公开(公告)号：JPH0967299A

公开(公告)日：1997-03-11

申请号：JP14938696

申请日：1996-06-11

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NAGATA TERUYUKI ,  HAYASHI HIDETOSHI ,  MIZUTA HIDEKI

IPC: B01J31/02 ,  C07B41/10 ,  C07C51/60 ,  C07C53/42 ,  C07C55/36 ,  C07C57/66 ,  C07C63/10 ,  C07C63/30 ,  C07C65/03 ,  C07C227/18 ,  C07C229/62

Abstract: PROBLEM TO BE SOLVED: To obtain a compound advantageously in terms of economic and environmental aspects by reacting a carboxlic acid with a haloiminium salt. SOLUTION: (A) A carboxlic acid containing a hydroxyl group and/or amino group (e.g. 5-amino-2,4,6-triiodoisophthalic acid) is reacted with (B) a haloiminium salt of the formula (R and R are each a lower alkyl; X is a halogen; (n) is 2 or 3) (e.g. 2-chloro-1,3-dimethylimidazolium chloride). The amount of the component B used based on the component A is equal to or more than stoichiometric amount (especially preferably 1.1-1.3 times as much as the stoichiometric amount of the compound A). The reaction is carried out at room temperature to 70 deg.C for several hours to tens hours. Lauric acid chloride may be cited as the compound.

公开(公告)号：JPH07291949A

公开(公告)日：1995-11-07

申请号：JP1772495

申请日：1995-02-06

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NARUSE HIROSHI ,  MIZUTA HIDEKI ,  UMEDA SHINICHI ,  NAGATA TERUYUKI

IPC: C07D255/02

Abstract: PURPOSE:To obtain the novel compound presenting excellent solvent effect, also excellent in oxidation resistance at elevated temperatures, an aprotic polar solvent useful as a solvent for high-molecular compounds or organic reactions. CONSTITUTION:The compound of formula I (R is a 1-8C alkyl), e.g., 1,3,6- trimethylhexahydro-1,3,6-triazocin-2-one. The compound of the formula I is obtained by reaction between (A) a compound of the formula II prepared, in advance, by reaction of a 1,2-dihalogenoethane with an amine of formula R-NH2 and (B) urea; specifically, a urea intermediate is formed at >=160 deg.C in the initial reaction, and the subsequent decomposition of the urea intermediate is conducted at a raised temperature of >=200 deg.C; and the molar ratio A/B is set at 1.2 to 1.7 in this reaction.

公开(公告)号：JPH069511A

公开(公告)日：1994-01-18

申请号：JP16593692

申请日：1992-06-24

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIZUTA HIDEKI ,  NISHIMURA TAKESHI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J31/02 ,  C07B61/00 ,  C07C209/36 ,  C07C209/86 ,  C07C211/51

Abstract: PURPOSE:To readily obtain high-purity m-phenylenediamine hardly coloring with the lapse of time in high yield by using crude m-dinitrobenzene containing o- and p-isomers as a starting material. CONSTITUTION:Crude m-DNB containing o- or p-DNB is made to react with phenols of formula I and/or formula II (R is H, halogen, OH, alkyl, NH , alkoxy, carboxyl, phenol, etc.; m is 1-5; n is 1-4; X is 1-10C divalent hydrocarbon group, C(CF3)2, CO, S, SO, O, N=N, NH, single bond, etc.) in the presence of a basic compound (preferably sodium hydroxide) and as necessary, a phase transfer catalyst combinedly used to substantially convert only o- and p-DNB into corresponding phenoxynitrobenzenes. Then the resultant reaction mixture is subjected to hydrogenation reaction without separating m-DNB from the reaction mixture and the resultant m-phenylenediamine is separated by distillation. Phenoxyaniline produced by hydrogenation is left as a kettle residue when distilled.

公开(公告)号：JPH05331113A

公开(公告)日：1993-12-14

申请号：JP13680492

申请日：1992-05-28

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIZUTA HIDEKI ,  NISHIMURA TAKESHI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J31/02 ,  C07B61/00 ,  C07C209/36 ,  C07C209/54 ,  C07C211/51

Abstract: PURPOSE:To obtain high-purity m-phenylenediamine with hardly any change with time, simultaneously remarkably reduce the amount of an alcohol used and improve the productivity at the same time. CONSTITUTION:The method for producing m-phenylenediamine is characterized by reacting crude dinitrobenzene containing o- and p-dinitrobenzenes with a lower alcohol in the presence of a basic compound and a phase-transfer catalyst to provide a reactional mixture, directly subjecting the resultant reactional mixture to hydrogenating reaction without separating the m-dinitrobenzene therefrom and then separating the obtained m-phenylenediamine by distillation.

公开(公告)号：JPH05331109A

公开(公告)日：1993-12-14

申请号：JP13680392

申请日：1992-05-28

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIZUTA HIDEKI ,  NISHIMURA TAKESHI ,  WADA MASARU ,  NAGATA TERUYUKI

IPC: B01J31/02 ,  C07B61/00 ,  C07C201/16 ,  C07C205/11

Abstract: PURPOSE:To obtain purified high-purity m-dinitrobenzene in high yield, simultaneously remarkably reduce the amount of an alcohol used and improve the productivity. CONSTITUTION:The method for purifying m-dinitrobenzene is characterized by substantially selectively reacting only the o- and p-isomers of crude m- dinitrobenzene with a lower alcohol in the presence of a basic compound and a phase-transfer catalyst and separating o- and p-alkoxynitrobenzenes from the resultant reactional mixture.

