### Abt Associates, Inc.

September 3, 2009 1 

## Environment & Resources Division

Date September 9, 2009

To Nishkam Agarwal, US EPA

From Kimberly Wilson, Alice Tome and Tulika Narayan

Subject Actual and Potential Uses of Fourteen Selected Glymes

EPA is in the process of promulgating an existing chemical Significant New Use Rule (SNUR) for fourteen chemicals collectively known as “glymes” ([poly]ethylene glycol diethers). According to the requirement s of an Existing Chemical SNUR, EPA is currently preparing a standard SNUR economic analysis. As a first step to conduct this analysis, this memorandum presents the us es of the fourteen selected glymes:

• monoglyme (Chemical Abstract Service Re gistry Number (CAS-RN) 110-71-4);

• diglyme (CAS-RN 111-96-6);

• triglyme (CAS-RN 112-49-2);

• tetraglyme (CAS-RN 143-24-8);

• polyglyme (CAS-RN 24991-55-7);

• butyl diglyme (CAS-RN 112-73-2);

• ethyldiglyme (CAS-RN 112-36-7);

• tetraethylene glycol dibuty l ether (CAS-RN 112-98-1);

• ethylene glycol diethyl ether (CAS-RN 629-14-1);

• tetraethylene glycol diethyl ether (CAS-RN 4353-28-0);

• pentaethylene glycol diethyl ether (CAS-RN 23601-39-0);

• polyethylene glycol dibutyl ether (CAS-RN)31885-97-9);

• pentaethylene glycol dibutyl et her (CAS-RN 51105-00-1); and

• butyltriglyme (CAS-RN 63512-36-7).

Abt Associates researched several sour ces on the use of glymes that include:

• TSCA Inventory Update Rule (IU R) public database (1986-2006); 1



### • SRI Chemical Economics Handbook and S RI Specialty Chemicals Program books (SRI); 2

1 “IUR Data” available at http://www.epa.gov/iur/tools/data/index.htm (Accessed August 31, 2009)

2 While the SRI Chemical Economics Handbook had a section on glycol ethers the chemicals discussed

were monoethers and not diethers

. 

# memorandum

### Abt Associates, Inc.

September 3, 2009 2 • Industry and trade magazines such as i ndustry and trade magazines such as the “Chemical Market Reporter” and the “Chemical Engineering News”;

• EPA Website;

• NIH’s Hazardous Substances Databank (HSDB); 3



### • Score Card: The Pollution Information Website (Scorecard); 4 

### and

• General web search.

In addition to these data sources, we incl uded the information from a memorandum that Eastern Research Group (ERG) prepared fo r U.S. EPA on the uses of six glymes (monoglyme, digylme, triglyme, tetraglyme , polyglyme, and butyl glyme) based on phone interviews with the i ndustry (ERG, 2009).

Abt Associates considered all uses from phone interviews with industry as confirmed uses of the glymes or “actual” uses. All th e uses from the remaining data sources are considered “reported” uses, or uses that are not confirmed uses of the glymes. 5 

### The IUR

database lists the uses under a combined h eading of “consumer/commercial” so that it was not possible to separate out the consumer and non-consum er uses. Therefore, we considered these uses as reported consumer and/or reported non-consumer uses based on the specific applications. The next section pr esents these actual and reported uses of the fourteen glymes.

Uses

Glymes are used in a variety of consumer and non-consumer applications. Some actual consumer uses of the fourteen selected gl ymes include use in print ink manufacturing, adhesives production, brake fluid, and lithium batteries. Actual non-consumer uses of the selected glymes include use in pharmaceuti cal products and the production of electronic

circuit boards.

The actual and reported consumer and non- consumer uses of each chemical are summarized in Table 1 below. For several gl ymes, one of the reported uses listed is “IUR other use.” This represents a potenti ally broad category of uses and includes all

uses other than the nineteen listed in the IUR reporting form: 1) Adhesives and sealants, 2) Agricultural products (non- pesticidal), 3) Artists' s upplies, 4) Automotive care products, 5) Electrical and elec tronic products, 6) Fabrics, te xtiles and apparel, 7) Glass and ceramic products, 8) Lawn and garden produ cts (non-pesticidal), 9) Leather products, 10) Lubricants, greases and fuel additives, 11) Metal products, 12) Paints and coatings, 13) Paper products, 14) Photographic supplie s, 15) Polishes and sanitation goods, 16) Rubber and plastic products, 17) Soaps and detergents, 18) Transportation products, and 19) Wood and wood furniture (see Appendix A).

3 http://toxnet.nlm.nih.gov/

4 www.scorecard.org

5 Although SRI is considered a reliable source on us es, no information was available from this source on the uses of these fourteen glymes.

