DE1247297B - Verfahren zur Herstellung von 2-Chlorbutadien-(1, 3) - Google Patents
Verfahren zur Herstellung von 2-Chlorbutadien-(1, 3)Info
- Publication number
- DE1247297B DE1247297B DEK57673A DEK0057673A DE1247297B DE 1247297 B DE1247297 B DE 1247297B DE K57673 A DEK57673 A DE K57673A DE K0057673 A DEK0057673 A DE K0057673A DE 1247297 B DE1247297 B DE 1247297B
- Authority
- DE
- Germany
- Prior art keywords
- trichlorobutane
- chlorobutadiene
- dichlorobutenes
- reaction
- thermal cleavage
- 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 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- VHRSGZSWEJBMSI-UHFFFAOYSA-N 1,3,3-trichlorobutane Chemical compound CC(Cl)(Cl)CCCl VHRSGZSWEJBMSI-UHFFFAOYSA-N 0.000 claims description 25
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical class CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 15
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 claims description 15
- 238000003776 cleavage reaction Methods 0.000 claims description 11
- 230000007017 scission Effects 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000011261 inert gas Substances 0.000 claims description 5
- ABSHBZODGOHLFR-UHFFFAOYSA-N 1,1,1-trichlorobutane Chemical class CCCC(Cl)(Cl)Cl ABSHBZODGOHLFR-UHFFFAOYSA-N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000001273 butane Substances 0.000 claims 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 13
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 13
- UNTJXPFYXVCMFE-UHFFFAOYSA-N 2,2,3-trichlorobutane Chemical compound CC(Cl)C(C)(Cl)Cl UNTJXPFYXVCMFE-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000000197 pyrolysis Methods 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- RMZZAEDPBSKZOM-UHFFFAOYSA-N 1,2,3-trichlorobutane Chemical compound CC(Cl)C(Cl)CCl RMZZAEDPBSKZOM-UHFFFAOYSA-N 0.000 description 2
- BSRTYNDWQXVCKR-UHFFFAOYSA-N 2,2-dichlorobutane Chemical compound CCC(C)(Cl)Cl BSRTYNDWQXVCKR-UHFFFAOYSA-N 0.000 description 2
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical class [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 241000589614 Pseudomonas stutzeri Species 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- WFYPICNXBKQZGB-UHFFFAOYSA-N butenyne Chemical group C=CC#C WFYPICNXBKQZGB-UHFFFAOYSA-N 0.000 description 2
- 229910002090 carbon oxide Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 239000012495 reaction gas Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PCPYTNCQOSFKGG-ONEGZZNKSA-N (1e)-1-chlorobuta-1,3-diene Chemical compound Cl\C=C\C=C PCPYTNCQOSFKGG-ONEGZZNKSA-N 0.000 description 1
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical class CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 238000004939 coking Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- -1 for example Chemical compound 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C21/00—Acyclic unsaturated compounds containing halogen atoms
- C07C21/02—Acyclic unsaturated compounds containing halogen atoms containing carbon-to-carbon double bonds
- C07C21/19—Halogenated dienes
- C07C21/20—Halogenated butadienes
- C07C21/21—Chloroprene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK57673A DE1247297B (de) | 1965-11-16 | 1965-11-16 | Verfahren zur Herstellung von 2-Chlorbutadien-(1, 3) |
| GB49359/66A GB1111137A (en) | 1965-11-16 | 1966-11-03 | Process for the manufacture of 2-chlorobutadiene-(1,3) |
| AT1056666A AT263739B (de) | 1965-11-16 | 1966-11-15 | Verfahren zur Herstellung von 2-Chlorbutadien-(1,3) |
| NL6616099A NL6616099A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-11-16 | 1966-11-15 | |
| FR83845A FR1499799A (fr) | 1965-11-16 | 1966-11-16 | Procédé de préparation de 2-chlorobutadiène |
| BE689780D BE689780A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1965-11-16 | 1966-11-16 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEK57673A DE1247297B (de) | 1965-11-16 | 1965-11-16 | Verfahren zur Herstellung von 2-Chlorbutadien-(1, 3) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1247297B true DE1247297B (de) | 1967-08-17 |
Family
ID=7228353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEK57673A Pending DE1247297B (de) | 1965-11-16 | 1965-11-16 | Verfahren zur Herstellung von 2-Chlorbutadien-(1, 3) |
Country Status (6)
-
1965
- 1965-11-16 DE DEK57673A patent/DE1247297B/de active Pending
-
1966
- 1966-11-03 GB GB49359/66A patent/GB1111137A/en not_active Expired
- 1966-11-15 NL NL6616099A patent/NL6616099A/xx unknown
- 1966-11-15 AT AT1056666A patent/AT263739B/de active
- 1966-11-16 FR FR83845A patent/FR1499799A/fr not_active Expired
- 1966-11-16 BE BE689780D patent/BE689780A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL6616099A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-17 |
| FR1499799A (fr) | 1967-10-27 |
| GB1111137A (en) | 1968-04-24 |
| BE689780A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-05-02 |
| AT263739B (de) | 1968-08-12 |
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