Journal of Lipid Research, Vol. 8, 2-6, January 1967
Copyright © 1967 by Lipid Research, Inc.

Conversion of fatty aldehyde dimethyl acetals to the corresponding alk-1-enyl methyl ethers (substituted vinyl ethers) during gas-liquid chromatography

V. Mahadevan , C. V. Viswanathan , and F. Phillips

University of Minnesota, The Hormel Institute, Austin

The behavior of palmitaldehyde and linolealdehyde and of their dimethyl acetals during gas-liquid chromatography on ßbeta;-cyclodextrin acetate (ßbeta;-CDX acetate) and ethylene glycol succinate polyester-phosphoric acid (EGSP) columns was studied. The aldehydes were well separated from their dimethyl acetals on the ßbeta;-CDX acetate column. However, on the EGSP column the retention times of palmitaldehyde and its dimethyl acetal were identical; a mixture of linolealdehyde and its dimethyl acetal gave a split peak.

The aldehydes were recovered unchanged in 80-85% yield by preparative GLC from both columns, but the dimethyl acetals were quantitatively converted to the corresponding alk-1-enyl methyl ethers. The structure of these compounds was elucidated by infrared spectroscopy, mass spectrometry, and chemical means. Upon hydrolysis at low temperatures with 100% H₂SO₄ they yielded the corresponding aldehydes, which were identified as 2,4-dinitrophenylhydrazones.

Supplementary key words separation • gas-liquid chromatography • fatty aldehydes • dimethyl acetals • instability • conversion • alk-1-enyl methyl ethers • low temperature hydrolysis

Submitted on June 20, 1966
Accepted on September 1, 1966

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