公开(公告)号：AU3986485A

公开(公告)日：1985-09-19

申请号：AU3986485

申请日：1985-03-14

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NAGATA TERUYUJI ,  TAMAKI AKIHIRO ,  KAJIMOTO NOBUYUKI ,  WADA MASARU

IPC: C07C209/18 ,  C07C85/06

Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol. The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone. The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product. Hence, it becomes possible to obtain the intended product at a high selectivity from the anilines and phenylenediamines. The process of this invention is an advantageous process for the industrial production of especially the nuclearly substituted diphenylamines.

公开(公告)号：IT8519908D0

公开(公告)日：1985-03-14

申请号：IT1990885

申请日：1985-03-14

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NAGATA TERUYUKI ,  TAMAKI AKIHIRO ,  KAJIMOTO NOBUYUKI ,  WADA MASARU

IPC: C07C209/18 ,  C07C

Abstract: Diphenylamines or N,N'-diphenyl-phenylenediamines can be obtained by heat-reacting an aniline or a phenylenediamine with preferably an excess of a phenol in an amount of 4 to 20 moles per mole of the aniline or phenylenediamine in the presence of a hydrogen transfer catalyst and a cyclohexanone corresponding to said phenol. The excess phenol used in the reaction undergoes reduction in the reaction system to form a cyclohexanone, which in turn reacts with the aniline or phenylenediamine to form a Schiff base and is thus consumed. The Schiff base forms the intended product by means of a dehydrogenation reaction, and the hydrogen evolved at this time reduces the phenol to form a cyclohexanone. The phenol present in excess thus becomes in the system a solvent, a starting material for the cyclohexanone, and an acceptor of the hydrogen that forms as a by-product at the time of formation of the intended product. Hence, it becomes possible to obtain the intended product at a high selectivity from the anilines and phenylenediamines. The process of this invention is an advantageous process for the industrial production of especially the nuclearly substituted diphenylamines.

公开(公告)号：JPH08324110A

公开(公告)日：1996-12-10

申请号：JP27140995

申请日：1995-10-19

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NISHIMURA TAKESHI ,  KAMASHITA TOMOKO ,  WADA MASARU ,  NAGATA TERUYUKI ,  TANABE YOSHIMITSU ,  HASEGAWA KIYOHARU ,  NAKATSUKA MASAKATSU

IPC: B41M5/155 ,  C07C65/10 ,  C09D11/00

Abstract: PURPOSE: To enhance initial and arrival color forming capacity and water resistance by preparing a coupler for a recording material such as pressure-sensitive copy paper from a compsn. containing a polyvalent metal salt of a salicylic acid derivative and sulfonated phenols and/or metal salts thereof. CONSTITUTION: A coupler used in a coupling sheet and good in water resistance and excellent in initial and arrival color forming capacity contains a polyvalent metal salt of a salicylic acid derivative and sulfonated phenols and/or metal salts thereof. The content of phenols or metal salts thereof is set to 0.5-40mol% with respect to the polyvalent metal salt of the salicylic acid derivative and the polyvalent metal salt of the salicylic acid derivative is a polyvalent metal salt of a styrene substituted salicylic acid derivative and sulfonated phenols are styrene substituted sulfonated phenols. This coupler is obtained by reacting styrenes with salicylic acids and phenols to obtain a resin and reacting a polyvalent metal compd. with the resin.

公开(公告)号：JPH08231476A

公开(公告)日：1996-09-10

申请号：JP33005195

申请日：1995-12-19

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NARUSE HIROSHI ,  KIKUCHI CHIYUKI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J23/44 ,  C07B61/00 ,  C07C213/00 ,  C07C217/92

Abstract: PURPOSE: To obtain an alkoxy group-substituted triphenylamine in high yield by suppressing dealkoxylation of a raw material and an intermediate. CONSTITUTION: In reacting an alkoxy group-substituted cyclohexanone with a diphenylamine while forming an alkoxy group-substituted cyclohexanone from an alkoxy group-substituted phenol as a hydrogen acceptor in a system in the presence of a hydrogen transfer catalyst and a catalytic amount of the alkoxy group-substituted cyclohexanone corresponding to the alkoxy group- substituted phenol, a surface supported type catalyst is used as the hydrogen transfer catalyst to provide the objective method for producing the alkoxy group-substituted triphenylamine.

