Process for the manufacture of carbonyl compounds
Patent Number: GB895843
Publication date: 1962-05-09
Inventor(s):
Applicant(s): CONSORTIUM ELEKTROCHEM IND
Requested Patent: GB895843
Application Number: GB19580028150 19580902
Priority Number(s): DEX895843 19570906
IPC Classification:
EC Classification: C07C45/28, C07C45/30, C07C45/34, C07C205/45, C07C317/44
Equivalents:
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Abstract
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Aldehydes and ketones are obtained by treating an organic compound containing one or more hetero atoms and one or more carbon to carbon double bonds, with an aqueous solution of a compound of a platinum group metal at 0 DEG C.-250 DEG C. Hetero atoms specified are oxygen, sulphur, halogens, and nitrogen. Metals specified are palladium and rhodium. The halides sulphates, phosphates, acetates, and corresponding complexes of these metals may be used. An oxidising agent is preferably also present in the reaction mixture, e.g. oxygen gas, persulphates, hydrohalic acids or salts, chromates, and other oxo-metallates. Salts of polyvalent metals such as iron and copper may also be present. The reaction is preferably carried out at a pH of 0-2, and the catalyst solution may be periodically reactivated by oxidation with, e.g. oxygen. The reactants may be brought into active contact by shaking, sprinkling, vibrating, or other methods. The process may be carried out at pressures of 1-50 atmospheres in trickling towers, columns of filler bodies, or vessels provided with stirrers. Examples are given of the production of p-methoxy - phenyl acetone from 4 - methoxy - 1 - propenyl benzene; 1,3,5-triacetyl benzene by ring closure of acetyl acetaldehyde which is first obtained from crotonaldehyde; acetaldehyde from acrylic acid, vinyl bromide, b -bromo styrene, and a -bromo-acrylic acid; acetone from crotonic acid, a -methoxy crotonic acid, 1-bromo propene, 2-chloropropene, a -chlorocrotonic acid, and crotonic acid amide; propionaldehyde from methycrylic acid, a -methacrylic acid amide, and allylamine; acetophenone from cinnamic acid, ethyl cinnamate, a -chlorostyrene, b -bromo-styrene, a -bromocinnamic acid, and cinnamic acid amide; pyruvic acid from maleic acid; methyl ethyl ketone from tiglic acid, a ,b -pentenic acid, 1-bromo butene (1), a -bromo-a ,b -pentenic acid and a ,b -pentenic acid amide; succinic acid aldehyde from itaconic acid; ethylidene acetone from sorbic acid; a -methyl acrolein and isobutyraldehyde from 1-chloro-2-methyl-propene (1); methyl glyoxal from allyl bromide, allyl chloride, 2,3-dibromopropene, and 1,3-dichloro-propene (1); pyruvonitrile from acrylonitrile; acrolein from allyl alcohol; p-methoxy acetophenone from p-methoxy styrene; 3,4-dioxymethylenebenzyl-methyl ketone from iso-safrole; n-propyl, n-butyl, and n-amyl methyl ketones from the corresponding a ,b -unsaturated acids, and their a -bromo derivatives; propiophenone from a -chloro-b -methyl styrene; benzyl methyl ketone from 2-chloro-1 or 3-phenyl propene (1); g -bromo-propyl methyl ketone from 1-bromopentene (4); p-chloroacetophenone from p-chlorostyrene and p-chloro-cinnamic acid; m-nitroacetophenone from m-nitro-styrene and m-nitrocinnamic acid methyl - [butanone - (2) - yl - (4)]-sulphone from the corresponding butene compound. Specifications 876,025 and 886,157 are referred to.