Central Glass Company, Limited

Satoshi Yoshikawa

Fuyuhiko Sakyu

Yasuo Hibino

Yoshihiko Gotoh

Ryouichi Tamai

Satoru Okamoto

Naoto Takada

Yoshio Nishiguchi

Hideki Oshio

Hideaki Imura

Takeshi Kondo

Kiyoshi Yagii

Katsuyoshi Murata

Naoki Nishinaka

Sadaharu Mishumi

According to an embodiment, a method for producing a (hydro)halocarbon includes a step of purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon. According to another embodiment, a method for producing a (hydro)halocarbon includes a step purifying the (hydro)halocarbon by reduced-pressure distillation of an azeotropic or azeotropic-like composition containing the (hydro)halocarbon and a compound different from the (hydro)halocarbon, wherein standard boiling points of both the (hydro)halocarbon and the compound are 80° C. or lower.

Method for purifying (hydro)halocarbon by reduced pressure distillation from azeotropic or azeotropic-like composition

Provided is a method for causing a dehydrofluorination reaction of 1,1,1,3,3-pentafluoropropane in the gas phase and in the presence of a catalyst thereby producing 1,3,3,3-tetrafluoropropene. In this method, the reaction is carried out at a pressure inside the reaction system of from 0.001 to 90 kPa (absolute pressure) at a reaction temperature ranging from 250 to 600&#xb0; C.

Method for producing 1,3,3,3-tetrafluoropropene

A separation method of 1-chloro-3,3,3-tetraluofopropene and hydrogen fluoride according to the present invention includes reducing the hydrogen chloride content of a mixture containing hydrogen chloride, 1-chloro-3,3,3-tetrafluoropropene and hydrogen fluoride, thereby causing phase separation of the mixture so as to obtain an upper phase predominantly containing the hydrogen fluoride and a lower phase predominantly containing the 1-chloro-3,3,3-tetrafluoropropene. This separation method is industrially economically advantageous since the 1-chloro-3,3,3-tetraluofopropene and the hydrogen fluoride can be separated rapidly by simple operation.

Method for separating 1-chloro-3,3,3-trifluoropropene and hydrogen fluoride, and method for producing 1-chloro-3,3,3-trifluoropropene by using same

A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.

Method for producing cis-1,3,3,3-tetrafluoropropene

According to the first characteristic of the present invention, there is provided a production process for 1,3,3,3-tetrafluoropropene including: the first step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride thereby obtaining 1-chloro-3,3,3-trifluoropropene; and the second step of reacting 1-chloro-3,3,3-trifluoropropene obtained in the first step with hydrogen fluoride in a gaseous phase in the presence of a fluorination catalyst. According to the second characteristic of the present invention, there is provided a dehydration process including bringing 1,3,3,3-tetrafluoropropene containing at least water into contact with zeolite.

Process for producing 1,3,3,3-tetrafluoropropene

A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride, characterized in that the concentrations of respective catalytic components in the 1,1,1,3,3-pentachloropropane as the raw material is controlled to a predetermined level or less. By controlling the concentrations of the respective catalytic components in the 1,1,1,3,3-pentachloropropane to the predetermined level or less, it is possible to improve the problems of shortening of catalyst life, retardation of reaction and scaling or corrosion of equipment in the production of the 1-chloro-3,3,3-trifluoropropene. In addition, the 1,1,1,3,3-pentachloropropane can be obtained selectively with high yield by telomerization reaction of carbon tetrachloride and vinyl chloride. The present invention is thus useful as the method for industrially advantageous, high-yield production of the 1-chloro-3,3,3-trifluoropropene.

Production method for 1-chloro-3,3,3-trifluoropropene

The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a first step of fluorinating 1-chloro-3,3,3-trifluoropropene in a liquid phase by hydrogen fluoride in the presence of an antimony compound as a catalyst, or a second step of fluorinating 1-chloro-3,3,3-trifluoropropene in a gas phase by hydrogen fluoride in the presence of a fluorination catalyst. If the first step is taken, 1,1,1,3,3-pentafluoropropane can be produced with a high yield. If the second step is taken, 1,1,1,3,3-pentafluoropropane can continuously be easily produced. Therefore, the second step is useful for an industrial scale production thereof. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.

Method for producing 1,1,1,3,3-pentafluoropropane

The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes the steps of (a) adding hydrogen fluoride to 1-chloro-3,3,3-trifluoropropene in the presence of an addition catalyst to obtain 1,1,1,3-tetrafluoro-3-chloropropane; and (b) disproportionating the 1,1,1,3-tetrafluoro-3-chloropropane into the 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3,3-dichloropropane, in the presence of a disproportionation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because its steps (a) and (b) are respectively superior in selectivity and yield. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.

The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a step of adding hydrogen fluoride to 1,3,3,3-tetrafluoropropene in a liquid phase in the presence of a hydrohalogenation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because yield of 1,1,1,3,3-pentafluoropropane is high. According to the invention, 1,3,3,3-tetrafluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst, or by another method including a step of reacting 1-chloro-3,3,3-trifluoropropene with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst.

Method for producing 1,1,1,3,3,-pentafluoropropane

The invention relates to a method of preparing a saturated hydrofluorocarbon represented by C.sub.n H.sub.p F.sub.z, by reducing a chlorofluorocarbon or hydrochlorofluorocarbon represented by C.sub.n H.sub.x Cl.sub.y F.sub.z by hydrogen in the presence of a catalyst having palladium and bismuth, wherein 'n' is an integer within a range from 3 to 6, 'x' is an integer within a range from 0 to 2n, each of 'y' and 'z' is an integer within a range from 1 to 2n+1, x+y+z=2n+2 or 2n, p=x+y when x+y+z=2n+2, and p=x+y+2 when x+y+z=2n. The catalyst has a long lifetime in the reduction. According to the invention, conversion of the chlorofluorocarbon or hydrochlorofluorocarbon is high, and the saturated hydrofluorocarbon is prepared with a high yield and a high selectivity.

Method of preparing hydrofluorocarbon

1,1,1,2-Tetrafluoroethane, a refrigerant, is formed with little formation of isomers or chlorofluoroethanes having not very different boiling points by reacting 1,1-dichloro-1,2,2,2-tetrafluoroethane (R-114a), which may contain up to about 25 wt% of 1,2-dichloro-1,1,2,2-tetrafluoroethane (R-114), with hydrogen gas in the presence of a palladium-on-active alumina catalyst at a temperature lower than 200.degree. C. and not lower than 120.degree. C. R-114a almost free of R-114 is obtained by reacting 1,1,1-trichloro-2,2,2-trifluoroethane with hydrogen fluoride in vapor phase in the presence of a catalyst prepared by partially fluorinating .gamma.-alumina by treatment with hydrogen fluoride gas.

Method of preparing 1,1,1,2-tetrafluoroethane from

CF.sub.3 CHCl.sub.2 is easily obtained at good yield by reduction of CF.sub.3 CCl.sub.3 in an aqueous solution of Na.sub.2 SO.sub.3 and an acid acceptor such as hydroxide, carbonate or acetate of an alkali metal or alkaline earth metal. Usually the reduction reaction is carried out at 60.degree.-150.degree. C. under gauge pressure of 0-10 kg/cm.sup.2. The aimed compound can easily be recovered by separating the reaction liquid into organic and aqueous layers, and the waste aqueous solution contains no compound difficult to dispose of.

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Saitama, Japan

Satoshi Yoshikawa