Abstract
The behavior of palmitaldehyde and linolealdehyde and of their dimethyl acetals during gas-liquid chromatography on beta-cyclodextrin acetate (beta-CDX acetate) and ethylene glycol succinate polyester-phosphoric acid (EGSP) columns was studied. The aldehydes were well separated from their dimethyl acetals on the beta-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% H(2)SO(4) they yielded the corresponding aldehydes, which were identified as 2,4-dinitrophenylhydrazones.
Highlights
The aldehydes were recovered unchanged in 80-85% yield by preparative gas-liquid chromatography (GLC) from both columns, but the dimethyl acetals were quantitatively converted to the corresponding alk-1-enyl methyl ethers
I n view of these divergent results, we studied the behavior of pure fatty aldehydes and their dimethyl acetals (DMA) on two stationary phases commonly used in GLC of lipid materials
This paper reports the behavior of pure DMA of palmitaldehyde and linolealdehyde, as well as of the free aldehydes, during GLC on 0-cyclodextrin acetate (p-CDX acetate) and ethylene glycol succinate-phosphoric acid (EGSP) columns
Summary
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. Gray [4] reported that when DMA were chromatographed on a poly(ethy1eneglycol adipate) column, they reacted in some way with the polyester to produce a mixture of compounds which included unchanged DMA and some of the corresponding acid methyl esters. Ullman, Safier, and Ballard [5] found that DMA did not emerge from Apiezon L or M columns when commercial solid supports were coated with these liquid phases. The products of decomposition in the former column were not identified
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