EP0436031A1 - Procede de production d'un dichloropentafluoropropane - Google Patents

Procede de production d'un dichloropentafluoropropane

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Publication number
EP0436031A1
EP0436031A1 EP90910909A EP90910909A EP0436031A1 EP 0436031 A1 EP0436031 A1 EP 0436031A1 EP 90910909 A EP90910909 A EP 90910909A EP 90910909 A EP90910909 A EP 90910909A EP 0436031 A1 EP0436031 A1 EP 0436031A1
Authority
EP
European Patent Office
Prior art keywords
reaction
conducted
tetrafluoroethylene
catalyst
reactor
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP90910909A
Other languages
German (de)
English (en)
Inventor
Shinsuke 3-7-1-603 Namiki Kanazawa-Ku Morikawa
Shunichi Samejima
Keiichi 62 Kuritaya Kanagawa-Ku Ohnishi
Hidekazu 2-59-1 Tsurugamine Asahi-Ku Okamoto
Takashi Ohmori
Toshihiro 2-24-31 Konan Konan-Ku Tanuma
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AGC Inc
Original Assignee
Asahi Glass Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP1187523A external-priority patent/JP2738042B2/ja
Priority claimed from JP21755389A external-priority patent/JP2734669B2/ja
Priority claimed from JP21755489A external-priority patent/JP2734670B2/ja
Priority claimed from JP21755589A external-priority patent/JP2734671B2/ja
Priority claimed from JP26309889A external-priority patent/JP2849129B2/ja
Application filed by Asahi Glass Co Ltd filed Critical Asahi Glass Co Ltd
Publication of EP0436031A1 publication Critical patent/EP0436031A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
    • C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
    • C07C19/12—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine having two carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C19/00—Acyclic saturated compounds containing halogen atoms
    • C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine

