Daikin Industries, Ltd.

Takehiro Chaki

Kazuhiro Takahashi

Daisuke Karube

Tsubasa Nakaue

Takashi Usui

Tatsuya Takakuwa

Tomoyuki Iwamoto

Megumi Kushida

Yuzo Komatsu

Yuko Shiotani

Masayuki Kishimoto

Takashi Shibanuma

Shun Ohkubo

Yoshinori Tanaka

Masatoshi Nose

Akinari Sugiyama

Kakeru Hanabusa

Masami Nishiumi

Hitoshi Yoshimi

Yuuko Ito

Masashi Arai

Hitoshi Motoyama

Yuusuke Iwanaga

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

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.

Fluoroolefin production method

The present invention provides a composition comprising an HFO compound, the composition having excellent stability with decomposition and oxidation of the HFO compound being inhibited, the composition having improved refrigerating capacity when used as a heat transfer medium, compared with the case in which an HFO compound is used alone. More specifically, the present invention provides a composition comprising at least one HFO compound selected from the group consisting of HFO-1234yf, (E-/Z-)HFO-1234ze, and (E-/Z-)HFO-1225ye; and a chlorine-containing compound, wherein (1) the chlorine-containing compound is at least one member selected from the group consisting of CH&#x2550;CHCl, CHF&#x2550;CHCl, CH&#x2550;CFCl, CFCl, CHCl, CFCHCl, CClF&#x2550;CHCl, and CHF&#x2550;CCl, and (2) the chlorine-containing compound is contained in an amount ranging from 1 to 500000 mass ppm.

Composition containing hydrofluoroolefin compound

The present invention provides a method for producing a target fluorine-containing olefin with high conversion and selectivity using a process comprising a dehydrofluorination reaction of a hydrofluorocarbon. The method comprises a first reaction step comprising subjecting a hydrofluorocarbon to dehydrofluorination in the presence of a catalyst. The hydrofluorocarbon is a compound represented by Formula (1): RCFYCHZ, wherein Rrepresents a straight or branched Cperfluoroalkyl group, and Y and Z each independently represent H or F wherein when all Zs are H, Y represents F. The catalyst comprises chromium oxide represented by the chemical formula: CrO(1.5&#x3c;m&#x3c;3).

Method for producing fluorine-containing olefin

The present invention provides a method for producing tetrafluoropropene represented by formula (1) by bringing monochlorotrifluoropropene represented by formula (2) into contact with anhydrous hydrogen fluoride in the presence of a catalyst, the method being capable of maintaining the conversion of the starting material and the selectivity for the target product within an excellent range, while reducing degradation of the catalyst to maintain the reaction for a long time. The invention specifically relates to a method for producing tetrafluoropropene represented by formula (1) CFCX&#x2550;CHX wherein Xs are different from each other and represent H or F, including the step of bringing an organic substance containing monochlorotrifluoropropene represented by formula (2) CFCY&#x2550;CHY wherein Ys are different from each other and represent H or Cl into contact with anhydrous hydrogen fluoride in the presence of a catalyst in a reactor, wherein the amount of the anhydrous hydrogen fluoride supplied to the reactor is 30 moles or more per mole of the organic substance supplied to the reactor.

Method for producing tetrafluoropropene

The present invention provides an economically advantageous method for efficiently producing a fluorine-containing compound while ensuring high conversion of the starting compound, reducing production of 245cb, and reducing equipment costs and energy costs. Specifically, the present invention provides a method for producing a fluorine-containing compound represented by Formula (3): CFCFYCHZ(wherein n is 0 or 1, one of Y and Z is H, and the other is F or Cl) by successively reacting at least one chlorine-containing compound selected from the group consisting of chlorine-containing fluoroalkane represented by Formula (1): CXCHClCHCl (wherein X is independently F or Cl, with the proviso that at least one X is F) and chlorine-containing fluoroolefin represented by Formula (2): CXCCl&#x2550;CH(wherein X is independently F or Cl, with the proviso that at least one X is F) with anhydrous hydrogen fluoride in the presence of a fluorination catalyst, wherein the concentration of hydrogen chloride in a reactor inlet gas is not less than 0.01 vol % and not more than 10 vol %.

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Osaka, Japan

Takehiro Chaki