Dual-catalytic decarbonylation of fatty acid methyl esters to form olefins

被引:13
作者
Fieser, Megan E. [1 ]
Schimler, Sydonie D. [1 ]
Mitchell, Lauren A. [1 ]
Wilborn, Emily G. [1 ]
John, Alex [1 ]
Hogan, Levi T. [1 ]
Benson, Brooke [1 ]
LaPointe, Anne M. [2 ]
Tolman, William B. [1 ,3 ]
机构
[1] Univ Minnesota, Dept Chem, Ctr Sustainable Polymers, 207 Pleasant St SE, Minneapolis, MN 55455 USA
[2] Cornell Univ, Baker Lab, Dept Chem & Chem Biol, Ithaca, NY 14853 USA
[3] Washington Univ, Dept Chem, One Brookings Dr,Campus Box 1134, St Louis, MO 63130 USA
基金
美国国家科学基金会;
关键词
ALIPHATIC CARBOXYLIC-ACIDS; ACYL-OXYGEN BONDS; ORGANOBORON COMPOUNDS; HYDROCARBON FUELS; COUPLING REACTION; DECARBOXYLATION; DEOXYGENATION; DEHYDRATION; ALKENES; BIOMASS;
D O I
10.1039/c8cc03823f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The homogeneous dehydrative decarbonylation of fatty acid methyl esters (FAMEs) to form olefins is reported. In order to facilitate cleavage of the unactivated acyl C-O bond of the alkyl ester, a one pot dual-catalytic directing group strategy was developed through optimization of the individual transesterification and decarbonylation reaction steps.
引用
收藏
页码:7669 / 7672
页数:4
相关论文
共 44 条
[1]  
Arockiam PB, 2012, CHEM REV, V112, P5879, DOI [10.1021/cr300153J, 10.1021/cr300153j]
[2]   Ruthenium-catalyzed C-H/CO/olefin coupling reaction of N-arylpyrazoles.: Extraordinary reactivity of N-arylpyrazoles toward carbonylation at C-H bonds [J].
Asaumi, T ;
Chatani, N ;
Matsuo, T ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7538-7540
[3]   Production of green diesel via cleaner catalytic deoxygenation of Jatropha curcas oil [J].
Asikin-Mijan, N. ;
Lee, H. V. ;
Abdulkareem-Alsultan, G. ;
Afandi, A. ;
Taufiq-Yap, Y. H. .
JOURNAL OF CLEANER PRODUCTION, 2017, 167 :1048-1059
[4]   Palladium-Catalyzed Suzuki-Miyaura Coupling of Aryl Esters [J].
Ben Halima, Taoufik ;
Zhang, Wanying ;
Yalaoui, Imane ;
Hong, Xin ;
Yang, Yun-Fang ;
Houk, Kendall N. ;
Newman, Stephen G. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (03) :1311-1318
[5]   Copper-Catalyzed Dehydrogenative Coupling of Arenes with Alcohols [J].
Bhadra, Sukalyan ;
Matheis, Christian ;
Katayev, Dmitry ;
Goossen, Lukas J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9279-9283
[6]   The ruthenium-catalyzed reductive decarboxylation of esters: Catalytic reactions involving the cleavage of acyl-oxygen bonds of esters [J].
Chatani, N ;
Tatamidani, H ;
Ie, Y ;
Kakiuchi, F ;
Murai, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (20) :4849-4850
[7]   Palladium Precatalysts for Decarbonylative Dehydration of Fatty Acids to Linear Alpha Olefins [J].
Chatterjee, Anamitra ;
Eliasson, Sondre H. Hopen ;
Tornroos, Karl W. ;
Jensen, Vidar R. .
ACS CATALYSIS, 2016, 6 (11) :7784-7789
[8]   Bidentate, Monoanionic Auxiliary-Directed Functionalization of Carbon-Hydrogen Bonds [J].
Daugulis, Olafs ;
Roane, James ;
Tran, Ly Dieu .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (04) :1053-1064
[9]   Parameters Governing Ruthenium Sawhorse-Based Decarboxylation of Oleic Acid [J].
Doll, Kenneth M. ;
Bantchev, Grigor B. ;
Walter, Erin L. ;
Murray, Rex E. ;
Appell, Michael ;
Lansing, James C. ;
Moser, Bryan R. .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2017, 56 (04) :864-871
[10]   DECARBONYLATION DEHYDRATION OF FATTY-ACIDS TO ALKENES IN PRESENCE OF TRANSITION-METAL COMPLEXES [J].
FOGLIA, TA ;
BARR, PA .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1976, 53 (12) :737-741