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2,2,5,5-Tetramethyltetrahydrofuran (TMTHF): A non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents

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JournalGreen Chemistry
DateAccepted/In press - 4 Jul 2017
DateE-pub ahead of print - 4 Jul 2017
DatePublished (current) - 7 Aug 2017
Issue number15
Volume19
Number of pages8
Pages (from-to)3671-3678
Early online date4/07/17
Original languageEnglish

Abstract

An inherently non-peroxide forming ether solvent, 2,2,5,5-tetramethyltetrahydrofuran (2,2,5,5-tetramethyloxolane), has been synthesized from readily available and potentially renewable feedstocks, and its solvation properties have been tested. Unlike traditional ethers, its absence of a proton at the alpha-position to the oxygen of the ether eliminates the potential to form hazardous peroxides. Additionally, this unusual structure leads to lower basicity compared with many traditional ethers, due to the concealment of the ethereal oxygen by four bulky methyl groups at the alpha-position. As such, this molecule exhibits similar solvent properties to common hydrocarbon solvents, particularly toluene. Its solvent properties have been proved by testing its performance in Fischer esterification, amidation and Grignard reactions. TMTHF's differences from traditional ethers is further demonstrated by its ability to produce high molecular weight radical-initiated polymers for use as pressure-sensitive adhesives.

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© The Royal Society of Chemistry 2017. This is an author-produced version of the published paper. Uploaded in accordance with the publisher’s self-archiving policy. Further copying may not be permitted; contact the publisher for details.

    Research areas

  • Bio-based solvents, bio-based chemicals, Alternative solvents, polymerisation, clean synthesis, safer solvents

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