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DuPont Electronics &Communication Barley Mill Plaza 4417 Lancaster Pike Wilmington, DE 19805 February 28, 2011 U .S. EPA Document Control Office (Mail Code 7407M) Office ofPollution Prevention and Toxics ® 1200 Pennsylvania Avenue, NW Washington, D

.C. 20460 Attn: 40 CFR 799.5087 (Docket # EPA-HQ-OPPT-2007-0531)

Dear Sir/Madam

: RE: 40 CFR§799.5087 Chemical Testing Requirements for Second Group

of High Production Volume Chemicals (HPV2) On behalfof E. I . Du Pont de Nemours and Company, Inc. I respectfully submit a Letter ofIntent to Test for substance 1H,3H-Benzo[1,2-c:4,5-c']difuran-1,3,5,7-tetrone [CAS# 89-32-7] identified in the final rule published in the Federal Register on January 7, 2011 [Vol . 76, No 5, 1067-1092] . In comments provided by the DuPont Company on the Proposed Test Rule for this chemical substance dated 30 March 2009 (Document ID : EPA-HQ-OPPT-2007-0531-0377.1), it was notedthat per the Guidance by manufacturers and based on studies evaluating the hydrolytic behavior, PMDAhydrolyzes in moist air and in aqueous solution. Giventhis characteristic, it is anticipated that completing the tests by the deadline set forth in the final rule for certain physical-chemical, environmental fate and aquatic toxicity testing identified by EPA may be difficult. DuPont reserves the right to submit a modification request to the Agency pursuant to 40 CFR §790 .55. Sincerely,

Jane Bradd Andersen DuPont Electronics &Communications Barley Mill Plaza 4417 Lancaster Pike Wilmington, DE 19805 (w) 302-992-5128 

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Encl : Docket No. EPA-HQ-OPPT-2007-0531 Testing of Certain High Production Volume Chemicals; Second Group of Chemicals Proposed Rule and Notice of Public Meeting (74 FR 11050and 73 FR43314) Comments pertaining to CASNumber 89-32-7 

# CONTAINS NOCBIMarch 30, 2009

VIA Federal Express DuPont Haskell Global Cen#6' (`E 1 ;I r~ for Health and Environmentat~cien~~~~ ~ Elkton Road, P.O

. Box 50 Newark, DE 19714009~A-R V 1 A~~ 

## AT 36

Document Control Office (7405M) Office ofPollution Prevention and Toxics Environmental Protection Agency EPA East Building, Room 6428 1201 Constitution Avenue, N.W . Washington, DC 20004 Re: Docket No. EPA-HQ-OPPT-2007-0531 Testing of Certain High Production Volume Chemicals; Second Group of Chemicals Proposed Rule and Notice ofPublic Meeting (74 FR 11050 and 73 FR43314) Comments pertaining to CAS Number 89-32-7 Dear Document Control Officer: The attached comments are submitted for inclusion in the above-identified docket and for consideration at or after the public meeting scheduled for March 31, 2009 . The comments pertain to 1H,3H-benzo[1,2- c:4,5c']difuran-1,3,5,7-tetrone, CAS no . 89-32-7, which is included in the referenced proposed test rule and which is referred to below as "PMDA" . In the attached comments, information on the Physical/Chemical Properties of PMDA, along ~:t~ith a summary of toxicity data that the submitter recently became aware of, is provided. In addition, it-is our understanding that this chemical has been pre-registered under REACh regulations in Europe. --.-lt is expected that a SIEF consortia will be organized to share data on this chemical for REACh. In thaf-case, we believe that further testing should be deferred until all available data are compiled by the SIEF. - Please contact me directly if clarification or further information is needed. Sincerely, 

# a . Ak~ A . Michael Kaplan, Ph.D . Director - Regulatory Affairs AMK:cIp (302) 366-5260 Attachment: (3 pages) 

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## CONTAINS NOCBI ,- ~



# -31YOF? ~Attachment Docket No

. EPA-HQ-OPPT-2007-0531 Testing of Certain High Production Volume Chemicals; Second Group ofChemicals

