JP4785532B2 - ハイドロフルオロカーボンの製造方法、その製品およびその用途 - Google Patents
ハイドロフルオロカーボンの製造方法、その製品およびその用途 Download PDFInfo
- Publication number
- JP4785532B2 JP4785532B2 JP2005513956A JP2005513956A JP4785532B2 JP 4785532 B2 JP4785532 B2 JP 4785532B2 JP 2005513956 A JP2005513956 A JP 2005513956A JP 2005513956 A JP2005513956 A JP 2005513956A JP 4785532 B2 JP4785532 B2 JP 4785532B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrofluorocarbon
- producing
- distillation column
- separated
- gas
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 49
- 239000007789 gas Substances 0.000 claims description 66
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 claims description 50
- 238000004821 distillation Methods 0.000 claims description 46
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 38
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 38
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000003054 catalyst Substances 0.000 claims description 35
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical class C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 31
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 claims description 24
- 238000003682 fluorination reaction Methods 0.000 claims description 15
- 239000002994 raw material Substances 0.000 claims description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 13
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 13
- 229940050176 methyl chloride Drugs 0.000 claims description 12
- 238000000746 purification Methods 0.000 claims description 11
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 claims description 6
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910000423 chromium oxide Inorganic materials 0.000 claims description 4
- 238000000926 separation method Methods 0.000 claims description 3
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 44
- 238000000034 method Methods 0.000 description 39
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000002808 molecular sieve Substances 0.000 description 14
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 14
- 238000005530 etching Methods 0.000 description 11
- 229910021536 Zeolite Inorganic materials 0.000 description 10
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 10
- 239000012071 phase Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000010457 zeolite Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 229910001873 dinitrogen Inorganic materials 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000004140 cleaning Methods 0.000 description 7
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- XWCDCDSDNJVCLO-UHFFFAOYSA-N Chlorofluoromethane Chemical compound FCCl XWCDCDSDNJVCLO-UHFFFAOYSA-N 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910001055 inconels 600 Inorganic materials 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 3
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 3
- 229910021563 chromium fluoride Inorganic materials 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000011148 porous material Substances 0.000 description 3
- FTBATIJJKIIOTP-UHFFFAOYSA-K trifluorochromium Chemical compound F[Cr](F)F FTBATIJJKIIOTP-UHFFFAOYSA-K 0.000 description 3
- CYXIKYKBLDZZNW-UHFFFAOYSA-N 2-Chloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)CCl CYXIKYKBLDZZNW-UHFFFAOYSA-N 0.000 description 2
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003463 adsorbent Substances 0.000 description 2
- 239000012018 catalyst precursor Substances 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 2
- 229940099364 dichlorofluoromethane Drugs 0.000 description 2
- YUCFVHQCAFKDQG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH] YUCFVHQCAFKDQG-UHFFFAOYSA-N 0.000 description 2
- -1 for example Chemical compound 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229910001026 inconel Inorganic materials 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 2
- BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 1
- OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 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
- 239000012024 dehydrating agents Substances 0.000 description 1
- 238000001312 dry etching Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940073584 methylene chloride Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000001020 plasma etching Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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
- 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
