JP6219937B2 - フルオロオレフィン類中のRfCCX不純物の低減のための方法 - Google Patents
フルオロオレフィン類中のRfCCX不純物の低減のための方法 Download PDFInfo
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- JP6219937B2 JP6219937B2 JP2015516186A JP2015516186A JP6219937B2 JP 6219937 B2 JP6219937 B2 JP 6219937B2 JP 2015516186 A JP2015516186 A JP 2015516186A JP 2015516186 A JP2015516186 A JP 2015516186A JP 6219937 B2 JP6219937 B2 JP 6219937B2
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- 239000012535 impurity Substances 0.000 title claims description 170
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- 239000000047 product Substances 0.000 claims description 126
- 150000001412 amines Chemical class 0.000 claims description 91
- FXRLMCRCYDHQFW-UHFFFAOYSA-N 2,3,3,3-tetrafluoropropene Chemical compound FC(=C)C(F)(F)F FXRLMCRCYDHQFW-UHFFFAOYSA-N 0.000 claims description 50
- -1 heterocyclic amines Chemical class 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 239000000460 chlorine Substances 0.000 claims description 44
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- 230000008569 process Effects 0.000 claims description 32
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- 239000001257 hydrogen Substances 0.000 claims description 23
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- 125000003118 aryl group Chemical group 0.000 claims description 15
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- 238000000926 separation method Methods 0.000 description 7
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 description 6
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- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 6
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
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- 125000000623 heterocyclic group Chemical group 0.000 description 5
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- WESZXUPVXXPZHP-UHFFFAOYSA-K [Mg+2].[F-].[F-].[F-].[Cr+3] Chemical compound [Mg+2].[F-].[F-].[F-].[Cr+3] WESZXUPVXXPZHP-UHFFFAOYSA-K 0.000 description 1
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- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
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- 230000008859 change Effects 0.000 description 1
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- 125000001309 chloro group Chemical group Cl* 0.000 description 1
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- YOCUPQPZWBBYIX-UHFFFAOYSA-N copper nickel Chemical compound [Ni].[Cu] YOCUPQPZWBBYIX-UHFFFAOYSA-N 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 238000006073 displacement reaction Methods 0.000 description 1
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 1
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- 229960003750 ethyl chloride Drugs 0.000 description 1
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- 150000002390 heteroarenes Chemical class 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- WJLUBOLDZCQZEV-UHFFFAOYSA-M hexadecyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCCCCCCCCCC[N+](C)(C)C WJLUBOLDZCQZEV-UHFFFAOYSA-M 0.000 description 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 1
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 1
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- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
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- 239000012074 organic phase Substances 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 1
- WTSXICLFTPPDTL-UHFFFAOYSA-N pentane-1,3-diamine Chemical compound CCC(N)CCN WTSXICLFTPPDTL-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
