公开(公告)号：DE69110377T2

公开(公告)日：1995-10-26

申请号：DE69110377

申请日：1991-05-29

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUTAKA ,  KOYAMA SHINICHI

IPC: C07C201/10 ,  C07C205/26 ,  C07C201/00

公开(公告)号：DE69110377D1

公开(公告)日：1995-07-20

申请号：DE69110377

申请日：1991-05-29

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUTAKA ,  KOYAMA SHINICHI

IPC: C07C201/10 ,  C07C205/26 ,  C07C201/00

公开(公告)号：JPH0578285A

公开(公告)日：1993-03-30

申请号：JP7862892

申请日：1992-02-27

Applicant: TAOKA CHEMICAL CO LTD

Inventor： MORINO KAZUKI ,  KOYAMA SHINICHI ,  YAMASHITA MASAYA ,  HORIKAWA YASUHIKO ,  KIMURA OSAMU

IPC: C07C201/10 ,  C07C205/26 ,  C07C309/39

Abstract: PURPOSE:To improve a method for producing 2,4-dichloro-3-methyl or isopropyl-6-nitrophenol useful as an intermediate for cyan color-developing agents for color photographs. CONSTITUTION:A method for producing a 3,5-dichloro-4-alkyl (but excluding ethyl)-2-hydroxybenzene sulfonic acid, characterized by chlorinating a 5-chloro-4- alkyl (but excluding ethyl)-2-hydroxybenzene sulfonic acid in the presence or absence of a catalyst with hydrogen chloride and hydrogen peroxide. For example, the objective 2,4-dichloro-3-alkyl-6-nitrophenol can profitably be produced from a 4-chloro-3-alkylphenol through a 5-chloro-4-alkylphenol-2-hydroxybenzene sulfonic acid and a 3,5-dichloro-4-alkyl-2-hydroxybenzene sulfonic acid in a high purity and in a high yield.

公开(公告)号：JPH04164050A

公开(公告)日：1992-06-09

申请号：JP29325490

申请日：1990-10-29

Applicant: TAOKA CHEMICAL CO LTD

Inventor： HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUKI ,  KOYAMA SHINICHI ,  KIMURA OSAMU

IPC: C07C201/10 ,  C07C205/26

Abstract: PURPOSE:To safely produce the subject compound on an industrial scale in high purity and yield at a low cost by dropping an aqueous solution of 3,5- dichloro-4-ethyl-2-hydroxybenzene-sulfonic acid into an aqueous solution of nitric acid, thereby substituting the sulfonic acid group with nitro group. CONSTITUTION:The subject compound useful as an intermediate for cyan coupler for color photography can be produced on an industrial scale in remarkably improved safety and yield at a low cost with shortened induction period by dropping an aqueous solution of 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid into an aqueous solution of nitric acid having a nitric acid concentration of preferably 2-70wt.%, thereby converting the sulfonic acid group to nitro group. The sulfonic acid is preferably produced by sulfonating 4-chloro-3- ethylphenol and further chlorinating the resultant 5-chloro-4-ethyl-2- hydroxybenzenesulfonic acid.

公开(公告)号：JPH0429966A

公开(公告)日：1992-01-31

申请号：JP22753590

申请日：1990-08-28

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUKI ,  KOYAMA SHINICHI

IPC: B01J27/125 ,  B01J27/128 ,  C07B61/00 ,  C07C201/10 ,  C07C205/26 ,  C07C303/22 ,  C07C309/42

Abstract: PURPOSE:To industrially and advantageously obtain the title compound in high purity and in high yield by chlorinating 5-chloro-4-ethyl-2-hydroxybenzenesulfonic acid with hydrogen chloride and hydrogen peroxide and then replacing the sulfonic acid group with nitro group using nitric acid. CONSTITUTION:5-Chloro-4-ethyl-2-hydroxybenzene sulfonic acid is chlorinated with hydrogen chloride (especially 5-38% aqueous solution of hydrochloric acid) and hydrogen peroxide (especially 5-60% H2O2 solution), preferably in a water solvent to afford 3,5-dichloro-4-ethyl-2-hydroxybenzene sulfonic acid. Then the sulfonic acid group is replaced with nitro group using nitric acid (preferably by dropwise adding an aqueous solution of the above-mentioned benzene sulfonic acid compound to an aqueous solution of nitric acid) to advantageously provide the objective compound useful as an intermediate of cyan color former for color photograph.

公开(公告)号：JPH0421651A

公开(公告)日：1992-01-24

申请号：JP12749390

申请日：1990-05-17

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KOYAMA SHINICHI ,  KIMURA OSAMU ,  YAMASHITA MASAYA ,  MORINO KAZUKI

IPC: B01J27/135 ,  B01J27/138 ,  B01J27/16 ,  C07B61/00 ,  C07C45/54 ,  C07C49/83 ,  C07C49/84

Abstract: PURPOSE:To prepare a polyhydroxybenzophenone compound profitably in a high yield and selectivity by employing an alkane sulfonec acid as a reaction solvent when a phenol compound is made to react with an aromatic carboxylic acid. CONSTITUTION:When a phenol compound of formula (R1, R2 are H, hydroxyl, lower alkoxy) is made to react with an aromatic carboxylic acid of formula II (R3, R4 are H, hydroxyl, lower alkoxy provided that at least one of R3 and R4 is hydroxyl) to prepare a polyhydroxybenzophenone of formula II (e.g. 2,2',4,4'-tetrahydroxybenzophenone), an alkane sulfonic acid (especially methane sulfonic acid) is employed as a reaction solvent. Zinc chloride or tin chloride is used as a catalyst and oxyphosphorus trichloride, etc., may further be employed. The compound of formula III is useful as an intermediate for dyestuffs, agricultural chemicals, drugs, etc.

