US20100185028A1 - Method for producing 1, 1-dichloro-2,2,3,3,3-pentafluoropropane - Google Patents

Method for producing 1, 1-dichloro-2,2,3,3,3-pentafluoropropane Download PDF

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US20100185028A1
US20100185028A1 US12/689,617 US68961710A US2010185028A1 US 20100185028 A1 US20100185028 A1 US 20100185028A1 US 68961710 A US68961710 A US 68961710A US 2010185028 A1 US2010185028 A1 US 2010185028A1
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hcfc
dichloro
pentafluoropropane
reaction
starting material
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Hidekazu Okamoto
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AGC Inc
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Asahi Glass Co Ltd
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Assigned to ASAHI GLASS COMPANY, LIMITED reassignment ASAHI GLASS COMPANY, LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: OKAMOTO, HIDEKAZU
Publication of US20100185028A1 publication Critical patent/US20100185028A1/en
Priority to US13/052,629 priority Critical patent/US8293953B2/en
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Assigned to AGC Inc. reassignment AGC Inc. CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: ASAHI GLASS COMPANY, LIMITED
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C21/00—Acyclic unsaturated compounds containing halogen atoms
    • C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
    • C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/23—Preparation of halogenated hydrocarbons by dehalogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00—Preparation of halogenated hydrocarbons
    • C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
    • C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation