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- 235000021317 phosphate Nutrition 0.000 description 1
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- 239000004033 plastic Substances 0.000 description 1
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 description 1
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- 230000001737 promoting effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960005335 propanol Drugs 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
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- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003865 secondary ammonium salts Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 229940063673 spermidine Drugs 0.000 description 1
- 229940063675 spermine Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003866 tertiary ammonium salts Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- IBWGNZVCJVLSHB-UHFFFAOYSA-M tetrabutylphosphanium;chloride Chemical compound [Cl-].CCCC[P+](CCCC)(CCCC)CCCC IBWGNZVCJVLSHB-UHFFFAOYSA-M 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 1
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 1
- BRKFQVAOMSWFDU-UHFFFAOYSA-M tetraphenylphosphanium;bromide Chemical compound [Br-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 BRKFQVAOMSWFDU-UHFFFAOYSA-M 0.000 description 1
- WAGFXJQAIZNSEQ-UHFFFAOYSA-M tetraphenylphosphonium chloride Chemical compound [Cl-].C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 WAGFXJQAIZNSEQ-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000006269 thermoset foam Substances 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 229910000314 transition metal oxide Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- 125000006617 triphenylamine group Chemical group 0.000 description 1
- ADZJWYULTMTLQZ-UHFFFAOYSA-N tritylphosphane;hydrobromide Chemical compound [Br-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 ADZJWYULTMTLQZ-UHFFFAOYSA-N 0.000 description 1
- PPQRADLPLZYEKN-UHFFFAOYSA-N tritylphosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1C(C=1C=CC=CC=1)([PH3+])C1=CC=CC=C1 PPQRADLPLZYEKN-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B63/00—Purification; Separation; Stabilisation; Use of additives
- C07B63/04—Use of additives
-
- 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
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- 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
- C07C17/42—Use of additives, e.g. for stabilisation
-
- 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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
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| PCT/US2013/044418 WO2013184865A1 (en) | 2012-06-06 | 2013-06-06 | PROCESS FOR THE REDUCTION OF RfCCX IMPURITIES IN FLUOROOLEFINS |
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| JP2017188572A Pending JP2017222885A (ja) | 2012-06-06 | 2017-09-28 | フルオロオレフィン組成物 |
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| FR2962130B1 (fr) * | 2010-06-30 | 2012-07-20 | Arkema France | Composition a base de 2,3,3,3-tetrafluoropropene |
| FR2962442B1 (fr) | 2010-07-09 | 2016-02-26 | Arkema France | Composition stable de 2,3,3,3-tetrafluoropropene |
| CN111718234A (zh) * | 2014-04-16 | 2020-09-29 | 科慕埃弗西有限公司 | 将氯氟丙烷和氯氟丙烯转化成更需要的氟丙烷和氟丙烯 |
| EP3241878B2 (en) | 2014-09-25 | 2023-12-20 | Daikin Industries, Ltd. | Composition comprising hfc and hfo |
| CN106715669B (zh) * | 2014-10-02 | 2019-05-10 | 中央硝子株式会社 | 含有2-氯-1,3,3,3-四氟丙烯和1-氯-3,3,3-三氟丙烯的类共沸组合物 |
| FR3033791B1 (fr) | 2015-03-18 | 2017-04-14 | Arkema France | Stabilisation du 1-chloro-3,3,3-trifluoropropene |