Definitions

  • the present invention relates to a process for producing a dichloropentafluoropropane (R225) such as 3,3-dichloro-l,l,l,2,2-pentafluoropropane (R225ca) or l,3-dichloro-l,l,2,2,3-pentafluoropropane (R225cb).
  • R225 dichloropentafluoropropane
  • Such a dichloropentafluoropropane is expected to be useful as a foaming agent, a cooling medium or a cleaning agent like conventional chlorofluorocarbons (CFC S ).
  • the present invention has been accomplished on the basis of this discovery.
  • trichlorofluoromethane Rll
  • tetrafluoroethylene 4F
  • trichloropentafluoropropanes such as 1,1,3- trichloro-1,2,2,3,3-pentafluoropropane (R215ca) and l,l,l-trichloro-2,2,3,3,3-pentafluoropropane (R215cb) are obtained in good yield.
  • R215ca and R215cb formed by this addition reaction vary depending upon the catalyst and reaction conditions employed.
  • the Lewis acid catalyst useful for the reaction of the present invention it is possible to employ a halide containing at least one element selected from the group consisting of B, &£ , Ga, In, Fe, Ni, Co, Sb, Nb, Sn, Ti, Zr, W, Hf and Ta, such as a chloride, e.g. BC ⁇ 3 , A£C4 3 , GaC- ⁇ ?
  • the reaction can be conducted in an inert solvent such as perfluorooctane or perfluorobutyltetrahydrofuran. However, to make the purification easy, it is usually preferred to conduct the reaction in the absence of any solvent.
  • the catalyst is used usually in an amount of from 0.01 to 50% by weight, preferably from 0.1 to 10% by weight, relative to the starting material.
  • the reaction temperature is usually within a range of from -80 to 200°C, preferably from -20 to 100°C, and the reaction pressure is usually from 0 to 20 kg/cm , preferably from 0 to 10 kg/cm 2 .
  • 4F is used usually 1.0 to 1.5 times the molar quantity of Rll.
  • the Lewis acid catalyst is usually used in an amount of from 0.1 to 50 weight%, preferably from 0.1 to 10 weight%, relative to Rll.
  • the reduction of trichloropentafluoropropane (R215) obtained by this reaction can be conducted by using various reducing methods such as a method of conducting the reduction under irradiation, a method for conducting the reduction by means of zinc, or a method for conducting the reduction by using hydrogen in the presence of a catalyst, whereby dichloropentafluoropropane (R225), such as 3,3-dichloro- 1,1,1,2,2-pentafluoropropane (R225ca) or 1,3-dichloro- 1,1,2,2,3-pentafluoropropane (R225cb) can be obtained.
  • dichloropentafluoropropane R225
  • R225ca 3,3-dichloro- 1,1,1,2,2-pentafluoropropane
  • R225cb 1,3-dichloro- 1,1,2,2,3-pentafluoropropane
  • an organic compound having a hydrogen atom bonded thereto is used as a compound used as a proton source.
  • an alcohol such as methanol, ethanol, isopropyl alcohol or sec-butyl alcohol, an alkane such as hexane or heptane, or an aromatic compound such as toluene or xylene, is preferred.
  • a secondary alcohol such as isopropyl alcohol, is particularly preferred.
  • a solvent mixture thereof may also be employed.
  • the light source to be used in the present invention is not particularly limited so long as it is capable of emitting light having a wavelength of shorter than 400 nm.
  • a high pressure mercury lamp, a moderate pressure mercury lamp or a low pressure mercury lamp may preferably be employed.
  • the reaction is conducted usually within a temperature range of from -80 to 100°C, preferably from 0 to 40°C. There is no particular restriction as to the pressure. However, the reaction is conducted usually within a pressure range of from 0 to 10 kg/cm 2 G, preferably from 0 to 2 kg/cm 2 G.
  • the solvent used for the reduction by means of zinc is not particularly limited. However, it is preferred to employ an alcohol such as methanol, ethanol or isopropyl alcohol, an organic acid such as acetic acid or formic acid, an ether such as tetrahydrofuran or water, or a mixture thereof. In particular, an alcohol such as methanol, ethanol or isopropyl alcohol is preferred.
  • Zinc may be used in any form such as a powder, granules or fragments. However, it is most preferred to employ zinc powder. It is unnecessary to apply any special pretreatment such as activating treatment before use.
  • the amount of zinc is not particularly limited. But it is usually preferred to employ it at least stoichiometric amount relative to the starting material.
