JP6930962B2 - Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンのe−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンへの接触異性化 - Google Patents
Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンのe−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンへの接触異性化 Download PDFInfo
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- JP6930962B2 JP6930962B2 JP2018506404A JP2018506404A JP6930962B2 JP 6930962 B2 JP6930962 B2 JP 6930962B2 JP 2018506404 A JP2018506404 A JP 2018506404A JP 2018506404 A JP2018506404 A JP 2018506404A JP 6930962 B2 JP6930962 B2 JP 6930962B2
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- mzz
- catalyst
- hexafluoro
- butene
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- 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
-
- 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
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- 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
- B01J27/10—Chlorides
-
- 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
- B01J27/12—Fluorides
-
- 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
- B01J27/125—Halogens; Compounds thereof with scandium, yttrium, aluminium, gallium, indium or thallium
-
- 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
- B01J27/132—Halogens; Compounds thereof with chromium, molybdenum, tungsten or polonium
-
- 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
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00029—Batch processes
-
- 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
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00049—Controlling or regulating processes
- B01J2219/00051—Controlling the temperature
-
- 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
- Y02P20/582—Recycling of unreacted starting or intermediate materials
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Description
触媒であるSbCl5(5g、0.016モル)又はTaCl5(6.15g、0.016モル)を、210mLのHastelloy C反応器に添加し、続いて、HFを添加した(20g、1モル)。反応混合物を1時間かけて100℃に加熱し、0℃に冷却した。Z−1336mzz(30g、0.18モル)を添加し、槽及び反応を20時間かけて100℃に加熱し直した。50gの氷水を添加して、反応をクエンチした。生成物をGCによって分析した。
五フッ化アンチモン(SbF5、1g)を、ドライボックス内の50mLの丸底フラスコに入れた。反応槽をドラフトに移し、熱電対、ドライアイス凝縮器、添加漏斗、及び電磁撹拌棒を備えていた。20gのシス−HFO−1336mzz(0.3モル%のトランス異性体を含有)を、窒素ブランケット下で15分間かけて0℃の反応槽に添加した。反応混合物を3日間周囲温度で撹拌した(反応槽を−78℃で一晩維持し、反応を次の朝再開させた)。シス−HFO−1336mzzの変換をGC及び19F NMRによってモニタリングした。3日間後(周囲温度で合計〜28時間)、シス/トランス比は0.4:99.6であることが見出された。
アルミニウムクロロフルオリド(AlClxFy、「ACF」、0.4g、米国特許第5,162,594号に従って調製)を、ドライボックス内の50mLの丸底フラスコに入れた。反応槽をドラフトに移し、熱電対、ドライアイス凝縮器、添加漏斗、及び電磁撹拌棒を備えていた。20gの冷シス−HFO−1336mzz(0.1モル%のトランス異性体を含有)を、窒素ブランケット下で15分間かけて20℃の反応槽に添加した。
触媒の調製及び活性化
Inconel(登録商標)(1.3センチメートル(0.5インチ)OD)管に、14,000kg(30,000lb)で水和酸化クロム粉末を圧縮することによって形成された6ccの塩化クロムを添加した。得られた塊を粉砕し、12/20メッシュで篩った。
50℃で予熱したZ−1,1,1,4,4,4−ヘキサフルオロ−2−ブテン(Z−HFO−1336mzz)流を管反応器に送り込んだ。反応器排出液の一部を、一連のバルブに通過させて、GCMSにより分析した。
Claims (4)
- Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンをE−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンに異性化する方法であって、
(a)Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンを含む出発物質を提供する工程と、
(b)反応ゾーンにおいて前記出発物質を好適な触媒と接触させて、E−HFO−1336mzzを生成する工程と、任意追加的に、
(c)前記E−HFO−1336mzzを回収する工程と、を含む、方法であって、
前記接触工程が気相中で行われ、前記触媒はオキシフッ化クロムを含む、方法。 - 前記触媒との接触工程(b)は、150〜400℃で行われる請求項1に記載の方法。
- 前記E−HFO−1336mzzを回収する工程を更に含む、請求項1又は2に記載の方法。
- 生成物中に未反応が存在し、このような未反応Z−1336mzzが、生成物から分離され、前記反応ゾーンに再利用される、請求項1又は2に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201562202382P | 2015-08-07 | 2015-08-07 | |
US62/202,382 | 2015-08-07 | ||
PCT/US2016/045573 WO2017027323A1 (en) | 2015-08-07 | 2016-08-04 | Catalytic isomerization of z-1,1,1,4,4,4-hexafluoro-2-butene to e-1,1,1,4,4,4-hexafluoro-2-butene |