### Abt Associates, Inc.

September 3, 2009 3 The uses for each of the glymes are discusse d in more detail afte r the table along with information on production volume and use fr om the public IUR databases from 1986 to

2006. 6

6 Information on use is available only in the 2006 public IUR database.Abt Associates, Inc.September 3, 20094Table 1: Summary of the Actual and ReportedUses of the Fourteen Selected GlymesConsumer Use(s)Non-Consumer use(s)GlymeCAS-RNActual Use1SourceReported Use2SourceActual Use1SourceReported Use2SourceSolvent forlithium ionbatteriesClariant,2009 andNovotlyteTechnologies,2009Solvent inpharmaceuticalsynthesesNovolyteTechnologies,2009Solvent inmanufacture ofanti-AIDS drugsClariant,2009IUR other use3IUR (EPA,2006b)Printing circuitboardmanufacturingScorecard, 2005Solvent inorganometallicreactionsClariant, 2008Solvent in sugarand carbohydratechemistryClariant, 2008Monoglyme 110-71-4Surface treatmentof aluminumClariant, 2008Abt Associates, Inc.September 3, 20095Consumer Use(s)Non-Consumer use(s)GlymeCAS-RNActual Use1SourceReported Use2SourceActual Use1SourceReported Use2SourceSolvent inprinting inkmanufacturingNovolyteTechnologies,2008Solvent inintermediate andpharmaceuticalsynthesesNovolyteTechnologies,2009Adhesives andsealants4IUR (EPA,2006b)Adhesives andsealants4IUR (EPA,2006b)Solvent forlithium aluminumhydride andsodiumborohydridereductionsFerro, 2009Automotive Care4Brake FluidIUR (EPA,2006b)Ferro, 2009Automotive CareIUR (EPA,2006b)Paints andcoatings4IUR (EPA,2006b)Paints andcoatingsIUR (EPA,2006b)Diglyme 111-96-6IUR other use3IUR (EPA,2006b)Process solventfor adhesivesClariant,2009Binding agent inporcelain powdersNovolyteTechnologies,2009Component ofbrake fluidsClariant,2009Sodium cyanide –restricted usepesticide (may belimited tocommercialfarming)NovolyteTechnologies,2009Triglyme 112-49-2Component ofpaint/graffitiNovolyteTechnologies,Solvent inmethylationClariant, 2008Abt Associates, Inc.September 3, 20096Consumer Use(s)Non-Consumer use(s)GlymeCAS-RNActual Use1SourceReported Use2SourceActual Use1SourceReported Use2Sourceremover 2009reactionsPaint productionNovolyteTechnologies,2009HFC/CFClubricantNovolyteTechnologies,2009Dye fixationadditive for cottontextiles;NovolyteTechnologies,2009Fabrics, textilesand apparel.5IUR (EPA,2006b)Solubilizingagent forprinting inksNovolyteTechnologies,2009Process solvent –fungicideNovolyteTechnologies,2009Coalescingagent for paintprocessClariant,2009Solubilizing agentfor plastics andtextilesNovolyteTechnologies,2009Tetraglyme 143-24-8Gas Scrubbing Clariant, 2008FragranceproductionFerro, 2009Solubilizing agentfor plastics, textiles,and paperNovolyteTechnologies,2009Gas Scrubbing Clariant, 2008Paint strippingClariant,2009Automotive careproducts4IUR (EPA,2006b)Automotive careproductsIUR (EPA,2006b)Paper products4IUR (EPA,2006b)Paper productsIUR (EPA,2006b)Adhesive removers Ferro, 2009Polyglyme 24991-55-7Anti-fogcompounds andbrake fluidFerro, 2009Solvent forconductive inkNovolyteTechnologiesButyl Diglyme 112-73-2Printed circuitetchantsNovolyteTechnologiesAbt Associates, Inc.September 3, 20097Consumer Use(s)Non-Consumer use(s)GlymeCAS-RNActual Use1SourceReported Use2SourceActual Use1SourceReported Use2SourceSolvent inGringard reagentsClariant, 2008Metal extraction Clariant, 2008Coatings andadhesivesmanufacturingScorecard,2005Solvent in plasticresins andcompoundsHSDB, 2009Solvent in printinginksAsh, 1996Solvent in rubberchemicalsHSDB, 2009Ethyldiglyme 112-36-7Paint and paintvarnishesScorecard,2005Brake fluidWagner,1998Electronic circuitboard productionHitachi, 1992Tetraethyleneglycol dibutylether112-98-1Semi conductordevicesproductionHitachi, 2006Paint production Ash, 2009Production ofester gum, shellac,resins and oilsHSDB, 2009Production of“other” polishesScorecard,2005Ethyleneglycol diethylether629-14-1Adhesive solventand polycarbonateswelling agentFerro 2009Brake fluidFederalMogul, ,2007 andWagner,1998Electronic circuitboard productionHitachi, 1992Tetraethyleneglycol diethylether4353-28-0Semi conductordevicesproductionHitachi, 2006Pentaethyleneglycol diethylether23601-39-0Brake fluidCrossPackaging,1998Electronic circuitboard productionCross Packaging,2008Abt Associates, Inc.September 3, 20098Consumer Use(s)Non-Consumer use(s)GlymeCAS-RNActual Use1SourceReported Use2SourceActual Use1SourceReported Use2SourceCoating productionClariant,2008Soldering ofelectroniccomponentsMulticoreSolders Limited,1990Gel laundrydetergentUnilever,2007ActivepharmaceuticalingredientClariant, 2008Polyethyleneglycol dibutylether31885-97-9Gas scrubbing Clariant, 2008Pentaethyleneglycol dibutylether51105-00-1Production ofmethacrylic acidLONGZA AG,19676Gas scrubbingSchiller andGmehling, 19926Butyltriglyme 63512-36-7Production ofmethacrylic acidLONGZA AG,19676Notes:1A use is considered an “actual use” if itis listed as a use on SRI (no uses found),or if a company representative has confirmed the use as a consumer ornon-consumer use, in the phoneconversation with ERG (ERG, 2009).2A use is considered a “reported” use ifit is listed as a use in the public IUR database (because IUR does not distinguish between consumer and non-consumer uses), the HSDB, or listed on thecompany’s website as a use, but was not confirmed as a use by a company representative.3See Appendix A for the list of uses excluded from the “other” category in IUR.4Since the IUR data did not clearly indicate if the use isconsumer or non-consumer for the specific glyme, the use is listed asa reported consumer use if the phone interviews determined anactual consumer use for the same use category, but for a different glyme. For example, “paints and coatings” use for Diglyme is considered a reported consumer use because Novoltye andClariant report consumer use for paint production for both Trigylme and Tetraglyme. “Automotivecare products” for Diglyme andPolyglyme are assumed to contain brake fluid which Clariantconfirmed as a consumer use for Triglyme. Therefore automotivecare products are considered reported consumer use. “Fabrics, textiles and apparel” use for Tetraglyme is reported nonconsumer use because Novolyte Technologies confirms that “dyefixation additive for cotton textiles” is a non-consumer use. The uses listed under the adhesivesand sealants, and paper productscategory are considered reported consumeruses based on our judgment that theseuses could be consumer uses.5Because the date of the reference Abt Associates is unsure ifthe chemical is still used in this application.

