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Issue 5, 2017
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Production of 1,6-hexanediol from tetrahydropyran-2-methanol by dehydration–hydration and hydrogenation

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Abstract

In this work we present an alternate method for the conversion of tetrahydropyran-2-methanol (THP2M), a cellulose-derived renewable building block, to 1,6-hexanediol (1,6-HDO). Our method is composed of three consecutive steps that either use relatively inexpensive catalysts or no catalyst at all. First, THP2M is catalytically dehydrated to 2,3,4,5-tetrahydrooxepine (THO) in up to 40% yield. THO is then hydrated to 2-oxepanol (OXL) and 6-hydroxyhexanal (6HDHX) with a combined yield of 85% in the absence of a catalyst. OXL and 6HDHX are then quantitatively hydrogenated to 1,6-HDO over a commercially available Ni/C or Ru/C catalyst. Various silicoaluminates were screened for the first acid-catalyzed reaction, and it was found that K-BEA shows the highest THO yield (40% over fresh catalyst, 20% after 25 h on stream). An overall 1,6-HDO yield of 34% from THP2M was obtained.

Graphical abstract: Production of 1,6-hexanediol from tetrahydropyran-2-methanol by dehydration–hydration and hydrogenation

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Supplementary files

Article information


Submitted
28 Dec 2016
Accepted
02 Feb 2017
First published
06 Feb 2017

Green Chem., 2017,19, 1390-1398
Article type
Paper

Production of 1,6-hexanediol from tetrahydropyran-2-methanol by dehydration–hydration and hydrogenation

S. P. Burt, K. J. Barnett, D. J. McClelland, P. Wolf, J. A. Dumesic, G. W. Huber and I. Hermans, Green Chem., 2017, 19, 1390
DOI: 10.1039/C6GC03606F

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