### MEMORANDUM

TO: Greg Macek, EPA/OPPT/CEB Maj’d El-Zoobi, EPA/OPPT/CEB

FROM: Jason A. Sese, ERG Dan-Tam Nguyen, ERG

DATE: June 15, 2009

SUBJECT: Revised Analysis of Potential Uses in the “Glyme” Chemical Category

On May 29, 2009, ERG completed an initial memo reviewing the potential consumer uses of chemicals in the “glyme” chemical cate gory. ERG received a revised technical direction to refine the determination of current consumer uses of glymes, by contacting industry representatives from Ferro Fine Chemicals (Ferro), Novolyte Technologies (Novolyte) and Clariant Corporation (Clariant).

Discussion with Joe Valcho (Novolyte) revealed that Ferro transferred all glyme production to Novolyte and no longer manufactures th ese chemicals. Therefore, Ferro was not contacted regarding the glymes uses. Additionally, Terry Wells (Clariant) noted that the glymes chemicals listed by Clariant are used only in produc ts outside of the United States and could not verify some consumer uses with certainty. However, these are included in the determination for completeness. The industry contacts are listed below and the revised results are compiled in

Table 1.

Industry Contacts

• Novolyte Technologies, Inc.

Joe Valcho

216-750-7603 jvalcho@novolyte.com

• Clariant Corporation Terry L. Wells Product Safety Manager,

Functional Chemicals

704-822-2245 terry.wells@clariant.comTable 1. Compilation of Gly mes and Potential Consumer Uses

Glyme CAS # Use Description Consumer

Use? (Yes/No) Basis

Solvent in pharmaceutical syntheses No Monoglyme is listed as a solvent by the Merck Encyclopedia of Chemicals, Drugs and Biologicals (via Kirk-Othmer Encyclopedia of Technology) 1 and Novolyte Technologies lists a use as a solvent vehicle for pharmaceuticals. 2 Joe Valcho of Novolyte stated that the use of monoglyme in pharmaceutical syntheses is a closed-loop process, where no glyme is present in the final product. 3

Electrolyte

solutions for

lithium batteries Yes Kirk Othmer lists use as an electrolyte in lithium batteries, 4
Clariant Corporation states that it is used as a solvent for electrolytes of lithium batteries 5 and Novolyte Technologies indicates a use as a lithium battery electrolyte solvent

component. 2 Joe Valcho of Novolyte stated that it is possible that batteries containing 1 to 5 percent monoglyme may be sold to consumers through battery distributors; therefore, these batteries may potentially have consumer use. 3 Monoglyme 110-71-4

Component of anti-AIDS drugs No Clariant Corporation lists use as a process solvent for manufacture of anti-HIV drugs. 5 Terry Wells of Clariant stated that the glyme would only be used as a process solvent, with none present in the final product. 6

Diglyme 111-96-6 Solvent in

intermediate and pharmaceutical syntheses No Diglyme is listed as a solvent by the Merck Encyclopedia of Chemicals, Drugs and Biologicals (via Kirk-Othmer Encyclopedia of Technology). 7 Joe Valcho of Novolyte stated that the use of diglyme in pha rmaceutical syntheses a closedloop process, where no glyme is present in the final product. 3

1 HSDB, 2009. Hazardous Substances Data Bank. Accesse d, May 14, 2009, 1,2-Dimet hoxyethane (CAS 110-71-4). http://toxnet.nlm.nih.gov/

2 Novolyte Technologies, 2008. Monoglyme – ethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Monoglyme%20doc.html

3 Conversation with Joe Valcho, Novolyte Technologies, June 11, 2009.

4 Blomgren and Hunter, 2000. Batteries, Primary Cells . Kirk-Othmer Encyclopedia of Chemical Technology. Vol. 3 p.459. Accessed, May 14, 2009. http://mrw.interscience.wile y.com/emrw/9780471238966/kirk /article/primblom.a01/current/pdf

5 Clariant Corporation, 2008. Monoglyme . Accessed, May 14, 2009, http://www.glymes.com/C1257227004EED35/vwWe bPagesByID/FB682C E4C6918C60C12571E80044E250