Publications (3)
Publication Number | Publication Date |
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JP2018522908A JP2018522908A (ja) | 2018-08-16 |
JP2018522908A5 JP2018522908A5 (ja) | 2019-08-29 |
JP6930962B2 true JP6930962B2 (ja) | 2021-09-01 |
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Family Applications (1)
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JP2018506404A Active JP6930962B2 (ja) | 2015-08-07 | 2016-08-04 | Z−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンのe−1,1,1,4,4,4−ヘキサフルオロ−2−ブテンへの接触異性化 |
Country Status (7)
Country | Link |
---|---|
US (1) | US10479745B2 (ja) |
EP (2) | EP3663274A1 (ja) |
JP (1) | JP6930962B2 (ja) |
KR (1) | KR102664130B1 (ja) |
CN (1) | CN107848918B (ja) |
MX (2) | MX2018001489A (ja) |
WO (1) | WO2017027323A1 (ja) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
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KR20200051590A (ko) * | 2017-09-11 | 2020-05-13 | 더 케무어스 컴퍼니 에프씨, 엘엘씨 | 플루오르화수소 및 플루오로카본을 포함하는 공비 조성물 |
JP7321149B2 (ja) * | 2017-10-10 | 2023-08-04 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | HFO-1336mzz(Z)及びHFO-1336mzz(E)を含有する熱可塑性発泡体を製造するプロセス |
CN107602340B (zh) * | 2017-10-17 | 2020-05-15 | 北京宇极科技发展有限公司 | 气相异构化制备全氟二烯烃和全氟炔烃的方法 |
CN111433177B (zh) * | 2017-12-04 | 2024-04-16 | 科慕埃弗西有限公司 | 用于制备1,1,3-三氯-4,4,4-三氟丁-1-烯和(e)-1,1,1,4,4,4-六氟丁-2-烯的方法和中间体 |
CN108727155B (zh) * | 2018-06-19 | 2021-01-01 | 北京宇极科技发展有限公司 | E-1,1,1,4,4,4-六氟-2-丁烯的制备方法 |
US20230373888A1 (en) * | 2020-10-15 | 2023-11-23 | Resonac Corporation | Method for storing fluoro-2-butene |
JPWO2022080275A1 (ja) * | 2020-10-15 | 2022-04-21 | ||
IL302121A (en) * | 2020-10-15 | 2023-06-01 | Resonac Corp | METHOD FOR STORING FLUORO-2-BUTENE |
CN112811975B (zh) * | 2021-04-22 | 2021-07-30 | 泉州宇极新材料科技有限公司 | 气相异构化制备z-1-r-3,3,3-三氟丙烯的方法 |
CN118055915A (zh) * | 2021-10-06 | 2024-05-17 | 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 |
CN114292158B (zh) * | 2021-12-01 | 2024-01-02 | 西安近代化学研究所 | 一种制备顺式-1,1,1,4,4,4-六氟-2-丁烯的方法 |
CN114262255B (zh) * | 2021-12-01 | 2023-10-20 | 西安近代化学研究所 | 一种合成反式-1,1,1,4,4,4-六氟-2-丁烯的方法 |
TW202346449A (zh) | 2022-04-22 | 2023-12-01 | 美商科慕Fc有限責任公司 | 包含e-1,1,1,4,4,4-六氟-2-丁烯之氟丁烯組成物及其用途 |
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GB0721991D0 (en) * | 2007-11-09 | 2007-12-19 | Ineos Fluor Holdings Ltd | Preparation method |
EP2260015B1 (en) | 2008-03-19 | 2012-10-31 | E. I. du Pont de Nemours and Company | Process for making 1,1,1,4,4,4-hexafluoro-2-butene |
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- 2016-08-04 EP EP20154457.4A patent/EP3663274A1/en active Pending
- 2016-08-04 US US15/746,033 patent/US10479745B2/en active Active
- 2016-08-04 KR KR1020187006256A patent/KR102664130B1/ko active IP Right Grant
- 2016-08-04 EP EP16757399.7A patent/EP3331846B1/en active Active
- 2016-08-04 WO PCT/US2016/045573 patent/WO2017027323A1/en active Application Filing
- 2016-08-04 CN CN201680046175.3A patent/CN107848918B/zh active Active
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Publication number | Publication date |
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CN107848918B (zh) | 2021-12-21 |
EP3331846A1 (en) | 2018-06-13 |
EP3663274A1 (en) | 2020-06-10 |
JP2018522908A (ja) | 2018-08-16 |
MX2023009585A (es) | 2023-08-23 |
US20180215690A1 (en) | 2018-08-02 |
EP3331846B1 (en) | 2020-10-28 |
KR20180038006A (ko) | 2018-04-13 |
CN107848918A (zh) | 2018-03-27 |
US10479745B2 (en) | 2019-11-19 |
MX2018001489A (es) | 2018-04-24 |
KR102664130B1 (ko) | 2024-05-10 |
WO2017027323A1 (en) | 2017-02-16 |
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