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Related Concept Videos

Catalysis02:50

Catalysis

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.
Precipitation of Ions03:11

Precipitation of Ions

Predicting Precipitation
The equation that describes the equilibrium between solid calcium carbonate and its solvated ions is:
1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism01:37

1° Amines to Diazonium or Aryldiazonium Salts: Diazotization with NaNO2 Mechanism

Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
Masking and Demasking Agents01:19

Masking and Demasking Agents

EDTA titrations may necessitate masking and demasking agents to temporarily protect a particular metal ion in a mixture from the EDTA reaction. These agents facilitate the sequential analysis of the metal ions by forming stable complexes with some—but not all—metal ions during certain steps.
There are many masking agents, such as cyanide, fluoride, triethanolamine, thiourea, and 2,3-bis(sulfanyl)propan-1-ol (formerly 2,3-dimercapto-1-propanol), with the masking agent chosen based on the metal...
Catalysis01:27

Catalysis

Catalysis influences the rate of chemical reactions by providing an alternative reaction pathway with lower activation energy. A catalyst speeds up a reaction, but it is not consumed during the process. The fundamental principle of catalysis is the ability of a catalyst to alter the reaction mechanism, often introducing a more efficient pathway than the uncatalyzed process.In a catalyzed reaction, the catalyst participates directly in the reaction mechanism. It interacts with reactants to form...
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...

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Hydrophobic Salt-modified Nafion for Enzyme Immobilization and Stabilization
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Bulky diarylammonium arenesulfonates as selective esterification catalysts.

Kazuaki Ishihara1, Shoko Nakagawa, Akira Sakakura

  • 1Graduate School of Engineering, Nagoya University, Furo-cho, Chikusa, Nagoya 464-8603, Japan. ishihara@cc.nagoya-u.ac.jp

Journal of the American Chemical Society
|March 24, 2005
PubMed
Summary

New bulky diarylammonium catalysts enable efficient ester condensation reactions. These environmentally friendly catalysts are highly active, recyclable, and effective even with challenging alcohols and without solvent use.

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Area of Science:

  • Green Chemistry
  • Organic Synthesis

Background:

  • Developing environmentally benign chemical processes is crucial.
  • Ester condensation is a fundamental large-scale reaction.
  • Current methods often lack efficiency or require harsh conditions.

Purpose of the Study:

  • To introduce novel, highly active dehydration catalysts for ester condensation.
  • To demonstrate the effectiveness of bulky diarylammonium salts with challenging substrates.
  • To explore solvent-free and recyclable catalytic systems.

Main Methods:

  • Utilized bulky diarylammonium pentafluorobenzenesulfonates and tosylates as catalysts.
  • Performed esterification of carboxylic acids with sterically demanding and acid-sensitive alcohols.
  • Conducted reactions in heptane at 80°C and explored solvent-free conditions for primary alcohols.

Main Results:

  • Diarylammonium catalysts demonstrated high activity in ester condensation.
  • Efficient esterification was achieved with sterically demanding and acid-sensitive alcohols.
  • Solvent-free esterification with primary alcohols occurred at room temperature.
  • A recyclable resin-bound catalyst maintained activity over 10 cycles.

Conclusions:

  • Bulky diarylammonium salts are effective and versatile catalysts for ester condensation.
  • These catalysts offer a greener alternative to existing methods, enabling reactions under mild conditions.
  • The recyclability of the resin-bound catalyst highlights its potential for sustainable chemical synthesis.