JP4363983B2 - 元素状ハロゲンを用いた触媒−再生 - Google Patents
元素状ハロゲンを用いた触媒−再生 Download PDFInfo
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- JP4363983B2 JP4363983B2 JP2003554333A JP2003554333A JP4363983B2 JP 4363983 B2 JP4363983 B2 JP 4363983B2 JP 2003554333 A JP2003554333 A JP 2003554333A JP 2003554333 A JP2003554333 A JP 2003554333A JP 4363983 B2 JP4363983 B2 JP 4363983B2
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- JP
- Japan
- Prior art keywords
- process according
- aliphatic
- catalyst
- compounds
- fluorinated
- 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.)
- Expired - Fee Related
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Classifications
-
- 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/28—Regeneration or reactivation
- B01J27/32—Regeneration or reactivation of catalysts comprising compounds of halogens
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J38/00—Regeneration or reactivation of catalysts, in general
- B01J38/04—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst
- B01J38/42—Gas or vapour treating; Treating by using liquids vaporisable upon contacting spent catalyst using halogen-containing material
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G30/00—Compounds of antimony
- C01G30/006—Halides
- C01G30/007—Halides of binary type SbX3 or SbX5 with X representing a halogen, or mixed of the type SbX3X'2 with X,X' representing different halogens
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
-
- 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
- C07C17/087—Preparation of halogenated hydrocarbons by addition of hydrogen halides to unsaturated halogenated 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
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/21—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms with simultaneous increase of the number of halogen atoms
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
ジクロロトリフルオロエタン(HCFC−123)の製造
連続可動式オートクレーブ中に、ペンタクロロエタン、五フッ化アンチモン及びHFを導入した。HF対SbF5のモル比は約12:1であり、SbF5対出発材料のモル比は5:1であった。その後、オートクレーブを温度100℃及び圧力15バールにした。反応器内容物の一部(触媒約15モル%)を連続的に反応器(オートクレーブ)から取り出し、ストリップ塔に移した。有機成分(殊にHCFC−121、HCFC−122及びHFC−123、並びにペンタクロロエタン)をHF及びHClと一緒に圧力減少下に分離し、オートクレーブ中に返送した。ストリップ塔の残存する部分流を、触媒再生のために、向流で元素状塩素と混合した。
ペルクロロエチレンの完全反応後の塩素化を用いたジクロロトリフルオロエタンの製造
ペルクロロエチレン[0.05モル]を、テフロン内層(Teflon-Inliner)を備えたオートクレーブ中に装入し、ゆっくりと、五フッ化アンチモン[0.1モル]及びフッ化水素[0.88モル]と混合した。オートクレーブを密閉し、撹拌下に1時間、120℃に予熱した油浴中に配置した。この場合、ペルクロロエチレンは完全に変換された。
Claims (16)
- フッ化水素の使用下で、かつ、元素状ハロゲンを用いた酸化により再生される触媒の存在下で、ハロゲン−フッ素−交換によって、部分的にハロゲン化されたフッ素含有有機化合物を製造する方法において、元素状ハロゲンを、ハロゲンに対して望ましくない反応性の出発化合物又は中間生成物と接触させないように再生を行い、その際、ハロゲン導入の前に、望ましくない反応性有機化合物を最後まで反応させるか、又は反応器から除去するか、あるいは、反応混合物の一部を反応器から排出し、揮発性の有機及び無機化合物をガス状又は蒸気状で排出分から除去し、排出分をハロゲンと混合して触媒を再生し、再生した触媒を含有する排出分を反応器に返送し、その際、五塩化アンチモン及び/又はそのフッ素化生成物ないしHF−付加物の存在で、臭素−フッ素−交換又は塩素−フッ素−交換を行う製造法であることを特徴とする、部分的にハロゲン化されたフッ素含有有機化合物の製造法。
- 付加的なHF−付加を行う、請求項1記載の方法。
- ハロゲンとして塩素を用いて再生を行う、請求項1記載の方法。
- 脂肪族フッ化炭化水素化合物又は脂肪族フッ化塩化炭化水素化合物の製造を行う、請求項1記載の方法。
- 1〜10個の炭素原子を有する脂肪族フッ化炭化水素化合物又は脂肪族フッ化塩化炭化水素化合物の製造を行う、請求項4記載の方法。