### Abt Associates, Inc.

September 3, 2009 9 Monoglyme

Monoglyme has several uses as an industria l solvent and is a high volume chemical (HPV) with annual U.S. production levels greater than 1,000,000 lb s per year (EPA, 2007). Table 2 below presents the producti on volume and use information from the 1986-2006 public IUR databases. The IUR data base lists use of monoglyme in “other” category that is also listed as a possible us e in children’s product. However, no details on the specific use are available.

Monoglyme has one actual consumer use, as an electrolyte solvent in lithium ion batteries (Novolyte Technologies, 2009 and Clariant, 2009). The use of monogl yme as a solvent in lithium battery manufacturing is found to ha ve moderately toxic acute exposure levels (Archuleta, 1994). The chemical also has re ported application in a process to treat aluminum surfaces so they ar e less reactive (Clari ant, 2008). Additional research would be required to determine if there are any consumer uses in this application.

Among the actual non-consumer uses, Monoglyme is currently used as a solvent in pharmaceutical production (Novolyte Technolog ies, 2009) and as a component of antiAIDS drugs (Clariant, 2009).

Monoglyme has several reported uses including use in the inner and outer layer etching of printed circuit board manu facturing (Scorecard, 2005). Monoglyme has other reported applications, because of its low boiling point and high stability, even at high pH. It is frequently used in reactions with strong base s and in mixtures where solvent separation and recovery is necessary (Ferro, 2009). M onoglyme also has reported application as an inert special solvent for organo metallic re actions, particularly those involving alkali metals, and metal-catalyzed couplings (Clari ant, 2008). For example, reaction rates for Suzuki coupling, the Pd-catalyzed carbon-car bon cross coupling of boronic acids with organic electrophiles, are dras tically increased in monoglyme solvent, when compared to traditional alternatives such as tetrahydro furan (THF) (Clariant, 2008). It is also reportedly used as a solvent for oligo- and polys accharides and is fre quently used in sugar and carbohydrate chemistry, including protec tion reactions (Clariant, 2008).

### Abt Associates, Inc.

September 3, 2009 10 Table 2: IUR Production Volume and Co nsumer/Commercial Data for Monoglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 0.01 ≤ PV < 0.50 Not Available Not Available

1990 1.00 ≤ PV < 10.0 Not Available Not Available

1994 1.00 ≤ PV < 10.0 Not Available Not Available

1998 1.00 ≤ PV < 10.0 Not Available Not Available

2002 1.00 ≤ PV < 10.0 Not Available Not Available Monoglyme

2006 1.00 ≤ PV < 10.0 Other Yes

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collec ted for the IUR until the 2006 reporting cycle.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Diglyme

Diglyme has only one actual consumer use as a solvent in printing ink production.(Novolyte Technologies , 2009). Reported consumer uses for Diglyme include use in automotive care (EPA, 2006b) as a com ponent of brake fluid (Ferro, 2009), paints and coatings (EPA, 2006b), and adhe sives and sealants (EPA, 2006b).

