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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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Publication details

The article was received on 28 Dec 2016, accepted on 02 Feb 2017 and first published on 06 Feb 2017


Article type: Paper
DOI: 10.1039/C6GC03606F
Citation: Green Chem., 2017,19, 1390-1398
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    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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