Daikin Industries, Ltd.

Tsubasa Nakaue

Kazuhiro Takahashi

Daisuke Karube

Takehiro Chaki

Takashi Usui

Tomoyuki Iwamoto

Megumi Kushida

Yuzo Komatsu

Asako Yoshiyama

Yuuko Ito

Tomo Otsuka

Provided is a method for producing an olefin compound using reaction with a base, whereby a target product with a higher purity than the prior art can be obtained. Specifically, provided is a method for producing an olefin compound by reacting a phosphorus-containing olefin compound salt with a base to obtain a dephosphorized and hydrogenated olefin compound, wherein the temperature of the reaction is 50° C. or less.

Olefin compound production method

Provided is a method for purifying a phosphorus-containing olefin compound salt as a raw material or an intermediate that is useful to increase the purity of a target product in a method for producing an olefin compound and that can be applied to the production method, and a method for producing an olefin compound using a purified product obtained thereby. Specifically, provided is a method for purifying a phosphorus-containing olefin compound salt, comprising reprecipitating and/or recrystallizing a solid comprising at least one phosphorus-containing olefin compound salt selected from the group consisting of:

Method for purifying phosphorus-containing olefin compound salt and method for producing olefin compound using purified product obtained thereby

Provided is a method for producing 1,2-difluoroethylene, the method being capable of producing 1,2-difluoroethylene with high selectivity. The method for producing 1,2-difluoroethylene according to the present disclosure comprises performing a dehydrochlorination reaction of 1-chloro-1,2-difluoroethane in the presence or absence of a catalyst. The dehydrochlorination reaction is a gas phase reaction or a liquid phase reaction. The production method according to the present disclosure is capable of producing 1,2-difluoroethylene with high selectivity.

Production method of 1,2-difluoroethylene

A method for efficiently obtaining trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) is provided. The method for producing trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) includes supplying a composition containing trans-1-halo-2-fluoroethylene (E-isomer) and/or cis-1-halo-2-fluoroethylene (Z-isomer) to a reactor to perform isomerization between the trans-1-halo-2-fluoroethylene (E-isomer) and the cis-1-halo-2-fluoroethylene (Z-isomer) in a liquid phase by performing light irradiation in the presence of a photosensitizer.

Method for manufacturing 1-halo-2-fluoroethylene

The present disclosure provides a method for producing HFC-143 at low cost and more efficiently than when using conventional methods. Specifically, the present disclosure provides a method for producing 1,1,2-trifluoroethane (HFC-143), comprising performing one or more fluorination reactions by bringing at least one chlorine-containing compound selected from the group consisting of 2-chloro-1,1-difluoroethane (HCFC-142) and 1-chloro-1,2-difluoroethane (HCFC-142a) into contact with hydrogen fluoride to obtain a reaction gas containing HFC-143, hydrogen chloride, and hydrogen fluoride.

Method for producing 1,1,2-trifluoroethane (HFC-143)

The production method according to the present disclosure comprises obtaining a product containing the fluoroethane from a fluoroethylene by a reaction in the presence of catalysts. Each catalyst is formed by supporting a noble metal on a carrier. A reactor for performing the reaction is filled with a catalyst having a noble metal concentration of C1 mass % based on the entire catalyst and a catalyst having a noble metal concentration of C2 mass % based on the entire catalyst to form an upstream portion and a downstream portion, respectively; and C1&#x3c;C2. The reaction is performed by bringing the fluoroethylene represented by formula (3) and hydrogen gas into contact with the upstream portion and the downstream portion in this order.

Production method for fluoro-ethane and production method for fluoro-olefin

Provided are a method for producing a fluoroethane, which is the desired product, with high selectivity; and a method for producing a fluoroolefin. The production method according to the present disclosure comprises obtaining a product comprising a fluoroethane represented by CXXFCXXX(wherein X, X, X, X, and Xare the same or different and each represents a hydrogen atom, a fluorine atom, or a chlorine atom; and at least one of X, X, X, X, and Xrepresents a hydrogen atom) from a fluoroethylene by a reaction in the presence of at least one catalyst in at least one reactor. The reaction is performed by introducing a starting material gas comprising the fluoroethylene into the reactor, and the water content in the starting material gas is 150 ppm by mass or less based on the total mass of the starting material gas.

Fluoroethane production method and fluoroolefin production method

The production method according to the present disclosure comprises obtaining a product comprising a fluoroethane from a fluoroethylene by a reaction in the presence of at least one catalyst. The reaction is performed in two or more reaction zones. Each reaction zone comprises a catalyst, and the fluoroethylene is supplied to each reaction zone to perform the reaction.

The present disclosure provides a method for producing HFC-143 that is not expensive, and that is more efficient than conventional methods. Specifically, the present disclosure provides a method for producing 1,1,2-trifluoroethane (HFC-143) that includes contacting at least one chlorine-containing compound selected from the group consisting of 1,1,2-trichloroethane (HCC-140), 1,2-dichloro-1-fluoroethane (HCFC-141), 1,1-dichloro-2-fluoroethane (HCFC-141a), (E,Z)-1,2-dichloroethylene (HCO-1130 (E,Z)), and (E,Z)-1-chloro-2-fluoroethylene (HCFO-1131 (E,Z)) with hydrogen fluoride to perform one or more fluorination reactions, thereby obtaining a reaction gas containing HFC-143, hydrogen chloride, and hydrogen fluoride.

The present invention aims to provide an efficient method for obtaining a desired isomer of HFO-1132 from a composition comprising trans-1,2-difluoroethylene (HFO-1132(E)) and cis-1,2-difluoroethylene (HFO-1132(Z)). The present invention provides, as a means for solving the problem, a method for producing HFO-1132(E) and/or HFO-1132(Z), comprising steps (1) to (3): (1) supplying a composition comprising HFO-1132(E) and/or HFO-1132(Z) to a reactor filled with a catalyst to perform an isomerization reaction between the HFO-1132(E) and the HFO-1132(Z); (2) separating the reaction product obtained in step (1) into a first stream comprising the HFO-1132(E) as a main component, and a second stream comprising the HFO-1132(Z) as a main component; and (3) recycling the first stream or the second stream obtained in step (2) to the reactor, to subject the first stream or the second stream to the isomerization reaction.

Method for producing difluoroethylene

The present disclosure provides a method for producing fluoroolefin represented by formula (1): CXX&#x2550;CXX, wherein X, X, X, and Xare the same or different, and represent a hydrogen atom or a fluorine atom, with high selectivity. Specifically, the present disclosure is a method for producing a fluoroolefin represented by formula (1) described above, the method comprising a dehydrofluorination step of bringing a fluorocarbon represented by formula (2): CXXFCXXH, wherein X, X, X, and Xare as defined above, into contact with a metal catalyst to perform dehydrofluorination, the dehydrofluorination step being performed in the gas phase in the presence of water, the concentration of the water being less than 500 ppm relative to the fluorocarbon represented by formula (2).

Method for producing fluoroolefin

The present disclosure provides a method for producing fluoroolefin represented by formula (1): CXX&#x2550;CXX, wherein X, X, X, and Xare the same or different, and represent a hydrogen atom or a fluorine atom, with high selectivity. Specifically, the present disclosure is a method for producing fluoroolefin represented by formula (1), wherein the method includes the step of performing dehydrofluorination by bringing a fluorocarbon represented by formula (2): CXXFCXXH, wherein X, X, X, and Xare as defined above, into contact with a base, and the dehydrofluorination step is performed in the liquid phase at a temperature of &#x2212;70&#xb0; C. or higher to less than 120&#xb0; C.

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Osaka, Japan

Tsubasa Nakaue