CA1087618A - Process for preparing perfluoro-4-oxo-2,5-dimethyl-2- fluorocarbonyl-1,3-dioxolane - Google Patents
Process for preparing perfluoro-4-oxo-2,5-dimethyl-2- fluorocarbonyl-1,3-dioxolaneInfo
- Publication number
- CA1087618A CA1087618A CA278,949A CA278949A CA1087618A CA 1087618 A CA1087618 A CA 1087618A CA 278949 A CA278949 A CA 278949A CA 1087618 A CA1087618 A CA 1087618A
- Authority
- CA
- Canada
- Prior art keywords
- dioxolane
- dimethyl
- oxo
- perfluoro
- fluorocarbonyl
- 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
- 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 title claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 4
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims abstract 2
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 12
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 6
- 125000004429 atom Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 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
- 238000000034 method Methods 0.000 description 5
- 150000003335 secondary amines Chemical class 0.000 description 5
- 238000001816 cooling Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 150000004862 dioxolanes Chemical class 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 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
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004508 fractional distillation Methods 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
- 239000011541 reaction mixture Substances 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000010626 work up procedure Methods 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
- GVDJEHMDNREMFA-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanoic acid Chemical compound OC(=O)C(=O)C(F)(F)F GVDJEHMDNREMFA-UHFFFAOYSA-N 0.000 description 1
- NSODUNDFRPXDAR-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanoyl fluoride Chemical compound FC(=O)C(=O)C(F)(F)F NSODUNDFRPXDAR-UHFFFAOYSA-N 0.000 description 1
- GXYSGXQCYCTENJ-UHFFFAOYSA-N 4-(difluoromethyl)morpholine Chemical compound FC(F)N1CCOCC1 GXYSGXQCYCTENJ-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 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
- 238000007700 distillative separation Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- CBLGQEBXWDKYDI-UHFFFAOYSA-N piperazine-1,4-dicarbaldehyde Chemical compound O=CN1CCN(C=O)CC1 CBLGQEBXWDKYDI-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- -1 polymethylene Polymers 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
- 230000036632 reaction speed Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 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
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 238000003786 synthesis reaction 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2623089.7 | 1976-05-22 | ||
| 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 |
|---|---|
| CA1087618A true CA1087618A (en) | 1980-10-14 |
Family
ID=5978792
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA278,949A Expired CA1087618A (en) | 1976-05-22 | 1977-05-20 | Process for preparing perfluoro-4-oxo-2,5-dimethyl-2- fluorocarbonyl-1,3-dioxolane |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS52142072A (OSRAM) |
| BE (1) | BE854912A (OSRAM) |
| CA (1) | CA1087618A (OSRAM) |
| DE (1) | DE2623089A1 (OSRAM) |
| FR (1) | FR2351975A1 (OSRAM) |
| GB (1) | GB1560842A (OSRAM) |
| IT (1) | IT1074841B (OSRAM) |
| NL (1) | NL7705444A (OSRAM) |
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 |
|---|---|
| GB1560842A (en) | 1980-02-13 |
| BE854912A (fr) | 1977-11-23 |
| FR2351975B1 (OSRAM) | 1982-10-22 |
| FR2351975A1 (fr) | 1977-12-16 |
| IT1074841B (it) | 1985-04-20 |
| DE2623089A1 (de) | 1977-12-08 |
| NL7705444A (nl) | 1977-11-24 |
| JPS52142072A (en) | 1977-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |