DE2208599A1 - Fluorierte Dioxole - Google Patents
Fluorierte DioxoleInfo
- Publication number
- DE2208599A1 DE2208599A1 DE19722208599 DE2208599A DE2208599A1 DE 2208599 A1 DE2208599 A1 DE 2208599A1 DE 19722208599 DE19722208599 DE 19722208599 DE 2208599 A DE2208599 A DE 2208599A DE 2208599 A1 DE2208599 A1 DE 2208599A1
- Authority
- DE
- Germany
- Prior art keywords
- perfluoro
- dioxolane
- fluorinated
- dimethyl
- dioxole
- 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
- ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical class C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 title claims description 9
- 238000000034 method Methods 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 239000013256 coordination polymer Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
- 150000004862 dioxolanes Chemical class 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 239000000047 product Substances 0.000 description 10
- YSYRISKCBOPJRG-UHFFFAOYSA-N 4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxole Chemical compound FC1=C(F)OC(C(F)(F)F)(C(F)(F)F)O1 YSYRISKCBOPJRG-UHFFFAOYSA-N 0.000 description 9
- 239000000203 mixture Substances 0.000 description 7
- PQTSJAIWJYMBOX-UHFFFAOYSA-N 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(F)(Cl)C(F)(Cl)O1 PQTSJAIWJYMBOX-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 2
- VAFAODCZDOCONB-UHFFFAOYSA-N 4,5-dibromo-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(F)(Br)C(F)(Br)O1 VAFAODCZDOCONB-UHFFFAOYSA-N 0.000 description 2
- 125000006414 CCl Chemical group ClC* 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- TXGPGHBYAPBDAG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C1(F)F TXGPGHBYAPBDAG-UHFFFAOYSA-N 0.000 description 1
- NHJFHUKLZMQIHN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanoyl 2,2,3,3,3-pentafluoropropaneperoxoate Chemical compound FC(F)(F)C(F)(F)C(=O)OOC(=O)C(F)(F)C(F)(F)F NHJFHUKLZMQIHN-UHFFFAOYSA-N 0.000 description 1
- HFNSTEOEZJBXIF-UHFFFAOYSA-N 2,2,4,5-tetrafluoro-1,3-dioxole Chemical compound FC1=C(F)OC(F)(F)O1 HFNSTEOEZJBXIF-UHFFFAOYSA-N 0.000 description 1
- XKTYXVDYIKIYJP-UHFFFAOYSA-N 3h-dioxole Chemical compound C1OOC=C1 XKTYXVDYIKIYJP-UHFFFAOYSA-N 0.000 description 1
- RSNKMTZZWVFGES-UHFFFAOYSA-N 4,4,5,5-tetrachloro-2,2-bis(trifluoromethyl)-1,3-dioxolane Chemical compound FC(F)(F)C1(C(F)(F)F)OC(Cl)(Cl)C(Cl)(Cl)O1 RSNKMTZZWVFGES-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910018287 SbF 5 Inorganic materials 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000011874 heated mixture Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- UJMWVICAENGCRF-UHFFFAOYSA-N oxygen difluoride Chemical group FOF UJMWVICAENGCRF-UHFFFAOYSA-N 0.000 description 1
- -1 perfluoro Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F24/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11855971A | 1971-02-24 | 1971-02-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2208599A1 true DE2208599A1 (de) | 1972-09-21 |
Family
ID=22379357
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722208599 Pending DE2208599A1 (de) | 1971-02-24 | 1972-02-23 | Fluorierte Dioxole |
| DE19722227538 Pending DE2227538A1 (de) | 1971-02-24 | 1972-02-23 | Polymerisate von fluorierten dioxolen |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722227538 Pending DE2227538A1 (de) | 1971-02-24 | 1972-02-23 | Polymerisate von fluorierten dioxolen |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA955951A (enExample) |
| DE (2) | DE2208599A1 (enExample) |
| FR (1) | FR2126340B1 (enExample) |
| GB (1) | GB1361346A (enExample) |
| IT (1) | IT959549B (enExample) |
| NL (1) | NL7202253A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991004251A3 (en) * | 1989-09-18 | 1991-07-11 | Du Pont | Polyhalodihydrodioxins and polyhalodioxoles |
| JP3233967B2 (ja) | 1991-02-07 | 2001-12-04 | アウシモント、ソチエタ、ペル、アツィオーニ | １，３−ジオキソランの脱ハロゲン化方法 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838707A (ja) * | 1981-08-20 | 1983-03-07 | イ−・アイ・デユポン・デ・ニモアス・アンド・カンパニ− | パ−フルオロ−２，２−ジメチル−１，３−ジオキソ−ルの無定形共重合体 |
| US4429143A (en) * | 1981-09-28 | 1984-01-31 | E. I. Du Pont De Nemours & Co. | Cyclic monomers derived from trifluoropyruvate esters |
| US5233058A (en) * | 1988-07-25 | 1993-08-03 | E. I. Du Pont De Nemours And Company | Partially fluorinated compounds and polymers |
| EP0489756B1 (en) * | 1989-08-28 | 1995-12-13 | E.I. Du Pont De Nemours And Company | Process for the preparation of halogenated 2,2-bis(trifluoromethyl)-1,3-dioxolanes |
| US5177224A (en) * | 1989-08-28 | 1993-01-05 | E. I. Du Pont De Nemours And Company | Process for the preparation of halogenated 2,2-bis(trifluoromethyl)-1,3-dioxolanes |
| WO1991009025A2 (en) * | 1989-12-11 | 1991-06-27 | E.I. Du Pont De Nemours And Company | Partially fluorinated compounds and polymers |
| IT1244709B (it) * | 1991-02-07 | 1994-08-08 | Ausimont Spa | Processo per la preaparazione di 1.3-diossoli |
| CN112310302A (zh) * | 2019-07-30 | 2021-02-02 | 陕西坤同半导体科技有限公司 | 一种有机发光器件 |
-
1972
- 1972-01-27 CA CA133,340A patent/CA955951A/en not_active Expired
- 1972-02-18 GB GB763872A patent/GB1361346A/en not_active Expired
- 1972-02-21 NL NL7202253A patent/NL7202253A/xx unknown
- 1972-02-23 DE DE19722208599 patent/DE2208599A1/de active Pending
- 1972-02-23 IT IT2094772A patent/IT959549B/it active
- 1972-02-23 DE DE19722227538 patent/DE2227538A1/de active Pending
- 1972-02-23 FR FR7206082A patent/FR2126340B1/fr not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991004251A3 (en) * | 1989-09-18 | 1991-07-11 | Du Pont | Polyhalodihydrodioxins and polyhalodioxoles |
| JP3233967B2 (ja) | 1991-02-07 | 2001-12-04 | アウシモント、ソチエタ、ペル、アツィオーニ | １，３−ジオキソランの脱ハロゲン化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2126340B1 (enExample) | 1976-03-05 |
| DE2227538A1 (de) | 1973-08-30 |
| NL7202253A (enExample) | 1972-08-28 |
| GB1361346A (en) | 1974-07-24 |
| IT959549B (it) | 1973-11-10 |
| CA955951A (en) | 1974-10-08 |
| FR2126340A1 (enExample) | 1972-10-06 |
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