- Proposed Rule and Notice of Public Meeting (74 FR 11050 and 73 FR43314)

Comments aertaining to CAS Number 89-32-7 (PM DA) " Physical/Chemical Proorties of PMDA Physical properties (from vendor MSDS and Kirk Othmer's Encyclopedia of Chemical Technology, Fourth Ed., Vol . 18, pp. 995, John Wiley and Sons, New York, 1996) are as follows: Form : Density: Melting point : Vapor Pressure: white solid at roomtemperature 1 .68 g/mL 285-6°C 30 mm Hg at 3051C PMDA is a reactive substance and hydrolyzes upon contact with moist air or water, ultimately forming the tetra acid, pyromellitic acid (PMA: CAS 89-05-4) . PMA has the following physical properties (FromKirk Othmer, Vol . 18, pp. 994) : Form : Density: Melting Point : Dissociation constants: Solubility: white solid at room temperature 1 .68 g/mL 282°C pK1 =1 .92; pK2 = 2.87; pK3 = 4.49 ; pK4 = 5.63 1 .5 g1100mL water at 25°C >30g/100 ml, water at 100°C Guidance by the manufacturer and based on studies evaluating the hydrolytic behavior, indicate that PMDA hydrolyzes in moist air and in aqueous solution; hydrolysis rate information was not readily available in aqueous solution. Rosenfeld et al . evaluated hydrolysis of PMDA in moist air (96%RH) using differential thermal analysis; they observed progressively increasing amounts of pyromellitic acid with time (2-72 hr) .1 While their method was not quantitative to derive rate information, the results show that PMDA is not stable in moist air and by inference, water . Refinement of this method was shown in the author's subsequent publication with related substances maleic anhydride (MA : CAS 108-31-6) and trimellitic anhydride (TMA : CAS 552-30-7) .2 They observed that on exposure of MAto moist air (96% RH) maleic acid is produced with complete hydrolysis in 21 hr at 22°C. TMAwas found to be slowly hydrolyzed, with full hydrolysis to trimellitic acid occurring within 113 hr at 22°C. Chiefari et al . report that PMDA was completely hydrolyzed to PMA by refluxing for 1 h in degassed distilled water .3 Collectively, these data indicate that PMDA is unstable in water and hydrolyses to pyromellitic acid. t

s 

### JM Rosenfeld, DF Loncrini, and CB Murphy. 1966. Hydrolysis study of organic acid anhydrides by differential thermal analysis. Pyromellitic Dianhydride. Talanta, 13:1129- 1134. JMRosenfeld and CB Murphy. 1967. Hydrolysis study of organic acid anhydrides by differential thermal analysis. II . Maleic anhydride and trimellitic anhydride . Talanta, 14:91-96. J. Chiefari, B

. Dao, AM

Groth, and JH Hodgkin. (2006) . Water as solvent in polyimide synthesis. II . Processable aromatic polyimides. High Performance Polymers, 8:31-44.Trimellitic anhydride is a chemical analog to PMDA by having one less carboxyl substitution. Data

available for TAW

showthat in the In the presence of water, TMA rapidly hydrolyzes (within 10 minutes) to formtrimellitic acid. Based on their physical chemical properties, both TMA and trimellitic acid are likely to partition to the water compartment but show a very low

order oftoxicity in freshwater fish, invertebrates, and algae (measured No-Observed-Effect-Concentrations (NOECs) of 896, 792 and 739 mg/L, respectively) . Both TMA and trimellitic acid are readily biodegraded under aerobic conditions in sewage sludge. Given these characteristics, it is difficult to understand the need for certain physical-chemical, environmental fate and aquatic toxicity testing identified by EPA. In addition, both octanol :water partitioning and water solubility will be of questionable reliability since hydrolysis will interfere with conduct of the study by converting the PMDAto pyromellitic acid. Based on measured low acute aquatic toxicity for the PMDA analog, TMA, we question the need for aquatic testing on PMDA . The need for a ready biodegradability study to assess environmental fate is also questionable. PIVIDA hydrolyzes into PMA and the biodegradation of PMA has been previously evaluated. PMDA was determined to be readily biodegradable in NIITI 301C test (AVG 89% degradation by direct analysis using total organic carbon at 28d) ; hydrolysis in water was confirmed by detection of PMA .S While biodegradation data were not readily located for PMA, it is predicted to be fully ionizable at neutral pH and water soluble, oflow vapor pressure, low

