DEHYDRATION AND CYCLIZATION OF ALPHA-, BETA-DIHYDROXY CARBONYL COMPOUNDS TO 2-SUBSTITUTED FURAN DERIVATIVES

    公开(公告)号:WO2019199570A1

    公开(公告)日:2019-10-17

    申请号:PCT/US2019/025785

    申请日:2019-04-04

    IPC分类号: C07D307/68

    摘要: Processes are disclosed for the synthesis of 2-substituted furan derivatives from a substrate having a carbonyl functional group (C=O), with hydroxy-substituted carbon atoms at alpha and beta positions, relative to the carbonyl functional group. In one embodiment, an alpha-, beta-dihydroxy carboxylate is dehydrated to form a dicarbonyl intermediate by transformation of the alpha-hydroxy group to a second carbonyl group and removal of the beta-hydroxy group. The dicarbonyl intermediate undergoes cyclization and dehydration to produce the 2-substituted furan derivative. Optionally, a further step of oxidation may be carried out, for example to convert a hydroxymethyl group, as a 5-substituted furan ring, to a carboxy group of 2,5-furan dicarboxylic acid.

    METHOD FOR PURIFYING AND REMOVING COLOR OF FDCA

    公开(公告)号:WO2019132663A1

    公开(公告)日:2019-07-04

    申请号:PCT/NL2018/050894

    申请日:2018-12-31

    IPC分类号: C07D307/68

    摘要: The invention is based on the finding that when conducting crystallization of FDCA at high temperatures, the formation of significant amounts of colored byproduct can be reduced or even avoided when the FDCA mixture is kept at temperatures above 100 °C for less than 15 minutes. This is achieved by conducting the crystallization process in a continuous reactor. Accordingly, the method comprises the steps of feeding a mixture comprising undissolved FDCA and a solvent to a reactor; and dissolving FDCA by superheating the mixture in the reactor to a temperature of at least 130 °C; and crystallizing FDCA by cooling the mixture in the reactor, wherein the reactor is a continuous reactor and the residence time in the reactor zone wherein the FDCA mixture has a temperature above 100 °C is less than 15 minutes.