# pppppp~

December 21, 2012 

# Mk4.35M7 RECEIVED EASTMAN OPPT CBIC Eastman Chemical Company 

## 1012 DEC 26 A1110:09 P. 0 . Box 511 Kingsport, Tennessee 37662 Telephone: 423-229-2094 www .Eastman.com



### Document Control Office (DCO) (7407M) Office ofPollution Prevention and Toxics (OPPT) Environmental Protection Agency 

### 1200 Pennsylvania Ave., N .W . Washington, DC 20460-0001 Attn: TSCA Section 4

. IIIIII IIIII IIIIhIIIIIIIIII IIIII IIIII IIIII IIIII IIIIIIIIII IIII IIII

RE: Docket ID Number EPA-HQ-OPPT-2009-0112. Testing update for propanoic acid, 2-methyl-, 3-(benzoyloxy)-2,2,4-trimethylpentyl ester (CASRN 22527-63-5) pursuant to 40 CFR 799.5089 and request for modification pursuant to 40 CFR 790 .55 . Dear Sir or Madam, Eastman Chemical Company ("Eastman") previously submitted a test plan ("Plan") in February of this year (Attachment) for propanoic acid, 2-methyl-, 3-(benzoyloxy)-2,2,4-trimethylpentyl ester (CASRN 22527-63-5) pursuant to the test rule published on October 21, 2011 (76 Fed. Reg. 65,385; 40 CFR 799.5089) .t In accordance with the requirements of 40 CFR 790.55 on the modification oftest standards or schedules during conduct of test, Eastman is requesting a modification of the schedule and providing a status update for the testing. As indicated in the table below, certain tests identified in the Plan are still underway or have been delayed. As a result, Eastman formally requests the agency to modify the schedule for completion of the planned testing to extend the deadline for all testing to the end of 2013. Pursuant to the test rule, Eastman submitted a letter of intent to test in December 2011 and its proposed test plan on February 20, 2012. Further discussions between Eastman and the agency were required to determine a suitable purity and composition for the test article. The agency affirmed the Plan and test article on April 19, 2012 and testing was initiated with Harlan Laboratories Ltd, UK (Harlan Labs) soon after . At some point during the current test period Harlan Labs' capacity to conduct the studies as originally planned became limited and certain tests under the Plan were delayed. Harlan Labs attributed these delays to increased testing demands fromREACHregistrants and an administrative error in the management of certain Eastman testsZ (letter on file) . While Eastman has been aware that the OECD 422 Combined Repeated Dose Study test could not begin until

~ The Test Plan was inadvertently dated 20 February 2011 . The correct date for the Test Plan is 20 February 2012. ~ The administrative error delayed the start of the chronic aquatic toxicity studies and the ready biodegradation study.



# - JAN 1 5 2012 CONTAINS NOCBIp. 2 

# EASTMAN early 2013 and that a request to the agency for modification of the testing schedule would be needed, the delays related to the remaining tests under the Plan had not been clearly communicated to Eastman until recently. It is also important to recognize that a portion ofthe test period set forth under the rule was used to finalize the Plan and purity of the test article. Even as the sole sponsor of the testing, Eastman was optimistic the testing could be substantially completed with the balance of the testing period, approximately seven (7) months. As shown by the table below, many of the studies have been completed or are currently in progress. Several studies, however, are nownot expected to begin until early in 2013. Most notably, it does not appear that the OECD 422 study can begin until the second quarter of 2013 pending completion of a preliminary range finding study. Completion of this study and a final report is expected to take six (6) months. All other tests should be completed with reports provided to the agency by the end of March 2013. As a result of these events, Eastman requests the agency to modify the test rule to provide an extension of the test period through the end of 2013. The status of each test in the Plan is described below . During the test period Eastman has completed several tests and is waiting to receive the final draft reports. As the final test reports are completed, Eastman will expeditiously provide the reports to the agency. As noted above, Eastman anticipates that all of the tests except the OECD422 will be completed and submitted to the Agency by the end of March 2013.

