Byrne, Fergal, Forier, Bart, Bossaert, Greet et al. (4 more authors) (2017) 2,2,5,5-Tetramethyltetrahydrofuran (TMTHF):A non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents. Green Chemistry. pp. 3671-3678. ISSN 1463-9262
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.
Metadata
Item Type: | Article |
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Authors/Creators: |
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Copyright, Publisher and Additional Information: | © 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. |
Keywords: | Bio-based solvents,bio-based chemicals,Alternative solvents,polymerisation,clean synthesis,safer solvents |
Dates: |
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Institution: | The University of York |
Academic Units: | The University of York > Faculty of Sciences (York) > Chemistry (York) |
Depositing User: | Pure (York) |
Date Deposited: | 05 Jul 2017 15:45 |
Last Modified: | 27 Nov 2024 00:30 |
Published Version: | https://doi.org/10.1039/c7gc01392b |
Status: | Published |
Refereed: | Yes |
Identification Number: | 10.1039/c7gc01392b |
Related URLs: | |
Open Archives Initiative ID (OAI ID): | oai:eprints.whiterose.ac.uk:118680 |