公开(公告)号：JPH0296545A

公开(公告)日：1990-04-09

申请号：JP24959288

申请日：1988-10-03

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  YAMASHITA MASAYA

IPC: B01J23/02 ,  B01J27/232 ,  C07B61/00 ,  C07C41/00 ,  C07C41/16 ,  C07C43/23 ,  C07C67/00

Abstract: PURPOSE:To safely produce the subject compound in high selectivity for a short time without using any solvent by reacting dihydroxybenzene with ethylene carbonate in the coexistence of a decarboxylation catalyst. CONSTITUTION:Dihydroxybenzene is reacted with ethylene carbonate (preferably in an amount of 0.2-1.5mol, especially 1.5-4.0mol based on 1mol dihydroxybenzene) in the presence of a decarboxylation catalyst of an alkaline metal carbonate, alkaline or alkaline earth metal hydroxide at a temperature within the range of 100-250 deg.C to afford bis(hydroxyethyl)ether of the dihydroxybenzene. The objective compound can be efficiently produced by the above-mentioned method without requiring equipment in which special safety countermeasures are taken for a hydroxyethylating agent.

公开(公告)号：JPH03255044A

公开(公告)日：1991-11-13

申请号：JP26953589

申请日：1989-10-16

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  YAMASHITA MASAYA

IPC: B01J23/02 ,  B01J27/232 ,  C07B61/00 ,  C07C41/16 ,  C07C43/23

Abstract: PURPOSE:To prepare the subject compound in high yield and purity by a safe, simple and profitable preparation method by reacting resorcinol with ethylene carbonate in the presence of a specific decarbonation catalyst at a specified temperature, diluting the reaction product with water and subsequently filtering the formed slurry. CONSTITUTION:Resorcinol is made to react with ethylene carbonate in the presence of an alkali metal carbonate, alkali metal hydroxide or alkaline earth metal hydroxide as a decarbonation catalyst at 100-250 deg.C, preferably at 140-200 deg.C. The reaction product is diluted with water of 0.8-10 times, preferably 1.5-5 times the volumes and the formed slurry is filtered to profitably prepare 1,3-bis(2-hydroxyethoxy) benzene in high yield and high purity, especially without requiring specific installation and reaction solvent. The filtrate or both the filtrate and the washing solvent obtained in the first time reaction are preferably employed as dilution water after the second time reaction.

公开(公告)号：JPH03223235A

公开(公告)日：1991-10-02

申请号：JP23004090

申请日：1990-08-30

Applicant: TAOKA CHEMICAL CO LTD

Inventor： KIMURA OSAMU ,  HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUKI ,  KOYAMA SHINICHI

IPC: B01J27/08 ,  B01J27/125 ,  B01J27/128 ,  C07B61/00 ,  C07C201/10 ,  C07C205/26 ,  C07C303/08 ,  C07C309/02 ,  C07C309/42

Abstract: PURPOSE:To obtain the title high purity compound industrially and advantageously by sulfonating 4-chloro-3-ethylphenol with chlorosulfonic acid in an organic solvent, chlorinating the reaction product and further nitrating the chlorinated substance with nitric acid. CONSTITUTION:4-Chloro-3-ethylphenol which is not required to separate isomers is sulfonated with chlorosulfonic acid in an organic solvent such as a halogenated hydrocarbon to industrially and advantageously give 5-chloro-4- ethyl-2-hydroxybenzenesulfonic acid. Then this compound is chlorinated in a solvent of acetic acid in the presence of sulfur chloride to industrially and advantageously give 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid. Further, this compound is nitrated with nitric acid to industrially and advantageously give high-purity 2,4-dichloro-3-ethyl-6-nitrophenol useful as an intermediate for cyano coupler for color photography.

公开(公告)号：JPH04164049A

公开(公告)日：1992-06-09

申请号：JP29325390

申请日：1990-10-29

Applicant: TAOKA CHEMICAL CO LTD

Inventor： HORIKAWA YASUHIKO ,  YAMASHITA MASAYA ,  MORINO KAZUKI ,  KOYAMA SHINICHI ,  KIMURA OSAMU

IPC: C07C201/10 ,  C07C205/26

Abstract: PURPOSE:To safely produce the subject compound from an aqueous solution of 3,5-dichloro-4-ethyl-2-hydroxybenzenesulfonic acid and an aqueous solution of nitric acid in high purity and yield by reusing a filtrate or water layer obtained by separating the objective compound after nitration reaction. CONSTITUTION:The subject compound useful as an intermediate for a cyan coupler for color photography, etc., is produced by sulfonating preferably 4- chloro-3-ethylphenol, chlorinating the resultant 5-chloro-4-ethyl-2-hydroxybenzenesulfonic acid and nitrating an aqueous solution of the obtained 3,5- dichloro-4-ethyl-2-benzenesulfonic acid with an aqueous solution of nitric acid having an acid concentration of preferably 2-70wt.%. In the above process, the filtrate or water layer obtained by filtering or separating the objective compound produced by the nitration reaction is reused as a part or total of the nitration reaction medium. The induction period can be shortened, the safety and yield can be remarkably improved and the objective compound can be produced on an industrial scale at a low cost by this process.