r, . Required Test ; Current Status Physical/Chemical Prop erties A1 Freezing Point. Expected com pletion in March, 2013 A2 Boiling Point. Expected com pletion in March, 2013 A3 Vap

or Pressure. Expected com pletion in March, 2013 A4 n-Octanol/Water Partition Coefficient (log,o or log K . .) Completed . Log KoW

indicates chronic aquatic toxicity testing required. A5 Water Solubility. Expected com pletion in March, 2013 Environmental Fate-Read Biode radation B Read Biode adation Expected com pletion in March, 2013 A quatic Toxicity Cl Chronic Toxicity to Daphnia Expected com pletion in March, 2013 Mammalian Toxicity-Acute D Up and Down Procedure Completed. Afinal draft report is expected in January, 2013. Mammalian Toxicity -Genotoxicit El Bacterial Reverse Mutation Completed. Afinal draft report is expected in January, 2013. E2 In vitro Mammalian Chromosomal Aberration Study in progress. A draft report is expected in February, 2013. Mammalian Toxicity-Repeated Dose/Re roduction/Develo mental Fl Combined repeated dose toxicity study with the reproduction/developmental toxicity screening An initial dose range finding study was completed. The results were inconclusive and require a new study to be performed

. Eastman currently expects this to be repeated in February, 2013 andfollowed by a definitive OECD 422 stud beginning in the second quarter of 2013. Pursuant to the requirements of40 CFR 790.55(a), Eastman respectfully requests the Agency extend the testing schedule under the Plan through the end of 2013. If you should havep. 3 

# EASTMAN

Sincerely, 

# Lodu .0~

Leonard Velsor Senior Attomey 

### Eastman Chemical Company P.O. Box 511 Building 75 Kingsport,TN 37662-5075

# ATTACHMENT



# Test plan for propanoic acid, 2-methyl-, 3-(benzoyloxy)- 2,2,4-trimethyl pentyl ester (CASRN 22527-63-5) pursuant

to 40 CFR 799.5089.

CONTAINS NOCBI

### 20 February 2011

Document Control Office (DCO) (7407M) Office of Pollution Prevention and Toxics (OPPT) Environmental Protection Agency 

### 1200 Pennsylvania Ave., N .W . Washington, DC20460-0001 Attn: 40 CFR799.5089; Docket IDNumber EPA-HQ-OPPT-2009-0112. p. 5 

# EASTMAN Eastman Chemical Company

P . O . Box 511 Kingsport,Tennessee 37662 Telephone: 423-229-2094 www .Eastman .com



### RE: Test Plan for propanoic acid, 2-methyl-, 3-(benzoyloxy)-2,2,4-trimethylpentyl ester (CAS-No. 22527-63-5) pursuant to 40 CFR799.5089. Dear Sir or Madam, Eastman Chemical Company (Eastman) currently manufacturers propanoic acid, 2-methyl-, 3- (benzoyloxy)-2,2,4-trimethylpentyl ester (CAS-No

. 22527-63-5) which is subject to the October 21, 2011 test rule (Test Rule) through the Environmental Protection Agency's (EPA or Agency) High Production Volume (HPV) Challenge Program .' This letter follows up Eastman's December 20, 2011 Letter of Intent and outlines a proposed testing plan fully intended to fulfill the requirements of the Test Rule. In August 2010, Eastman acquired Genovique Specialties Corporation which manufactured propanoic acid, 2-methyl-, 3-(benzoyloxy)-2,2,4-trimethylpentyl ester (benzoate ester) for products it sold commercially. Prior to the acquisition, Eastman had not manufactured this substance and had no need to sponsor testing of this substance through the HPV programor respond to the proposed rule.2 Following publication of the Test Rule, Eastman reached out to other potential manufacturers identified through various resources including companies that preregistered the substance under the European Union's REACHregulation. Eastman has preregistered this substance through REACH and plans to submit its registration by the applicable deadline. Despite our efforts, Eastman was unable to identify other companies with a need to participate in testing at this time .