公开(公告)号：JPH08208590A

公开(公告)日：1996-08-13

申请号：JP1494795

申请日：1995-02-01

Applicant: MITSUI TOATSU CHEMICALS

Inventor： HORIBATA TOMOKO ,  KAMASHITA TOMOKO ,  WADA MASARU ,  FUKUMURA KOUKI ,  NAGATA TERUYUKI

IPC: A61K8/30 ,  A61K8/00 ,  A61K8/46 ,  A61Q19/10 ,  B01J31/02 ,  C07B61/00 ,  C07C303/22 ,  C07C309/15 ,  C11D1/28

Abstract: PURPOSE: To efficiently obtain a high-purity N-acyltaurine compound in high yield by using a small amount of solvent. CONSTITUTION: This N-acyltaurine compound is obtained by subjecting a taurine compound of the formula R NHCH2 CH2 SO3 H (R is H, a 1-6C alkyl or cycloalkyl) to salt formation using an organic amine in an aqueous solution or hydrous solvent followed by reaction of the resultant salt with a fatty acid halide of the formula R COX (R CO is an 8-22C saturated or unsaturated fatty acid residue; X is a halogen) in the presence of an organic amine.

公开(公告)号：JPH07278065A

公开(公告)日：1995-10-24

申请号：JP7034594

申请日：1994-04-08

Applicant: MITSUI TOATSU CHEMICALS

Inventor： UCHIDA MASAE ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: C07C209/24 ,  C07B61/00 ,  C07C211/54

Abstract: PURPOSE:To easily produce 3-aminodiphenylamine in high yield and raw material efficiency by using m-dinitrobenzene as a hydrogen acceptor and reacting m-phenylenediamine with cyclohexanone in the presence of a hydrogen-transfer catalyst. CONSTITUTION:This process for the production of 3-aminodiphenylamine in high raw material efficiency comprises the reaction of (A) m-phenylenediamine with (B) cyclohexanone in the presence of (C) a hydrogen-transfer catalyst such as palladium/carrier catalyst in (D) a sulfur-free polar solvent such as DMF using (E) m-dinitrobenzene as a hydrogen acceptor, thereby converting the component E into the reaction raw material component A in the reaction system.

公开(公告)号：JPH07215920A

公开(公告)日：1995-08-15

申请号：JP7173494

申请日：1994-04-11

Applicant: MITSUI TOATSU CHEMICALS

Inventor： UCHIDA MASAE ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J23/44 ,  C07B61/00 ,  C07C209/24 ,  C07C209/28 ,  C07C211/54

Abstract: PURPOSE:To obtain an aminodiphenylamine under an extremely mild condition in high yield by using a nitroaniline as a hydrogen acceptor in reacting a phenylenedimine with cyclohexanone in a polar solvent not containing sulfur in the presence of a hydrogen transfer catalyst. CONSTITUTION:Phenylenediamine is reacted with cyclohexanone in a polar solvent not containing sulfur such as N,N-dimethylformamide or tetramethylurea in the presence of a hydrogen transfer catalyst to give an aminodiphenylamide. In the reaction, a nitroaniline is used as the hydrogen transfer catalyst to promote the reaction. A method for carrying out the reaction while dripping the nitroaniline and cyclohexanone is preferable as the reaction. Especially palladium.carbon or palladium.alumina is preferably used as the hydrogen transfer catalyst. A phenylenediamine formed from the nitroaniline is usable as a raw material in the reaction system and an excessive amount of the phenylenediamine is reusable together with the catalyst in this method.

