CN111517915A - 2,3,3,3-四氟丙烯的生产方法 - Google Patents
2,3,3,3-四氟丙烯的生产方法 Download PDFInfo
- Publication number
- CN111517915A CN111517915A CN202010333467.3A CN202010333467A CN111517915A CN 111517915 A CN111517915 A CN 111517915A CN 202010333467 A CN202010333467 A CN 202010333467A CN 111517915 A CN111517915 A CN 111517915A
- Authority
- CN
- China
- Prior art keywords
- stream
- line
- distillation
- withdrawing
- compressed
- 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.)
- Pending
Links
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000004519 manufacturing process Methods 0.000 title description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 54
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 54
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 53
- 239000007788 liquid Substances 0.000 claims abstract description 53
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 51
- 238000006243 chemical reaction Methods 0.000 claims abstract description 31
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000007789 gas Substances 0.000 claims abstract description 19
- 238000001816 cooling Methods 0.000 claims abstract description 14
- 238000004821 distillation Methods 0.000 claims description 97
- 238000000926 separation method Methods 0.000 claims description 16
- 150000002894 organic compounds Chemical class 0.000 claims description 10
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 claims description 9
- 238000009833 condensation Methods 0.000 claims description 9
- 230000005494 condensation Effects 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 238000000746 purification Methods 0.000 claims description 7
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 claims description 6
- 229950000188 halopropane Drugs 0.000 claims description 6
- 230000003197 catalytic effect Effects 0.000 claims description 5
- 238000010908 decantation Methods 0.000 claims description 5
- 238000000605 extraction Methods 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims description 4
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 claims description 4
- 239000012495 reaction gas Substances 0.000 claims description 4
- 238000007086 side reaction Methods 0.000 claims description 4
- OWXJKYNZGFSVRC-NSCUHMNNSA-N (e)-1-chloroprop-1-ene Chemical compound C\C=C\Cl OWXJKYNZGFSVRC-NSCUHMNNSA-N 0.000 claims description 3
- UMGQVBVEWTXECF-UHFFFAOYSA-N 1,1,2,3-tetrachloroprop-1-ene Chemical compound ClCC(Cl)=C(Cl)Cl UMGQVBVEWTXECF-UHFFFAOYSA-N 0.000 claims description 3
- PQUUGVDRLWLNGR-UHFFFAOYSA-N 2,3,3,3-tetrachloroprop-1-ene Chemical compound ClC(=C)C(Cl)(Cl)Cl PQUUGVDRLWLNGR-UHFFFAOYSA-N 0.000 claims description 3
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 3
- 230000005493 condensed matter Effects 0.000 claims 1
- 239000003054 catalyst Substances 0.000 description 20
- 239000000543 intermediate Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 8
- 239000011651 chromium Substances 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- 230000004913 activation Effects 0.000 description 6
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 6
- -1 Fluoro Chemical group 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 150000004812 organic fluorine compounds Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052804 chromium Inorganic materials 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 3
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- IYFMQUDCYNWFTL-UHFFFAOYSA-N 1,1,2,2,3-pentachloropropane Chemical compound ClCC(Cl)(Cl)C(Cl)Cl IYFMQUDCYNWFTL-UHFFFAOYSA-N 0.000 description 2
- OPLWDQVQIWKMSG-UHFFFAOYSA-N 1-chloro-1-fluoropropane Chemical compound CCC(F)Cl OPLWDQVQIWKMSG-UHFFFAOYSA-N 0.000 description 2
- BGRKGHSKCFAPCL-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)phenol Chemical compound CCC(C)(C)C1=CC=CC=C1O BGRKGHSKCFAPCL-UHFFFAOYSA-N 0.000 description 2
- SMCNZLDHTZESTK-UHFFFAOYSA-N 2-chloro-1,1,1,2-tetrafluoropropane Chemical compound CC(F)(Cl)C(F)(F)F SMCNZLDHTZESTK-UHFFFAOYSA-N 0.000 description 2
