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Phenyloctadecanol and surface-active derivatives

  • Technical
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Journal of the American Oil Chemists’ Society

Abstract

Phenyloctadecanol from the Friedel-Crafts reaction, like phenylstearic acid, is a viscous oil and a mixture of several position isomers. Gasliquid chromatography of the acetophenone homologs formed by CrO3 oxidation showed it to be a mixture of 13 position homologs, with substitution of the phenyl group at carbon atoms 5-17. A crystalline 17-phenyloctadecanol was isolated. Reaction of oily phenyloctadecanol with dioxane-SO3 sulfated the primary alcohol group to give sodium phenyloctadecyl sulfate CH3 (CH2)xCH (C6H5) (CH2)y CH2OSO3Na, where x + y = 15. Reaction of phenyloctadecanol with 2.4 moles of SO3 gave an impure p-sulfophenyloctadecyl sulfate, hydrolyzed to sodium p-sulfophenyloctadecanol CH3(CH2)xCH (p-Cin6) H4SO3Na) (CH2)yCH2OH, and sulfated again with dioxane-SO3 to disodium p-sulfophenyl-octadecyl sulfate CH3(CH2)xCH(p-C6H4SO3Na) (CH2)yCH2OSO3Na. Foam, detergency, and other surface-active properties were compared with those of the p-sulfo anda-sulfo derivatives of oily phenylstearic acid.

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Authors and Affiliations

  1. Eastern Regional Research Laboratory, Philadelphia, Pennsylvania

    F. D. Smith, A. J. Stirton & M. V. Nuñez-Ponzoa

Authors
  1. F. D. Smith
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  2. A. J. Stirton
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  3. M. V. Nuñez-Ponzoa
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Additional information

1 Presented at the AOCS Meeting in Philadelphia, October 1966.

2E. Utiliz. Res. Dev. Div., ARS, USDA.

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Smith, F.D., Stirton, A.J. & Nuñez-Ponzoa, M.V. Phenyloctadecanol and surface-active derivatives. J Am Oil Chem Soc 44, 413–415 (1967). https://doi.org/10.1007/BF02666781

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  • DOI: https://doi.org/10.1007/BF02666781

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