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Catalytic dimerization of bio-based 5-methylfurfuryl alcohol to bis(5-methylfuran-2-yl) methane with a solid acidic nanohybrid

Author(s):

Duo Jin, Chengjiang Fang, Yuanzhong Li, Yuanhui Shi, Yan Liu, Hu Li* and Song Yang*  

Abstract:


Background: Liquid C8-C15 long-chain alkanes, as main components of jet fuels or diesel, can be synthetized from abundant and renewable biomass derivatives by extending the carbon-chain length via cascade C-C coupling over acidic catalysts and hydrodeoxygenation over metal particles.

Objective: This research aims to develop a carbon-increasing catalytic process through the dimerization of 5-methylfurfuryl alcohol to produce the C11 oxygenate bis(5-methylfuran-2-yl) methane.

Method: In this work, 5-methylfurfural, derivable from sugars, could be reduced to the expensive 5-methylfurfuryl alcohol over Cs2CO3 using an eco-friendly hydride polymethylhydrosiloxane. In the subsequent carbon-increasing process, a solid acidic nanocatalyst 3-chlorpyridine phosphotungstic acid (3-ClPYPW) was developed to be efficient for conversion of 5-methylfurfuryl alcohol to bis(5-methylfuran-2-yl) methane under mild reaction conditions.

Results: A good bis(5-methylfuran-2-yl) methane yield of 51.6% was obtained using dichloromethane as solvent at a low temperature of 70°C in 11 h. The solid nanocatalyst was able to be reused for at least four cycles without remarkable loss of catalytic activity. The kinetic study proved that the reaction is a first-order reaction with apparent activation energy (Ea) of 41.10 kJ mol-1, while the thermodynamic study certified that the reaction is non-spontaneous and endothermic.

Conclusion: A novel catalytic pathway for the synthesis of BMFM (C11 oxygenate) by one-pot process was successfully developed over a solid acidic nanocatalysts 3-ClPYPW.

Keywords:

Nanocatalyst, inorganic-organic hybrid, heterogeneous catalysis, biofuel, biomass-derived furanic compounds, fuel precursors

Affiliation:

State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025, State Key Laboratory Breeding Base of Green Pesticide & Agricultural Bioengineering, Key Laboratory of Green Pesticide & Agricultural Bioengineering, Ministry of Education, State-Local Joint Laboratory for Comprehensive Utilization of Biomass, Center for R&D of Fine Chemicals, Guizhou University, Guiyang, Guizhou 550025



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