Number

264-EN

Section

General Section

Use

Abstract

Cyclopentyl methyl ether (CPME) can be used as substitute for solvents like tetrahydrofuran (THF), 2-methyl tetrahydrofuran (MeTHF), methyl tert butyl ether (MTBE) or 1,4 dioxane, that may generate high risks for safety and are also classified as hazardous to health.

Substituted substances

Alternative Substances

Reliability of information

Internet information: data are from an internet document and only a basic and partial evaluation could be performed

Reason substitution

CMR
ED

Hazard Assessment

Substances to be substituted: Tetrahydrofuran is possibly carcinogenic to humans (Group 2B), according to the IARC Monographs. It fulfils the criteria to be listed in the Substance Database according to SUBSPORTplus Screening Criteria (SDSC). 1,4-Dioxane is a Substance of very high concern and is included on the REACH candidate list for authorization, according to Article 59 of Regulation (EG) No. 1907/2006. (REACH Regulation). tert-Butyl methyl ether has evidence of endocrine disrupting activity in at least one species using intact animals, according to EU database on endocrine disruptors. It fulfils the criteria to be listed in the Substance Database according to SUBSPORTplus Screening Criteria (SDSC). Tetrahydro-2-methylfuran is not listed in the SUBSPORTplus Database and has no harmonised classification according to Annex VI of Regulation (EC) No 1272/2008 (CLP Regulation). The MSDS from the producer and the presentation brochure (see Further information) classify cyclopentyl methyl ether (CPME) as highly flammable, harmful if swallowed and causing eye and skin irritation. It states that CPME is more stable to forming explosive peroxides than dioxane, tetrahydrofuran (THF) and even 2-methyl tetrahydrofuran (MeTHF). Alternative substances: Butylhydroxytoluene (BHT) that is used as stabilising additive (both for the alternative and the substituted solvents). This substance has endocrine disrupting properties, according to SIN List. Cyclopentyl methyl ether is not listed in the SUBSPORTplus Database and has no harmonised classification according to Annex VI of Regulation (EC) No 1272/2008 (CLP Regulation).

Description of Substitution

Some of the solvents that are used a lot in different sectors have properties that make them very hazardous. Tetrahydrofuran (THF) and 1,4 dioxane may generate hazardous levels of explosive peroxides. Methyl tert butyl ether (MTBE) is endocrine disruptor (SIN List), endocrine disruptor category 1 (EU EDC database) as listed in the Substance Database according to SUBSPORTplus Screening Criteria (SDSC). According to the producer cyclopentyl methyl ether (CPME) can be an alternative that is more stable than THF or even 2MeTHF, if 50 ppm butylhydroxytoluene (BHT) are added. BHTis also used as additive for the initial solvents. CPME is less likely to form explosive peroxides and the producer states it has other advantages: -it provides better yields and higher selectivity then THF in organo-metallic reactions; -can be more easily dried then THF and 2MeTHF; -has a lower miscibility in water therefore it can be separated and recovered easier, reducing wastes; -has a lower boiling point (106⁰C) than THF and 2MeTHF, allowing higher reaction temperatures. MeTHF can also be a substitute for THF. It has the same advantages as CPME and it can be obtained from renewable sources like corncobs and bagasse (fibrous waste from sugar cane processing).

Case/substitution evaluation

The main advantage of the alternative is that it can substitute solvents that may generate explosion due to their instability under the conditions of use. It may also substitute solvents that do not have this hazard (e.g. MTPB) but are flammable and are hazardous to health.

State of implementation

In use

Availability ofAlternative

Alternative available on the market.

Producer/Provider

http://www.sigmaaldrich.com/

Type of information supplier

Producer / distributor

Contact

http://www.sigmaaldrich.com/

Type of publication and availability

Brochure freely available on internet

Publication source: author, company, institute, year

The presentation is based on the brochure 'Green Chemistry Supporting the Advancement of Chemistry through Sound Environmental, Social and Fiscal Responsibilities' published by the producer Sigma-Aldrich on its website, in 2007. Update 2015: Greener Solvent Alternatives Supporting the Advancement of Chemistry through Sound Environmental, Social & Fiscal Responsibilities https://www.sigmaaldrich.com/insite_greener_solvent_alternatives

Date, reviewed

November 26, 2021