The actual non-consumer use diglyme is as a solvent in the produc tion of pharmaceutical products (Novolite Technologies, 2009). It is also reporte dly used as a solvent for lithium aluminum hydride and sodium borohydride reductions (Clariant, 2008). Other reported non-consumer uses include its use in automotive care (E PA, 2006b), paints and coating (EPA, 2006b) and adhesives and sealants (EPA, 2006b).

Like monoglyme, diglyme is an HPV chemical and is reported in th e IUR database (EPA, 2007). The table below presents the producti on volume and use information from the 1986-2006 public IUR databases.

Table 3: IUR Production Volume and Consumer/Commercial Data for Diglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s Products 3

1986 1.00 ≤ PV < 10.0 Not Available Not Available

1990 1.00 ≤ PV < 10.0 Not Available Not Available

1994 1.00 ≤ PV < 10.0 Not Available Not Available

1998 1.00 ≤ PV < 10.0 Not Available Not Available

2002 1.00 ≤ PV < 10.0 Not Available Not Available

Adhesives and sealants Not Readily

Obtainable 4

Automotive care products Not Readily

Obtainable Diglyme

2006 1.00 ≤ PV < 10.0

Paints and coatings No

### Abt Associates, Inc.

September 3, 2009 11 Other Not Readily

Obtainable

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

4 “Not Readily Obtainable” indicates this in formation was unknown to the IUR submitter

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Ch emical, including Manufacturing, Processing and Use Information ( http://cfpub.epa.gov/iursearch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Triglyme

IUR data shows that triglyme was produced below the IUR reporting threshold (25,000 lbs at a single site) in 1986, 1990, and 2006 (EPA, 2002 and EPA, 2006b) and that between 10,000 and 500,000 lbs of the chemical were produced during all other reporting years (EPA, 2002). Table 4 below presents the information on the production volume and use from the 1986-2006 public IUR databases.

Triglyme is more stable than monoglyme and diglyme because of the additional ethylene glycol unit which increases the boiling point range for reactions that use it as a solvent. Triglyme offers a particular ly versatile route for the in situ generation of diborane because of its improved stability (Clariant, 2008). In addition, it is a selective solvent for methylation reactions with th e environmentally benign dimethyl carbonate, methylations of aromatic and aliphatic compounds can be carried out under mild conditions without the need for a phase transfer catalyst (Clariant, 2008).

Triglyme has several confirmed consumer uses including use in brake fluid, as a solvent in adhesives production (Clariant, 2009), as a component of paint and graffiti remover formulations, and in paint production (Novolyte Technologies, 2009). Triglyme also has actual non-consumer uses as a binding agen t in porcelain powders and as a reaction

solvent for the manufacture of sodi um cyanide (Novolyte Technologies, 2009).

### Abt Associates, Inc.

September 3, 2009 12 Table 4: IUR Production Volume and Co nsumer/Commercial Data for Triglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s Products 3

1986 No Reports Not Available Not Available
1990 No Reports Not Available Not Available

1994 0.01 ≤ PV < 0.50 Not Available Not Available

1998 0.01 ≤ PV < 0.50 Not Available Not Available

2002 0.01 ≤ PV < 0.50 Not Available Not Available Triglyme

2006 No Reports No Reports No Reports

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collec ted for the IUR until the 2006 reporting cycle.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Ch emical, including Manufacturing, Processing and Use Information ( http://cfpub.epa.gov/iursearch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Tetraglyme

Tetraglyme has several actual consumer uses including as a solubilizing agent for printing inks (Novolite Technologies, 2009), and as a coalescing agent in paint production (Clariant, 2009). Another actual consumer use of tetraglyme is as a HFC/CFC lubricant which may be used in consumer air conditioners (Novolite Technologies, 2009). Actual non-consumer uses include use as a solublizing agent in textiles and plastics, as a dye fixation additive for cotton textiles, and as a fungicide process solvent (Novolite Technologies, 2009). Tetraglyme ha s a reported use in fabrics, textiles and apparel (EPA, 2006b) and as a ga s scrubbing agent and has been shown to effectively remove CO, CO 2 

### , H 2 

### S, and other sour-gas components from natural, synthetic, or ammonia gas streams (Fe rro, 2009). The table below presents the production volume and use information from the 1986-2006 public IUR databases.

### Abt Associates, Inc.

September 3, 2009 13 Table 5: IUR Production Volume and Co nsumer/Commercial Data for Tetraglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s Products

3

1986 0.01 ≤ PV < 0.50 Not Available Not Available

1990 0.01 ≤ PV < 0.50 Not Available Not Available

1994 0.01 ≤ PV < 0.50 Not Available Not Available

1998 0.01 ≤ PV < 0.50 Not Available Not Available

2002 0.01 ≤ PV < 0.50 Not Available Not Available Tetraglyme

2006 0.01 ≤ PV < 0.50 Fabrics, textiles and apparel Not Readily

Obtainable 4

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

4 “Not Readily Obtainable” indicates this in formation was unknown to the IUR submitter

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Polyglyme

Polyglyme, like monoglyme and diglyme, is an HPV chemical (EPA, 2006a). It is often used as special, high boiling solvents fo r several chemical reactions including depolymerization and hydrogenation. Polygl yme has an actual consumer use in the formulation of paint stripping. Reported c onsumer uses of polyglyme include use in adhesive removers, fragrance production, an ti-fog compounds, brake fluid (Ferro, 2009), automotive care products and paper products (EPA, 2006b). Polyglyme also has several non-consumer uses. Actual non-consumer uses for polyglyme include use as a solubilizing agent for plastic, textile, and pa per processes (Novolite Technologies, 2009). A reported non-consumer use for the chemical is in removing sour gas compounds from gas streams, absorbing hydrogenated liquids , and scrubbing gas stacks (Ferro, 2009). Other reported non-consumer uses include use in paper product s and automotive care products (EPA, 2006b). The table below presents the production volume and use information from the 1986-2006 public IUR databases.

### Abt Associates, Inc.

September 3, 2009 14 Table 6: IUR Production Volume and Co nsumer/Commercial Data for Polyglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 1.00 ≤ PV < 10.0 Not Available Not Available

1990 1.00 ≤ PV < 10.0 Not Available Not Available
1994 No Reports Not Available Not Available

1998 0.01 ≤ PV < 0.50 Not Available Not Available

2002 0.01 ≤ PV < 0.50 Not Available Not Available

Automotive care products Not Readily

Obtainable 4 Polyglyme

2006 0.01 ≤ PV < 0.50
Paper products Not Readily

Obtainable

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collec ted for the IUR until the 2006 reporting cycle.

4 “Not Readily Obtainable” indicates this in formation was unknown to the IUR submitter

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Butyl diglyme

Butyl diglyme is used in similar applicati ons to the other methyl glymes, however it differs in the fact that it is very insolubl e in water. Unlike the other glymes, butyl diglyme has no consumer uses. Actual non-c onsumer uses include use as a solvent for conductive printing ink and in the production of printed circuit etchants (Novolite Technologies, 2009). Reported non-consumer uses include use in the preparation of and reaction with Grignard reagents (Clari ant, 2008). The high solubility of MgCl 2 

### (the main byproduct of Grignard reactions) in butyl digl yme helps to improve the isolation of the desired product, and the high flash point expa nds the usefulness of Grignard reactions to

an industrial scale. This is not feasible wh en using traditional Grignard solvents; THF or diethyl ether (Clariant, 2008). Butyl diglyme also has reporte d uses in metal extractions. It is able to extract gold fr om hydrochloric acid which contains other metals, such as silver, copper, and platinum metals (Cheremisinoff, 2003). The process can be expanded to recover gold from computers, electronics, and printed circuit waste (Clariant, 2008). The table below presents the production vol ume and use information from the 1986-2006 public IUR databases.

### Abt Associates, Inc.

September 3, 2009 15 Table 7: IUR Production Volume and Consumer/Commercial Data for Butyl Diglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 No Reports Not Available Not Available

1990 0.01 ≤ PV < 0.50 Not Available Not Available

1994 0.01 ≤ PV < 0.50 Not Available Not Available

1998 0.01 ≤ PV < 0.50 Not Available Not Available

2002 0.01 ≤ PV < 0.50 Not Available Not Available Butyl diglyme

2006 0.01 ≤ PV < 0.50 Not Reported 4 Not Reported 4

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

4 IUR only collects use and processing information for chemicals that have a manufacturing volume greater than 300,000 lbs during the reporting year.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Ethyldiglyme

Ethyldiglyme has no actual consumer uses but does have several reported consumer uses. It is used in paint and paint varnishes, in coatings and adhesive s manufacturing (Score Card, 2005) and as a solvent in printing i nk production (Ash, 1996). Ethyldiglyme also has several reported non-consumer uses. The chemical is reportedly used as a highboiling solvent for nitro cellulose, resins, and lacquers (As h, 2009). It is highly stable and has reported uses as a solubilizer in organic synthesis (Ash, 2009). In addition, ethyldiglyme is reportedly us ed in several manufacturing processes, including as a solvent in the production of plastic resins and compounds , rubber chemicals (HSDB, 2009). The table below presents the producti on volume and use information from the 1986-2006 public IUR databases.

### Abt Associates, Inc.

September 3, 2009 16 Table 8: IUR Production Volume and Consumer/Commercial Data for Ethyldiglyme

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 0.01 ≤ PV < 0.50 Not Available Not Available

1990 0.01 ≤ PV < 0.50 Not Available Not Available

1994 0.01 ≤ PV < 0.50 Not Available Not Available

1998 0.01 ≤ PV < 0.50 Not Available Not Available

2002 0.01 ≤ PV < 0.50 Not Available Not Available Butyl diglyme

2006 0.01 ≤ PV < 0.50 Not Reported 4 Not Reported 4

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

4 IUR only collects use and processing information for chemicals that have a manufacturing volume greater than 300,000 lbs during the reporting year.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Tetraethylene glycol dibutyl ether

Tertaethylene glycol dibutyl ether has a reporte d consumer use as a br ake fluid ingredient (Federal Mogul, 2007 and Wagner, 1998) and may comprise between 10 and 50 percent of the product (Wagner, 1998). The chemical also has reported non-consumer uses in the production of heat resistant resin pastes. These pastes are used to produce electronic circuit boards (Hitach i Chemical Company, 1992) and semiconductor devices (Hitachi Chemical Company, 2006). Information on th is glyme is not re ported in the 1986-2000

IUR databases.

