JP4549340B2 - 1−クロロ−1、3、3、3−テトラフルオロプロパン及び1、2−ジクロロ−3、3、3−トリフルオロプロペンの共沸類組成物 - Google Patents
1−クロロ−1、3、3、3−テトラフルオロプロパン及び1、2−ジクロロ−3、3、3−トリフルオロプロペンの共沸類組成物 Download PDFInfo
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- JP4549340B2 JP4549340B2 JP2006514322A JP2006514322A JP4549340B2 JP 4549340 B2 JP4549340 B2 JP 4549340B2 JP 2006514322 A JP2006514322 A JP 2006514322A JP 2006514322 A JP2006514322 A JP 2006514322A JP 4549340 B2 JP4549340 B2 JP 4549340B2
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- trifluoropropene
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- tetrafluoropropane
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- 239000000203 mixture Substances 0.000 title claims description 107
- ZHJBJVPTRJNNIK-UPHRSURJSA-N (z)-1,2-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(\Cl)=C\Cl ZHJBJVPTRJNNIK-UPHRSURJSA-N 0.000 title claims description 24
- ZGOMEYREADWKLC-UHFFFAOYSA-N 3-chloro-1,1,1,3-tetrafluoropropane Chemical group FC(Cl)CC(F)(F)F ZGOMEYREADWKLC-UHFFFAOYSA-N 0.000 title claims description 21
- 238000009835 boiling Methods 0.000 claims description 32
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 claims description 22
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 18
- 238000004821 distillation Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000013067 intermediate product Substances 0.000 claims description 7
- VVWFZKBKXPXGBH-UHFFFAOYSA-N 1,1,1,3,3-pentachloropropane Chemical compound ClC(Cl)CC(Cl)(Cl)Cl VVWFZKBKXPXGBH-UHFFFAOYSA-N 0.000 claims description 5
- ISCYUDAHBJMFNT-UHFFFAOYSA-N 1,1-dichloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C(Cl)Cl ISCYUDAHBJMFNT-UHFFFAOYSA-N 0.000 claims 3
- 239000007788 liquid Substances 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000006227 byproduct Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 5
- 239000004604 Blowing Agent Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003507 refrigerant Substances 0.000 description 3
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- -1 heat transfer media Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 2
- 229940029284 trichlorofluoromethane Drugs 0.000 description 2
- JRHNUZCXXOTJCA-UHFFFAOYSA-N 1-fluoropropane Chemical compound CCCF JRHNUZCXXOTJCA-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KYKAJFCTULSVSH-UHFFFAOYSA-N chloro(fluoro)methane Chemical compound F[C]Cl KYKAJFCTULSVSH-UHFFFAOYSA-N 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 239000005437 stratosphere Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/50—Solvents
- C11D7/5036—Azeotropic mixtures containing halogenated solvents
- C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
- C11D7/5045—Mixtures of (hydro)chlorofluorocarbons
-
- 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
- C07C19/00—Acyclic saturated compounds containing halogen atoms
- C07C19/08—Acyclic saturated compounds containing halogen atoms containing fluorine
- C07C19/10—Acyclic saturated compounds containing halogen atoms containing fluorine and chlorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/18—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
- C11D7/22—Organic compounds
- C11D7/28—Organic compounds containing halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
(a)フッ化水素を1、1、1、3、3−ペンタクロロプロパン(HCC−240fa)と反応させて、中間組成物を作る段階と、
(b)その後、1、2−ジクロロ−3、3、3−トリフルオロプロペン(HCFC−1223xd)と1−クロロ−1、3、3、3−テトラフルオロプロパン(HCFC−244fa)の共沸及び共沸類組成物を中間組成物から分離させる段階と、から成る。