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2005513956A JP4785532B2 (ja) | 2003-09-10 | 2004-09-09 | ハイドロフルオロカーボンの製造方法、その製品およびその用途 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003318556 | 2003-09-10 | ||
JP2003318556 | 2003-09-10 | ||
PCT/JP2004/013482 WO2005026090A1 (ja) | 2003-09-10 | 2004-09-09 | ハイドロフルオロカーボンの製造方法、その製品およびその用途 |
JP2005513956A JP4785532B2 (ja) | 2003-09-10 | 2004-09-09 | ハイドロフルオロカーボンの製造方法、その製品およびその用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPWO2005026090A1 JPWO2005026090A1 (ja) | 2006-11-16 |
JP4785532B2 true JP4785532B2 (ja) | 2011-10-05 |
Family
ID=34308524
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2005513956A Expired - Fee Related JP4785532B2 (ja) | 2003-09-10 | 2004-09-09 | ハイドロフルオロカーボンの製造方法、その製品およびその用途 |
Country Status (5)
Country | Link |
---|---|
JP (1) | JP4785532B2 (enrdf_load_stackoverflow) |
KR (1) | KR100643674B1 (enrdf_load_stackoverflow) |
CN (1) | CN1330615C (enrdf_load_stackoverflow) |
TW (1) | TW200516068A (enrdf_load_stackoverflow) |
WO (1) | WO2005026090A1 (enrdf_load_stackoverflow) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2901790A1 (fr) * | 2006-05-30 | 2007-12-07 | Arkema France | Procede de fabrication des hydrofluorocarbures |
CN102762525B (zh) * | 2010-02-17 | 2016-05-04 | 中央硝子株式会社 | 半导体气体的制造方法 |
JP5652179B2 (ja) * | 2010-12-09 | 2015-01-14 | セントラル硝子株式会社 | 半導体ガスの製造方法 |
CN103910600A (zh) * | 2013-01-06 | 2014-07-09 | 中化蓝天集团有限公司 | 超高纯一氟甲烷的制备方法 |
JP2014221727A (ja) * | 2013-05-13 | 2014-11-27 | 昭和電工株式会社 | ジクロロメタンの精製方法およびそれを用いるジフルオロメタンの製造方法 |
JP6261531B2 (ja) * | 2015-02-05 | 2018-01-17 | ダイキン工業株式会社 | フッ化メチルの製造方法 |
CN109748775B (zh) * | 2017-11-08 | 2021-08-17 | 浙江蓝天环保高科技股份有限公司 | 一种hcfc-22生产中副产三氟甲烷的资源化利用方法 |
WO2025150175A1 (ja) * | 2024-01-12 | 2025-07-17 | 三菱電機株式会社 | フロン冷媒の製造方法、フロン冷媒の貯蔵方法、ヒートポンプ装置の製造方法、および二酸化炭素貯蔵システム |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989010341A1 (en) * | 1988-04-28 | 1989-11-02 | Showa Denko Kabushiki Kaisha | Process for producing organofluorine compound |
CN1039118C (zh) * | 1992-03-23 | 1998-07-15 | 浙江省化工研究院 | 气相氟化制备二氟甲烷的改进方法 |
GB9404715D0 (en) * | 1993-03-24 | 1994-04-27 | Ici Plc | Production of difluoromethane |
US5446218A (en) * | 1993-04-26 | 1995-08-29 | E. I. Du Pont De Nemours And Company | Preparation of fluorinated methanes |
JP3582798B2 (ja) * | 1993-06-18 | 2004-10-27 | 昭和電工株式会社 | フッ素化触媒およびフッ素化方法 |
ES2111207T3 (es) * | 1993-06-18 | 1998-03-01 | Showa Denko Kk | Catalizador de fluoracion y procedimiento de fluoracion. |
JPH0717882A (ja) * | 1993-07-05 | 1995-01-20 | Daikin Ind Ltd | ジフルオロメタンの製造方法 |
ES2146740T3 (es) * | 1993-12-09 | 2000-08-16 | Daikin Ind Ltd | Procedimiento de produccion del difluorometano y del 1,1,1,2-tetrafluoroetano. |
WO1996001241A1 (fr) * | 1994-07-01 | 1996-01-18 | Daikin Industries, Ltd. | Procede pour produire du difluoromethane |
KR0125120B1 (ko) * | 1994-07-04 | 1997-12-01 | 김은영 | 불화탄화수소 화합물들의 병산 제조방법 |
BR9607743A (pt) * | 1995-02-10 | 1998-06-23 | Daikin Ind Ltd | Processo para produçao de diflúor metano e diflúor cloro metano |
KR0152580B1 (ko) * | 1995-08-23 | 1998-10-15 | 김은영 | 1,1,1,2-테트라플루오로에탄, 펜타플루오로에탄 및 1,1,1-트리플루오로에탄의 병산 방법 |
US5763708A (en) * | 1995-09-20 | 1998-06-09 | Allied Signal Inc. | Process for the production of difluoromethane |
EP1003699B9 (en) * | 1997-08-12 | 2004-01-07 | E.I. Du Pont De Nemours And Company | Purification of difluoromethane by extractive distillation |
JP2001524459A (ja) * | 1997-11-21 | 2001-12-04 | アライドシグナル・インコーポレイテッド | ハイドロフルオロカーボンの製造方法 |
US6235265B1 (en) * | 1998-10-28 | 2001-05-22 | Alliedsignal Inc. | Evaporative coolant for topical anesthesia comprising hydrofluorocarbons and/or hydrochlorofluorocarbons |
JP4574259B2 (ja) * | 2003-07-24 | 2010-11-04 | 昭和電工株式会社 | フルオロメタンの精製方法 |
-
2004
- 2004-09-08 TW TW093127173A patent/TW200516068A/zh not_active IP Right Cessation
- 2004-09-09 WO PCT/JP2004/013482 patent/WO2005026090A1/ja active Application Filing
- 2004-09-09 CN CNB2004800012200A patent/CN1330615C/zh not_active Expired - Lifetime
- 2004-09-09 KR KR1020057008285A patent/KR100643674B1/ko not_active Expired - Lifetime
- 2004-09-09 JP JP2005513956A patent/JP4785532B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
KR100643674B1 (ko) | 2006-11-10 |
JPWO2005026090A1 (ja) | 2006-11-16 |
TWI325412B (enrdf_load_stackoverflow) | 2010-06-01 |
WO2005026090A1 (ja) | 2005-03-24 |
TW200516068A (en) | 2005-05-16 |
KR20050086475A (ko) | 2005-08-30 |
CN1701056A (zh) | 2005-11-23 |
CN1330615C (zh) | 2007-08-08 |
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