scholarly journals Equilibrium data for the cross-metathesis of methyl oleate with cinnamaldehyde

Data in Brief ◽  
2018 ◽  
Vol 20 ◽  
pp. 190-195
Author(s):  
Pablo D. Nieres ◽  
Andrés F. Trasarti ◽  
Carlos R. Apesteguía
Keyword(s):  
Methyl Oleate ◽  
Cross Metathesis ◽  
Equilibrium Data ◽  
The Cross

scholarly journals The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups

2011 ◽  
Vol 7 ◽  
pp. 1-8 ◽  
Author(s):  
Arno Behr ◽  
Jessica Pérez Gomes
Keyword(s):  
Methyl Oleate ◽  
Renewable Resources ◽  
Value Added ◽  
Ruthenium Catalysts ◽  
Protecting Groups ◽  
Catalyst Loading ◽  
Reaction Conditions ◽  
Functional Monomers ◽  
Cross Metathesis ◽  
The Cross

Background: α,ω-Difunctional substrates are useful intermediates for polymer synthesis. An attractive, sustainable and selective (but as yet unused) method in the chemical industry is the oleochemical cross-metathesis with preferably symmetric functionalised substrates. The current study explores the cross-metathesis of methyl oleate (1) with cis-2-butene-1,4-diyl diacetate (2) starting from renewable resources and quite inexpensive base chemicals. Results: This cross-metathesis reaction was carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. The influence of protecting groups present in the substrates on the necessary catalyst loading was also investigated. Conclusions: The value-added methyl 11-acetoxyundec-9-enoate (3) and undec-2-enyl acetate (4) are accessed with nearly quantitative oleochemical conversions and high cross-metathesis selectivity under mild reaction conditions. These two cross-metathesis products can be potentially used as functional monomers for diverse sustainable polymers.

scholarly journals Fishing for the right catalyst for the cross-metathesis reaction of methyl oleate with 2-methyl-2-butene

2017 ◽  
Vol 7 (6) ◽  
pp. 1284-1296 ◽  
Author(s):  
A. Sytniczuk ◽  
A. Kajetanowicz ◽  
K. Grela
Keyword(s):  
Methyl Oleate ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross ◽  
The Right

A comparison of the reactivity of different ruthenium-based complexes in the cross-metathesis reaction of methyl oleate was presented.

Heterogeneous catalysis for valorisation of vegetable oils via metathesis reactions: ethenolysis of methyl oleate

2016 ◽  
Vol 6 (17) ◽  
pp. 6561-6568 ◽  
Author(s):  
P. D. Nieres ◽  
J. Zelin ◽  
A. F. Trasarti ◽  
C. R. Apesteguía
Keyword(s):  
Heterogeneous Catalysis ◽  
Methyl Oleate ◽  
Vegetable Oils ◽  
Second Generation ◽  
Cross Metathesis ◽  
Metathesis Reactions ◽  
The Cross

A second-generation Hoveyda–Grubbs complex supported on silica efficiently catalyzes the cross-metathesis of methyl oleate with ethylene.

Complete Stereocontrol in the Synthesis of Harmonine and Novel Analogues Facilitated by a Grubbs Z-Selective Cross-Metathesis Catalyst

2015 ◽  
Vol 68 (12) ◽  
pp. 1815 ◽  
Author(s):  
Steven-Alan G. Abel ◽  
Wesley J. Olivier ◽  
Richard L. Pederson ◽  
Alex C. Bissember ◽  
Jason A. Smith
Keyword(s):  
The Self ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Metathesis Catalyst ◽  
The Cross

(R)-Harmonine was synthesised in 15 % overall yield via a six-step sequence exploiting a Z-selective cross-metathesis reaction as its centrepiece. By this strategy, the cis-olefin present in the target could be installed exclusively. The use of an alcohol and an ester as the amine precursors was crucial for isolating the cross-metathesis product from the self-metathesis products. This method was also used to prepare two novel analogues of harmonine.

Low Catalyst Loading in the Cross Metathesis of Olefins with Methyl Vinyl Ketone

Synlett ◽  
2013 ◽  
Vol 24 (10) ◽  
pp. 1193-1196 ◽  
Author(s):  
Christian Slugovc ◽  
Muddasar Abbas ◽  
Anita Leitgeb
Keyword(s):  
Vinyl Ketone ◽  
Methyl Vinyl Ketone ◽  
Catalyst Loading ◽  
Methyl Vinyl ◽  
Cross Metathesis ◽  
The Cross ◽  
Low Catalyst Loading

scholarly journals Computational study of productive and non-productive cycles in fluoroalkene metathesis

2015 ◽  
Vol 11 ◽  
pp. 2150-2157 ◽  
Author(s):  
Markéta Rybáčková ◽  
Jan Hošek ◽  
Ondřej Šimůnek ◽  
Viola Kolaříková ◽  
Jaroslav Kvíčala
Keyword(s):  
Computational Study ◽  
Catalytic Cycle ◽  
Dft Study ◽  
Cross Metathesis ◽  
High Preference ◽  
The Cross

A detailed DFT study of the mechanism of metathesis of fluoroethene, 1-fluoroethene, 1,1-difluoroethene, cis- and trans-1,2-difluoroethene, tetrafluoroethene and chlorotrifluoroethene catalysed with the Hoveyda–Grubbs 2nd generation catalyst was performed. It revealed that a successful metathesis of hydrofluoroethenes is hampered by a high preference for a non-productive catalytic cycle proceeding through a ruthenacyclobutane intermediate bearing fluorines in positions 2 and 4. Moreover, the calculations showed that the cross-metathesis of perfluoro- or perhaloalkenes should be a feasible process and that the metathesis is not very sensitive to stereochemical issues.

Regulation of the degree of blockiness of the norbornene–cyclooctene copolymer synthesized via the cross-metathesis reaction

2016 ◽  
Vol 58 (3) ◽  
pp. 292-297 ◽  
Author(s):  
Yu. I. Denisova ◽  
M. L. Gringolts ◽  
L. B. Krentsel’ ◽  
G. A. Shandryuk ◽  
A. D. Litmanovich ◽  
...  
Keyword(s):  
Metathesis Reaction ◽  
Cross Metathesis ◽  
The Cross
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