CA1083156A - Process for the preparation of aryl-1,1,2,2- tetrafluoroethyl ethers - Google Patents
Process for the preparation of aryl-1,1,2,2- tetrafluoroethyl ethersInfo
- Publication number
- CA1083156A CA1083156A CA115,662A CA115662A CA1083156A CA 1083156 A CA1083156 A CA 1083156A CA 115662 A CA115662 A CA 115662A CA 1083156 A CA1083156 A CA 1083156A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- group
- phenol
- groups
- tetrafluoroethylene
- 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
- 238000000034 method Methods 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 27
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 150000002989 phenols Chemical class 0.000 claims abstract description 14
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims abstract description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- -1 hydroxy, formyl Chemical group 0.000 claims description 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical group [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 claims 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical group 0.000 claims 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims 1
- 229960004838 phosphoric acid Drugs 0.000 claims 1
- 235000011007 phosphoric acid Nutrition 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 description 7
- 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
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 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
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NGFPWHGISWUQOI-UHFFFAOYSA-N 2-sec-butylphenol Chemical compound CCC(C)C1=CC=CC=C1O NGFPWHGISWUQOI-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- OLGGVYJRMKGTGP-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]hepta-2,4-dien-6-ol Chemical compound C1=CC=CC2(O)C1O2 OLGGVYJRMKGTGP-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 230000036632 reaction speed Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP2029556.1 | 1970-06-16 | ||
| 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 |
|---|---|
| CA1083156A true CA1083156A (en) | 1980-08-05 |
Family
ID=5774046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA115,662A Expired CA1083156A (en) | 1970-06-16 | 1971-06-15 | Process for the preparation of aryl-1,1,2,2- tetrafluoroethyl ethers |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3926989A (OSRAM) |
| BE (1) | BE768485A (OSRAM) |
| CA (1) | CA1083156A (OSRAM) |
| CH (1) | CH551933A (OSRAM) |
| DE (1) | DE2029556A1 (OSRAM) |
| FR (1) | FR2096336A5 (OSRAM) |
| GB (1) | GB1320648A (OSRAM) |
| NL (1) | NL147122B (OSRAM) |
Families Citing this family (28)
| 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 |
| CA2499364A1 (en) | 2002-09-24 | 2004-04-08 | E. I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
| AU2003275203A1 (en) | 2002-09-24 | 2004-04-19 | E.I. Du Pont De Nemours And Company | Water dispersible polythiophenes made with polymeric acid colloids |
| US7390438B2 (en) | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
| 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 |
| US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
| CN101208369B (zh) | 2005-06-28 | 2013-03-27 | E.I.内穆尔杜邦公司 | 高功函数透明导体 |
| 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 |
| US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
| 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 (OSRAM) * | 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
Also Published As
| Publication number | Publication date |
|---|---|
| NL147122B (nl) | 1975-09-15 |
| NL7108043A (OSRAM) | 1971-12-20 |
| GB1320648A (en) | 1973-06-20 |
| US3926989A (en) | 1975-12-16 |
| DE2029556A1 (de) | 1971-12-23 |
| CH551933A (de) | 1974-07-31 |
| FR2096336A5 (OSRAM) | 1972-02-11 |
| BE768485A (fr) | 1971-12-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |