JP2014532046A - 2,3,3,3−テトラフルオロプロペンの製造方法 - Google Patents
2,3,3,3−テトラフルオロプロペンの製造方法 Download PDFInfo
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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 23
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 52
- 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 abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 25
- 238000003682 fluorination reaction Methods 0.000 claims abstract description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000001301 oxygen Substances 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052801 chlorine Chemical group 0.000 claims abstract description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 9
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 9
- YVWGMAFXEJHFRO-UHFFFAOYSA-N halopropane Chemical compound FC(F)C(F)(F)CBr YVWGMAFXEJHFRO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229950000188 halopropane Drugs 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 8
- 239000007789 gas Substances 0.000 claims abstract description 7
- 230000004913 activation Effects 0.000 claims description 23
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical group [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000007800 oxidant agent Substances 0.000 claims description 13
- 239000011651 chromium Substances 0.000 claims description 10
- 239000011777 magnesium Substances 0.000 claims description 9
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical group [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052804 chromium Inorganic materials 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 229910052759 nickel Inorganic materials 0.000 claims description 8
- 150000002894 organic compounds Chemical class 0.000 claims description 8
- 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 6
- ZXPCCXXSNUIVNK-UHFFFAOYSA-N 1,1,1,2,3-pentachloropropane Chemical compound ClCC(Cl)C(Cl)(Cl)Cl ZXPCCXXSNUIVNK-UHFFFAOYSA-N 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000011701 zinc Substances 0.000 claims description 6
- QJMGASHUZRHZBT-UHFFFAOYSA-N 2,3-dichloro-1,1,1-trifluoropropane Chemical group FC(F)(F)C(Cl)CCl QJMGASHUZRHZBT-UHFFFAOYSA-N 0.000 claims description 5
- 229910052725 zinc Inorganic materials 0.000 claims description 5
- 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 claims 1
- PGJHURKAWUJHLJ-UHFFFAOYSA-N 1,1,2,3-tetrafluoroprop-1-ene Chemical compound FCC(F)=C(F)F PGJHURKAWUJHLJ-UHFFFAOYSA-N 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 18
- 239000003570 air Substances 0.000 description 12
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 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 5
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000001590 oxidative effect Effects 0.000 description 4
- FTCVHAQNWWBTIV-UHFFFAOYSA-N 1,1,1,2,2-pentachloropropane Chemical compound CC(Cl)(Cl)C(Cl)(Cl)Cl FTCVHAQNWWBTIV-UHFFFAOYSA-N 0.000 description 3
- ZDCWZRQSHBQRGN-UHFFFAOYSA-N 1,1,1,2,3-pentafluoropropane Chemical compound FCC(F)C(F)(F)F ZDCWZRQSHBQRGN-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001844 chromium Chemical class 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 150000002815 nickel Chemical class 0.000 description 3
- -1 or oxide derivatives Chemical class 0.000 description 3