公开(公告)号：JPH0443900B2

公开(公告)日：1992-07-20

申请号：JP22886084

申请日：1984-11-01

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NAGATA TERUYUKI ,  TAMAOKI AKIHIRO ,  OONISHI HIROKI ,  MIZUTA HIDEKI

IPC: C07B61/00 ,  B01J23/00 ,  B01J23/40 ,  C07C67/00 ,  C07C213/00 ,  C07C217/84

公开(公告)号：JPH03232841A

公开(公告)日：1991-10-16

申请号：JP2857390

申请日：1990-02-09

Applicant: MITSUI TOATSU CHEMICALS

Inventor： NAGATA TERUYUKI ,  WADA MASARU ,  MIZUTA HIDEKI

IPC: C07C201/12 ,  C07C205/37

Abstract: PURPOSE:To obtain the subject compound without using purification process by reacting 4-chloronitrobenzene with ethanol in the presence of an alkali metal hydroxide using 1,3-dimethyl-2-imidazolidinone as a reaction solvent. CONSTITUTION:4-Chloronitrobenzene is made to react with ethanol in the presence of an alkali metal hydroxide using 1,3-dimethyl-2-imidazolidinone as a reaction solvent. The reaction is preferably carried out in the presence of an oxygen-containing gas at 30-100 deg.C. 4-Nitrophenetole produced by the process can be used without purification such as recrystallization and is useful as a raw material for the production of 4-phenetidine by catalytic hydrogenation. The process is industrially advantageous and the product is extremely useful as an intermediate for dyes, agricultural chemicals and pharmaceuticals.

公开(公告)号：JPS63190853A

公开(公告)日：1988-08-08

申请号：JP7181487

申请日：1987-03-27

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIURA TORU ,  NAGATA TERUYUKI ,  MIZUTA HIDEKI

IPC: C07C67/343 ,  B01J23/44 ,  C07B61/00 ,  C07C51/347 ,  C07C51/353 ,  C07C51/373 ,  C07C62/24 ,  C07C62/32 ,  C07C65/24 ,  C07C69/753

Abstract: PURPOSE:To obtain the titled compound useful as a raw material for polymers, etc., rapidly and in high yield without producing by-products, by catalytically hydrogenating a 4-hydroxybenzoic acid in a secondary or tertiary alcohol and then reacting the reaction product with phenol in the presence of an acid catalyst. CONSTITUTION:A 4-hydroxybenzoic acid shown by formula I (R is H or lower alkyl) is catalytically hydrogenated in a secondary alcohol or tertiary alcohol to give a reaction mixture containing a cyclohexanone-4-carboxylic acid shown by formula II. Then this mixture is reacted with phenol in the presence of an acid catalyst (e.g. Pd-carbon, nickel catalyst, etc.) to give a 4,4-bis(4- hydroxyphenyl)-cyclohexanecarboxylic acid ester shown by formula III, which is further decomposed and dehydrogenated in the presence of a base and a dehydrogenating catalyst to give a 4'-hydroxybiphenyl-4-carboxylic acid.

公开(公告)号：JPS63152338A

公开(公告)日：1988-06-24

申请号：JP7181387

申请日：1987-03-27

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIURA TORU ,  NAGATA TERUYUKI ,  MIZUTA HIDEKI

IPC: C07C69/75 ,  B01J23/44 ,  C07B61/00 ,  C07C51/373 ,  C07C62/24 ,  C07C67/303 ,  C07C67/39 ,  C07C67/42 ,  C07C69/95

Abstract: PURPOSE:To obtain the titled substance useful as a perfumery enhancer, etc., in high yield at high rate of reaction while suppressing side-reactions, by catalytically hydrogenating hydroxybenzoic acids in a secondary or tertiary alcohol solvent. CONSTITUTION:The objective compound of formula II can be produced by hydrogenating a compound of formula I (R is H or 1-3C alkyl) in a secondary or tertiary alcohol solvent in the presence of a catalyst such as Pd-C under hydrogen pressure of 2-30kg/cm at 80-200 deg.C. Among the above alcohols, isopropyl alcohol is most preferable in view of suppressing effect of by-products, separation and recovery of the product after the reaction, etc. The amount of the solvent is preferably 1-3pts.wt. per 1pt.wt. of the compound of formula I.

公开(公告)号：JPS6314756A

公开(公告)日：1988-01-21

申请号：JP15870786

申请日：1986-07-08

Applicant: MITSUI TOATSU CHEMICALS

Inventor： MIURA TORU ,  NAGATA TERUYUKI ,  MIZUTA HIDEKI

IPC: C07B61/00 ,  C07C51/353 ,  C07C65/24

Abstract: PURPOSE:To obtain a compound useful as a raw material for polymers and intermediate for liquid crystal compounds in high purity and yield, by reacting a cyclohexanone-4-carboxyic acid ester with phenol in the presence of an acid catalyst. CONSTITUTION:A cyclohexanone-4-carboxylic acid ester expressed by formula I (R is lower alkyl) is reacted with phenol in the presence of an acid catalyst, e.g. hydrochloric acid, at 30-100 deg.C to give a mixture of a 4,4-bis(4- hydroxyphenyl)-cyclohexanecarboxylic acid ester expressed by formula II with 4,4-bis(4-hydroxyphenyl)-cyclohexanecarboxylic acid. The resultant mixture is then reacted in the presence of a base, e.g. NaOH, preferably in the coexistence of a hydrogen acceptor, e.g. alpha-methylstyrene, at 100-400 deg.C to afford the aimed substance.