Ube Industries, Inc.

Nagoya University

Junichi Kugimoto

Joji Kawai

Hideo Shimomura

Tsunemi Sugimoto

Kazunori Kurosawa

Nobuyuki Kuroda

Mitsuo Yamanaka

Joji Funatsu

Kazuo Yamato

Ryouta Yasumatsu

Nobuhiro Ii

Satoru Fujitsu

Hirofumi Takemoto

Kohei Ninomiya

Hiroshi Matsumoto

Yoshinori Sugimura

Masahide Okada

Takemi Yamamura

Takashi Doi

Masaki Shibuya

Toshihiro Ishikawa

Kazuaki Ishihara

Yasuhisa Fukuda

Nagayoshi Sakamoto

Takato Nakamura

Koji Kaiso

Kouji Kaiso

Yasutaka Tasaki

Osamu Yamazaki

Kouhei Ninomiya

Kohji Kaiso

Yasuhiro Sioji

Ichiro Mikami

Izuhiko Uchida

Naoya Katagiri

Sadao Danno

Wanna Sirisuksukon

Mitsuru Kishishita

Nantariya Ngamsup

Katsuyoshi Kudo

Nobuhiro Il

Tadashi Gotou

A method and a system for inexpensively producing a corresponding target ketone and/or alcohol by decomposing hydroperoxide rapidly and with high selectivity using an aqueous alkaline solution and by recovering and recycling alkali. The method includes neutralizing at least a part of a carboxylic acid in the oxidation reaction solution by contacting the oxidation reaction solution with a first alkaline solution including a carbonate of an alkali metal, and separating the reaction mixture into a first oil phase and a first water phase; decomposing the hydroperoxide and the ester compound in the first oil phase by contacting the first oil phase with a second alkaline solution having a higher pH value than the first alkaline solution, and separating the reaction mixture into a second oil phase and a second water phase; and recovering the carbonate of an alkali metal from the first water phase and recycling the carbonate of an alkali metal to the first alkaline solution.

Method for producing ketone and/or alcohol, and system thereof

This invention provides producing having an objective ketone and/or alcohol by decomposing of a hydrocarbon compound rapidly and selectively having a same number of carbon atoms as a hydrocarbon compound by decomposing a hydroperoxide in a reaction solution obtained from oxidizing the hydrocarbon compound using molecular oxygen of this invention involves, a hydroperoxide decomposition step for decomposing the hydroperoxide into the ketone and/or alcohol by contacting the reaction solution with an aqueous solution containing a carbonate of an alkaline earth metal or a carbonate of an alkali metal and a transition metal compound, a separation step for separating into an oil phase comprising the ketone and/or alcohol, and a water phase comprising the carbonate of an alkaline earth metal or carbonate of an alkali metal and the transition metal compound, a recovery step for recovering the carbonate of an alkali metal or carbonate of an alkaline earth metal and the transition metal compound by combusting the water phase, and a recycling step for recycling to the hydroperoxide decomposition step by dissolving at least the carbonate of the alkali metal or the carbonate of the alkaline earth metal among the recovered substances obtained from the recovery step in water.

This invention relates to a process for producing an oxime comprising reacting a ketone and hydroxylamine in the presence of a carboxylic acid and/or its salt in a system consisting of an aqueous phase and a hydrophobic solvent phase.

Method for producing oxime

A method for producing a high purity, high quality amide compound, particularly a lactam. An amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as a starting material. One or more of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A content of impurities having a cyclic bridge structure is controlled using a cycloalkanone purified by recrystallization.

Method for producing amide compound

A method for producing a high purity, high quality amide compound, particularly a lactam. An amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol% or less based on the ketone as a starting material. One or more of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A content of impurities having a cyclic bridge structure is controlled using a cycloalkanone purified by recrystallization.

The present invention relates to a method for producing a high purity, high quality amide compound, particularly, lactam. A first embodiment of the present invention is characterized in that an amount of each of a halide, an aldehyde compound, an alcohol compound and a nitrile compound contained in a solution recycled into an oxime-forming step is controlled to an amount of 0.4 mol % or less based on the ketone as a starting material. A second embodiment of the present invention is characterized in that one or more compounds selected from the group consisting of a ketone, an oxime and an amide compound are purified by hydrogenation and/or crystallization for eliminating impurities containing a double bond. A third embodiment of the present invention is characterized in that a content of impurities having a cyclic bridge structure is controlled by using a cycloalkanone purified by recrystallization.