- CNNJBYUJTYGLGG-UHFFFAOYSA-N 2-chloro-1,1,1,3-tetrafluoropropane Chemical compound FCC(Cl)C(F)(F)F CNNJBYUJTYGLGG-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 239000004411 aluminium Substances 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- BSKAIKMQTLKUOW-UHFFFAOYSA-N chromium;fluoro hypofluorite Chemical compound [Cr].FOF BSKAIKMQTLKUOW-UHFFFAOYSA-N 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- XMGQYMWWDOXHJM-SNVBAGLBSA-N (-)-α-limonene Chemical compound CC(=C)[C@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-SNVBAGLBSA-N 0.000 description 1
- CDOOAUSHHFGWSA-OWOJBTEDSA-N (e)-1,3,3,3-tetrafluoroprop-1-ene Chemical compound F\C=C\C(F)(F)F CDOOAUSHHFGWSA-OWOJBTEDSA-N 0.000 description 1
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical class CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001398 aluminium Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 239000007806 chemical reaction intermediate Substances 0.000 description 1
- 229910021563 chromium fluoride Inorganic materials 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 229910052593 corundum Inorganic materials 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 238000007700 distillative separation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052736 halogen Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940110728 nitrogen / oxygen Drugs 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 229910001845 yogo sapphire Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Images
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
-
- 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
-
- 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
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J1/00—Processes or apparatus for liquefying or solidifying gases or gaseous mixtures
- F25J1/0002—Processes or apparatus for liquefying or solidifying gases or gaseous mixtures characterised by the fluid to be liquefied
- F25J1/0022—Hydrocarbons, e.g. natural gas
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F25—REFRIGERATION OR COOLING; COMBINED HEATING AND REFRIGERATION SYSTEMS; HEAT PUMP SYSTEMS; MANUFACTURE OR STORAGE OF ICE; LIQUEFACTION SOLIDIFICATION OF GASES
- F25J—LIQUEFACTION, SOLIDIFICATION OR SEPARATION OF GASES OR GASEOUS OR LIQUEFIED GASEOUS MIXTURES BY PRESSURE AND COLD TREATMENT OR BY BRINGING THEM INTO THE SUPERCRITICAL STATE
- F25J3/00—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification
- F25J3/02—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream
- F25J3/04—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air
- F25J3/04406—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air using a dual pressure main column system
- F25J3/04412—Processes or apparatus for separating the constituents of gaseous or liquefied gaseous mixtures involving the use of liquefaction or solidification by rectification, i.e. by continuous interchange of heat and material between a vapour stream and a liquid stream for air using a dual pressure main column system in a classical double column flowsheet, i.e. with thermal coupling by a main reboiler-condenser in the bottom of low pressure respectively top of high pressure column
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Mechanical Engineering (AREA)
- Thermal Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1251021A FR2986525B1 (fr) | 2012-02-03 | 2012-02-03 | Procede de production de 2,3,3,3-tetrafluoropropene |
| FR1251021 | 2012-02-03 | ||
| CN201380007470.4A CN104093685A (zh) | 2012-02-03 | 2013-01-11 | 2,3,3,3-四氟丙烯的生产方法 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380007470.4A Division CN104093685A (zh) | 2012-02-03 | 2013-01-11 | 2,3,3,3-四氟丙烯的生产方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111517915A true CN111517915A (zh) | 2020-08-11 |
Family
ID=47628390
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010333467.3A Pending CN111517915A (zh) | 2012-02-03 | 2013-01-11 | 2,3,3,3-四氟丙烯的生产方法 |
| CN201380007470.4A Pending CN104093685A (zh) | 2012-02-03 | 2013-01-11 | 2,3,3,3-四氟丙烯的生产方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201380007470.4A Pending CN104093685A (zh) | 2012-02-03 | 2013-01-11 | 2,3,3,3-四氟丙烯的生产方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US9346723B2 (https=) |
| EP (2) | EP3263542B1 (https=) |
| JP (2) | JP6544927B2 (https=) |
| KR (1) | KR101999416B1 (https=) |
| CN (2) | CN111517915A (https=) |
| ES (2) | ES2764702T3 (https=) |
| FR (1) | FR2986525B1 (https=) |
| PL (2) | PL3263542T3 (https=) |
| WO (1) | WO2013114015A1 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3023286B1 (fr) | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
| JP5939283B2 (ja) * | 2014-07-15 | 2016-06-22 | ダイキン工業株式会社 | クロロプロペンの製造方法及び２，３，３，３−テトラフルオロプロペンの製造方法 |
| JP6300761B2 (ja) * | 2014-09-30 | 2018-03-28 | ダイキン工業株式会社 | ２，３，３，３−テトラフルオロプロペンの製造方法 |
| WO2016187507A1 (en) | 2015-05-21 | 2016-11-24 | The Chemours Company Fc, Llc | HYDROFLUORINATION OF 1233xf TO 244bb BY SbF5 |
| JP6233352B2 (ja) * | 2015-06-02 | 2017-11-22 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
| CN104987278B (zh) * | 2015-07-20 | 2016-09-28 | 山东联创互联网传媒股份有限公司 | 2,3,3,3-四氟丙烯的合成方法 |
| WO2018143271A1 (ja) * | 2017-01-31 | 2018-08-09 | ダイキン工業株式会社 | 含フッ素ハロゲン化炭化水素の製造方法 |
| FR3064627B1 (fr) | 2017-03-28 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| FR3064626B1 (fr) | 2017-03-28 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene. |
| FR3078700B1 (fr) | 2018-03-07 | 2020-07-10 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078699B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
| FR3078698B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2-chloro-3,3,3-trifluoropropene |
| PL3775091T3 (pl) | 2018-04-30 | 2023-07-31 | The Chemours Company Fc, Llc | Stabilizowane kompozycje fluoroolefinowe i sposoby ich wytwarzania, przechowywania i stosowania |
| CN119118781A (zh) * | 2018-06-06 | 2024-12-13 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| KR20220041173A (ko) * | 2019-08-22 | 2022-03-31 | 푸젠 융징 테크놀로지 컴퍼니 리미티드 | 직접 플루오르화에 의해 무기 또는 유기 화합물을 플루오르화하는 공법 |
| FR3100461B1 (fr) * | 2019-09-06 | 2021-09-03 | Arkema France | Procédé de purification d’hydrofluorocarbures |
| WO2021093029A1 (en) | 2019-11-13 | 2021-05-20 | Fujian Yongjing Technology Co., Ltd | New process for synthesis of 2,3,3,3-tetrafluoropropene (1234yf) and 2,3-dichloro-1,1,1-trifluoropropane (243db) |
| KR102478267B1 (ko) * | 2020-09-07 | 2022-12-19 | 한국과학기술연구원 | 함불소 환형 황 화합물의 연속적인 제조방법 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101454261A (zh) * | 2006-05-30 | 2009-06-10 | 阿克马法国公司 | 制造氢氟烃的方法 |
| CN101874009A (zh) * | 2007-07-25 | 2010-10-27 | 霍尼韦尔国际公司 | 生产2-氯-3,3,3-三氟丙烯(HCFC-1233xf)的改进方法 |
| CN102076643A (zh) * | 2008-06-26 | 2011-05-25 | 阿科玛股份有限公司 | 1230xa至1234yf的催化气相氟化 |
| WO2011077192A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | CATALYTIC GAS PHASE FLUORINATION OF 1233xf TO 1234yf |
| CN102216245A (zh) * | 2008-11-19 | 2011-10-12 | 阿科玛股份有限公司 | 用于制造氢氟烯烃的方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4902838A (en) | 1988-12-28 | 1990-02-20 | E. I. Du Pont De Nemours And Company | Isomerization of saturated fluorohydrocarbons |
| US5714651A (en) | 1995-12-28 | 1998-02-03 | Elf Atochem North America, Inc. | Use of polymerization inhibitor to prolong the life of a Lewis acid catalyst |
| EP0939071B1 (en) | 1998-02-26 | 2003-07-30 | Central Glass Company, Limited | Method for producing fluorinated propane |
| US8058486B2 (en) * | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| MXPA06012466A (es) | 2004-04-29 | 2007-01-31 | Honeywell Int Inc | Procesos para la sintesis de 1,3,3,3-tetrafluoropropeno y 2,3,3,3-tetrafluoropropeno. |
| ES3036520T3 (en) | 2006-01-03 | 2025-09-19 | Honeywell Int Inc | Method for producing fluorinated organic compounds |
| FR2901790A1 (fr) * | 2006-05-30 | 2007-12-07 | Arkema France | Procede de fabrication des hydrofluorocarbures |
| JP5416587B2 (ja) | 2006-10-03 | 2014-02-12 | メキシケム、アマンコ、ホールディング、ソシエダッド、アノニマ、デ、カピタル、バリアブレ | プロセス |
