Selective oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran over intercalated vanadium phosphate oxides

被引:65
作者
Grasset, Fabien L. [1 ,2 ]
Katryniok, Benjamin [2 ,3 ]
Paul, Sebastien [2 ,3 ]
Nardello-Rataj, Veronique [1 ,4 ,5 ]
Pera-Titus, Marc [6 ]
Clacens, Jean-Marc [6 ]
De Campo, Floryan [6 ]
Dumeignil, Franck [1 ,2 ,5 ,7 ]
机构
[1] Univ Lille Nord France, F-59000 Lille, France
[2] Univ Lille 1, Ctr Hyperfrequences & Semicond, CNRS, Unite Catalyse & Chim Solide,UMR 8181, F-59655 Villeneuve Dascq, France
[3] Ecole Cent Lille, UCCS, CNRS, UMR 8181, F-59651 Villeneuve Dascq, France
[4] Equipe Accueil Chim Mol & Formulat EA CMF 4478, F-59652 Villeneuve Dascq, France
[5] Univ Lille 1, F-59650 Villeneuve Dascq, France
[6] UMI 3464 CNRS Rhodia China, Ecoefficient Prod & Proc Lab E2P2L, Shanghai 201108, Peoples R China
[7] Inst Univ France, F-75005 Paris, France
关键词
AEROBIC OXIDATION; CATALYSTS; BIOMASS; DERIVATIVES; ACID;
D O I
10.1039/c3ra41890a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The selective oxidation of 5-hydroxymethylfurfural (5-HMF) to 2,5-diformylfuran (DFF) was studied over vanadium phosphate oxide (VPO)-based heterogeneous catalysts in the liquid phase. The selectivity to DFF was highly increased when using intercalated vanadium phosphate oxides under mild conditions (1 atm of oxygen, 110 degrees C) in an aromatic solvent. We found that the length of the intercalated ammonium alkyl chain had no clear influence on the catalytic performances, and a maximum yield of 83% could be achieved over C14VOPO4 and C14VOHPO4 after 6 h of reaction. Recycling of the catalyst was successfully performed, and we further obtained some insights in the reaction pathway: while the desired oxidation reaction indeed proceeded over the catalyst, the formation of by-products was linked to the presence of free radicals in solution.
引用
收藏
页码:9942 / 9948
页数:7
相关论文
共 34 条
[1]   Efficient oxidation of 5-hydroxymethylfurfural to 2,5-diformylfuran using Mn(III)-salen catalysts [J].
Amarasekara, Ananda S. ;
Green, Dalkeith ;
McMillan, Erinn .
CATALYSIS COMMUNICATIONS, 2008, 9 (02) :286-288
[2]   Selective oxidation of 5-hydroxymethyl-2-furaldehyde to furan-2,5-dicarboxaldehyde by catalytic systems based on vanadyl phosphate [J].
Carlini, C ;
Patrono, P ;
Galletti, AMR ;
Sbrana, G ;
Zima, V .
APPLIED CATALYSIS A-GENERAL, 2005, 289 (02) :197-204
[3]   VANADYL PHOSPHATE DIHYDRATE, A SOLID ACID - THE ROLE OF WATER IN VOPO4.2H2O AND ITS SODIUM DERIVATIVES NAX(VIVXVV1-XO)PO4.(2-X)H2O [J].
CASAN, N ;
AMOROS, P ;
IBANEZ, R ;
MARTINEZTAMAYO, E ;
BELTRANPORTER, A ;
BELTRANPORTER, D .
JOURNAL OF INCLUSION PHENOMENA, 1988, 6 (02) :193-211
[4]   Biomass into chemicals: One pot-base free oxidative esterification of 5-hydroxymethyl-2-furfural into 2,5-dimethylfuroate with gold on nanoparticulated ceria [J].
Casanova, O. ;
Iborra, S. ;
Corma, A. .
JOURNAL OF CATALYSIS, 2009, 265 (01) :109-116
[5]   Chemical routes for the transformation of biomass into chemicals [J].
Corma, Avelino ;
Iborra, Sara ;
Velty, Alexandra .
CHEMICAL REVIEWS, 2007, 107 (06) :2411-2502
[6]  
Datta A, 2002, P INDIAN AS-CHEM SCI, V114, P379
[7]   Novel transformations amongst mesostructured VPO phases synthesized through surfactant assisted organization from an exfoliated solution of VOPO4•2H2O [J].
Datta, Arunabha ;
Sakthivel, S. ;
Kaur, Maninder ;
Venezia, Anna Maria ;
Pantaleo, Giuseppe ;
Longo, Alessandro .
MICROPOROUS AND MESOPOROUS MATERIALS, 2010, 128 (1-3) :213-222
[8]   Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts [J].
Davis, Sara E. ;
Houk, Levi R. ;
Tamargo, Erin C. ;
Datye, Abhaya K. ;
Davis, Robert J. .
CATALYSIS TODAY, 2011, 160 (01) :55-60
[9]   Structure in vitro activity relationships of pentamidine analogues and dication-substituted bis-benzimidazoles as new antifungal agents [J].
Del Poeta, M ;
Schell, WA ;
Dykstra, CC ;
Jones, S ;
Tidwell, RR ;
Czarny, A ;
Bajic, M ;
Bajic, M ;
Kumar, A ;
Boykin, D ;
Perfect, JR .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1998, 42 (10) :2495-2502
[10]   Synthesis of a novel mesoporous VPO compound [J].
Doi, T ;
Miyake, T .
CHEMICAL COMMUNICATIONS, 1996, (14) :1635-1636