  • the reaction is conducted usually within a temperature range of from room temperature to 150°C, preferably from 50 to 80°C. There is no particular restriction as to the pressure, but the reaction is conducted usually within a pressure range of from 0 to 10 kg/cm 2 G, preferably from 0 to 3 kg/cm 2 G.
  • the reaction may be carried out either in a liquid phase or a gas phase.
  • the reducing catalyst may be a noble metal catalyst such as platinum, palladium, rhodium or ruthenium, or a base metal catalyst such as nickel. However, it is particularly preferred to use a noble metal catalyst.
  • As the carrier for the reducing catalyst alumina or active carbon is, for example, suitable.
  • the conventional method for preparation of a noble metal catalyst can be applied as a method for supporting the catalyst on the carrier. To use the catalyst, it is preferred to preliminarily apply reduction treatment to the catalyst to obtain the constant performance. However, such a pretreatment is not necessarily required. At least a part of such a metal compound is reduced.
  • the ratio of hydrogen to the starting material may be varied to a large extent.
  • the halogen atom is removed by using hydrogen in a stoichiometrical amount.
  • the molar ratio of the hydrogen to the starting meterial may be larger than one to one, for example, four to one or higher.
  • the reaction temperature is usually from 100 to 350°C, preferably from 100 to 200°C.
  • the contact time is usually from 0.1 to 300 seconds, preferably from 2 to 60 seconds.
  • an alcohol such as ethanol or isopropyl alcohol, acetic acid or pyridine may be used.
  • the reaction can be conducted without any solvent.
  • the reaction temperature for the liquid phase reaction is preferably from room temperature to 150°C, and the reaction pressure - 1 -
  • Lewis acid catalyst > CC ⁇ F 2 CF 2 CHC ⁇ 2
  • the fluorination of l,3,3-trichloro-l,l,2,2- tetrafluoropropane (R224ca) obtained by this reaction is conducted preferably in a gas phase in the presence of a catalyst, or in a liquid phase by using hydrogen fluoride.
  • the proportions of R225ca and R225cb formed by the fluorination vary depending upon the catalyst and reaction conditions empolyed.
  • the catalyst used in the gas phase it is possible to employ a halide or an oxide containing at least one element selected from the group consisting of K£, Cr, Mg, Ca, Ba, Sr, Fe, Ni, Co and Mn.
  • any method may be employed so long as it is a method capable of uniformly dispersing the halide or oxide containing at least one element selected from the above elements.
  • a coprecipitation method or a kneading method may be used.
  • Particularly preferred is a method of coprecipitating hydrates from an aqueous solution of salts of the above mentioned metal elements, or a method of kneading or attriting a cake of hydroxides by a ball mill or a homogenizer.
  • hydroxides those precipitated from an aqueous solution of inorganic salts such as nitrates or sulfates by means of aqueous ammonia or urea, or those prepared by the hydrolysis of organic salts, may be employed.
  • the catalyst in the form of hydrates is preferably dried at a temperature of from 120 to 150°C, followed by calcining usually at a temperature of from 300 to 600°C, preferably from 350 to 450°C.
  • the activation can be conducted in the fluorination reaction system, or by heating with a fluorinated hydrocarbon.
  • the reaction is conducted usually in a gas phase under atmospheric pressure or an elevated pressure within a temperature range of from 150 to 550°C, preferably from 250 to 450°C.
  • the ratio of hydrogen fluoride to the starting material may be varied to a large extent.
  • the chlorine atom is substituted usually by using a stoichiometrical amount of hydrogen fluoride. However, it is possible to use hydrogen fluoride in a larger amount, for example, four molar excess or higher than the stoichiometrical amount of the total molar amount of the starting material.
  • the contact time is usually from 0.1 to 300 seconds, preferably from 5 to 30 seconds.
  • a fluorination catalyst consisting of a halide of e.g. Sb, Nb, Ta or Sn, such as SbF 5 , SbC ⁇ 5 , SbC ⁇ 2 F 3 , NbC ⁇ 5 , NbF 5 , SbC ⁇ 5 , NbC ⁇ 5 , NbF 5 , TaF 5 , aC ⁇ 5 or SnC- 4 .
  • the fluorination reaction is conducted in a liquid phase under atmospheric pressure or an elevated pressure usually within a temperature range of from 0 to 200°C, preferably from room temperature to 150°C. In the present invention, the reaction is usually conducted in the absence of any solvent. However, a solvent may be employed.