- 150000003751 zinc Chemical class 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 238000005470 impregnation Methods 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- DMUPYMORYHFFCT-UPHRSURJSA-N (z)-1,2,3,3,3-pentafluoroprop-1-ene Chemical compound F\C=C(/F)C(F)(F)F DMUPYMORYHFFCT-UPHRSURJSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical group FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- LDTMPQQAWUMPKS-UHFFFAOYSA-N 1-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=CCl LDTMPQQAWUMPKS-UHFFFAOYSA-N 0.000 description 1
- 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 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 229910016569 AlF 3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- HTEUDFUQTORZIN-UHFFFAOYSA-N FC(C(=C)Cl)(F)F.[F] Chemical group FC(C(=C)Cl)(F)F.[F] HTEUDFUQTORZIN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 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
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229910052797 bismuth Inorganic materials 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 1
- 150000001845 chromium compounds Chemical class 0.000 description 1
- 229910000423 chromium oxide Inorganic materials 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
- 239000013065 commercial product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 150000002680 magnesium Chemical class 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- GIOZLVMCHDGNNZ-UHFFFAOYSA-N magnesium;oxido-(oxido(dioxo)chromio)oxy-dioxochromium Chemical compound [Mg+2].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O GIOZLVMCHDGNNZ-UHFFFAOYSA-N 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 150000002816 nickel compounds Chemical class 0.000 description 1
- PLHASFSAGNOMLM-UHFFFAOYSA-N nickel(2+);oxido-(oxido(dioxo)chromio)oxy-dioxochromium Chemical compound [Ni+2].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O PLHASFSAGNOMLM-UHFFFAOYSA-N 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- KHADWTWCQJVOQO-UHFFFAOYSA-N zinc;oxido-(oxido(dioxo)chromio)oxy-dioxochromium Chemical compound [Zn+2].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KHADWTWCQJVOQO-UHFFFAOYSA-N 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
使用する触媒は、フッ化アルミニウムに担持されたニッケル/クロム(Ni/Cr原子比率=1)ベースであり、ニッケル塩とクロム塩の溶液を含浸することにより得られる。
活性化は下記工程を含む:
乾燥工程は、大気圧で、約20L/時で導入された窒素流下、約220℃の温度で24時間行い;
第1の活性化工程は、約350℃の温度で、窒素とフッ化水素酸の混合物下で、窒素を徐々に減少させ、3時間純粋なHF下で進行するように行い、その後64時間空気のみの流れの下で行い;
第2の活性化工程は、空気、フッ化水素酸及びHCFO−1233xf(HF/HCFO−1233xfのモル比=20、酸素/HCFO−1233xfのモル比=0.08)を用いて、接触時間を25秒として30時間350℃で行い、次に1.5L/時で導入した空気流下で64時間処理を行い、その後、様々なフッ素化反応を行う。
フッ素化反応は以下の条件で行う:
HF/HCFO−1233xfのモル比=24
酸素/HCFO−1233xfのモル比=1.8又は0.6
接触時間=22秒
大気圧
温度350℃
1690時間後、転換率は44%であり、HFO−1234yf及びHFC−245cbについての選択性は86%である。
これらの条件下で60時間後、HCFO−1233xfの転換率は約32%である。
反応250時間後、転換率は28%であり、HFO−1234yf及びHFC−245cbについての選択性は88%である。
Claims (15)
- 式CX3CHClCH2X及びCX3CFXCH3のハロプロパンと式CX3CCl=CH2、CClX2CCl=CH2及びCX2=CClCH2X(式中、Xは独立してフッ素原子又は塩素原子である)のハロプロペンとから2,3,3,3−テトラフルオロプロペンを製造する方法において、式CX3CHClCH2X及びCX3CFXCH3の少なくとも一つのハロプロパン及び/又は式CClX2CCl=CH2及びCX2=CClCH2X(式中、Xは独立してフッ素原子又は塩素原子である)の少なくとも一つのハロプロペンと混合されていてもよい2−クロロ−3,3,3−トリフルオロ−1−プロペンが、2−クロロ−3,3,3−トリフルオロ−1−プロペンに対する酸素のモル比が1より大きく2.5以下で、反応する全化合物に対するHFのモル比が5〜40である条件下で、320〜420℃の温度、フッ素化触媒の存在下、気相中で、HFと反応する少なくとも一つの工程(FCO)を含む、方法。
- 2−クロロ−3,3,3−トリフルオロ−1−プロペンに対する酸素のモル比が1.25〜2.5である、請求項1に記載の方法。
- 反応する有機化合物に対するHFのモル比が10〜40である、請求項1又は2に記載の方法。
- FCO工程のフッ素化温度が340〜400℃である、請求項1〜3のいずれか一項に記載の方法。
