Diols are a family of monomers which are widely used in the polymer industry. Currently, 1,3-cyclopentanediol is usually produced with cyclopentadiene from non-renewable energy resources. Moreover, some environmental unfriendly reagents are inevitably used in this process (such as diborane, halogenated agents, peroxide reagents, etc.). In this work, a new route was developed for the synthesis of 1,3-cyclopentanediol by the aqueous phase rearrangement of furfuryl alcohol and following hydrogenation (see Scheme 1). Under the optimum condition, a high carbon yield (up to 82.7%) of 4-hydroxycyclopent-2-enone was obtained over MgAl-HT catalyst with water as the only solvent. In addition, the promotion effect of sodium hydroxide is not unique. The presence of other often used base catalysts (such as Na2CO3, CaO, MgO, MgAl-hydrotalcite (MgAl-HT) and CeO2) is also favorable for this reaction. Furthermore, it was also noticed that there is a significant solvent effect in the liquid phase hydrogenation of 4-hydroxycyclopent-2-enone to 1,3-cyclopentanediol. When tetrahydrofuran was used as the solvent, high carbon yield of 1,3-cyclopentanediol was obtained over the Ru/C (94.7%) and Raney Ni (90.9%) catalysts. In summary, 1,3-cyclopentanediol was synthesized at high overall yield (78.3%) by a two-step route with furfuryl alcohol derived from lignocellulose. To the best of our knowledge, this is the first report about the selective synthesis of cyclic diol with lignocellusic platform chemical.

Cost-effective synthesis of 1, 3-cyclopentanediol with furfuryl alcohol derived from lignocellulose

255th National Meeting (2018)

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