Pyrolysis Mechanisms of Aromatic Carboxylic Acids

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Although decarboxylation of carboxylic acids is widely used in organic synthesis, there is limited mechanistic information on the uncatalyzed reaction pathways of aromatic carboxylic acids at 300-400 {degrees} C. The pyrolysis mechanisms of 1,2-(3,3-dicarboxyphenyl)ethane, 1,2-(4,4-dicarboxylphenyl)ethane, 1-(3-carboxyphenyl)-2-(4- biphenyl)ethane, and substituted benzoic acids have been investigated at 325-425 {degrees} C neat and diluted in an inert solvent. Decarboxylation is the dominant pyrolysis path. Arrhenius parameters, substituent effects, and deuterium isotope effects are consistent with decarboxylation by an electrophilic aromatic substitution reaction. Pyrolysis of benzoic acid in naphthalene, as a solvent, produces significant amounts of 1- and 2-phenylnaphthalenes. The mechanistic pathways for decarboxylation ... continued below

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13 p.

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Britt, P.F.; Eskay, T.P. & Buchanan, A.C. III December 31, 1997.

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Description

Although decarboxylation of carboxylic acids is widely used in organic synthesis, there is limited mechanistic information on the uncatalyzed reaction pathways of aromatic carboxylic acids at 300-400 {degrees} C. The pyrolysis mechanisms of 1,2-(3,3-dicarboxyphenyl)ethane, 1,2-(4,4-dicarboxylphenyl)ethane, 1-(3-carboxyphenyl)-2-(4- biphenyl)ethane, and substituted benzoic acids have been investigated at 325-425 {degrees} C neat and diluted in an inert solvent. Decarboxylation is the dominant pyrolysis path. Arrhenius parameters, substituent effects, and deuterium isotope effects are consistent with decarboxylation by an electrophilic aromatic substitution reaction. Pyrolysis of benzoic acid in naphthalene, as a solvent, produces significant amounts of 1- and 2-phenylnaphthalenes. The mechanistic pathways for decarboxylation and arylation with be presented.

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13 p.

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OSTI as DE98001418

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  • American Chemical Society (ACS) meeting, Dallas, TX (United States), 26 Mar - 2 Apr 1998

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  • Other: DE98001418
  • Report No.: ORNL/CP--95384
  • Report No.: CONF-980314--
  • Grant Number: AC05-96OR22464
  • Office of Scientific & Technical Information Report Number: 622772
  • Archival Resource Key: ark:/67531/metadc696651

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  • December 31, 1997

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  • Aug. 14, 2015, 8:43 a.m.

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  • Jan. 20, 2016, 3:28 p.m.

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Britt, P.F.; Eskay, T.P. & Buchanan, A.C. III. Pyrolysis Mechanisms of Aromatic Carboxylic Acids, article, December 31, 1997; Tennessee. (digital.library.unt.edu/ark:/67531/metadc696651/: accessed August 20, 2017), University of North Texas Libraries, Digital Library, digital.library.unt.edu; crediting UNT Libraries Government Documents Department.