~ 76 FR 65385; 40CFR 799.5089 Z 75 FR 8575 (February 25, 2010) 

### Page 1 of 5p. 6 

## EASTMAN Eastman has carefully reviewed the requirements set forth in the Test Rule and related information and intends to carry out the required testing. Where necessary, however, Eastman has proposed modification of the testing requirements . Test Article Puritv Since submitting the Letter of Intent, Eastman has determined that the benzoate ester as currently manufactured is not manufactured as an isolated substance but rather as the major component in a bulk reaction. This material is then formulated into products that are sold commercially. Under the Test rule, EPA identifies two forms of test substances for testing: Class 1 or Class 23 A Class 1 chemical substance is a substance having a composition consisting of a single chemical species, excluding impurities, which can be represented by a specific chemical structure. As provided in Table 2 of 40 CFR 799.5089(), benzoate ester is deemed a Class 1 chemical substance and testing must be conducted with material having a purity of 99% or greater, unless otherwise specified.4 In circumstances where the sponsor believes that a 99% level of purity is unattainable for a given chemical substance, the Test Rule directs the sponsor to request a modification under 40 CFR 790.55.5 The current manufacturing process for benzoate ester yields a maximum concentration approaching 70%

of the test substance. Based on discussions with our technical personnel, achieving material ofa purity sufficient to satisfy the requirements for the existing Test Rule (i .e., 99%or greater) will require a very intensive distillation process and there is uncertainty that the sufficient purity and adequate test quantity amounts can be achieved in a timely manner to comply with the Test Rule. Pursuant to the requirements of 40 CFR 790.55(a), Eastman requests the Agency to permit a modification of the requirements under the Test Rule to allow for testing to be conducted with a test article ofthe following purity profile: 

### 60 - 65% propanoic acid, 2-methyl-, 3-(benzoyloxy)-2,2,4-

trimeth 1 entyl ester 

### CAS-No. 22527-63-5 20-25% 1,3- entanediol, 2,2,4-trimeth 1-1,3-dibenzoate CAS-No. 68052-23-3 10-15% 2,2,4-trimethyl-1,3-pentanediol diisobutyrate CAS-No. 6846-50-0 The manufacture of benzoate ester for commercial use has been as a bulk reaction and there is no readily available process to synthesize the chemical substance by direct reaction to achieve the purity required for Class 1 substances. Eastman believes that use of the bulk reaction product which is formulated into finished products for commercial sale will more accurately represent exposure and use of the benzoate ester and avoid a costly and technically uncertain purification procedure. As the only sponsor for this substance under the Test Rule, Eastman believes that this application for a modification of the Test Rule for benzoate ester is reasonable and requests the Agency to adopt this modification. ' 78 FRat 65394 4 40 CFR 799.5089(a) 5 78 FRat 65395 

### Page 2of 5p. 7 

# EASTMAN

In accordance with the required tests listed under Table 2 in 40 CFR 799.5089, Eastman intends to provide the following test information: 

### Physical/Chemical Properties R6 4 uir'ed Test - Eastman Test PlanMethod I A1 Freezin

g Point. OECD 102 A2 Boiling Point. ASTM E 1719-05 A3 _ Vapor Pressure. ASTM E 1782-08 ' A4 n-OctanoUWater Partition Coefficient (loglo or lo g K . . ) ASTM E 1147-92 (liquid chromatography) * 

### - A5 Water Solubility. 40 FR 799.6784 column elution ) ** * Estimated log Kow

is >4-6 (based upon KOW WIN) ** Estimated water solubility is > 0 .001-10 mg/L (based upon WSKOW &WATERNT) 

### Environmental Fate-Ready Biodegradation Required Test- Eastman Test Plan Method ISO9408:1999(E) (determination of B Ready Biodegradation oxygen demand in a closed res irometer * * This method selection is based upon preliminary modeled estimates ofthe physical/chemical properties ofthis substance. Should the experimentally determined physical/chemical properties vary fromthe estimated properties, a modification to use one ofthe alternative ready biodegradation methods listed in the final Test Rule may be requested. Aquatic Toxicity 

### Re uiredTest =~ Eastman Test Plan Method Chronic Toxicity to Daphnia, or* ASTM E 1193-97 (Reapproved 

### 2004 C1 Acute Toxicity to Daphnia Acute toxicity to Daphnia (ASTM E 

### 729-96 (Rea roved 2007)

- * Estimated log Kow

is >4.2 (based upon KOW WIN) and therefore a chronic toxicity test appears to be reouired. Ifthe experimental log Kow

is determined to be a 4.2, then the acute test will be performed as an alternative. Mammalian Toxicity-Acute 

