Sumitomo Chemical Company, Limited

Masahiro Hoshino

Keisuke Sugita

Masaru Kitamura

Yuta Kikuchi

Nobufumi Watanabe

Tatsuya Suzuki

Avelino Corma

Hajime Ishida

Sho Tsujiuchi

Koji Kasai

A novel catalyst is provided which enables efficient production of an oxidation product by using an oxygen-induced oxidation reaction of an organic substrate. A novel method of using the catalyst enables efficient manufacturing of the oxidation product by oxidizing the organic substrate using oxygen. A catalyst used in the oxidation reaction of the organic substrate using oxygen contains compound (A), compounds (A) and (B), compounds (A) and (C), compounds (B) and (C), or compounds (A) and (B) and (C). A method for manufacturing the oxidation product using the catalyst involves bringing the organic substrate into contact with oxygen. Compound (A) is an inorganic peroxo acid, a salt of an inorganic peroxo acid, and/or N-halogenated succinimide, compound (B) is a nitroxide and/or a peroxide, and compound (C) is layered silicate.

Catalyst, and method for producing oxidation product

Provided is a method for efficiently producing an oxime, which is a method for producing an oxime by oxidizing, an amine, the method comprising a first contact step and a second contact step, wherein the second contact step is performed by bringing an additional amine into contact with oxygen in the presence of at least a part of an oxidation product obtained in the first contact step.

Method for producing oxime

Provided is a method for producing an oxime compound with satisfactory selectivity. Provide is a method for producing an oxime represented by the following formula (II): wherein Rand Rare respectively the same as defined below, the method including oxidizing an amine represented by the following formula (I): wherein Rand Reach independently represents a hydrogen atom, an optionally substituted hydrocarbon group, or an optionally substituted heterocyclic group (provided that Rand Rare not simultaneously hydrogen atoms), orRand R, together with the carbon atom to which Rand Rare attached, form an optionally substituted alicyclic hydrocarbon group having 3 to 12 carbon atoms [hereinafter sometimes referred to as the amine compound (I)],with oxygen in the presence of a layered silicate.

An object of the present invention is to provide a method capable of producing a cycloalkanol and/or a cycloalkanone with a favorable selectivity coefficient by oxidizing a cycloalkane with a favorable conversion ratio. Disclosed is a method for producing a cycloalkanol and/or a cycloalkanone, which comprises oxidizing a cycloalkane with oxygen in the presence of a mesoporous silica which contains at least one transition metal and has been also subjected to contact treatment with an amine and/or ammonia. Preferably, a crystal obtained by mixing a compound containing the metal, a silicon compound, a structure-directing agent and water is subjected to contact treatment with an amine and/or ammonia and then fired to obtain a mesoporous silica, and a cycloalkane is oxidized with oxygen in the presence of the mesoporous silica.

Method for producing cycloalkanol and/or cycloalkanone

The present invention provides a method for producing cycloalkanol and/or cycloalkanone,

An object of the present invention is to provide a method capable of producing cycloalkanol and/or cycloalkanone with a favorable selectivity by oxidizing cycloalkane with a favorable conversion. A cycloalkanol and/or cycloalkanone are produced by oxidizing cycloalkane with oxygen in the presence of mesoporous silica which contains at least one metal selected from metals of Groups 5 to 10 of the Periodic Table and which is also subjected to a contact treatment with an organosilicon compound. The metal is preferably at least one metal selected from the group consisting of vanadium, chromium, manganese, iron, cobalt, ruthenium and palladium, and the mesoporous silica is preferably MCM-41 type mesoporous silica.

An object of the present invention is to provide a process capable of producing cycloalkanol and/or cycloalkanone with a favorable selectivity by oxidizing cycloalkane with a favorable conversion. Disclosed is a process for producing cycloalkanol and/or cycloalkanone, which comprises oxidizing cycloalkane with oxygen in the presence of mesoporous silica, wherein (1) the mesoporous silica contains at least one transition metal, and (2) a ratio of total volume of mesoporous silica particles having a particle diameter of 20 &#x3bc;m or less to total volume of entire mesoporous silica particles is 25% or more in the mesoporous silica.

Process for producing cycloalkanol and/or cycloalkanone

In case of oxidizing cycloalkane with oxygen, the catalyst to be used is a catalyst obtained by supporting metals of Groups 5 to 10 of the Periodic Table on a carrier, the carrier being subjected to a catalytic treatment with an organosilicon compound. The metal is preferably vanadium, chromium, manganese, iron, cobalt, ruthenium or palladium, while the carrier is preferably an oxide of magnesium, aluminum, silicon, titanium or zirconium.

The invention provides a method for producing &#x3b5;-caprolactam comprising the steps of: a reaction process which subjects cyclohexanone oxime to a Beckmann rearrangement reaction in the presence of a solid catalyst; and a catalyst regeneration process which regenerates the solid catalyst used in the reaction process by heat treatment under an atmosphere comprising an oxygen-containing gas, wherein the solid catalyst heat-treated in the catalyst regeneration process is used in the reaction process, the carbon contents in the solid catalyst in the reaction process and the catalyst regeneration process are maintained in a range of 0.5 to 2% by weight, and the nitrogen contents in the solid catalyst in the reaction process and the catalyst regeneration process are maintained in a range of 0.01 to 0.2% by weight. According to the invention, &#x3b5;-caprolactam can be produced in a high production yield for a long period of time by enhancing persistence of the catalytic activity for producing &#x3b5;-caprolactam.

Method for producing &#x3b5;-caprolactam

The present invention provides a method for manufacturing a zeolite comprising following steps of: According to the present invention, a method is also provided wherein &#x3b5;-caprolactam is manufactured by Beckmann rearrangement reaction of cyclohexanone oxime in a gaseous phase in the presence of the zeolite manufactured by the above-described method.

Method for manufacturing zeolite and method for manufacturing &#x3b5;-caprolactam

A method for producing &#x3b5;-caprolactam and a method for reactivating a zeolite catalyst for the production are provided. In the reactivation step, a zeolite catalyst is allowed to contact a gas containing a carboxylic acid, water and a compound selected from ammonia and amines. In accordance with the present invention, the catalytic activities of a zeolite catalyst used for the Beckmann rearrangement reaction of cyclohexanone oxime can be effectively restored. Consequently, &#x3b5;-caprolactam may be produced with a high production yield for a long period of time by reusing the catalyst by the method described above.

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Niihama, Japan

Masahiro Hoshino