例1
HFC−245faを調製するのに、略400ポンドのアンチモニ五塩化物触媒を50ガロン反応器に装填した。反応器の温度を、約95℃まで上げた。HCC−240faを約25lbs/hrで、HFを約15lbs/hrで、及びCl2を2lbs/hrで、連続して反応器に送り、Cl2で触媒を活性化し続けた。反応器の圧力は約215psiaに維持した。生成物ストリームには、HFC−245fa、HF、HCL、及び、1、2−ジクロロ−3、3、3−トリフルオロプロペン(HCFC−1223xd)と1−クロロ−1、3、3、3−テトラフルオロプロパン(HCFC−244fa)を含む少量の有機副産物が含まれていた。次に、未反応のHFとHClを、大部分のHFC−245faと共に取り除き、副産物の混合物が残った。これらの副産物の蒸留を実施し、そこからは、主にHFC−245fa、HCFC−244fa及びHCFC−1223xdを含む軽留分を得た。この留分を更に蒸留して、再生使用可能な成分を回収した。HFC−245faを、蒸留装置内で約55psiaで取り除いた。HCFC−244faの除去には、全体留分を通して、重量で約3.5%のHCFC−1223xdが共沸又は共沸類混合物として伴った。この留分の除去の後には、実質的に純粋なHCFC−1223xdの残余物が残った。
例2
例1からのHCFC−244faが豊富な蒸留留分を、別の分留装置で、大気圧で再び分留した。その結果、全蒸留を通して、重量で約3.5%のHCFC−1223xdを含んでいる一定沸騰の留出物が得られた。これは、約41℃の沸点で起きる。
Claims (20)
- 1−クロロ−1、3、3、3−テトラフルオロプロパンと、1、2−ジクロロ−3、3、3−トリフルオロプロペンとを含む共沸又は共沸類組成物。
- 0を超え50までの重量百分率の1、2−ジクロロ−3、3、3−トリフルオロプロペンと、50から100未満の重量百分率の1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む共沸又は共沸類組成物。
- 1から50重量百分率の1、2−ジクロロ−3、3、3−トリフルオロプロペンと、50から99重量百分率の1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む、請求項2に記載の組成物。
- 1から4重量百分率の1、2−ジクロロ−3、3、3−トリフルオロプロペンと、96から99重量百分率の1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む、請求項2に記載の組成物。
- 3.5重量百分率の1、2−ジクロロ−3、3、3−トリフルオロプロペンと、96.5重量百分率の1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む、請求項2に記載の組成物。
- 前記組成物は、14psiaから215psiaの圧力で、41℃から160℃の沸点を有する、請求項1に記載の組成物。
- 前記組成物は、15psiaから80psiaの圧力で、41℃から100℃の沸点を有する、請求項1に記載の組成物。
- 前記組成物は、78psiaの圧力で96.5℃の沸点を有する、請求項1に記載の組成物。
- 前記組成物は、3.5%の1、2−ジクロロ−3、3、3−トリフルオロプロペンを含んでいる、請求項8に記載の組成物。
- 前記組成物は、大気圧で41℃の沸点を有する、請求項1に記載の組成物。
- 1、2−ジクロロ−3、3、3−トリフルオロプロペンと1−クロロ−1、3、3、3−テトラフルオロプロパンの共沸又は共沸類組成物を形成するためのプロセスにおいて、
(a)フッ化水素を1、1、1、3、3−ペンタクロロプロパンと反応させ、中間組成物を生成する段階と、
(b)1、2−ジクロロ−3、3、3−トリフルオロプロペンと1−クロロ−1、3、3、3−テトラフルオロプロパンの共沸又は共沸類組成物を、前記中間組成物から分離させる段階と、から成るプロセス。 - (a)フッ化水素を1、1、1、3、3−ペンタクロロプロパンと反応させ、1、1、1、3、3−ペンタフルオロプロパンと、フッ化水素と、塩酸と、1、2−ジクロロ−3、3、3−トリフルオロプロペンと、1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む中間組成物を生成する段階と、
(b)1、1、1、3、3−ペンタフルオロプロパン、フッ化水素及び塩酸を、前記中間生成物から分離させ、1、2−ジクロロ−3、3、3−トリフルオロプロペンと1−クロロ−1、3、3、3−テトラフルオロプロパンの共沸又は共沸類組成物を形成する段階と、を含んでいる、請求項11に記載のプロセス。 - (a)フッ化水素を1、1、1、3、3−ペンタクロロプロパンと反応させ、1、1、1、3、3−ペンタフルオロプロパンと、フッ化水素と、塩酸と、1、2−ジクロロ−3、3、3−トリフルオロプロペンと、1−クロロ−1、3、3、3−テトラフルオロプロパンとを含む中間組成物を生成する段階と、
(b)前記中間生成物から、フッ化水素、塩酸、及び、前記1、1、1、3、3−ペンタフルオロプロパンの少なくとも一部を取り除き、残存物が残る段階と、
(c)前記残存物を蒸留して、残っている1、1、1、3、3−ペンタフルオロプロパンを取り除き、1−クロロ−1、3、3、3−テトラフルオロプロパンと1、2−ジクロロ−3、3、3−トリフルオロプロペンとの共沸又は共沸類組成物を残す段階と、を含んでいる、請求項11に記載のプロセス。 - 前記生成された共沸又は共沸類組成物は、1重量パーセントから4重量パーセントの1、2−ジクロロ−3、3、3−トリフルオロプロペンと、96重量パーセントから99重量パーセントの1−クロロ−1、3、3、3−テトラフルオロプロパンを含んでいる、請求項13に記載のプロセス。
- 前記蒸留は、1psiaから250psiaの圧力で実施される、請求項13に記載のプロセス。
- 前記蒸留は、15psiaから150psiaの圧力で実施される、請求項13に記載のプロセス。
- 前記蒸留は、20psiaから80psiaの圧力で実施される、請求項13に記載のプロセス。
- 前記蒸留は、30℃から160℃の温度で実施される、請求項13に記載のプロセス。
- 前記蒸留は、35℃から120℃の温度で実施される、請求項13に記載のプロセス。
- 前記蒸留は、41℃から97℃の温度で実施される、請求項13に記載のプロセス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/430,078 US6759381B1 (en) | 2003-05-06 | 2003-05-06 | Azeotrope-like compositions of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene |
PCT/US2004/014282 WO2004099109A1 (en) | 2003-05-06 | 2004-05-06 | Azeotrope-like compositions of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene |
Publications (2)
Publication Number | Publication Date |
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JP2006525374A JP2006525374A (ja) | 2006-11-09 |
JP4549340B2 true JP4549340B2 (ja) | 2010-09-22 |
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Application Number | Title | Priority Date | Filing Date |
