Homogenous catalytic conjugation of polyunsaturated fats by chromium carbonyls |
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Authors: | E N Frankel |
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Affiliation: | (1) Northern Regional Research Laboratory, 61604 Peoria, Illinois |
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Abstract: | Various arene-Cr (CO)3 complexes and Cr(CO)6 are effective soluble catalysts for the conjugation of polyunsaturated fats. Methyl benzoate-Cr(CO)3 is one of the most active catalysts. The following conjugation levels were obtained: methyl linoleate, 65%; methyl linolenate,
45%; the polyunsaturates in soybean and safflower oils, 73%; and in linseed oil 48%. Conjugated dienes from linoleate were
predominantlycis,trans in configuration. Their double bonds were distributed between C5 and C16 of the fatty acid chain. Hydrogenation and dehydrogenation are side reactions, which seem to limit the yield of conjugated
dienes from methyl linoleate. A conjugation mechanism is proposed that involves allyl-HCr(CO)3 complexes as intermediates undergoing 1,3- and 1,5-hydrogen shifts.
Presented at the AOCS Meeting, San Francisco, April 1969.
No, Utiliz. Res. Dev. Div., ARS, USDA. |
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