Optimized reaction conditions for the cross-metathesis of methyl oleate and oleylamine with ethyl acrylate

被引：24

作者：

Abbas, Mudassar ^{[1
]}

Slugovc, Christian ^{[1
]}

机构：

[1] Graz Univ Technol, Inst Chem & Technol Mat, A-8010 Graz, Austria

来源：

MONATSHEFTE FUR CHEMIE | 2012年 / 143卷 / 04期

关键词：

Methyl oleate; Oleylamine; Ethyl acrylate; Cross-metathesis; RENEWABLE RAW-MATERIALS; FATTY-ACID DERIVATIVES; ACRYLONITRILE; OILS;

D O I：

10.1007/s00706-011-0717-x

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The cross-metathesis of methyl oleate and oleylamine with ethyl acrylate has been studied using three different ruthenium-based second-generation catalysts. Emphasis was on determining the smallest amount of catalyst necessary for full conversion of technical grade educts. Conversion of methyl oleate is best performed in the presence of 10 equiv. ethyl acrylate without use of additional solvent whereas oleylamine cannot be used directly and protection of the amino group is necessary. An easy protection procedure for oleylamine with acetic anhydride was developed and the best results for cross-metathesis of N-acetyloleylamine were obtained in toluene solution.

引用

页码：669 / 673

页数：5

共 50 条

[41] Metathesis of unsaturated compounds: Thermodynamic calculation of equilibrium for the methyl oleate ethenolysis reaction
Furman, D.B.
Dmitriev, R.V.
Vasil'kov, M.A.
Barkova, A.P.
Kustov, L.M.
Neftekhimiya, 2003, 43 (06): : 450 - 454
[42] As low as reasonably achievable catalyst loadings in the cross metathesis of olefins with ethyl acrylate
Abbas, Mudassar
Slugovc, Christian
TETRAHEDRON LETTERS, 2011, 52 (20) : 2560 - 2562
[43] Olefin Cross-Metathesis: a Versatile Synthetic Reaction for the Design of Janus Liquid Crystals
Thi Minh Nguyet Trinh
Thanh Tung Nguyen
Kopp, Cyril
Pieper, Pauline
Russo, Virginie
Heinrich, Benoit
Donnio, Bertrand
Thi Le Anh Nguyen
Deschenaux, Robert
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2015, 2015 (27) : 6005 - 6010
[44] Synthesis of new multiblock copolymers via cross-metathesis reaction of polytrimethylsilylnorbornene and polycyclooctene
Yu. I. Denisova
M. L. Gringolts
L. B. Krentsel’
G. A. Shandryuk
A. S. Peregudov
E. Sh. Finkelshtein
Y. V. Kudryavtsev
Polymer Science, Series B, 2017, 59 : 412 - 420
[45] REACTION OF ETHYL ACRYLATE WITH METHYL NORMAL-HEXYL KETONE
MILLER, JJ
DEBENNEVILLE, PL
JOURNAL OF ORGANIC CHEMISTRY, 1957, 22 (10): : 1268 - 1269
[46] Synthesis of New Multiblock Copolymers via Cross-Metathesis Reaction of Polytrimethylsilylnorbornene and Polycyclooctene
Denisova, Yu. I.
Gringolts, M. L.
Krentsel, L. B.
Shandryuk, G. A.
Peregudov, A. S.
Finkelshtein, E. Sh.
Kudryavtsev, Y. V.
POLYMER SCIENCE SERIES B, 2017, 59 (04) : 412 - 420
[47] Synthesis of vinyl nitriles and allylsilanes via the selective cross-metathesis reaction.
Goldberg, DR
Crowe, WE
Zhang, ZJ
Rachita, CL
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1996, 211 : 16 - ORGN
[48] Improved cross-metathesis of acrylate esters catalyzed by 2nd generation ruthenium carbene complexes
Forman, GS
Tooze, RP
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2005, 690 (24-25) : 5863 - 5866
[49] Cross-metathesis of fatty acid methyl esters with acrolein: An entry to a variety of bifunctional compounds
Bonin, Helene
Keraani, Adel
Dubois, Jean-Luc
Brandhorst, Markus
Fischmeister, Cedric
Bruneau, Christian
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2015, 117 (02) : 209 - 216
[50] A Nonclassical Stereoselective Semi-Synthesis of Drospirenone via Cross-Metathesis Reaction
Bandini, Marco
Contento, Michele
Garelli, Andrea
Monari, Magda
Tolomelli, Alessandra
Umani-Ronchi, Achille
Andriolo, Erika
Montorsi, Mauro
SYNTHESIS-STUTTGART, 2008, (23): : 3801 - 3804

← 1 2 3 4 5 →