MOF-catalyzed hydroxyalkylation-alkylation reaction for the controlled synthesis of furan oligomers

被引:10
作者
Atayde Jr, Eduardo C. [1 ,2 ,3 ]
Matsagar, Babasaheb M. [3 ]
Wang, Yu-Cheng [3 ]
Wu, Kevin C. -W. [1 ,3 ,4 ]
机构
[1] Acad Sinica, Mol Sci & Technol Program, Taiwan Int Grad Program, 128,Sec 2,Acad Rd, Taipei 11529, Taiwan
[2] Natl Tsing Hua Univ, Dept Chem, 101,Sec 2,Kuang Fu Rd, Hsinchu 30013, Taiwan
[3] Natl Taiwan Univ, Dept Chem Engn, 1,Sec 2,Roosevelt Rd, Taipei 10617, Taiwan
[4] Yuan Ze Univ, Dept Chem Engn & Mat Sci, Taoyuan, Taiwan
关键词
Biomass; Catalysis; Furan oligomers; Hydroxylalkylation/alkylation reactions; Metal-organic frameworks; DIESEL-RANGE ALKANES; HIGH-QUALITY DIESEL; SELECTIVE PRODUCTION; FUEL PRECURSORS; ACID CATALYSTS; 2-METHYLFURAN; CARBON; HYDRODEOXYGENATION; CONDENSATION; DERIVATIVES;
D O I
10.1016/j.apcata.2023.119492
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
Hydroxyalkylation-alkylation (HAA) reaction is a type of C-C coupling technique utilized in the production of furan oligomers, which are potential biofuel precursors. In this study, we present the first application of an acidic MOF, Sulfated MOF-808, in catalyzing the HAA reactions of a series of furan oligomers with high yield and selectivity. Specifically, we focused on the optimization of the HAA between 5-methylfurfural (5-MFUR) and 2methylfuran (2-MF) by varying different reaction conditions, which afforded a quantitative yield reaching 97% while preventing the self-condensation of 2-MF. The catalyst was also found to be recyclable and can be reused without significant loss in its activity. Lastly, we extended the substrate scope to include benzene-based electrophiles, thereby further proving the versatility of the Sulfated MOF-808 catalyst in the HAA reactions of a variety of starting materials.
引用
收藏
页数:9
相关论文
共 44 条
[1]   Nanocrystalline titania-based sulfonic acid (TiO2-Pr-SO3H) as a new, highly efficient, and recyclable solid acid catalyst for preparation of quinoxaline derivatives [J].
Atghia S.V. ;
Beigbaghlou S.S. .
Journal of Nanostructure in Chemistry, 2013, 3 (1)
[2]   Acid functionalized hydrochar as heterogeneous catalysts for solventless synthesis of biofuel precursors [J].
Chhabra, Tripti ;
Dwivedi, Prachi ;
Krishnan, Venkata .
GREEN CHEMISTRY, 2022, 24 (02) :898-910
[3]   Combined treatments for producing 5-hydroxymethylfurfural (HMF) from lignocellulosic biomass [J].
Chi Van Nguyen ;
Lewis, Daniel ;
Chen, Wen-Hwa ;
Huang, Hsin-Wu ;
ALOthman, Zeid Abdullah ;
Yamauchi, Yusuke ;
Wu, Kevin C. -W. .
CATALYSIS TODAY, 2016, 278 :344-349
[4]   High-Quality Diesel from Hexose- and Pentose-Derived Biomass Platform Molecules [J].
Corma, Avelino ;
de la Torre, Olalla ;
Renz, Michael .
CHEMSUSCHEM, 2011, 4 (11) :1574-1577
[5]   Production of High-Quality Diesel from Biomass Waste Products [J].
Corma, Avelino ;
de la Torre, Olalla ;
Renz, Michael ;
Villandier, Nicolas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (10) :2375-2378
[6]   A new triazine-thiophene based porous organic polymer as efficient catalyst for the synthesis of chromenes via multicomponent coupling and catalyst support for facile synthesis of HMF from carbohydrates [J].
Das, Sabuj Kanti ;
Chatterjee, Sauvik ;
Mondal, Sujan ;
Bhaumik, Asim .
MOLECULAR CATALYSIS, 2019, 475
[7]   Hydrodeoxygenation of Furylmethane Oxygenates to Jet and Diesel Range Fuels: Probing the Reaction Network with Supported Palladium Catalyst and Hafnium Triflate Promoter [J].
Dutta, Saikat ;
Saha, Basudeb .
ACS CATALYSIS, 2017, 7 (08) :5491-5499
[8]   Solventless C-C Coupling of Low Carbon Furanics to High Carbon Fuel Precursors Using an Improved Graphene Oxide Carbocatalyst [J].
Dutta, Saikat ;
Bohre, Ashish ;
Zheng, Weiqing ;
Jenness, Glen R. ;
Nunez, Marcel ;
Saha, Basudeb ;
Vlachos, Dionisios G. .
ACS CATALYSIS, 2017, 7 (06) :3905-3915
[9]   Effect of carboxylic acid of periodic mesoporous organosilicas on the fructose-to-5-hydroxymethylfurfural conversion in dimethylsulfoxide systems [J].
Dutta, Saikat ;
Kao, Hsien-Ming ;
Wu, Kevin C. -W. .
APL MATERIALS, 2014, 2 (11)
[10]   Water Adsorption in Porous Metal-Organic Frameworks and Related Materials [J].
Furukawa, Hiroyasu ;
Gandara, Felipe ;
Zhang, Yue-Biao ;
Jiang, Juncong ;
Queen, Wendy L. ;
Hudson, Matthew R. ;
Yaghi, Omar M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (11) :4369-4381