Definitions

  • the present invention relates to a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225).
  • HCFC-225 dichloropentafluoropropane represented by a chemical formula C 3 HCl 2 F 5
  • a method has been proposed which comprises contacting dichlorofluoromethane with tetrafluoroethylene in the presence of a modified aluminum chloride catalyst to obtain dichloropentafluoropropane, and a technique to apply isomerization to a mixture of various isomers of dichloropentafluoropropane obtained by this method, is disclosed (Patent Document 1).
  • Patent Document 1 U.S. Pat. No. 5,157,171.
  • HCFC-225ca 1,1-dichloro-2,2,3,3,3-pentafluoropropane
  • the present invention is to accomplish the above object and provides the following.
  • HCFC-225ca 1,1-dichloro-2,2,3,3,3-pentafluoropropane
  • R1234yf 2,3,3,3-tetrafluoropropene
  • FIG. 1 shows the change with time of the gas composition at the outlet of the reactor in Example 5 of the present invention.
  • the method according to an embodiment of the present invention is characterized in that one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225), which has a 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) content of less than 60 mol %, particularly less than 50 mol %, is used as a starting material, and this starting material is subjected to an isomerization reaction in the presence of a catalyst so as to increase the HCFC-225ca content in the reaction product to be higher than the content in the starting material.
  • the HCFC-225ca content in the above mixture may be 0 mol %.
  • the isomerization reaction can be carried out in a liquid phase using a Lewis acid as a catalyst. Otherwise, the isomerization reaction can be carried out in a gas phase using a metal oxide as a catalyst.
  • HCFC-225 one isomer or a mixture of at least two isomers which has a HCFC-225ca content of less than 60 mol %.
  • HCFC-225cb 1,3-dichloro-1,2,2,3,3-pentafluoropropane
  • a mixture of isomers of HCFC-225 which contains HCFC-225ca is contacted with an aqueous alkali solution in the presence of a phase transfer catalyst to carry out a reaction for selective dehydrofluorination of HCFC-225ca.
  • the mixture of isomers as the starting material for this reaction contains HCFC-225cb, 2,2-dichloro-1,1,3,3,3-pentafluoropropane (HCFC-225aa), etc. in addition to HCFC-225ca. And such HCFC-225cb, HCFC-225aa, etc. will remain as they are without being reacted (dehydrofluorination). A mixture of isomers such as remaining HCFC-225cb, HCFC-225aa, etc. will be easily separated from the formed R1214ya by distillation.
  • Such a separated mixture of isomers such as HCFC-225cb, HCFC-225aa, etc., can be used as a starting material for the isomerization reaction of the present invention.
  • a HCFC-225 product which is industrially produced, can be used.
  • HCFC-225ca in the HCFC-225 product selectively undergoes a dehydrofluorination reaction to form R1214ya.
  • a mixture of HCFC-225 isomers remained as unreacted, can be used as a starting material containing HCFC-225cb as the main component.
  • HCFC-225ca when such a starting material containing HCFC-225cb as the main component is isomerized, a mixture containing HCFC-225ca and HCFC-225aa as the main components will be formed.
  • HCFC-225ca selectively undergoes the dehydrofluorination reaction to form R1214ya.
  • a mixture of HCFC-225 isomers remained as unreacted can be used as a starting material containing HCFC-225aa as the main component.
  • the catalyst to be used for the isomerization reaction in a liquid phase is not particularly limited so long as it is a Lewis acid, but a halide containing at least one element selected from the group consisting of Al, Sb, Nb, Ta, W, Re, B, Sn, Ga, In, Zr, Hf and Ti, is preferably used.
  • a chloride such as GaCl 2 , GaCl 3 , ZrCl 4 , BCl 3 , AlCl 3 , HfCl 4 , InCl 3 or TiCl 4 , or one having such a compound partially fluorinated, or a bromide or iodide such as GaBr 3 , Gal a , HfBr 4 , InI 3 or TiBr 4 , or one having such a compound partially chlorinated or fluorinated, such as TiCl 2 F 2 , TiClF 3 or ZrCl 2 F 2 .
  • a chloride such as GaCl 2 , GaCl 3 , ZrCl 4 , BCl 3 , AlCl 3 , HfCl 4 , InCl 3 or TiCl 4 , or one having such a compound partially fluorinated, or a bromide or iodide such as GaBr 3 , Gal a , HfBr 4 , InI
  • the amount of such a Lewis acid catalyst is preferably within a range of from 1 to 100 mol %, more preferably from 5 to 50 mol %, to the total amount of isomers of dichloropentafluoropropane (one isomer or a mixture of at least two isomers) as the starting material.
  • a solvent for the reaction may be added.
  • the reaction temperature is preferably within a range of from 0 to 150° C., more preferably from 30 to 100° C.
  • the reaction time is usually from 0.5 to 200 hours, preferably from 1 to 100 hours, although it depends also on the reaction temperature or the type of the Lewis acid catalyst.
  • the catalyst to be used for the isomerization reaction in a gas phase is not particularly limited so long as it is a metal oxide, but an oxide of at least one element selected from the group consisting of Al, Sb, Nb, Ta, W, Re, B, Sn, Ga, In, Zr, Hf and Ti, is preferred, and alumina or zirconia is more preferred.