octanol water partition coefficient, and readily biodegraded in the environment6 " Toxicity Data In an acute inhalation toxicity study in rats, groups of male rats were exposed to the test substance as a dust for 4 hours at nominal concentrations of 2.8, 2.9, 3.2 or 11 .1 mg/L.' The Approximate Lethal Concentration (ALC) was 3 mg/L. Respiratory distress was observed varying fromlabored respiration at the highest level to rapid and slightly heavy breathing at the lower concentrations. The animals exhibited initial gasping, pallor, and inactivity. In an acute oral toxicity study in rats, male rats were dosed with the test substance at concentrations between 670 mg/kg and 5000 mg/kg.8 The ALD was 5,000 mg/kg when the test material was administered as a 20%suspension in peanut oil . Lethal doses caused marked discomfort, severe diarrhea, severe hematuria, weight loss, weakness, and death within one to three days after dosing. Gross and microscopic examination of the tissues showed ulceration of the stomach mucosa, and injury to the tubules and glomeruli of the kidney, with infiltration of blood and polymorphonuclear leukocytes into the capsular space. Sublethal doses caused temporary weight loss. Other than weight loss, no additional signs of toxicity were observed in rats receiving between 670 and 2250 mg/kg ofthe test material . When these rats were euthanized 10 days after treatment, pathology ofthe tissues was not observed.

4 5

6 a 9 io OECD Screening Information Data Set for Trimellitic anhydride and trimellitic acid, Aug . 2006 . Located at http://www

.chem .unep .ch/irptc/sids/oecdsids/TLANA .pdf 

### Official Bulletin of Economy, Trade and Industry, Japan . Mar 17, 2000

. (Former title: The Official Bulletin of the Ministry of International Trade and Industry (published before Jan .6,2001)) US EPA PBTProfiler. Tool located at htto://www .pbtnrofiler.net/default as,p DuPont Internal Report 1962. DuPont Internal Report 1955. Klyachkina, A

.M . et al ., 1975. ToksOcol . Novykh. Prom . Khim . Veshchestv. 14

:125-131 . Kondratyuk, V

.A. et al ., 1986. Gig. Sanit., 11 :79-80.p. 5 p. 4 The acute oral toxicity data were also consistent with several published reports where the acute oral LD50 values in rats and mice ranged from2250-2595, and the acute oral LD50 value in guinea pigs was 1595 mg/kg 9-io Based on this information it would seem that acute toxicity testing is not necessary. A repeated exposure inhalation study was also conducted with 4 male rats exposed for 4 hours per day for 10 days over a two week period to an approximate nominal concentration of 2.8 mg/L.11 During the exposures, the rats showed intermittent gasping and labored respiration. Salivation, inactivity, and an intermittent appearance of red fluid around the eyes, nose and mouth were also noted. Body weight was irregular and significantly lower than that of the controls. Gross and microscopic examination of the respiratory tract of rats exposed singly or repeatedly indicated that the test substance caused significant lung injury at all concentrations probably by acting directly on the pulmonary surfaces. Predominantly the lesions included hyperemia, focal hemorrhages, hyperinflation, and edema of the lungs; and desquamation of the tracheal, bronchial and bronchiolar mucosa. There was also noted focal hemorrhage and tubular necrosis of the kidney, centrilobular hepatocyte hypertrophy in the liver, and hyperplasia in the spleen which persisted through the 14-day observation period. A repeated exposure oral toxicity study was also conducted with groups of six male rats dosed daily five times a week for two weeks to a concentration of 1,000 mg/kg of the test material in peanut oil ." Other than mild body weight effects, no clinical signs of toxicity were observed. Three animals were euthanized four hours after the last treatment and the remaining three ten days after cessation of treatment. Microscopic examination ofthe tissues revealed chronic gastritis in the rats euthanized 4hours after treatment, and no pathology in the recovery animals.