| CN103483140B (zh) | 2006-10-31 | 2015-09-09 | 纳幕尔杜邦公司 | 氟丙烷、卤代丙烯以及2-氯-3,3,3-三氟-1-丙烯与hf的共沸组合物和1,1,1,2,2-五氟丙烷与hf的共沸组合物的制备方法 |
| WO2009105512A1 (en) * | 2008-02-21 | 2009-08-27 | E. I. Du Pont De Nemours And Company | Processes for separation of 2,3,3,3-tetrafluoropropene from hydrogen fluoride by azeotropic distillation |
| FR2929271B1 (fr) | 2008-03-28 | 2010-04-16 | Arkema France | Procede pour la preparation du 1,2,3,3,3-pentafluoropropene- 1 |
| EP2349958A2 (en) * | 2008-10-29 | 2011-08-03 | Daikin Industries, Ltd. | Process for preparing 2,3,3,3-tetrafluoropropene |
| KR101374000B1 (ko) * | 2009-04-23 | 2014-03-12 | 다이킨 고교 가부시키가이샤 | 2,3,3,3-테트라플루오로프로펜의 제조 방법 |
| US8624067B2 (en) | 2009-04-23 | 2014-01-07 | Daikin Industries, Ltd. | Process for preparing 2-chloro-3,3,3-trifluoropropene |
| WO2011077193A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 243db to 1234yf |
-
2012
- 2012-02-03 FR FR1251021A patent/FR2986525B1/fr active Active
-
2013
- 2013-01-11 CN CN202010333467.3A patent/CN111517915A/zh active Pending
- 2013-01-11 US US14/376,190 patent/US9346723B2/en active Active
- 2013-01-11 KR KR1020147024668A patent/KR101999416B1/ko active Active
- 2013-01-11 PL PL17180420T patent/PL3263542T3/pl unknown
- 2013-01-11 PL PL13701863T patent/PL2809635T3/pl unknown
- 2013-01-11 JP JP2014555284A patent/JP6544927B2/ja active Active
- 2013-01-11 ES ES17180420T patent/ES2764702T3/es active Active
- 2013-01-11 EP EP17180420.6A patent/EP3263542B1/fr active Active
- 2013-01-11 ES ES13701863.6T patent/ES2638387T3/es active Active
- 2013-01-11 WO PCT/FR2013/050064 patent/WO2013114015A1/fr not_active Ceased
- 2013-01-11 EP EP13701863.6A patent/EP2809635B1/fr active Active
- 2013-01-11 CN CN201380007470.4A patent/CN104093685A/zh active Pending
-
2016
- 2016-04-27 US US15/139,662 patent/US9776938B2/en active Active
-
2018
- 2018-02-05 JP JP2018017851A patent/JP2018109010A/ja not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101454261A (zh) * | 2006-05-30 | 2009-06-10 | 阿克马法国公司 | 制造氢氟烃的方法 |
| CN101874009A (zh) * | 2007-07-25 | 2010-10-27 | 霍尼韦尔国际公司 | 生产2-氯-3,3,3-三氟丙烯(HCFC-1233xf)的改进方法 |
| CN102076643A (zh) * | 2008-06-26 | 2011-05-25 | 阿科玛股份有限公司 | 1230xa至1234yf的催化气相氟化 |
| CN102216245A (zh) * | 2008-11-19 | 2011-10-12 | 阿科玛股份有限公司 | 用于制造氢氟烯烃的方法 |
| WO2011077192A1 (en) * | 2009-12-23 | 2011-06-30 | Arkema France | CATALYTIC GAS PHASE FLUORINATION OF 1233xf TO 1234yf |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2809635A1 (fr) | 2014-12-10 |
| US9776938B2 (en) | 2017-10-03 |
| KR20140117682A (ko) | 2014-10-07 |
| US20160237009A1 (en) | 2016-08-18 |
| WO2013114015A1 (fr) | 2013-08-08 |
| CN104093685A (zh) | 2014-10-08 |
| KR101999416B1 (ko) | 2019-07-11 |
| JP6544927B2 (ja) | 2019-07-17 |
| ES2638387T3 (es) | 2017-10-20 |
| PL3263542T3 (pl) | 2020-03-31 |
| JP2015511230A (ja) | 2015-04-16 |
| EP2809635B1 (fr) | 2017-07-26 |
| JP2018109010A (ja) | 2018-07-12 |
| FR2986525B1 (fr) | 2014-02-14 |
| US20150080619A1 (en) | 2015-03-19 |
| FR2986525A1 (fr) | 2013-08-09 |
| EP3263542A1 (fr) | 2018-01-03 |
| EP3263542B1 (fr) | 2019-11-13 |
| US9346723B2 (en) | 2016-05-24 |
| PL2809635T3 (pl) | 2018-01-31 |
| ES2764702T3 (es) | 2020-06-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN111517915A (zh) | 2,3,3,3-四氟丙烯的生产方法 | |
| US10329227B2 (en) | Process for the preparation of 2,3,3,3-tetrafluoropropene | |
| US9828315B2 (en) | Process for the manufacture of 2,3,3,3-tetrafluoropropene by gas phase fluorination of pentachloropropane | |
| JP6677658B2 (ja) | テトラフルオロプロペンの製造方法 | |
| US9388099B2 (en) | Process for producing 2,3,3,3-tetrafluoropropene | |
| US9284240B2 (en) | Process for the manufacture of 2-chloro-3,3,3-trifluoropropene by gas phase fluorination of pentachloropropane | |
| KR101928224B1 (ko) | 클로로프로펜의 제조 방법 및 2,3,3,3-테트라플루오로프로펜의 제조 방법 | |
| WO2017119273A1 (ja) | ２，３，３，３－テトラフルオロプロペンの製造方法 | |
| JP5020968B2 (ja) | ジクロロトリフルオロエタンの製造方法 | |
| JP2009519923A (ja) | ジクロロトリフルオロエタンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20200811 |