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United States Patent (19) (11) 4,138,580 Umemura Et Al

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United States Patent (19) (11) 4,138,580 Umemura Et Al United States Patent (19) (11) 4,138,580 Umemura et al. 45 Feb. 6, 1979 54 PROCESS FOR PREPARING DIESTERS OF DCARBOXYLCACDS FOREIGN PATENT DOCUMENTS 75 Inventors: Sumio Umemura; Kanenobu Matsui; 2161418 7/1972 Fed. Rep. of Germany. Yoshinari Ikeda; Katsuro Masunaga, 2321180 11/1973 Fed. Rep. of Germany. all of Ube, Japan 2512062 9/1975 Fed. Rep. of Germany. 73) Assignee: Ube Industries, Ltd., Ube, Japan OTHER PUBLICATIONS J. Org. Chem. 37, No. 12, 2034-2035, (1972). (21) Appl. No.: 837,850 Derwent Abstract Jap. Pat. Provisional Publin. SHO-4- (22) Filed: Sep. 29, 1977 9-66619/1974. 30 Foreign Application Priority Data Derwent Abstract Jap. Pat. Provisional Publin. SHO-4- 9-116018/1974. Oct. 6, 1976 JP Japan ................................ 51/119403 Jul. 19, 1977 JP Japan .................................. 52/85565 Primary Examiner-Jane S. Myers Attorney, Agent, or Firm-Flynn & Frishauf 51) Int. Cl’.............................................. CO7C 67/38 52 U.S. C. ...................................... 560/81; 560/114; 57 ABSTRACT 560/131; 560/139; 560/144; 560/146; 560/193; A process for preparing a diester of a dicarboxylic acid 560/198; 560/204 having two more carbon atoms than the unsaturated 58) Field of Search ................. 560/204, 81, 114, 193, hydrocarbon used as a starting material, which com 560/198, 131, 139, 144, 146 prises subjecting an unsaturated hydrocarbon, carbon (56) References Cited monoxide and an alcohol to reaction in the presence of U.S. PATENT DOCUMENTS a platinum group metal in combination with one or 3,397,226 8/1968 Fenton ................................. 560/204 more compounds selected from the group consisting of 3,530,168 9/1970 Biale ... ... 260/486 nitric acid, a nitrogen oxide and an ester of nitrous acid. 3,625,995 12/1971 Brattesoni... 560/204 3,755,421 8/1973 Fenton et al. ..................... 260/48 X 16 Claims, No Drawings 4,138,580 2 Group II, VII or VIII of the Periodic Table are used in PROCESS FOR PREPARING DESTERS OF combination as the third substance instead of a dehy DICARBOXYLIC ACDS drating agent has also been proposed for improvement of conventional catalyst systems. Although the water This invention relates to a novel process for prepar resistance of these catalyst systems is enhanced, the ing diesters of dicarboxylic acids. yield and the selectivity of the desired product have not More particularly, this invention relates to a process necessarily been increased to a satisfactory extent. Fur for preparing a diester of a dicarboxylic acid corre ther, the conventional catalyst systems have problems sponding to the unsaturated hydrocarbon used as a in that the separation, recovery, regeneration, etc., of starting material, namely, a diester of a dicarboxylic 10 the expensive catalysts are complicated since a third acid having two more carbon atoms than the unsatu substance is used in those catalyst systems and the cata rated hydrocarbon used, which comprises subjecting an lyst systems are complicated because of their multi unsaturated hydrocarbon, carbon monoxide and an components. alcohol to reaction in the presence of a platinum group In view of these circumstances, we have made vari metal in combination with one or more compounds 5 ous studies to find an industrially superior catalyst sys selected from the group consisting of nitric acid, a nitro tem to those proposed conventionally, which is to be gen oxide and an ester of nitrous acid, and introducing used in the process for preparing a diester of a dicarbox molecular oxygen into the reaction system as occasion ylic acid corresponding to the unsaturated hydrocarbon demands. used as the starting material, which comprises subject According to this invention, a diester of succinic acid 20 ing an unsaturated hydrocarbon, carbon monoxide and is obtained when ethylene is used as the unsaturated an alcohol to reaction, with introduction of molecular hydrocarbon, and diesters of dicarboxylic acids such as oxygen as occasion demands. As a result of these stud substituted succinic acids, substituted or unsubstituted ies, we have found that a diester of a dicarboxylic acid maleic acid and cycloalkane dicarboxylic acids are ob can be prepared industrially with high selectivity. tained as the diester of a dicarboxylic acid when an 25 Namely, this invention relates to an industrially excel unsaturated hydrocarbon other than ethylene is used as lent process for preparing a diester of a dicarboxylic the starting material. For example, when propylene is acid having two more carbon atoms than the unsatu used as the unsaturated hydrocarbon, a diester of meth rated hydrocarbon used, which comprises subjecting an ylsuccinic acid with a smaller amount of diesters of unsaturated hydrocarbon, carbon monoxide and an glutaric acid in some cases are obtained; when cyclo 30 alcohol in the presence of a platinum group metal, in hexene is used, a mixture of diesters of 1,2- and 1,3- combination with one or more compounds selected cyclohexane dicarboxylic acids is obtained; and when from the group