DE2029556A1 - Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathern - Google Patents
Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathernInfo
- Publication number
- DE2029556A1 DE2029556A1 DE19702029556 DE2029556A DE2029556A1 DE 2029556 A1 DE2029556 A1 DE 2029556A1 DE 19702029556 DE19702029556 DE 19702029556 DE 2029556 A DE2029556 A DE 2029556A DE 2029556 A1 DE2029556 A1 DE 2029556A1
- Authority
- DE
- Germany
- Prior art keywords
- phenol
- tetrafluoroethylene
- solvent
- reaction
- mol
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 aryl 1,1,2,2 tetrafluoroethyl ethers Chemical class 0.000 title description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 48
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 34
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 18
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241000158147 Sator Species 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 2
- GRDIVJPQARIBNZ-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethoxybenzene Chemical compound FC(F)C(F)(F)OC1=CC=CC=C1 GRDIVJPQARIBNZ-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- 102100021866 Hepatocyte growth factor Human genes 0.000 description 1
- 101000898034 Homo sapiens Hepatocyte growth factor Proteins 0.000 description 1
- 101001081314 Oryctolagus cuniculus Heptapoietin A light chain Proteins 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 150000004707 phenolate Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029556 DE2029556A1 (de) | 1970-06-16 | 1970-06-16 | Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathern |
| NL717108043A NL147122B (nl) | 1970-06-16 | 1971-06-11 | Werkwijze voor het bereiden van aryl-1,1,2,2-tetrafluorethylethers. |
| CH852171A CH551933A (de) | 1970-06-16 | 1971-06-11 | Verfahren zur herstellung von aryl-1,1,2,2-tetrafluoraethylaethern. |
| US152600A US3926989A (en) | 1970-06-16 | 1971-06-14 | Process for the preparation of aryl-1,1,2,2-tetrafluoroethyl ethers |
| BE768485A BE768485A (fr) | 1970-06-16 | 1971-06-14 | Procede de preparation d'aryloxy-1,1,2,2-tetrafluoro-ethanes |
| CA115,662A CA1083156A (en) | 1970-06-16 | 1971-06-15 | Process for the preparation of aryl-1,1,2,2- tetrafluoroethyl ethers |
| FR7121646A FR2096336A5 (enExample) | 1970-06-16 | 1971-06-15 | |
| GB2820271A GB1320648A (en) | 1970-06-16 | 1971-06-16 | Process for the preparation of aryl-1,1,2,2,-tetrafluoroethyl ethers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702029556 DE2029556A1 (de) | 1970-06-16 | 1970-06-16 | Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2029556A1 true DE2029556A1 (de) | 1971-12-23 |
Family
ID=5774046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702029556 Pending DE2029556A1 (de) | 1970-06-16 | 1970-06-16 | Verfahren zur Herstellung von Aryl 1,1,2,2 tetrafluorathylathern |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3926989A (enExample) |
| BE (1) | BE768485A (enExample) |
| CA (1) | CA1083156A (enExample) |
| CH (1) | CH551933A (enExample) |
| DE (1) | DE2029556A1 (enExample) |
| FR (1) | FR2096336A5 (enExample) |
| GB (1) | GB1320648A (enExample) |
| NL (1) | NL147122B (enExample) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8062553B2 (en) | 2006-12-28 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Compositions of polyaniline made with perfuoropolymeric acid which are heat-enhanced and electronic devices made therewith |
| US8153029B2 (en) | 2006-12-28 | 2012-04-10 | E.I. Du Pont De Nemours And Company | Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof |
| US8318046B2 (en) | 2002-09-24 | 2012-11-27 | E I Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| US8409476B2 (en) | 2005-06-28 | 2013-04-02 | E I Du Pont De Nemours And Company | High work function transparent conductors |
| US8491819B2 (en) | 2006-12-29 | 2013-07-23 | E I Du Pont De Nemours And Company | High work-function and high conductivity compositions of electrically conducting polymers |
| US8585931B2 (en) | 2002-09-24 | 2013-11-19 | E I Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US8641926B2 (en) | 2003-04-22 | 2014-02-04 | E I Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US8765022B2 (en) | 2004-03-17 | 2014-07-01 | E I Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL61776A (en) * | 1980-01-08 | 1984-05-31 | Lilly Co Eli | N-(nitrophenyl)-polyfluoroethoxy-benzenamines,their preparation,fungicidal and anticoccidial methods using them |
| US4423249A (en) * | 1981-08-26 | 1983-12-27 | The Dow Chemical Company | Preparation of halofluoroalkyl ethers |
