Sumitomo Chemical Company, Limited

Motoo Hazama

Junko Kudo

Shinzo Seko

Norihiko Hirata

Hideki Ushio

Tooru Tokumaru

Akira Murakami

Yoichi Ikeda

Masaru Ishino

Michio Yamamoto

Naoyuki Takano

Akihiko Nakamura

Gohu Suzukamo

Kiyoshi Ikimi

Yukihiro Honda

Kazushige Okamoto

Masahiko Mizuno

Yoshiki Takashima

Tadatoshi Aratani

Shigefumi Tokumasu

Yoshinori Nakayama

Toshikazu Yagi

Kan Takamine

Takeo Takahashi

Michio Yamato

Nobuhiro Kawara

Maki Okumura

Takanori Ito

Ayumi Inoue

Process for producing optically active azetidine-2-carboxylic acid derivative

Method for purifying pyruvic acid compounds

There is provided a process for producing N-substituted azetidine-.2-carboxylic acid of the formula I: ##STR1## wherein R.sup.1 denotes an aralkyl group or an arylated lower alkoxycarbonyl group and * designates an asymmetric carbon atom, which is characterized by: reacting an N-substituted azetidine-2-carboxylic acid ester of the formula II: ##STR2## wherein R.sup.1 has the same meaning as defined above and R.sup.2 denotes an alkyl group, an aralkyl group or an allyl group, with an enzyme capable of selectively hydrolyzing a stereoisomer based on the carbon atom of the 2-position of the azetidine ring.

Process for producing optically active azetidine-2-carboxylic acid

There is provided a process for producing an optically active N-substituted azetidine-2-carboxylic acid compound represented by the formula (2): ##STR1## by contacting a corresponding N-substituted azetidine-2-carboxylic acid ester of formula (2) with an enzyme derived from a microorganism selected from Arthrobacter SC-6-98-28 strain, Arthrobacter sp. ATCC21908 strain, Chromobacterium SC-YM-1 strain, and a mutant thereof. A process is also provided for preparing an optically active azetidine-2-carboxylic acid by eliminating the N-substituent of a N-substituted azetidine-2-carboxylic acid ester of formula (2).

Process for producing optically active n-substituted azetidine-2

The present invention provides a process for preparing optically active azetidine-2-carboxylic acids using readily available reagents of relatively low price in the industry. Thus, there is provided optically active azetidine-2-carboxylic acid, and a process for producing the same by subjecting optically active N-(alkylbenzyl)azetidine-2-carboxylic acid represented by the formula (1): ##STR1## to hydrogenolysis in the presence of a catalyst.

A method for producing a propargylamine compound represented by the general formula (I): ##STR1## which comprises reacting a propargyl compound represented by the general formula (II): ##STR2## with an aromatic aldehyde represented by the general formula (III):

Method for producing propargylamine compounds

A process is described for the selective decomposition of aromatic primary hydroperoxides by contacting a hydroperoxide mixture containing aromatic primary hydroperoxides and aromatic tertiary hydroperoxides obtained by oxidation of alkylaromatic compounds under non-aqueous conditions with an alkali and an organic aromatic carboxylic acid salt.

Process for treatment of hydroperoxide mixture

There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) reacting the solution of oxygenation products obtained in the step (a) with an organic quaternary ammonium salt and an alkali, or with an organic quaternary ammonium hydroxide, thereby decreasing the content of primary hydroperoxide; (c) subjecting the reaction mixture in the step (b) to decomposition in the presence of a catalyst; and (d) subjecting the decomposition mixture in the step (c) to hydrogenation, thereby obtaining the desired cresols.

Process for production of cresols

There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture. Also disclosed is another process for producing an aromatic amide compound of the general formula (4), including the step of subjecting an o-aminophenol hydrochloride salt of the general formula (6) to condensation with an acid chloride compound having a sulfur content of 0.8% or less, based on the weight of the acid chloride compound, of the general formula (3) in an inert solvent.

Process for producing aromatic amide compounds

There is disclosed a process for the production of cresols, including the steps of: (a) conducting oxygenation of cymene with oxygen gas or an oxygen-containing gas without any addition of an alkali, thereby obtaining a solution of oxygenation products containing tertiary and primary hydroperoxides of cymene; (b) washing the solution of oxygenation products obtained in step (a) with an aqueous alkali solution at a temperature in the range of from 10.degree. to 95.degree. C.; (c) subjecting the solution of oxygenation products obtained in step (b) to hydrogenation at a temperature in the range of from 60.degree. to 100.degree. C. to decrease the content of primary hydroperoxide in such a manner that the weight ratio of primary hydroperoxide to tertiary hydroperoxide is not greater than 1/25 (w/w); (d) subjecting the solution treated in step (c) to decomposition in the presence of a catalyst; and (e) subjecting the solution treated in step (d) to hydrogenation to obtain cresols.

A halogenated alkyl of the formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and each is a lower alkyl group, X is chlorine atom or a bromine atom and Y is a hydrogen atom or a halogen atom is prepared in high conversion and high selectivity by reacting a tertiary halogenated alkyl of the formula: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and X are the same as defined above with an ethylene derivative of the formula:

Process for preparing halogenated alkyl

In a process for the production of 2,3-dimethylbutenes by the dehydrochlorination of 1-chloro-3,3-dimethylbutane in the presence of a catalyst, a conversion of the starting material and selectivity of the desired product can be improved when at least one compound selected from the group consisting of magnesium compounds, calcium compounds and lanthanum compounds is used as the catalyst.

Process for the production of 2,3-dimethylbutenes

A novel optically active cis-4,5-disubstituted imidazolidin-2-one derivative of the formula: ##STR1## wherein R.sup.1 is a C.sub.1 -C.sub.4 alkyl group or benzyl and R.sup.2 is a chiral aralkyl group optionally having at least one of C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy and hydroxyl groups is produced asymmetrically by the reaction of 1,3-dibenzyl-cis-4,5-dicarboxy-imidazolidin-2-one or its anhydride with an optically active secondary amine of the formula: ##STR2## wherein R.sup.1 and R.sup.2 are each as defined above and is transformed into the lactone of 1,3-dibenzyl-cis-4-carboxy-5-hydroxymethyl-imidazolidin-2-one, which is a key intermediate in the synthesis of d-biotin.

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Toyonaka, Japan

Motoo Hazama