DE2623089A1 - Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan - Google Patents
Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolanInfo
- Publication number
- DE2623089A1 DE2623089A1 DE19762623089 DE2623089A DE2623089A1 DE 2623089 A1 DE2623089 A1 DE 2623089A1 DE 19762623089 DE19762623089 DE 19762623089 DE 2623089 A DE2623089 A DE 2623089A DE 2623089 A1 DE2623089 A1 DE 2623089A1
- Authority
- DE
- Germany
- Prior art keywords
- dioxolane
- oxo
- fluorocarbonyl
- dimethyl
- preparation
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 10
- 238000002360 preparation method Methods 0.000 title description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 17
- -1 hexafluoropropane epoxide Chemical class 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 8
- 150000003335 secondary amines Chemical class 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 150000004862 dioxolanes Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000013459 approach Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000011698 potassium fluoride Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- AGRIQBHIKABLPJ-UHFFFAOYSA-N 1-Pyrrolidinecarboxaldehyde Chemical compound O=CN1CCCC1 AGRIQBHIKABLPJ-UHFFFAOYSA-N 0.000 description 1
- NVLMRLQANVCTOG-UHFFFAOYSA-N 4-fluoro-5-oxo-2,4-bis(trifluoromethyl)-1,3-dioxolane-2-carbonyl fluoride Chemical compound FC(=O)C1(C(F)(F)F)OC(=O)C(F)(C(F)(F)F)O1 NVLMRLQANVCTOG-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- PZFYOFFTIYJCEW-UHFFFAOYSA-N n-tridecyltridecan-1-amine Chemical compound CCCCCCCCCCCCCNCCCCCCCCCCCCC PZFYOFFTIYJCEW-UHFFFAOYSA-N 0.000 description 1
- HFHZKZSRXITVMK-UHFFFAOYSA-N oxyphenbutazone Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=C(O)C=C1 HFHZKZSRXITVMK-UHFFFAOYSA-N 0.000 description 1
- 229960000649 oxyphenbutazone Drugs 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/067—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents attached to the same carbon chain, which is not interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/42—Halogen atoms or nitro radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762623089 DE2623089A1 (de) | 1976-05-22 | 1976-05-22 | Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan |
| NL7705444A NL7705444A (nl) | 1976-05-22 | 1977-05-17 | Werkwijze voor de bereiding van perfluor-4-oxo- -2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan. |
| IT2384477A IT1074841B (it) | 1976-05-22 | 1977-05-20 | Processo per la preparazione di perfluoro-4-osso-2,5-dimetil-2-fluorocarbonil-1,3-diossolano. |
| GB2130877A GB1560842A (en) | 1976-05-22 | 1977-05-20 | Process for preparing perfluoro - 4 - oxo - 2,5 - dimethyl - 2 - fluorocarbonyl - 1,3 - dioxolane |
| JP5778677A JPS52142072A (en) | 1976-05-22 | 1977-05-20 | Preparation of perfluoroo44oxoo2*55dimethyll 22fluorocarbonyll1*33dioxolan |
| CA278,949A CA1087618A (en) | 1976-05-22 | 1977-05-20 | Process for preparing perfluoro-4-oxo-2,5-dimethyl-2- fluorocarbonyl-1,3-dioxolane |
| FR7715680A FR2351975A1 (fr) | 1976-05-22 | 1977-05-23 | Procede de preparation d'un dioxolanne substitue perfluore |
| BE177804A BE854912A (fr) | 1976-05-22 | 1977-05-23 | Procede de preparation d'un dioxolanne substitue perfluore |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762623089 DE2623089A1 (de) | 1976-05-22 | 1976-05-22 | Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2623089A1 true DE2623089A1 (de) | 1977-12-08 |
Family
ID=5978792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762623089 Withdrawn DE2623089A1 (de) | 1976-05-22 | 1976-05-22 | Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS52142072A (enExample) |
| BE (1) | BE854912A (enExample) |
| CA (1) | CA1087618A (enExample) |
| DE (1) | DE2623089A1 (enExample) |
| FR (1) | FR2351975A1 (enExample) |
| GB (1) | GB1560842A (enExample) |
| IT (1) | IT1074841B (enExample) |
| NL (1) | NL7705444A (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP7307587B2 (ja) * | 2018-09-03 | 2023-07-12 | 東ソー株式会社 | ヘキサフルオロプロピレンオキシドへのアルデヒド類付加体、およびトリフルオロピルビン酸フルオリドダイマーの製造方法 |
| US11555024B2 (en) | 2018-09-03 | 2023-01-17 | Tosoh Corporation | Aldehyde adduct of hexafluoropropylene oxide, method of manufacturing trifluoropyruvyl fluoride dimer and method of manufacturing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) |
| EP3848359B1 (en) * | 2018-09-03 | 2024-06-12 | Tosoh Corporation | Method for producing trifluoropyruvate fluoride dimer, and method for producing perfluoro(2,4-dimethyl-2-fluoroformyl-1,3-dioxolane) |
| JP7307586B2 (ja) * | 2019-04-26 | 2023-07-12 | 東ソー株式会社 | パーフルオロ（２，４－ジメチル－２－フルオロホルミル－１，３－ジオキソラン）の製造方法 |
| CN114555576A (zh) * | 2019-10-04 | 2022-05-27 | 公益财团法人相模中央化学研究所 | 全氟(2,4-二甲基-2-氟甲酰基-1,3-二氧戊环)的制造方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1422169A (fr) * | 1964-10-21 | 1965-12-24 | Du Pont | Produits perfluorohydrocarbures |
| US3962279A (en) * | 1975-06-06 | 1976-06-08 | E. I. Du Pont De Nemours And Company | Synthesis of perfluoropyruvyl fluoride dimer |
| DE2623090A1 (de) * | 1976-05-22 | 1977-12-08 | Hoechst Ag | Verfahren zur herstellung von perfluor-alpha- (3,6-dimethyl-1,4- dioxanyl-2-oxy)-propionsaeurefluorid |
-
1976
- 1976-05-22 DE DE19762623089 patent/DE2623089A1/de not_active Withdrawn
-
1977
- 1977-05-17 NL NL7705444A patent/NL7705444A/xx not_active Application Discontinuation
- 1977-05-20 CA CA278,949A patent/CA1087618A/en not_active Expired
- 1977-05-20 GB GB2130877A patent/GB1560842A/en not_active Expired
- 1977-05-20 JP JP5778677A patent/JPS52142072A/ja active Pending
- 1977-05-20 IT IT2384477A patent/IT1074841B/it active
- 1977-05-23 FR FR7715680A patent/FR2351975A1/fr active Granted
- 1977-05-23 BE BE177804A patent/BE854912A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1087618A (en) | 1980-10-14 |
| GB1560842A (en) | 1980-02-13 |
| BE854912A (fr) | 1977-11-23 |
| FR2351975B1 (enExample) | 1982-10-22 |
| FR2351975A1 (fr) | 1977-12-16 |
| IT1074841B (it) | 1985-04-20 |
| NL7705444A (nl) | 1977-11-24 |
| JPS52142072A (en) | 1977-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |