CH495312A - Verfahren zur Herstellung von Vinyläthern perhalogenierter Alkohole - Google Patents
Verfahren zur Herstellung von Vinyläthern perhalogenierter AlkoholeInfo
- Publication number
- CH495312A CH495312A CH1068A CH1068A CH495312A CH 495312 A CH495312 A CH 495312A CH 1068 A CH1068 A CH 1068A CH 1068 A CH1068 A CH 1068A CH 495312 A CH495312 A CH 495312A
- Authority
- CH
- Switzerland
- Prior art keywords
- ether
- mol
- ethyl
- formula
- reaction
- Prior art date
Links
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical class C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 150000001298 alcohols Chemical class 0.000 title claims abstract description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 36
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims abstract description 24
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 239000003085 diluting agent Substances 0.000 claims abstract description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical class CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 46
- 239000000460 chlorine Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- 150000007514 bases Chemical class 0.000 claims description 4
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 abstract description 6
- HXJUTPCZVOIRIF-UHFFFAOYSA-N Tetrahydrothiophene-1,1-dioxide, Natural products O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 abstract description 2
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 abstract 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical group FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 34
- 238000009835 boiling Methods 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 20
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 19
- 239000001110 calcium chloride Substances 0.000 description 19
- 229910001628 calcium chloride Inorganic materials 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- -1 perfluorocarbon radicals Chemical class 0.000 description 15
- 238000004508 fractional distillation Methods 0.000 description 14
- 238000010992 reflux Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
- 235000017557 sodium bicarbonate Nutrition 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000012043 crude product Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
- 229940035423 ethyl ether Drugs 0.000 description 5
- 229940079827 sodium hydrogen sulfite Drugs 0.000 description 5
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 5
- 235000010265 sodium sulphite Nutrition 0.000 description 5
- 238000001256 steam distillation Methods 0.000 description 5
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- FKTXDTWDCPTPHK-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical group FC(F)(F)[C](F)C(F)(F)F FKTXDTWDCPTPHK-UHFFFAOYSA-N 0.000 description 3
- JSRAUKJOZJHENF-UHFFFAOYSA-N 1,1,1,2,3,3,4,4-octafluoro-6-[3,3,4,4,5,6,6,6-octafluoro-5-(trifluoromethyl)hexoxy]-2-(trifluoromethyl)hexane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(F)(F)C(F)(F)CCOCCC(F)(F)C(F)(F)C(F)(C(F)(F)F)C(F)(F)F JSRAUKJOZJHENF-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 238000005660 chlorination reaction Methods 0.000 description 3
- ZPVFXWAIPNKSLJ-UHFFFAOYSA-N trifluoromethoxyethane Chemical compound CCOC(F)(F)F ZPVFXWAIPNKSLJ-UHFFFAOYSA-N 0.000 description 3
- CRJVPUWOURIOCW-UHFFFAOYSA-N 1-ethoxy-1,1,2,2,2-pentafluoroethane Chemical compound CCOC(F)(F)C(F)(F)F CRJVPUWOURIOCW-UHFFFAOYSA-N 0.000 description 2
