Mitsubishi Gas Chemical Company, Inc.

Agency of Industrial Science and Technology

Seiichi Ishizaka, President of Agency of Industrial Science and

S. Ishizaka, President of Agency of Industrial Science and Technology

Takashi Okawa

Nobuo Isogai

Motoyuki Hosokawa

Natsuko Wakui

Toshiyasu Watanabe

Shuji Ebata

Hideaki Ogino

Takako Takeda

Tomoo Tsujimoto

Yutaka Kanbara

Masaharu Doya

Hideo Igarashi

Yoshinori Kanamori

Natuko Wakui

Hiroshi Matsunaga

Takuji Shitara

Yoshifumi Sato

Ken-ichi Kimizuka

Hideo Ikarashi

Fumisada Kosuge

Toshinari Aoki

Kinya Tsuji

Tomoji Tsuji

Syunsuke Suzuki

Nobuo Ishogai

Nastuko Wakui

A carbocyclic or heterocyclic compound, ammonia and an oxygen-containing gas are subjected to fluid catalytic reaction in vapor phase in the presence of a catalyst containing alkali metal to produce an aromatic or heterocyclic nitrile. The use of the catalyst containing a specific amount of alkali metal enables the stable production of the aromatic or heterocyclic nitrile in high yields with little change with time even when water is present in the reaction system. The use of the catalyst containing the alkali metal also enables the recycle and reuse of unreacted ammonia which is usually accompanied by water, thereby reducing production costs.

Process for producing heterocyclic nitriles

Process for producing carbocyclic nitriles

There is disclosed a process for producing a nitrile compounds by ammoxidation of a carbocyclic or heterocyclic compound having organic substituent(s) by reacting the compound with ammonia and an oxygen-containing gas, wherein unreacted ammonia is recovered from the reaction product gas and recycled to the reaction system.

Process for producing nitrile compounds

Isobutylene glycol is produced with a high yield by catalytically reducing methyl hydroxyisobutyrate in the presence of a catalyst containing at least one of copper and ruthenium. The reduction of methyl hydroxyisobutyrate in the presence of the specific catalyst involves selective reduction of only ester group.

Method of producing isobutylene glycol

There are disclosed a process for producing a nitrile compound which comprises catalytically reacting an alkyl group-substituted aromatic compound or an alkyl group-substituted heterocyclic compound with a mixed gas containing ammonia and oxygen in the presence of 1 a catalyst comprising a vanadium oxide, a chromium oxide, a boron oxide, a molybdenum oxide, and an oxide of an alkali metal or an alkaline earth metal or 2 a catalyst comprising a vanadium oxide, a chromium oxide, a boron oxide, an alkali metal oxide, and a heteropolyacid. According to the above process and by virtue of the specific catalyst, it is made possible to produce a nitrile compound having an aromatic ring or a heterocyclic ring in an extremely advantageous manner, that is, in high yield at high selectivity to the objective product.

Process for producing nitrile compound and catalyst used therefor

Provided a process for producing higher content of trans 1,4-bis(aminomethyl)cyclohexane which is used as the raw material for producing polyamides or polyurethanes having physically and chemically excellent properties from 1,4-bis(aminomethyl)cyclohexane which is generally produced by hydrogenation of p-xylylenediamine. That is, a mixture of cis and trans 1,4-bis(aminomethyl)cyclohexane is isomerized by heating at 120 to 250.degree. C. in the presence of a platinum group catalyst to change to trans isomer. 1,4-bis(aminomethyl)cyclohexane containing more than 80% trans isomer is produced by combining this isomerization technique and crystallization technique.

Process for producing trans 1,4-bis(aminomethyl)cyclohexane

Provided is a process for producing isocyanates from carbamic acid esters which comprises thermally decomposing carbamic acid esters in the presence of a catalyst containing at least one compound selected from the group consisting of organic sulfonic acids and alkaline metal salts of organic sulfonic acids. Thereby, a high thermal decomposition rate can be provided and isocyanate can be obtained in a high yield.

