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

TY - JOUR

T1 - 2,2,5,5-Tetramethyltetrahydrofuran (TMTHF)

T2 - A non-polar, non-peroxide forming ether replacement for hazardous hydrocarbon solvents

AU - Byrne, Fergal

AU - Forier, Bart

AU - Bossaert, Greet

AU - Hoebers, Charly

AU - Farmer, Thomas J.

AU - Clark, James H.

AU - Hunt, Andrew J.

N1 - © 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.

PY - 2017/8/7

Y1 - 2017/8/7

N2 - 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.

AB - 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.

KW - Bio-based solvents

KW - bio-based chemicals

KW - Alternative solvents

KW - polymerisation

KW - clean synthesis

KW - safer solvents

UR - http://www.scopus.com/inward/record.url?scp=85026906722&partnerID=8YFLogxK

U2 - 10.1039/c7gc01392b

DO - 10.1039/c7gc01392b

M3 - Article

AN - SCOPUS:85026906722

SN - 1463-9262

VL - 19

SP - 3671

EP - 3678

JO - Green Chemistry

JF - Green Chemistry

IS - 15

ER -