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United States Patent (19) (11) 4,307,034 Nakayama Et Al

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United States Patent (19) (11) 4,307,034 Nakayama Et Al United States Patent (19) (11) 4,307,034 Nakayama et al. 45) FDec. 22, 1981 54) INERT ORGANIC SOLVENT DISPERSION 52 U.S. Cl. ................................ 260/465 G; 252/309; OF ALKALI. HYDROXDE AND REACTION 260/465 R; 260/465 D; 260/465 F; 260/465 H; USING THE SAME 260/465 K; 260/465.4; 260/465.8 R; 560/51; 560/82; 560/178; 560/190; 562/405; 562/459; 562/489; 562/495; 562/496; 562/590; 562/595; 75) Inventors: Yoshiki Nakayama, Shimizu; Taro 568/316; 568/376; 568/393; 568/433; 568/458; Izawa, Shizuoka; Yasushi Higuchi, 568/459 Shizuoka; Yutaka Ohishi, Shizuoka; 58) Field of Search .......... 260/465 R, 465 G, 465 H, Chihiro Yazawa, Yokohama, all of 260/465.4, 465 F, 465 D, 465 K, 465.8 R; Japan 560/51, 82, 190, 178; 562/489, 495, 496, 590, 595, 405, 459; 568/316, 376, 393, 458, 459, 433 56) References Cited 73) Assignee: Ihara Chemical Industry Co., Ltd., U.S. PATENT DOCUMENTS Tokyo, Japan 3,755,412 8/1973 Taranko et al. ................ 260/465 R 4,012,428 3/1977 Ohno et al. ...... ... 260/465 G 4,062,968 12/1977 Fujimoto et al. ............... 424/304X (21) Appl. No.: 75,314 Primary Examiner-Dolph H. Torrence Attorney, Agent, or Firm-Oblon, Fisher, Spivak, McClelland & Maier 22 Filed: Sep. 13, 1979 57 ABSTRACT An inert organic solvent dispersion of alkali hydroxide is prepared by mixing an alkali hydroxide, an inertor 30 Foreign Application Priority Data ganic solvent and a stabilizer and heating and stirring at the temperature for forming the pasty alkali hydroxide Sep. 26, 1978 JP Japan ................................ 53/118501 and cooling the dispersion. The dispersion of alkali Oct. 30, 1978 JP Japan ................................ 53/133379 hydroxide is used in a reaction of an active methylene Oct. 30, 1978 JP Japan ................................ 53/133380 compound with an organoalkyl halide such as a reac tion of a halophenylacetonitrile with an isopropyl hal ide to obtain ot-isopropyl halophenylacetonitrile. 51) Int. Cl. .................... C07C 121/66; CO7C 53/34; CO7C 55/08; C07C 121/22 8 Claims, No Drawings 4,307,034 1. 2 lene compound with an organoalkyl halide in the pres INERT ORGANIC SOLVENT DISPERSION OF ence of an alkali hydroxide. ALKALI. HYDROXIDE AND REACTION USING (1) The reaction is carried out in the presence of an THE SAME alkali hydroxide (Organic Reactions Vo. 9, page 107). (2) The reaction is carried out in a reaction medium of BACKGROUND OF THE INVENTION an aprotic polar solvent such as dimethylsulfoxide (J. Org. Chem. Vol. 34, pages 226, 1969). 1. Field of the Invention (3) The reaction is carried out in the presence of a The present invention relates to a process for prepar catalyst of a quaternary ammonium salt (Acta. Chem. ing an inert organic solvent dispersion of an alkali hy 10 Scand. Vol. 23, page 2204, 1969; Tetrahedron Lett. Vol. droxide. More particularly, it relates to a process for 15, 1273, 1973; Tetrahedron Vol. 32, page 2235, 1976). preparing an inert organic solvent dispersion of fine One of the important examples of the reaction of the alkali hydroxide particles having a diameter of order of active methylene compound with an organoalkyl halide mu to u such as 100 mu to 500u. is the production of a-isopropyl halophenylacetonitrile. The present invention also relates to a reaction using 15 (1) The reaction is carried out in the presence of a the same. More particularly, it relates to the reaction of condensing agent such as alkali metals, alkali metal an active methylene compound with an organoalkyl alcoholates, alkali metal halides or alkali metal amides halide to produce methylene organoalkylated com (Japanese Unexamined Patent Publication No. pounds useful as intermediates of agricultural chemicals 5350/1975). and medicines. More particularly, it relates to a process (2) The reaction is carried out in the presence of a for producing methylene organoalkylated compounds condensing agent of an alkali hydroxide in a medium of by reacting an active methylene compound with an an aprotic polar solvent such as dimethylsulfoxide and organoalkyl halide in the presence of an alkali hydrox dimethylformamide (Japanese Unexamined Patent Pub ide. lication No. 154217/1975). 2. Description of the Prior Arts 25 (3) The reaction is carried out in the presence of a Heretofore, it has been difficult to obtain fine alkali condensing agent of an alkali hydroxide and a catalyst hydroxide particles because of strong hygroscopic of a quaternary ammonium salt (Japanese Unexamined property of the alkali hydroxide. patent Publication No. 6314.5/1976). On the other hand, an aqueous solution of a base such as alkali hydroxides or carbonates has been used for 30 SUMMARY OF THE INVENTION reactions of a halogenated compound with a compound It is an object of the present invention to provide a having an activated hydrogen atom, such as a condensa process for preparing an inert organic solvent disper tion reaction. sion of fine alkali hydroxide particles having a diameter When an