Chemistry: electrical and wave energy – Processes and products
Patent
1983-09-12
1985-06-25
Niebling, John F.
Chemistry: electrical and wave energy
Processes and products
204 59R, 204 72, C07B 2906
Patent
active
045252513
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a novel process for industrial production of dimethyl esters of higher dibasic acids and more particularly, to a process for producing dimethyl esters of higher dibasic acids by the crossed Kolbe electrolytic condensation of monomethyl adipate or monomethyl glutarate with the monomethyl ester of a C.sub.8 -C.sub.11 dicarboxylic acid.
BACKGROUND ART
Dimethyl esters of higher dibasic acids have very expanded use as raw materials for perfumes, various polymers, plasticizers, and so forth. In particular, dimethyl brassylate, dimethyl pentadecanedioate, and dimethyl thapsate are exceedingly useful as raw materials for producing ethylene brassylate, cyclopentadecanone and the like, which are very important as musk perfumes.
Processes now practiced and those so far proposed for producing higher dibasic acids and their esters are illustrated by the following examples pertaining to brassylic acid, pentadecanedioic acid, thapsic acid, and their esters.
Brassylic acid and esters thereof are produced by oxidizing erucic acid which is contained in rapeseed oil, with ozone or permanganic acid. This method, however, involves problems such as low yields of the oxidation, formation of various compounds by the reaction, troublesome purification of the intended product, and low purity of the product.
In addition, the following processes have been proposed for synthesizing brassylic acid: a process in which diethyl malonate is reacted with methyl undecylenate to be added thereto using di-tertbutyl peroxide, and the product is then hydrolyzed [Kirkiacharian, Berdj, Bull. Soc. Chim. Fr., (5), 1797 (1971)]; a process in which ethyl 11-bromoundecanoate and ethyl cyanoacetate are reacted by heating in dimethylformamide, and the product is decarboxylated after its hydrolysis [Dudinov, A. A., Izv. Akad. Nauk, SSSR, Ser, Khim, 1974(6), 1421-1423]; a process in which 2-ethoxycarbonylcyclododecanone and sodium hydroxide are heated in diethylene glycol and the reaction mixture is then acidified (Japanese Patent Publication No. 34,406/71); and a process in which 2,2'-methylenebis(cyclohexanone) is converted into 6,6-methylenebis(6-hexanolide) by reacting with a peroxy acid in a halogenated organic solvent in the presence of an alkali carbonate, and the product is heated with pressurized hydrogen in alcohol in the presence of metallic catalyst and an acid catalyst (Japanese Patent Application Kokai No. 113,741/80). However, these processes are not always satisfactory as industrial processes because raw materials are difficult to obtain or an expensive and hazardous peroxide is necessary to the reaction.
As to pentadecanedioic acid and esters thereof, various production processes have so far been proposed. For example, there are proposed the following processes: a process in which a dioxo ester is obtained from monomethyl glutarate acid chloride and a cadmium compound prepared from .alpha., .omega.-dibromopentane, and is subjected, after saponification, to the Wolff-Kishner reduction [A. Kreuchunas, J.A.C.S., 75, 3339(1953)]; a process in which ustilic acid obtained by the hydrolysis of ustilagic acid in methanol with alkali is treated with lead tetraacetate in glacial acetic acid, and the resulting aldehyde acid is oxidized with hydrogen peroxide in an aqueous alkali solution (U.S. Pat. No. 2,717,266); a process in which diethyl undecyleneylmalonate is obtained from undecylenic acid by a known method and reacted in toluene to add hydrogen bromide, the resulting diethyl 11-bromoundecyl malonate is reacted with diethyl malonate in the presence of sodium alcoholate, and the product is hydrolyzed and decarboxylated (Japanese Patent Publication No. 10,322/57); a process in which ethyl 15,16-dihydroxylignocerate is oxidized with sodium periodate and the resulting .omega.-oxotridecane-1-carboxylic acid is oxidized with potassium permanganate in acetone (German Patent No. 1,187,600); and a process in which aleuritic acid is treated with hydrogen bromide in acetic acid, the resulting 9,10,16-tribromopa
REFERENCES:
patent: 3879271 (1975-04-01), Nohe
patent: 3896011 (1975-07-01), Isoya
patent: 4237317 (1980-12-01), Yamataka
Chemical Abstracts, vol. 66, 1967, p. 4095, Abstract No. 43109x.
Chemical Abstracts, vol. 74, 1971, p. 295, Abstract No. 52994z.
Oil Chemistry, vol. 12, p. 669, (1963).
Y. B. Vassiliev et al., Electrochimica Acta, 27(7), 953-962 and 937-952, (1982).
Isoya Toshiro
Yamataka Kazunori
Asahi Kasei Kogyo Kabushiki Kaisha
Niebling John F.
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