2, 2, 5, 5-Tetramethyltetrahydrofuran (TMTHF): a non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents. Issue 15 (11th July 2017)

• Record Type: Journal Article
• Authors: Byrne, Fergal; Forier, Bart; Bossaert, Greet; Hoebers, Charly; Farmer, Thomas J.; Clark, James H.; Hunt, Andrew J.
• Is Part Of: Green chemistry. Volume 19:Issue 15(2017)
• Page Start: 3671
• Page End: 3678
• Publication Date: 2017-07-11
• Subjects: Environmental chemistry -- Industrial applications -- Periodicals; Environmental management -- Periodicals; 660
• DOI: 10.1039/c7gc01392b
• Languages: English
• ISSNs: 1463-9262

Abstract

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. 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.