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Acid-catalyzed addition of phenols and phenyl ethers to oleic acid

  • Technical
  • Published:
Journal of the American Oil Chemists Society

Summary

Phenols and phenyl ethers have been added to oleic acid, using both sulfuric acid and a strong acid cation exchange resin as condensing agents. By-product formation during the condensations resulted in low yields and products which were difficult to purify. Infrared spectra were used to identify the various products and to show that ring isomers form. Infrared spectra also assisted in identifying by-products and permitted differentiation between the two strong acid condensing agents.

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Eastern Utilization Research and Development Division, Agricultural Research Service, U. S. Department of Agriculture.

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Roe, E.T., Parker, W.E. & Swern, D. Acid-catalyzed addition of phenols and phenyl ethers to oleic acid. J Am Oil Chem Soc 36, 656–659 (1959). https://doi.org/10.1007/BF02640281

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  • DOI: https://doi.org/10.1007/BF02640281

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