Process for producing isocyanates

A method for the production of an alkylene carbonate at high yields and high selectivity by a reaction between an alkylene glycol and urea, the method being capable to preventing the deposition of a white crystal in the reflux condenser used in a conventional method for the production of alkylene carbonate and the subsequent decrease in the yield, wherein: a gas washing member and a cooling member are disposed above a reaction portion where alkylene glycol and urea are allowed to react, ammonia-containing steam exhausted from the reaction portion is downwardly introduced into the cooling member through the gas washing member, condensate and ammonia gas exhausted from a bottom of the cooling member are gas-liquid separated, the condensate is introduced into the gas washing member, and the ammonia gas is removed from the reaction system.

Method and apparatus for the production of alkylene carbonate

An urethane compound is produced in high yield under mild conditions by reacting a formamide compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst or by reacting an amine compound with dimethyl carbonate in the presence of basic anion exchange resin as a catalyst and methyl formate. Separation and recovery of the catalyst and purification of the urethane compound can be carried out very readily, and since control of water content is not particularly required in this invention, an amine compound and dimethyl carbonate of poor quality can be used.

Process for producing urethane compound

Xylylene diisocyanate is produced in higher space-time yield with higher selectivity by thermal decomposition of xylylene dicarbamate as an urethane compound, i.e. by subjecting the urethane compound to reactive distillation with a thermal decomposition catalyst of at least one of metals selected from antimony and tin or their compounds in the presence of an inert solvent having a higher boiling point than that of the resulting xylylene diisocyanate under reduced pressure of 1 to 500 mmHg and at 150.degree. to 350.degree. C. and then subjecting the resulting reaction products as distillates to partial condensation outside the reactive distillation system, thereby separately recovering the resulting alcohol and xylylene diisocyanate.

Process for producing xylylene diisocyanate

There is disclosed a process for producing an isocyanate compound from a formamide compound or an amine compound which comprises (a) the first reaction step of reacting a formamide compound with dimethyl carbonate in the presence of an alkali catalyst, or reacting methyl formate and an amine compound with dimethyl carbonate in the presence of an alkali catalyst, to produce a corresponding urethane compound, and (b) the second reaction step of thermally decomposing the urethane compound at a temperature of 150.degree.-350.degree. C. and separately recovering the methanol and the corresponding isocyanate compound thus formed.

Process for producing isocyanate compound

A process for producing ethanol which comprises reacting methanol, carbon monoxide and water in the presence of a catalyst comprising cobalt or a cobalt compound and a tertiary phosphine as an effective component is disclosed. A gaseous mixture obtained by burning heavy oil or coal having a relatively high content of carbon can be used as a raw material for producing ethanol.

Process for producing ethanol

A process for producing ethanol which comprises reacting methanol, carbon noxide and hydrogen in the presence of (a) a catalyst containing a cobalt component, an iron component, a ruthenium component and an iodine component, (b) at least one organic solvent and (c) water, said catalyst comprising the cobalt component in amount of 0.1-500 milligram atom (mg-atom) in terms of cobalt per 1 mol of methanol, an iron component in amount of 0.01-4 atoms per 1 atom of cobalt in terms of metal, a ruthenium component in amount of 0.01-4 atoms per 1 atom of cobalt in terms of metal and an iodine component in amount of 0.05-20 atoms per 1 atom of cobalt is disclosed. According to the present invention, selectivity to ethanol is high and ethanol can be obtained under mild conditions.

A process for producing ethanol which comprises reacting methanol, carbon monoxide and hydrogen in the presence of (a) a catalyst comprising cobalt or a cobalt compound and a tertiary phosphine as an effective component and (b) promoter comprising an aromatic carboxylic acid, an ester thereof, or a cobalt salt of aromatic carboxylic acid is disclosed. According to the present invention, formation of by-products becomes less and selectivity to realizable ethanol becomes higher.

Ethanol is prepared with high selectivity from methanol, carbon monoxide and hydrogen by using cobalt phosphate as main catalyst in combination with a platinum group element as co-catalyst or without using such co-catalyst, and further with or without a phosphorus compound. Recovery of the catalyst can be carried out easily.

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Niigata, Japan

Takashi Okawa