| JP6962822B2 (ja) | 2015-05-21 | 2021-11-05 | ザ ケマーズ カンパニー エフシー リミテッド ライアビリティ カンパニー | SbF5による1233xfの244bbへのフッ化水素処理 |
| GB2540427B (en) | 2015-07-17 | 2017-07-19 | Mexichem Fluor Sa De Cv | Process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) |
| JP6274363B2 (ja) | 2015-07-27 | 2018-02-07 | 旭硝子株式会社 | 溶剤組成物、洗浄方法、塗膜の形成方法、熱移動媒体および熱サイクルシステム |
| MX2018002065A (es) | 2015-08-19 | 2018-06-06 | Spolek Pro Chemickou A Hutni Vyrobu As | Proceso para generar compuestos de alcano y alqueno clorado de 3 atomos de carbono. |
| CN107922294A (zh) * | 2015-09-11 | 2018-04-17 | 科慕埃弗西有限公司 | 氢氯氟烃的脱卤化氢 |
| JP6971226B2 (ja) * | 2015-10-15 | 2021-11-24 | ハネウェル・インターナショナル・インコーポレーテッドHoneywell International Inc. | 脱ハロゲン化水素化反応器及び方法 |
| EP3442936B1 (en) | 2016-04-13 | 2023-09-06 | SPOLCHEMlE Zebra, a.s. | Process |
| JP6908042B2 (ja) * | 2016-07-29 | 2021-07-21 | Agc株式会社 | 熱サイクル用作動媒体 |
| CN109923096B (zh) | 2016-11-02 | 2022-06-21 | 霍尼韦尔国际公司 | 减少2,3,3,3-四氟丙烯中的3,3,3-三氟丙炔的方法 |
| GB201701099D0 (en) * | 2017-01-23 | 2017-03-08 | Mexichem Fluor Sa De Cv | Process |
| WO2019022140A1 (ja) * | 2017-07-26 | 2019-01-31 | Agc株式会社 | 熱サイクルシステムおよびそれを用いた熱サイクル方法 |
| US10233137B1 (en) * | 2017-10-13 | 2019-03-19 | Honeywell International Inc. | Method for removing unsaturated halogenated impurities from 2,3,3,3-tetrafluoropropene (HFO-1234yf) |
| JP6974221B2 (ja) * | 2018-03-14 | 2021-12-01 | 株式会社クレハ | アルケンの製造方法 |
| WO2019230842A1 (ja) * | 2018-05-30 | 2019-12-05 | Agc株式会社 | 1-クロロ-2,3,3,4,4,5,5-ヘプタフルオロ-1-ペンテンの製造方法 |
| CN112313199A (zh) | 2018-06-06 | 2021-02-02 | 霍尼韦尔国际公司 | 用于HCFC-244bb的脱氯化氢以制备HFO-1234yf的方法 |
| CN112566887A (zh) * | 2018-08-13 | 2021-03-26 | 科慕埃弗西有限公司 | 用于制备氯氟烯烃的组合物和方法 |
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| US5155082A (en) | 1991-04-12 | 1992-10-13 | Allied-Signal Inc. | Catalyst for the manufacture of chlorofluorocarbons, hydrochlorofluorocarbons and hydrofluorocarbons |
| JPH04346949A (ja) * | 1991-05-22 | 1992-12-02 | Asahi Glass Co Ltd | ヘキサフルオロプロピレンの精製方法 |
| DE4205341A1 (de) | 1992-02-21 | 1993-08-26 | Pharmpur Gmbh | Verfahren zur reinigung von perfluorcarbonen und verwendung der gereinigten perfluorcarbone |
| US6013846A (en) | 1998-03-05 | 2000-01-11 | Elf Atochem North America, Inc. | Azeotrope of HF and 1233zd |
| US6774270B1 (en) * | 2003-04-01 | 2004-08-10 | 3M Innovative Properties Company | Method of removing hexafluoropropylene dimers |
| US8084653B2 (en) | 2004-04-29 | 2011-12-27 | Honeywell International, Inc. | Method for producing fluorinated organic compounds |
| US8058486B2 (en) * | 2004-04-29 | 2011-11-15 | Honeywell International Inc. | Integrated process to produce 2,3,3,3-tetrafluoropropene |
| US7897823B2 (en) | 2004-10-29 | 2011-03-01 | E. I. Du Pont De Nemours And Company | Process for production of azeotrope compositions comprising hydrofluoroolefin and hydrogen fluoride and uses of said azeotrope compositions in separation processes |
| EP2377610A3 (en) | 2004-12-22 | 2012-02-08 | E. I. Du Pont De Nemours And Company | Process for increasing the fluorine content by photochemical reactions |
| US7569170B2 (en) * | 2005-03-04 | 2009-08-04 | E.I. Du Pont De Nemours And Company | Compositions comprising a fluoroolefin |
| US7476771B2 (en) | 2005-11-01 | 2009-01-13 | E.I. Du Pont De Nemours + Company | Azeotrope compositions comprising 2,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US7423188B2 (en) | 2005-11-01 | 2008-09-09 | E. I. Du Pont De Nemours And Company | Azeotrope compositions comprising E-1,3,3,3-tetrafluoropropene and hydrogen fluoride and uses thereof |
