DE60209436T2 - Alkyl Ester der 2-(2-Fluorosulfonyl)-perfluoroethylenoxy-3-halogen-Propionsäure - Google Patents
Alkyl Ester der 2-(2-Fluorosulfonyl)-perfluoroethylenoxy-3-halogen-Propionsäure Download PDFInfo
- Publication number
- DE60209436T2 DE60209436T2 DE60209436T DE60209436T DE60209436T2 DE 60209436 T2 DE60209436 T2 DE 60209436T2 DE 60209436 T DE60209436 T DE 60209436T DE 60209436 T DE60209436 T DE 60209436T DE 60209436 T2 DE60209436 T2 DE 60209436T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- compound
- reaction
- acyl fluoride
- carried out
- 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 - Lifetime
Links
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 title description 3
- 125000005907 alkyl ester group Chemical group 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 150000001265 acyl fluorides Chemical class 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 238000003682 fluorination reaction Methods 0.000 claims description 9
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 238000007127 saponification reaction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 238000005979 thermal decomposition reaction Methods 0.000 claims description 4
- -1 alkali metal cation Chemical class 0.000 claims description 3
- 229910052792 caesium Inorganic materials 0.000 claims description 3
- 238000004821 distillation Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052709 silver Inorganic materials 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001350 alkyl halides Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 4
- 238000000605 extraction Methods 0.000 claims 2
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 13
- 229910006095 SO2F Inorganic materials 0.000 description 6
- GANXFQTZEVGPPI-UHFFFAOYSA-N fluorosulfonyloxyethene Chemical compound FS(=O)(=O)OC=C GANXFQTZEVGPPI-UHFFFAOYSA-N 0.000 description 6
- LRGIIZXVSULULZ-UHFFFAOYSA-N 2,3-dichloro-2-methylpropanoic acid Chemical compound ClCC(Cl)(C)C(O)=O LRGIIZXVSULULZ-UHFFFAOYSA-N 0.000 description 3
- VMUWIFNDNXXSQA-UHFFFAOYSA-N hypofluorite Chemical compound F[O-] VMUWIFNDNXXSQA-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- UPVJEODAZWTJKZ-OWOJBTEDSA-N (e)-1,2-dichloro-1,2-difluoroethene Chemical group F\C(Cl)=C(\F)Cl UPVJEODAZWTJKZ-OWOJBTEDSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006298 dechlorination reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229960004624 perflexane Drugs 0.000 description 1
- ZJIJAJXFLBMLCK-UHFFFAOYSA-N perfluorohexane Chemical compound 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
- 239000012071 phase Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000197 pyrolysis 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
- 239000000376 reactant Substances 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 229940096017 silver fluoride Drugs 0.000 description 1
- REYHXKZHIMGNSE-UHFFFAOYSA-M silver monofluoride Chemical compound [F-].[Ag+] REYHXKZHIMGNSE-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
- C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITMI20020001 | 2002-01-03 | ||
| IT2002MI000001A ITMI20020001A1 (it) | 2002-01-03 | 2002-01-03 | Esteri alchilici dell'acido 2-(2-fluorosulfoni l) perfluoretilenossi 3 alogeno propionico |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60209436D1 DE60209436D1 (de) | 2006-04-27 |
| DE60209436T2 true DE60209436T2 (de) | 2006-10-26 |
Family
ID=11448775
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60209436T Expired - Lifetime DE60209436T2 (de) | 2002-01-03 | 2002-12-20 | Alkyl Ester der 2-(2-Fluorosulfonyl)-perfluoroethylenoxy-3-halogen-Propionsäure |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US6703521B2 (OSRAM) |
| EP (1) | EP1325906B1 (OSRAM) |
| JP (1) | JP4324373B2 (OSRAM) |
| DE (1) | DE60209436T2 (OSRAM) |
| IT (1) | ITMI20020001A1 (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007142266A1 (ja) * | 2006-06-07 | 2007-12-13 | Daikin Industries, Ltd. | 含フッ素フルオロスルホニルアルキルビニルエーテルの製造方法 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2713593A (en) | 1953-12-21 | 1955-07-19 | Minnesota Mining & Mfg | Fluorocarbon acids and derivatives |
| US4275226A (en) * | 1978-08-25 | 1981-06-23 | Asahi Glass Company, Ltd. | Process for producing fluorovinyl ether |
| US4337211A (en) * | 1980-06-11 | 1982-06-29 | The Dow Chemical Company | Fluorocarbon ethers having substituted halogen site(s) and process to prepare |
| US4358412A (en) * | 1980-06-11 | 1982-11-09 | The Dow Chemical Company | Preparation of vinyl ethers |
| IT1197476B (it) | 1986-09-10 | 1988-11-30 | Ausimont Spa | Ipofluoriti e bis-ipofluoriti e procedimento per la loro preparazione |
| IT1230718B (it) * | 1989-02-13 | 1991-10-29 | Ausimont Srl | Fluorurazione diretta di fluoro b sultoni ai corrispondenti fluorossi fluorosulfonil fluorocomposti. |
| US5488142A (en) | 1993-10-04 | 1996-01-30 | Minnesota Mining And Manufacturing Company | Fluorination in tubular reactor system |
| DE69738168T2 (de) | 1997-05-02 | 2008-06-26 | Minnesota Mining & Manufacturing Company, St. Paul | Elektrochemische fluorierung mit unterbrochenem strom |
| US6388139B1 (en) * | 1997-11-05 | 2002-05-14 | E. I. Du Pont De Nemours And Company | Production of perfluoro (alkyl vinyl) ethers |
| JP2001114750A (ja) * | 1999-10-19 | 2001-04-24 | Daikin Ind Ltd | パーフルオロビニルエーテルスルホン酸誘導体の製造法 |
-
2002
- 2002-01-03 IT IT2002MI000001A patent/ITMI20020001A1/it unknown
- 2002-12-20 EP EP02028583A patent/EP1325906B1/en not_active Expired - Lifetime
- 2002-12-20 DE DE60209436T patent/DE60209436T2/de not_active Expired - Lifetime
- 2002-12-25 JP JP2002375126A patent/JP4324373B2/ja not_active Expired - Lifetime
- 2002-12-27 US US10/329,710 patent/US6703521B2/en not_active Expired - Lifetime
-
2004
- 2004-02-05 US US10/771,313 patent/US6949676B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1325906A1 (en) | 2003-07-09 |
| US6949676B2 (en) | 2005-09-27 |
| DE60209436D1 (de) | 2006-04-27 |
| ITMI20020001A0 (it) | 2002-01-03 |
| US20040158099A1 (en) | 2004-08-12 |
| US6703521B2 (en) | 2004-03-09 |
| JP2003221378A (ja) | 2003-08-05 |
| US20030125582A1 (en) | 2003-07-03 |
| JP4324373B2 (ja) | 2009-09-02 |
| ITMI20020001A1 (it) | 2003-07-03 |
| EP1325906B1 (en) | 2006-03-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: PFENNING MEINIG & PARTNER GBR, 80339 MUENCHEN |
|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: MAIWALD PATENTANWALTSGESELLSCHAFT MBH, 80335 MUENC |