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Sharpless Epoxidation02:57

Sharpless Epoxidation

3.8K
The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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Preparation of Epoxides03:00

Preparation of Epoxides

7.5K
Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of...
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Base-Catalyzed Ring-Opening of Epoxides02:26

Base-Catalyzed Ring-Opening of Epoxides

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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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5.7K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.7K
Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Dynamic Phase Behavior of Surface-Active Fluorinated Ionic Liquid Epoxidation Catalysts.

Markus Hegelmann1, Julian Zuber1, Johannes Luibl2

  • 1Technical University of Munich, Catalysis Research Center and School of Natural Sciences, Department of Chemistry, Ernst-Otto-Fischer-Straße 1, D-85748, Garching bei München, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 3, 2024
PubMed
Summary

We developed novel fluorinated surface-active ionic liquid (FSAIL) catalysts for olefin epoxidation. These catalysts exhibit temperature-controlled water solubility and efficient recycling, enabling mild reaction conditions and high activity.

Keywords:
EpoxidationFluorine functionalizationIonic liquidsPhase transfer catalysisSolubility

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Area of Science:

  • Catalysis
  • Green Chemistry
  • Materials Science

Background:

  • Developing efficient and recyclable catalysts is crucial for sustainable chemical synthesis.
  • Fluorinated surface-active ionic liquids (FSAILs) offer unique solubility properties for catalytic applications.
  • Controlling catalyst solubility is key to enabling homogeneous catalysis and simplifying separation.

Purpose of the Study:

  • To synthesize novel amphiphobic FSAILs for epoxidation reactions.
  • To investigate the temperature-controlled solubility of these FSAILs in aqueous and organic phases.
  • To evaluate the catalytic activity, recyclability, and reaction conditions for olefin epoxidation using FSAILs.

Main Methods:

  • Synthesis of amphiphobic fluorinated surface-active ionic liquid (FSAIL) epoxidation catalysts.
  • Solubility studies of FSAILs in aqueous and organic media at varying temperatures.
  • Epoxidation of olefins using aqueous hydrogen peroxide (H2O2) as the oxidant.
  • Catalyst recycling through phase separation and product distillation.

Main Results:

  • FSAILs demonstrated reversible, temperature-controlled solubility in water.
  • Catalyst solubility decreased significantly in aqueous and substrate phases compared to non-fluorinated analogs.
  • Epoxide product and phenylphosphonic acid (PPA) facilitated homogeneous reaction conditions.
  • High catalytic activity was observed under mild conditions for olefin epoxidation.
  • Successful catalyst recycling over ten consecutive runs was achieved.

Conclusions:

  • Amphiphobic FSAILs are effective catalysts for olefin epoxidation with high activity and selectivity.
  • Temperature-controlled solubility enables efficient catalyst separation and recycling, promoting green chemistry principles.
  • These FSAILs represent a promising class of catalysts for sustainable industrial applications.