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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 of Pollution Prevention and Toxics (OPPT) 

Environmental Protection Agency 

1200 Pennsylvania Ave., N.W. 

Washington, DC 20460-0001 

Attn: TSCA Section 4. 

IIIIII IIIII IIIIhIIIII IIIII IIIII IIIII IIIII IIIII IIIII IIIII I III 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 of test 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 from REACH registrants 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 NO CBI 
p. 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 of the 

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 now not 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 OECD 422 will be completed and submitted 

to the Agency by the end of March 2013 . 

r, . Required Test ; Current Status 

Physical/Chemical Properties 

A1 Freezing Point. Expected completion in March, 2013 

A2 Boilin g Point. Expected completion in March, 2013 

A3 Vapor Pressure. Expected completion in March, 2013 

A4 n-Octanol/Water Partition Coefficient (log,o 

or lo g K..) 

Completed. Log KoW indicates chronic aquatic toxicity 

testing required. 

A5 Water Solubility. Expected completion in March, 2013 

Environmental Fate-Read Biode radation 

B Read Biode adation Expected completion in March, 2013 

Aquatic Toxicity 

Cl Chronic Toxicity to Daphnia Expected completion in March, 2013 

Mammalian Toxicity-Acute 

D Up and Down Procedure Completed. A final draft report is expected in January, 

2013. 

Mammalian Toxicity -Genotoxicit 

El Bacterial Reverse Mutation Completed. A final 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 and followed by a definitive OECD 422 

stud beginning in the second quarter of 2013. 

Pursuant to the requirements of 40 CFR 790.55(a), Eastman respectfully requests the Agency 

extend the testing schedule under the Plan through the end of 2013 . If you should have 
p. 3 

EASTMAN 

Sincerely, 

Lod u.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 NO CBI 
20 February 2011 

Document Control Office (DCO) (7407M) 

Office of Pollution Prevention and Toxics (OPPT) 

Environmental Protection Agency 

1200 Pennsylvania Ave., N.W. 

Washington, DC 20460-0001 

Attn : 40 CFR 799.5089 ; Docket ID Number 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 CFR 799.5089. 

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 program or 

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 REACH regulation. 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; 40 CFR 799.5089 

Z 75 FR 8575 (February 25, 2010) 

Page 1 of 5 
p. 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 2 3 

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 of a 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 of the 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 FR at 65394 

4 40 CFR 799.5089(a) 

5 78 FR at 65395 

Page 2 of 5 
p. 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 

R64 uir'ed Test 

- 

Eastman Test Plan Method I 

A1 Freezing Point. OECD 102 

A2 Boiling Point. ASTM E 1719-05 

A3 

_ 

Vapor Pressure. ASTM E 1782-08 ' 

A4 n-OctanoUWater Partition Coefficient (loglo or 

log 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 

ISO 9408 :1999(E) (determination of 

B Ready Biodegradation oxygen demand in a closed 

res irometer * 

* This method selection is based upon preliminary modeled estimates of the physical/chemical properties of this substance . 

Should the experimentally determined physical/chemical properties vary from the estimated properties, a modification to use 

one of the alternative ready biodegradation methods listed in the final Test Rule may be requested . 

Aquatic Toxicity 

Re uired Test =~ 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) 

* Estima ted log Kow is >4.2 (based upon KOW WIN) and therefore a chroni c toxicity test appears to be reouired. If the - 

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 OECD 425 

Mammalian Toxicity-Genotoxicity 

Required Test Eastman Test Plan Method 

El Bacterial Reverse Mutation 40 CFR 799 .95 10 

E2 In vitro Mammalian Chromosomal Aberration 40 CFR 799 .9537 

Page 3 of 5 
EASTMAN 

Mammalian Toxicity-Repeated Dose/Reproduction/Developmental 

Re uired Test 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 allow use 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 from metabolites 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 from hydrolysis of the test substance yields 

TMPD and 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 . 

9 Astill, 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 5 
p. 9 

EASTMAN 

PP EPA can markedly reduce the number of animals 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 of Product Safety and Health at (423) 229-2471 or by email at 

slshrum c(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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