DE1170935B - Verfahren zur gleichzeitigen Herstellung von Tetrafluoraethylen und Hexofluorpropylen und gegebenenfalls geringen Mengen Perfluorcyclobutan durch Pyrolyse von Chlordifluormethan - Google Patents
Verfahren zur gleichzeitigen Herstellung von Tetrafluoraethylen und Hexofluorpropylen und gegebenenfalls geringen Mengen Perfluorcyclobutan durch Pyrolyse von ChlordifluormethanInfo
- Publication number
- DE1170935B DE1170935B DEP27951A DEP0027951A DE1170935B DE 1170935 B DE1170935 B DE 1170935B DE P27951 A DEP27951 A DE P27951A DE P0027951 A DEP0027951 A DE P0027951A DE 1170935 B DE1170935 B DE 1170935B
- Authority
- DE
- Germany
- Prior art keywords
- chlorodifluoromethane
- pyrolysis
- perfluorocyclobutane
- tetrafluoroethylene
- temperature
- 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
- 238000000197 pyrolysis Methods 0.000 title claims description 37
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 title claims description 36
- BCCOBQSFUDVTJQ-UHFFFAOYSA-N octafluorocyclobutane Chemical compound FC1(F)C(F)(F)C(F)(F)C1(F)F BCCOBQSFUDVTJQ-UHFFFAOYSA-N 0.000 title claims description 24
- 235000019407 octafluorocyclobutane Nutrition 0.000 title claims description 24
- 238000000034 method Methods 0.000 title claims description 23
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 title claims description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 35
- 239000000047 product Substances 0.000 claims description 32
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical group FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims description 24
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 3
- 230000001351 cycling effect Effects 0.000 claims 1
- 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 8
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- -1 Hexafluoropropylene, tetrafluoroethylene Chemical group 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 230000007423 decrease Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- RWRIWBAIICGTTQ-UHFFFAOYSA-N difluoromethane Chemical compound FCF RWRIWBAIICGTTQ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 229910000623 nickel–chromium alloy Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- PRPAGESBURMWTI-UHFFFAOYSA-N [C].[F] Chemical compound [C].[F] PRPAGESBURMWTI-UHFFFAOYSA-N 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- STJYMUBZVMSMBP-UHFFFAOYSA-N chlorocyclobutane Chemical compound ClC1CCC1 STJYMUBZVMSMBP-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/263—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions
- C07C17/269—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of only halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58895A US3306940A (en) | 1960-09-28 | 1960-09-28 | Process for the manufacture of perfluoroolefins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1170935B true DE1170935B (de) | 1964-05-27 |
Family
ID=22019577
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEP27951A Pending DE1170935B (de) | 1960-09-28 | 1961-09-28 | Verfahren zur gleichzeitigen Herstellung von Tetrafluoraethylen und Hexofluorpropylen und gegebenenfalls geringen Mengen Perfluorcyclobutan durch Pyrolyse von Chlordifluormethan |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0287219A1 (en) * | 1987-04-10 | 1988-10-19 | Imperial Chemical Industries Plc | Production of tetrafluoroethylene and hexafluoropropylene |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3337645A (en) * | 1963-04-05 | 1967-08-22 | Mobil Oil Corp | Catalytic conversion of fluorocarbons |
| DE1236497B (de) * | 1965-02-02 | 1967-03-16 | Fluorwerke Dohna | Verfahren zur Herstellung von Perfluorpropen |
| US3873630A (en) * | 1972-06-12 | 1975-03-25 | Du Pont | Process for pyrolyzing tetrafluoroethylene to hexafluoropropylene |
| US5068472A (en) * | 1989-12-19 | 1991-11-26 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| US5057634A (en) * | 1989-12-19 | 1991-10-15 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| US5043491A (en) * | 1989-12-19 | 1991-08-27 | E. I. Du Pont De Nemours And Company | Multistep synthesis of hexafluoropropylene |
| US5474657A (en) * | 1994-02-10 | 1995-12-12 | Minnesota Mining And Manufacturing Company | Preparation of F-alkyl F-isobutyl ethers by electrochemical fluorination |
| JP3946764B2 (ja) * | 1995-02-17 | 2007-07-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | テトラフルオロエチレンの合成法 |
| US20020032356A1 (en) * | 2000-07-14 | 2002-03-14 | Gelblum Peter Gideon | Synthesis of perfluoroolefins |
| US6924403B2 (en) * | 2002-06-26 | 2005-08-02 | E. I. Du Pont De Nemours And Company | Synthesis of hexafluoropropylene |
| CN110078586B (zh) * | 2019-05-06 | 2022-05-27 | 聊城氟尔新材料科技有限公司 | 一种四氟乙烯联产六氟丙烯的装置和工艺及应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2404374A (en) * | 1943-04-23 | 1946-07-23 | Du Pont | Polyfluorinated cycloparaffins and process for producing them |
| US2551573A (en) * | 1945-11-30 | 1951-05-08 | Du Pont | Pyrolysis of chloro-fluoro alkanes |
| US2617836A (en) * | 1951-04-18 | 1952-11-11 | Minnesota Mining & Mfg | Production of olefinic c4f8 |
| US2758138A (en) * | 1954-05-06 | 1956-08-07 | Du Pont | Pyrolysis process for making perfluoropropene from tetrafluoroethylene |
| DE1073475B (de) * | 1958-07-29 | 1960-01-21 | Farbwerke Hoechst Aktiengesellschaft vormals Meister Lucius &. Brüning, Frankfurt/M | Verfahren zur Herstellung von Tetrafluoräthylen |
| US2979539A (en) * | 1959-01-06 | 1961-04-11 | Minnesota Mining & Mfg | Difluorocarbene free radicals in the synthesis of fluorinated olefinic compounds |
| US3016405A (en) * | 1959-01-07 | 1962-01-09 | Du Pont | Metal catalyzed pyrolysis of fluoromethanes |
| US3022357A (en) * | 1959-10-08 | 1962-02-20 | Du Pont | Purification of fluorocarbons |
| US3009966A (en) * | 1960-02-08 | 1961-11-21 | Pennsalt Chemicals Corp | Production of fluorinated compounds |
-
0
- NL NL122622D patent/NL122622C/xx active
- NL NL269647D patent/NL269647A/xx unknown
-
1960
- 1960-09-28 US US58895A patent/US3306940A/en not_active Expired - Lifetime
-
1961
- 1961-09-26 GB GB34422/61A patent/GB917093A/en not_active Expired
- 1961-09-27 BE BE608590A patent/BE608590A/fr unknown
- 1961-09-28 DE DEP27951A patent/DE1170935B/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0287219A1 (en) * | 1987-04-10 | 1988-10-19 | Imperial Chemical Industries Plc | Production of tetrafluoroethylene and hexafluoropropylene |
Also Published As
| Publication number | Publication date |
|---|---|
| GB917093A (en) | 1963-01-30 |
| BE608590A (fr) | 1962-03-27 |
| US3306940A (en) | 1967-02-28 |
| NL269647A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | |
| NL122622C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
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