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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 of Pollution 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 behalf of E. I. Du Pont de Nemours and Company, Inc. I respectfully submit a Letter of Intent 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 noted that per the Guidance by 

manufacturers and based on studies evaluating the hydrolytic behavior, PMDA hydrolyzes in moist air and in 

aqueous solution . Given this 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 11050 and 73 FR 43314) 

Comments pertaining to CAS Number 89-32-7 

CONTAINS NO CBI 
March 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 of Pollution 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 of Public Meeting (74 FR 11050 and 73 FR 43314) 

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 NO CBI 

,- ~ 

-31 YOF? ~ 
Attachment 

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 11050 and 73 FR 43314) 

Comments aertaining to CAS Number 89-32-7 (PMDA) 

" 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 room temperature 

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 (From Kirk 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 g1100 mL water at 25°C 

>30 g/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 MA to moist air (96% 

RH) maleic acid is produced with complete hydrolysis in 21 hr at 22°C. TMA was 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. 

JM Rosenfeld 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 show that in the In the presence of water, TMA rapidly hydrolyzes (within 10 

minutes) to form trimellitic 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 of toxicity 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 PMDA to 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, of low vapor pressure, low octanol water partition coefficient, and readily biodegraded 

in the environment 6 

" 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 from labored 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 of the test material. When these rats were euthanized 10 days after treatment, pathology of the 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 PBT Profiler. 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 

mg/kg values 9-io in rats and mice ranged from 2250-2595, and the acute oral LD50 value in guinea pigs was 1595 

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 of the tissues revealed chronic gastritis in the rats euthanized 4 hours 

after treatment, and no pathology in the recovery animals .