  • the reaction temperature is preferably from 50 to 500° C., more preferably from 100 to 450° C., further preferably from 200 to 400° C.
  • the reaction pressure is preferably within a range of from 0 to 0.2 kg/cm 2 , particularly preferably within a range of from 0 to 1 kg/cm 2 .
  • the reaction time is usually from 10 to 180 seconds, particularly preferably from 20 to 90 seconds, although it depends also on the reaction temperature or the type of the metal oxide catalyst.
  • the mixture of isomers of HCFC-225 as the starting material may be diluted with an inert gas such as nitrogen and then supplied for the reaction.
  • the molar ratio of the mixture of isomers of HCFC-225 to the inert gas is preferably from 1:0.1 to 1:10, more preferably from 1:0.1 to 1:5.
  • the starting material comprising isomers of HCFC-225 (one isomer or a mixture of at least two isomers) is subjected to an isomerization reaction in the presence of the above-mentioned Lewis acid catalyst or metal oxide catalyst under the above-mentioned reaction conditions, whereby it is possible to form HCFC-225ca and it is possible to substantially increase the HCFC-225ca content in the reaction product over the content in the starting material.
  • the HCFC-225ca content is increased to be higher by at least 10 mol %, more preferably by 30 mol %, than the content in the starting material.
  • this HCFC-225cb undergoes an isomerization reaction to form a mixture of isomers containing HCFC-225ca as the main component, whereby the HCFC-225cb content (molar ratio) in the starting material decreases, and instead, the HCFC-225ca content increases as compared with the content in the starting material.
  • the starting material contains HCFC-225aa
  • the content of HCFC-225aa present in the starting material is larger than the equilibrium composition at the isomerization reaction temperature
  • the HCFC-225aa content in the starting material decreases, and instead, the HCFC-225ca content increases.
  • the HCFC-225 ca content in the starting material must be less than 60 mol % for the following reason.
  • the HCFC-225ca content in an equilibrium state will be from 78 to 80 mol %. If the reaction temperature becomes high, the value of this content will decrease, but it will not be less than 60 mol %.
  • the HCFC-225ca content in the starting material is 60% or higher (for example 70 mol %), it is likely that by the isomerization reaction, the HCFC-225ca content becomes lower than the content in the starting material, but when the HCFC-225ca content is less than 60 mol %, the HCFC-225ca content in the product of the isomerization reaction will increase as compared with the content in the starting material. That is, it is possible to let HCFC-225ca form by the isomerization reaction of the starting material thereby to increase the content to be higher than in the starting material.
  • HCFC-225ca at a high content ratio among various isomers of HCFC-225.
  • HCFC-225ca thus obtained can be used as a starting material to form R1214ya.
  • R1214ya by using HCFC-225ca as a starting material, it is possible to employ, for example, a method which comprises contacting the starting material with an aqueous alkali solution in the presence of a phase transfer catalyst so that only the HCFC-225ca be selectively dehydrofluorinated.
  • the aqueous alkali solution is not particularly limited so long as it is an aqueous solution of a basic compound capable of carrying out the dehydrofluorination reaction.
  • the alkali concentration in the aqueous alkali solution is not particularly limited, but it is preferably from 0.5 to 40 mass %.
  • the amount of the aqueous alkali solution is not particularly limited, but it is preferably adjusted so that the amount of an alkali will be from 0.5 to 1.5 mol equivalent, more preferably from 0.8 to 1.2 mol equivalent, to the amount of HCFC-225ca to be used for the reaction.
  • phase transfer catalyst a phase transfer catalyst which is commonly employed, can be used without any particular restriction. Specifically, it is possible to use, for example, a quaternary ammonium salt or quaternary phosphonium salt substituted by a hydrocarbon group, or a crown ether.
  • the amount of the phase transfer catalyst is preferably from 0.001 to 5 mass %, more preferably from 0.01 to 1 mass %, to the mass of HCFC-225ca as the starting material.
  • reaction temperature in the above dehydrofluorination reaction is not particularly limited, but it is preferably from 0 to 80° C., more preferably from 0 to 50° C.
  • R1214ya thus obtained, is further reacted with hydrogen in the presence of a catalyst (e.g. a Pd catalyst) to obtain 2,3,3,3-tetrafluoropropene (R1234yf) as a cooling medium to be substituted for a greenhouse gas.
  • a catalyst e.g. a Pd catalyst
  • the above catalyst may, for example, be a catalyst having palladium supported on a carrier, or a catalyst containing palladium as the main component and having, supported on a carrier, a mixture prepared by adding palladium and at least one member selected from Group 10 elements other than palladium, Group 8 elements, Group 9 elements and gold.
  • the Group 10 elements other than palladium, Group 8 elements and Group 9 elements include, iron, cobalt, nickel, ruthenium, rhodium, iridium, osmium and platinum.
