JP5329637B2 - ジフルオロ酢酸およびこの塩の調製方法 - Google Patents
ジフルオロ酢酸およびこの塩の調製方法 Download PDFInfo
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- JP5329637B2 JP5329637B2 JP2011500150A JP2011500150A JP5329637B2 JP 5329637 B2 JP5329637 B2 JP 5329637B2 JP 2011500150 A JP2011500150 A JP 2011500150A JP 2011500150 A JP2011500150 A JP 2011500150A JP 5329637 B2 JP5329637 B2 JP 5329637B2
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- catalyst
- chromium
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- fluoride
- hydrofluoric acid
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- 238000000034 method Methods 0.000 title claims abstract description 45
- PBWZKZYHONABLN-UHFFFAOYSA-N difluoroacetic acid Chemical compound OC(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000003839 salts Chemical class 0.000 title abstract description 5
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 34
- CRLSHTZUJTXOEL-UHFFFAOYSA-N 2,2-difluoroacetyl fluoride Chemical compound FC(F)C(F)=O CRLSHTZUJTXOEL-UHFFFAOYSA-N 0.000 claims abstract description 24
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 claims abstract description 20
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052804 chromium Inorganic materials 0.000 claims abstract description 15
- 239000011651 chromium Substances 0.000 claims abstract description 15
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 16
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 14
- 238000003682 fluorination reaction Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 239000000758 substrate Substances 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 4
- 239000011777 magnesium Substances 0.000 claims description 4
- 229910052751 metal Inorganic materials 0.000 claims description 4
- 239000002184 metal Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 239000010941 cobalt Substances 0.000 claims description 3
- 229910017052 cobalt Inorganic materials 0.000 claims description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 229910021563 chromium fluoride Inorganic materials 0.000 claims description 2
- QCMJBECJXQJLIL-UHFFFAOYSA-L chromium(6+);oxygen(2-);difluoride Chemical compound [O-2].[O-2].[F-].[F-].[Cr+6] QCMJBECJXQJLIL-UHFFFAOYSA-L 0.000 claims description 2
- PBWZKZYHONABLN-UHFFFAOYSA-M difluoroacetate Chemical group [O-]C(=O)C(F)F PBWZKZYHONABLN-UHFFFAOYSA-M 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 239000011949 solid catalyst Substances 0.000 claims description 2
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- -1 hydrofluoric acid di chloroacetyl chloride Chemical compound 0.000 claims 1
- 239000007792 gaseous phase Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000007789 gas Substances 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- 239000012071 phase Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 150000001844 chromium Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- OAWAZQITIZDJRB-UHFFFAOYSA-N 2-chloro-2,2-difluoroacetic acid Chemical compound OC(=O)C(F)(F)Cl OAWAZQITIZDJRB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229910000856 hastalloy Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000011324 bead Substances 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- PHFQLYPOURZARY-UHFFFAOYSA-N chromium trinitrate Chemical compound [Cr+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O PHFQLYPOURZARY-UHFFFAOYSA-N 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010304 firing Methods 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 150000002823 nitrates Chemical class 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- VUYQBMXVCZBVHP-UHFFFAOYSA-N 1,1-difluoroethanol Chemical compound CC(O)(F)F VUYQBMXVCZBVHP-UHFFFAOYSA-N 0.000 description 1
