JP4399194B2 - フッ化アシルの製造方法 - Google Patents
フッ化アシルの製造方法 Download PDFInfo
- Publication number
- JP4399194B2 JP4399194B2 JP2003178437A JP2003178437A JP4399194B2 JP 4399194 B2 JP4399194 B2 JP 4399194B2 JP 2003178437 A JP2003178437 A JP 2003178437A JP 2003178437 A JP2003178437 A JP 2003178437A JP 4399194 B2 JP4399194 B2 JP 4399194B2
- Authority
- JP
- Japan
- Prior art keywords
- catalyst
- compound
- fluoride
- cof
- acyl fluoride
- 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.)
- Expired - Fee Related
Links
- 150000001265 acyl fluorides Chemical class 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000003054 catalyst Substances 0.000 claims description 43
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 23
- 150000002222 fluorine compounds Chemical class 0.000 claims description 6
- 239000011261 inert gas Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 3
- 238000010924 continuous production Methods 0.000 claims description 3
- SYNPRNNJJLRHTI-UHFFFAOYSA-N 2-(hydroxymethyl)butane-1,4-diol Chemical compound OCCC(CO)CO SYNPRNNJJLRHTI-UHFFFAOYSA-N 0.000 claims description 2
- 229920001774 Perfluoroether Polymers 0.000 claims description 2
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- IBBSHLLCYYCDGD-UHFFFAOYSA-N helium mercury Chemical compound [He].[Hg] IBBSHLLCYYCDGD-UHFFFAOYSA-N 0.000 claims description 2
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical compound FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 claims description 2
- 239000011148 porous material Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 claims description 2
- 239000007792 gaseous phase Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 9
- -1 hydrogenated alkylcarbonyl compound Chemical class 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229910001512 metal fluoride Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000001944 continuous distillation Methods 0.000 description 2
- 238000000806 fluorine-19 nuclear magnetic resonance spectrum Methods 0.000 description 2
- IYRWEQXVUNLMAY-UHFFFAOYSA-N fluoroketone group Chemical group FC(=O)F IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 2
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 2
- 229960002050 hydrofluoric acid Drugs 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical compound FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- GAKSVIQMUADMSK-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(trifluoromethoxy)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)OC(F)(F)F GAKSVIQMUADMSK-UHFFFAOYSA-N 0.000 description 1
- BRWSHOSLZPMKII-UHFFFAOYSA-N 2,3,3,3-tetrafluoro-2-(trifluoromethyl)propanoyl fluoride Chemical compound FC(=O)C(F)(C(F)(F)F)C(F)(F)F BRWSHOSLZPMKII-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- 229910004261 CaF 2 Inorganic materials 0.000 description 1
- LVWJKQYIOHTDNX-UHFFFAOYSA-N FC(F)(F)OC(=C(F)F)OC(F)(F)F Chemical group FC(F)(F)OC(=C(F)F)OC(F)(F)F LVWJKQYIOHTDNX-UHFFFAOYSA-N 0.000 description 1
- AHSFRJBERJUGJC-UHFFFAOYSA-N O(F)F.[Na] Chemical compound O(F)F.[Na] AHSFRJBERJUGJC-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000004673 fluoride salts Chemical class 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000008187 granular material Substances 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
