Mitsubishi Gas Chemical Company, Inc.

Hokkaido University

Other

Toshio Hidaka

Takafumi Yoshimura

Norio Fushimi

Takeshi Kawai

Katsumi Higuchi

Shoji Hara

Tsuyoshi Fukuhara

Makoto Takagawa

Takehiko Takahashi

Yoshifumi Sato

Kazuo Takada

Youichi Kyuuko

Koji Yamamoto

Nobuyuki Koike

Kazuo Tanaka

Kazuhiro Yamada

Takamasa Kawakami

Senzo Shimizu

Toshiyuki Abe

Masaharu Doya

Akira Miyamoto

Hiroka Tanisake

Akifumi Iida

Tomiyoshi Furuta

Emiko Yokose

Satoru Makinose

Yasumitsu Higuchi

Tamotsu Ueno

Yasushi Miki

Masayoshi Okamura

Tetsuo Mizuno

Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small. (In the formula, Ris an alkyl group or an aryl group having substituent(s) of Rf&#x2014;(CH)&#x2014;; Rf is a perfluoroalkyl group; m is from 0 to 2; Rand Reach are an alkyl group or an aryl group.)

Fluoroamine having perfluoroalkyl group, process for producing the same, method of fluorination therewith, and method of recovering amide having perfluoroalkyl group

The present invention provides an industrially available method for efficiently producing high-purity S-(&#x2212;)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid excellent in solid-liquid separability from an S-(&#x2212;)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester, and also provides products obtained by the method. Under a temperature condition of 50-80&#xb0; C. in an aqueous solvent, (A) an S-(&#x2212;)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester represented by the general formula (1) is hydrolyzed under a basic condition for 1-3 hours; then (B) the insoluble matters contained in the reaction solution resulting from the hydrolysis are removed; and (C) an acid is added to the resulting solution to effect crystallization; provided that R in the general formula (1) represents an alkyl or aryl group. 

Method of producing S-(&#x2212;)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid and product obtained by the method

The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an &#x3b1;,&#x3b1;-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R, Rand Reach represents an atom or a group shown in Group 1 to Group 3, and Rrepresents an atom or a group shown in Group 2 or Group 3. Two or more of R, Rand Rmay be bonded to each other to form a ring. Group 1: a hydrogen atom, a halogen atom, a nitro group, a cyano group, a formyl group, a carboxyl group, a sulfonyl group, a sulfinoyl group or a sulfenyl group; Group 2: an alkyl group, which may have an arbitrary substituent, an aryl group or an aralkyl group; and Group 3: an alkyl-substituted, aryl-substituted or aralkyl-substituted oxy group, a carbonyl group, an oxycarbonyl group, a carbonyloxy group, a thio group, a sulfonyl group, a sulfinoyl group or a sulfenyl group) 

Method for producing 2-oxazoline analogue or 1,3-oxazine analogue

A process for producing an &#x3b1;,&#x3b1;-difluoroamine which comprises using hydrogen fluoride and a Lewis base in specific amounts in the halogen-fluorine exchange reaction using an &#x3b1;,&#x3b1;-dihaloamine as the substrate. The process can be industrially applied, enables to obtain the object compound in a short time at a great yield and can be conducted easily with excellent productivity.

Process for producing &#x3b1;, &#x3b1;-difluoroamine

Provided is a production method for an iodine compound in which iodine is reacted with a substrate in the presence of a porous material having a pore diameter of 500 nm or less or in the presence of the above porous material and an oxidizing agent and a production process for high purity 5-iodo-2-methylbenzoic acid comprising an iodination reaction step carried out by the above-mentioned, a crystal precipitation and separation step in which a product is precipitated by adding water or cooling and then separated and a purification step in which crystal separated is recrystallized using an organic solvent. According to the production method for an iodine compound described above, iodine can be introduced into various substrates at a high selectivity. Since expensive metals and specific reagents do not have to be used, it can readily be carried out in an industrially scale, and the product having a high purity can be obtained. Further, the process comprising the iodination reaction, separation and purification steps described above makes it possible to readily obtain at a high yield, 5-iodo-2-methylbenzoic acid having a high purity which is useful in uses for functional chemical products such as medicines. The process of the present invention comprising iodination reaction, separation and purification steps is characterized by that it is simple in terms of a procedure and that the purification load is smaller, and it is very advantageous in industrially carrying out.

Process for production of iodine compounds and process for production of high-purity 5-iodo-2-methylbenzoic acid

The present invention provides a process for producing 5-iodo-2-methylbenzoic acid through iodination of 2-methylbenzoic acid, the process including, as essential steps, a reaction step of iodinating 2-methylbenzoic acid in the presence of a microporous compound, iodine, an oxidizing agent, and acetic anhydride, and a purification step including sublimation, distillation, crystallization, or a combination of two or more of these. According to the present invention, 5-iodo-2-methylbenzoic acid, which is useful for producing functional chemicals such as drugs, can be produced at high purity and high yield in a simple manner. Since the production process includes a simple reaction step and a simple separation/purification step, the load of purification is mitigated. In addition, the microporous compound such as a zeolite catalyst which has been separated and recovered from the reaction mixture can be repeatedly employed after performing of a simple treatment. Thus, the production process ensures a long service life of catalysts and high efficiency.

Process for producing 5-iodo-2-methylbenzoic acid

Provided is a one-step efficient production method for an &#x3b1;,&#x3b1;-difluoroamine of a general formula (1) below from an amide compound. The method is an economical method capable of producing the intended &#x3b1;,&#x3b1;-difluoroamine at high yield by reacting a starting amide compound with carbonyl fluoride and/or oxalyl fluoride under a specific condition. Formula (1) 

Method for producing fluoroamine

The invention provides a process for producing a chroman compound represented by formula (1), characterized in that the process includes allowing a phenol, an unsaturated compound, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc.

Process for producing chroman compound

The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.

High-purity (fluoroalkyl)benzene derivative and process for producing the same

A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes. (wherein X represents a nitrogen or phosphorus atom; R, R, and Rrepresent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R, R, and Rmay be combined with each other to form a ring).

Fluorine compound and fluorinating agent comprising the compound

A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes.(wherein X represents a nitrogen or phosphorus atom; R, R, and Rrepresent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R, R, and Rmay be combined with each other to form a ring).

Catalysts useful for producing methylamines and having practical catalyst life and large selectivity for dimethylamine comprise crystalline silicoaluminophosphate molecular sieves which have a molar ratio of silicon atom to aluminum atom in the range of 0.01-0.30.

Catalysts for producing methylamines and method for manufacturing the same

Catalysts for producing methylamines are provided, which comprise mordenite, as the essential component, of spherical fine particles having a crystal diameter of not more than 0.5 &mgr;m. When the catalysts are used for the production of dimethylamine from methanol and ammonia or through a disproportionation of methylamines, they exhibit a high dimethylamine productivity with the formation of few amount of trimethylamine whose demand is very small. The process can be operated for a long period of time without decrease in the catalyst activity.

Growing community of inventors

Ibaraki, Japan

Toshio Hidaka