- JVYROUWXXSWCMI-UHFFFAOYSA-N 2-bromo-1,1-difluoroethane Chemical compound FC(F)CBr JVYROUWXXSWCMI-UHFFFAOYSA-N 0.000 description 1
- JCRDJKCRGITHDO-UHFFFAOYSA-N 2-chloro-n,n-diethyl-2-fluoroacetamide Chemical compound CCN(CC)C(=O)C(F)Cl JCRDJKCRGITHDO-UHFFFAOYSA-N 0.000 description 1
- PMJNEQWWZRSFCE-UHFFFAOYSA-N 3-ethoxy-3-oxo-2-(thiophen-2-ylmethyl)propanoic acid Chemical compound CCOC(=O)C(C(O)=O)CC1=CC=CS1 PMJNEQWWZRSFCE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HXELGNKCCDGMMN-UHFFFAOYSA-N [F].[Cl] Chemical group [F].[Cl] HXELGNKCCDGMMN-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- UBFMILMLANTYEU-UHFFFAOYSA-H chromium(3+);oxalate Chemical compound [Cr+3].[Cr+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O UBFMILMLANTYEU-UHFFFAOYSA-H 0.000 description 1
- UOUJSJZBMCDAEU-UHFFFAOYSA-N chromium(3+);oxygen(2-) Chemical class [O-2].[O-2].[O-2].[Cr+3].[Cr+3] UOUJSJZBMCDAEU-UHFFFAOYSA-N 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- JXTHNDFMNIQAHM-UHFFFAOYSA-N dichloroacetic acid Chemical class OC(=O)C(Cl)Cl JXTHNDFMNIQAHM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical group [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 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
- C07C51/04—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid halides
-
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Description
DCAC:ジクロロアセチルクロリド
DFAF:ジフルオロアセチルフルオリド
以下の実施例は、温度、HF/DCAC比、および滞留時間の影響を示している。
Claims (19)
- ジクロロアセチルクロリドとフッ化水素酸とを、気相中、クロム系触媒存在下で反応させることによって、ジフルオロアセチルフルオリドを調製するステップと、続いて、得られたジフルオロアセチルフルオリドを加水分解するステップとを含むことを特徴とする、ジフルオロ酢酸の調製方法。
- フッ素化触媒が、金属元素でドープされた、クロムの酸化物、ハロゲン化物、オキシハロゲン化物、または無機塩を含むことを特徴とする、請求項1に記載の方法。
- 金属元素が、ニッケル、コバルト、マグネシウム、または亜鉛である請求項2に記載の方法。
- フッ素化触媒が、酸化クロム、フッ化クロム、もしくはオキシフッ化クロム、または金属元素でドープされたクロムを含むことを特徴とする、請求項2に記載の方法。
- 触媒に対して、熱処理および/またはフッ素化処理による活性化が行われ、活性化がフッ素化中に行われることを特徴とする、請求項1から4の一項に記載の方法。
- 触媒が、フッ素化処理による活性化が行われている酸化クロムIIIであることを特徴とする、請求項1から5の一項に記載の方法。
- 活性相が、微粉砕された形態であるか、または、担体上に形成または堆積されるかであることを特徴とする、請求項1から6の一項に記載の方法。
- 触媒重量の0.5%から5%の比率でクロムが担体上に堆積されることを特徴とする、請求項7に記載の方法。
- フッ化水素酸のモル数とジクロロアセチルクロリドのモル数との間の比が1から30の間であることを特徴とする、請求項1から8の一項に記載の方法。
- 反応温度が250℃から400℃の間であることを特徴とする、請求項1から9の一項に記載の方法。
- バッチ方式または連続方式で行われることを特徴とする、請求項1から10の一項に記載の方法。
- 反応が連続方式で、固定床に配置された固体触媒を含む管型反応器中で行われることを特徴とする、請求項1から11の一項に記載の方法。
- ジクロロアセチルクロリドとフッ化水素酸とを混合ゾーン中で互いに混合し、次に、得られた混合物を触媒床に移動させることを特徴とする、請求項1から12の一項に記載の方法。
- 触媒の見掛けの体積とガス流の流量との間の比として定義される接触時間が0.2から100秒の間の範囲であることを特徴とする、請求項1から13の一項に記載の方法。
- 触媒の単位重量当たり1時間当たりに使用される基質の重量が0.01h−1から2h−1の間の範囲であることを特徴とする、請求項1から14の一項に記載の方法。
- 反応終了時に、ジフルオロアセチルフルオリドと、過剰のフッ化水素酸と、反応によって形成された塩酸とを含む気相を回収することを特徴とする、請求項1から15の一項に記載の方法。
- 次に、ガス流を水と接触するように配置することによって、ジフルオロアセチルフルオリドを加水分解してジフルオロ酢酸を得るステップが行われることを特徴とする、請求項1から16の一項に記載の方法。
- 得られたジフルオロ酢酸を塩基と反応させることを特徴とする、請求項1から17の一項に記載の方法。
- ジクロロアセチルクロリドとフッ化水素酸とを、気相中、クロム系触媒の存在下で反応させることによって、ジフルオロアセチルフルオリドが得られることを特徴とする、ジフルオロアセチルフルオリドの調製方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR0801513A FR2928919B1 (fr) | 2008-03-19 | 2008-03-19 | Procede de preparation de l'acide difluoroacetique et de ses sels |
FR0801513 | 2008-03-19 | ||
PCT/EP2009/052740 WO2009115426A1 (fr) | 2008-03-19 | 2009-03-09 | Procede de preparation de l'acide difluoroacetique et de ses sels |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2011515354A JP2011515354A (ja) | 2011-05-19 |
JP5329637B2 true JP5329637B2 (ja) | 2013-10-30 |
Family
