KR20110049820A - 퍼플루오르화 시스-알켄 제조방법 - Google Patents

퍼플루오르화 시스-알켄 제조방법 Download PDF

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Publication number: KR20110049820A
Authority: KR; South Korea
Prior art keywords: cis; perfluorinated; hexafluoro; aromatic amine; alkyne
Prior art date: 2008-07-31
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn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

KR1020117004186A

Other languages

English (en)

Korean (ko)

Inventor

마이클 밴 더 푸이

징-지 마

Original Assignee

허니웰 인터내셔널 인코포레이티드

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.)

2008-07-31

Filing date

2009-07-27

Publication date

2011-05-12

2009-07-27 Application filed by 허니웰 인터내셔널 인코포레이티드 filed Critical 허니웰 인터내셔널 인코포레이티드

2011-05-12 Publication of KR20110049820A publication Critical patent/KR20110049820A/ko

Status Withdrawn legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 23
239000003054 catalyst Substances 0.000 claims abstract description 33
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 13
150000001345 alkine derivatives Chemical class 0.000 claims abstract description 13
239000001257 hydrogen Substances 0.000 claims abstract description 13
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
239000003607 modifier Substances 0.000 claims abstract description 12
150000004982 aromatic amines Chemical class 0.000 claims abstract description 11
229910052763 palladium Inorganic materials 0.000 claims abstract description 10
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 5
229910052799 carbon Inorganic materials 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 3
239000002184 metal Chemical class 0.000 claims description 10
229910052751 metal Inorganic materials 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 7
150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
WBCLXFIDEDJGCC-UHFFFAOYSA-N hexafluoro-2-butyne Chemical group FC(F)(F)C#CC(F)(F)F WBCLXFIDEDJGCC-UHFFFAOYSA-N 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
150000001298 alcohols Chemical class 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 3
125000003118 aryl group Chemical group 0.000 claims description 3
150000001875 compounds Chemical class 0.000 claims description 3
150000002148 esters Chemical class 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
229910052802 copper Inorganic materials 0.000 claims description 2
239000010949 copper Substances 0.000 claims description 2
229910052742 iron Inorganic materials 0.000 claims description 2
150000002739 metals Chemical class 0.000 claims description 2
229910052707 ruthenium Inorganic materials 0.000 claims description 2
150000003839 salts Chemical class 0.000 claims description 2
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 2
239000011135 tin Substances 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
238000006722 reduction reaction Methods 0.000 description 22
230000009467 reduction Effects 0.000 description 17
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 8
239000000047 product Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
NLOLSXYRJFEOTA-UPHRSURJSA-N (z)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C/C(F)(F)F NLOLSXYRJFEOTA-UPHRSURJSA-N 0.000 description 5
NLOLSXYRJFEOTA-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)C=CC(F)(F)F NLOLSXYRJFEOTA-UHFFFAOYSA-N 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000000463 material Substances 0.000 description 5
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
CXIGIYYQHHRBJC-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)CCC(F)(F)F CXIGIYYQHHRBJC-UHFFFAOYSA-N 0.000 description 3
VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
150000001336 alkenes Chemical class 0.000 description 3
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 3
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 3
229910000019 calcium carbonate Inorganic materials 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
239000012530 fluid Substances 0.000 description 3
239000000203 mixture Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000010792 warming Methods 0.000 description 3
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
BSRRYOGYBQJAFP-UHFFFAOYSA-N 1,1,1,2,2,3-hexafluorobutane Chemical compound CC(F)C(F)(F)C(F)(F)F BSRRYOGYBQJAFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
-1 Platinum Metals Chemical class 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 2
235000013844 butane Nutrition 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
230000008859 change Effects 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical class CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
NLOLSXYRJFEOTA-OWOJBTEDSA-N (e)-1,1,1,4,4,4-hexafluorobut-2-ene Chemical compound FC(F)(F)\C=C\C(F)(F)F NLOLSXYRJFEOTA-OWOJBTEDSA-N 0.000 description 1
AAXQTNTZMACLDP-UHFFFAOYSA-N 1,1,1,4,4,4-hexafluoro-2-iodobut-2-ene Chemical compound FC(F)(F)C=C(I)C(F)(F)F AAXQTNTZMACLDP-UHFFFAOYSA-N 0.000 description 1
SXKNYNUXUHCUHX-UHFFFAOYSA-N 1,1,2,3,3,4-hexafluorobut-1-ene Chemical compound FCC(F)(F)C(F)=C(F)F SXKNYNUXUHCUHX-UHFFFAOYSA-N 0.000 description 1
DXPCVBMFVUHPOU-UHFFFAOYSA-N 1,3,3,4,4,4-hexafluorobut-1-yne Chemical compound FC#CC(F)(F)C(F)(F)F DXPCVBMFVUHPOU-UHFFFAOYSA-N 0.000 description 1
WFOIWBGKCSYBJN-UHFFFAOYSA-N 1-fluorobut-1-ene Chemical compound CCC=CF WFOIWBGKCSYBJN-UHFFFAOYSA-N 0.000 description 1
AYEMXGNOKZRIOC-UHFFFAOYSA-N 3-(4-methoxyphenyl)prop-2-ynoic acid Chemical compound COC1=CC=C(C#CC(O)=O)C=C1 AYEMXGNOKZRIOC-UHFFFAOYSA-N 0.000 description 1
239000004604 Blowing Agent Substances 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000001273 butane Substances 0.000 description 1
YTIVTFGABIZHHX-UHFFFAOYSA-N butynedioic acid Chemical compound OC(=O)C#CC(O)=O YTIVTFGABIZHHX-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006298 dechlorination reaction Methods 0.000 description 1
239000003989 dielectric material Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000006317 isomerization reaction Methods 0.000 description 1
239000011981 lindlar catalyst Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
239000003380 propellant Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000006456 reductive dimerization reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
239000003507 refrigerant Substances 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
239000012808 vapor phase Substances 0.000 description 1
238000013022 venting Methods 0.000 description 1

