CA1049048A - Process for the preparation of 1-chloro-2,2,2-trifluoroethyl-difluoromethyl ether - Google Patents
Process for the preparation of 1-chloro-2,2,2-trifluoroethyl-difluoromethyl etherInfo
- Publication number
- CA1049048A CA1049048A CA74206865A CA206865A CA1049048A CA 1049048 A CA1049048 A CA 1049048A CA 74206865 A CA74206865 A CA 74206865A CA 206865 A CA206865 A CA 206865A CA 1049048 A CA1049048 A CA 1049048A
- Authority
- CA
- Canada
- Prior art keywords
- chloro
- ether
- trifluoroethyl
- chlorine
- mols
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 24
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- PIWKPBJCKXDKJR-UHFFFAOYSA-N Isoflurane Chemical compound FC(F)OC(Cl)C(F)(F)F PIWKPBJCKXDKJR-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 229960002725 isoflurane Drugs 0.000 title claims abstract description 6
- 239000000460 chlorine Substances 0.000 claims abstract description 23
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 22
- DGPDBAGEACUZIU-UHFFFAOYSA-N 1,1,2-trichloro-3,3,3-trifluoro-1-(1,1,2-trichloro-3,3,3-trifluoropropoxy)propane Chemical compound FC(F)(F)C(Cl)C(Cl)(Cl)OC(Cl)(Cl)C(Cl)C(F)(F)F DGPDBAGEACUZIU-UHFFFAOYSA-N 0.000 claims abstract description 9
- SUAGQINKYPWOCB-UHFFFAOYSA-N 2-chloro-3-(2-chloro-3,3,3-trifluoropropoxy)-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)COCC(Cl)C(F)(F)F SUAGQINKYPWOCB-UHFFFAOYSA-N 0.000 claims abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 238000003682 fluorination reaction Methods 0.000 claims description 9
- 238000004508 fractional distillation Methods 0.000 claims description 8
- 238000005660 chlorination reaction Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- YPIJPGVUIOUMKF-UHFFFAOYSA-N 2,3-dichloro-3-(1,2-dichloro-3,3,3-trifluoropropoxy)-1,1,1-trifluoropropane Chemical compound FC(F)(F)C(Cl)C(Cl)OC(Cl)C(Cl)C(F)(F)F YPIJPGVUIOUMKF-UHFFFAOYSA-N 0.000 claims 2
- 150000002170 ethers Chemical class 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- -1 2,2,2-trifluoroethyl-difluoromethyl Chemical group 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000005194 fractionation Methods 0.000 description 5
- 229910052759 nickel Inorganic materials 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 4
- OHLVGBXMHDWRRX-UHFFFAOYSA-N 1,1,1-trifluoro-2-methoxyethane Chemical compound COCC(F)(F)F OHLVGBXMHDWRRX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- GGWSEJRWXOJLNT-UHFFFAOYSA-N 1,1-dichloro-1-(1,1-dichloro-3,3,3-trifluoropropoxy)-3,3,3-trifluoropropane Chemical compound FC(F)(F)CC(Cl)(Cl)OC(Cl)(Cl)CC(F)(F)F GGWSEJRWXOJLNT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 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 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- MCWPMXPNJVZOTP-UHFFFAOYSA-N 2,3-dihydro-1,4-benzodioxin-5-ylboronic acid Chemical compound O1CCOC2=C1C=CC=C2B(O)O MCWPMXPNJVZOTP-UHFFFAOYSA-N 0.000 description 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
- 229910000851 Alloy steel Inorganic materials 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000003983 inhalation anesthetic agent Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229910052573 porcelain Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/123—Saturated ethers containing halogen both carbon chains are substituted by halogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732344442 DE2344442A1 (de) | 1973-09-04 | 1973-09-04 | Verfahren zur herstellung von 1-chlor2,2,2-trifluoraethyl-difluormethylaether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049048A true CA1049048A (en) | 1979-02-20 |
Family
ID=5891541
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA74206865A Expired CA1049048A (en) | 1973-09-04 | 1974-08-09 | Process for the preparation of 1-chloro-2,2,2-trifluoroethyl-difluoromethyl ether |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5076009A (de) |
| AT (1) | AT345264B (de) |
| BE (1) | BE818753A (de) |
| CA (1) | CA1049048A (de) |
| CH (1) | CH597122A5 (de) |
| DE (1) | DE2344442A1 (de) |
| DK (1) | DK136183C (de) |
| ES (1) | ES428971A1 (de) |
| FR (1) | FR2242356B3 (de) |
| GB (1) | GB1475387A (de) |
| NL (1) | NL7410485A (de) |
| SE (1) | SE7410167L (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56137657A (en) * | 1980-03-29 | 1981-10-27 | Chiyou Lsi Gijutsu Kenkyu Kumiai | Manufacture of semiconductor device |
| DE3276530D1 (en) * | 1982-08-17 | 1987-07-16 | Daikin Ind Ltd | Process for preparing 1,1,2-trifluoro-2-chloroethyl difluoromethyl ether |
| WO2013005178A1 (en) * | 2011-07-05 | 2013-01-10 | Piramal Healthcare Limited | A continuous process for purification of 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (isoflurane) |
-
1973
- 1973-09-04 DE DE19732344442 patent/DE2344442A1/de active Pending
-
1974
- 1974-08-05 ES ES428971A patent/ES428971A1/es not_active Expired
- 1974-08-05 NL NL7410485A patent/NL7410485A/xx not_active Application Discontinuation
- 1974-08-07 GB GB3485674A patent/GB1475387A/en not_active Expired
- 1974-08-08 FR FR7427625A patent/FR2242356B3/fr not_active Expired
- 1974-08-08 SE SE7410167A patent/SE7410167L/xx unknown
- 1974-08-09 CA CA74206865A patent/CA1049048A/en not_active Expired
- 1974-08-09 AT AT655774A patent/AT345264B/de not_active IP Right Cessation
- 1974-08-09 DK DK426674A patent/DK136183C/da active
- 1974-08-09 CH CH1091374A patent/CH597122A5/xx not_active IP Right Cessation
- 1974-08-10 JP JP49091914A patent/JPS5076009A/ja active Pending
- 1974-08-12 BE BE147524A patent/BE818753A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES428971A1 (es) | 1976-09-01 |
| CH597122A5 (de) | 1978-03-31 |
| NL7410485A (nl) | 1975-03-06 |
| FR2242356A1 (de) | 1975-03-28 |
| AT345264B (de) | 1978-09-11 |
| GB1475387A (en) | 1977-06-01 |
| FR2242356B3 (de) | 1977-06-03 |
| DK136183B (da) | 1977-08-29 |
| SE7410167L (de) | 1975-03-05 |
| DK136183C (da) | 1978-01-30 |
| DK426674A (de) | 1975-05-05 |
| JPS5076009A (de) | 1975-06-21 |
| ATA655774A (de) | 1978-01-15 |
| BE818753A (fr) | 1975-02-12 |
| DE2344442A1 (de) | 1975-04-03 |
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