- 脂肪族C1〜C5−フッ化炭化水素化合物又は脂肪族C1〜C5−フッ化塩化炭化水素化合物を製造する、請求項5記載の方法。
- 脂肪族C1〜C4−フッ化炭化水素化合物又は脂肪族C1〜C4−フッ化塩化炭化水素化合物を製造する、請求項5記載の方法。
- クロロエテン又はクロロフルオロエテンからフルオロエタン又はクロロフルオロエタンの製造を行う、請求項1記載の方法。
- 反応器中で、1〜15バールの範囲内の圧力が支配する、請求項1記載の方法。
- 反応器中で、20〜200℃の範囲内の温度が支配する、請求項1記載の方法。
- 排出分を最高で5バールの圧力に放圧し、有機及び無機揮発性成分を分離する、請求項1記載の方法。
- 反応混合物の排出分が、二重結合を有する有機化合物を本質的に含まない、請求項1記載の方法。
- フッ化水素対触媒のモル比が1:1〜30:1の範囲内にある、請求項1記載の方法。
- 触媒対有機出発化合物のモル比が0.1:1〜20:1の範囲内にある、請求項1記載の方法。
- 触媒量の5〜20モル%が排出に利用される成分中に存在する、請求項1記載の方法。
- Sb(III)の再生により処理生成物のフッ素化度を制御し、その際、フッ素化度は、Sb(III)の再生が完全であればある程ますます高くなる、請求項1記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10163170A DE10163170A1 (de) | 2001-12-21 | 2001-12-21 | Katalysator-Regenerierung mit elementarem Halogen |
PCT/EP2002/014220 WO2003053580A1 (de) | 2001-12-21 | 2002-12-13 | Katalysator-regenerierung mit elementarem halogen |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005517664A JP2005517664A (ja) | 2005-06-16 |
JP4363983B2 true JP4363983B2 (ja) | 2009-11-11 |
Family
ID=7710308
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003554333A Expired - Fee Related JP4363983B2 (ja) | 2001-12-21 | 2002-12-13 | 元素状ハロゲンを用いた触媒−再生 |
Country Status (7)
Country | Link |
---|---|
US (2) | US7074975B2 (ja) |
EP (1) | EP1497029A1 (ja) |
JP (1) | JP4363983B2 (ja) |
CN (1) | CN1592656B (ja) |
AU (1) | AU2002366737A1 (ja) |
DE (1) | DE10163170A1 (ja) |
WO (1) | WO2003053580A1 (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6479718B1 (en) * | 2002-03-28 | 2002-11-12 | Atofina Chemicals, Inc. | Liquid phase process for HCFC-123 |
US20060036117A1 (en) * | 2004-08-10 | 2006-02-16 | Mitchel Cohn | Catalyst preparation processes, catalyst regeneration processes, halocarbon production processes, and halocarbon production systems |
US8664144B2 (en) * | 2008-12-23 | 2014-03-04 | Chevron Phillips Chemical Company Lp | Methods of reactivating an aromatization catalyst |
CN103313960B (zh) | 2011-01-21 | 2016-06-08 | 阿克马法国公司 | 催化气相氟化 |
US8912108B2 (en) | 2012-03-05 | 2014-12-16 | Chevron Phillips Chemical Company Lp | Methods of regenerating aromatization catalysts |
US8716161B2 (en) | 2012-03-05 | 2014-05-06 | Chevron Phillips Chemical Company | Methods of regenerating aromatization catalysts |
US9387467B2 (en) | 2012-09-26 | 2016-07-12 | Chevron Phillips Chemical Company Lp | Aromatization catalysts with high surface area and pore volume |
WO2016079122A1 (en) | 2014-11-17 | 2016-05-26 | Solvay Sa | A method for producing a chemical compound and apparatus therefor |
JP7123958B2 (ja) | 2019-02-15 | 2022-08-23 | 福建永晶科技股▲ふん▼有限公司 | フルオロアリール化合物及びその誘導体の新しい製造方法 |
JP7071036B2 (ja) | 2019-02-15 | 2022-05-18 | 福建永晶科技股▲ふん▼有限公司 | Friedel-Crafts反応の新しい新方法及び当該方法に用いられる触媒 |
EP3713907A4 (en) | 2019-02-15 | 2020-11-25 | Fujian Yongjing Technology Co., Ltd | NEW PROCESS FOR THE MANUFACTURING OF FLUORINE BENZENE AND FLUORINE BENZOPHENON, AND CORRESPONDING DERIVATIVES |
CN110627612A (zh) * | 2019-09-26 | 2019-12-31 | 江苏三美化工有限公司 | 一种提高反应过程选择性的管道化生产氟化烷烃方法 |
CN110787833A (zh) * | 2019-10-09 | 2020-02-14 | 浙江大学 | 一种液相法管道化连续化生产氟化烷烃过程中对氟化催化剂的再活化方法 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2005705A (en) | 1930-09-20 | 1935-06-18 | Kinetic Chemicals Inc | Preparation of carbon compounds containing fluorine |
