Alkyl azelaaldehydates of high purity from alkyl soyates: Preparation and properties View Full Text


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Article Info

DATE

1971-05

AUTHORS

R. A. Awl, E. H. Pryde, D. Weisleder, W. K. Rohwedder, J. C. Cowan

ABSTRACT

Reductive ozonolysis of appropriate alkyl soyates in various participating media producted methyl, ethyl,n-propyl, isopropyl andn-butyl azelaaldehydates in good yield and high purity (98+%). The participating media examined were: methyl, ethyl,n-propyl andn-butyl alcohols; mixtures of an alcohol and acetic acid; water; and mixtures of water and acetic acid. Any combination of solvent and ester, except methanol-methyl soyate, allowed good separation by fractional distillation of ester and acetal impurities from the azelaaldehydate. A preparative method was developed by which high purity ethyl azelaaldehydate is produced from soybean oil by reductive ozonolysis in water. The only major impurity by this method was ethyl hydrogen azelate, which was easily removed with a bicarbonate wash. After a single fractional distillation with a short Vigreux column, the azelaaldehydate was obtained in 78% yield and 98+% purity. Physical properties and spectral (IR, NMR and mass spectroscopy) and chromatographic data were determined for the pure alkyl azelaaldehydates. Several of these properties were also determined for acetal and diester byproducts. More... »

PAGES

232-236

References to SciGraph publications

  • 1963-12. Methyl azelaaldehydate purification via the bisulfite compound in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1965-03. Omega-formylalkanoates by ozonization of unsaturated fatty esters in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1965-01. Preparation of malonaldehyde acetals by ozonolysis of polyunsaturated fatty esters in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1966-03. Removal of metal catalysts from aldehyde oils in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1968-02. Laboratory optimization of process variables in reductive ozonolysis of methyl soyate in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1965-10. A comparison of participating solvents during ozonization in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1963-07. Smalley check sample program under way in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • 1969-04. Reactions of azelaaldehydic esters in JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/bf02883759

    DOI

    http://dx.doi.org/10.1007/bf02883759

    DIMENSIONS

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