Issue 2, 2017

Synthesis of a novel polyester building block from pentoses by tin-containing silicates

Abstract

We report here the direct formation of the new chemical product trans-2,5-dihydroxy-3-pentenoic acid methyl ester from pentoses using tin-containing silicates as catalysts. The product is formed under alkali-free conditions in methanol at temperatures in the range 140–180 °C. The highest yields are found using Sn-Beta as the catalyst. Under optimised conditions, a yield of 33% is achieved. Purified trans-2,5-dihydroxy-3-pentenoic acid methyl ester was used for co-polymerisation studies with ethyl 6-hydroxyhexanoate using Candida antarctica lipase B as the catalyst. The co-polymerisation yields a product containing functional groups originating from trans-2,5-dihydroxy-3-pentenoic acid methyl ester in the polyester backbone. The reactivity of the incorporated olefin and hydroxyl moieties was investigated using trifluoroacetic anhydride and thiol–ene chemistry, thus illustrating the potential for functionalising the new co-polymers.

Graphical abstract: Synthesis of a novel polyester building block from pentoses by tin-containing silicates

Supplementary files

Article information

Article type
Paper
Submitted
12 nov 2016
Accepted
28 nov 2016
First published
04 jan 2017
This article is Open Access
Creative Commons BY license

RSC Adv., 2017,7, 985-996

Synthesis of a novel polyester building block from pentoses by tin-containing silicates

S. G. Elliot, C. Andersen, S. Tolborg, S. Meier, I. Sádaba, A. E. Daugaard and E. Taarning, RSC Adv., 2017, 7, 985 DOI: 10.1039/C6RA26708D

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