WO1994017020A1 - Process for producing 1,1,1,4,4,4-hexafluoro-2-butenes and 1,1,1,4,4,4-hexafluorobutane - Google Patents
Process for producing 1,1,1,4,4,4-hexafluoro-2-butenes and 1,1,1,4,4,4-hexafluorobutane Download PDFInfo
- Publication number
- WO1994017020A1 WO1994017020A1 PCT/JP1994/000068 JP9400068W WO9417020A1 WO 1994017020 A1 WO1994017020 A1 WO 1994017020A1 JP 9400068 W JP9400068 W JP 9400068W WO 9417020 A1 WO9417020 A1 WO 9417020A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- butene
- hexafluoro
- catalyst
- reaction
- butenes
- Prior art date
Links
Classifications
-
- 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
- C07C17/013—Preparation of halogenated hydrocarbons by addition of halogens
- C07C17/06—Preparation of halogenated hydrocarbons by addition of halogens combined with replacement of hydrogen atoms by halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/07—Preparation of halogenated hydrocarbons by addition of hydrogen halides
- C07C17/08—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/10—Preparation of halogenated hydrocarbons by replacement by halogens of hydrogen atoms
-
- 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
- C07C17/354—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by hydrogenation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
- C12C11/00—Fermentation processes for beer
- C12C11/02—Pitching yeast
Definitions
- the present invention relates to a method for producing 1,1,1,4,4,4'-xafluorobutane, which is a useful compound used as a foaming, washing, and heating medium as an alternative to HCFC, and as a reaction intermediate thereof 1,1,1,4,4,4- ⁇ xafluoro-2,3-dichloro-1,2-butene, 1,1,1,4,4 1,1,1,1,4,4,4-hexafluoro-1,2-hexafluoro-2-butene and 1,1,1,4,4,4-hexafluoro-a-2-butene
- the present invention relates to a method for producing 2-butenes.
- 1,1,1,4,4,4 ⁇ xafluoro-2,3-dichloro-1-butene can be synthesized by chlorination and fluorination of hexaclobutadiene (US Pat. No. 3,149,170). Also, 1,1,1,4,4, ⁇ xafluoro-2-chloro-2-butene can be obtained by fluorinating hexachloro-1,3-butadiene with HF in the presence of antimony halide. It is known that it is produced (JP-A-64-50830).
- hexaclo ⁇ -butadiene used as a raw material in a known method is expensive, and it is difficult to obtain it in large quantities.
- An object of the present invention is to provide 1,1,1,4,4,4-hexafluoro-2,3-dichroic-2-butene, 1,1,1,4,4,4-hexafluoro- To provide a cheaper industrial method for the production of 2-chloro-2-butene and 1,1,1,4,4,4-hexafluo-2-butene, and to reduce 1,1,1 , 4, 4, 4—Hexafluorobutane to provide an inexpensive industrial method.
- the present inventor has proposed an industrially useful and inexpensive 1,1,1,, 4,4-hexafluoro-2,3-dicone-low 2-butene, 1,1,1,4,4,4-hexene.
- Xafluoro-2-butene 2-butene and 1,1,1,4,4,4- ⁇ ⁇ ⁇ Xafluoro-2-butene has been established, and 1,1,1,4,4
- 1,1,1,4,4 As a result of intensive studies to establish a process for the production of hexafluorobutane, at least one of butane, butene and butadiene, which is inexpensive and readily available, was converted to chlorine and ⁇ F in the presence of a suitable catalyst.
- butane, butene, and butadiene can be used alone or as a mixture as raw materials.
- partially chlorinated or ⁇ - and fluorinated butane, butadiene, and 2-butene, which are intermediates of the reaction can also be separated from the reaction product and used. Chlorinated or ⁇ - and fluorinated butane, butadiene and 2-butene are synthesized by another method and used for the reaction You can also.
- the catalyst used for the reaction may be a metal fluoride (for example, chromium), which is precipitated from a solution of a metal salt with the use of an alkali metal, and is fluorinated using HF. it can. Hydrochloride or nitrate can be used as the metal salt. Ammonia, urea, and metal hydroxides can be used as the alkali.
- a metal fluoride for example, chromium
- metal one or a mixture of two or more selected from aluminum, chromium, manganese, nickel, cobalt, iron and zinc can be used. Further, a metal fluoride obtained by fluorinating the above metal halide and / or a metal oxyfluoride obtained by oxidizing the metal fluoride can also be used.
- metal fluorides can be used alone or supported on a suitable carrier.
- the carrier is not limited as long as it does not affect the catalytic activity.
