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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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Room Temperature Ionic Liquids as Green Solvent Alternatives in the Metathesis of Oleochemical Feedstocks.

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Related Experiment Video

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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

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C18:1 Methyl ester metathesis in [bmim][X] type ionic liquids.

Priya A Thomas1, Bassie B Marvey

  • 1Department of Chemistry, North-West University, Mafikeng, South Africa. priyaaregi@gmail.com

International Journal of Molecular Sciences
|January 21, 2010
PubMed
Summary

Ionic liquids ([bmim][X]) improved methyl oleate metathesis using Grubbs catalysts, showing higher selectivity and performance than traditional organic solvents. This research highlights ILs as superior reaction media for olefin metathesis.

Keywords:
RuCl2(PCy3)(L)(=CHPh)[bmim][X]metathesismethyl oleate

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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Area of Science:

  • Green Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Olefin metathesis is a vital reaction in organic synthesis.
  • Conventional organic solvents pose environmental and safety concerns.
  • Ionic liquids (ILs) offer tunable properties as alternative reaction media.

Purpose of the Study:

  • To evaluate the efficacy of [bmim][X] ionic liquids (ILs) as reaction media for methyl oleate metathesis.
  • To compare IL performance against conventional organic solvents (PhCl, PhMe, DCM, DCE).
  • To investigate the influence of IL properties on catalytic performance.

Main Methods:

  • Utilized first and second generation Grubbs precatalysts for methyl oleate metathesis.
  • Compared catalytic performance in various [bmim][X] ILs (X = PF(6)(-), BF(4)(-), NTf(2)(-)) and organic solvents.
  • Analyzed effects of anion type, temperature, solvent polarity, viscosity, and ligand-anion interactions.

Main Results:

  • Achieved excellent catalytic performance and selectivity (>98%) in [bmim][X] ILs.
  • ILs outperformed conventional organic solvents under moderate reaction temperatures.
  • Identified specific anion effects and solvent properties influencing reaction outcomes.

Conclusions:

  • [bmim][X] ionic liquids are superior reaction media for methyl oleate metathesis compared to conventional solvents.
  • The choice of IL anion and reaction conditions significantly impacts catalytic efficiency and selectivity.
  • This study advocates for the use of ILs in sustainable olefin metathesis processes.