DE2531511C2 - Verfahren zur Herstellung von Perfluoräthern - Google Patents
Verfahren zur Herstellung von PerfluoräthernInfo
- Publication number
- DE2531511C2 DE2531511C2 DE2531511A DE2531511A DE2531511C2 DE 2531511 C2 DE2531511 C2 DE 2531511C2 DE 2531511 A DE2531511 A DE 2531511A DE 2531511 A DE2531511 A DE 2531511A DE 2531511 C2 DE2531511 C2 DE 2531511C2
- Authority
- DE
- Germany
- Prior art keywords
- perfluoro
- dimethyl
- mbar
- formula
- hours
- 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 description 14
- 229920001774 Perfluoroether Polymers 0.000 title description 3
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical class FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 title description 3
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 perfluorocarbonyl compounds Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000002170 ethers Chemical class 0.000 claims description 2
- 239000007791 liquid phase Substances 0.000 claims description 2
- 238000009835 boiling Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000002576 ketones Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical group C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002826 coolant Substances 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- WMFABESKCHGSRC-UHFFFAOYSA-N propanoyl fluoride Chemical compound CCC(F)=O WMFABESKCHGSRC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 description 2
- 239000000539 dimer Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002222 fluorine compounds Chemical class 0.000 description 2
- DCAYPVUWAIABOU-UHFFFAOYSA-N hexadecane Chemical compound CCCCCCCCCCCCCCCC DCAYPVUWAIABOU-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 238000005476 soldering Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RRZIJNVZMJUGTK-UHFFFAOYSA-N 1,1,2-trifluoro-2-(1,2,2-trifluoroethenoxy)ethene Chemical class FC(F)=C(F)OC(F)=C(F)F RRZIJNVZMJUGTK-UHFFFAOYSA-N 0.000 description 1
- JXZZRMZMPFHOMZ-UHFFFAOYSA-N 1-ethoxy-2-(2-propoxypropoxy)propane Chemical compound CCCOC(C)COC(C)COCC JXZZRMZMPFHOMZ-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
- PFQHEUJBVHHSTQ-UHFFFAOYSA-N 2,3-dipropoxybutane Chemical compound C(CC)OC(C)C(C)OCCC PFQHEUJBVHHSTQ-UHFFFAOYSA-N 0.000 description 1
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001273 butane Substances 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- IYRWEQXVUNLMAY-UHFFFAOYSA-N carbonyl fluoride Chemical class FC(F)=O IYRWEQXVUNLMAY-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000006324 decarbonylation Effects 0.000 description 1
- 238000006606 decarbonylation reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- WMIYKQLTONQJES-UHFFFAOYSA-N hexafluoroethane Chemical compound FC(F)(F)C(F)(F)F WMIYKQLTONQJES-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical class FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F ZJIJAJXFLBMLCK-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001643 poly(ether ketone) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 210000001215 vagina Anatomy 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/12—1,4-Dioxanes; Hydrogenated 1,4-dioxanes not condensed with other rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2531511A DE2531511C2 (de) | 1975-07-15 | 1975-07-15 | Verfahren zur Herstellung von Perfluoräthern |
| NL7607634A NL7607634A (nl) | 1975-07-15 | 1976-07-09 | Werkwijze voor het bereiden van perfluorethers. |
| US05/704,689 US4052277A (en) | 1975-07-12 | 1976-07-12 | Process for preparing perfluorinated ethers |
| JP51083067A JPS5210209A (en) | 1975-07-15 | 1976-07-14 | Method of producing perfluoroether |
| CA256,966A CA1083587A (en) | 1975-07-15 | 1976-07-14 | Process for preparing perfluorinated ethers |
| GB29532/76A GB1546399A (en) | 1975-07-15 | 1976-07-15 | Process for preparing perfluorinated ethers |
| FR7621602A FR2318137A1 (fr) | 1975-07-15 | 1976-07-15 | Procede de preparation d'ethers perfluores par irradiation lumineuse de perfluoro-cetones |
| BE168937A BE844157A (fr) | 1975-07-15 | 1976-07-15 | Procede de preparation d'ethers perfluores par irradiation lumineuse de perfluoro-cetones |
| US05/791,997 US4118398A (en) | 1975-07-15 | 1977-04-28 | Perfluorinated ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2531511A DE2531511C2 (de) | 1975-07-15 | 1975-07-15 | Verfahren zur Herstellung von Perfluoräthern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2531511A1 DE2531511A1 (de) | 1977-02-03 |
| DE2531511C2 true DE2531511C2 (de) | 1984-03-22 |
Family
ID=5951536
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2531511A Expired DE2531511C2 (de) | 1975-07-12 | 1975-07-15 | Verfahren zur Herstellung von Perfluoräthern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4052277A (enExample) |
| JP (1) | JPS5210209A (enExample) |
| BE (1) | BE844157A (enExample) |
| CA (1) | CA1083587A (enExample) |
| DE (1) | DE2531511C2 (enExample) |
| FR (1) | FR2318137A1 (enExample) |
| GB (1) | GB1546399A (enExample) |
| NL (1) | NL7607634A (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4101446A1 (de) * | 1991-01-17 | 1992-07-23 | Zentralinstitut Fuer Anorganis | Perfluorierte polycycloaliphatische ether und ein verfahren zu ihrer herstellung |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8301506D0 (en) * | 1983-01-20 | 1983-02-23 | Electricity Council | Fluorinated ethers |
| US4975212A (en) * | 1988-12-27 | 1990-12-04 | Allied-Signal Inc. | Fluorinated lubricating compositions |
| US5154846A (en) * | 1988-12-27 | 1992-10-13 | Allied-Signal Inc. | Fluorinated butylene oxide based refrigerant lubricants |
| US5100569A (en) * | 1990-11-30 | 1992-03-31 | Allied-Signal Inc. | Polyoxyalkylene glycol refrigeration lubricants having pendant, non-terminal perfluoroalkyl groups |
| JPH082893B2 (ja) * | 1991-04-16 | 1996-01-17 | 信越化学工業株式会社 | パーフルオロ環状ケトン及びその製造法 |
| US5534176A (en) * | 1991-07-30 | 1996-07-09 | Alliedsignal Inc. | Refrigeration lubricants prepared by polymerizing alkene having a perfluoroalkyl group on one end thereof |
| DE4221555A1 (de) * | 1992-07-01 | 1994-01-05 | Hoechst Ag | Verfahren zur Herstellung von Perfluorpolyethern |
| US8193397B2 (en) * | 2006-12-06 | 2012-06-05 | 3M Innovative Properties Company | Hydrofluoroether compounds and processes for their preparation and use |
| JP6766907B2 (ja) * | 2019-02-12 | 2020-10-14 | ダイキン工業株式会社 | フルオロラクトン及びその製造方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3849504A (en) * | 1967-03-10 | 1974-11-19 | Minnesota Mining & Mfg | Perfluoropolyethers and process for making |
-
1975
- 1975-07-15 DE DE2531511A patent/DE2531511C2/de not_active Expired
-
1976
- 1976-07-09 NL NL7607634A patent/NL7607634A/xx not_active Application Discontinuation
- 1976-07-12 US US05/704,689 patent/US4052277A/en not_active Expired - Lifetime
- 1976-07-14 JP JP51083067A patent/JPS5210209A/ja active Pending
- 1976-07-14 CA CA256,966A patent/CA1083587A/en not_active Expired
- 1976-07-15 FR FR7621602A patent/FR2318137A1/fr active Granted
- 1976-07-15 GB GB29532/76A patent/GB1546399A/en not_active Expired
- 1976-07-15 BE BE168937A patent/BE844157A/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4101446A1 (de) * | 1991-01-17 | 1992-07-23 | Zentralinstitut Fuer Anorganis | Perfluorierte polycycloaliphatische ether und ein verfahren zu ihrer herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2318137B1 (enExample) | 1982-04-02 |
| BE844157A (fr) | 1977-01-17 |
| CA1083587A (en) | 1980-08-12 |
| US4052277A (en) | 1977-10-04 |
| FR2318137A1 (fr) | 1977-02-11 |
| GB1546399A (en) | 1979-05-23 |
| NL7607634A (nl) | 1977-01-18 |
| DE2531511A1 (de) | 1977-02-03 |
| JPS5210209A (en) | 1977-01-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2147102C3 (de) | Verfahren zur Herstellung von difunktionellen fluorhaltigen Polymeren | |
| DE69229359T2 (de) | HERSTELLUNG VON FLUORKOHLENWASSERSTOFFEN AUS alpha-FLUORETHERN UND EINIGEN alpha-FLUORETHERN | |
| DE2531511C2 (de) | Verfahren zur Herstellung von Perfluoräthern | |
| DE2145174A1 (de) | alpha, omega-Di-s-triazinylperfluorpolyoxaalkane | |
| EP0355025A2 (de) | Substituierte(2-Haloalkoxy-1.1.2-trifluoräthoxy)-styrole, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE69708544T2 (de) | Verfahren zur herstellung von fluoromethyl-(1,1,1,3,3,3)-hexafluoroisopropylether | |
| DE2521594C2 (de) | Verfahren zur Herstellung perfluorierter Ketone | |
| DE3032471C2 (enExample) | ||
| DE2627986C2 (de) | Verfahren zur Herstellung von Perfluoralkoxypropionsäurefluoriden | |
| DE2461445C2 (de) | Verfahren zur Herstellung von Perfluor-α-alkoxypropionsäurefluoriden | |
| DE2451493C2 (de) | Verfahren zur Herstellung von perfluorierten Äthern | |
| EP0228701B1 (de) | 2-Iod-perfluor-2-methylalkane, Verfahren zu deren Herstellung und deren Verwendung | |
| DE1593229A1 (de) | Perfluorivinylaether und Verfahren zu ihrer Herstellung | |
| DE2614333C2 (de) | Verfahren zur Herstellung von perfluorierten Äthercarbonsäurefluoriden durch katalytische Umsetzung von Hexafluorpropylenepoxid mit Ketonen oder Säurefluoriden | |
| US4118398A (en) | Perfluorinated ethers | |
| DE2434992C2 (de) | Verfahren zur Herstellung von Perfluor-α-[3,6-dimethyl-1,4-dioxanyl-2-oxy]-propionylfluorid | |
| DE1768449A1 (de) | alpha,omega-Bis-(fluorperhalogenisopropoxy)-perfluoralkane | |
| DE69206002T2 (de) | Perfluorinierte cyclische Hemiketale, entsprechende Perfluorodiketone und Verfahren zu ihrer Herstellung. | |
| DE1593023A1 (de) | Verfahren zur Herstellung organischer fluorierter Verbindungen | |
| DE2517357A1 (de) | Perfluorvinylaether | |
| EP0521347A1 (de) | Verfahren zur Herstellung von perfluorierten Ethern | |
| DE69302783T2 (de) | Verfahren zur Herstellung von Perfluor-2-Methyl-4-Methoxypentan | |
| DE2318786C3 (de) | Verfahren zur Herstellung von γ-Aryloxyacetessigestern | |
| DE1252650B (de) | I Verfahren zur Herstellung von w asserstoffmodifizierten Fluorkohlenstoff polyathern | |
| DE2461675C3 (de) | Verfahren zur Herstellung von die Fluorsulfonylgruppe enthaltenden Perfluoralkylvinyläthem |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |