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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.
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Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
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Near-Surface Gas-Phase Methoxymethanol Is Generated by Methanol Oxidation over Pd-Based Catalysts.

Sadi M Gurses1, Trevor Price1, Angie Zhang2

  • 1Department of Chemical Engineering, University of California, Davis, California 95616, United States.

The Journal of Physical Chemistry Letters
|November 11, 2021
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Summary

Researchers identified methoxymethanol, a key C2 intermediate, during methanol oxidation over palladium catalysts. This finding advances understanding of alcohol conversion mechanisms and catalyst design for chemical synthesis.

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Area of Science:

  • Chemical Engineering
  • Catalysis Science
  • Surface Chemistry

Background:

  • Catalytic conversion of alcohols is vital for chemical synthesis.
  • Complete mechanistic understanding of methanol oxidation is lacking.
  • Identifying key intermediates is crucial for catalyst development.

Purpose of the Study:

  • To investigate the catalytic oxidative conversion of methanol near atmospheric pressure.
  • To identify and characterize reactive intermediates in methanol oxidation.
  • To provide a mechanistic basis for improving methanol oxidation catalysts.

Main Methods:

  • Operando small-aperture molecular beam time-of-flight mass spectrometry.
  • Interrogation of gas phase species above Pd-based catalyst surfaces.
  • Density functional theory calculations for pathway energetics.

Main Results:

  • Detected methoxymethanol (CH3OCH2OH), a rare C2 oxygenate intermediate.
  • Observed methoxymethanol over Pd, Pd-Au alloys, and oxide-supported Pd catalysts.
  • Established temperature and feed ratio dependencies for methoxymethanol generation.

Conclusions:

  • Methoxymethanol is a critical intermediate in methanol oxidation.
  • Catalyst and microkinetic model development should include methoxymethanol.
  • Findings guide future design of efficient methanol oxidation catalysts.