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US 4,540,826 AGranted
Process for preparing olefinic aldehydes
AssigneePhillips Petroleum Company
InventorsDennis S. Banasiak, Jim D. Byers
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Abstract
A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.
Claims12
A process for the preparation of an olefinic aldehyde having the formula:
- H--(CR.sub.2)x--CH.sub.2 --CH.dbd.CH--CH.sub.2 --(CR.sub.2)y--CHO
- wherein x=0-20, inclusive, y=1-20, inclusive, and each R is independently H, C.sub.1 -C.sub.20 alkyl, cycloalkyl, aryl, aralkyl, and alkaryl which comprises the steps of:
- (a) reacting an .alpha.,.omega.-dihalide having the formula:
- X--CH.sub.2 --(CR.sub.2)y--CH.sub.2 --X
- wherein X is Cl, Br or I, and y and R are as defined above, with a metal acetylide having the formula:
- M--C.tbd.C--CH.sub.2 --(CR.sub.2)x--H
- wherein M is Li or Na and x and R are as defined above to give a reaction product containing an acetylenic halide having the formula:
- H--(CR.sub.2)x--CH.sub.2 --C.tbd.C--CH.sub.2 --(CR.sub.2)y--CH.sub.2 --X
- wherein x, y, R and X are as defined above;
- (b) hydrogenating the acetylenic halide obtained in (a) with hydrogen and a selective hydrogenation catalyst to give an olefinic halide having the formula:
- H--(CR.sub.2)x--CH.sub.2 --CH.dbd.CH--CH.sub.2 --(CR.sub.2)y--CH.sub.2 --X
- wherein x, y, R and X are as defined above;
- and
- (c) oxidizing the olefinic halide obtained in (b) to give said olefinic aldehyde.
11 more elements
Dependencies are inferred from the claim text.