| DE3222221A1 (de) * | 1982-06-12 | 1983-12-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 5-aryloxy-1-chlor-3,3-dimethyl-pentan-2-onen |
| USH214H (en) | 1985-07-19 | 1987-02-03 | Distillation process for the isolation of 1,1-difluoro(mono- or dihalo)ethoxybenzeneamines | |
| US5023380A (en) * | 1989-06-09 | 1991-06-11 | The Dow Chemical Company | Perfluorovinyl compounds |
| US5159038A (en) * | 1989-06-09 | 1992-10-27 | Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5037917A (en) * | 1989-06-09 | 1991-08-06 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5162468A (en) * | 1989-06-09 | 1992-11-10 | The Dow Chemical Company | Perfluorovinyl compounds |
| US5021602A (en) * | 1989-06-09 | 1991-06-04 | The Dow Chemical Company | Reactive compounds containing perfluorocyclobutane rings |
| US5198513A (en) * | 1989-06-09 | 1993-03-30 | The Dow Chemical Company | Reactive compounds containing perfluorovinyl groups |
| US5246782A (en) * | 1990-12-10 | 1993-09-21 | The Dow Chemical Company | Laminates of polymers having perfluorocyclobutane rings and polymers containing perfluorocyclobutane rings |
| US5037918A (en) * | 1989-12-15 | 1991-08-06 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers with crosslinking |
| US5210265A (en) * | 1989-06-09 | 1993-05-11 | The Dow Chemical Company | Reactive compounds containing perfluorocyclobutane rings |
| US5159037A (en) * | 1989-06-09 | 1992-10-27 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers |
| US5159036A (en) * | 1989-12-15 | 1992-10-27 | The Dow Chemical Company | Perfluorocyclobutane ring-containing polymers with crosslinking |
| US5730922A (en) * | 1990-12-10 | 1998-03-24 | The Dow Chemical Company | Resin transfer molding process for composites |
| JPH0586382A (ja) * | 1991-02-06 | 1993-04-06 | Asahi Chem Ind Co Ltd | 潤滑剤 |
| US7531700B2 (en) * | 2003-09-24 | 2009-05-12 | E.I. Du Pont De Nemours And Company | Fluorinated arylethers and methods for use thereof |
| US7686978B2 (en) | 2003-09-24 | 2010-03-30 | E. I. Du Pont De Nemours And Company | Method for the application of active materials onto active surfaces and devices made with such methods |
| WO2024002858A1 (en) * | 2022-06-29 | 2024-01-04 | Solvay Specialty Polymers Italy S.P.A. | Hydrofluoroether composition and method for its preparation |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2005876A1 (enExample) * | 1968-04-09 | 1969-12-19 | Hoechst Ag |
-
1970
- 1970-06-16 DE DE19702029556 patent/DE2029556A1/de active Pending
-
1971
- 1971-06-11 NL NL717108043A patent/NL147122B/xx unknown
- 1971-06-11 CH CH852171A patent/CH551933A/xx not_active IP Right Cessation
- 1971-06-14 BE BE768485A patent/BE768485A/xx unknown
- 1971-06-14 US US152600A patent/US3926989A/en not_active Expired - Lifetime
- 1971-06-15 CA CA115,662A patent/CA1083156A/en not_active Expired
- 1971-06-15 FR FR7121646A patent/FR2096336A5/fr not_active Expired
- 1971-06-16 GB GB2820271A patent/GB1320648A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8318046B2 (en) | 2002-09-24 | 2012-11-27 | E I Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| US8585931B2 (en) | 2002-09-24 | 2013-11-19 | E I Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US8784692B2 (en) | 2002-09-24 | 2014-07-22 | E I Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US8641926B2 (en) | 2003-04-22 | 2014-02-04 | E I Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US8765022B2 (en) | 2004-03-17 | 2014-07-01 | E I Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| US8409476B2 (en) | 2005-06-28 | 2013-04-02 | E I Du Pont De Nemours And Company | High work function transparent conductors |
| US8062553B2 (en) | 2006-12-28 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Compositions of polyaniline made with perfuoropolymeric acid which are heat-enhanced and electronic devices made therewith |
| US8153029B2 (en) | 2006-12-28 | 2012-04-10 | E.I. Du Pont De Nemours And Company | Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof |
| US8491819B2 (en) | 2006-12-29 | 2013-07-23 | E I Du Pont De Nemours And Company | High work-function and high conductivity compositions of electrically conducting polymers |
Also Published As
| Publication number | Publication date |
|---|---|
| NL147122B (nl) | 1975-09-15 |
| NL7108043A (enExample) | 1971-12-20 |
| GB1320648A (en) | 1973-06-20 |
| US3926989A (en) | 1975-12-16 |
| CH551933A (de) | 1974-07-31 |
| FR2096336A5 (enExample) | 1972-02-11 |
| CA1083156A (en) | 1980-08-05 |
| BE768485A (fr) | 1971-12-14 |
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