GB331100A - Process for the manufacture of oxygenated organic compounds - Google Patents

Abstract

331,100. Carpmael, A., (I. G. Farbenindustrie Akt.-Ges.). June 28, 1929. Oxygenated organic compounds. - Oxygenated organic compounds are prepared by treating aromatic hydrocarbons or their halogenated derivatives in the liquid state and at a raised temperature and pressure with molecular oxygen or a gas containing free oxygen in the presence of a substantial amount of liquid water and a small amount of an oxidation catalyst. Suitable catalysts are the oxides and hydroxides of copper, nickel, cobalt, and iron, and the oxides of manganese, cerium, osmium, uranium, vanadium, chromium, and zinc; mixtures of such catalysts may also be used. The reaction may be modified by effecting it in the presence of carbon dioxide. Examples are given as follows :-(1) toluene is treated with oxygen at 240‹ C. under 60-60 atm. pressure in the presence of water and hydrated ferric oxide (FeO.OH)3; benzaldehyde is obtained, with a little benzoic acid and traces of benzyl alcohol and dibenzyl ether; (2) as in example 1, but using a mixture of hydrated ferric oxide and uranium oxide as catalyst; benzoic acid mainly is obtained, besides the other products specified in example 1; (3) as in example 1, but using air as the oxidant and ferric oxide as catalyst; benzaldehyde and benzoic acid are obtained; (4) as in example 1, but with carbon dioxide present; benzoic acid and some benzaldehyde are obtained; (5) p-xylene is treated with oxygen at 235‹ C. under 60 atm. pressure in the presence of water and hydrated ferric oxide; p-toluic acid and ptoluic aldehyde are obtained; (6) m-xylene is similarly oxidized in the presence of vanadium pentoxide; m-toluic acid and m-toluic aldehyde are obtained, with traces of isophthalic acid; (7) ethylbenzene is treated with oxygen at 170‹ C. under 20 atm. pressure in the presence of water and hydrated ferric oxide; phenyl methyl carbinol, acetophenone, and a little benzoic acid are obtained; (8) naphthalene is treated with a mixture of nitrogen and oxygen at 270‹ C. under 85 atm. pressure in the presence of water, sodium carbonate, and a catalyst comprising hydrated ferric oxide, copper oxide, cerium dioxide, and chromium oxide; benzoic and phthalic acids are ultimately obtained; (9) anthracene is treated with oxygen at 250‹ C. under 60 atm. pressure in the presence of water, sodium carbonate, and a catalyst comprising hydrated ferric oxide and cerium dioxide; anthraquinone is obtained; (10) p-chlortoluene is oxidized as in example 1; p-chlorobenzaldehyde and p-chlorobenzoic acid are obtained.