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
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/02—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the alkali- or alkaline earth metals or beryllium
- B01J23/04—Alkali metals
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
- 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
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/58—Platinum group metals with alkali- or alkaline earth metals
- 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
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead

Landscapes

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)
Catalysts (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

KR1020117004186A 2008-07-31 2009-07-27 퍼플루오르화 시스-알켄 제조방법 Withdrawn KR20110049820A (ko)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US8507708P	2008-07-31	2008-07-31
US61/085,077		2008-07-31

Publications (1)

Publication Number	Publication Date
KR20110049820A true KR20110049820A (ko)	2011-05-12

Family

ID=41610923

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
KR1020117004186A Withdrawn KR20110049820A (ko)	2008-07-31	2009-07-27	퍼플루오르화 시스-알켄 제조방법

Country Status (6)

Country	Link
EP (1)	EP2310347A4 (fr)
JP (1)	JP2011529893A (fr)
KR (1)	KR20110049820A (fr)
CN (1)	CN102112420A (fr)
MX (1)	MX2011000995A (fr)
WO (1)	WO2010014548A2 (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2722711A1 (fr) *	2008-05-23	2009-11-26	E.I. Du Pont De Nemours And Company	Procede a selectivite elevee pour preparer des dihydrofluoralcenes
US8461401B2 (en) *	2010-03-26	2013-06-11	Honeywell International Inc.	Method for making hexafluoro-2-butene
US8530709B2 (en) *	2010-05-21	2013-09-10	Honeywell International Inc.	Process for the production of fluorinated alkenes
US8901360B2 (en) *	2010-05-21	2014-12-02	Honeywell International Inc.	Process for cis 1,1,1,4,4,4-hexafluoro-2-butene
US8524955B2 (en)	2010-05-21	2013-09-03	Honeywell International Inc.	Process for the preparation of hexafluoro-2-butyne
JP5598910B2 (ja) *	2010-06-14	2014-10-01	独立行政法人産業技術総合研究所	フッ素化合物の製造方法
US8871987B2 (en)	2010-12-10	2014-10-28	E I Du Pont De Nemours And Company	Purification of cis-1,1,1,4,4,4-hexafluoro-2-butene via extractive distillation
US9758452B2 (en) *	2014-02-07	2017-09-12	The Chemours Company Fc, Llc	Integrated process for the production of Z-1,1,1,4,4,4-hexafluoro-2-butene
CN106008147B (zh) *	2016-05-23	2018-11-02	北京宇极科技发展有限公司	Z-1，1，1，4，4，4-六氟-2-丁烯的制备方法
CN116060010B (zh) *	2023-03-31	2023-07-04	北京宇极科技发展有限公司	引发剂、氟化催化剂以及e-1,1,1,4,4,4-六氟-2-丁烯的制备方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS6014003B2 (ja) *	1978-11-08	1985-04-11	信越化学工業株式会社	シス−オレフィン化合物の選択的製造方法
JPS56133230A (en) *	1980-03-21	1981-10-19	Otsuka Pharmaceut Co Ltd	Preparation of cis-olefin
US5587348A (en) *	1995-04-19	1996-12-24	Phillips Petroleum Company	Alkyne hydrogenation catalyst and process
DE19526473A1 (de) *	1995-07-20	1997-01-23	Basf Ag	Verfahren zur Herstellung von Alkenen durch partielle Hydrierung von Alkinen an Festbett-Palladium-Katalysatoren
DE19962907A1 (de) *	1999-12-23	2001-07-05	Basf Ag	Verfahren zur Herstellung von C¶10¶-C¶30¶-Alkenen durch partielle Hydrierung von Alkinen an Festbett-Palladium-Trägerkatalysatoren

2009
- 2009-07-27 EP EP09803441A patent/EP2310347A4/fr not_active Withdrawn
- 2009-07-27 WO PCT/US2009/051847 patent/WO2010014548A2/fr not_active Ceased
- 2009-07-27 CN CN2009801300180A patent/CN102112420A/zh active Pending
- 2009-07-27 JP JP2011521221A patent/JP2011529893A/ja active Pending
- 2009-07-27 KR KR1020117004186A patent/KR20110049820A/ko not_active Withdrawn
- 2009-07-27 MX MX2011000995A patent/MX2011000995A/es not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP2310347A2 (fr)	2011-04-20
WO2010014548A2 (fr)	2010-02-04
EP2310347A4 (fr)	2012-10-31
JP2011529893A (ja)	2011-12-15
MX2011000995A (es)	2011-03-04
CN102112420A (zh)	2011-06-29
WO2010014548A3 (fr)	2010-04-01

Legal Events

Date	Code	Title	Description
2011-02-23	PA0105	International application	Patent event date: 20110223 Patent event code: PA01051R01D Comment text: International Patent Application
2011-05-12	PG1501	Laying open of application
2014-08-28	PC1203	Withdrawal of no request for examination
2014-08-28	WITN	Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid

Publication	Publication Date	Title
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