DE2159012A1 - Verfahren zur Isomerisation von Dichlorbutenen - Google Patents
Verfahren zur Isomerisation von DichlorbutenenInfo
- Publication number
- DE2159012A1 DE2159012A1 DE19712159012 DE2159012A DE2159012A1 DE 2159012 A1 DE2159012 A1 DE 2159012A1 DE 19712159012 DE19712159012 DE 19712159012 DE 2159012 A DE2159012 A DE 2159012A DE 2159012 A1 DE2159012 A1 DE 2159012A1
- Authority
- DE
- Germany
- Prior art keywords
- dichlorobutene
- diol
- isomerization
- catalyst
- compound
- 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
- 238000006317 isomerization reaction Methods 0.000 title claims description 13
- 238000000034 method Methods 0.000 title claims description 11
- UAZUEJTXWAXSMA-UHFFFAOYSA-N 1,1-dichlorobut-1-ene Chemical class CCC=C(Cl)Cl UAZUEJTXWAXSMA-UHFFFAOYSA-N 0.000 title claims description 8
- 239000003054 catalyst Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- FQDIANVAWVHZIR-OWOJBTEDSA-N trans-1,4-Dichlorobutene Chemical compound ClC\C=C\CCl FQDIANVAWVHZIR-OWOJBTEDSA-N 0.000 claims description 14
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 claims description 6
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 6
- 229940120693 copper naphthenate Drugs 0.000 claims description 4
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 claims description 4
- 235000013772 propylene glycol Nutrition 0.000 claims description 4
- 239000004358 Butane-1, 3-diol Substances 0.000 claims description 3
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 3
- 235000019437 butane-1,3-diol Nutrition 0.000 claims description 3
- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 claims description 3
- 229960004063 propylene glycol Drugs 0.000 claims description 3
- PSJBSUHYCGQTHZ-UHFFFAOYSA-N 3-Methoxy-1,2-propanediol Chemical compound COCC(O)CO PSJBSUHYCGQTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002202 Polyethylene glycol Substances 0.000 claims description 2
- 229920001223 polyethylene glycol Polymers 0.000 claims description 2
- 125000001931 aliphatic group Chemical class 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 13
- XVEASTGLHPVZNA-UHFFFAOYSA-N 3,4-dichlorobut-1-ene Chemical compound ClCC(Cl)C=C XVEASTGLHPVZNA-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000654 additive Substances 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000009825 accumulation Methods 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- XKNMCAWHCJVFQZ-UHFFFAOYSA-N C(CC(C)O)O.C(C(C)O)O.C(CO)O Chemical compound C(CC(C)O)O.C(C(C)O)O.C(CO)O XKNMCAWHCJVFQZ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical class [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical class [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical class [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical class [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 150000007824 aliphatic compounds Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- RAVDFEPNANSXII-UHFFFAOYSA-N butane-1,2,4-triol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCCC(O)CO RAVDFEPNANSXII-UHFFFAOYSA-N 0.000 description 1
- OWBTYPJTUOEWEK-JCDJMFQYSA-N butane-2,3-diol Chemical compound [13CH3][13CH](O)[13CH]([13CH3])O OWBTYPJTUOEWEK-JCDJMFQYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940113115 polyethylene glycol 200 Drugs 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000010936 titanium Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000011701 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/35—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction
- C07C17/358—Preparation of halogenated hydrocarbons by reactions not affecting the number of carbon or of halogen atoms in the reaction by isomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5746770 | 1970-12-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2159012A1 true DE2159012A1 (de) | 1972-06-08 |
Family
ID=10479252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712159012 Pending DE2159012A1 (de) | 1970-12-03 | 1971-11-29 | Verfahren zur Isomerisation von Dichlorbutenen |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5317566B1 (enExample) |
| BE (1) | BE776053A (enExample) |
| DE (1) | DE2159012A1 (enExample) |
| FR (1) | FR2116485B3 (enExample) |
| GB (1) | GB1315980A (enExample) |
| IT (1) | IT941941B (enExample) |
| NL (1) | NL7116198A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5692225A (en) | 1979-12-25 | 1981-07-25 | Denki Kagaku Kogyo Kk | Isomerizing method of dichlorobutene |
-
1970
- 1970-12-03 GB GB1315980D patent/GB1315980A/en not_active Expired
-
1971
- 1971-11-25 NL NL7116198A patent/NL7116198A/xx unknown
- 1971-11-29 DE DE19712159012 patent/DE2159012A1/de active Pending
- 1971-11-30 BE BE776053A patent/BE776053A/xx unknown
- 1971-12-01 IT IT3192671A patent/IT941941B/it active
- 1971-12-02 FR FR7143241A patent/FR2116485B3/fr not_active Expired
- 1971-12-02 JP JP9754871A patent/JPS5317566B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1315980A (en) | 1973-05-09 |
| IT941941B (it) | 1973-03-10 |
| FR2116485A3 (enExample) | 1972-07-13 |
| NL7116198A (enExample) | 1972-06-06 |
| JPS5317566B1 (enExample) | 1978-06-09 |
| FR2116485B3 (enExample) | 1974-08-23 |
| BE776053A (fr) | 1972-05-30 |
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