Metathesis of cardanol over ammonium tagged Hoveyda-Grubbs type catalyst supported on SBA-15

被引:14
作者
Balcar, Hynek [1 ]
Zilkova, Nadezda [1 ]
Kubu, Martin [1 ]
Polasek, Miroslav [1 ]
Zednik, Jiri [2 ]
机构
[1] Acad Sci Czech Republ, J Heyrovsky Inst Phys Chem, Vvi, Dolejskova 3, CZ-18223 Prague 8, Czech Republic
[2] Charles Univ Prague, Fac Sci, Dept Phys & Macromol Chem, Hlavova 8 2030, CZ-12843 Prague 2, Czech Republic
关键词
Cardanol; Olefin metathesis; Hoveyda-Grubbs type catalyst; Immobilized catalyst; SBA-15; Flow chemistry; MESOPOROUS MOLECULAR-SIEVES; NUT SHELL LIQUID; OLEFIN METATHESIS; DERIVATIVES; PORPHYRINS;
D O I
10.1016/j.cattod.2017.09.049
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Cardanol (a mixture of phenols with C-15 aliphatic unsaturated chain in meta position, manufactured from cashew nut shell liquids) is an abundant and till now practically waste natural material. An important way leading to its utilization as a renewable source of valuable phenolic compounds is represented by olefin metathesis. Quaternary ammonium tagged Ru complex of Hoveyda-Grubbs type immobilized on SBA-15 mesoporous molecular sieve by non-covalent interactions was proved as a very efficient catalyst for cardanol metathesis under mild conditions (35 degrees C, toluene, 0.1 mol% of catalyst). The catalyst was used also in cross-metathesis of cardanol with alkenes (1-hexene, 1-heptene, 3-hexene, 4-octene) and unsaturated esters (methyl acrylate, 1,4-diacetoxybutene-2) under high yields of cross-metathesis products. The catalysts exhibited low leaching (from 0.2 ppm to 2.9 ppm Ru in products) and can be used in a continuous flow reactor (cumulative TON = 2500).
引用
收藏
页码:127 / 134
页数:8
相关论文
共 17 条
[1]  
Baader S, 2014, GREEN CHEM, V16, P4885, DOI [10.1039/C4GC01269K, 10.1039/c4gc01269k]
[2]   Recent advances in cardanol chemistry in a nutshell: from a nut to nanomaterials [J].
Balachandran, Vijai Shankar ;
Jadhav, Swapnil Rohidas ;
Vemula, Praveen Kumar ;
John, George .
CHEMICAL SOCIETY REVIEWS, 2013, 42 (02) :427-438
[3]   Mesoporous molecular sieves as advanced supports for olefin metathesis catalysts [J].
Balcar, H. ;
Cejka, J. .
COORDINATION CHEMISTRY REVIEWS, 2013, 257 (21-22) :3107-3124
[4]   An efficient route to biscardanol derivatives and cardanol-based porphyrins via olefin metathesis [J].
Guo, Ying-Cen ;
Mele, Giuseppe ;
Martina, Francesca ;
Margapoti, Eleonora ;
Vasapollo, Giuseppe ;
Xiao, Wen-Jing .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2006, 691 (24-25) :5383-5390
[5]   Selective ethenolysis and oestrogenicity of compounds from cashew nut shell liquid [J].
Julis, Jennifer ;
Bartlett, Stuart A. ;
Baader, Sabrina ;
Beresford, Nicola ;
Routledge, Edwin J. ;
Cazin, Catherine S. J. ;
Cole-Hamilton, David J. .
GREEN CHEMISTRY, 2014, 16 (05) :2846-2856
[6]   Process for isolation of cardanol from technical cashew (Anacardium occidentale L.) nut shell liquid [J].
Kumar, PP ;
Paramashivappa, R ;
Vithayathil, PJ ;
Rao, PVS ;
Rao, AS .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (16) :4705-4708
[7]   Synthesis of novel porphyrins cardanol based via cross metathesis [J].
Mele, Giuseppe ;
Li, Jun ;
Margapoti, Eleonora ;
Martina, Francesca ;
Vasapollo, Giuseppe .
CATALYSIS TODAY, 2009, 140 (1-2) :37-43
[8]   Synthesis of Bifunctional Monomers by the Palladium-Catalyzed Carbonylation of Cardanol and its Derivatives [J].
Mgaya, James E. ;
Bartlett, Stuart A. ;
Mubofu, Egid B. ;
Mgani, Quintino A. ;
Slawin, Alexandra M. Z. ;
Pogorzelec, Peter J. ;
Cole-Hamilton, David J. .
CHEMCATCHEM, 2016, 8 (04) :751-757
[9]   Synthesis of a kairomone and other chemicals from cardanol, a renewable resource [J].
Mmongoyo, Juma A. ;
Mgani, Quintino A. ;
Mdachi, Stephen J. M. ;
Pogorzelec, Peter J. ;
Cole-Hamilton, David J. .
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2012, 114 (10) :1183-1192
[10]   From cashew nut shell wastes to high value chemicals [J].
Mubofu, Egid B. .
PURE AND APPLIED CHEMISTRY, 2016, 88 (1-2) :17-27