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Issue 15, 2020

Selective hydrogenation of aromatic furfurals into aliphatic tetrahydrofurfural derivatives

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Abstract

Tetrahydrofurfural (THFF) and 5-hydroxymethyltetrahydro-2-furaldehyde (5-HMTHFF) are important chemicals. Synthesis of THFF and 5-HMTHFF from the selective hydrogenation of furfural (FF) and 5-hydroxymethylfurfural (HMF) is highly desirable. However, it is a great challenge to hydrogenate furanyl rings while keeping C[double bond, length as m-dash]O intact. Herein, we found that Pd/LDH-MgAl-NO3 could efficiently catalyze the hydrogenation of FF to THFF and HMF to 5-HMTHFF in water. At near complete conversion of FF and HMF, the selectivities of THFF and 5-HMTHFF could reach 92.6% and 83.7%, respectively. A series of control experiments showed that both the LDH-MgAl-NO3 support and water solvent played an important role in the unusual performance of the catalytic system. The hydrogenation of the furanyl ring occurred on the surface of Pd. Water prohibited the hydrogenation of the C[double bond, length as m-dash]O group, and the special nature of LDH-MgAl-NO3 prevented hydrogenation of the C[double bond, length as m-dash]O group on the support by the hydrogen spillover. Thus, the furanyl ring was selectively hydrogenated, and high selectivity of the desired product was successfully achieved. As far as we know, efficient hydrogenation of FF to THFF or HMF to 5-HMTHFF has not been reported. This work opens the way to selectively hydrogenate the furanyl ring while keeping C[double bond, length as m-dash]O in the same molecule unchanged.

Graphical abstract: Selective hydrogenation of aromatic furfurals into aliphatic tetrahydrofurfural derivatives

Supplementary files

Article information


Submitted
08 May 2020
Accepted
02 Jul 2020
First published
03 Jul 2020

Green Chem., 2020,22, 4937-4942
Article type
Paper

Selective hydrogenation of aromatic furfurals into aliphatic tetrahydrofurfural derivatives

Y. Yang, Y. Wang, S. Li, X. Shen, B. Chen, H. Liu and B. Han, Green Chem., 2020, 22, 4937 DOI: 10.1039/D0GC01587C

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