Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Patent
1991-02-20
1993-09-07
Dees, Jose G.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
560 76, 562480, 562481, 562483, 562488, 562855, C07C 67475, C07C 5109, C07C 5160
Patent
active
052430677
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for the production of a 3,4,3',4'-substituted biphenyl compound. More particularly, the present invention relates to a process for the selective production of a 3,4,3',4'-substituted biphenyl compound from o-toluic acid alkyl esters by an oxidative coupling reaction in the presence of a palladium containing catalyst The 3,4,3',4'-substituted biphenyl compounds produced by the process of the present invention include novel compounds useful for the production of polyesters or polyamides.
BACKGROUND ART
In the past, biphenyl dicarboxylic acid dialkyl esters have been produced by preparing corresponding biphenyl dicarboxylic acids by various known production processes and the esterifying the biphenyl dicarboxylic acids with alcohols.
As the conventional processes for producing the biphenyl carboxylic acids, there are known a process for causing coupling of a 3-bromo benzoic acid by a treatment with a KOH-methanol aqueous solution in the presence of a Pd/C catalyst (U.S. Pat. No. 2,809,210), a process for preparing a Grignard reagent from 4,4'-dichlorobiphenyl, then causing a reaction of the resultant reagent with CO.sub.2 (U.S. Pat. No. 2,508,022), a process for oxidizing 3,3'-dimethyl biphenyl by using potassium permanganate (Journal of American Chemistry; J. Am. Chem. Soc. 72, 3221 (1950)), a process for iodizing biphenyl, then causing a reaction of the resultant product with carbon monoxide (Japanese Unexamined Patent Publication No. 63-104942), and a process for oxidizing 4,4'-diisopropyl biphenyl with molecular oxygen (Japanese Unexamined Patent Publication No. 63-122645).
Further, as another process for producing the above-mentioned biphenyl- dicarboxylic acid, there is known the process for oxidizing 3,3',4,4'-tetramethyl biphenyl with molecular oxygen to synthesize 3,3'-dimethyl biphenyl-4,4'-dicarboxylic acid (Japanese Examined Patent Publication (Kokoku) No. 52-3377).
Nevertheless, these conventional processes for producing biphenyl dicarboxylic acid suffer from many defects, e.g., it is difficult to acquire the materials, extremely complicated and long steps are required, and there are many byproducts. Accordingly, all of the conventional processes in which biphenyl dicarboxylic acid is produced and then biphenyl dicarboxylic acid dialkyl esters are produced therefrom, have a poor practically in industrial terms.
Further, it was difficult to selectively manufacture 3,4,3',4'-substituted dimethyl biphenyl dicarboxylic acid dialkyl esters by the conventional processes or by processes provided by combinations of the same.
DISCLOSURE OF THE INVENTION
The object of the present invention is to provide a process for producing 3,4,3',4'-substituted dimethyl biphenyl dicarboxylic acid compounds with a high selectivity. Also, the process of the present invention enables a novel 3,4,3',4'-substituted dimethyl biphenyl dicarboxylic acid compounds to be obtained.
The process of the present invention is a process for producing a 3,4,3',4'-substituted biphenyl compound, comprising the steps of:
oxidatively coupling an o-toluic acid alkyl ester represented by the following general formula (I): ##STR2## in which formula (I), R.sup.5 represents an alkyl group having 1 to 5 carbon atoms, in the presence of a catalyst containing at least one member selected from the group consisting of mixtures of palladium salts with at least one member selected from 1,10-phenanthroline and .alpha.,.alpha.'-bipyridine, in an amount of 0.9 to 4 times the molar amount of palladium salts chelating products of palladium salts with 1,10-phenanthroline, and chelating products of palladium salts with .alpha.,.alpha.'-bipyridine, in an atmosphere containing molecular oxygen, to selectively produce a dimethyl biphenyl dicarboxylic acid dialkyl ester having two methyl groups and two alkoxy carbonyl groups substituted at 3, 4, 3', and 4'-positions of the biphenyl ring structure;
and optionally converting the resultant dimethyl biphenyl dicarboxylic acid dialkyl ester to a correspo
REFERENCES:
patent: 2508022 (1950-05-01), Gluesenkamp
patent: 2809210 (1957-10-01), Short et al.
patent: 4174447 (1979-11-01), Fields
patent: 4288588 (1981-09-01), Donohue
patent: 4294976 (1981-10-01), Itatani et al.
patent: 4338456 (1982-07-01), Itatani et al.
patent: 4581469 (1986-04-01), Itatani et al.
patent: 4582925 (1986-04-01), Donohue
patent: 4727185 (1988-02-01), Shoji et al.
Chemical Abstracts, vol. 78, No. 4, Entry 17644w, (1972).
Chemical Abstracts, vol. 81, No. 6, Entry 27069p, (1973).
Chemical Abstracts, vol. 81, No. 12, Entry 65068v, (1973).
Chemical Abstracts, vol. 81, No. 24, Entry 153492j, (1973).
Chemical Abstracts, vol. 83, No. 2, Entry 11181z, (1974).
Chemical Abstracts, vol. 87, No. 5, Entry 39127t, (1977).
Matsuo Fumio
Shiotani Akinori
Suzuki Michinori
Clarke Vera C.
Dees Jos,e G.
Ube Industries Ltd.
LandOfFree
Process of production of 3,4,3',4'-substituted biphenyl compound does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process of production of 3,4,3',4'-substituted biphenyl compound, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process of production of 3,4,3',4'-substituted biphenyl compound will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-488988