JP7411124B2 - ヘキサフルオロ－１，３－ブタジエン及びその中間体の製造方法 - Google Patents
ヘキサフルオロ－１，３－ブタジエン及びその中間体の製造方法 Download PDFInfo
- Publication number
- JP7411124B2 JP7411124B2 JP2022577538A JP2022577538A JP7411124B2 JP 7411124 B2 JP7411124 B2 JP 7411124B2 JP 2022577538 A JP2022577538 A JP 2022577538A JP 2022577538 A JP2022577538 A JP 2022577538A JP 7411124 B2 JP7411124 B2 JP 7411124B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- butadiene
- dibromo
- chloro
- hexafluoro
- 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.)
- Active
Links
- LGPPATCNSOSOQH-UHFFFAOYSA-N 1,1,2,3,4,4-hexafluorobuta-1,3-diene Chemical compound FC(F)=C(F)C(F)=C(F)F LGPPATCNSOSOQH-UHFFFAOYSA-N 0.000 title claims description 53
- 238000004519 manufacturing process Methods 0.000 title claims description 49
- 239000000543 intermediate Substances 0.000 title description 29
- 238000006243 chemical reaction Methods 0.000 claims description 73
- 239000003999 initiator Substances 0.000 claims description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- OVZATIUQXBLIQT-UHFFFAOYSA-N 1,2-dibromo-1-chloro-1,2,2-trifluoroethane Chemical compound FC(F)(Br)C(F)(Cl)Br OVZATIUQXBLIQT-UHFFFAOYSA-N 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- 229910052740 iodine Inorganic materials 0.000 claims description 13
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 12
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 12
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 10
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical group CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 claims description 9
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 9
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 9
- 239000011630 iodine Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 239000003880 polar aprotic solvent Substances 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 238000005695 dehalogenation reaction Methods 0.000 claims description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000001307 helium Substances 0.000 claims description 4
- 229910052734 helium Inorganic materials 0.000 claims description 4
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims 2
- 229940102001 zinc bromide Drugs 0.000 claims 1
- 238000000034 method Methods 0.000 description 31
- 239000007789 gas Substances 0.000 description 14
- 230000008569 process Effects 0.000 description 14
- 239000002994 raw material Substances 0.000 description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 239000011737 fluorine Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- UUAGAQFQZIEFAH-UHFFFAOYSA-N chlorotrifluoroethylene Chemical group FC(F)=C(F)Cl UUAGAQFQZIEFAH-UHFFFAOYSA-N 0.000 description 5
- 238000005530 etching Methods 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 230000000977 initiatory effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- PFSLUJSDDNGKIZ-UHFFFAOYSA-N 1,4-dibromo-2,3-dichloro-1,1,2,3,4,4-hexafluorobutane Chemical compound FC(F)(Br)C(F)(Cl)C(F)(Cl)C(F)(F)Br PFSLUJSDDNGKIZ-UHFFFAOYSA-N 0.000 description 4
- AYCANDRGVPTASA-UHFFFAOYSA-N 1-bromo-1,2,2-trifluoroethene Chemical group FC(F)=C(F)Br AYCANDRGVPTASA-UHFFFAOYSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- YLYSNAJRDKXSGQ-UHFFFAOYSA-N 1,2,4-tribromo-3-chloro-1,1,2,3,4,4-hexafluorobutane Chemical compound C(C(C(F)(F)Br)(F)Br)(C(F)(F)Br)(F)Cl YLYSNAJRDKXSGQ-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- QZRGKCOWNLSUDK-UHFFFAOYSA-N Iodochlorine Chemical compound ICl QZRGKCOWNLSUDK-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CNRGDMNPQKVTJP-UHFFFAOYSA-N 1,1,4,4-tetrachloro-2,3-difluorobuta-1,3-diene Chemical compound C(=C(Cl)Cl)(C(=C(Cl)Cl)F)F CNRGDMNPQKVTJP-UHFFFAOYSA-N 0.000 description 2
- IRHYACQPDDXBCB-UHFFFAOYSA-N 1,2,3,4-tetrachloro-1,1,2,3,4,4-hexafluorobutane Chemical compound FC(F)(Cl)C(F)(Cl)C(F)(Cl)C(F)(F)Cl IRHYACQPDDXBCB-UHFFFAOYSA-N 0.000 description 2
- PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 2
- BZBLUUDREZEDDJ-UHFFFAOYSA-N 2,2,3,3-tetrachloro-1,1,1,4,4,4-hexafluorobutane Chemical compound FC(F)(F)C(Cl)(Cl)C(Cl)(Cl)C(F)(F)F BZBLUUDREZEDDJ-UHFFFAOYSA-N 0.000 description 2
- AFLIPEBFYDIRNJ-UHFFFAOYSA-N FC(F)=C(F)[Zn] Chemical compound FC(F)=C(F)[Zn] AFLIPEBFYDIRNJ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910000856 hastalloy Inorganic materials 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000010907 mechanical stirring Methods 0.000 description 2
- 150000004968 peroxymonosulfuric acids Chemical class 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- KHFGPBNEILANTD-UHFFFAOYSA-N 1,1,1,2-tetrachloro-2,3,3,4,4,4-hexafluorobutane Chemical compound FC(F)(F)C(F)(F)C(F)(Cl)C(Cl)(Cl)Cl KHFGPBNEILANTD-UHFFFAOYSA-N 0.000 description 1
- HCUGPHQZDLROAY-UHFFFAOYSA-N 1,2-dichloro-1,1,2-trifluoro-2-iodoethane Chemical compound FC(F)(Cl)C(F)(Cl)I HCUGPHQZDLROAY-UHFFFAOYSA-N 0.000 description 1
- LMHAGAHDHRQIMB-UHFFFAOYSA-N 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(Cl)C1(F)Cl LMHAGAHDHRQIMB-UHFFFAOYSA-N 0.000 description 1
- KWXXMLHQBFNLOR-UHFFFAOYSA-N 3,4-dichloro-1,1,2,3,4,4-hexafluorobut-1-ene Chemical compound FC(F)=C(F)C(F)(Cl)C(F)(F)Cl KWXXMLHQBFNLOR-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000000382 dechlorinating effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- UHCBBWUQDAVSMS-UHFFFAOYSA-N fluoroethane Chemical compound CCF UHCBBWUQDAVSMS-UHFFFAOYSA-N 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007116 intermolecular coupling reaction Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
-
- 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
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/272—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions
- C07C17/278—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by addition reactions of only halogenated hydrocarbons
-
- 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
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- 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
- C07C19/14—Acyclic saturated compounds containing halogen atoms containing fluorine and bromine
-
- 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
- C07C21/19—Halogenated dienes
- C07C21/20—Halogenated butadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010552671.4 | 2020-06-17 | ||
| CN202010552671.4A CN111675597B (zh) | 2020-06-17 | 2020-06-17 | 一种六氟-1,3-丁二烯及其中间体的制备方法 |
| PCT/CN2021/100290 WO2021254372A1 (zh) | 2020-06-17 | 2021-06-16 | 一种六氟-1,3-丁二烯及其中间体的制备方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2023538185A JP2023538185A (ja) | 2023-09-07 |
| JP7411124B2 true JP7411124B2 (ja) | 2024-01-10 |
Family
ID=72435935
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2022577538A Active JP7411124B2 (ja) | 2020-06-17 | 2021-06-16 | ヘキサフルオロ－１，３－ブタジエン及びその中間体の製造方法 |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP7411124B2 (zh) |
| KR (1) | KR20230029802A (zh) |
| CN (1) | CN111675597B (zh) |
| WO (1) | WO2021254372A1 (zh) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111675597B (zh) * | 2020-06-17 | 2022-03-29 | 浙江省化工研究院有限公司 | 一种六氟-1,3-丁二烯及其中间体的制备方法 |
| CN113004118A (zh) * | 2021-02-07 | 2021-06-22 | 中船重工（邯郸）派瑞特种气体有限公司 | 一种利用高沸点强极性溶剂制备六氟丁二烯的方法 |
| KR20230043278A (ko) * | 2021-09-23 | 2023-03-31 | 주식회사 진성이엔지 | 1,4-디브로모-2,3-디클로로헥사플루오로부탄 제조 방법 및 이를 이용한 헥사플루오로-1,3-부타디엔 제조 방법 |
| CN115572209A (zh) * | 2022-10-21 | 2023-01-06 | 广东电网有限责任公司 | 一种2,4-二氯-1,1,1,4,4-五氟丁烷的制备方法 |
| CN116874344B (zh) * | 2023-09-06 | 2023-12-08 | 北京宇极科技发展有限公司 | 连续制备e-1,1,1,4,5,5,5-七氟-4-(三氟甲基)戊-2-烯的方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB774103A (en) | 1952-09-15 | 1957-05-08 | Robert Neville Haszeldine | Halogenated organic compounds |
| CN104844411A (zh) | 2015-04-03 | 2015-08-19 | 北京宇极科技发展有限公司 | 一种合成六氟-1,3-丁二烯的方法 |