Ethylene glycol diethyl ether

Ethylene glycol diethyl ether has reported consumer use as solvent in paint production (Ash 2009), as well as use as an adhesive solvent and polycarbonate swelling agent (Ferro, 2009). Another reported consumer use is in the preparati on of “other” polishes and related products (Score Ca rd, 2005). A review of the NAICS definition of “Other polishing preparations and re lated products” suggests that this would include metal polishes (U.S. Census Bureau, 2002). The ch emical’s only non-consumer use is its reported use in the production of ester gum, shellac, resins and oils (HSDB, 2009). The table below presents the production vol ume and use information from the 1986-2006 public IUR databases.

### Abt Associates, Inc.

September 3, 2009 17 Table 9: IUR Production Volume and Consumer/Commercial Data for Ethylene Glycol Diethyl Ether

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 No Reports Not Available Not Available

1990 0.01 ≤ PV < 0.50 Not Available Not Available
1994 No Reports Not Available Not Available
1998 No Reports Not Available Not Available
2002 No Reports Not Available Not Available Ethylene glycol diethyl

ether

2006 0.01 ≤ PV < 0.50 Not Reported 4 Not Reported 4

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

4 IUR only collects use and processing information for chemicals that have a manufacturing volume greater than 300,000 lbs during the reporting year.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Tetraethylene glycol diethyl ether

Tertaethylene glycol diethyl ether has many of the same reported applications as tetraethylene glycol dibutyl et her. Both chemicals have reported consumer uses as ingredients in brake fluid (Federal Mogul, 2007 and Wagner, 1998). The brake fluid may contain between 10 and 50 percent tertaethylen e glycol diethyl ether (Wagner, 1998). In addition, the chemical has a reportedly non-c onsumer use in the production of a heat

resistant resin which in turn is used in th e production of electronic circuit boards (Hitachi Chemical Company, 1992) and semiconducto r devices (Hitachi Chemical Company, 2006). The table below presents the producti on volume and use information from the 1986-2006 public IUR database.

### Abt Associates, Inc.

September 3, 2009 18 Table 10: IUR Production Volume and Consumer/Commercial Data for Tertaethylene glycol diethyl ether

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 0.01 ≤ PV < 0.50 Not Available Not Available
1990 No Reports Not Available Not Available
1994 No Reports Not Available Not Available
1998 No Reports Not Available Not Available
2002 No Reports Not Available Not Available Tertaethylene glycol diethyl ether

2006 No Reports No Reports No Reports

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009



### Pentaethylene glycol diethyl ether

Like tetraethylene glycol diet hyl and tetraethylene glycol dibutyl ether, pentaethylene glycol diethyl ether has a reported consumer us e as an ingredient in brake fluid but again

it is not clear if there is c onsumer use. Pentaethylene glycol diethyl may comprise between 2 and 4 percent of synthetic hydr aulic brake fluid (Cross Packaging, 2008). Furthermore, the chemical has a reported c onsumer use in the so ldering of electronic circuit boards (US Patent 4871109). The tabl e below presents the production volume and use information from the 1986-2006 public IUR database.

Table 11: IUR Production Volume and Consumer/Commercial Data for Pentaethylene glycol diethyl ether

Chemical Year Reported Production Volume (Millions of Pounds) Consumer/Commercial

Use 1,2 Intended for Use in

Children’s

Products 3

1986 0.01 ≤ PV < 0.50 Not Available Not Available

1990 0.01 ≤ PV < 0.50 Not Available Not Available
1994 No Reports Not Available Not Available

1998 0.50 ≤ PV < 1.00 Not Available Not Available

2002 1.00 ≤ PV < 10.0 Not Available Not Available pentaethylene glycol diethyl

ether

2006 1.00 ≤ PV < 10.0 Claimed as CBI Claimed as CBI

Notes: 1 No consumer or commercial use information was co llected for the IUR until the 2006 reporting cycle.

2 See Appendix A for a complete list of 2006 IUR consumer and comme rcial use categories.

3 No children’s use information was collected for the IUR until the 2006 reporting cycle.

Sources: EPA, 2006b. Non-confidential 2006 IUR Records by Chemical, including Manufac turing, Processing and Use Information ( http://cfpub.epa.gov/iurs earch/index.cfm?s=chem ) Accessed August 28, 2009 EPA, 2002. Non-confidential IUR Produc tion Volume Information (1986-2002) ( http://www.epa.gov/iur/tools/data/2002-vol.htm ) Accessed August 28, 2009

### Abt Associates, Inc.

September 3, 2009 19 Polyethylene glycol dibutyl ether

Polyethylene glycol dibutyl ether has severa l reported non-consumer uses, including use as a solvent in several pharmaceutical synt heses including antiviral and blood pressure medication (Clariant, 2008). In additi on, the chemical has reported non-consumer applications as a gas scrubbing liquid, in the production of various coatings (Clariant, 2008) and in the soldering of electronic components (Multicore Solders Limited, 1990). Polyethylene glycol dibutyl ether has only one reported consumer us e, in the production of gel laundry detergents (Unile ver, 2007). Information on this glyme is not reported in

the 1986-2000 IUR databases.

