Synthesis of 1,4:3,6-Dianhydrohexitols Diesters from the Palladium-Catalyzed Hydroesterification Reaction

被引:13
作者
Pruvost, Romain [1 ]
Boulanger, Jerome [2 ]
Leger, Bastien [2 ]
Ponchel, Anne [2 ]
Monflier, Eric [2 ]
Ibert, Mathias [3 ]
Mortreux, Andre [1 ]
Chenal, Thomas [1 ]
Sauthier, Mathieu [1 ]
机构
[1] Univ Lille 1, CNRS, UMR 8181, Unite Catalyse & Chim Solide,ENSCL, F-59650 Villeneuve Dascq, France
[2] Univ Artois, UMR 8181, Fac Sci Jean Perrin, F-62307 Lens, France
[3] Roquette Freres, F-62136 Lestrem, France
关键词
diester; hydroesterification; isosorbide; olefin; palladium; CARBON-MONOXIDE; ISOSORBIDE; ESTERIFICATION; ALKENES; 1,4/3,6-DIANHYDRO-D-GLUCITOL; METHOXYCARBONYLATION; CARBONYLATION; COMPLEXES; ALKYNES; ETHENE;
D O I
10.1002/cssc.201402584
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The hydroesterification of alpha olefins has been used to synthesize diesters from bio-based secondary diols: isosorbide, isomannide, and isoidide. The reaction was promoted by 0.2% palladium catalyst generated insitu from palladium acetate/triphenylphosphine/para-toluene sulfonic acid. Optimized reaction conditions allowed the selective synthesis of the diesters with high yields and the reaction conditions could be scaled up to the synthesis of hundred grams of diesters from isosorbide and 1-octene with solvent-free conditions.
引用
收藏
页码:3157 / 3163
页数:7
相关论文
共 36 条
[1]   SELECTIVE ALKYLATIONS OF 1,4/3,6-DIANHYDRO-D-GLUCITOL (ISOSORBIDE) [J].
ABENHAIM, D ;
LOUPY, A ;
MUNNIER, L ;
TAMION, R ;
MARSAIS, F ;
QUEGUINER, G .
CARBOHYDRATE RESEARCH, 1994, 261 (02) :255-266
[2]  
[Anonymous], 2014, Nature, V507, P7, Patent No. 0183488
[3]  
[Anonymous], NATURE
[4]   Recyclable homogeneous catalyst for the hydroesterification of methyl oleate in thermomorphic solvent systems [J].
Behr, A. ;
Vorholt, A. J. ;
Rentmeister, N. .
CHEMICAL ENGINEERING SCIENCE, 2013, 99 :38-43
[5]  
BELLER M, 2002, APPLIED HOMOGENEOUS, V1
[6]   Synthesis of new diesters of 1,4:3,6-dianhydro-D-glucitol by esterification with fatty acid chlorides [J].
Cecutti, C ;
Mouloungui, Z ;
Gaset, A .
BIORESOURCE TECHNOLOGY, 1998, 66 (01) :63-67
[7]  
CEKOVIC Z, 1989, SYNTHESIS-STUTTGART, P610
[8]   CARBON-MONOXIDE AS A BUILDING BLOCK FOR ORGANIC-SYNTHESIS .1. HIGHLY REGIOSELECTIVE ALKOXYCARBONYLATION OF ALLYLBENZENE CATALYZED BY PALLADIUM COMPLEXES [J].
CIPRES, I ;
JENCK, J ;
KALCK, P .
JOURNAL OF MOLECULAR CATALYSIS, 1990, 58 (03) :387-392
[9]   Characterization and dynamics of [Pd(L-L)H(solv)]+, [Pd(L-L)(CH2CH3)]+, and [Pd(L-L)(C(O)Et)(THF)]+ (L-L=1,2-(CH2PBut2)2C6H4):: Key intermediates in the catalytic methoxycarbonylation of ethene to methylpropanoate [J].
Clegg, W ;
Eastham, GR ;
Elsegood, MRJ ;
Heaton, BT ;
Iggo, JA ;
Tooze, RP ;
Whyman, R ;
Zacchini, S .
ORGANOMETALLICS, 2002, 21 (09) :1832-1840
[10]  
CLEGG W, 2002, DALTON T, V17, P3300