公开(公告)号：JPH0770003A

公开(公告)日：1995-03-14

申请号：JP13873294

申请日：1994-06-21

Applicant: MITSUI TOATSU CHEMICALS

Inventor： KUSUDA CHIYUKI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J23/44 ,  C07B61/00 ,  C07C209/18 ,  C07C209/26 ,  C07C211/54

Abstract: PURPOSE:To readily produce a diphenylamine having a substituent group on the phenyl group, e.g. by reacting a phenol with ammonia in the presence of a hydrogen transfer catalyst and a cyclohexanone. CONSTITUTION:A diphenylamine of formula III is produced by reacting a phenol of formula II with ammonia in the presence of a hydrogen transfer catalyst and a cyclohexanone of formula I [R is an alkyl, a cycloalkyl, an alkoxy, an aryl or an aryloxy; (n) is 1 to 5] or by converting a part of a phenol of formula II to a cyclohexanone of formula I in the presence of a hydrogen transfer catalyst under pressurized hydrogen and then reacting ammonia therewith using the remaining phenol of formula II as a hydrogen acceptor while forming the cyclohexanone of formula I in the reactional system. The reaction is carried out preferably by supplying ammonia in portions or continuously. The compound of formula III is useful as an anitoxidant for a mineral oil, a synthetic oil, etc., or a resin additive.

公开(公告)号：JPH0770000A

公开(公告)日：1995-03-14

申请号：JP21955293

申请日：1993-09-03

Applicant: MITSUI TOATSU CHEMICALS

Inventor： KUSUDA CHIYUKI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J23/44 ,  C07B61/00 ,  C07C209/26 ,  C07C211/45

Abstract: PURPOSE:To produce a new compound useful as an antioxidant for rubber or a lubricant. CONSTITUTION:An N-(4'-nonylcyclohexyl)-4-nonylanilne of formula I [R1 and R2 are a 6C (branched-chain) alkyls]. The compound of formula I can be produced by hydrogenating a 4-nonylphenol of formula II [R3 is a 6C (branched- chain) alkyll to synthesize a 4-nonylcyclohexanone of formula III (R4 is R3) and reacting the resultant compound of formula III with ammonia in the presence of a hydrogen transfer catalyst such as a palladium catalyst supported on a carrier. In addition, the hydrogen transfer catalyst is used in an amount of 0.001 to 1.0g atm, preferably 0.002 to 0.2g atm in terms of metal atom based on ammonia and the reaction temperature is 80 to 170 deg.C, preferably 100 to 150 deg.C.

公开(公告)号：JPH0761120A

公开(公告)日：1995-03-07

申请号：JP21118893

申请日：1993-08-26

Applicant: MITSUI TOATSU CHEMICALS

Inventor： TANABE YOSHIMITSU ,  KIDA JOTARO ,  HASEGAWA KIYOHARU ,  NAKATSUKA MASAKATSU ,  WADA MASARU ,  FURUYA MASAYUKI

IPC: B41M5/155 ,  C08G61/02

Abstract: PURPOSE:To obtain a polyvalent metal salt of a salicyclic acid resin useful for pressure-sensitive copy paper by reacting a specific salicylic acid derivative, a salicylic esterderivative and a styrene derivative in the presence of an acid and hydrolyzing the obtained reaction product to react the same with a polyvalent metal compd. CONSTITUTION:A salicylic acid derivative represented by first general formula (wherein X1 and X2 are a hydrogen atom, an alkyl group or a halogen atom), a salicylic ester derivative represented by second general formula (wherein R1 is an alkyl group or the like and X3 and X4 are a hydrogen atom, an alkyl group or a halogen atom) and a styrene derivative represented by third general formula (wherein R2-R4 are a hydrogen atom or an alkyl group and X5 and X6 are a hydrogen atom, an alkyl group or a halogen atom) are reacted in the presence of an acid and the obtained reaction product is hydrolyzed to be reacted with a polyvalent metal compd. to produce a polyvalent metal salt of a salicylic acid resin.