Valorization of furfural using ruthenium (II) complexes containing phosphorus-nitrogen ligands under homogeneous transfer hydrogen condition

被引:10
作者
Parra-Melipan, Sebastian [1 ]
Lopez, Vicente [1 ]
Moya, Sergio A. [2 ]
Valdebenito, Gonzalo [1 ]
Aranda, Braulio [3 ]
Aguirre, Pedro [1 ]
机构
[1] Univ Chile, Fac Ciencias Quim & Farmaceut, Dept Quim Inorgan & Analit, Santiago, Chile
[2] Univ Santiago Chile, Fac Quim & Biol, Dept Ciencias Mat, Santiago, Chile
[3] Univ La Frontera, Fac Ingn & Ciencias, Dept Quim & Recursos Nat, Temuco, Chile
关键词
Ruthenium complexes; Hydrogenation furfural; phosphorus-nitrogen ligands; valorization of furfural; CATALYTIC-HYDROGENATION; PLATFORM MOLECULES; LIQUID ALKANES; FUEL ADDITIVES; BIOMASS; CONVERSION; CHEMICALS; METAL; PROTON; OLIGOMERIZATION;
D O I
10.1016/j.mcat.2021.111729
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
In this paper, we report the catalytic activity of a series of ruthenium (II) complexes containing phosphorus nitrogen bidentated (P-N) ligands in the hydrogenation of furfural via hydrogen transfer reaction using two hydrogen donor sources: 2-propanol in basic medium and formic acid under mild conditions. The results showed that all the ruthenium complexes studied are catalytically active in the hydrogenation of furfural by hydrogen transfer reaction; they showed 100% conversion with both hydrogen sources. However, selectivities towards the formation of furfuryl alcohol were better when formic acid was used. It was also found that the reaction studied in a basic medium competes with the Cannizzaro reaction, obtaining furfuryl alcohol and furoic acid in a 70/30 ratio; on the other hand, using formic acid as the hydrogen source yields furfuryl alcohol with 100% selectivity. Although formic acid can be used as a hydrogen source successfully. The optimal substrate/acid ratio was found to be 1:1, as a higher concentration of formic acid can cause catalyst decomposition. The yielded products, furfuryl alcohol and furoic acid, obtained from renewable sources, have multiple applications in the organic chemical industry, replacing or complementing similar fossil-derived products.
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页数:9
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共 54 条
[1]   Methoxycarbonylation of Styrene Using a New Type of Palladium Complexes Bearing P,N-donor Ligands as Catalysts [J].
Abarca, Gabriel ;
Brown, Kareen ;
Moya, Sergio A. ;
Bayon, J. Carles ;
Aguirre, Pedro A. .
CATALYSIS LETTERS, 2015, 145 (07) :1396-1402
[2]   Methoxycarbonylation of olefins catalyzed by palladium complexes bearing P,N-donor ligands [J].
Aguirre, Pedro A. ;
Lagos, Carolina A. ;
Moya, Sergio A. ;
Zuniga, Esar ;
Vera-Oyarce, Cristian ;
Sola, Eduardo ;
Peris, Gabriel ;
Carles Bayon, J. .
DALTON TRANSACTIONS, 2007, (46) :5419-5426
[3]   New palladium (II) complexes containing phosphine-nitrogen ligands and their use as catalysts in aminocarbonylation reaction [J].
Aranda, Braulio ;
Moya, Sergio A. ;
Vega, Andres ;
Valdebenito, Gonzalo ;
Ramirez-Lopez, Sofia ;
Aguirre, Pedro .
APPLIED ORGANOMETALLIC CHEMISTRY, 2019, 33 (04)
[4]   Conversion of Biomass into Chemicals over Metal Catalysts [J].
Besson, Michele ;
Gallezot, Pierre ;
Pinel, Catherine .
CHEMICAL REVIEWS, 2014, 114 (03) :1827-1870
[5]   Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing [J].
Carlos Serrano-Ruiz, Juan ;
Luque, Rafael ;
Sepulveda-Escribano, Antonio .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (11) :5266-5281
[6]   Complexes of osmium with the 2-[(diphenylphosphanyl)-methyl]-pyridine ligand [J].
Carlson, Brenden ;
Eichinger, Bruce E. ;
Kaminsky, Werner ;
Phelan, Gregory D. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2008, 112 (21) :7858-7865
[7]   P(CH2CH2Py)(n)Ph3-n (Py = 2-pyridyl; n = 1, 2, 3) as chelating and as binucleating ligands for palladium [J].
Casares, JA ;
Espinet, P ;
Soulantica, K ;
Pascual, I ;
Orpen, AG .
INORGANIC CHEMISTRY, 1997, 36 (23) :5251-5256
[8]   Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals [J].
Chheda, Juben N. ;
Huber, George W. ;
Dumesic, James A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) :7164-7183
[9]   An overview of dehydration, aldol-condensation and hydrogenation processes for production of liquid alkanes from biomass-derived carbohydrates [J].
Chheda, Juben N. ;
Dumesic, James A. .
CATALYSIS TODAY, 2007, 123 (1-4) :59-70
[10]   Green Chemistry, Biofuels, and Biorefinery [J].
Clark, James H. ;
Luque, Rafael ;
Matharu, Avtar S. .
ANNUAL REVIEW OF CHEMICAL AND BIOMOLECULAR ENGINEERING, VOL 3, 2012, 3 :183-207