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 (OSRAM) | 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 (OSRAM) |
| JP (1) | JPS52142078A (OSRAM) |
| BE (1) | BE854913A (OSRAM) |
| CA (1) | CA1084515A (OSRAM) |
| DE (1) | DE2623090A1 (OSRAM) |
| FR (1) | FR2351976A1 (OSRAM) |
| GB (1) | GB1560843A (OSRAM) |
| IT (1) | IT1074831B (OSRAM) |
| NL (1) | NL7705442A (OSRAM) |
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 |
| WO2022244715A1 (ja) | 2021-05-17 | 2022-11-24 | 東ソ－株式会社 | １，４－ジオキサン誘導体の製造方法、１，４－ジオキサン誘導体及び１，４－ジオキサン誘導体を含有する組成物並びに（１，３－ジオキソラン）－２－カルボン酸誘導体の製造方法、（１，３－ジオキソラン）－２－カルボン酸誘導体及び（１，３－ジオキソラン）－２－カルボン酸誘導体を含有する組成物 |
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 |
| US3450716A (en) * | 1966-05-26 | 1969-06-17 | Du Pont | Perfluoro-4-oxo-2,5-dimethyl-2-fluorocarbonyl-1,3-dioxolane |
| US3404162A (en) * | 1966-05-26 | 1968-10-01 | Du Pont | Perfluoro-2-oxo-3, 6-dimethyl-1, 4-dioxane |
| 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 GB GB21309/77A patent/GB1560843A/en not_active Expired
- 1977-05-20 IT IT23843/77A patent/IT1074831B/it active
- 1977-05-20 CA CA278,874A patent/CA1084515A/en not_active Expired
- 1977-05-23 FR FR7715681A patent/FR2351976A1/fr active Granted
- 1977-05-23 BE BE177805A patent/BE854913A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DE2623090C2 (OSRAM) | 1988-05-05 |
| FR2351976A1 (fr) | 1977-12-16 |
| JPS52142078A (en) | 1977-11-26 |
| GB1560843A (en) | 1980-02-13 |
| FR2351976B1 (OSRAM) | 1981-07-10 |
| US4118399A (en) | 1978-10-03 |
| CA1084515A (en) | 1980-08-26 |
| BE854913A (fr) | 1977-11-23 |
| NL7705442A (nl) | 1977-11-24 |
| IT1074831B (it) | 1985-04-20 |
| DE2623090A1 (de) | 1977-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2271356C2 (ru) | Виниленкарбонатная смесь и способ ее получения | |
| US3450716A (en) | Perfluoro-4-oxo-2,5-dimethyl-2-fluorocarbonyl-1,3-dioxolane | |
| US4335255A (en) | Alkyl perfluoro (2-methyl-5-oxo-3-oxahexanoate) | |
| US3321517A (en) | Perfluoropyruvyl fluoride and process | |
| JP2023103409A (ja) | モノチオカーボネート化合物の製造方法 | |
| US4067884A (en) | Fluorine containing ketones | |
| US3475456A (en) | Perfluoro-2,4-dimethyl-2-fluorocarbonyl-1,3-dioxolane | |
| EP0301881A1 (en) | Halogenated 1,3-dioxolanes and derivatives | |
| US4118399A (en) | Process for preparing perfluoro-α-(3,6-dimethyl-1,4-dioxanyl-2-oxy)-propionic acid fluoride | |
| JP2609480B2 (ja) | α―フルオロアクリロイル誘導体の製造方法 | |
| JPH059416B2 (OSRAM) | ||
| US3404162A (en) | Perfluoro-2-oxo-3, 6-dimethyl-1, 4-dioxane | |
| JP5251875B2 (ja) | フルオロアミドおよびフルオロニトリルの製造方法 | |
| JPS5935379B2 (ja) | ヘキサフルオルプロピレンエポキシドとケトン又は酸フルオリドとの接触反応法 | |
| JPS6121476B2 (OSRAM) | ||
| JPH0212952B2 (OSRAM) | ||
| US5023362A (en) | Alkyl perfluoro(2-methyl-5-oxo-3-oxahexanoate) | |
| GB1560842A (en) | Process for preparing perfluoro - 4 - oxo - 2,5 - dimethyl - 2 - fluorocarbonyl - 1,3 - dioxolane | |
| TW202440531A (zh) | 製備n-經取代-2-噁唑烷酮之方法 | |
| US3467702A (en) | Method for making perfluoropyruvic acid mono-hydrate | |
| JP3731925B2 (ja) | モノビニルエーテルの製法 | |
| US3127450A (en) | Process for the preparation of ketals | |
| JP5267632B2 (ja) | フッ素化（ポリ）エーテル含有カルボニルフルオリドの製造方法 | |
| SU606313A1 (ru) | Способ получени замещенных 5-метилен-1,3-диоксолан-4-онов | |
| US4786442A (en) | Alkyl perfluoro(2-methyl-5-oxo-3-oxahexanoate) |