Exploring the reactivity of a ruthenium complex in the metathesis of biorenewable feedstocks to generate value-added chemicals

被引:21
作者
Alexander, Kathryn A. [1 ]
Paulhus, Emily A. [1 ]
Lazarus, Gillian M. L. [1 ]
Leadbeater, Nicholas E. [1 ]
机构
[1] Univ Connecticut, Dept Chem, 55 North Eagleville Rd, Storrs, CT 06269 USA
基金
美国国家科学基金会;
关键词
Metathesis; Ruthenium; Biorenewable; N-heterocyclic carbene; Valorization; RING-CLOSING METATHESIS; OLEFIN CROSS-METATHESIS; FATTY-ACID ESTERS; CONTINUOUS-FLOW; METHYL OLEATE; CATALYSTS; ETHENOLYSIS; EFFICIENT; CHEMISTRY; OILS;
D O I
10.1016/j.jorganchem.2015.09.018
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
Tricyclohexylphosphine[4,5-dimethyl-1,3-bis(2,4,6-trimethylphenypimidazol-2-ylidene][2-thienylmeth ylene]ruthenium(II) dichloride proves active for the ring-closing metathesis of linalool and citronellene, the self-metathesis of eugenol, and to some extent the ethenolysis of methyl oleate. Microwave heating and continuous-flow processing have been used as tools for performing the reactions. For the ring closing metathesis reactions, transition from batch to flow processing for scale-up of the reaction is possible but it proves problematic in the case of cross-metathesis. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:74 / 80
页数:7
相关论文
共 85 条
[11]   New approaches to olefin cross-metathesis [J].
Blackwell, HE ;
O'Leary, DJ ;
Chatterjee, AK ;
Washenfelder, RA ;
Bussmann, DA ;
Grubbs, RH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (01) :58-71
[12]   Terpenic Compounds as Renewable Sources of Raw Materials for Cross-Metathesis [J].
Borre, Etienne ;
Dinh, Trong Hoa ;
Caijo, Frederic ;
Crevisy, Christophe ;
Mauduit, Marc .
SYNTHESIS-STUTTGART, 2011, (13) :2125-2130
[13]   COMETATHESIS OF METHYL OLEATE AND ETHYLENE - A DIRECT ROUTE TO METHYL DEC-9-ENOATE [J].
BOSMA, RHA ;
VANDENAARDWEG, F ;
MOL, JC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (21) :1132-1133
[14]   In situ tandem allylic acetate isomerisation-ring closing metathesis: 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ruthenium benzylidenes and palladium(0)-phosphine combinations [J].
Braddock, DC ;
Matsuno, A .
TETRAHEDRON LETTERS, 2002, 43 (18) :3305-3308
[15]   The Influence of Phosphane Ligands on the Versatility of Ruthenium-Indenylidene Complexes in Metathesis [J].
Broggi, Julie ;
Urbina-Blanco, Cesar A. ;
Clavier, Herve ;
Leitgeb, Anita ;
Slugovc, Christian ;
Slawin, Alexandra M. Z. ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) :9215-9225
[16]   Ruthenium Carbenes Supported on Mesoporous Silicas as Highly Active and Selective Hybrid Catalysts for Olefin Metathesis Reactions under Continuous Flow [J].
Bru, Miriam ;
Dehn, Richard ;
Teles, J. Henrique ;
Deuerlein, Stephan ;
Danz, Manuel ;
Mueller, Imke B. ;
Limbach, Michael .
CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (35) :11661-11671
[17]   Flow Chemistry: Intelligent Processing of Gas-Liquid Transformations Using a Tube-in-Tube Reactor [J].
Brzozowski, Martin ;
O'Brien, Matthew ;
Ley, Steven V. ;
Polyzos, Anastasios .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (02) :349-362
[18]   Renewable monomer feedstocks via olefin metathesis: Fundamental mechanistic studies of methyl oleate ethenolysis with the first-generation grubbs catalyst [J].
Burdett, KA ;
Harris, LD ;
Margl, P ;
Maughon, BR ;
Mokhtar-Zadeh, T ;
Saucier, PC ;
Wasserman, EP .
ORGANOMETALLICS, 2004, 23 (09) :2027-2047
[19]   Measurement of the vaporization enthalpy of complex mixtures by correlation-gas chromatography.: The vaporization enthalpy of RJ-4, a high-energy-density rocket fuel at T=298.15 K [J].
Chickos, JS ;
Wentz, AE ;
Hillesheim-Cox, D ;
Zehe, MJ .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2003, 42 (12) :2874-2877
[20]   Refining of Plant Oils to Chemicals by Olefin Metathesis [J].
Chikkali, Samir ;
Mecking, Stefan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (24) :5802-5808