Nippon Chemical Industrial Co., Ltd.

Shin-etsu Chemical Co., Ltd.

Hirosaki University

Koizumi Chemical Co., Ltd.

Chiyoda Shoji Co., Ltd.

Masashi Sugiya

Tsutomu Watanabe

Hiroyuki Nohira

Seiji Shimura

Kaoru Takeuchi

Ken Tamura

Tsuneo Imamoto

Natsuhiro Sano

Yoshifusa Hara

Akira Saito

Hiromi Ohsaki

Kazuyuki Asakura

Hideo Sawada

Hiroshi Kawakabe

Katsuhiko Tsunashima

Kunio Kako

Yutaka Demura

Tomio Yanai

An industrially advantageous method for producing an optically active 1,2-bis(dialkylphosphino)benzene derivative of the present invention is provided. The method is characterized in that a phosphine-borane compound represented by the following general formula (1) is subjected to a deboronation reaction, followed by lithiation, then the reaction product is subjected to reaction with an alkyldihalogenophosphine represented by RPX', and thereafter the reaction product is subjected to reaction with a Grignard reagent represented by RMgX&#x2033; to produce an optically active 1,2-bis(dialkylphosphino)benzene derivative (A). Rand Rrespectively represent an alkyl group having 1 to 8 carbon atoms, and the number of carbon atoms is different between Rand R. Ris either Ror Rand Ris the other of Rand R. X, X&#x2032;, and X&#x2033; each represent a halogen atom. 

Method for producing optically active 1,2-bis(dialkylphosphino)benzene derivative

A novel phosphine compound capable of forming a metal complex useful as a catalyst for various asymmetric synthesis reactions, a production method thereof, and a metal complex comprising the aforementioned compound as a ligand.

2, 2'-bis (dialkylphosphino) biphenyl compound, production method thereof, and metal complex comprising the compound as ligand

Powdery silica composite particles obtained by a surface treatment step of adding acid or alkali to a reactant solution comprising: core silica particles of 5 to 200 nm in average particle size; alkoxysilane; a phosphonium salt ionic liquid represented by general formula (1); wherein R, R, and Rrespectively represent a linear or branched alkyl group having 1 to 5 carbon atoms, Rrepresents a linear or branched alkyl group having 1 to 5 carbon atoms, n represents an integer of 1 to 8, and X represents an anionic group; and a reaction solvent such that the alkoxysilane is hydrolyzed, thereby surface-treating the core silica particles.

Powdery silica composite particles and process for producing the same, silica composite particle dispersion, and resin composition

Catalyst for curing epoxy resins, method for making the same, epoxy resin composition, and powder coating composition

1,2-bis(methyl(1,1,3,3-tetramethylbutyl)-phosphino)ethane, process the preparation thereof, transition metal complexes containing the same as a ligand and uses thereof

A method of producing a bisphosphine oxide by performing a koble electrolysis coupling reaction to a phosphine oxide carboxylic acid represented by the general formula (1):

Method of producing bisphosphine oxide

An optically active 1-phenylethylamine is reacted to a phosphine oxide carboxylic acid of a racemic modification shown by the following general formula (2):

Optically active phosphine oxide carboxylic acid and method of producing the same

Reacting a lead tetraacetate with an optically active phosphine oxide carboxylic acid represented by the following general formula (1): ##STR1## in order to obtain an optically active vinyl phosphine oxide represented by the following general formula (2): ##STR2##

Method of producing optically active vinyl phosphine oxide

A phosphonium salt compound having an acryl group which is represented by the following general formula (3) can be made in simple operations: ##STR1## (wherein A represents a alkylene group, Y represents Cl, Br or I, R.sup.1 represents H or CH.sub.3, and R.sup.2, R.sup.3 and R.sup.4 represent a alkyl group having 1-8 carbon atoms, cycloalkyl, aryl, alkaryl or aralkyl group) by reacting an unsaturated aliphatic carboxylic acid halide of the following general formula (1):