| US8766020B2 (en) | 2008-07-31 | 2014-07-01 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| DK3336074T3 (da) * | 2006-01-03 | 2025-08-25 | Honeywell Int Inc | Fremgangsmåde til produktion af fluorinerede, organiske forbindelser |
| JP2009542650A (ja) | 2006-06-27 | 2009-12-03 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | テトラフルオロプロペン製造方法 |
| US8377327B2 (en) | 2006-06-27 | 2013-02-19 | E I Du Pont De Nemours And Company | Tetrafluoropropene production processes |
| MX337217B (es) | 2006-10-03 | 2016-02-18 | Mexichem Amanco Holding Sa | Procedimiento de dehidrogenacion-halogenacion para la produccion de (hidro)fluoroalquenos de c3-c6. |
| ES2542306T5 (es) | 2006-10-31 | 2022-03-30 | Chemours Co Fc Llc | Procedimientos para la producción de fluoropropanos y halopropenos |
| EP2158176A4 (en) * | 2007-06-27 | 2011-11-09 | Arkema Inc | TWO-STAGE PROCESS FOR THE PREPARATION OF HYDROFLUOROLEFINES |
| FR2933402B1 (fr) * | 2008-07-03 | 2010-07-30 | Arkema France | Procede de purification de 2,3,3,3-tetrafluoro-1-propene (hfo1234yf) |
| US8975454B2 (en) * | 2008-07-31 | 2015-03-10 | Honeywell International Inc. | Process for producing 2,3,3,3-tetrafluoropropene |
| US8203022B2 (en) | 2008-10-27 | 2012-06-19 | E I Du Pont De Nemours And Company | Conversion of 2-chloro-1,1,1,2-tetrafluoropropane to 2,3,3,3-tetrafluoropropene |
| US8609909B2 (en) * | 2009-01-30 | 2013-12-17 | Honeywell International Inc. | Process for the purification of hydrofluoroolefins |
| TW201100357A (en) | 2009-05-08 | 2011-01-01 | Du Pont | Processes for reducing the amount of monofluoroacetate in hydrofluoroolefin production |
| US7985884B2 (en) | 2009-06-03 | 2011-07-26 | E. I. Du Pont De Nemours And Company | Process to manufacture 2,3,3,3-tetrafluoropropene |
| GB0918069D0 (en) * | 2009-10-15 | 2009-12-02 | Ineos Fluor Holdings Ltd | Process |
| WO2011077191A1 (en) | 2009-12-23 | 2011-06-30 | Arkema France | Catalytic gas phase fluorination of 1230xa to 1234yf |
| FR2962130B1 (fr) * | 2010-06-30 | 2012-07-20 | Arkema France | Composition a base de 2,3,3,3-tetrafluoropropene |
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2013
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- 2013-06-06 IN IN10381DEN2014 patent/IN2014DN10381A/en unknown
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- 2013-06-06 EP EP13800895.8A patent/EP2867193B1/en not_active Not-in-force
- 2013-06-06 EP EP17204288.9A patent/EP3309140A1/en not_active Withdrawn
- 2013-06-06 CN CN201710127721.2A patent/CN107032947A/zh active Pending
- 2013-06-06 WO PCT/US2013/044418 patent/WO2013184865A1/en not_active Ceased
- 2013-06-06 KR KR20147036894A patent/KR20150021551A/ko not_active Abandoned
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- 2013-06-06 MX MX2014014877A patent/MX359553B/es active IP Right Grant
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2017
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2019
- 2019-06-12 JP JP2019109335A patent/JP2019147842A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
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| CN107032947A (zh) | 2017-08-11 |
| JP2015518898A (ja) | 2015-07-06 |
| WO2013184865A1 (en) | 2013-12-12 |
| EP2867193B1 (en) | 2018-01-10 |
| MX2014014877A (es) | 2015-03-09 |
| KR20150021551A (ko) | 2015-03-02 |
| MX359553B (es) | 2018-10-02 |
| CN104507895A (zh) | 2015-04-08 |
| CN104507895B (zh) | 2017-03-22 |
| EP3309140A1 (en) | 2018-04-18 |
| EP2867193A4 (en) | 2016-01-27 |
| JP2019147842A (ja) | 2019-09-05 |
| EP2867193A1 (en) | 2015-05-06 |
| JP2017222885A (ja) | 2017-12-21 |
| US8987536B2 (en) | 2015-03-24 |
| US20140018582A1 (en) | 2014-01-16 |
| IN2014DN10381A (enExample) | 2015-08-14 |
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