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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Pressure-Dependent Criegee Intermediate Stabilization from Alkene Ozonolysis.

Jani P Hakala1,2, Neil M Donahue1

  • 1Center for Atmospheric Particle Studies, Carnegie Mellon University , 5000 Forbes Avenue, Pittsburgh, Pennsylvania 15213, United States.

The Journal of Physical Chemistry. A
|March 29, 2016
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Summary

We measured stabilized Criegee Intermediate (sCI) formation from 2,3-dimethyl-2-butene ozonolysis. sCI stabilization increased linearly with pressure from 50 to 900 Torr, reaching 42% at 900 Torr.

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Area of Science:

  • Atmospheric Chemistry
  • Chemical Kinetics
  • Combustion Chemistry

Background:

  • Criegee intermediates (CIs) are key species in atmospheric oxidation processes.
  • Understanding the stabilization of Criegee intermediates is crucial for atmospheric modeling.
  • Acetone oxide is a syn-Criegee intermediate formed from 2,3-dimethyl-2-butene (TME) ozonolysis.

Purpose of the Study:

  • To investigate the pressure dependence of stabilized acetone oxide (sCI) formation.
  • To quantify the yield of sCI as a function of pressure.
  • To determine the zero-pressure yield of acetone oxide.

Main Methods:

  • Utilized a new, highly accurate technique involving a high-pressure flow reactor.
  • Ozonolysis of TME was used to produce Criegee intermediates.
  • Measured sulfuric acid (H2SO4) formation via chemical ionization mass spectrometry to quantify sCI yields.

Main Results:

  • Observed a linear pressure dependence for sCI formation between 50 and 900 Torr.
  • Minimum sCI stabilization was 12.7 ± 0.6% at 50 Torr.
  • Maximum sCI stabilization was 42 ± 2% at 900 Torr.
  • A linear fit yielded a zero-pressure intercept of 15 ± 2%.

Conclusions:

  • Acetone oxide stabilization increases significantly with pressure.
  • The zero-pressure intercept provides a constraint on the fraction of CIs formed below the isomerization barrier.
  • This study offers precise data on sCI formation crucial for atmospheric chemistry models.