- activated carbon, aluminum fluoride and the like can be used.
- the reaction temperature can be appropriately selected within the range of 250 to 450, but if the reaction temperature is low, the reaction is slow and not practical. Preferably, it is performed at 300: to 400 t. Although the reaction is exothermic, the reaction temperature can be easily controlled by appropriately choosing the amount of HF and the amount of intermediate to be recycled.
- 1,1,1,4,4,4-hexafluoro-2,3-dichloro-2-butene 1,1,1,4,4,4—
- 1,1,1 is obtained by a reduction reaction under a noble metal catalyst.
- 4,4,4-Hexafluorobutane is preferably synthesized.
- noble metal catalyst used in this reduction reaction it is preferable to use a noble metal supported on a carrier by a commonly used method.
- Noble metals include Pt and Pd.
- the carrier may be one that does not directly participate in the reaction, and examples thereof include alumina and activated carbon.
- the hydrogen used for the hydrogenation is preferably 1 to 10 moles per 1 mole of the above mixture.
- the reaction temperature of the hydrogenation reaction can be selected appropriately from 20 to 300.
- the reaction temperature is low, butane containing chlorine is generated, and when the temperature is increased, deterioration of the reduction catalyst tends to be accelerated.
- chlorine-containing butanes can be separated by ordinary methods such as distillation, so that they can be recycled after separation.
- At least one of butane, butene, and butadiene, which is inexpensive and easily available, is reacted with chlorine and HF in the presence of a suitable catalyst to obtain the target 1,1, 1,4,4,4-hexafluoro-2,3-dichloro-1-butene, 1,1,1,4,4,4-hexafluoro-2-chloro-1,2-butene and 1,1 , 1,4,4,4-hexafluoro-2-butene mixture (1,1,1,4,4,4-hexafluoro-2-butenes) is produced in a high yield in By reducing this product in the presence of a noble metal catalyst, 1,1,1,4,4,4-hexafluorobutane can be obtained with high selectivity.
- Chromium oxide prepared by a general method was pelletized to a diameter of 3 mm 3 mm: After filling the reaction tube with 50 cc of the catalyst, it was fluorinated with HF. After adjusting the temperature of the reaction tube to 3501, 500 cc / min of HF and 200 cc / min of chlorine were introduced by gas. 20ccZmin of n-butane was introduced into this. The product was washed with water and analyzed by GLC.
- Aluminum oxide prepared by a general method was used as a 3 ⁇ X 3 mm bellet. After filling the reaction tube with 50 cc of this catalyst, it was fluorinated with HF. After adjusting the temperature of the reaction tube to 350, 500 cc / min of HF and 200 cc Zmin of chlorine were introduced by gas. 20ccZmin of n-butane was introduced into this. The product was washed with water and subjected to GLC analysis.
- the product selectivity is shown in Table 12 below.
- Manganese oxide prepared by a general method was used as a pellet of 3 ⁇ X 3 mm. After filling the reaction tube with 50 cc of this catalyst, it was fluorinated with HF. After adjusting the temperature of the reaction tube to 350, HF 500 cc / min and chlorine 200 cc Zmin were introduced by gas. To this was introduced n-butane 20 cc / min. The product was washed with water and analyzed by GLC.
- the product selectivity is shown in Table 13 below.
- Nickel oxide prepared by a general method was used as a pellet of 3 ⁇ X 3 mm. After filling the reaction tube with 50 cc of this catalyst, it was fluorinated with HF. After adjusting the temperature of the reaction tube to 350, HF 500 cc / min and chlorine ZOOccZmin were introduced by gas. To this was introduced n-butane 20 cc / min. The product was washed with water and analyzed by GLC.
- Cobalt oxide prepared by a general method was used as a 3 mm ⁇ X 3 mm beret. After filling the reaction tube with 50 cc of this catalyst, it was fluorinated with HF. After adjusting the temperature of the reaction tube to 350, HF 500 cc / min and chlorine 200 cc Zmin were introduced by gas. To this, II-butane was introduced at 20 cc / min. The product was washed with water and analyzed by GLC.
- a reaction tube was charged with 10 g of a catalyst having 1% by weight of Pd supported on charred charcoal and activated with hydrogen.
- the reaction temperature was maintained at 150, and the mixture of the three butenes obtained in Example 1 was introduced into the reactor with lOOccZmin and hydrogen at 300ccZmin.
- the product was analyzed by GLC after washing with water.
- the product selectivity is shown in the table below.
- a reaction tube was charged with 10 g of a catalyst in which 1% by weight of Pt was supported on charcoal activated carbon, and activated with hydrogen.