Pentaethylene glycol dibutyl ether

We were unable to find any consumer uses of pentaethylene glycol di butyl either in the sources we generally refer to, such as the SRI Chemical Economics Handbook 5 and IUR databases. However, an old reference suggest s that this glyme was reportedly used in the production of methacrylic acid (LONZA AG, 196 7). Because of the date of this reference, 1967, it is unknown if the chemical is still used to produce methacrylic acid. Methacrylic acid is used in the production of polymers, resins, and adhesives (HSDB, 2009). Information on this glyme is not reported in the 1986-2000 IUR databases.

Butyltriglyme

Similar to pentaethylene glycol dibutyl ether, we were unable to identify any consumer uses for butyltriglyme in recently published so urces. However, in the past the chemical has reportedly been used as a scrubbing liqui d in the removal or recycling of various components of gas streams (Schiller and Gmehling, 1992). Butyltriglyme has also reportedly been used in the production of methacrylic acid (LONZA AG, 1967). Because these references are dated (17-32 years old), it is unknown if butyltrigly me is still used in these applications. Information on this glyme is not reported in the 1986-2000 IUR

databases.

### Abt Associates, Inc.

September 3, 2009 20 References 

## :

Archuleta, 1994. Melcita M. Archuleta “Toxi city of Materials used in the Manufacture

of Lithium Batteries”. Sandia Nati onal Laboratories, 1994. Available at http://www.osti.gov/bridge/servlet s/purl/10148721-CMqxf5/native/10148721.pdf (accessed April 24, 2009)

Ash, 1996. Michael and Irene Ash. Handbook of Paint and Coating Raw Materials : Chemical Products Dictionary

Ash, 2009. Michael and Irene Ash. Specialty Chemical Source Book 4 th 

### Addition SIR Publishing, Endicott NY. 2009

Cao, 2001. Xu-Liang Cao and Jiping Zhu . “ Monitoring method for airborne glymes and its application in fuel ex haust emission measurement” Chemosphere . Vol 45. Is. 6-7 p. 911-917 . Abt Associates currently only has the abstract.

Cheremisinoff, 2003. Nicholas P. Cheremis inoff and Wesley L. Archer. “Ethers”,

Industrial Solvents Handbook CRC Press, 2003

Clariant, 2008. Clariant website. available at http://www.glymes.com (accessed August 21, 2009)

Clariant, 2009. Personal Communi cation between Terry L. Wells of Clariant Corporation and Eastern Research Group. June 2009.

Cross Packaging, 2008. “Cross Packaging Co mpany Material Safety Data Sheet”

available at: http://www.crossoil.com/lib/docs/pa ckaging_msds/1Gard_DOT_3_DOT_4_BRA KEFLUID.pdf (accessed August 21, 2009)

ERG, 2009 “Revised Analysis of Potential Uses in the “Glyme” Chemical Category” memorandum from Eastern Research Group (ERG) to U.S.EPA, June, 19, 2009

EPA, 2002. US Environmental Protection Ag ency “Non-confidential IUR Production Volume Information (1986-2002)” Available at http://www.epa.gov/iur/t ools/data/2002-vol.htm (accessed August 28, 2009)

EPA, 2006a. US Environmental Protection Ag ency “1990 HPV Challenge Program List: Revised January 20, 2006”. 2006. Available at http://www.epa.gov/HPV/pubs/update/hpv_1990.pdf (accessed April 24, 2009)

EPA, 2006b. US Environmental Protecti on Agency “Non-confidential 2006 IUR Records by Chemical, including Ma nufacturing, Processing and Use

### Abt Associates, Inc.

September 3, 2009 21 Information” Available at http://cfpub.epa.gov/iursearch/index.cfm?s=chem (accessed August 28, 2009)

EPA, 2007. US Environmental Protection Agency “Sponsored Chemicals: High Production Volume (HPV) Challe nge Program”. 2007. Available at http://www.epa.gov/HPV/pubs/update/spnchems.htm (accessed April 24, 2009)

Federal Mogul, 2007. “Material Safety Data Sheet” available at: http://federalmogul.com/NR/rdonlyres/010B0093-1541-43B5-A0E1- ED20037C5F49/0/Component_B_US.pdf (accessed August 20, 2009)

Ferro, 2009. Ferro website. Available at http://web.archive.org/web/20071102160331/ www.ferro.com/Our+Products/Fine +Chemicals/Products+and+Markets/Glymes/ (Accessed August 19, 2009)



