DE1114185B - Verfahren zur Herstellung von 2-Chlorbutadien-1,3 - Google Patents
Verfahren zur Herstellung von 2-Chlorbutadien-1,3Info
- Publication number
- DE1114185B DE1114185B DED32865A DED0032865A DE1114185B DE 1114185 B DE1114185 B DE 1114185B DE D32865 A DED32865 A DE D32865A DE D0032865 A DED0032865 A DE D0032865A DE 1114185 B DE1114185 B DE 1114185B
- Authority
- DE
- Germany
- Prior art keywords
- chlorobutadiene
- distillation
- dichlorobutene
- boiling point
- dehydrochlorination
- 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
- YACLQRRMGMJLJV-UHFFFAOYSA-N chloroprene Chemical compound ClC(=C)C=C YACLQRRMGMJLJV-UHFFFAOYSA-N 0.000 title claims description 26
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 4
- 238000009835 boiling Methods 0.000 claims description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 11
- 238000004821 distillation Methods 0.000 claims description 11
- 239000007788 liquid Substances 0.000 claims description 7
- 150000002894 organic compounds Chemical class 0.000 claims description 7
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- 238000007033 dehydrochlorination reaction Methods 0.000 claims description 6
- 238000010992 reflux Methods 0.000 claims description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 3
- 239000008096 xylene Substances 0.000 claims description 3
- SEQRDAAUNCRFIT-UHFFFAOYSA-N 1,1-dichlorobutane Chemical compound CCCC(Cl)Cl SEQRDAAUNCRFIT-UHFFFAOYSA-N 0.000 claims description 2
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- RMISVOPUIFJTEO-UHFFFAOYSA-N 2,3-dichlorobutane Chemical class CC(Cl)C(C)Cl RMISVOPUIFJTEO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000004508 fractional distillation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 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
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical compound CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 description 1
- -1 B. octane Chemical class 0.000 description 1
- 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 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/25—Preparation of halogenated hydrocarbons by splitting-off hydrogen halides from halogenated hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/38—Separation; Purification; Stabilisation; Use of additives
- C07C17/383—Separation; Purification; Stabilisation; Use of additives by distillation
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB11271/59A GB873221A (en) | 1959-04-02 | 1959-04-02 | Production of chloroprene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1114185B true DE1114185B (de) | 1961-09-28 |
Family
ID=9983143
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DED32865A Pending DE1114185B (de) | 1959-04-02 | 1960-03-15 | Verfahren zur Herstellung von 2-Chlorbutadien-1,3 |
Country Status (6)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL288175A (US06262066-20010717-C00560.png) * | 1962-02-08 | |||
| DE1272916B (de) * | 1966-07-26 | 1968-07-18 | Knapsack Ag | Verfahren zur gemeinsamen Herstellung von 2-Chlorbutadien-(1, 3) und 1-Chlorbutadien-(1, 3) |
| GB1582830A (en) * | 1976-02-19 | 1981-01-14 | Bp Chem Int Ltd | Production of chloroprene |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB492689A (en) * | 1936-03-28 | 1938-09-26 | Ig Farbenindustrie Ag | Manufacture of ª-halogen-butadienes-1, 3 |
-
0
- NL NL249729D patent/NL249729A/xx unknown
-
1959
- 1959-04-02 GB GB11271/59A patent/GB873221A/en not_active Expired
-
1960
- 1960-03-15 DE DED32865A patent/DE1114185B/de active Pending
- 1960-03-15 US US15055A patent/US3026360A/en not_active Expired - Lifetime
- 1960-03-23 FR FR822153A patent/FR1251841A/fr not_active Expired
- 1960-03-30 BE BE589230A patent/BE589230A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL249729A (US06262066-20010717-C00560.png) | |
| BE589230A (fr) | 1960-08-30 |
| US3026360A (en) | 1962-03-20 |
| GB873221A (en) | 1961-07-19 |
| FR1251841A (fr) | 1961-01-20 |
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