- 229910052742 iron Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/58—Preparation of carboxylic acid halides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2002MI001365A ITMI20021365A1 (it) | 2002-06-21 | 2002-06-21 | Processo per preparare acilfluoruri |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004043465A JP2004043465A (ja) | 2004-02-12 |
| JP2004043465A5 JP2004043465A5 (enExample) | 2006-04-20 |
| JP4399194B2 true JP4399194B2 (ja) | 2010-01-13 |
Family
ID=11450056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003178437A Expired - Fee Related JP4399194B2 (ja) | 2002-06-21 | 2003-06-23 | フッ化アシルの製造方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6852884B2 (enExample) |
| EP (1) | EP1375469B1 (enExample) |
| JP (1) | JP4399194B2 (enExample) |
| DE (1) | DE60315761T2 (enExample) |
| IT (1) | ITMI20021365A1 (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ITMI20030606A1 (it) | 2003-03-27 | 2004-09-28 | Solvay Solexis Spa | Procedimento per preparare idrofluoroeteri. |
| JP4760079B2 (ja) * | 2005-03-24 | 2011-08-31 | 旭硝子株式会社 | 新規な含フッ素化合物および含フッ素重合体 |
| EP1803702A1 (de) * | 2005-12-30 | 2007-07-04 | Solvay Fluor GmbH | Drucklose Anlagerung von Acylfluoriden an Perfluoralkene |
| JP5995567B2 (ja) * | 2012-07-12 | 2016-09-21 | キヤノン株式会社 | インプリント装置、それを用いた物品の製造方法 |
| CN106748740A (zh) * | 2016-11-22 | 2017-05-31 | 天津市长芦化工新材料有限公司 | 一种制备全氟丙酰氟的方法 |
| CN106946669B (zh) * | 2017-03-21 | 2020-09-15 | 国家电网公司 | 一种环保绝缘气体联产工艺及工业化生产装置 |
| CN107935884B (zh) * | 2017-11-30 | 2020-06-12 | 北京宇极科技发展有限公司 | 全氟腈的制备方法 |
| CN108424375B (zh) * | 2018-04-20 | 2020-06-02 | 北京宇极科技发展有限公司 | 全氟腈的制备方法 |
| CN108314614B (zh) * | 2018-04-20 | 2021-03-12 | 北京宇极科技发展有限公司 | 气相制备五氟乙基全氟异丙基酮的方法 |
| CN109535001B (zh) * | 2018-11-20 | 2022-07-05 | 昊华气体有限公司 | 一种制备氟代羧酸酯的方法 |
| CN110734373B (zh) * | 2019-06-30 | 2022-07-05 | 天津市长芦化工新材料有限公司 | 反应釜液相法制备全氟异丁酰氟的方法 |
| CN121005618A (zh) * | 2025-10-28 | 2025-11-25 | 山东齐氟新材料有限公司 | 七氟异丁酰氟的连续生产工艺 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3114778A (en) | 1963-12-17 | Fluorinated vinyl ethers and their | ||
| US3113967A (en) * | 1960-10-25 | 1963-12-10 | Du Pont | Addition of carbonyl fluoride to polyfluoro-olefins |
| US3758538A (en) * | 1965-10-01 | 1973-09-11 | Allied Chem | (CF{11 ){11 {11 CFO{116 Ag{115 |
| US4769184A (en) * | 1987-09-08 | 1988-09-06 | Nippon Mektron Limited | Process for producing carbonyl fluoride compound |
| US6013795A (en) | 1996-11-04 | 2000-01-11 | 3M Innovative Properties Company | Alpha-branched fluoroalkylcarbonyl fluorides and their derivatives |
-
2002
- 2002-06-21 IT IT2002MI001365A patent/ITMI20021365A1/it unknown
-
2003
- 2003-06-11 EP EP03013110A patent/EP1375469B1/en not_active Expired - Lifetime
- 2003-06-11 DE DE60315761T patent/DE60315761T2/de not_active Expired - Lifetime
- 2003-06-16 US US10/461,349 patent/US6852884B2/en not_active Expired - Lifetime
- 2003-06-23 JP JP2003178437A patent/JP4399194B2/ja not_active Expired - Fee Related
-
2004
- 2004-12-03 US US11/002,463 patent/US6998506B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1375469B1 (en) | 2007-08-22 |
| US20050080291A1 (en) | 2005-04-14 |
| ITMI20021365A0 (it) | 2002-06-21 |
| US6852884B2 (en) | 2005-02-08 |
| US20030236436A1 (en) | 2003-12-25 |
| EP1375469A1 (en) | 2004-01-02 |
| DE60315761D1 (de) | 2007-10-04 |
| JP2004043465A (ja) | 2004-02-12 |
| ITMI20021365A1 (it) | 2003-12-22 |
| US6998506B2 (en) | 2006-02-14 |
| DE60315761T2 (de) | 2008-06-05 |
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