  • the amount of metals other than palladium to be added to palladium is preferably from 0.01 to 50 parts by mass per 100 parts by mass of palladium.
  • a composite catalyst having other metals added to palladium has an effect such that the catalyst durability tends to be higher than one made of palladium alone.
  • activated carbon or a metal oxide such as alumina, zirconia or silica may, for example, be used.
  • activated carbon is preferably employed from the viewpoint of the activity, durability or selectivity in the reaction.
  • the activated carbon it is possible to use one prepared from a material such as wood, charcoal, fruit shell, coconut shell, peat, lignite or coal, and one obtained from a plant material is preferred to one obtained from a mineral material.
  • a coconut shell activated carbon is particularly preferred.
  • a molded carbon having a length of from about 2 to 5 mm granulated carbon of from about 4 to 50 mesh or pelletized carbon, but granulated carbon of from 4 to 20 mesh or molded carbon is preferred.
  • the reaction to form R1234yf is preferably carried out by a gas phase reduction method wherein heated gasified R1214ya and hydrogen are passed through a reactor packed with a catalyst at a temperature of from 130 to 250° C., preferably from 150 to 200° C. to contact them with the catalyst.
  • the molar ratio of R1214ya to hydrogen supplied (R1214ya:H 2 ) is preferably from 1:0.5 to 1:10, more preferably from 1:0.5 to 1:5.
  • the reaction pressure is usually atmospheric pressure or natural pressure, whereby R1234yf-forming reaction sufficiently proceeds.
  • the contact time with the catalyst may be set within a range of usually from 4 to 60 seconds, preferably from 8 to 40 seconds.
  • the reaction may be carried out by diluting the atmosphere with an inert gas such as nitrogen.
  • the molar ratio of hydrogen and the inert gas to be supplied (H 2 : the inert gas) is preferably from 1:0.1 to 1:10, more preferably from 1:0.5 to 1:4.
  • a Lewis acid catalyst was prepared as follows. That is, a Dimroth condenser having a cooling medium cooled to ⁇ 20° C., circulated, was set on a three-necked flask (internal capacity: 500 mL), 50 g (0.375 mol) of aluminum trichloride (AlCl 3 ) was charged thereto and cooled to 0° C., and then, 175 mL (262.5 g; 1.9 mol) of trichlorofluoromethane (CFCl 3 ) was slowly dropwise added with stirring.
  • AlCl 3 aluminum trichloride
  • CFCl 3 trichlorofluoromethane
  • this starting material liquid was a residue (the residual product) obtained by reacting ASAHIKLIN AK225 (tradename of Asahi Glass Company, Limited; comprising HCFC-225ca, HCFC-225cb and other isomers) being a mixture of isomers of HCFC-225 in an aqueous alkali solution in the presence of a phase transfer catalyst (tetrabutylammonium bromide) to selectively dehydrogen fluorinating HCFC-225ca, subjecting the obtained crude liquid to liquid separation, then distilling the organic phase and recovering R1214ya (boiling point: 45° C.).
  • ASAHIKLIN AK225 tradename of Asahi Glass Company, Limited; comprising HCFC-225ca, HCFC-225cb and other isomers
  • a phase transfer catalyst tetrabutylammonium bromide
  • HCFC-225aa represents 2,2-dichloro-1,1,3,3,3-pentafluoropropane.
  • a catalyst was prepared as follows. That is, a catalyst of spherical activated alumina having a particle size of 2 mm (specific surface area: 280 m 2 /g, “ACBM-1”, manufactured by Catalysts & Chemicals Industries Co., Ltd.) was packed in a reaction tube made of Inconel (registered trademark) 600 and having an inner diameter of 2.54 cm and a length of 100 cm and immersed in a salt bath. A gas mixture of nitrogen/Freon R-12 (CCl 2 F 2 ) of 2/1 (mol/mol) heated to 250° C. was passed for a contact time of 20 seconds for 4 hours to activate the catalyst.
  • CCl 2 F 2 nitrogen/Freon R-12
  • FIG. 1 shows the results obtained by analyzing the change with time of the gas composition at the outlet of the reactor.
  • 1,1-dichloro-2,3,3,3-tetrafluoropropene (CF 3 CF ⁇ CCl 2 , R1214ya) was produced by the following method.
  • a catalyst of activated carbon having 2 mass % of palladium supported (tradename: Shirasagi C2X, manufactured by Takeda Pharmaceutical Company Limited) was packed into a reaction tube made of Inconel (registered trademark) 600 having an inner diameter of 2.54 cm and a length of 100 cm, and immersed in a salt bath.
  • a reduction reaction was carried out under the reaction conditions identified in Table 4 to produce 2,3,3,3-tetrafluoropropene (CF 3 CF ⁇ CH 2 , R1234yf).
  • Example 5 As the residue in the distillation to recover R1214ya in Example 6, a composition shown in Table 5 was recovered. Using this composition as a starting material, an isomerization reaction was carried out by the same method as the method shown in Example 3. The gas composition at the outlet of the reactor was analyzed by gas chromatography thereby to carry out the analysis of the composition of the reaction products. The results are shown in Table 5.
  • composition Composition of starting of reaction material liquid crude gas HCFC-225ca 0 62 HCFC-225cb 5 1 HCFC-225aa 76 35 Other isomers of 19 2 HCFC-225

