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公开(公告)号：JPH0692899A
公开(公告)日：1994-04-05
申请号：JP24786792
申请日：1992-09-17
Applicant: MITSUI TOATSU CHEMICALS
Inventor： WATABE YASUYOSHI , MIURA TOSHISUMI , ONO HIROSHI
Abstract: PURPOSE:To selectively produce a para-hydroxybenzoic acid without generation of a salicylic acid or a 4-hydroxyisophthalic acid as a by-product while simplify ing separation and purification by reacting carbon dioxide with a quaternary phosphonium salt of a phenol. CONSTITUTION:A phenol (e.g. phenol) is mixed with toluene and a 40wt.% aqueous solution of tetra-n-butylphosphonium hydroxide is added thereto. The resultant mixture is stirred for 1 hour while blowing nitrogen gas thereinto and then subjected to a dehydration reaction at 88 to 112 deg.C. Toluene is subsequently recovered by heating the reaction mixture and a quaternary phosphonium salt of the phenol is obtained. The resultant compound is then dissolved in dimethylformamide and heated up to 140 deg.C at the ordinary pressure in an atmosphere of nitrogen. Immediately after reaching the temperature, carbon dioxide is introduced and substituted for nitrogen so as to be allowed to react therewith. Thus, the objective para-hydroxybenzoic acid can selectively be produced in a high yield without generation of a salicylic acid or a 4- hydroxyisophthalic acid as a by-product while simplifying the separation and purification process.
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公开(公告)号：JPH03200741A
公开(公告)日：1991-09-02
申请号：JP33820289
申请日：1989-12-28
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI
Abstract: PURPOSE:To obtain 2-hydroxynaphthalene-3-carboxylic acid and 2- hydroxynaphthalene-6-carboxylic acid under a mild condition in high selectivity by reacting alkali metallic salt of 2-naphthol with carbon dioxide in a specific organic phoshine oxide as a solvent. CONSTITUTION:An alkali metallic salt of 2-naphthol is reacted with carbon dioxide in a solvent of one or more organic phoshine oxides shown by the formula (R1 to R3 are 1-8C alkyl, phenyl and preferably R1=R2=R3) preferably at 100-220 deg.C to give 2-hydroxynaphthalene-3-carboxylic acid and 2- hydroxynaphthalene-6-carboxylic acid useful as a dye intermediate or a wholly aromatic polyester-based raw material in high selectively, economically and advantageously in the same manner whether the alkali metallic salt of the raw material is sodium salt or potassium salt.
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公开(公告)号：JPS6317833A
公开(公告)日：1988-01-25
申请号：JP16201286
申请日：1986-07-11
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , ARASHIBA NOBUMASA , MIURA TOSHISUMI
Abstract: PURPOSE:To obtain the corresponding aromatic olefin in high conversion and selectivity, by dehydrating a methylphenylcarbinol in a high concentration in the presence of a porous sulfonic acid type strong acidic cation exchange resin having a specified specific surface area as a catalyst. CONSTITUTION:A methylphenylcarbinol expressed by formula I (R is H or alkyl), e.g. dimethylphenylcarbinol, etc., in >=80% concentration is subjected to dehydration reaction in the presence of a catalyst consisting of a porous sulfonic acid type strong acidic cation exchange resin having >=40m /g specific surface area to afford the aimed corresponding aromatic olefin expressed by formula II, e.g. alpha-methylstyrene, etc., in high conversion and selectivity even in a high concentration. EFFECT:Since troublesome operation after reaction is not required with hardly any formation of dimers or trimers of the aromatic olefin compound and the reaction can be carried out without a solvent, the method is industrially advantageous.
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公开(公告)号：JPH04149150A
公开(公告)日：1992-05-22
申请号：JP26846990
申请日：1990-10-08
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI
Abstract: PURPOSE:To preferentially extract and separate the subject compound from aromatic hydroxycarboxylic acids formed by carboxylating reaction in an organic phosphine oxide solvent by bringing the resultant reaction solution after carrying out the aforementioned reaction into contact with a specific amount of water. CONSTITUTION:An alkali metallic salt of phenol is reacted with carbon dioxide in an organic phosphine oxide as a solvent and the resultant reaction solution containing aromatic hydroxycarboxylic acids is brought into contact with water in an amount of 0.1-10 pts.wt. based on the above-mentioned oxide to preferentially extract a salt of p-hydroxybenzoic acid (PHB) into an aqueous layer in high selectivity at a high concentration. The PHB industrially useful as an intermediate for fine chemicals or a resin raw material is efficiently and selectively separated from the aforementioned produced carboxylic acids. If the second solvent which is a good solvent for the above-mentioned oxide and a poor solvent for water, preferably a saturated hydrocarbon, a saturated aliphatic halogenated hydrocarbon or an aromatic hydrocarbon is further added, separation of the PHB salt is more improved.
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公开(公告)号：JPS62178532A
公开(公告)日：1987-08-05
申请号：JP1679486
申请日：1986-01-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , ONO YUZO , MIURA TOSHISUMI , YAMAZAKI MASAFUMI
Abstract: PURPOSE:To obtain the titled compound useful as a raw material of polycarbonate resin or epoxy resin, etc., in high efficiency, by reacting phenol with a ketone in the presence of a condensation reaction catalyst consisting of a fine- granular and/or powdery strongly acidic ion exchange resin having a specific effective diameter. CONSTITUTION:A fine granular and/or powdery strongly acidic ion exchange resin having an effective diameter of at 0-120 deg.C in the presence of the above catalyst to obtain a bisphenol. The catalyst activity is remarkably improved by the use of the catalyst, the reaction rate is accelerated by decreasing the particle size of the catalyst, the necessary amount of the catalyst to achieve a definite ketone conversion can be reduced and higher ketone conversion can be attained when the same amount of the catalyst is used.