| CN105399599A (zh) | 2015-12-28 | 2016-03-16 | 浙江工业大学 | 一种制备六氟丁二烯的方法 |
| CN106336342A (zh) | 2016-07-19 | 2017-01-18 | 浙江博瑞电子科技有限公司 | 一种碘和氯气为原料制备六氟丁二烯的方法 |
| WO2019240248A1 (ja) | 2018-06-15 | 2019-12-19 | ダイキン工業株式会社 | パーフルオロアルカジエン化合物の製造方法 |
| CN111233619A (zh) | 2020-03-17 | 2020-06-05 | 河北师范大学 | 一种合成4-卤代-1,1,2-三氟-1-丁烯的方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111675597B (zh) * | 2020-06-17 | 2022-03-29 | 浙江省化工研究院有限公司 | 一种六氟-1,3-丁二烯及其中间体的制备方法 |
-
2020
- 2020-06-17 CN CN202010552671.4A patent/CN111675597B/zh active Active
-
2021
- 2021-06-16 WO PCT/CN2021/100290 patent/WO2021254372A1/zh active Application Filing
- 2021-06-16 JP JP2022577538A patent/JP7411124B2/ja active Active
- 2021-06-16 KR KR1020237001759A patent/KR20230029802A/ko unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB774103A (en) | 1952-09-15 | 1957-05-08 | Robert Neville Haszeldine | Halogenated organic compounds |
| CN104844411A (zh) | 2015-04-03 | 2015-08-19 | 北京宇极科技发展有限公司 | 一种合成六氟-1,3-丁二烯的方法 |
| CN105399599A (zh) | 2015-12-28 | 2016-03-16 | 浙江工业大学 | 一种制备六氟丁二烯的方法 |
| CN106336342A (zh) | 2016-07-19 | 2017-01-18 | 浙江博瑞电子科技有限公司 | 一种碘和氯气为原料制备六氟丁二烯的方法 |
| WO2019240248A1 (ja) | 2018-06-15 | 2019-12-19 | ダイキン工業株式会社 | パーフルオロアルカジエン化合物の製造方法 |
| CN111233619A (zh) | 2020-03-17 | 2020-06-05 | 河北师范大学 | 一种合成4-卤代-1,1,2-三氟-1-丁烯的方法 |
Non-Patent Citations (2)
| Title |
|---|
| Tarrant, Paul et al.，Free radical additions involving fluorine compounds. V. Reactions of 1,2-dibromo-2-chloro- and 1,2-dichloro-2-iodo-1,1,2-trifluoroethane with Fluoroolefins，Journal of the American Chemical Society，1955年07月05日，Vol.77,No.13，3640-3642 |
| V.Dedek et al.，Addition of 1,2-dibromo-1-chlorotrifluoroethane to chloro tri fluoroethylene induced by UV-radiation. Synthesis of perfluoro-1,3-butadiene and perfluoro-1,3,5-hexatriene，Journal of Fluorine Chemistry，1986年05月31日，Vol.31, No.4，363-379 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR20230029802A (ko) | 2023-03-03 |
| JP2023538185A (ja) | 2023-09-07 |
| CN111675597B (zh) | 2022-03-29 |
| CN111675597A (zh) | 2020-09-18 |
| WO2021254372A1 (zh) | 2021-12-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7411124B2 (ja) | ヘキサフルオロ－１，３－ブタジエン及びその中間体の製造方法 | |
| JP4854128B2 (ja) | フルオロビニルエーテルおよびそれから得ることができるポリマー | |
| CN113227025B (zh) | 环丁烯的制造方法 | |
| CA2724968C (en) | Polyfluoro-1-alkene and method for producing the same | |
| KR20180068991A (ko) | 작용성화된 플루오르화 코폴리머 | |
| JP4207001B2 (ja) | ポリフルオロアルキルエチルアイオダイドの製造方法 | |
| CN105272818B (zh) | 制备全氟丁二烯的新方法 | |
| CN103420783B (zh) | 一种1,1,1,4,4,4-六氟-2-丁炔的制备方法 | |
| RU2815788C1 (ru) | Способ получения гексафтор-1,3-бутадиена и его промежуточного соединения | |
| JP5301984B2 (ja) | １，４−ビス（ブロモジフルオロメチル）テトラフルオロベンゼンおよびその製造方法 | |
| JP2008044863A (ja) | ペルフルオロ有機過酸化物ならびにその製造方法、および重合体の製造方法 | |
| CN101786977A (zh) | 一种全氟烷基酰基过氧化物的制备方法 | |
| CN112552148B (zh) | 全氟己酮生产过程中副产物2-氯-1,1,1,3,3,3-六氟丙烷的资源化利用方法 | |
| CN117222613A (zh) | 氟代炔烃化合物的制造方法 | |
| CN109956847B (zh) | 一种含氟环丁烯的水相制备方法 | |
| KR20220020939A (ko) | 알칸의 제조 방법 | |
| JP5359144B2 (ja) | フルオロオレフィンアイオダイド混合物およびその製造法 | |
| JP4290058B2 (ja) | 含フッ素エーテル化合物の製造方法 | |
| JP2503552B2 (ja) | 新規含フッ素化合物及びその製造方法 | |
| JP2006232704A (ja) | 新規なフルオロスルホニル基含有化合物 | |
| CN111655676A (zh) | 1,3-二氧戊环化合物及全氟(2,2-二甲基-1,3-二氧杂环戊烯)的制造方法 | |
| JP4290093B2 (ja) | 含フッ素エーテル化合物の製造方法 | |
| JP6610625B2 (ja) | １，２−ジクロロ−１，２−ジフルオロエタン（ＨＣＦＣ−１３２）の製造方法、１−クロロ−１，２−ジフルオロエチレン（ＨＣＦＯ−１１２２ａ）の製造方法、及びＨＣＦＣ−１３２の分離方法 | |
| CN118146066A (zh) | 一种六氟丁二烯的制备方法 | |
| CN117700306A (zh) | 氢氟醚的生产方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20221222 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20230823 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20231215 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20231222 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 7411124 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |