Synthesis of a novel polyester building block from pentoses by tin-containing silicates
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 ar...
| Published in: | RSC Advances |
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| Main Authors: | , , , , , , |
| Format: | Article in Journal/Newspaper |
| Language: | English |
| Published: |
2017
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| Subjects: | |
| Online Access: | https://orbit.dtu.dk/en/publications/6240e02c-5098-4f27-8f52-c1db3def1126 https://doi.org/10.1039/c6ra26708d https://backend.orbit.dtu.dk/ws/files/128435051/c6ra26708d.pdf |
| Summary: | 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. |
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