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

• Published in: RSC Advances
• Main Authors: Elliot, Samuel Gilbert, Andersen, Christian, Tolborg, Søren, Meier, Sebastian, Sadaba, I., Daugaard, Anders Egede, Taarning, E.
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2017
• Subjects: antartic*
• 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

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.