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.

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 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 Value-Added Bio-Chemicals Commodities from Catalytic Conversion of Biomass Derived Furan-Compounds

Catalysts ◽  
2020 ◽  
Vol 10 (8) ◽  
pp. 895
Author(s):  
Aitziber Iriondo ◽  
Ion Agirre ◽  
Nerea Viar ◽  
Jesús Requies
Keyword(s):  
Renewable Resources ◽  
Petrochemical Industry ◽  
Raw Materials ◽  
Value Added ◽  
Building Blocks ◽  
Reaction Conditions ◽  
Potential Market ◽  
Forestry Residues ◽  
Industry Needs ◽  
Near Future

The depletion of fossil resources in the near future and the need to decrease greenhouse gas emissions lead to the investigation of using alternative renewable resources as raw materials. One of the most promising options is the conversion of lignocellulosic biomass (like forestry residues) into bioenergy, biofuels and biochemicals. Among these products, the production of intermediate biochemicals has become an important goal since the petrochemical industry needs to find sustainable alternatives. In this way, the chemical industry competitiveness could be improved as bioproducts have a great potential market. Thus, the main objective of this review is to describe the production processes under study (reaction conditions, type of catalysts, solvents, etc.) of some promising intermediate biochemicals, such as; alcohols (1,2,6-hexanetriol, 1,6-hexanetriol and pentanediols (1,2 and 1,5-pentanediol)), maleic anhydride and 5-alkoxymethylfuran. These compounds can be produced using 5-hydroxymethylfurfural and/or furfural, which they both are considered one of the main biomass derived building blocks.

Cross metathesis of methyl oleate (MO) with terminal, internal olefins by ruthenium catalysts: factors affecting the efficient MO conversion and the selectivity

RSC Advances ◽  
2016 ◽  
Vol 6 (103) ◽  
pp. 100925-100930 ◽  
Author(s):  
Nor Wahida Awang ◽  
Ken Tsutsumi ◽  
Barbora Huštáková ◽  
Siti Fairus M. Yusoff ◽  
Kotohiro Nomura ◽  
...  
Keyword(s):  
Methyl Oleate ◽  
High Selectivity ◽  
Ruthenium Catalysts ◽  
Factors Affecting ◽  
Cross Metathesis

Cross metathesis (CM) of methyl oleate (MO) with cis-4-octene, cis-stilbene, allyltrimethylsilane by RuCl2(PCy3)(IMesH2)(CHPh) yielded CM products with high MO conversion, high selectivity; the effect of olefin substituents, conditions was explored.

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.

scholarly journals 1H NMR Analysis of the Metathesis Reaction between 1-Hexene and (E)-Anethole Using Grubbs 2nd Generation Catalyst: Effect of Reaction Conditions on (E)-1-(4-Methoxyphenyl)-1-hexene Formation and Decomposition

Catalysts ◽  
2021 ◽  
Vol 11 (12) ◽  
pp. 1483
Author(s):  
Marthinus Rudi Swart ◽  
Charlene Marais ◽  
Elizabeth Erasmus
Keyword(s):  
1H Nmr ◽  
Maximum Concentration ◽  
Metathesis Reaction ◽  
Reaction Conditions ◽  
2Nd Generation ◽  
Cross Metathesis ◽  
First Order Kinetics ◽  
Different Temperatures ◽  
The Cross ◽  
Catalyst Effect

The metathesis of 1-hexene and (E)-anethole in the presence of Grubbs 2nd generation catalyst was monitored by in situ 1H NMR spectroscopy at different temperatures (15 °C, 25 °C, and 45 °C) and anethole mol fractions (XAnethole ≈ 0.17, 0.29, 0.5, 0.71, 0.83). Time traces confirmed the instantaneous formation of (E)-1-(4-methoxyphenyl)-1-hexene, the cross-metathesis product. A maximum concentration of (E)-1-(4-methoxyphenyl)-1-hexene is reached fairly fast (the time depending on the reaction conditions), and this is followed by a decrease in the concentration of (E)-1-(4-methoxyphenyl)-1-hexene due to secondary metathesis. The maximum concentration of (E)-1-(4-methoxyphenyl)-1-hexene was more dependent on the XAnethole than the temperature. The highest TOF (3.46 min−1) was obtained for the reaction where XAnethole was 0.16 at 45 °C. The highest concentration of the cross-metathesis product was however achieved after 6 min with an anethole mol fraction of 0.84 at 25 °C. A preliminary kinetic study indicated that the secondary metathesis reaction followed first order kinetics.

Sign in / Sign up

Export Citation Format

Share Document