The present invention provides novel cyclododecanone-O-azacyclotridecen-2-yloxime and cyclododecanone-O-azacyclotridecen-2-yloxime hydrochloride. The invention also provides a process for producing an amide compound wherein cyclododecanone-O-azacyclotridecen-2-yloxime, hydrogen chloride and/or Lewis acid or cyclododecanone-O-azacyclotridecen-2-yloxime hydrochloride are used as a rearrangement catalyst and/or a reaction starting material in a reaction step.

Compound and process for producing amide compound therewith

This invention relates to a process for producing an amide compound by Beckmann rearrangement of an oxime compound using a compound having at least two electron-withdrawing leaving groups as a rearrangement catalyst, the process comprising a pre-preparation step in which the rearrangement catalyst and at least a part of the oxime compound are mixed and reacted; and a rearrangement reaction step in which the oxime compound is rearranged at a temperature higher than that in the pre-preparation step.

The present invention relates to a process for producing an amide or lactam, particularly laurolactam, wherein catalytic amounts of an acidic chloride and a Lewis acid are used in Beckmann rearrangement of an oxime compound. In accordance with the process, side reactions during Beckmann rearrangement can be so controlled that selectivity can be improved and strong coloring in the reaction can be prevented, giving a high-quality amide or lactam.

Process for producing amide or lactam

The present invention relates to a process for producing laurolactam from cyclododecanone oxime by liquid-phase rearrangement reaction using trichlorotriazine as a rearrangement catalyst. The present invention can provide a process which can solve the problem of termination of the reaction at a certain conversion, can prevent an inactive precipitate generated from trichlorotriazine from precipitating in the course of the reaction process, and can remove an inactive precipitate, an active intermediate and a residual catalyst.

Process for producing laurolactam

Provided is a process for efficiently producing laurolactam by simple steps from cyclododecanone and hydroxylamine. This production process comprises the steps of: (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an oxime-formation solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase; (c) removing a part or all of the oxime-formation solvent and dissolved water from the solution of cyclododecanone oxime which is collected as an oil phase in the oil/aqueous phase separation step, whereby preparing a solution containing a rearrangement solvent to be used in a rearrangement reaction in a later step and the cyclododecanone oxime; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating and removing the rearrangement solvent and the rearrangement catalyst from the reaction mixture after the rearrangement step, and purifying the laurolactam.

Disclosed is a method for producing laurolactam from cyclododecanone and hydroxylamine in a simple process and with high efficiency. The method comprises the following steps (a) to (e): (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an excess amount of cyclododecanone or a solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase as; (c) removing dissolved water from the solution of cyclododecanone oxime which is collected as an oily phase in the oil/aqueous phase separation step; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating the produced laurolactam from the reaction mixture after the rearrangement step and purifying the laurolactam.

After 1,5,9-cyclododecatriene is epoxidized with hydrogen peroxide in the presence of a catalyst containing a tungsten compound, a quaternary onium salt and a mineral acid, to obtain a liquid reaction mixture containing the resultant 1,2-epoxy-5,9-cyclododecadiene, the catalyst, non-reacted hydrogen peroxide and non-reacted 1,5,9-cyclododecatriene and being phase-separated into an oil phase fraction and an aqueous phase fraction, at least the oil phase fraction of the liquid reaction mixture is treated with an aqueous alkali solution to deactivate and remove the non-reacted hydrogen peroxide and the catalyst contained in at least the oil phase fraction.

Refining treatment method of liquid reaction mixture obtained from epoxidation reaction of 1,5,9-cyclododecatriene

An epoxycyclododecane compound is produced by a catalytic hydrogenation reaction of 1,2-epoxy-5,9-cyclododecadiene, using a specific platinum-containing catalyst having a long life, under a hydrogen gas pressure of 0.8 to 9 MPa, and with a high yield of the target compound.

Method of producing an epoxycyclododecane compound

Described is a process for producing 1,2-epoxy-5,9-cyclododecadiene, which comprises bringing 1,5,9-cyclododecatriene into contact with hydrogen peroxide in the presence of a carboxylic acid having an acid dissociation constant K at 25&deg; C. of 5.0&times;10,&lE;K&lE;1.0&times;10,. The present invention makes it possible to provide an industrially desirable process which permits the production of 1,2-epoxy-5,9-cyclododecadiene with good selectivity and facilitates control of reaction including shortening of the reaction time.

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Ube, Japan

Junichi Kugimoto