ID=40043991
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2011500150A Expired - Fee Related JP5329637B2 (ja) | 2008-03-19 | 2009-03-09 | ジフルオロ酢酸およびこの塩の調製方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US8299300B2 (ja) |
EP (1) | EP2268601B1 (ja) |
JP (1) | JP5329637B2 (ja) |
CN (1) | CN101977885A (ja) |
FR (1) | FR2928919B1 (ja) |
RU (1) | RU2467997C2 (ja) |
WO (1) | WO2009115426A1 (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8716526B2 (en) | 2010-03-29 | 2014-05-06 | Central Glass Company, Limited | Method for producing difluoroacetyl chloride |
CN102093195A (zh) * | 2011-01-29 | 2011-06-15 | 锦州惠发天合化学有限公司 | 一种氟代酸的制备方法 |
CN103420836A (zh) * | 2012-05-21 | 2013-12-04 | 上海品沃化工有限公司 | 含氟低碳脂肪酸的提纯方法 |
FR2999177A1 (fr) * | 2012-12-10 | 2014-06-13 | Rhodia Operations | Procede de fluoration et agent de fluoration |
EP2810931B1 (en) * | 2013-06-06 | 2018-04-25 | Solvay SA | Process for the preparation of halogenated carboxylic anhydrides |
CN106748747B (zh) * | 2016-11-18 | 2020-04-07 | 江西省汉氏贵金属有限公司 | 三氟乙酸钯的制备方法 |
CN109534987B (zh) * | 2018-12-30 | 2022-02-15 | 山东华安新材料有限公司 | 一种二氟乙酸的制备方法 |
US20220402850A1 (en) * | 2020-01-22 | 2022-12-22 | Kanto Denka Kogyo Co., Ltd. | Method of purifying carboxylic acid fluoride |
CN111995516B (zh) * | 2020-09-03 | 2023-08-04 | 科莱博(江苏)科技股份有限公司 | 一种二氟乙酰氟的合成方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB976316A (en) * | 1962-07-31 | 1964-11-25 | Du Pont | Process for preparing fluorinated perhalo compounds |
SU290697A1 (ru) * | 1969-09-22 | 1975-12-05 | Способ получени дифторацетонитрила | |
FR2501062A1 (fr) * | 1980-12-29 | 1982-09-10 | Ugine Kuhlmann | Catalyseurs de fluoruration en phase gazeuse de derives chlores aliphatiques, a base de microbilles d'oxyde de chrome, et procedes de fluoruration utilisant ces catalyseurs |
JPH06228043A (ja) * | 1993-02-05 | 1994-08-16 | Asahi Glass Co Ltd | ジフルオロ酢酸の製造方法 |
DE4342187A1 (de) * | 1993-12-10 | 1995-06-14 | Bayer Ag | Verfahren zur Herstellung von aliphatischen omega-Difluorcarboxylverbindungen |
JPH07242587A (ja) * | 1994-03-04 | 1995-09-19 | Asahi Glass Co Ltd | ジフルオロ酢酸およびジフルオロ酢酸アミドの製造方法 |
JPH0853388A (ja) * | 1994-06-08 | 1996-02-27 | Asahi Glass Co Ltd | ジフルオロ酢酸ハライドおよびジフルオロ酢酸の製造方法 |
DE4423386A1 (de) * | 1994-07-04 | 1996-01-18 | Hoechst Ag | Verfahren zur Herstellung von Trifluoracetylfluorid |
JP3632243B2 (ja) * | 1994-07-28 | 2005-03-23 | 旭硝子株式会社 | ジフルオロ酢酸フルオリドおよびジフルオロ酢酸エステルの製造方法 |
US5905169A (en) * | 1995-03-20 | 1999-05-18 | E. I. Du Pont De Nemours And Company | Process for producing polyfluoroacyl compositions |
IT1298091B1 (it) * | 1998-01-09 | 1999-12-20 | Ausimont Spa | Processo per la preparazione degli alogenuri di diclorofluoroacetile |
FR2787107B1 (fr) | 1998-12-11 | 2003-11-14 | Rhodia Chimie Sa | Procede d'hydrogenodeshalogenation selective |
GB0329314D0 (en) * | 2003-12-18 | 2004-01-21 | Pfizer Ltd | Substituted arylpyrazoles |
JP2005336164A (ja) * | 2004-04-26 | 2005-12-08 | Showa Denko Kk | 1,1−ジクロロエタンの精製方法およびその方法を用いる1,1−ジフルオロエタンの製造方法 |
JP5013692B2 (ja) * | 2004-09-16 | 2012-08-29 | 昭和電工株式会社 | フルオロメタンの製造方法およびその製品 |
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EP2268601A1 (fr) | 2011-01-05 |
US8299300B2 (en) | 2012-10-30 |
WO2009115426A1 (fr) | 2009-09-24 |
RU2010142466A (ru) | 2012-04-27 |
EP2268601B1 (fr) | 2014-09-17 |
FR2928919A1 (fr) | 2009-09-25 |
CN101977885A (zh) | 2011-02-16 |
RU2467997C2 (ru) | 2012-11-27 |
US20110065955A1 (en) | 2011-03-17 |
JP2011515354A (ja) | 2011-05-19 |
FR2928919B1 (fr) | 2011-07-29 |
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