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
US12/689,617 2009-01-19 2010-01-19 Method for producing 1, 1-dichloro-2,2,3,3,3-pentafluoropropane Abandoned US20100185028A1 (en)

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8357828B2 (en) 2008-12-25 2013-01-22 Asahi Glass Company, Limited Processes for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene
US8609908B2 (en) 2010-06-23 2013-12-17 Asahi Glass Company, Limited Process for producing 1, 1-dichloro-2, 2, 3, 3, 3-pentafluoropropane
WO2015160532A1 (fr) * 2014-04-16 2015-10-22 The Chemours Company Fc, Llc Conversion de chlorofluororopanes et de chlorofluropropènes en fluoropropanes et fluororopènes plus recherchés
US10513479B2 (en) 2015-06-02 2019-12-24 Central Glass Company, Limited Method or producing hydrohalofluoroolefins

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PL2327676T3 (pl) * 2009-11-26 2014-08-29 Sandoz Ag Reakcja związków organicznych z małymi ilościami wodoru
CN102947257B (zh) * 2010-06-23 2014-07-09 旭硝子株式会社 1,1-二氯-2,3,3,3-四氟丙烯及2,3,3,3-四氟丙烯的制造方法
JP6015543B2 (ja) * 2013-04-25 2016-10-26 旭硝子株式会社 （ｅ）−１−クロロ−３，３，３−トリフルオロプロペンの製造方法
WO2016194794A1 (fr) * 2015-06-02 2016-12-08 セントラル硝子株式会社 Procédé de production d'hydrohalofluorooléfines
EP3536681B1 (fr) * 2016-11-01 2020-12-09 Agc Inc. Procédé d'isomérisation d'un composé organique, et procédé de production d'isomère de composé organique
CN113292392B (zh) * 2021-04-16 2022-10-28 台州益普高分子材料有限公司 一种饱和氢氯氟碳化物间的重排反应及其制备含氟醇的方法

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JPH08169850A (ja) * 1994-12-16 1996-07-02 Daikin Ind Ltd １，１，１，２，３，３−ヘキサフルオロプロパンの製造方法
JP3778298B2 (ja) * 1995-01-13 2006-05-24 ダイキン工業株式会社 ヘキサフルオロプロペンの製造方法
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JP4893500B2 (ja) 2007-06-26 2012-03-07 株式会社デンソー 運転支援システム
CN106117008B (zh) 2008-12-25 2019-06-04 Ａｇｃ株式会社 1,1-二氯-2,3,3,3-四氟丙烯和2,3,3,3-四氟丙烯的制造方法

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8357828B2 (en) 2008-12-25 2013-01-22 Asahi Glass Company, Limited Processes for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene
US8609908B2 (en) 2010-06-23 2013-12-17 Asahi Glass Company, Limited Process for producing 1, 1-dichloro-2, 2, 3, 3, 3-pentafluoropropane
WO2015160532A1 (fr) * 2014-04-16 2015-10-22 The Chemours Company Fc, Llc Conversion de chlorofluororopanes et de chlorofluropropènes en fluoropropanes et fluororopènes plus recherchés
US9822047B2 (en) 2014-04-16 2017-11-21 The Chemours Company Fc, Llc Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes
US10351495B2 (en) 2014-04-16 2019-07-16 The Chemours Company Fc, Llc Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes
US10584082B2 (en) 2014-04-16 2020-03-10 The Chemours Company Fc, Llc Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes
US10815173B2 (en) 2014-04-16 2020-10-27 The Chemours Company Fc, Llc Compositions comprising fluoropropenes and fluoropropanes and methods for preparing the compositions
US11332424B2 (en) 2014-04-16 2022-05-17 The Chemours Company Fc, Llc Conversion of chlorofluororopanes and chlorofluropropenes to more desirable fluoropropanes and fluororopenes
US10513479B2 (en) 2015-06-02 2019-12-24 Central Glass Company, Limited Method or producing hydrohalofluoroolefins

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JPWO2010082662A1 (ja) 2012-07-05
JP5598333B2 (ja) 2014-10-01
CN102282115A (zh) 2011-12-14
EP2380866A1 (fr) 2011-10-26
EP2380866B1 (fr) 2017-05-10
EP2380866A4 (fr) 2012-05-23
CN102282115B (zh) 2015-01-07
US8293953B2 (en) 2012-10-23
US20110172469A1 (en) 2011-07-14

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