Mitsui Toatsu Chemicals, Incorporated

Mitsui Chemicals, Inc.

Hideki Mizuta

Teruyuki Nagata

Masazumi Takaoka

Shinichi Umeda

Hiroshi Naruse

Yukihiro Kumamoto

Masaru Wada

Tohru Miura

Akihiro Tamaki

Masahiko Kusumoto

Hisato Itou

Shoji Tamai

Hisato Itoh

Wataru Yamashita

Hidetoshi Hayashi

Takashi Kuroki

Nobuyuki Kajimoto

Kenichi Goto

Yoriaki Matsuzaki

Katsuji Watanabe

Yasuhiro Takano

Toshiyuki Kataoka

Kunihiro Yamada

Jyoji Morisaki

Yukiko Mori

Kotaro Shimizu

Osamu Kohgo

Kaoru Sakadera

Hiroki Ohnishi

The present invention relates to a novel production method of 4,6-diaminoresorcin, and to 2-sulfonic acid-4,6-dinitroresorcin as its intermediate and salts thereof. The target compound is obtained by (R1) sulfonating resorcin (A) to obtain resorcin 2,4,6-trisulfonate (B), (R2) nitrating the compound (B) to obtain 2-sulfonic acid-4,6-dinitroresorcin (C), (R3) hydrolyzing the compound (C) to obtain 4,6-dinitroresorcin (D), and finally (R4) reducing the compound (D) to obtain 4,6-diaminoresorcin (E):

Production method of 4,6-diaminoresorcin

A process for producing 1,5-diaminonaphthalene without formation of 1,8-diaminonaphthalene and not through an unstable nitro imine and nitro enamine as intermediates, the process including the steps of dehydrogenating 5-substituted-1-tetralone to produce a naphtol compound and then aminating the hydroxyl group of the naphtol compound.

Process for producing 1,5-diaminonaphthalene

A preparation process of N,N&prime;-dialkylalkanediamine by reacting dihaloalkane with lower alkylamine characterized by carrying out the reaction with controlling the residual amount in the reaction system of haloalkaneamine intermediate represented by the formula (4):

Process for the preparation of N,N&prime;-dialkylalkanediamines

In a process for reacting N,N'-dialkylethylenediamine with urea in an aprotic polar solvent to prepare 1,3-dialkyl-2-imidazolidinone, a process comprising progressing the reaction while continuously adding N,N'-dialkylethylnediamine and urea into the aprotic polar solvent. The process is a high-yield manufacturing process in industry capable of efficiently producing very high purity 1,3-dialkyl-2-imidazolidinone which contains less than 0.1% by weight of by-product 1,3-dialkyl-2-imidazolidinimine derived from the raw materials.

High purity 1,3-dialkyl-2-imidazolidinone and preparation process of same

A preparation process of acyl halide or sulfonyl halide which comprises reacting corresponding carboxylic acid or sulfonic acid with a haloiminium salt represented by the general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are same or different lower alkyl groups, X is a halogen atom, and n is an integer of 2 or 3.

Preparation process of acyl halide or sulfonyl halide

The invention provides a novel preparation process of a polycondensation type polymer, an excellent polymer which is represented by lactic acid and the preparation process of the polymer, a polycondensation agent used for the preparation process, and an intermediate. Specifically, the invention provides a preparation process of the polycondensation type polymer, for example, polyamide, polyimide, polythioester and polyester, comprising bonding a carboxyl group comprising compound with an active hydrogen group comprising compound in the presence of haloiminium salt. The invention provides excellent polylactic acid having a controlled D/L-isomer ratio in the repeating structural units and preparation process of polylactic acid, and further provides a haloiminium salt compound used for the preparation process and an intermediate compound of acid chloride.

Process for preparing polycondensation polymer compound

A novel bis-urea compound, preparation process of the compound, and preparation process of 1,3-dialkyl-2-imidazolidinone are disclosed and the disclosure provides a novel preparation process of 1,3-dialkyl-2-imidazolidinone and simultaneously enables effective utilization of N,N',N'-trialkyldiethylentriamine which lacks a large amount use and is desired to develop new application.

Process for producing 1,3-dialkyl-2-imidazolidinone

The present invention relates to 1,3,6-Trialkylhexahydro-1,3,6-triazocine-2-on represented by the formula (1): ##STR1## wherein R is a C.sub.1 .about.C.sub.8 alkyl group and a preparation process of the compound comprising reacting N,N',N'-trialkyldiethylenetriamine represented by the formula (2): ##STR2## wherein R is a C.sub.1 .about.C.sub.8 alkyl group, with urea, phosgene or carbon dioxide.

1,3,6-trialkylhexahydro-1,3,6-triazocine-2-on and preparation process

This invention is an industrially efficient and improved process for the preparation of aliphatic polyisocyanates by using esters as the solvent for converting aliphatic polyamines to isocyanates.

Preparation process of aliphatic isocyanate

A process for preparing cyclohexanonecarboxylic acid compounds by catalytically hydrogenating the corresponding hydroxybenzoic acid compounds in a secondary alcohol or tertiary alcohol solvent.

Process for preparing cyclohexanonecarboxylic acid compounds

A process for the preparation of 4'-hydroxybiphenyl-4-carboxylic acid by reacting a cyclohexanone-4-carboxylic acid compound with phenol in the presence of an acid catalyst, and then subjecting the resulting 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid compound to decomposition and dehydrogenation reactions in the presence of a base and a dehydrogenation catalyst. The aforesaid cyclohexanone-4-carboxylic acid compound is obtained by catalytically hydrogenating a 4-hydroxybenzoic acid compound in a secondary alcohol or tertiary alcohol solvent, and the reaction mixture thus obtained is directly used for the reaction with phenol.

Process for the preparation of 4'-hydroxybiphenyl-4-carboxyl acid

An improved process of producing 1, 3-dialkyl-2-imidazolidinones directly from N, N'-dialkylethylenediamine and urea with a high yield is provided, which process comprises reacting a N, N'-dialkylethylenediamine of the formula ##STR1## wherein R represents --CH.sub.3, --C.sub.2 H.sub.5, --C.sub.3 H.sub.7 or --C.sub.4 H.sub.9, with urea at 180.degree. C. or higher in the presence of a polar solvent, to obtain a 1, 3-dialkyl-2-imidazolidinone of the formula ##STR2## and preferably comprises carrying out the reaction at two stages, that is, the initial period reaction being carried out at 140.degree. C. or lower to from a 1, 1'-dialkyl-1 1'-dimethylenebisurea and successively the latter reaction being carried out at 180.degree. C. or higher.

Process for producing 1, 3-dialkyl-2-imidazolidinone

4-Alkoxyanilines are obtained industrially advantageously by catalytically hydrogenating a nitrobenzene in the presence of a noble metal catalyst in a mixed solvent containing a lower aliphatic alcohol, sulfuric acid, and water or a lower aliphatic carboxylic acid or both to induce hydrogenation and a Bamberger-type rearrangement reaction. The mixed solvent contains at least 10 moles, preferably 30 to 60 moles, of the lower aliphatic alcohol per mole of the nitrobenzene, 1 to 10 moles, preferably 2 to 7 moles, of sulfuric acid per mole of the nitrobenzene, and 2 to 30% by weight, preferably 3 to 10% by weight, of water, the lower aliphatic carboxylic acid or both.

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Fukuoka, Japan

Hideki Mizuta