JPS6120552B2 - - Google Patents
Info
- Publication number
- JPS6120552B2 JPS6120552B2 JP52057785A JP5778577A JPS6120552B2 JP S6120552 B2 JPS6120552 B2 JP S6120552B2 JP 52057785 A JP52057785 A JP 52057785A JP 5778577 A JP5778577 A JP 5778577A JP S6120552 B2 JPS6120552 B2 JP S6120552B2
- Authority
- JP
- Japan
- Prior art keywords
- perfluoro
- amine
- dimethyl
- hfpo
- compound
- 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
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 11
- 150000003335 secondary amines Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- CWRPQPNYDDMAMA-UHFFFAOYSA-N 3,5,5,6-tetrafluoro-3,6-bis(trifluoromethyl)-1,4-dioxan-2-one Chemical compound FC(F)(F)C1(F)OC(F)(F)C(F)(C(F)(F)F)OC1=O CWRPQPNYDDMAMA-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
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZUHZGEOKBKGPSW-UHFFFAOYSA-N tetraglyme Chemical compound COCCOCCOCCOCCOC ZUHZGEOKBKGPSW-UHFFFAOYSA-N 0.000 description 4
- 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 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- -1 hydroxy, carboxy Chemical group 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- 238000009835 boiling Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 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
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- VGYLMOJQAHXYCK-UHFFFAOYSA-N 1-methylimidazolidine Chemical compound CN1CCNC1 VGYLMOJQAHXYCK-UHFFFAOYSA-N 0.000 description 1
- HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 1
- GCGMKVVEPSFPFS-UHFFFAOYSA-N 3,3,3-trifluoro-2-oxopropanoic acid hydrofluoride Chemical compound F.OC(=O)C(=O)C(F)(F)F GCGMKVVEPSFPFS-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 150000004862 dioxolanes Chemical class 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 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
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GDSGXRQXKTWBOS-UHFFFAOYSA-N n,n-di(tridecyl)tridecan-1-amine Chemical compound CCCCCCCCCCCCCN(CCCCCCCCCCCCC)CCCCCCCCCCCCC GDSGXRQXKTWBOS-UHFFFAOYSA-N 0.000 description 1
- ZCPYWQFSAALXCQ-UHFFFAOYSA-N n-[bis(dimethylamino)-difluoro-$l^{5}-phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(F)(F)(N(C)C)N(C)C ZCPYWQFSAALXCQ-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 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
- 229920000642 polymer Polymers 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762623090 DE2623090A1 (de) | 1976-05-22 | 1976-05-22 | Verfahren zur herstellung von perfluor-alpha- (3,6-dimethyl-1,4- dioxanyl-2-oxy)-propionsaeurefluorid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52142078A JPS52142078A (en) | 1977-11-26 |
| JPS6120552B2 true JPS6120552B2 (enExample) | 1986-05-22 |
Family
ID=5978794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5778577A Granted JPS52142078A (en) | 1976-05-22 | 1977-05-20 | Production of perfluorooalphaa*3*66dimethyll1*44 dioxanyll22oxy**propionic acid fluoride |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4118399A (enExample) |
| JP (1) | JPS52142078A (enExample) |
| BE (1) | BE854913A (enExample) |
| CA (1) | CA1084515A (enExample) |
| DE (1) | DE2623090A1 (enExample) |
| FR (1) | FR2351976A1 (enExample) |
| GB (1) | GB1560843A (enExample) |
| IT (1) | IT1074831B (enExample) |
| NL (1) | NL7705442A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2623089A1 (de) * | 1976-05-22 | 1977-12-08 | Hoechst Ag | Verfahren zur herstellung von perfluor-4-oxo-2,5-dimethyl-2-fluorcarbonyl-1,3-dioxolan |
| DE2928602A1 (de) * | 1979-07-14 | 1981-02-05 | Hoechst Ag | Verfahren zur herstellung von 2.3- perfluor-1.4-dioxanen sowie einige spezielle vertreter dieser verbindungsklasse |
| JPS58131935A (ja) * | 1982-12-29 | 1983-08-06 | Daikin Ind Ltd | 光学分割用試薬 |
| US8791254B2 (en) * | 2006-05-19 | 2014-07-29 | 3M Innovative Properties Company | Cyclic 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 |
| EP3971173A4 (en) * | 2019-05-13 | 2023-03-22 | Daikin Industries, Ltd. | FLUOROLACTONE AND METHOD FOR PRODUCTION |
| JPWO2022244715A1 (enExample) | 2021-05-17 | 2022-11-24 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3308107A (en) * | 1965-04-30 | 1967-03-07 | Du Pont | Perfluoro(2-methylene-4-methyl-1, 3-dioxolane) and polymers thereof |
| US3404162A (en) * | 1966-05-26 | 1968-10-01 | Du Pont | Perfluoro-2-oxo-3, 6-dimethyl-1, 4-dioxane |
| US3450716A (en) * | 1966-05-26 | 1969-06-17 | Du Pont | Perfluoro-4-oxo-2,5-dimethyl-2-fluorocarbonyl-1,3-dioxolane |
| DE2434992C2 (de) * | 1974-07-20 | 1985-11-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Perfluor-α-[3,6-dimethyl-1,4-dioxanyl-2-oxy]-propionylfluorid |
| DE2461445C2 (de) * | 1974-12-24 | 1984-06-28 | Hoechst Ag, 6230 Frankfurt | Verfahren zur Herstellung von Perfluor-α-alkoxypropionsäurefluoriden |
| US3962279A (en) * | 1975-06-06 | 1976-06-08 | E. I. Du Pont De Nemours And Company | Synthesis of perfluoropyruvyl fluoride dimer |
| DE2544040C2 (de) * | 1975-10-02 | 1981-09-24 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von modifizierten Tetrafluoräthylen-Dispersionspolymerisaten |
-
1976
- 1976-05-22 DE DE19762623090 patent/DE2623090A1/de active Granted
-
1977
- 1977-05-17 NL NL7705442A patent/NL7705442A/xx not_active Application Discontinuation
- 1977-05-19 US US05/798,311 patent/US4118399A/en not_active Expired - Lifetime
- 1977-05-20 JP JP5778577A patent/JPS52142078A/ja active Granted
- 1977-05-20 IT IT23843/77A patent/IT1074831B/it active
- 1977-05-20 GB GB21309/77A patent/GB1560843A/en not_active Expired
- 1977-05-20 CA CA278,874A patent/CA1084515A/en not_active Expired
- 1977-05-23 BE BE177805A patent/BE854913A/xx not_active IP Right Cessation
- 1977-05-23 FR FR7715681A patent/FR2351976A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| NL7705442A (nl) | 1977-11-24 |
| DE2623090A1 (de) | 1977-12-08 |
| CA1084515A (en) | 1980-08-26 |
| JPS52142078A (en) | 1977-11-26 |
| BE854913A (fr) | 1977-11-23 |
| GB1560843A (en) | 1980-02-13 |
| FR2351976B1 (enExample) | 1981-07-10 |
| DE2623090C2 (enExample) | 1988-05-05 |
| US4118399A (en) | 1978-10-03 |
| FR2351976A1 (fr) | 1977-12-16 |
| IT1074831B (it) | 1985-04-20 |
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