Microwave-induced base-catalyzed synthesis of methyl levulinate, a further improvement in dimethyl carbonate-mediated valorization of levulinic acid

被引:5
作者
Szabo, Yvette [1 ,2 ]
Kiss, Marton Attila [1 ]
Konya, Zoltan [1 ,3 ,4 ]
Kukovecz, Akos [3 ]
Palinko, Istvan [1 ,2 ]
Sipos, Pal [1 ,2 ,5 ]
Frank, Eva [1 ]
Szabados, Marton [1 ,2 ]
机构
[1] Univ Szeged, Dept Organ Chem, Dom Ter 8, H-6720 Szeged, Hungary
[2] Univ Szeged, Inst Chem, Interdisciplinary Excellence Ctr, Mat & Solut Struct Res Grp, Arad Vertanuk Tere 1, H-6720 Szeged, Hungary
[3] Univ Szeged, Dept Appl & Environm Chem, Rerrich B Ter 1, H-6720 Szeged, Hungary
[4] MTA SZTE React Kinet & Surface Chem Res Grp, Rerrich B Ter 1, H-6720 Szeged, Hungary
[5] Univ Szeged, Dept Inorgan & Analyt Chem, Dom Ter 7, H-6720 Szeged, Hungary
关键词
Microwave irradiation; Dimethyl carbonate; Levulinic acid; Metal levulinates; Tripotassium phosphate; ETHYL LEVULINATE; BIODIESEL PRODUCTION; O-METHYLATION; CHEMISTRY; EFFICIENT; METHANOL;
D O I
10.1016/j.apcata.2022.119020
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
We report base-catalyzed upgrading of bio-based levulinic acid to methyl levulinate fuel additive with the assistance of microwave (MW) irradiation. During the reactions, formation of crystalline sodium, potassium, rubidium levulinate intermediates occurred. The methylation potential of dimethyl carbonate was found to be excellent at 120 degrees C under MW conditions; moreover, alkylation could also occur at the boiling point (similar to 90 degrees C) of solvent. Precipitation of levulinate salts could be reduced by addition of co-solvents, and thus yields of methyl levulinate increased to over 90 %. The detailed investigation of effects of MW-assisted reaction revealed the accelerated formation of metal levulinates and the behavior of levulinate salts, base catalysts as "molecular radiators". This allows us to focus on replacement of generally used K2CO3 catalyst (showing MW-enhanced decomposition though CO2 liberation). Several inorganic bases were tested and K3PO4 proved to be the best green and economically friendly alternative with higher reusability potential.
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页数:9
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[1]   Insights into the Synthesis of Ethyl Levulinate under Microwave and Nonmicrowave Heating Conditions [J].
Ahmad, Ejaz ;
Alam, Md Imteyaz ;
Pant, K. K. ;
Haider, M. Ali .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2019, 58 (35) :16055-16064
[2]   Microwave-assisted synthesis of levulinic acid from low-cost, sustainable feedstocks using organic acids as green catalysts [J].
Aliko, Kinana ;
Doudin, Khalid ;
Osatiashtiani, Amin ;
Wang, Jiawei ;
Topham, Paul D. ;
Theodosiou, Eirini .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2020, 95 (08) :2110-2119
[3]  
Burton P.D., 2020, ANTIVIR RES, DOI [10.2172/1634888, DOI 10.2172/1634888]
[4]   Upgrading of Levulinic Acid with Dimethylcarbonate as Solvent/Reagent [J].
Caretto, Alessio ;
Perosa, Alvise .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (08) :989-994
[5]   Solid Mixed-Metal-Oxide Catalysts for Biodiesel Production: A Review [J].
Chang, Fei ;
Zhou, Quan ;
Pan, Hu ;
Liu, Xiao-Fang ;
Zhang, Heng ;
Xue, Wei ;
Yang, Song .
ENERGY TECHNOLOGY, 2014, 2 (11) :865-873
[6]  
Chatterjee C, 2015, GREEN CHEM, V17, P40, DOI [10.1039/C4GC01062K, 10.1039/c4gc01062k]
[7]   Properties and Performance of Levulinate Esters as Diesel Blend Components [J].
Christensen, Earl ;
Williams, Aaron ;
Paul, Stephen ;
Burton, Steve ;
McCormick, Robert L. .
ENERGY & FUELS, 2011, 25 (11) :5422-5428
[8]   Microwaves in organic synthesis.: Thermal and non-thermal microwave effects [J].
de la Hoz, A ;
Díaz-Ortiz, A ;
Moreno, A .
CHEMICAL SOCIETY REVIEWS, 2005, 34 (02) :164-178
[9]   Synthesis and Applications of Alkyl Levulinates [J].
Demolis, Alexandre ;
Essayem, Nadine ;
Rataboul, Franck .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2014, 2 (06) :1338-1352
[10]   Microwave-assisted green synthesis of levulinate esters as biofuel precursors using calix[4]arene as an organocatalyst under solvent-free conditions [J].
Dias Castro, Gabriel Abranches ;
Fernandes, Sergio Antonio .
SUSTAINABLE ENERGY & FUELS, 2021, 5 (01) :108-111