US2005710A (en) * | 1931-05-20 | 1935-06-18 | Kinetic Chemicals Inc | Preparation of fluorine compounds |
US2230925A (en) | 1939-03-23 | 1941-02-04 | Kinetic Chemicals Inc | Preparation of 1, 1, 1-trifluoro-2-chloro-ethane |
US2510872A (en) * | 1944-08-03 | 1950-06-06 | Atomic Energy Commission | Method for regenerating antimony pentafluoride from spent antimony halides resulting from the fluorination of organic chlorides |
GB589167A (en) | 1945-03-16 | 1947-06-12 | William Basil Whalley | Improvements in or relating to the production of fluorinated derivatives of aliphatic hydrocarbons |
US2759026A (en) * | 1950-02-01 | 1956-08-14 | Texas Co | Process for fluorination of hydrocarbons |
DE2439540C2 (de) | 1974-08-17 | 1978-06-15 | Kali-Chemie Ag, 3000 Hannover | Verfahren zur Rückgewinnung von Antimonpentachlorid aus zur Fluorierung von chlorierten Kohlenwasserstoffen eingesetzten Katalysatorlösungen |
US4147733A (en) * | 1978-05-22 | 1979-04-03 | The Dow Chemical Company | Fluorination of chlorinated hydrocarbons |
US4438088A (en) | 1982-03-11 | 1984-03-20 | The Dow Chemical Company | Preparation of antimony trifluorodichloride and fluorination of fluorinatable hydrocarbons and halocarbons therewith |
US5105033A (en) * | 1989-05-25 | 1992-04-14 | E. I. Du Pont De Nemours And Company | Process for preparing 1,1-dichloro-1-fluoroethane |
DE3929263A1 (de) | 1989-09-02 | 1991-03-07 | Kali Chemie Ag | Verfahren zur aufarbeitung von antimonhalogenidkatalysatorloesungen |
GB9212925D0 (en) * | 1992-06-18 | 1992-07-29 | Ici Plc | Production of hydrofluorocarbons |
US5714650A (en) * | 1995-06-07 | 1998-02-03 | E. I. Du Pont De Nemours And Company | Continuous manufacture of 1,1-difluoroethane |
US6034016A (en) * | 1998-05-08 | 2000-03-07 | Laroche Industries Inc. | Method for regenerating halogenated Lewis acid catalysts |
-
2001
- 2001-12-21 DE DE10163170A patent/DE10163170A1/de not_active Withdrawn
-
2002
- 2002-12-13 EP EP02805322A patent/EP1497029A1/de not_active Withdrawn
- 2002-12-13 JP JP2003554333A patent/JP4363983B2/ja not_active Expired - Fee Related
- 2002-12-13 CN CN028234685A patent/CN1592656B/zh not_active Expired - Fee Related
- 2002-12-13 WO PCT/EP2002/014220 patent/WO2003053580A1/de active Application Filing
- 2002-12-13 AU AU2002366737A patent/AU2002366737A1/en not_active Abandoned
-
2004
- 2004-06-18 US US10/870,425 patent/US7074975B2/en not_active Expired - Fee Related
-
2005
- 2005-10-27 US US11/259,138 patent/US7319175B2/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
US20050027147A1 (en) | 2005-02-03 |
US20060036118A1 (en) | 2006-02-16 |
DE10163170A1 (de) | 2003-07-03 |
US7074975B2 (en) | 2006-07-11 |
CN1592656A (zh) | 2005-03-09 |
JP2005517664A (ja) | 2005-06-16 |
AU2002366737A1 (en) | 2003-07-09 |
CN1592656B (zh) | 2012-07-11 |
WO2003053580A1 (de) | 2003-07-03 |
US7319175B2 (en) | 2008-01-15 |
EP1497029A1 (de) | 2005-01-19 |
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