6 Conversation with Terry Wells, Claria nt Corporation, June 4 and 15, 2009.

7 HSDB, 2009. Hazardous Substances Data Bank. Accessed, May 14, 2009, Diethylene glyc ol dimethyl ether (CAS 111-96-6). http://toxnet.nlm.nih.gov/Table 1. Compilation of Gly mes and Potential Consumer Uses

Glyme CAS # Use Description Consumer

Use? (Yes/No) Basis

Solvent in printing ink manufacturing Yes Novolyte Technologies lists a use as a solvent for printing inks 8

and the Printers National Environmental Assistance Center (PNEAC) includes diglyme on a listing of TRI chemicals possibly found in printing. 9 Joe Valcho of Novolyte stated that it is possible that printing inks containing between one and five percent glyme may be sold to consumers through distributors. 3

Component of anti-AIDS drugs No Clariant Corporation lists a use as a process solvent for manufacture of anti-HIV drugs. 10 Terry Wells of Clariant stated that the glyme would only be used as a process solvent, with none present in the final product. 6

Component of paint Yes The 2006 IUR database (non-CBI) lists consumer use in paints and coatings. 11 It also listed commercial/consumer use in adhesives, sealants and automotive care products.

Process solvent

for adhesives Yes Clariant Corporation and Novolyte Technologies list use as a

solvent for adhesives. 12,13 Terry Wells of Clariant could not specifically state that the adhesives would not be used by

consumers. 6 However, Joe Valcho of Novolyte stated that it is possible that adhesives containing between one and five percent glyme may be sold to consumers through distributors. 3 Triglyme 112-49-2

Component of

brake fluids Yes Clariant Corporation lists a use as a component of brake fluids 12
and a German MSDS lists triglyme as a component for a brake

fluid. 14 No information was found limiting use of this brake

fluid to industrial or commerc ial settings. Additionally, Terry

Wells of Clariant could not affirm that the final brake fluid would not be used by consumers; therefore it is assumed that triglyme may be present in brake fluid accessible by

consumers. 6

8 Novolyte Technologies, 2008. Diglyme – diethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Diglyme%20doc.html

9 Printers National Environmental Assistance Center (PNEAC), 1996. Appendix II – TRI Chemicals Possibly Found In Printing. Accessed, May 14, 2009, http:// www.pneac.org/sheets/a ll/printingtri.pdf

10 Clariant Corporation, 2008. Diglyme . Accessed, May 14, 2009, http://www.glymes.com/C1257227004EED35/vwWe bPagesByID/EB5357DA6B7AE89FC12571E900240417

11 USEPA, 2006. Confidential Inventory Update Reporting Database. V. 1.02

12 Clariant Corporation, 2008. Triglyme . Accessed, May 14, 2009, http://www.glymes.com/C1257227004EED35/vwWebP agesByID/2B3AC3AE3FD248E1C12571E900293AAE

13 Novolyte Technologies, 2008. Triglyme – triethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Triglyme%20doc.html

14 Continental Teves, 2006. Original ATE Brake Fluid DOT 3 (blue); 3m . Accessed, May 14, 2009,http://www.contionline.com/generator/www/us/en/ate/ate/themes/20_ate _brake_products/50_brake_fluid/download/ca_safetydata_d ot3_blue_us.pdfTable 1. Compilation of Gly mes and Potential Consumer Uses

Glyme CAS # Use Description Consumer

Use? (Yes/No) Basis

Component of paint/graffiti

remover Yes Clariant Corporation lists a use as a component of paint/graffiti remover formulations and delacquers. 12 No information was found limiting use of these removers to industrial or commercial settings. Terry Wells of Clariant could not affirm that the final paint/graffiti remover would not be used by consumers; therefore it is assumed that triglyme may be present in paint/graffiti remover accessible by consumers. 6

Binding agent in porcelain powders No Novolyte Technologies lists a use as a binding agent in porcelain powders. 13 Joe Valcho of Novolyte was unsure of this type of process, but stated that the porcelain would have to be fired, therefore burning off any glyme present. 3

Sodium cyanide

– restricted use pesticide (may be

limited to

commercial farming) No Novolyte Technologies lists a use as a process solvent for sodium cyanide production. 13 Sodium cyanide is a toxic substance and pesticides are regulated under the Federal Insecticide, Fungicide, and Rodenticide ACT (FIFRA). Sodium cyanide would not typically be available for consumer use.

