Sc(OTf)3: An efficient homogeneous catalyst for microwave-assisted transfer hydrogenation of ethyl levulinate to γ-valerolactone under mild conditions

被引:11
作者
Li, Fukun [1 ,2 ]
Yang, Ronghe [2 ]
Du, Ziting [2 ]
Dai, Jinhang [2 ]
Wang, Xingmin [2 ]
Li, Ning [2 ]
Zhang, Jie [2 ]
Zhang, Xianming [2 ]
Liu, Yunqi [1 ,3 ]
Gong, Haifeng [1 ]
Yin, Hong [1 ]
Cai, Zhenping [4 ]
机构
[1] Chongqing Technol & Business Univ, Engn Res Ctr Waste Oil Recovery Technol & Equipmen, Minist Educ, Chongqing 400067, Peoples R China
[2] Chongqing Technol & Business Univ, Coll Environm & Resources, Chongqing 400067, Peoples R China
[3] China Univ Petr East China, State Key Lab Heavy Oil Proc, Qingdao 266580, Peoples R China
[4] Quanzhou Normal Univ, Coll Chem Engn & Mat Sci, Quanzhou 362000, Peoples R China
基金
中国博士后科学基金; 中国国家自然科学基金;
关键词
Transfer hydrogenation; Ethyl levulinate; -valerolactone; Sc(OTf)3; Microwave heating; PONNDORF-VERLEY REDUCTION; LEWIS-ACID SITES; CARBONYL-COMPOUNDS; METHYL LEVULINATE; BIOMASS; CONVERSION; ALDEHYDES; KETONES; TRANSFORMATION; CELLULOSE;
D O I
10.1016/j.mcat.2022.112863
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
gamma-Valerolactone (GVL) is considered as a versatile platform chemical obtained from biomass refinery. In this study, eco-friendly group III metal (Sc, Y, La) triflates were examined as homogeneous catalysts for microwave -assisted transfer hydrogenation of ethyl levulinate (EL) to GVL under mild conditions. Experimental results revealed that the selectivity of GVL has a positive relationship with the Lewis acidity of metal ion, which is related to effective charge density of the metal center (3.23, 2.81, 2.60 for Sc3+, Y3+, La3+, respectively). The stronger Lewis acidity of metal ion, the higher catalytic activity of MPV reduction. Among these catalysts, Sc (OTf)3 exhibited the best catalytic activity, achieving 98.4% EL conversion and 92.4% GVL yield at 140 degrees C in 3.0 h. Furthermore, Sc(OTf)3 showed high stability and recyclability for at least ten reaction cycles. In addition, a plausible reaction pathway and mechanism were proposed.
引用
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页数:8
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共 63 条
[1]   Surface properties vs activity of meso-ZrO2 catalyst in chemoselective Meerwein-Ponndorf-Verley reduction of citral: Effect of calcination temperature [J].
Akinnawo, Christianah Aarinola ;
Bingwa, Ndzondelelo ;
Meijboom, Reinout .
MICROPOROUS AND MESOPOROUS MATERIALS, 2021, 311
[2]   Simple method to synthesize high surface area magnesium oxide and its use as a heterogeneous base catalyst [J].
Bartley, Jonathan K. ;
Xu, Chunli ;
Lloyd, Rhys ;
Enache, Dan I. ;
Knight, David W. ;
Hutchings, Graham J. .
APPLIED CATALYSIS B-ENVIRONMENTAL, 2012, 128 :31-38
[3]   A Mild and Efficient Flow Procedure for the Transfer Hydrogenation of Ketones and Aldehydes using Hydrous Zirconia [J].
Battilocchio, Claudio ;
Hawkins, Joel M. ;
Ley, Steven V. .
ORGANIC LETTERS, 2013, 15 (09) :2278-2281
[4]   Homogeneous catalysis for the production of low-volume, high-value chemicals from biomass [J].
Bender, Trandon A. ;
Dabrowski, Jennifer A. ;
Gagne, Michel R. .
NATURE REVIEWS CHEMISTRY, 2018, 2 (05) :35-46
[5]   Trapped Intermediate of a Meerwein-Pondorf-Verley Reduction of Hydroxy Benzaldehyde to a Dialkoxide by Titanium Alkoxides [J].
Boyle, Timothy J. ;
Guerrero, Fernando ;
Alam, Todd M. ;
Dunnigan, Kaylee A. ;
Sears, Jeremiah M. ;
Wheeler, David R. .
INORGANIC CHEMISTRY, 2020, 59 (01) :880-890
[6]   Domino Reaction Catalyzed by Zeolites with BrOnsted and Lewis Acid Sites for the Production of -Valerolactone from Furfural [J].
Bui, Linh ;
Luo, Helen ;
Gunther, William R. ;
Roman-Leshkov, Yuriy .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :8022-8025
[7]   Continuous flow transfer hydrogenation of biomass derived methyl levulinate over Zr containing zeolites: Insights into the role of the catalyst acidity [J].
Cabanillas, Matilde ;
Franco, Ana ;
Lazaro, Noelia ;
Balu, Alina M. ;
Luque, Rafael ;
Pineda, Antonio .
MOLECULAR CATALYSIS, 2019, 477
[8]   Catalytic Meerwein-Pondorf-Verley reduction by simple aluminum complexes [J].
Campbell, EJ ;
Zhou, HY ;
Nguyen, ST .
ORGANIC LETTERS, 2001, 3 (15) :2391-2393
[9]   In-situ synthesis of single-atom Ir by utilizing metal-organic frameworks: An acid-resistant catalyst for hydrogenation of levulinic acid to γ-valerolactone [J].
Cao, Wenxiu ;
Lin, Lu ;
Qi, Haifeng ;
He, Qian ;
Wu, Zhijie ;
Wang, Aiqin ;
Luo, Wenhao ;
Zhang, Tao .
JOURNAL OF CATALYSIS, 2019, 373 (161-172) :161-172
[10]   Liquid-phase catalytic transfer hydrogenation and cyclization of levulinic acid and its esters to γ-valerolactone over metal oxide catalysts [J].
Chia, Mei ;
Dumesic, James A. .
CHEMICAL COMMUNICATIONS, 2011, 47 (44) :12233-12235