- the reaction temperature was maintained at 150, and the mixture of the three butenes obtained in Example 1 was introduced at 100 cc / min and hydrogen was introduced at 300 cc / niin.
- the product was washed with water and analyzed by GLC.
- the product selectivity is shown in Table 7 below.
- Chromium oxide prepared by a general method was pelletized at 3 ⁇ X 3 mm.
- C The catalyst was charged into a reaction tube by 50 cc and then fluorinated with HF. After adjusting the temperature of the reaction tube to 350 t, HF 500 cc / min and chlorine 200 cc Zniin were introduced by gas. To this, 2-butene 20ccZmin was introduced. The product was washed with water and analyzed by GLC.
- the product selectivity is shown in Table 19 below.
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- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
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Description
Claims
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69419005T DE69419005T2 (de) | 1993-01-29 | 1994-01-19 | Verfahren zur herstellung von 1,1,1,4,4,4-hexafluoro-2-butenen und 1,1,4,4,4,4-hexafluorobutan |
EP94904740A EP0682001B1 (en) | 1993-01-29 | 1994-01-19 | Process for producing 1,1,1,4,4,4-hexafluoro-2-butenes and 1,1,1,4,4,4-hexafluorobutane |
US08/495,662 US5608128A (en) | 1993-01-29 | 1994-01-19 | Production methods of 1,1,1,4,4,4-hexsfluoro-2-butene compounds and 1,1,1,4,4,4,-hexafluorobutane |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5/34504 | 1993-01-29 | ||
JP03450493A JP3304468B2 (ja) | 1993-01-29 | 1993-01-29 | 1,1,1,4,4,4−ヘキサフルオロ−2−ブテン類及び1,1,1,4,4,4−ヘキサフルオロブタンの製造方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1994017020A1 true WO1994017020A1 (en) | 1994-08-04 |
Family
ID=12416092
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1994/000068 WO1994017020A1 (en) | 1993-01-29 | 1994-01-19 | Process for producing 1,1,1,4,4,4-hexafluoro-2-butenes and 1,1,1,4,4,4-hexafluorobutane |
Country Status (5)
Country | Link |
---|---|
US (1) | US5608128A (ja) |
EP (1) | EP0682001B1 (ja) |
JP (1) | JP3304468B2 (ja) |
DE (1) | DE69419005T2 (ja) |
WO (1) | WO1994017020A1 (ja) |
Families Citing this family (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4421702A1 (de) * | 1994-06-21 | 1996-01-04 | Bayer Ag | Verfahren zur Herstellung von 1,1,1,4,4,4-Hexafluorbutan in flüssiger Phase |
JP3729281B2 (ja) * | 1994-11-24 | 2005-12-21 | 独立行政法人産業技術総合研究所 | 弗素化アルケン誘導体および弗素化アルカン誘導体の製造方法 |
JP4333894B2 (ja) * | 2001-02-13 | 2009-09-16 | 日本ゼオン株式会社 | パーハロゲン化5員環化合物の製造方法 |
US7615668B2 (en) * | 2004-10-18 | 2009-11-10 | Central Glass Co., Ltd. | Method for producing 4,4,4-trifluorobutane-2-one |
EP1814837B1 (en) * | 2004-10-18 | 2010-02-24 | Central Glass Co., Ltd. | A method for producing 4,4,4-trifluorobutane-2-one |
ES2731723T3 (es) * | 2005-11-01 | 2019-11-18 | Chemours Co Fc Llc | Composiciones de disolventes que comprenden hidrocarburos fluorados insaturados |
CA2922197A1 (en) * | 2005-11-01 | 2007-05-10 | E. I. Du Pont De Nemours And Company | Compositions comprising fluoroolefins and uses thereof |
WO2007116999A1 (ja) | 2006-04-12 | 2007-10-18 | Kao Corporation | W/o/w型乳化組成物 |
US20090270522A1 (en) * | 2008-04-25 | 2009-10-29 | Honeywell International Inc. | Blowing agents for polymeric foams |
JP2010037205A (ja) * | 2008-07-31 | 2010-02-18 | Nippon Zeon Co Ltd | フッ素アルカン化合物、その製造方法及びパーフルオロアルキン化合物の製造方法 |
JP5609043B2 (ja) * | 2009-08-26 | 2014-10-22 | 東ソー株式会社 | 微粒径陰イオン交換樹脂及びその製造法、並びにそれを用いたジクロロブテンの製造方法 |
