IE43137B1 - Production of 1,1-dihalo-4-methylpenta-1,3-or 1,4-dienes - Google Patents
Production of 1,1-dihalo-4-methylpenta-1,3-or 1,4-dienesInfo
- Publication number
- IE43137B1 IE43137B1 IE133676A IE133676A IE43137B1 IE 43137 B1 IE43137 B1 IE 43137B1 IE 133676 A IE133676 A IE 133676A IE 133676 A IE133676 A IE 133676A IE 43137 B1 IE43137 B1 IE 43137B1
- Authority
- IE
- Ireland
- Prior art keywords
- process according
- pentadiene
- methyl
- trihaloethylene
- dihalo
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims abstract description 48
- 238000000034 method Methods 0.000 claims abstract description 40
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims description 20
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 claims description 20
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 239000003999 initiator Substances 0.000 claims description 4
- 238000006317 isomerization reaction Methods 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960002415 trichloroethylene Drugs 0.000 claims 1
- 239000002917 insecticide Substances 0.000 abstract description 2
- -1 methyl pentadienes Chemical class 0.000 abstract description 2
- YYOLVILSZOVWLS-UHFFFAOYSA-N 1,1-dichloro-4-methylpenta-1,3-diene Chemical compound CC(C)=CC=C(Cl)Cl YYOLVILSZOVWLS-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000012263 liquid product Substances 0.000 description 5
- 239000007789 gas Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LLVWLCAZSOLOTF-UHFFFAOYSA-N 1-methyl-4-[1,4,4-tris(4-methylphenyl)buta-1,3-dienyl]benzene Chemical compound C1=CC(C)=CC=C1C(C=1C=CC(C)=CC=1)=CC=C(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LLVWLCAZSOLOTF-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- QVUBZVXSODSSKU-UHFFFAOYSA-N 1,1-dichloro-4-methylpenta-1,4-diene Chemical compound CC(=C)CC=C(Cl)Cl QVUBZVXSODSSKU-UHFFFAOYSA-N 0.000 description 1
- BFNMOMYTTGHNGJ-UHFFFAOYSA-N 2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)CC1C(O)=O BFNMOMYTTGHNGJ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000008246 gaseous mixture Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000009834 vaporization Methods 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
- C07C17/266—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by condensation reactions of hydrocarbons and halogenated hydrocarbons
-
- 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
-
- 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
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB27923/75A GB1531733A (en) | 1975-07-02 | 1975-07-02 | Production of 1,1-dihalo-4-methylpenta-1,3-or 1,4-dienes |
| GB1224776 | 1976-03-26 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE43137L IE43137L (en) | 1977-01-02 |
| IE43137B1 true IE43137B1 (en) | 1980-12-31 |
Family
ID=26248888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE133676A IE43137B1 (en) | 1975-07-02 | 1976-06-21 | Production of 1,1-dihalo-4-methylpenta-1,3-or 1,4-dienes |
Country Status (9)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105646136A (zh) * | 2008-10-13 | 2016-06-08 | 蓝立方知识产权公司 | 用于生产氯化和/或氟化丙烯的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1017159B (de) * | 1952-06-18 | 1957-10-10 | Dow Chemical Co | Verfahren zur Herstellung von 3-Aryl-1, 1-dichlor-2-methylpropenen-1 |
| FR1297752A (fr) * | 1960-03-23 | 1962-07-06 | Stauffer Chemical Co | Procédé de fabrication d'hydrocarbures non saturés chlorés, produits obtenus et leurs applications |
| GB1505584A (en) * | 1975-04-28 | 1978-03-30 | Ici Ltd | Production of 1,1-dichloro-4-methylpenta-1,3-diene by an oxidative coupling process |
-
1976
- 1976-06-21 IE IE133676A patent/IE43137B1/en unknown
- 1976-07-01 FR FR7620117A patent/FR2362102A1/fr not_active Withdrawn
- 1976-07-01 LU LU75277A patent/LU75277A1/xx unknown
- 1976-07-01 NL NL7607264A patent/NL7607264A/xx not_active Application Discontinuation
- 1976-07-01 DK DK297576A patent/DK297576A/da unknown
- 1976-07-01 IT IT2494376A patent/IT1064095B/it active
- 1976-07-02 DE DE19762629868 patent/DE2629868A1/de not_active Withdrawn
- 1976-07-02 CA CA256,214A patent/CA1072126A/en not_active Expired
- 1976-07-02 JP JP7798176A patent/JPS527907A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2362102A1 (fr) | 1978-03-17 |
| AU1523576A (en) | 1978-01-05 |
| IE43137L (en) | 1977-01-02 |
| LU75277A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-07-22 |
| DE2629868A1 (de) | 1977-01-20 |
| JPS527907A (en) | 1977-01-21 |
| CA1072126A (en) | 1980-02-19 |
| DK297576A (da) | 1977-01-03 |
| NL7607264A (nl) | 1977-01-04 |
| IT1064095B (it) | 1985-02-18 |
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