Mitsubishi Gas Chemical Company, Inc.

Shinichi Nagao

Hiroshi Ogawa

Mitsuharu Kitamura

Jitsuo Oishi

Ryusuke Shigematsu

Tatsuyuki Kumano

Kenji Nakaya

Akio Hashimoto

Yutaka Matsuura

Junya Nishiuchi

Masayoshi Hayashi

Toru Shishimi

Hiroaki Oka

Yoshitaka Tanaka

Masato Inari

Kinji Kato

Ikutaro Kuzuhara

Hiroshi Machida

Ken Sugito

Tatsuya Utamura

Yukiya Ibi

Shiori Shinagawa

Kuniaki Arasuna

An object of the present invention is to provide a method for producing 2,4-dialkylbenzaldehyde with excellent conversion rate and yield, and excellent regioselectivity for formylation, by allowing carbon monoxide to react on a starting material containing a specific m-dialkylbenzene in the presence of hydrogen fluoride and boron trifluoride. The method for producing 2,4-dialkylbenzaldehyde according to the present invention comprises a step of allowing carbon monoxide to react on a starting material containing m-dialkylbenzene represented by formula (1) in the presence of hydrogen fluoride and boron trifluoride for formylation at least at a position (a), wherein the starting material is a dialkylbenzene containing more than 90 mol % of m-dialkylbenzene represented by formula (1), and the number of moles of boron trifluoride relative to 1 mole of m-dialkylbenzene represented by formula (1) is 0.7 mol or more and 3.0 mol or less:

Method for producing 2,4-dialkylbenzaldehyde

Provided are a novel aldehyde compound suitable for a fragrance and a fragrance ingredient, or a raw material thereof, and a method for producing the aldehyde compound, as well as a fragrance composition containing the aldehyde compound as an active ingredient, and use of the aldehyde compound as a fragrance. A compound represented by Formula (1): where in Formula (1), R is a hydrogen atom or a methyl group.

Aldehyde compound and method for producing same, and fragrance composition

A method for producing tricyclo[5.2.1.0]decane-2-carboxylate according to the present invention is a method for producing tricyclo[5.2.1.0]decane-2-carboxylate, containing reacting tricyclo[5.2.1.0]deca-3-ene in a dilute solution containing the tricyclo[5.2.1.0]deca-3-ene with carbon monoxide in the presence of an acid catalyst, followed by reaction with an alcohol, wherein the dilute solution contains 100 parts by mass or more of a tricyclo[5.2.1.0]decane isomer mixture based on 100 parts by mass of the tricyclo[5.2.1.0]deca-3-ene, the tricyclo[5.2.1.0]decane isomer mixture contains endo-tricyclo[5.2.1.0]decane (Endo form of TCD) and exo-tricyclo[5.2.1.0]decane (Exo form of TCD), and a constituent ratio thereof (Endo form of TCD/Exo form of TCD) is greater than 1.0.

Method for producing tricyclo[5.2.1.02,6]decane-2-carboxylate

A method for separating an alkyl aromatic hydrocarbon, the method having a step of adding a first diluent and an extractant having a superacid to a mixture comprising the alkyl aromatic hydrocarbon and one or more isomers thereof to carry out an acid-base extraction to thereby form a complex of the alkyl aromatic hydrocarbon with the superacid, and thereafter separating the complex from the mixture, and a step of adding an eliminating agent having a relative basicity in a range of 0.06 to 10 with respect to the alkyl aromatic hydrocarbon and a second diluent to the complex, and carrying out complex exchange of the alkyl aromatic hydrocarbon for the eliminating agent to thereby separate the alkyl aromatic hydrocarbon from the complex.

Method and apparatus for separating alkyl aromatic hydrocarbon

Provided is a method for stably and economically producing xylylenediamine with a high yield and long catalyst service life by hydrogenating dicyanobenzene that is obtained by ammoxidating xylene. By bringing an aqueous basic solution into contact with a dicyanobenzene-absorbed liquid, which is obtained by bringing an ammoxidation reaction gas into contact with an organic solvent, under specified temperature conditions, and subjecting a base and a carboxylic acid in the dicyanobenzene-absorbed liquid to a neutralization reaction so as to form an aqueous phase that contains a water-soluble salt, and then subjecting an organic phase and the aqueous phase to liquid-liquid separation so as to remove the aqueous phase, it is possible to remove the carboxylic acid contained in the dicyanobenzene-absorbed liquid with high selectivity while inhibiting loss of the dicyanobenzene. By subjecting the raw material dicyanobenzene, which is obtained by separating low boiling point compounds from the post liquid-liquid separation organic phase by distillation under reduced pressure, to hydrogenation, xylylenediamine is produced with a high yield and the service life of the hydrogenation catalyst is extended.