US20110144216A1 (en) * | 2009-12-16 | 2011-06-16 | Honeywell International Inc. | Compositions and uses of cis-1,1,1,4,4,4-hexafluoro-2-butene |
US8461401B2 (en) * | 2010-03-26 | 2013-06-11 | Honeywell International Inc. | Method for making hexafluoro-2-butene |
US8426655B2 (en) * | 2010-03-26 | 2013-04-23 | Honeywell International Inc. | Process for the manufacture of hexafluoro-2-butene |
US8530709B2 (en) * | 2010-05-21 | 2013-09-10 | Honeywell International Inc. | Process for the production of fluorinated alkenes |
US8604257B2 (en) * | 2010-05-21 | 2013-12-10 | Honeywell International Inc. | Process for the preparation of fluorinated cis-alkene |
US8901360B2 (en) | 2010-05-21 | 2014-12-02 | Honeywell International Inc. | Process for cis 1,1,1,4,4,4-hexafluoro-2-butene |
US11390574B2 (en) * | 2017-12-04 | 2022-07-19 | The Chemours Company Fc, Llc | Process for producing 1,1,3-trichloro-4,4,4-trifluorobut-1-ene |
WO2019240119A1 (ja) | 2018-06-12 | 2019-12-19 | 花王株式会社 | W/o型乳化組成物 |
TWI836109B (zh) * | 2019-07-01 | 2024-03-21 | 日商大金工業股份有限公司 | 烷烴的製造方法 |
JP6958596B2 (ja) * | 2019-07-01 | 2021-11-02 | ダイキン工業株式会社 | アルカンの製造方法 |
CN118019723A (zh) * | 2021-09-30 | 2024-05-10 | 株式会社力森诺科 | (e)-1,1,1,4,4,4-六氟-2-丁烯的制造方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JPS5028407B1 (ja) * | 1969-02-27 | 1975-09-16 | ||
JPH01146831A (ja) * | 1987-10-20 | 1989-06-08 | Bayer Ag | フツ素化c↓4〜c↓6炭化水素の製造方法 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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FR1338591A (fr) * | 1961-09-11 | 1963-09-27 | Sicedison Spa | Procédé pour la préparation de composés organiques fluorurés par fluoruration d'hydrocarbures aliphatiques en phase vapeur |
NL136586C (ja) * | 1967-01-11 | |||
US4110406A (en) * | 1976-12-21 | 1978-08-29 | Allied Chemical Corporation | Preparation of 1-chloro-2-trifluoromethyl-3,3,3-trifluoropropene from isobutylene |
US4081487A (en) * | 1976-12-27 | 1978-03-28 | Allied Chemical Corporation | Preparation of 1-chloro-2-trifluoromethyl-3,3,3-trifluoropropene from isobutane |
DE4004494A1 (de) * | 1990-02-14 | 1991-08-22 | Bayer Ag | Verfahren zur herstellung von gesaettigten, fluorhaltigen und chlorfreien kohlenwasserstoffen |
US5364991A (en) * | 1991-11-22 | 1994-11-15 | Daikin Industries, Ltd. | Preparation of 1,1,1,4,4,4-hexafluorobutane |
AU7559194A (en) * | 1993-08-16 | 1995-03-14 | Allied-Signal Inc. | Process for combining chlorine-containing molecules to synthesize fluorine-containing products |
-
1993
- 1993-01-29 JP JP03450493A patent/JP3304468B2/ja not_active Expired - Fee Related
-
1994
- 1994-01-19 DE DE69419005T patent/DE69419005T2/de not_active Expired - Fee Related
- 1994-01-19 EP EP94904740A patent/EP0682001B1/en not_active Expired - Lifetime
- 1994-01-19 US US08/495,662 patent/US5608128A/en not_active Expired - Fee Related
- 1994-01-19 WO PCT/JP1994/000068 patent/WO1994017020A1/ja active IP Right Grant
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5028407B1 (ja) * | 1969-02-27 | 1975-09-16 | ||
JPH01146831A (ja) * | 1987-10-20 | 1989-06-08 | Bayer Ag | フツ素化c↓4〜c↓6炭化水素の製造方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0682001A4 * |
Also Published As
Publication number | Publication date |
---|---|
EP0682001A4 (en) | 1996-04-17 |
JPH06228023A (ja) | 1994-08-16 |
DE69419005T2 (de) | 2000-01-27 |
DE69419005D1 (de) | 1999-07-15 |
EP0682001A1 (en) | 1995-11-15 |
JP3304468B2 (ja) | 2002-07-22 |
US5608128A (en) | 1997-03-04 |
EP0682001B1 (en) | 1999-06-09 |
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