard. A large 

response was seen at 245 run for the fresh standard however the response 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 in Methanol, standards were prepare in at 100 and I 0 mg/L. 

These were then analysed by LC-UV and after~ 3 hours the response for the 100 mg/L standard was 

approximately 40% ofthe original response, after the same period of time the I 0 mg/L standard was 

undetectable. 

This implies that the test item is not stable in MeOH. Other solvents were tested to see if it was 

possible to obtain a solution which was stable. It was seen that the test item was insoluble in 

Acetonitrile, THF, Hexane, MTBE and DCM. 

As it was 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 UV response dropped by approximately I 1% 

over 2. 75 hours. This is still not acceptable for a reproducible analysis. A further attempt was made by 

the addition of phosphoric acid (3%). A 100 mg/L standard was prepared in this phosphoric acid 

solution, this was then analysed by LC-UV, the response dropped by II% over 90 minutes and was 

approximately 52% of the original response after 4 hours. Therefore the test item is not stable in an 

acidic solution. 

Due to the fact that no way of stabilising the test item in solution could be found and that no response 

either by mass spectromehy or UV detection could be identified for a degradation product it is not 

possible to analyse for the presence of this test item in the ecotoxicology analysis samples.