Method for producing xylylenediamine

The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.

Process for producing xylylenediamine

A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.

Production method of xylylenediamine

To provide a method of purifying 2,7-dimethylnaphthalene comprising the step of bringing a raw oil containing a mixture of 1,7-dimethylnaphthalene and 2,7-dimethylnaphthalene together with a developing solvent into contact with L-type zeolite to thereby effect adsorption of 1,7-dimethylnaphthalene.

Method of purifying 2,7-dimethylnaphthalene

Use of mordenite zeolite and zeolite Y as adsorbents enables a dimethylnaphthalene isomer mixture to be efficiently separated. A feedstock oil containing a dimethylnaphthalene isomer mixture including an &#x3b1;,&#x3b1;-isomer, an &#x3b1;,&#x3b2;-isomer, and a &#x3b2;,&#x3b2;-isomer is passed through an adsorbent layer (A) including mordenite zeolite together with a developing solvent. Subsequently, a liquid discharged from the adsorbent layer (A) is passed through an adsorbent layer (B) including zeolite Y. An eluent is passed through the adsorbent layer (B). The solvent is removed from the resultant eluate to obtain the &#x3b1;,&#x3b2;-isomer of dimethylnaphthalene. Similarly, the &#x3b2;,&#x3b2;-isomer of dimethylnaphthalene is obtained from the adsorbent layer (A).

Method of separating dimethylnaphthalene isomers

A process for producing a high purity aromatic polycarboxylic acid (APA) by purification of a crude APA comprises: (I) aging a slurry of the crude APA in a first dispersion medium at 180 to 300&#xb0; C. for 10 minutes or longer under stirring; (II) introducing the aged slurry of the APA into a column for substituting dispersion media, bringing the slurry into contact with a second dispersion medium and separating the resultant fluid into a fluid of the first dispersion medium containing impurities and a slurry of the second dispersion medium containing crystals of the high purity APA; and (III) separating the crystals of the high purity APA from the slurry of the second dispersion medium. A high purity APA having excellent hue and particle diameter can be industrially advantageously produced while the construction of the process is simplified and the consumption of energy is decreased.

Process for producing a high purity aromatic polycarboxylic acid

A process for producing pyromellitic acid which comprises step A for oxidizing durene, thereby obtaining a reaction mixture comprising trimethyl benzoic acid, trimethyl benzyl alcohol and trimethyl benzaldehyde, step B for separating trimethyl benzoic acid, trimethyl benzaldehyde and trimethyl benzyl alcohol from the reaction mixture obtained in step A, and step C for oxidizing trimethyl benzoic acid and/or trimethyl benzaldehyde separated in step B, thereby obtaining pyromellitic acid.

Process for producing pyromellitic acid

A process for producing trimellitic acid which comprises step A for oxidizing pseudocumene, thereby obtaining a reaction mixture comprising dimethyl benzoic acid, dimethyl benzyl alcohol, and dimethyl benzaldehyde, step B for separating dimethyl benzoic acid, dimethyl benzyl alcohol and dimethyl benzaldehyde from the reaction mixture obtained in step A, step C for oxidizing dimethyl benzyl alcohol separated in step B, thereby obtaining dimethyl benzoic acid and dimethyl benzyl aldehyde and then feeding dimethyl benzoic acid and dimethyl benzyl aldehyde thus obtained to step B, and step D for oxidizing dimethyl benzoic acid and/or dimethyl benzaldehyde separated in step B, thereby obtaining trimellitic acid.

Process for producing trimellitic acid

A process for producing a high purity aromatic polycarboxylic acid by purify a crude aromatic polycarboxylic acid in accordance with the steps of (I) forming an amine salt of an aromatic polycarboxylic acid from the crude polycarboxylic acid and an amine, (II) continuously decomposing the salt in a salt decomposition reactor in operations of (i) supplying an aqueous solution of the amine salt of an organic polycarboxylic acid formed in the step of forming a salt, (ii) removing the amine and water by distillation under heating and (iii) taking out a slurry containing crystallized aromatic polycarboxylic acid, and (III) separating and recovering crystals of the aromatic polycarboxylic acid from the slurry which is taken out in the step of decomposing the salt. A high purity aromatic polycarboxylic acid having excellent hue and large particle diameters can be produced from a crude aromatic polycarboxylic acid industrially with stability at a low cost of production in accordance with a process having a simple construction.

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Kurashiki, Japan

Shinichi Nagao