  • the solvent employed in such a case is not particularly limited so long as it is capable of dissolving propanes as the starting materials, and the solvent itself is hardly fluorinated as compared with the starting material.
  • the reaction pressure is usually from 0 to 10 kg/cm 2 G, and when a solvent is used, the reaction pressure depends upon the type of the solvent.
  • Hydrogen fluoride may be charged before the reaction. However, it is more effective to feed it into the liquid phase as the reaction proceeds. As another embodiment, when carbon tetrachloride
  • R214cb obtained by the addition reaction of 4F with RIO may firstly be fluorinated in the same manner as the fluorination of R224ca, to form trichloropentafluoropropane such as R215ca or R215cb, which is then reduced in the same manner to obtain dichloropentafluoropropane such as R225cb or R225ca.
  • This powder was molded into cylinders having a diameter of 5 mm and a height of 5 mm by means of a tabletting machine.
  • the catalyst thus obtained was fluorinated in a stream of a gas mixture of hydrogen fluoride/nitrogen at a temperature of from 200 to 400°C for activation prior to the reaction.
  • Example 3
  • Example 4 Into a 10 £ Hastelloy C autoclave, 0.5 kg (3.7 mols) of anhydrous aluminum chloride was added, and the autoclave was deaerated under reduce pressure. Then, 9 kg (75.3 mol) of R20 (CHC ⁇ 3 ) was added thereto. The autoclave was heated to 65°C, and tetrafluoroethylene was continuously added while maintaining the reaction temperature at a level of from 65 to 80°C. After adding 4 kg (40 mol) of tetrafluoroethylene, stirring was continued for further one hour.
  • the reaction solution was filtered, and the reaction crude solution was purified by distillation to obtain 7.5 kg of R224ca (1,3,3-trichloro-l,1,2,2-tetrafluoropropane) (yield: 85%). Then, using an Inconel 600 U-shaped reactor with an inner diameter of 2.54 cm and a length of 100 cm as a reactor for fluorination, 200 m£ of a fluorination catalyst prepared as described in Preparation Example 2, was packed. The reactor was heated to 320°C, and 160 m ⁇ /min of gasified R224ca and 440 m ⁇ /min of hydrogen fluoride were supplied, and the reaction was conducted. The reaction crude gas was passed through an aqueous alkaline solution, and 6.9 kg of the reaction mixture was recovered and analyzed by gas chromatography and 19 F-NMR. The results are shown in Table 4. Table 4
  • the reaction mixture was purified by distillation to obtain 4.1 kg of R224ca (l,3,3-trichloro-l,l,3-trichloro- 1,1,2,2-tetrafluoropropane) (yield: 73%). Then, using an Inconel 600 U-shaped reactor with an inner diameter of 2.54 cm and a length of 100 cm as a reactor for fluorination, 200 m£ of a fluorination catalyst prepared as described in Preparation Example 1, was packed. The reactor was heated to 280°C, and 160 m ⁇ /min of gasified R224ca and 440 m ⁇ /min of hydrogen fluoride were supplied thereto, and the reaction was conducted. The reaction crude gas was passed through an aqueous alkaline solution, and 3.7 kg of the reaction mixture was recovered and analyzed by gas chromatography and 19 F-NMR. The results are shown in Table 6.
  • Example 6 Into a 10 £ Hastelloy C autoclave, 0.5 kg (3.7 mols) of anhydrous aluminum chloride was added and the autoclave was deaerated under reduced pressure. Then, 9 kg (58.5 mols) of RIO (CC* 4 ) was added thereto. The autoclave was heated to 65°C, and then tetrafluoroethylene was continuously added while maintaining the reaction temperature at a level of from 65 to 80°C. After adding 3 kg (30 mols) of tetrafluoroethylene, stirring was continued for further one hour.
  • the reaction mixture was purified by distillation to obtain 4.1 kg of R224ca (l,3,3-trichloro-l,l,2,2- tetrafluoropropane) (yield: 73%). Then, using an Inconel 600 U-shaped reactor with an inner diameter of 2.54 cm and a length of 100 cm as a reactor for fluorination, 200 m£ of a fluorination catalyst prepared as described in Preparation Example 2, was packed thereto. The reactor was heated to 320°C, and 160 m ⁇ /min of gasified R224ca and 440 m ⁇ /min of hydrogen fluoride were supplied thereto, and the reaction was conducted. The reaction crude gas was passed through an aqueous alkaline solution, and 3.8 kg of the reaction mixture was recovered and analyzed by gas chromatography and 19 F-NMR. The results are shown in Table 8. Table 8
