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

Samuel Gilbert Elliot, Christian Andersen, Søren Tolborg, Sebastian Meier, I. Sadaba, Anders Egede Daugaard, E. Taarning

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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 copolymerisation studies with ethyl 6-hydroxyhexanoate using Candida antartica Lipase B as the catalyst. The copolymersiation 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 chemisitry, thus illustrating the potential for functionalising the new co-polymers.
Original languageEnglish
JournalRSC Advances
Volume7
Pages (from-to)985–996
ISSN2046-2069
DOIs
Publication statusPublished - 2017

Bibliographical note

Open Access Article. Published on 04 January 2017. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

Cite this

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title = "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 copolymerisation studies with ethyl 6-hydroxyhexanoate using Candida antartica Lipase B as the catalyst. The copolymersiation 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 chemisitry, thus illustrating the potential for functionalising the new co-polymers.",
author = "Elliot, {Samuel Gilbert} and Christian Andersen and S{\o}ren Tolborg and Sebastian Meier and I. Sadaba and Daugaard, {Anders Egede} and E. Taarning",
note = "Open Access Article. Published on 04 January 2017. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.",
year = "2017",
doi = "10.1039/c6ra26708d",
language = "English",
volume = "7",
pages = "985–996",
journal = "R S C Advances",
issn = "2046-2069",
publisher = "RSC Publishing",

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Synthesis of a novel polyester building block from pentoses by tin-containing silicates. / Elliot, Samuel Gilbert; Andersen, Christian; Tolborg, Søren; Meier, Sebastian; Sadaba, I. ; Daugaard, Anders Egede; Taarning, E.

In: RSC Advances, Vol. 7, 2017, p. 985–996.

Research output: Contribution to journalJournal articleResearchpeer-review

TY - JOUR

T1 - Synthesis of a novel polyester building block from pentoses by tin-containing silicates

AU - Elliot, Samuel Gilbert

AU - Andersen, Christian

AU - Tolborg, Søren

AU - Meier, Sebastian

AU - Sadaba, I.

AU - Daugaard, Anders Egede

AU - Taarning, E.

N1 - Open Access Article. Published on 04 January 2017. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.

PY - 2017

Y1 - 2017

N2 - 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 copolymerisation studies with ethyl 6-hydroxyhexanoate using Candida antartica Lipase B as the catalyst. The copolymersiation 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 chemisitry, thus illustrating the potential for functionalising the new co-polymers.

AB - 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 copolymerisation studies with ethyl 6-hydroxyhexanoate using Candida antartica Lipase B as the catalyst. The copolymersiation 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 chemisitry, thus illustrating the potential for functionalising the new co-polymers.

U2 - 10.1039/c6ra26708d

DO - 10.1039/c6ra26708d

M3 - Journal article

VL - 7

SP - 985

EP - 996

JO - R S C Advances

JF - R S C Advances

SN - 2046-2069

ER -