One-Pot Efficient Synthesis of 3-Methylindole from Biomass-Derived Glycerol with Aniline by Highly Dispersible Nanosilver Catalyst

doi:10.11944/j.issn.1000-0518.2019.04.180265

Chinese Journal of Applied Chemistry ›› 2019, Vol. 36 ›› Issue (4): 465-473.DOI: 10.11944/j.issn.1000-0518.2019.04.180265

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One-Pot Efficient Synthesis of 3-Methylindole from Biomass-Derived Glycerol with Aniline by Highly Dispersible Nanosilver Catalyst

HAO Wenwen^a,ZHAO Dan^a,LI Yanchun^b,CHU Wenling^c,LÜ Chengwei^a,SHI Lei^a^*()

^aCollege of Chemistry and Chemical Engineering,Liaoning Normal University,Dalian,Liaoning 116029,China
^bInstitute of Theoretical Chemistry,Jilin University,Changchun 130021,China
^c State Key Laboratory of Catalysis,Dalian Institute of Chemical Physics,Chinese Academy of Sciences,Dalian,Liaoning 116023,China

Received:2018-08-15 Accepted:2018-10-23 Published:2019-04-01 Online:2019-04-02
Contact: SHI Lei
Supported by:
Supported by the National Natural Science Foundation of China(No.21576128, No.21604031, No.21403100)

Abstract

Abstract:

A highly dispersible nanosilver catalyst of ZnO modified Ag/SiO₂ was successfully applied to the one-pot efficient synthesis of 3-methylindole from aniline and biomass-derived glycerol for the first time. The catalyst exhibited an excellent catalytic performance. The investigations of Ag-based catalysts via X-ray diffraction(XRD), transmission electron microscopy(TEM), temperature programmed reduction of H₂(H₂-TPR), temperature programmed desorption(TPD) of NH₃ or CO₂, thermogravimetric(TG) analysis and inductively coupled plasma(ICP) emission spectroscopy indicate that ZnO can enhance the interaction between silver and the support and make Ag particles be firmly anchored on the support of SiO₂-ZnO. As a result, not only the dispersion of silver is increased obviously, but also the aggregation or sintering of silver nanoparticles is inhibited effectively. In addition, ZnO can also increase the acid and base sites of the Ag-based catalyst significantly, which is very beneficial to the hydrogenolysis of glycerol to 1,2-propanediol and promoted the synthesis of 3-methylindole greatly. The yield of 3-methylindole is up to 64% at the reaction time of 16 h and is only decreased by 4% after Ag/SiO₂-ZnO is reused four times. Furthermore, the synthesis mechanism of 3-methylindole from glycerol and aniline over Ag/SiO₂-ZnO catalyst was proposed, in which 1,2-propanediol is the intermediate to produce 3-methylindole.

Key words: ZnO, Ag/SiO₂, 3-methylindole, biomass-derived glycerol, catalytic performance

HAO Wenwen, ZHAO Dan, LI Yanchun, CHU Wenling, LÜ Chengwei, SHI Lei. One-Pot Efficient Synthesis of 3-Methylindole from Biomass-Derived Glycerol with Aniline by Highly Dispersible Nanosilver Catalyst[J]. Chinese Journal of Applied Chemistry, 2019, 36(4): 465-473.

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One-Pot Efficient Synthesis of 3-Methylindole from Biomass-Derived Glycerol with Aniline by Highly Dispersible Nanosilver Catalyst

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