Hydroformylation of unsaturated fatty esters |
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Authors: | E. N. Frankel S. Metlin W. K. Rohwedder I. Wender |
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Affiliation: | (1) Northern Regional Research Laboratory, 61604 Peoria, Illinois;(2) Pittsburgh Coal Research Center, 15213 Pittsburgh, Pennsylvania |
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Abstract: | Unsaturated fatty esters and vegetable oils were hydroformylated with H2 and CO (3500–4600 psi) and Co2(CO)8 to give fatty aldehydes at 100–110 C and fatty alcohols at 175–190 C. Yields of distillable C19 oxo products varied from 42% to 84%. Distilled products contained from 50% to 90% branched isomers and from 4% to 16% linear isomers. The proportion of linear isomers increased at higher reaction temperatures and in the presence of tributylphosphine-cobalt carbonyl complex. Linear and branched hydroxy products were separated by silicic acid column, thin-layer, and gas-liquid chromatography. The linear hydroxy product (from oleate and linoleate) was identified as methyl 19-hydroxynonadecanoate by nuclear magnetic resonance and mass spectrometry. Isomeric branched products were analyzed by mass spectrometry as the diester derivatives. They were identified as a mixture of 5- to 13-carbomethoxy methyl octadecanoate. Presented at the AOCS-AACC Joint Meeting, Washington, D.C., March 1968. No. Utiliz. Res. Dev. Div., ARS, USDA. Bureau of Mines, U.S. Dept. of Interior. |
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