### Hitachi Chemical Company, 1992. “US Patent 5087658 - Heat-resistant resin paste and integrated circuit device produced by using the heat-resistant resin paste”

available at http://www.patentstorm.us /patents/5087658/claims.html (accessed August 20, 2009)

Hitachi Chemical Company, 2006. “US Pa tent 7061081 - Resin composition, heat resistant resin paste and semiconducto r device using them and method for

manufacture thereof” available at http://www.patentstorm.us /patents/7061081/claims.html (accessed August 20, 2009)

Hoechst Aktiengesellschaft, 1999, “Process fo r purifying inert gases: United States

Patent 5871563” available at http://www.freepaten tsonline.com/5871563.html (accessed August 20, 2009)

Humco, 2007. Humco Holding Group, Inc. “Pat ent title: Antifungal Treatment of Nails” 2007. Available at http://www.faqs.o rg/patents/app/20090092576 (accessed April 4, 2009)

LONZA AG, 1969, “Process for the producti on of methacrylic acid from –hydroxy isobutyric acid” available at http://www.wikipatents.com/gb/1080473.html (accessed August 20, 2009

Mochizuki, 2000. S. Mochizuki, R. L. Smith, Jr., and H. Inomata “Supercritical carbon

dioxide extraction of alkali metals us ing a fluorinated anion as a carrier”,

Chemical Communication. 2000, 1381-1382. Abt Associates currently only has

the abstract.

Multicore Solders Limited, 1990, “Flux composition: United States Patent

4940498” available at http://www.freepatentsonline.com/4940498.html (accessed August 20, 2009

### Abt Associates, Inc.

September 3, 2009 22 Novolyte Technologies, 2009. Pers onal Communication between Joe Valcho of Novolyte Technologies and Eastern Research Group. June 2009.

HSDB, 2009. National Institute of Health, Unit ed States National Library of Medicine,

Hazardous Substance Data Bank. http://toxnet.nlm.nih.gov/cgibin/sis/htmlgen?HSDB (accessed August 21, 2009)

Schiller and Gmehling, 1992. Martin Schill er and Jurgen Gmehling “Measurement of Activity Coefficients at Infinite Di lution using Gas-Liquid Chromatography. 4 Results for Alkylene Glycol Dialky l Ethers as Stationary Phases” Journal of Chemical Engineering. 1992, 37, 503-8. Abt Associates currently only has the

abstract.

Score Card, 2005. Score Card: The Polluti on Information Website. Available at www.scorecard.org (accessed August 21, 2009)

SRI, 2006. “Printing Inks” SRI Specialty Chemicals Program. Nov. 2006. vol 14.

Unilever, 2007 “US Patent 7297674 - Gel laundr y detergent composition” available at http://www.patentstorm.us /patents/7297674/claims.html (accessed August 21, 2009)

Union Oil Company of Califor nia, 1972. “Preparation of ar omatic acids: United States

Patent 3700729” available at http://www.freepatentsonline.com/3700729.html (accessed August 21, 2009)

US Census Bureau, 2002. “Polish and other sa nitation good manufacturi ng” available at http://factfinder.census.gov/servlet/ PQRTable?_bm=y&-ds_name=EC0200SL1&- MFG=325612&-ib_code=31 (accessed August 21, 2009)

USDA, 2000. Untied States Department of Agriculture, Forest Service “Industry

Review: Semiannual Patents Review July-December 1999” 2000. Available at http://www.fpl.fs.fed.us/documnts/pdf2000/sykes00a.pdf (accessed April 4, 2009)

US Patent 4871109, “US Patent 4871109 - Va por phase soldering using certain perfluorinated polye thers” available at http://www.patentstorm.us/p atents/4871109/description.html (accessed August 21, 2009) Wagner, 1998. “Wagner Brake: MSDS-DOT 4 Brake Fluid” http://www.merlesauto.com/Admin/msds/DOT4.pdf (accessed August 21, 2009)

### Abt Associates, Inc.

September 3, 2009 23 Appendix A: List of 2006 IUR Consumer and Commercial Use Categories

Table A-1 below contains the list of 2006 IUR Consumer and Commercial Use Categories. Beginning 2006, sites manuf acturing more than 300,000 pounds of a chemical during the reporting year are required to provide processing and use information and select from one of these categories.

Table A-1: 2006 IUR Consumer and Commercial Use Categories

Consumer and Commercial Use Categories

1. Adhesives and sealants 2. Agricultural produ cts (non-pesticidal) 3. Artists' supplies 4. Automotive care products

5. Electrical and el ectronic products 6. Fabrics, textiles and apparel 7. Glass and ceramic products 8. Lawn and garden products (non-pesticidal) 9. Leather products 10. Lubricants, greases and fuel additives 11. Metal products 12. Paints and coatings 13. Paper products 14. Photographic supplies 15. Polishes and sanitation goods 16. Rubber and plastic products 17. Soaps and detergents 18. Transportation products

19. Wood and wood furniture

20. Other 21. Not readily obtainable