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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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An ether molecule has a net dipole moment due to the polarity of C–O bonds. Subsequently, boiling points of ethers are lower than those of alcohols of comparable molecular weight and slightly higher than those of hydrocarbons of comparable molecular weight (Table 1).
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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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High-Pressure Rate Rules for Ether Alkylperoxy Radical Isomerization.

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This study details alkylperoxy radical isomerization in ethers, crucial for low-temperature oxidation. Calculated rate constants reveal ether group impacts, improving kinetic models for accurate combustion chemistry.

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Area of Science:

  • Chemical Kinetics
  • Combustion Chemistry
  • Reaction Mechanism

Background:

  • Alkylperoxy (RO2) radical isomerization is key to low-temperature oxidation, influencing hydroperoxyalkyl (QOOH) radical branching ratios.
  • Understanding these reactions is vital for predicting combustion behavior and controlling pollutant formation.

Purpose of the Study:

  • To systematically calculate high-pressure rate rules for RO2 isomerization in monoethers.
  • To investigate the influence of ring size, functional group position, and carbon site on reaction rates.

Main Methods:

  • Utilized G4//B3LYP/6-311++G(2df,2pd) level of theory and transition state theory.
  • Calculated rate constants and Arrhenius coefficients for over 120 isomerization reactions.
  • Compared ether isomerization rates to analogous alkane reactions.

Main Results:

  • Identified 6- and 7-membered ring transition states as generally the fastest isomerization pathways.
  • Observed significant differences in rate constants due to the ether functional group's position relative to the transition state ring.
  • Found rate constant differences up to an order of magnitude compared to analogous alkanes.

Conclusions:

  • Site-specific rate constants for ether isomerization are essential for accurate low-temperature combustion modeling.
  • The presence and position of the ether group significantly alter reaction pathways and rates.
  • Applied rate constants improved a di-iso-butyl ether kinetic model, altering branching ratios significantly.