Mitsubishi Gas Chemical Company, Inc.

Hokkaido University

Takafumi Yoshimura

Toshio Hidaka

Norio Fushimi

Takeshi Kawai

Yoshifumi Sato

Kazuo Tanaka

Takashi Kojima

Kazuhiro Yamada

Rieko Nakano

Masaharu Doya

Shoji Hara

Yukio Sakai

Tsuyoshi Fukuhara

Yasuhiro Hirai

Masatoshi Yoshimura

Takeshi Uchiho

Masayuki Furutani

Yasuhiro Shoji

Disclosed are a production method for a ubiquinone powder for use in preparations, including Step 1 of compression molding a ubiquinone crystal powder at a linear molding pressure of from 0.6 to 2.5 tons/cm to obtain a compressed fragment; and Step 2 of grinding the compressed fragment obtained in Step 1 to obtain a powder; and a ubiquinone powder for use in preparations, which is obtained by the subject production method. According to the subject production method, it becomes possible to provide a ubiquinone powder for use in preparations for medicines and health foods, which has a high bulk density, a small angle of repose and excellent handling properties and fluidity, without using an additive such as an excipient, a binder and the like.

Production method for ubiquinone powder for use in preparations and product thereof

In reacting an anthranilic acid derivative represented by the general formula (1), especially the anthranilic acid derivative selected from anthranilic acid, anthranilamide and anthranilate, with formamide, the reaction is attained under the condition of coexistence of acetic acid and a base as a catalyst in the reaction liquid, and it has made it possible to produce a quinazolin-4-one derivative represented by the general formula (2) and useful as a material for medicine intermediates, at high yield with no side production.

Method for production of quinazolin-4-one derivative

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

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 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).

A method of producing a phenol compound comprising a step of oxidizing an aromatic aldehyde to an aryl formate and an aromatic carboxylic acid with an oxygen-containing gas, and a step of decomposing the aryl formate to the phenol compound. To facilitate the separation of the aryl formate and the unreacted aromatic aldehyde, a mixture of the aryl formate and the unreacted aromatic aldehyde is recycled to the oxidation process to concentrate the aryl formate in the oxidation mixture. Alternatively, the oxidation process is carried out in an organic solvent having substantially no ability of dissolving water to increase the conversion of the aromatic aldehyde and the selectivity of the aryl formate, thereby producing the aryl formate in a high yield. In another method, the aryl formate is produced by oxidizing the aromatic aldehyde in the organic solvent having substantially no ability of dissolving water with performic acid generated in situ in the reaction system from the reaction between formic acid and hydrogen peroxide. Since the oxidation proceeds in the organic solvent, hydrogen peroxide in aqueous phase contact the aromatic aldehyde. This significantly reduces the amount of explosive cyclic perther and a high-boiling product.

Method of producing phenol compound

The improved phenol derivatives having a phenolic structure as part of the molecular backbone are produced by reacting condensed polycyclic aromatic hydrocarbons, either individually or in combination with unsaturated cyclic aliphatic hydrocarbons, with phenols in the presence of Friedel-Crafts catalysts and have softening points of no more than 150.degree. C., number average molecular weights of 250-800 and phenolic hydroxyl equivalents of 140-850 g/eq. These phenol derivatives are useful either as starting materials for the manufacture of heat-resistant thermosetting resins or as modifiers thereof. They can be produced by reacting the indicated components in the presence of Friedel-Crafts catalysts, typically a mixture of hydrogen fluoride and boron trifluoride, at temperature of 0-350.degree. C.

Phenol derivatives and process for their production

Mesophase pitch that has a softening point of no more than 250.degree. C., a pyridine-insolubles content of no more than 50% and a n-heptane solubles content of 3-10%, with the n-heptane solubles experiencing a weight loss of no more than 15% at 450.degree. C. as measured by thermogravimetry is produced by polymerizing a condensed polycyclic aromatic hydrocarbon or a substance containing it in the presence of HF and BF.sub.3. This mesophase pitch is suppressed satisfactorily in its tendency to smoke during spinning and, additionally, it has a low enough softening point to exhibit outstanding spinnability. Hence, the pitch allows for high-volume spinning to be performed continuously for a prolonged time without causing extensive fouling of the surface of spinning nozzles.

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Niigata, Japan

Takafumi Yoshimura