  • the reaction mixture was purified by distillaiton to obtain 190 g of R224ca (l,3,3-trichloro-l,l,2,2- tetrafluoropropane) . Then, using an Inconel 600 U-shaped reactor with an inner diameter of 2.5 cm and a length of 100 cm as a reactor for fluorination, 200 m£ of a fluorination catalyst prepared as described in Preparation Example 1, was packed. The reactor was heated to 280°C, and 160 m ⁇ /min of R224ca and 440 m ⁇ /min of hydrogen fluoride were supplied thereto, and the reaction was conducted.
  • Example 8 Into a 10 £ Hastelloy C autoclave, 0.5 kg (3.7 mols) of anhydrous aluminum chloride was added and the autoclave was deaerated under reduced pressure. Then, 9 kg (58.5 mols) of RIO (CC ⁇ 4 ) was added thereto. The autoclave was heated to 65°C, and then tetrafluoroethylene was continuously added while maintaining the reaction temperature at a level of from 65 to 80°C. After adding 3 kg (30 mols) of tetrafluoroethylene, stirring was continued for further one hour.
  • the reaction mixture was purified by distillaiton to obtain 240 g of R224ca (l,3,3-trichloro-l,l,2,2- tetrafluoropropane) (yield: 70%). Then, using an Inconel 600 U-shaped reactor with an inner diameter of 2.54 cm and a length of 100 cm as a reactor for fluorination, 200 £ of a fluorination catalyst prepared as described in Preparation Example 1 was packed thereto. The reactor was heated to 280°C, and 160 m ⁇ / in of gasified R224ca and 440 m- ⁇ /min of hydrogen fluoride were supplied thereto, and the reaction was conducted. The reaction was stopped when 3 kg of R224ca was supplied. The reaction crude gas was passed through an aqueous alkaline solution, and 2.7 kg of the reactoin mixture was recovered and analyzed by gas chromatography and 19 F-NMR. The results are shown in Table 12. Table 12
  • reaction mixture was filtered, and the reaction crude solution was purified by distillation to obtain 6.5 kg of R214cb (1,1,1,3- tetrachlorotetrafluoropropane) (yield: 86%).
  • R214cb (1,1,1,3- tetrachlorotetrafluoropropane)
  • Yield 86%).
  • 200 of a fluorination catalyst prepared as described in Preparation Example 1 was packed.
  • the reactor was heated to 280°C, and 240 m ⁇ /min of gasified R214cb and 360 m ⁇ /min of hydrogen fluoride were supplied thereto, and the reaction was conducted.
  • Preparation Example 2 was packed. The reactor was heated to 320°C, and 240 m ⁇ /min of gasified R214cb and 360 m ⁇ /min of hydrogen fluoride were supplied, and the reaction was conducted. The reaction crude gas was passed through an aqueous alkaline solution, and 5.2 kg of the reaction mixture was recovered and purified by distillation to obtain 4.9 kg of R215ca (1,1,3- trichloropentafluoropropane) (yield: 80%).
  • reaction mixture was filtered, and the products were purified by distillation to obtain 6.5 - 32 - kg of R214cb ( 1,1,1,3-tetrachlorotetrafluoropropane) ( yield: 85 % ).
  • R214cb 1,1,1,3-tetrachlorotetrafluoropropane
  • Preparation Example 1 was packed. The reactor was heated to 280° C , and 240 m ⁇ /min of gasified R214cb and 360 m ⁇ /min of hydrogen fluoride were supplied, and the reaction was conducted. The reaction crude gas was passed through an aqueous alkaline solution, and 6.0 kg of the reaction mixture was recovered. The products were purified by distillation to obtain 5.1 kg of R215ca ( 1,1,3-trichloropentafluoropropane) (yield: 83%). Then, into a photochemical reactor (EHB-W1F-500 Model, manufactured by Eiko Co., Ltd.), 800 m£ of isopropanol and 400 g of R215ca were charged. While cooling the reaction solution to 10°C, irradiation by a high pressure mercury lamp was conducted for 10 hours. After washing with water, the organic layer was recovered and analyzed by gas chromatography and 19 F-NMR. The results are shown in Table 15.
  • reaction mixture was purified by distillation to obtain 210 g of R225cb (3,3-dichloro-l,l,2,2,3- pentafluoropropane) (yield: 62%).
  • the ratio of R215cb to R215ca formed was 87:13. Then, into an Inconel 600 U- shaped reactor with an inner diameter of 2.54 cm and a length of 100 cm, 100 £ of a platinum catalyst supported on active carbon (supported rate: 0.5%) was packed to obtain a reactor for reduction, and the reactor was maintained at a temperature of 150°C. To this reactor, a mixture of gasified R215cb and R215ca was supplied at a rate of 96 m ⁇ /min and hydrogen gas was supplied at a rate of 144 m ⁇ /min, and the reaction was conducted. After removing an acid content, 5.7 kg of the products were recovered in a trap cooled to -78°C, and analyzed by gas chromatography and 19 F-NMR. The results are shown in

