DE2113858C3 - Verfahren zur Herstellung von 2,3 Dichlorbutadien-(1,3) - Google Patents
Verfahren zur Herstellung von 2,3 Dichlorbutadien-(1,3)Info
- Publication number
- DE2113858C3 DE2113858C3 DE19712113858 DE2113858A DE2113858C3 DE 2113858 C3 DE2113858 C3 DE 2113858C3 DE 19712113858 DE19712113858 DE 19712113858 DE 2113858 A DE2113858 A DE 2113858A DE 2113858 C3 DE2113858 C3 DE 2113858C3
- Authority
- DE
- Germany
- Prior art keywords
- dichlorobutadiene
- reaction vessel
- reaction
- trichlorobutene
- aqueous alkali
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 12
- LIFLRQVHKGGNSG-UHFFFAOYSA-N 2,3-dichlorobuta-1,3-diene Chemical compound ClC(=C)C(Cl)=C LIFLRQVHKGGNSG-UHFFFAOYSA-N 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims description 22
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 11
- 239000003513 alkali Substances 0.000 claims description 9
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 claims description 4
- 238000004821 distillation Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 9
- WZUZDBPJFHQVJC-UHFFFAOYSA-N 2,3,4-trichlorobut-1-ene Chemical compound ClCC(Cl)C(Cl)=C WZUZDBPJFHQVJC-UHFFFAOYSA-N 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 230000008030 elimination Effects 0.000 description 4
- 238000003379 elimination reaction Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052979 sodium sulfide Inorganic materials 0.000 description 3
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- WLIADPFXSACYLS-RQOWECAXSA-N (z)-1,3-dichlorobut-2-ene Chemical compound C\C(Cl)=C\CCl WLIADPFXSACYLS-RQOWECAXSA-N 0.000 description 1
- GBQWGHDWLUYAEG-UHFFFAOYSA-N 1,1,1,2,2-pentachlorobutane Chemical compound CCC(Cl)(Cl)C(Cl)(Cl)Cl GBQWGHDWLUYAEG-UHFFFAOYSA-N 0.000 description 1
- ABSHBZODGOHLFR-UHFFFAOYSA-N 1,1,1-trichlorobutane Chemical compound CCCC(Cl)(Cl)Cl ABSHBZODGOHLFR-UHFFFAOYSA-N 0.000 description 1
- PDKAXHLOFWCWIH-UHFFFAOYSA-N 1,1-dichlorobuta-1,3-diene Chemical class ClC(Cl)=CC=C PDKAXHLOFWCWIH-UHFFFAOYSA-N 0.000 description 1
- KJPPHEWEJWPNFJ-UHFFFAOYSA-N 1,2,2,3,4-pentachlorobutane Chemical compound ClCC(Cl)C(Cl)(Cl)CCl KJPPHEWEJWPNFJ-UHFFFAOYSA-N 0.000 description 1
- NGAAIHKWQFLRDY-UHFFFAOYSA-N 1,2,3,3-tetrachlorobutane Chemical compound CC(Cl)(Cl)C(Cl)CCl NGAAIHKWQFLRDY-UHFFFAOYSA-N 0.000 description 1
- DUDKKPVINWLFBI-UHFFFAOYSA-N 1-chlorobut-1-ene Chemical class CCC=CCl DUDKKPVINWLFBI-UHFFFAOYSA-N 0.000 description 1
- AKQZPPKQVZVYCC-UHFFFAOYSA-N 4,4,4-trichlorobut-1-ene Chemical compound ClC(Cl)(Cl)CC=C AKQZPPKQVZVYCC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 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
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 |
|---|---|---|---|
| GB1408670A GB1283651A (en) | 1970-03-24 | 1970-03-24 | Halogenated unsaturated hydrocarbons |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2113858A1 DE2113858A1 (de) | 1971-10-07 |
| DE2113858B2 DE2113858B2 (de) | 1973-05-24 |
| DE2113858C3 true DE2113858C3 (de) | 1973-12-20 |
Family
ID=10034737
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712113858 Expired DE2113858C3 (de) | 1970-03-24 | 1971-03-23 | Verfahren zur Herstellung von 2,3 Dichlorbutadien-(1,3) |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS546522B1 (enExample) |
| BE (1) | BE764779A (enExample) |
| CA (1) | CA949077A (enExample) |
| DE (1) | DE2113858C3 (enExample) |
| FR (1) | FR2083533B1 (enExample) |
| GB (1) | GB1283651A (enExample) |
| NL (1) | NL7103563A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2545341C2 (de) * | 1975-10-09 | 1983-02-10 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von 2,3- Dichlorbutadien-(1,3) |
| JPS5791931A (en) * | 1980-11-27 | 1982-06-08 | Denki Kagaku Kogyo Kk | Preparation of 2,3-dichlorobutadiene-1,3 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1217947B (de) * | 1964-10-07 | 1966-06-02 | Bayer Ag | Verfahren zur Herstellung von 2, 3-Dichlorbutadien-(1, 3) |
-
1970
- 1970-03-24 GB GB1408670A patent/GB1283651A/en not_active Expired
-
1971
- 1971-03-08 CA CA107,063A patent/CA949077A/en not_active Expired
- 1971-03-17 NL NL7103563A patent/NL7103563A/xx unknown
- 1971-03-23 FR FR7110093A patent/FR2083533B1/fr not_active Expired
- 1971-03-23 DE DE19712113858 patent/DE2113858C3/de not_active Expired
- 1971-03-24 JP JP1714271A patent/JPS546522B1/ja active Pending
- 1971-03-24 BE BE764779A patent/BE764779A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS546522B1 (enExample) | 1979-03-29 |
| BE764779A (fr) | 1971-09-24 |
| CA949077A (en) | 1974-06-11 |
| DE2113858B2 (de) | 1973-05-24 |
| DE2113858A1 (de) | 1971-10-07 |
| NL7103563A (enExample) | 1971-09-28 |
| GB1283651A (en) | 1972-08-02 |
| FR2083533A1 (enExample) | 1971-12-17 |
| FR2083533B1 (enExample) | 1975-06-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |