JP6688383B2 - 2,3,3,3−テトラフルオロプロペン(1234yf)の調製プロセス - Google Patents
2,3,3,3−テトラフルオロプロペン(1234yf)の調製プロセス Download PDFInfo
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- JP6688383B2 JP6688383B2 JP2018502143A JP2018502143A JP6688383B2 JP 6688383 B2 JP6688383 B2 JP 6688383B2 JP 2018502143 A JP2018502143 A JP 2018502143A JP 2018502143 A JP2018502143 A JP 2018502143A JP 6688383 B2 JP6688383 B2 JP 6688383B2
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- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 title claims description 45
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 239000003054 catalyst Substances 0.000 claims description 91
- 238000000034 method Methods 0.000 claims description 44
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 39
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 34
- 229910052725 zinc Inorganic materials 0.000 claims description 34
- 239000011701 zinc Substances 0.000 claims description 34
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 33
- QDOXWKRWXJOMAK-UHFFFAOYSA-N dichromium trioxide Chemical compound O=[Cr]O[Cr]=O QDOXWKRWXJOMAK-UHFFFAOYSA-N 0.000 claims description 32
- 238000000746 purification Methods 0.000 claims description 31
- 238000004821 distillation Methods 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 26
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 25
- 238000005201 scrubbing Methods 0.000 claims description 24
- 239000011651 chromium Substances 0.000 claims description 23
- 238000005796 dehydrofluorination reaction Methods 0.000 claims description 21
- 229910052804 chromium Inorganic materials 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 15
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 15
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 14
- 238000003682 fluorination reaction Methods 0.000 claims description 14
- 238000001035 drying Methods 0.000 claims description 9
- 238000005191 phase separation Methods 0.000 claims description 6
- 238000004064 recycling Methods 0.000 claims description 5
- 230000003197 catalytic effect Effects 0.000 claims description 4
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- FDOPVENYMZRARC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropropane Chemical compound CC(F)(F)C(F)(F)F FDOPVENYMZRARC-UHFFFAOYSA-N 0.000 claims description 3
- 239000012808 vapor phase Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 description 40
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
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- 238000000926 separation method Methods 0.000 description 8
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 238000002441 X-ray diffraction Methods 0.000 description 4
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- 229910052719 titanium Inorganic materials 0.000 description 4
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- 150000003752 zinc compounds Chemical class 0.000 description 4
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
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- 229910052742 iron Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
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- 238000001179 sorption measurement Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052715 tantalum Inorganic materials 0.000 description 3
- 229910052718 tin Inorganic materials 0.000 description 3
- 229910000314 transition metal oxide Inorganic materials 0.000 description 3
- 229910052726 zirconium Inorganic materials 0.000 description 3
- ZPIFKCVYZBVZIV-UHFFFAOYSA-N 3-chloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)CCCl ZPIFKCVYZBVZIV-UHFFFAOYSA-N 0.000 description 2
- 229910016569 AlF 3 Inorganic materials 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
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- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910000423 chromium oxide Inorganic materials 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000010421 standard material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- UTACNSITJSJFHA-UHFFFAOYSA-N 1,1,1,3-tetrachloropropane Chemical compound ClCCC(Cl)(Cl)Cl UTACNSITJSJFHA-UHFFFAOYSA-N 0.000 description 1
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- VKEIPALYOJMDAC-UHFFFAOYSA-N 3,3,3-trichloroprop-1-ene Chemical compound ClC(Cl)(Cl)C=C VKEIPALYOJMDAC-UHFFFAOYSA-N 0.000 description 1
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical group FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 description 1
- KDWQLICBSFIDRM-UHFFFAOYSA-N CCC(F)(F)F Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 1
- 235000013162 Cocos nucifera Nutrition 0.000 description 1
- 244000060011 Cocos nucifera Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003575 carbonaceous material Substances 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
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- 239000007805 chemical reaction reactant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 description 1
