Nippon Shokubai Kagaku Kogyo Co., Ltd.

Nippon Shokubai Co., Ltd.

Other

Youichi Hino

Yuuji Shimasaki

Michio Ueshima

Norihiro Wakao

Ryuichi Ishikawa

Hideaki Tsuneki

Hitoshi Yano

Hideaki Tuneki

Tetsuro Hayashi

Yoshitaka Arita

This invention concerns a novel organic sulfide compound obtained by the reaction of a mercapto alkanol such as 2-mercapto ethanol with an unsaturated amide such as (meth)acrylamide, maleic acid diamide, or fumaric acid diamide and a method for the production of the organic sulfide compound. The invention enables novel organic sulfide compounds of great commercial utility to be obtained with a high yield on a commercial scale.

Organic sulfide compound and method for production thereof

Method for manufacturing thiol compounds

A process for producing an alkylene sulfide, which comprises the step of subjecting a mercaptoalkanol to an intramolecular dehydration reaction in the presence of an acidic dehydration catalyst, to produce the alkylene sulfide, in which the intramolecular dehydration reaction is conducted under at least one conditions of (1) to (3). (1) The intramolecular dehydration reaction is conducted in at least one solvent selected from the group consisting of compounds having an amide group N-substituted with a hydrocarbon group having from 1 to 6 carbon atoms, compounds having an unsubstituted amide group, compounds having a ureylene group N-substituted with a hydrocarbon group having from 1 to 6 carbon atoms, and compounds having an unsubstituted ureylene group. (2) The intramolecular dehydration reaction is conducted in a solvent under such temperature and pressure conditions that the reaction temperature T (.degree.C.) and the boiling point tb (.degree.C.) of the solvent at the reaction pressure satisfy equation (tb-30).ltoreq.T.ltoreq.tb. (3) The intramolecular dehydration reaction is conducted in a solvent in the presence of a hydrocarbon having a boiling point at ordinary pressure of from 30.degree. C. to 180.degree. C. When the hydrocarbon has from 6 to 9 carbon atoms, the above-described effects are enhanced further. When the concentration of the hydrocarbon in the reaction mixture is maintained in the range of from 0.1 to 10% by weight, the above-described effects are enhanced even more.

Process for producing alkylene sulfide

A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines of the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined, in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).

Method of producing ethylenediamines

A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines f the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined, in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).

Catalytic vapor phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5, to convert it into a cyclic amine represented by the general formula ##STR2## wherein R, R' and n are as defined above. The catalyst is an oxide composition represented by the following formula

Vapor-phase intramolecular dehydration reaction of alkanolamines

A catalyst for the vapor phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR1## wherein each of R and R' is selected from hydrogen, a methyl group and an ethyl group, and n is an integer of 2 to 5, to convert it into a cyclic amine represented by the general formula ##STR2## wherein R, R' and n are as defined above. The catalyst is an oxide composition represented by the following formula

Catalyst for vapor-phase intramolecular dehydration reaction of

A catalyst for vapor-phase hydrogen transfer reaction between a carbonyl compound having an alkenyl or aryl group and a primary or secondary alcohol, said catalyst having a composition represented by the following general formula

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Sakai, Japan

Youichi Hino