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JP2006514322A Expired - Lifetime JP4549340B2 (ja) | 2003-05-06 | 2004-05-06 | 1−クロロ−1、3、3、3−テトラフルオロプロパン及び1、2−ジクロロ−3、3、3−トリフルオロプロペンの共沸類組成物 |
Country Status (4)
Country | Link |
---|---|
US (1) | US6759381B1 (ja) |
JP (1) | JP4549340B2 (ja) |
CN (1) | CN1816507B (ja) |
WO (1) | WO2004099109A1 (ja) |
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US6500795B2 (en) * | 2001-01-24 | 2002-12-31 | Honeywell International Inc. | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
US20050096246A1 (en) | 2003-11-04 | 2005-05-05 | Johnson Robert C. | Solvent compositions containing chlorofluoroolefins |
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KR102652080B1 (ko) * | 2016-12-02 | 2024-03-28 | 허니웰 인터내셔날 인코포레이티드 | Hcfo-1233zd를 건조시키는 방법 |
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CN114149790B (zh) * | 2021-11-10 | 2023-09-05 | 浙江巨化新材料研究院有限公司 | 一种共沸或类共沸组合物及其制备方法 |
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DE770048T1 (de) | 1994-07-11 | 1998-01-02 | Allied Signal Inc | Verfahren zur herstellung von 1,1,1,3,3-pentafluorpropan |
JP3518169B2 (ja) * | 1996-05-31 | 2004-04-12 | ダイキン工業株式会社 | 1,1,1,3,3−ペンタフルオロプロパンの製造方法 |
US6001796A (en) | 1996-07-03 | 1999-12-14 | Alliedsignal Inc. | Azeotrope-like compositions of 1,1,1,3,3-pentafluoropropane and hydrogen fluoride |
US5918481A (en) * | 1997-11-20 | 1999-07-06 | Alliedsignal Inc. | Process for separating hydrogen fluoride from fluorocarbons |
US6514928B1 (en) | 1999-03-15 | 2003-02-04 | Alliedsignal Inc. | Azeotrope-like compositions of pentafluoropropane and water |
US6518467B2 (en) | 2000-12-29 | 2003-02-11 | Honeywell International Inc. | Method of making hydrofluorocarbons and hydrochlorofluorocarbons |
US6534467B2 (en) | 2001-01-24 | 2003-03-18 | Honeywell International Inc. | Azeotrope-like composition of 1,2,2-trichloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
US6475971B2 (en) * | 2001-01-24 | 2002-11-05 | Honeywell International Inc. | Azeotrope-like composition of 1,2-dichloro-3,3,3-trifluoropropene and hydrogen fluoride composition |
US6500795B2 (en) * | 2001-01-24 | 2002-12-31 | Honeywell International Inc. | Azeotrope-like composition of 1-chloro-1,3,3,3-tetrafluoropropane and hydrogen fluoride |
WO2002059067A1 (en) * | 2001-01-25 | 2002-08-01 | Honeywell International, Inc. | Process for the manufacture of fluorocarbons |
US6365566B1 (en) | 2001-03-21 | 2002-04-02 | Honeywell International Inc. | Azeotrope-like compositions of pentafluorobutane and water |
US6524496B2 (en) | 2001-03-21 | 2003-02-25 | Honeywell International Inc. | Azeotrope-like composition of 1,1,1,3,3-pentafluoropropane and 1-chloro-1,1,3,3,3-pentafluoropropane |
-
2003
- 2003-05-06 US US10/430,078 patent/US6759381B1/en not_active Expired - Lifetime
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2004
- 2004-05-06 JP JP2006514322A patent/JP4549340B2/ja not_active Expired - Lifetime
- 2004-05-06 CN CN2004800191785A patent/CN1816507B/zh not_active Expired - Lifetime
- 2004-05-06 WO PCT/US2004/014282 patent/WO2004099109A1/en active Application Filing
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WO2004099109A1 (en) | 2004-11-18 |
US6759381B1 (en) | 2004-07-06 |
CN1816507B (zh) | 2012-05-16 |
JP2006525374A (ja) | 2006-11-09 |
CN1816507A (zh) | 2006-08-09 |
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