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Issue 12, 2016
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Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose

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Abstract

A new route for the selective synthesis of renewable 1,3-cyclopentanediol was developed by the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone followed by hydrogenation. The presence of a small amount of base catalysts is beneficial for the aqueous phase rearrangement of furfuryl alcohol to 4-hydroxycyclopent-2-enone. Such a promotion effect of base catalysts can be rationalized by restraining the generation of levulinic acid which may catalyze the polymerization of furfuryl alcohol. In the hydrogenation of 4-hydroxycyclopent-2-enone to 1,3-cyclopentanediol, an evident solvent effect was noticed. Higher carbon yields of 1,3-cyclopentanediol were obtained when tetrahydrofuran was used as the solvent. In the large scale tests with high initial concentrations of feedstocks, a high overall carbon yield (72.0%) of 1,3-cyclopentanediol was achieved over cheap catalysts (MgAl-HT and RANEY® Ni). As a potential application, 1,3-cyclopentanediol as obtained was successfully used as a monomer in the synthesis of polyurethane.

Graphical abstract: Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose

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Publication details

The article was received on 04 Feb 2016, accepted on 14 Mar 2016 and first published on 14 Mar 2016


Article type: Paper
DOI: 10.1039/C6GC00341A
Citation: Green Chem., 2016,18, 3607-3613
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    Industrially scalable and cost-effective synthesis of 1,3-cyclopentanediol with furfuryl alcohol from lignocellulose

    G. Li, N. Li, M. Zheng, S. Li, A. Wang, Y. Cong, X. Wang and T. Zhang, Green Chem., 2016, 18, 3607
    DOI: 10.1039/C6GC00341A

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