### Re uired Test Eastman Test Plan Method D Up and Down Procedure OECD425 Mammalian Toxicity-Genotoxicity 

### Required Test Eastman Test Plan Method El Bacterial Reverse Mutation 40 CFR799.9510 E2 In vitro Mammalian Chromosomal Aberration 40 CFR 799.9537



### Page 3 of 5

# EASTMAN

Mammalian Toxicity-Repeated Dose/Reproduction/Developmental Re uiredTest Eastman Test Plan Method As described below, Eastman ', requests to fulfill this end-point through the use of data already F1 Combined repeated dose toxicity study with the available on the three primary reproduction/developmental toxicity Screening metabolites of the test substance: namely, benzoic acid, 2,2,4- 

### trimethyl-1,3- pentanediol (TMPD) and isobutyrate. Pursuant to the requirements of 40 CFR 790.55(a), Eastman requests the Agency to permit a modification of the requirements under the Test Rule to allowuse of the extensive data set for benzoate ester metabolites as an alternative to the required category F 1 testing. The test substance is formed through an esterification reaction between benzoic acid (CAS-No. 65-85-0) and 2,2,4-trimethyl-1,3-pentanediol diisobutyrate (CAS-No. 6846-50-0; TXIB) . It is well established that similar esters formed between benzoic acid and an alcohol functional unit are efficiently metabolized back to the acid and the alcohol . Studies with di-ethyleneglycol dibenzoate demonstrate that the ester linkages are completely hydrolyzed with no evidence of parent compound present in the urine.6 The use of surrogate health effects data frommetabolites was often regarded to be an acceptable alternative to testing under the auspices of the original HPV program . For benzoates, the EPA accepted this approach as part of the HPV test plans for methyl 4-fonnylbenzoate (CAS 1571- 08-0) 7 and other benzoate derivatives designated under the category of "benzyl derivatives."$ In addition to the benzoic acid, the TXIB generated fromhydrolysis of the test substance yields TMPDand isobutyrate .9 Like the benzoates, the important toxicological data for both TMPD and isobutyrate is available through the Agency's HPV program .' °'1 Eastman believes that using already available toxicology data for benzoic acid, TMPD and isobutyric acid as a surrogate to fulfill certain data requirements of the Test Rule should be acceptable to the Agency. Under 40 CFR 790.55(a) we request the Agency to accept the relevant toxicology data for the metabolites as a surrogate for the testing required under category F1 . The use of a metabolic approach for the test substance also makes sense with respect to animal welfare concerns. By using the available data for metabolites as an alternative to testing, the

6 httn://aons .echa .eurona .eu/reeistered/data/dossiers/DISS-9d8920c9-6c71-3444-e044-00144f67d249/DISS-9d8920c9-6c71- 3444-e044-00144f67d249 DISS-9d8920c9-6c71-3444-e044-00144f67d249 .html ~ htto://www

.epa .eov/chemrtWnubs/summaries/mth4frml/c14624te .htm s htto://www

.eaa .eov/chemrtWoubs/summaries/benzvlde/e13450tc .htm . 9Astill, BD, et al ., Toxicol . Appl . Pharmacol . 22(3) : 387-399, 1972 ~~ TMPD

: htto ://www

.eoa eov/chemrtk/oubs/summaries/24trimlo/c13674tV .Ddf ° Isobutyric acid: htto://webnet.oecd.ore/hov/UI/handler .axd7id=26f9f920-ldc6-4e53-65c4-fdd8b34af201 

### Page 4 of 5p. 9 

# EASTMAN 

# PP EPA can markedly reduce the number ofanimals used to comply with the Test Rule for this



### substance. Eastman would be pleased to discuss any our requested modifications to the test plan with the Agency. If you should have any questions or need additional information, please feel free to contact Gary Shrum, Director ofProduct Safety and Health at (423) 229-2471 or by email at slshrumc(4astman .com . Sincerely, Lar~ &'t'- Leonard Velsor Senior Attorney 

### Eastman Chemical Company P.O . Box 511 Building 75 Kingsport, TN 37662

Page 5 of 5

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