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

Le procédé de production d'un dichloropentafluoropropane consiste à soumettre CF2=CF2 et CCl3X (où X représente Cl, F ou H) à une réaction d'addition, et à réduire et/ou à fluorurer le C3Cl3F4X résultant afin d'obtenir C3Cl2F5H.
EP90910909A 1989-07-21 1990-07-18 Procede de production d'un dichloropentafluoropropane Withdrawn EP0436031A1 (fr)

Applications Claiming Priority (10)

Application Number Priority Date Filing Date Title
JP187523/89 1989-07-21
JP1187523A JP2738042B2 (ja) 1989-07-21 1989-07-21 ３，３―ジクロロ‐１，１，１，２，２，‐ペンタフルオロプロパンの製造方法
JP217554/89 1989-08-25
JP21755389A JP2734669B2 (ja) 1989-08-25 1989-08-25 ジクロロペンタフルオロプロパンの製法
JP21755489A JP2734670B2 (ja) 1989-08-25 1989-08-25 １，３―ジクロロ―１，１，２，２，３―ペンタフルオロプロパンの製造方法
JP217553/89 1989-08-25
JP21755589A JP2734671B2 (ja) 1989-08-25 1989-08-25 ジクロロペンタフルオロプロパンの製造方法
JP217555/89 1989-08-25
JP26309889A JP2849129B2 (ja) 1989-10-11 1989-10-11 １，３−ジクロロ−１，１，２，２，３−ペンタフルオロプロパンの製造法
JP263098/89 1989-10-11

Publications (1)

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EP0436031A1 true EP0436031A1 (fr) 1991-07-10

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Application Number Title Priority Date Filing Date
EP90910909A Withdrawn EP0436031A1 (fr) 1989-07-21 1990-07-18 Procede de production d'un dichloropentafluoropropane

Country Status (4)

Country Link
EP (1) EP0436031A1 (fr)
KR (1) KR920701092A (fr)
CA (1) CA2034479A1 (fr)
WO (1) WO1991001287A1 (fr)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2624595B2 (ja) * 1990-11-27 1997-06-25 エイ・ジー・テクノロジー株式会社 ジクロロペンタフルオロプロパンの製造法
US5177273A (en) * 1991-02-01 1993-01-05 E. I. Du Pont De Nemours And Company Process for the manufacture of halogen-substituted propanes containing hydrogen and at least five fluorine substituents
US6534467B2 (en) 2001-01-24 2003-03-18 Honeywell International Inc. Azeotrope-like composition of 1,2,2-trichloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride
US20050096246A1 (en) 2003-11-04 2005-05-05 Johnson Robert C. Solvent compositions containing chlorofluoroolefins
WO2008030438A2 (fr) * 2006-09-05 2008-03-13 E. I. Du Pont De Nemours And Company Procédés et méthodes de purification pour la fabrication de fluorocarbures
EP2091899A2 (fr) * 2006-10-31 2009-08-26 E.I. Du Pont De Nemours And Company Procédé de production de 2,3,3,3-tétrafluoropropène, procédé de production de 1-chloro-2,2,3,3,3-pentafluoropropane et compositions azéotropiques de 1-chloro-2,3,3,3-tétrafluoropropène et de hf
TW200837036A (en) 2006-11-15 2008-09-16 Du Pont Process for producing 2,3,3,3-tetrafluoropropene
WO2010001768A1 (fr) * 2008-07-01 2010-01-07 Daikin Industries, Ltd. Procédé de production de composés de propène contenant du fluor
CN108698958B (zh) 2016-02-26 2021-07-16 Ａｇｃ株式会社 纯化1-氯-2,3,3,3-四氟丙烯和纯化1-氯-2,3,3,3-四氟丙烯(z)的制造方法
CN109563010B (zh) * 2016-08-09 2021-05-28 Ａｇｃ株式会社 1-氯-2,3,3,3-四氟丙烯的制造方法
JP2019156732A (ja) * 2018-03-08 2019-09-19 ダイキン工業株式会社 ＨＣＦＣ−２２４ｃａ及び／又はＣＦＯ−１２１３ｙａの精製方法、ＨＣＦＣ−２２４ｃａの製造方法、並びにＣＦＯ−１２１３ｙａの製造方法

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Publication number Priority date Publication date Assignee Title
BE638397A (fr) * 1962-10-09

Non-Patent Citations (1)

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See references of WO9101287A1 *

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WO1991001287A1 (fr) 1991-02-07
CA2034479A1 (fr) 1991-01-22
KR920701092A (ko) 1992-08-11

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