- FCO工程が、0.5〜20バール、好ましくは1〜7バールの圧力で実施される、請求項1〜4のいずれか一項に記載の方法。
- 2−クロロ−3,3,3−トリフルオロ−1−プロペンが、FCO工程に存在する有機化合物の少なくとも20重量%を占める、請求項1〜5のいずれか一項に記載の方法。
- 触媒がバルク又は担持触媒である、請求項1〜6のいずれか一項に記載の方法。
- 触媒がクロムベースである、請求項1〜7のいずれか一項に記載の方法。
- 触媒が共触媒を含む、請求項1〜8のいずれか一項に記載の方法。
- 共触媒がニッケル、マグネシウム及び亜鉛から選択される、請求項9に記載の方法。
- 触媒に、酸素及び/又はHFを含む流れを用いた少なくとも一つの活性化工程を施す、請求項1〜10のいずれか一項に記載の方法。
- 活性化が、式CX3CHClCH2X及びCX3CFXCH3のハロプロパンと式CX3CCl=CH2、CClX2CCl=CH2及びCX2=CClCH2X(式中、Xは独立してフッ素原子又は塩素原子である)のハロプロペンから選択される少なくとも一つの化合物とHFとの酸化剤の存在下でのフッ素化反応によって継続される、請求項11に記載の方法。
- 温度は300〜400℃であり、時間は6〜100時間である、請求項12に記載の方法。
- ハロプロパン又はハロプロペンが、2,3−ジクロロ−1,1,1−トリフルオロプロパン、1,1,1,2,3−ペンタクロロプロパン、2−クロロ−3,3,3−トリフルオロ−1−プロペン及び/又は1,1,2,3−テトラクロロプロペンから選択される、請求項1〜13のいずれか一項に記載の方法。
- 1,1,1,2,3−ペンタクロロプロパンが触媒の存在下で気相中でHFと反応し、2−クロロ−3,3,3−トリフルオロ−1−プロペン、2,3,3,3−テトラフルオロプロペン、及び任意で1,1,1,2,2−ペンタフルオロプロパンを含む流れを生成する少なくとも一つの反応工程と;前記流れから2,3,3,3−テトラフルオロプロペンを分離し、その後前記流れにFCO工程を行う少なくとも1つ工程とを含む、請求項1〜14のいずれか一項に記載の方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1158604 | 2011-09-27 | ||
FR1158604A FR2980474B1 (fr) | 2011-09-27 | 2011-09-27 | Procede de fabrication du 2,3,3,3-tetrafluoropropene |
PCT/FR2012/052097 WO2013045791A1 (fr) | 2011-09-27 | 2012-09-20 | Procede de fabrication du 2,3,3,3-tetrafluoropropene |
Publications (2)
Publication Number | Publication Date |
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JP2014532046A true JP2014532046A (ja) | 2014-12-04 |
JP5905967B2 JP5905967B2 (ja) | 2016-04-20 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2014531294A Active JP5905967B2 (ja) | 2011-09-27 | 2012-09-20 | 2,3,3,3−テトラフルオロプロペンの製造方法 |
Country Status (9)
Country | Link |
---|---|
US (1) | US9061956B2 (ja) |
EP (1) | EP2760811B1 (ja) |
JP (1) | JP5905967B2 (ja) |
CN (1) | CN103827066B (ja) |
ES (1) | ES2561095T3 (ja) |
FR (1) | FR2980474B1 (ja) |
HU (1) | HUE028416T2 (ja) |
PL (1) | PL2760811T3 (ja) |
WO (1) | WO2013045791A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2016130222A (ja) * | 2015-01-13 | 2016-07-21 | ダイキン工業株式会社 | 含フッ素オレフィンの製造方法 |
JP2016132648A (ja) * | 2015-01-21 | 2016-07-25 | ダイキン工業株式会社 | フルオロプロペンの製造方法 |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013088195A1 (en) * | 2011-12-14 | 2013-06-20 | Arkema France | Process for the preparation of 2,3,3,3 tetrafluoropropene |
FR3023286B1 (fr) | 2014-07-02 | 2018-02-16 | Arkema France | Procede de fabrication de tetrafluoropropene |
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FR3078698B1 (fr) | 2018-03-07 | 2020-02-21 | Arkema France | Procede de production du 2-chloro-3,3,3-trifluoropropene |
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FR3078700B1 (fr) | 2018-03-07 | 2020-07-10 | Arkema France | Procede de production du 2,3,3,3-tetrafluoropropene |
CN110975876A (zh) * | 2019-12-31 | 2020-04-10 | 山东华安新材料有限公司 | 一种活性炭负载铬基催化剂及其制备方法和用途 |
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Publication number | Publication date |
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HUE028416T2 (en) | 2016-12-28 |
US9061956B2 (en) | 2015-06-23 |
EP2760811B1 (fr) | 2016-01-06 |
FR2980474A1 (fr) | 2013-03-29 |
PL2760811T3 (pl) | 2016-06-30 |
US20140275653A1 (en) | 2014-09-18 |
WO2013045791A1 (fr) | 2013-04-04 |
EP2760811A1 (fr) | 2014-08-06 |
FR2980474B1 (fr) | 2013-08-30 |
CN103827066B (zh) | 2016-09-28 |
ES2561095T3 (es) | 2016-02-24 |
CN103827066A (zh) | 2014-05-28 |
JP5905967B2 (ja) | 2016-04-20 |
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