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Patent Agency Ranking
公开(公告)号：JPH02223540A
公开(公告)日：1990-09-05
申请号：JP28759489
申请日：1989-11-06
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI , HASHIMOTO MASAO
Abstract: PURPOSE:To obtain an aromatic hydroxycarboxylic acid rich in p- hydroxybenzoic acid by subjecting an alkali metal salt of phenol and carbon dioxide to carboxylation reaction by using an organic phosphine oxide as a solvent. CONSTITUTION:One of a mixture of an organic phosphine oxide shown by the formula (R1-R3 are 1-8C straight-chain or branched alkyl or phenyl) is used as a solvent, an alkali metal salt of phenol is reacted with carbon dioxide to give an aromatic hydroxycarboxylic acid rich in p-hydroxybenzoic acid. For example, trimethylphosphine oxide or triethylphosphine oxide may be cited as the organic phosphine oxide. By using the solvent, the reaction can be carried out in the same selectivity even in the case of sodium salt of the alkali metal salt of phenol as in the calcium salt and is economically advantageous. The aromatic hydroxycarboxylic acid is useful as an antiseptic, intermediate for agricultural chemical and drugs and a raw material for polyester.
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公开(公告)号：JPH01229033A
公开(公告)日：1989-09-12
申请号：JP5266588
申请日：1988-03-08
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI , OGATA NAOYA
Abstract: PURPOSE:To obtain the title movel polymer outstanding in heat resistance, giving liquid crystal property when dissolved in a specific solvent, thus useful for e.g., liquid crystal display elements, by copolycondensation between p- oxyenzoic acid and a dimethyl-hydroxybenzoic acid in specified proportion. CONSTITUTION:The objective polymer obtained by copolycondensation between (A) p-oxybenzoic acid and (B) 3,5-dimethyl-4-hydroxybenzoic acid in the molar ratio A/B=0.35/0.65-0.65/0.35, with its 10wt.% 0-chlorophenol solution prepared at 50 deg.C having liquid crystal property. This polymer is suggested to be obtained by the following process: a solvent such as nitrobenzene is incorporated with triphenylphosphine oxide and phosgene to form triphenylphosphine dichloride as the catalyst followed by incorporating the resultant catalytic system with the components A and B and carrying out polycondensation in the presence of e.g., triethylamine.
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公开(公告)号：JPS62178533A
公开(公告)日：1987-08-05
申请号：JP1679586
申请日：1986-01-30
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , ONO YUZO , MIURA TOSHISUMI , YAMAZAKI MASAFUMI
Abstract: PURPOSE:To obtain the titled compound from phenol and carbonitrile, by filtering fine granular acidic ion exchange resin catalyst using a filter built in a stirring tank continuous reactor and redispersing the separated fine granular catalyst in the reaction liquid. CONSTITUTION:Phenol is condensed with a carbonitrile compound using a fine- granular acidic ion exchange resin catalyst (preferably obtained by modifying a resin having particle diameter of
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公开(公告)号：JPH059155A
公开(公告)日：1993-01-19
申请号：JP21328191
申请日：1991-08-26
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI
Abstract: PURPOSE:To control the subject ratio in a method for carrying out carboxylation in an organic phosphine oxide solvent by changing a ratio of an organic phosphine oxide and an alkali metal salt of a phenol in a specific range. CONSTITUTION:In a method of reacting an alkali metal salt of a phenol with carbon dioxide in an organic phosphine oxide solvent such as trimethylphosphine oxide, the molar ratio of the organic phosphine oxide solvent to the alkali metal salt of a phenol is changed from 1 to 4, formation ratio of isomers of aromatic hydroxycarboxylic acids is optionally changed and can be controlled in a wide range. This method is industrially advantageous without increasing the amount of by-products.
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公开(公告)号：JPH04334345A
公开(公告)日：1992-11-20
申请号：JP10563791
申请日：1991-05-10
Applicant: MITSUI TOATSU CHEMICALS
Inventor： NAKANISHI TAKEHISA , MIURA TOSHISUMI
Abstract: PURPOSE:To readily separate an alkali metallic salt of an aromatic hydroxycarboxylic acid from a solvent by adding water to a system containing the alkali metallic salt of the aromatic hydroxycarboxylic acid, dissolved or dispersed in an aprotic polar solvent. CONSTITUTION:Water (in a molar amount of preferably about 1-20 times based on an alkali metallic salt of an aromatic hydroxycarboxylic acid) is added into the alkali metallic salt of the aromatic hydroxycarboxylic acid (e.g. a mono-salt of o-hydroxybenzoic acid is dissolved due to a high solubility and its di-salt is mostly suspended and dispersed due to a low solubility) dissolved or dispersed in an aprotic polar solvent to coagulate and precipitate the resultant product. Thereby, the product can readily be separated to afford the aromatic hydroxycarboxylate in the form of a hydrate. The alkali metallic salt of the aromatic hydroxycarboxylic acid can effectively and economically be separated from the solvent according to the aforementioned method which is greatly advantageous to industry.
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