Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1985-03-14
1987-02-10
Killos, Paul J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560103, 560104, 560105, 560232, 562406, 562520, C07C 6976
Patent
active
046423702
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to a process for the production of carboxylic acid esters.
According to the present invention there is a provided a process for the production of a carboxylic acid ester which process comprises reacting (i) carbon monoxide, (ii) a compound of the formula M(OR).sub.x wherein M is either boron, silicon, aluminium, titanium or zirconium, x is the valency of M and R is a hydrocarbyl group and (iii) a hydrocarbyl halide, wherein the halide moiety is bromide, chloride or iodide, in the presence of a catalyst comprising one or more of the metals rhodium, iridium and cobalt added in either elemental or compound form.
In the formula M(OR).sub.x wherein M is either boron, silicon, aluminium, titanium or zirconium and x is the valency of M, the hydrocarbyl group may suitably be alkyl, aryl, aralkyl, cycloalkyl or substituted derivatives thereof. Preferably R in the aforesaid formula is alkyl, which is preferably a primary or a secondary alkyl. Examples of suitable R groups include --C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2 and --CH(CH.sub.3)C.sub.2 H.sub.5. Preferably the metal M is boron, silicon or aluminium.
The hydrocarbyl moiety of the hydrocarbyl halide may suitably be an aromatic group, a benzylic group, an aliphatic group or a substituted derivative thereof and may be saturated or unsaturated. The halide moiety is either chloride, bromide or iodide, though the chlorides are preferably used in conjunction with compounds of the formula M(OR).sub.x wherein M is of boron, silicon or aluminium when there is added an effective amount of a source of iodide. An amount suitable as an effective amount may be readily determined by those skilled in the art, but will usually be found to be of the order of that which is generally regarded as a catalytic amount. The source of iodide may suitably be iodine, an inorganic iodide or an organic iodide. Suitable inorganic iodides include the alkali metal iodides, of which potassium iodide is preferred. Suitable organic iodides include alkyl iodides, for example methyl iodide, and quaternary alkyl or aryl ammonium iodides. It will be appreciated that a source of iodide may be added with possible advantage when the halide moiety is bromide, though it is not essential for the effective working of the process. Examples of hydrocarbyl halides suitable for use in the process of the invention include benzyl bromide, benzyl chloride, para-methyl benzyl bromide, meta-methyl benzyl bromide, ortho-methyl benzyl bromide, para-fluoro benzyl bromide, 2-bromomethylnaphthalene, 1-bromomethylnaphthalene, bromobenzene and beta-bromostyrene.
Carbon monoxide is commercially available on a large scale and may be used without further purification. Alternatively, purified carbon monoxide may be employed. A wide range of carbon monoxide pressures may be used.
The cataylst comprises one or more of the metals rhodium, iridium and cobalt added in elemental or compound form. Preferably the metal is rhodium. Although the metal or metals may be employed in elemental form, preferably in a finally divided state, it is preferred to employ them in the form of soluble compounds. Suitable compounds include the salts of the metals, for example rhodium trichloride (RhCl.sub.3), carbonyl complexes, for example Rh(CO).sub.2 Cl.sub.2 and organo compounds of the metals. Suitable organo compounds include dienyl metal complexes in which the dienyl moiety may be either linear or cyclic and either conjugated or non-conjugated, for example 1,5-hexadiene rhodium(I) chloride dimer. It is preferred, particularly when the hydrocarbyl halide reactant is an aromatic halide, for example a bromo-substituted benzene or naphthalene, to employ a bimetallic catalyst. Suitably the bimetallic catalyst comprises one of the metals rhodium, iridium and cobalt, preferably rhodium, and another metal selected from Group VIII of the Periodic Table of the elements as found in Advanced Inorganic Chemistry (2nd Edition) by F. A. Cotton and G. Wilkinson, of which palladium is preferred. It is also preferred to employ, as on
REFERENCES:
patent: 3116306 (1963-12-01), Heck
patent: 3928429 (1975-12-01), El-Chahawi et al.
patent: 4034004 (1977-07-01), Cassar et al.
Alper Howard
Smith David J. H.
Woell James B.
Killos Paul J.
The British Petroleum Company p.l.c.
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