- RMFXYVDVYHFRRQ-UHFFFAOYSA-N 2-ethoxy-1,1,1,2,3,3,3-heptafluoropropane Chemical compound CCOC(F)(C(F)(F)F)C(F)(F)F RMFXYVDVYHFRRQ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000002140 halogenating effect Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000001678 irradiating effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000009183 running Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- YZIQRUBSHCOAJB-UHFFFAOYSA-N 1,1,1,2-tetrafluoro-3-[3,4,4,4-tetrafluoro-3-(trifluoromethyl)butan-2-yl]oxy-2-(trifluoromethyl)butane Chemical compound FC(F)(F)C(F)(C(F)(F)F)C(C)OC(C)C(F)(C(F)(F)F)C(F)(F)F YZIQRUBSHCOAJB-UHFFFAOYSA-N 0.000 description 1
- RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical class ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PRPSNEJCBNKDII-UHFFFAOYSA-N 1-chloro-2-(trifluoromethoxy)ethane Chemical compound FC(F)(F)OCCCl PRPSNEJCBNKDII-UHFFFAOYSA-N 0.000 description 1
- UVMBRRGVNABPCP-UHFFFAOYSA-N 1-ethenoxy-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)OC=C UVMBRRGVNABPCP-UHFFFAOYSA-N 0.000 description 1
- ZPDGEIZOHMBIST-UHFFFAOYSA-N 2-ethenoxy-1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)(C(F)(F)F)OC=C ZPDGEIZOHMBIST-UHFFFAOYSA-N 0.000 description 1
- ZNSMNVMLTJELDZ-UHFFFAOYSA-N Bis(2-chloroethyl)ether Chemical compound ClCCOCCCl ZNSMNVMLTJELDZ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- OIEGKKVOQKREAU-UHFFFAOYSA-N FC(C(COCC(C(C(F)(F)F)(C(F)(F)F)F)Cl)Cl)(C(F)(F)F)C(F)(F)F Chemical compound FC(C(COCC(C(C(F)(F)F)(C(F)(F)F)F)Cl)Cl)(C(F)(F)F)C(F)(F)F OIEGKKVOQKREAU-UHFFFAOYSA-N 0.000 description 1
- OAYPSJHKYHVJHO-UHFFFAOYSA-N FC(CCOCCC(C(C1(F)F)(F)F)(C1(F)F)F)(C(C1(F)F)(F)F)C1(F)F Chemical compound FC(CCOCCC(C(C1(F)F)(F)F)(C1(F)F)F)(C(C1(F)F)(F)F)C1(F)F OAYPSJHKYHVJHO-UHFFFAOYSA-N 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 1
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QLOAVXSYZAJECW-UHFFFAOYSA-N methane;molecular fluorine Chemical compound C.FF QLOAVXSYZAJECW-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- JRHMNRMPVRXNOS-UHFFFAOYSA-N trifluoro(methoxy)methane Chemical compound COC(F)(F)F JRHMNRMPVRXNOS-UHFFFAOYSA-N 0.000 description 1
- FPDZOFFZSWSOSL-UHFFFAOYSA-N trifluoromethoxyethene Chemical compound FC(F)(F)OC=C FPDZOFFZSWSOSL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF51188A DE1294954B (de) | 1967-01-07 | 1967-01-07 | Verfahren zur Herstellung von Vinylaethern perhalogenierter, tertiaerer Alkohole |
| DEF0052459 | 1967-05-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495312A true CH495312A (de) | 1970-08-31 |
Family
ID=25977575
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1068A CH495312A (de) | 1967-01-07 | 1968-01-03 | Verfahren zur Herstellung von Vinyläthern perhalogenierter Alkohole |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE709062A (en)van) |
| CH (1) | CH495312A (en)van) |
| DE (2) | DE1294954B (en)van) |
| ES (1) | ES348927A1 (en)van) |
| FR (1) | FR1559044A (en)van) |
| NL (1) | NL6800017A (en)van) |
-
1967
- 1967-01-07 DE DEF51188A patent/DE1294954B/de active Pending
- 1967-05-19 DE DE19671618424 patent/DE1618424A1/de active Pending
-
1968
- 1968-01-02 NL NL6800017A patent/NL6800017A/xx unknown
- 1968-01-03 CH CH1068A patent/CH495312A/de not_active IP Right Cessation
- 1968-01-04 ES ES348927A patent/ES348927A1/es not_active Expired
- 1968-01-08 BE BE709062D patent/BE709062A/xx unknown
- 1968-01-08 FR FR1559044D patent/FR1559044A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6800017A (en)van) | 1968-07-08 |
| FR1559044A (en)van) | 1969-03-07 |
| DE1294954B (de) | 1969-05-14 |
| ES348927A1 (es) | 1969-08-16 |
| BE709062A (en)van) | 1968-07-08 |
| DE1618424A1 (de) | 1971-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |