DE1643992A1 - Fluorierte AEther und Verfahren zu ihrer Herstellung - Google Patents
Fluorierte AEther und Verfahren zu ihrer HerstellungInfo
- Publication number
- DE1643992A1 DE1643992A1 DE19671643992 DE1643992A DE1643992A1 DE 1643992 A1 DE1643992 A1 DE 1643992A1 DE 19671643992 DE19671643992 DE 19671643992 DE 1643992 A DE1643992 A DE 1643992A DE 1643992 A1 DE1643992 A1 DE 1643992A1
- Authority
- DE
- Germany
- Prior art keywords
- group
- ether
- dichloromethyl
- carbon atoms
- perfluoroalkyl
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 8
- 150000002170 ethers Chemical class 0.000 title claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 17
- -1 chlorobromaethyl group Chemical group 0.000 claims description 12
- 206010002091 Anaesthesia Diseases 0.000 claims description 4
- 230000037005 anaesthesia Effects 0.000 claims description 4
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003983 inhalation anesthetic agent Substances 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000005660 chlorination reaction Methods 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000004508 fractional distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000003193 general anesthetic agent Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229940035674 anesthetics Drugs 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000004081 narcotic agent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- 230000002618 waking effect Effects 0.000 description 2
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 1
- CRJVPUWOURIOCW-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,2-pentafluoroethane Chemical compound CCOC(F)(F)C(F)(F)F CRJVPUWOURIOCW-UHFFFAOYSA-N 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- MZFMJRBUTDYLCV-UHFFFAOYSA-N FC(C(OC(C(F)(F)F)(Cl)Cl)(Cl)Cl)(F)F Chemical compound FC(C(OC(C(F)(F)F)(Cl)Cl)(Cl)Cl)(F)F MZFMJRBUTDYLCV-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- HKYGSMOFSFOEIP-UHFFFAOYSA-N dichloro(dichloromethoxy)methane Chemical compound ClC(Cl)OC(Cl)Cl HKYGSMOFSFOEIP-UHFFFAOYSA-N 0.000 description 1
- WCRUPGQOANCAPX-UHFFFAOYSA-N dichloromethoxy(trifluoro)methane Chemical compound FC(F)(F)OC(Cl)Cl WCRUPGQOANCAPX-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010980 drying distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229950010045 fluroxene Drugs 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- RFKMCNOHBTXSMU-UHFFFAOYSA-N methoxyflurane Chemical compound COC(F)(F)C(Cl)Cl RFKMCNOHBTXSMU-UHFFFAOYSA-N 0.000 description 1
- 229960002455 methoxyflurane Drugs 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 210000004738 parenchymal cell Anatomy 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053104 | 1967-07-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1643992A1 true DE1643992A1 (de) | 1971-06-09 |
Family
ID=7106003
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671643992 Pending DE1643992A1 (de) | 1967-07-29 | 1967-07-29 | Fluorierte AEther und Verfahren zu ihrer Herstellung |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE718750A (OSRAM) |
| DE (1) | DE1643992A1 (OSRAM) |
| FR (1) | FR1582909A (OSRAM) |
| IT (1) | IT1053689B (OSRAM) |
| NL (1) | NL6810476A (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6149980A (en) * | 1997-09-15 | 2000-11-21 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
-
1967
- 1967-07-29 DE DE19671643992 patent/DE1643992A1/de active Pending
-
1968
- 1968-07-24 NL NL6810476A patent/NL6810476A/xx unknown
- 1968-07-27 IT IT1956268A patent/IT1053689B/it active
- 1968-07-29 BE BE718750D patent/BE718750A/xx unknown
- 1968-07-29 FR FR1582909D patent/FR1582909A/fr not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6149980A (en) * | 1997-09-15 | 2000-11-21 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US6552090B1 (en) | 1997-09-15 | 2003-04-22 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US6653512B1 (en) | 1997-09-15 | 2003-11-25 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US6743262B1 (en) | 1997-09-15 | 2004-06-01 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
| US6953606B2 (en) | 1997-09-15 | 2005-10-11 | 3M Innovative Properties Company | Perfluoroalkyl haloalkyl ethers and compositions and applications thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE718750A (OSRAM) | 1969-01-29 |
| IT1053689B (it) | 1981-10-10 |
| FR1582909A (OSRAM) | 1969-10-10 |
| NL6810476A (OSRAM) | 1969-01-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE662450C (de) | Verfahren zur Herstellung von Fluorverbindungen aliphatischer Kohlenwasserstoffe oder deren Arylderivaten | |
| DE1542985A1 (de) | Verfahren zur Herstellung synthetischer Pyrethroide | |
| DE1101406B (de) | Verfahren zur Herstellung von Thionophosphorsaeureestern | |
| DE1643591C (OSRAM) | ||
| DE2139398B2 (de) | Difluormethyl-1,2,2,33-pentafluorpropyläther, Verfahren zu seiner Herstellung und diesen enthaltendes Anaesthetikum | |
| DE3017154A1 (de) | Verfahren zur herstellung von 2-chlor-1,1,1,2,3,3,3,-heptafluor-propan | |
| DE2215401A1 (de) | Perfluorvinyläther | |
| DE2361058A1 (de) | 1.2.2.2-tetrafluoraethyl-chlorfluormethylaether und verfahren zu dessen herstellung | |
| DE3012005A1 (de) | 2,3-dichlor-2-trifluormethyl-1,1,1,3,4,4,5,5,5-nonafluorpentan und verfahren zu seiner herstellung | |
| DE2340561C2 (de) | 2.2.2-Trifluor-1-chloräthyl-äther und Verfahren zu ihrer Herstellung sowie Inhalations-Anästhetikum, das einen dieser Stoffe enthält | |
| DE1141278B (de) | Verfahren zur Herstellung chlor-substituierter Methylisocyanid-dichloride | |
| DE1768449A1 (de) | alpha,omega-Bis-(fluorperhalogenisopropoxy)-perfluoralkane | |
| DE1593718A1 (de) | Verfahren zur Herstellung von 4,4'-Bis-hydroxyalkylaethern des Stilbens | |
| DE2613003C3 (OSRAM) | ||
| DE1954268B2 (de) | Halogenmethyl-1,1,1333-nexafluor-2-propyläther und Verfahren zu deren Herstellung sowie diese enthaltende Anästhesie-Mittel | |
| DE947304C (de) | Verfahren zur Herstellung von 1, 3, 5-Trichlorbenzol durch Isomerisierung anderer Trichlorbenzole | |
| DE3937567A1 (de) | Verfahren zur herstellung von weitgehend fluorierten alkylbromiden | |
| DE2157400A1 (de) | Anaesthetica | |
| DE2524956A1 (de) | 2-hydro-perfluor-n-propyl-fluormethylaether und verfahren zu seiner herstellung | |
| DE3710631A1 (de) | Trifluormethylbenzoylbromid und dessen umwandlung zu brombenzotrifluorid | |
| DE2111696A1 (de) | Perfluorpolyaether mit cyclischer Struktur und Verfahren zur Herstellung derselben | |
| DE2510157A1 (de) | Halogenierte methylcyclopropylaether, verfahren zur herstellung derselben und anaesthesiemischung | |
| DE2500344A1 (de) | Verbindungen mit einer ungesaettigten aliphatischen kette, verfahren zu deren herstellung sowie insektizid mit juvenilhormonwirkung | |
| DE841151C (de) | Verfahren zur elektrochemischen Herstellung von Fluoramin-verbindungen | |
| EP0461563B1 (de) | Verfahren zur Herstellung von weitgehend fluorierten Alkylbromiden |