Process for the preparation of carboxylic acids and esters there

Details Process for the preparation of carboxylic acids and esters there Process for the preparation of carboxylic acids and esters there

1995-05-01

1998-02-03

Geist, Gary

Organic compounds -- part of the class 532-570 series

Organic compounds

Fatty compounds having an acid moiety which contains the...

554156, 252367, 252368, 252369, 562523, 562538, 562539, C07C 5116, C07C 51235

Patent

active

057146233

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/EP93/02944 filed Oct. 25, 1993.


FIELD OF THE INVENTION

The present invention relates to a process for the production of carboxylic acids and esters thereof comprising the operation of: compound, in the presence of a catalyst belonging to the group consisting oxides of molybdenum and tungsten and their corresponding acids and alkaline salts, obtaining an intermediate reaction product and in the presence of a cobalt compound which acts as a catalyst.
A process of the above mentioned type, that is defined on the whole as an oxidative cleavage, is described in the following consecutive reaction I and II, where the intermediate product is a vicinal diol in which the hydroxy groups are attached to the carbon atoms that in the starting compound were connected with a olefinic double bond: ##STR1## where p=0-1, m=0-2, t=0-11, z=1-3; R.sub.1 =H, C.sub.1 -C.sub.8 alkyl or a CH.sub.3 --(CH.sub.2).sub.3 --CH(OH)--CH.sub.2 radical and in which if z=1, A is H or C.sub.1 -C.sub.5 ;


DESCRIPTION OF THE PRIOR ART

The U.S. Pat. No. 4,606,863 describes a process of the above indicated type in which in certain embodiments the starting fatty acid/ester is oxidised with hydrogen in the presence of a catalyst based on tungsten or molybdenum and a solvent such as acetic acid.
The intermediate reaction product so obtained, which may contain vicinal diols or epoxy groups, ethers or esters, are purified from the solvent and water formed in the course of the reaction. They are then subjected to further oxidation with oxygen or an oxygen containing gas in the presence of a heavy metal compound, for example cobalt, and a bromine or chlorine compound.
In addition, if the intermediate product has a high melting point or if it is necessary to get rid of a notable heat of reaction, a polar organic solvent, such as C.sub.2 -C.sub.10 saturated carboxylic acid, is used as the reaction solvent.
The process described by U.S. Pat. No. 4,696,863 has the inconvenience of requiring a purification treatment of the intermediate reaction products and the additional presence of a bromine or chlorine compound, in order to activate the heavy metal acting as a catalyst, and optionally an organic solvent. The process as a whole moreover lacks selectivity with respect to the formation of specific compounds.
U.S. Pat. No. 3,711,523, U.S. Pat. No. 3,816,525 and British Patent 1,405,578 describe oxidation processes of vicinal diols or epoxides in order to obtain carboxylic acids with an oxidising system consisting of peroxides such as peracetic acid, and oxygen or an oxygen containing gas in the presence of a cobalt based catalyst.
Such processes are not adapt for industrial scale production as they use dangerous and costly reagents such as peracetic acid. Moreover, they are preferably carried out in organic solvents with the additional complication arising from the separation of the reaction products there from, which in itself creates an additional cost.
British Patent 1,330,205 describes a process for the production of carboxylic acids through oxidation of vicinal diols using a catalyst system comprising a cobalt salt such as acetate in the presence of a pertungsten or permolybdenum acid or similar compounds in a bipolar aprotic solvent.
Such a process has the disadvantage of requiring the use of costly and difficultly recyclable solvents and requires that the diols to be oxidised are anhydrous.
It is in fact known that water has an adverse effect on the bipolar aprotic solvents in that it eliminates a positive effect that said solvents have in the oxidative cleavage reaction (see Tetrahedron Letters 54, pag. 5689, 1968, Pergamon Press). The reason for such an effect is probably due to the fact that the catalytic action of the cobalt salt appears to be connected to the formation of a super red Co(III) complex (see R. A. Sheldon, and J. K. Kochi in "Metal-Catalysed Oxidations of Organic Compounds", 1981, Academic Press, Pages 75 and 144) and the formation of Co(III) compound is highly disactivated by the presence of water

REFERENCES:
patent: 3895040 (1975-07-01), Miyazaki et al.
patent: 4550196 (1985-10-01), Venturello et al.
patent: 4606863 (1986-08-01), Nakazawa et al.

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