- BSKAIKMQTLKUOW-UHFFFAOYSA-N chromium;fluoro hypofluorite Chemical class [Cr].FOF BSKAIKMQTLKUOW-UHFFFAOYSA-N 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
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- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
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- 238000005516 engineering process Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000856 hastalloy Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
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- 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
- C07C17/357—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by dehydrogenation
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- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
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- B01J23/16—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
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- C07C17/00—Preparation of halogenated hydrocarbons
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/02—Materials undergoing a change of physical state when used
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- C09K5/044—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds
- C09K5/045—Materials undergoing a change of physical state when used the change of state being from liquid to vapour or vice versa for compression-type refrigeration systems comprising halogenated compounds containing only fluorine as halogen
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- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
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- 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
- Y02P20/10—Process efficiency
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- 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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- 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
Description
(a)フッ素化反応器中で3,3,3−トリフルオロ−2−クロロ−プロパ−1−エン(CF3CCl=CH2、1233xf)を含む第1の組成物をフッ化水素(HF)で気相触媒フッ素化して、1,1,1,2,2−ペンタフルオロプロパン(245cb)、HF及びHClを含むフッ素化生成物流を生成することと、
(b)脱フッ化水素化反応器中で245cbを含む第2の組成物を気相触媒脱フッ化水素化して、1234yf及びHFを含む脱フッ化水素化生成物流を生成することと、
ここで、フッ素化生成物流及び脱フッ化水素化生成物流を合わせ、(c)精製を施して、245cb及び1234yfの生成物流を含む組成物を生成することとを含む。
Cr2O3+2HF→2CrOF+H2O
CF3CHClCH2Cl→CF3CCl=CH2
Claims (20)
- 2,3,3,3−テトラフルオロプロペン(1234yf)を調製するための統合されたプロセスであって、
(a)フッ素化反応器中で3,3,3−トリフルオロ−2−クロロ−プロパ−1−エン(CF3CCl=CH2、1233xf)を含む第1の組成物をフッ化水素(HF)で気相触媒フッ素化して、1,1,1,2,2−ペンタフルオロプロパン(245cb)、HF、及びHClを含むフッ素化生成物流を生成することと、
(b)脱フッ化水素化反応器中で245cbを含む第2の組成物を気相触媒脱フッ化水素化して、1234yf及びHFを含む脱フッ化水素化生成物流を生成することと、
前記フッ素化生成物流と前記脱フッ化水素化生成物流を合流させ、(c)精製を施して、245cb及び1234yfの生成物流を含む組成物を生成することと、を含み、前記精製工程(c)が、蒸留工程を含み、ここで、245cb、1234yf、任意の1234ze(E)、及び一部のHFを含む、軽質留分が蒸留されて、HFの大部分及び未反応1233xfを含む、重質留分を残し、前記軽質留分が、蒸留塔から取り出され、スクラビングトレインに通される、プロセス。 - 245cb及び1234yfの生成物流を含む前記組成物が、前記第2の組成物として前記脱フッ化水素化反応器に供給される、請求項1に記載のプロセス。
- 前記1234yfの少なくとも一部が、245cb及び1234yfの生成物流を含む前記組成物から除去され、前記得られた組成物が、前記第2の組成物として前記脱フッ化水素化反応器に供給される、請求項1に記載のプロセス。
- 前記1234yfの少なくとも一部が除去された後、前記得られた組成物が、精製工程を施され、ここで、前記組成物中に存在し得る任意の1234zeの少なくとも一部が、低減された1234yf濃度を有する前記組成物が前記第2の組成物として前記脱フッ化水素化反応器に供給される前に除去される、請求項3に記載のプロセス。
- 前記精製工程(c)が、1つ以上の相分離工程を含む、請求項1〜4のいずれかに記載のプロセス。
- 前記精製工程(c)における前記スクラビングトレインが、順番に、バルク酸除去工程、微量の酸除去工程、及び1つ以上の乾燥工程を含む、請求項1〜5のいずれか1項に記載のプロセス。
- HFが、少なくとも1つの蒸留塔から回収され、任意に反応(a)での使用のためにリサイクルされる、請求項1〜6のいずれか1項に記載のプロセス。
- 前記HFが、リサイクルする前に、さらなる精製を施される、請求項7に記載のプロセス。
- 前記HFが、相分離によって精製される、請求項8に記載のプロセス。
- 前記プロセスが、243dbの脱塩化水素化によって、反応(a)で使用される前記1233xfを得る工程を含む、請求項1〜9のいずれか1項に記載のプロセス。
- 前記脱塩化水素化反応が、HFの存在下及び/または空気の非存在下で行われる、請求項10に記載のプロセス。
- 前記脱塩化水素化反応が、亜鉛/クロミア触媒の存在下で行われる、請求項10または11に記載のプロセス。
- 前記脱塩化水素化反応が、HFの存在下で行われ、前記HFの少なくとも一部が、工程(c)からリサイクルされる、請求項10〜12のいずれか1項に記載のプロセス。
- 反応(a)が、空気の存在下で行われる、請求項1〜13のいずれか1項に記載のプロセス。
- 前記フッ素化生成物流は、この生成物流が前記脱フッ化水素化生成物流と合流される前に、精製工程を施されて、前記HClの少なくとも一部及び前記空気の少なくとも一部を除去する、請求項14に記載のプロセス。
- 蒸留が、前記HClの少なくとも一部及び前記空気の少なくとも一部を除去するために使用される、請求項15に記載のプロセス。
- 反応(a)が、亜鉛/クロミア触媒の存在下で行われる、請求項1〜16のいずれか1項に記載のプロセス。
- 反応(b)が、アルミナまたは亜鉛/クロミア触媒上のクロムの存在下で行われる、請求項1〜17のいずれか1項に記載のプロセス。
- 反応(a)が、200〜300℃の温度及び500〜1500KPaの圧力で行われる、請求項1〜18のいずれか1項に記載のプロセス。
- 反応(b)が、300〜500℃の温度及び/または0〜1500kPaの圧力で行われる、請求項1〜19のいずれか1項に記載のプロセス。
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GB1512593.3A GB2540427B (en) | 2015-07-17 | 2015-07-17 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
GB1512593.3 | 2015-07-17 | ||
PCT/GB2016/052145 WO2017013406A1 (en) | 2015-07-17 | 2016-07-14 | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
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ES2864023T3 (es) | 2021-10-13 |
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US20200165179A1 (en) | 2020-05-28 |
CN107848916A (zh) | 2018-03-27 |
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JP2018524376A (ja) | 2018-08-30 |
GB2540427A (en) | 2017-01-18 |
US10899686B2 (en) | 2021-01-26 |
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