aqueous solution of a base is used for the of 100 mu to 500. condensation reaction such as dehydrohalogenation, 35 It is another object of the present invention to pro the product may be decomposed because of the aqueous vide a process for preparing an inert organic solvent solution of a base. dispersion of alkali hydroxide which is used for a con In order to overcome the problem, it has been consid densation reaction of a halogenated compound with a ered to use a solid base such as alkali hydroxides or compound having an active hydrogen. carbonates. However, alkali hydroxides are hygro The foregoing and other objects of the present inven scopic and are insoluble in an inert organic solvents. tion have been attained by mixing a solid alkali hydrox However, these conventional processes have various ide, and an inert organic solvent and heating and stir disadvantages and are not satisfactory process as the ring the mixture and cooling the mixture in the dis industrial process. persed form. In the process (1), the condensing agent is remarkably 45 The mixture is heated so as to form a pasty alkali reactive with water and accordingly, the activity of the hydroxide in the inert organic solvent. condensing agent is decreased by the contamination of The stirring is carried out so as to form fine particles water to decrease the yield of the object compound. of the alkali hydroxide. The stirring is continued after The explosive reaction may be caused by reacting the starting the cooling. It is preferable to add a stabilizer. condensing agent with water to cause firing. Thus, the 50 The reaction of an active methylene compound with storage and maintenance of the starting materials and an organoalkyl halide is carried out by using the inert the operation for the reaction are quite difficult to be organic solvent dispersion of fine alkali hydroxide disadvantageous. whereby a methylene organoalkylated compound hav In the process (2), the expensive and water soluble ing high purity can be obtained in high yield without aprotic polar solvent such as dimethylsulfoxide is used 55 using an expensive aprotic polar solvent such as di as the solvent. This is not easily recovered. Thus, it is methyl sulfoxide and without a recovery of a catalyst disadvantageous from the economical viewpoint. such as a quarternary ammonium salts. In the process (3), the expensive and water soluble quaternary ammonium salt is used as the catalyst. The DETAILED DESCRIPTION OF THE discharge of the quaternary ammonium salt in a drain 60 PREFERRED EMBODIMENTS age can not be prevented whereby the nitrogen content The dispersion of the alkali hydroxide is prepared by in river, sea or lake is increased to cause the environ using the inert organic solvent which is suitable for mental pollution. Thus, it is disadvantageous from the swelling the alkali hydroxide to form the pasty alkali economical viewpoint. hydroxide in the solvent at the elevated temperature. It The inventors have studied to overcome these disad 65 is preferable to use the inert organic solvent which can vantages of the conventional processes. be used in the atmospheric pressure. The detail of the It has been well-known to produce methylene or operation for the preparation of the dispersion will be ganoalkylated compounds by reacting an active methy described. 4,307,034 3 4 Suitable inert organic solvents include aromatic hy Suitable quaternary ammonium salts include lauryl drocarbons such as benzene, toluene and xylene; halo trimethylammonium chloride and stearyltrimethylam genated aromatic hydrocarbons such as chlorobenzene monium chloride and alkylbenzyldimethylammonium and chlorotoluene; halogenated aliphatic hydrocarbons chloride. such as chloroform and carbon tetrachloride and other Suitable perfluoroalkyl surfactants include per solvents which have boiling point of higher than 100° C. fluoroalkylsulfonate, such as perfluorooctylsulfonate; preferably higher than 120° C. perfluoroalkylsulfonylamine derivatives such as per The stirring operation is easily carried out and the fluorooctylsulfonylamine hydrohalide, perfluorooctyl hygroscopic property of the alkali hydroxide can be sulfonylpropylamine ethyleneoxide adduct and -sul prevented and the formation of fine particles of the O fonylbenzylamine ethyleneoxide adduct. alkali hydroxide can be promoted by stirring and solid The amount of the stabilizer is usually more than alkali hydroxide in said inert organic solvent. 0.0001 wt.% preferably more than 0.001 wt.% espe The amount of the inert organic solvent should be cially more than 0.01 wt.% to the alkali hydroxide. The enough to stir the mixture and is preferably more than 2 stabilizer can be a mixture of said compounds. The times of the alkali hydroxide. 15 stabilizer is to prevent the coagulation of the dispersed The stabilizers can be the compounds having the alkali hydroxide in the inert organic solvent by adsorb formula ing it on the surface of the fine alkali hydroxide particles whereby the formation of fine particles of the alkali hydroxide is improved and to prevent a deposition of 20 the alkali hydroxide on the inner wall of the reactor.
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