Paint production Yes Patent No. 5,919,851 indicates that triglyme may be used a solvent in a paint composition. 15 Joe Valcho of Novolyte stated that it is possible that paint containing between one and five percent glyme may be sold to consumers through distributors. 3

HFC/CFC

lubricant Yes Novolyte Technologies lists a use as a HFC/CFC lubricant. 16
Joe Valcho of Novolyte stated that it is possible that tetraglyme may be present as a CFC lubricant in consumer air conditioners, in a concentration between one and two percent. 3

Dye fixation

additive for

cotton textiles No Novolyte Technologies lists a use as a dye fixation additive for

cotton textiles. 16 Joe Valcho of Novolyte stated that this use is expected to be 100 percent industrial, where it is washed from the textile and recycled, because exposure to glymes in the final

textile is not desired. 3

Solubilizing agent for plastics,

textiles and printing inks Yes Novolyte Technologies lists a use as a solubilizing agent for plastic, textile and printing inks. 16 Joe Valcho of Novolyte stated that it is possible that printing inks containing one to five percent glyme may be sold to consumers through distributors, but are not expected in fina l plastic or textile products. 3 Tetraglyme 143-24-8

Process solvent – fungicide No Novolyte Technologies lists a use as a process solvent for fungicides. 16 Joe Valcho of Novolyte stated that this use is strictly industrial, where no glyme is present in the final product. 3

15 Yamaguchi et al., 1999. Patent 5919851 – Paint Composition and Painted Article . Accessed, May 14, 2009, http://www.freepatentsonline.com/5919851.html

16 Novolyte Technologies, 2008. Tetraglyme – tetraethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Tetraglyme%20doc.htmlTable 1. Compilation of Gly mes and Potential Consumer Uses

Glyme CAS # Use Description Consumer

Use? (Yes/No) Basis

Coalescing agent in the production

process Yes Clariant Corporation lists a use as a coalescing agent in paint

formulations. 17 No information was found limiting use of this paint to industrial or commercial settings. Its function is in the performance of the product itself. Coalescing agents serve to separate the sticky molecules of resin while the product is being stored and applied. Terry Wells of Clariant could not affirm that the final paint would not be used by consumers; therefore it is assumed that tetraglyme may be present in paints accessible by

consumers. 6

Paint stripping Yes Clariant Corporation states that polyglymes are used to formulate paint strippers, a dhesive removers, delacquer

formulations. 18 No information was found limiting use of these strippers to industrial or comme rcial settings. Terry Wells of Clariant could not affirm that the final product would not be used by consumers; therefore it is assumed that triglyme may be present in paint strippers accessible by consumers. 6 Polyglyme 24991-55-7

Solubilizing agent for plastics, textiles, and

paper No Novolyte Technologies lists a use as a solubilizing agent for plastic, textile and paper. 19 Joe Valcho of Novolyte stated that polyglyme is used industrially and is not intended to be in the final plastic, textile or paper products. 3

Solvent for

conductive ink No Novolyte Technologies lists a use as a solvent for conductive

inks. 20 After printing, the solvent is evaporated out of the mixture. Joe Valcho of Novolyte stated that this is expected to be used 100 percent industrially. 3 Butyl Glyme 112-73-2

Printed circuit

etchants No Novolyte Technologies lists a use as a printed circuit etchants. 20
No information was found limiting the use of these products to industrial or commercial settings. Etchants are used in the manufacture of printed circuit boards to remove layers from the

surface of the wafer. Joe Valcho of Novolyte stated that this is expected to be used 100 percent industrially. 3

17 Clariant Corporation, 2008. Tetraglyme . Accessed, May 14, 2009, http://www.glymes.com/C1257227004EED35/vwWebP agesByID/95C6FB 74952C23C7C12571E9002AC573

18 Clariant Corporation, 2008. Polyglycol DME . Accessed, May 14, 2009, http://www.glymes.com/C1257227004EED35/vwWe bPagesByID/5E66447B A43A7E47C125722C00334C5F

19 Novolyte Technologies, 2008. Polyglyme – polyethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Polyglyme%20doc.html

20 Novolyte Technologies, 2008. Polyglyme – polyethylene glycol dimethyl ether . Accessed, May 14, 2009, http://www.novolyte.com/page%20docs/Polyglyme%20doc.html