consisting of nitric acid, a nitrogen acetylene is used, a diester of maleic acid is obtained. oxide and an ester of nitrous acid, and introducing mo A process for preparing a diester of a dicarboxylic lecular oxygen into the reaction system as occasion acid having two more carbon atoms than the unsatu 35 demands. rated hydrocarbon used as the starting material, which According to this invention, not only the yield and comprises subjecting an unsaturated hydrocarbon, car the selectivity of the desired diester of a dicarboxylic bon monoxide and an alcohol to reaction, and introduc acid are increased in comparison with those of hitherto ing molecular oxygen into the reaction system as occa known processes, but also expensive dehydrating agents sion demands, is widely known, and various catalysts and complicated procedures and controls for keeping have been proposed for the reaction. the reaction system anhydrous are unnecessary since For example, U.S. Pat. No. 3,397,226 discloses an our catalyst system is much less sensitive to water than invention which employs as a catalyst a salt of a plati the conventional catalysts. Further, the catalyst of this num group metal and a redox agent comprising a salt of invention does not show any corrosive action against a multivalent metal such as copper, iron, etc. However, 45 the apparatus and hence apparatus of a special material it is taught that the reaction system should necessarily becomes unnecessary. Further, the catalyst system of be kept substantially anhydrous, preferably by using a this invention is simple, being composed of a platinum large amount of dehydrating agents such as isocyanates, group metal and one or more compounds selected from diimides, orthoalkyl esters, etc., because this catalyst the group consisting of nitric acid, a nitrogen oxide and system brings about a decrease in the yield of the de 50 an ester of nitrous acid. So, the procedures of separa sired product, diester of dicarboxylic acid, due to water tion, recovery and regeneration of the catalyst from the produced during the reaction and increased by-pro reaction system, and separation and obtaining of the ducts such as carbon dioxide. Not only are the proce desired product are simplified. Thus, the present pro dure and the control for maintaining an anhydrous reac cess is industrially superior to hitherto known processes tion system very difficult and complicated according to 55 and is extremely significant industrially. this process, but also the dehydrating agent used cannot The present invention will be explained further in be reutilized since it is converted into an entirely differ detail as follows. ent compound during the dehydration reaction. Ac As the unsaturated hydrocarbons used in this inven cordingly, the cost for preparing a diester of a dicarbox tion are aliphatic and alicyclic hydrocarbons having 2 ylic acid becomes extremely high according to this to 20 carbon atoms such as ethylene, propylene, butene, conventional process. Furthermore, although it is sug pentene, hexene, heptene, octene, nonene, decene, un gested that a platinum group metal and a multivalent decene, dodecene, tridecene, tetradecene, pentadecene, metal chloride are the most effective catalysts accord hexadecene, heptadecene, octadecene, nonadecene, ing to this conventional process, the corrosive action of eicosene and their isomers, and cyclopentene, cyclohex the chloride is extremely strong and special apparatus of 65 ene, cycloheptene, cyclooctene, indene, styrene, allyl expensive material is required in practice. benzene, allene, methylallene, butadiene, pentadiene, A catalyst system in which an amino acid, a nickel hexadiene, cyclopentadiene, etc.; and acetylene or its compound and a metallic transition metal belonging to alkyl derivatives. 4,138,580 3 4. As the alcohols employed may be mentioned alkyl, In this invention, molecular oxygen may be intro cycloalkyl, aralkyl and acyl mono- or dialcohols. Par duced into the reaction system to increase further the ticularly, aliphatic alcohols such as methanol, ethanol, yield and the selectivity of the desired product. Molecu propanol, butanol, pentanol, hexanol, heptanol, octanol, lar oxygen means oxygen gas, air and other oxygen nonanol, decanol, ethylene glycol, diethylene glycol, containing gases obtained by dilution of oxygen with an propylene glycol, ethylene glycol monoalkyl ether, inert gas such as nitrogen. Usually, the more molecular butane diol, etc., are preferred. Also employed are use oxygen introduced, the greater the yield of the desired ful cyclic alcohols such as cyclopentanol, cyclohexanol, product. However, molecular oxygen should be intro cycloheptanol, phenol, naphthol, cresol, cumenol, xy duced only to such an extent that the gaseous mixture in lenol, benzyl alcohol, 3-phenylethyl alcohol, etc. 10 the reactor is out of explosion limits. As the platinum group metal used as the catalyst, while palladium is the most effective one, platinum, EXAMPLE 1. rhodium, ruthenium, iridium, osmium, etc., are also An autoclave made of stainless steel, equipped with a useful. In applying this invention industrially, it is con magnetic rotary stirrer and having a capacity of 300 ml.
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