Process for preparing a phosphonium salt compound having an acryl group

A highly pure monoalkylphosphine which is useful as a starting material for producing a compound semiconductor, and a method for producing same in high yield are provided. The highly pure monoalkylphosphine is represented by the general formula RPH.sub.2 (wherein R is an alkyl group having 1 to 8 carbon atoms), has a purity of not less than 99.999%, and is substantially free of sulfur and silica. In the method of producing said highly pure monoalkylphosphine, anhydrous hydrofluoric acid is used as a catalyst for a reaction between phosphine and an alkene, and the reaction is carried out in the presence of an organic solvent having a boiling point higher than that of the resulting monoalkylphosphine; the resulting reaction mixture is contacted with an alkali solution so that the remaining catalyst is removed into an aqueous phase in the form of a fluoride salt; next, the obtained reaction mixture is contacted with an alkali hydride and the impurities are removed, then distillation is carried out.

Highly pure monoalkylphosphine and method for producing same

A bis(1,1,3,3-tetramethylbutyl)phosphinic acid compound represented by the formula (1) and an extracting agent using the same for separating Co from an aged electroless Ni plating solution. A di(1,1,3,3-tetramethylbutyl)phosphine is produced by carrying out a reaction between phosphine and trimethylpentene in the presence of an organic solvent and a catalyst, then said phosphine is reacted with an oxydizing agent or sulfur to obtain the compound (1): ##STR1##

Bis (1,1,3,3-tetramethylbutyl) phosphinic acid compound, a production

A highly pure monoalkylphosphine which is useful as a starting material for producing a compound semiconductor, and a method for producing same in high yield are provided. A highly pure monoalkylphosphine represented by the general formula RPH.sub.2 (wherein R is an alkyl group having 1 to 8 carbon atoms) has a purity of not less than five nines, and is substantially free of sulfur and silica. In the method of producing said highly pure monoalkylphosphine, anhydrous hydrofluoric acid is used as a catalyst for a reaction between phosphine and an alkene, and the reaction is carried out in the presence of an organic solvent having a boiling point higher than that of the resulting monoalkylphosphine; the resulting reaction mixture is contacted with an alkali solution so that the remaining catalyst is removed into an aqueous phase in the form of a fluoride salt; next, the obtained reaction mixture is contacted with an alkali hydride and the impurities are removed, then distillation is carried out.

A bis(1,1,3,3-tetramethylbutyl)phosphinic acid compound represented by the formula (1) and an extracting agent using the same for separating Co from an aged electroless Ni plating solution. A di(1,1,3,3-tetramethylbutyl)phosphine is produced by carrying out a reaction between phosphine and trimethylpentene in the presence of an organic solvent and a catalyst, then said phosphine is reacted with an oxidizing agent or sulfur to obtain the compound (1): ##STR1## (wherein X.sup.1 and X.sup.2 are O or S).

Bis(1,1,3,3-tetramethylbutyl) phosphinic acid compound, a production

A method of producing a bis(2-carboxyethyl)-alkyl phosphine oxide represented by the following general formula (1) is disclosed. ##STR1## The method comprises the following Steps 1-4: step 1 wherein phosphine is reacted with acrylonitrile to produce bis(2-cyanoethyl)phosphine and then, in step 2, reacted with an alkene to produce a bis(2-cyanoethyl)alkyl phosphine, and in step 3, reacted with an oxidizing agent to produce a bis(2-cyanoethyl)alkyl phosphine oxide, and in step 4, said bis(2-cyanoethyl)alkyl phosphine oxide is reacted with water or a lower alcohol to give a bis(2-carboxyethyl)alkyl phosphine oxide or a derivative thereof.

Method of producing a bis(2-carboxyethyl)alkyl phosphine oxide and a

A bifunctional alkyl phosphine oxide which is represented by the following general formula (1), ##STR1## wherein R.sup.1 represents tert-butyl or 1,1,3,3-tetramethylbutyl, and a production method thereof. This organophosphorus compound is useful a wide variety of fields including a flame retardant, antistatic additive, antibacterial agent, dyeing-improving agent, resin modifier, stain-proofing agent, and rust preventives. This compound can be produced industrially advantageously.

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Tokyo, Japan

Masashi Sugiya