DE1618966B1 - Verfahren zum Herstellen von 1,2,4-Trimethyl-5-alkylbenzolen - Google Patents
Verfahren zum Herstellen von 1,2,4-Trimethyl-5-alkylbenzolenInfo
- Publication number
- DE1618966B1 DE1618966B1 DE1967S0112418 DES0112418A DE1618966B1 DE 1618966 B1 DE1618966 B1 DE 1618966B1 DE 1967S0112418 DE1967S0112418 DE 1967S0112418 DE S0112418 A DES0112418 A DE S0112418A DE 1618966 B1 DE1618966 B1 DE 1618966B1
- Authority
- DE
- Germany
- Prior art keywords
- pseudocumene
- trimethyl
- reaction
- propene
- alkylation
- 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 13
- GWHJZXXIDMPWGX-UHFFFAOYSA-N 1,2,4-trimethylbenzene Chemical compound CC1=CC=C(C)C(C)=C1 GWHJZXXIDMPWGX-UHFFFAOYSA-N 0.000 claims description 58
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 23
- 238000006243 chemical reaction Methods 0.000 claims description 11
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 230000029936 alkylation Effects 0.000 claims description 9
- 238000005804 alkylation reaction Methods 0.000 claims description 9
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000004821 distillation Methods 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000011541 reaction mixture Substances 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims 4
- 239000005977 Ethylene Substances 0.000 claims 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 150000001336 alkenes Chemical class 0.000 claims 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 3
- POOXAYBPGIHSME-UHFFFAOYSA-N 1,2,4-trimethyl-5-propan-2-ylbenzene Chemical compound CC(C)C1=CC(C)=C(C)C=C1C POOXAYBPGIHSME-UHFFFAOYSA-N 0.000 claims 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- 238000006317 isomerization reaction Methods 0.000 claims 2
- XCYJPXQACVEIOS-UHFFFAOYSA-N 1-isopropyl-3-methylbenzene Chemical compound CC(C)C1=CC=CC(C)=C1 XCYJPXQACVEIOS-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 claims 1
- 150000001555 benzenes Chemical class 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000003245 coal Substances 0.000 claims 1
- 238000010908 decantation Methods 0.000 claims 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- QHOPYXBAXVDHDW-UHFFFAOYSA-N 1,2,3-trimethyl-4-propan-2-ylbenzene Chemical class CC(C)C1=CC=C(C)C(C)=C1C QHOPYXBAXVDHDW-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- -1 aluminum chloride-pseudocumene Chemical group 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C15/00—Cyclic hydrocarbons containing only six-membered aromatic rings as cyclic parts
- C07C15/02—Monocyclic hydrocarbons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/54—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition of unsaturated hydrocarbons to saturated hydrocarbons or to hydrocarbons containing a six-membered aromatic ring with no unsaturation outside the aromatic ring
- C07C2/64—Addition to a carbon atom of a six-membered aromatic ring
- C07C2/66—Catalytic processes
- C07C2/68—Catalytic processes with halides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2527/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- C07C2527/06—Halogens; Compounds thereof
- C07C2527/125—Compounds comprising a halogen and scandium, yttrium, aluminium, gallium, indium or thallium
- C07C2527/126—Aluminium chloride
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 |
|---|---|---|---|
| FR107630A FR1531632A (fr) | 1967-05-24 | 1967-05-24 | Procédé d'alkylation du pseudocumène |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1618966B1 true DE1618966B1 (de) | 1972-05-25 |
Family
ID=8631480
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967S0112418 Pending DE1618966B1 (de) | 1967-05-24 | 1967-10-16 | Verfahren zum Herstellen von 1,2,4-Trimethyl-5-alkylbenzolen |
Country Status (6)
| Country | Link |
|---|---|
| BE (1) | BE705179A (enrdf_load_stackoverflow) |
| DE (1) | DE1618966B1 (enrdf_load_stackoverflow) |
| FR (1) | FR1531632A (enrdf_load_stackoverflow) |
| GB (1) | GB1164210A (enrdf_load_stackoverflow) |
| LU (1) | LU54644A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6715441A (enrdf_load_stackoverflow) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412595A (en) * | 1942-03-03 | 1946-12-17 | Phillips Petroleum Co | Process for reaction of aromatic hydrocarbons with normally gaseous unsaturated hydrocarbons |
| US2837584A (en) * | 1955-10-31 | 1958-06-03 | Standard Oil Co | Process for production of durene |
| US3132189A (en) * | 1961-07-17 | 1964-05-05 | Marathon Oil Co | Preparation of 1, 2, 4, 5-tetrallkylbenzenes from pseudocumene and propylene |
| FR1460349A (fr) * | 1964-12-18 | 1966-11-25 | Gelsenberg Benzin Ag | Procédé de préparation de triméthyl-1,2,4-isopropyl-5-benzène |
-
1967
- 1967-05-24 FR FR107630A patent/FR1531632A/fr not_active Expired
- 1967-10-10 LU LU54644D patent/LU54644A1/xx unknown
- 1967-10-16 DE DE1967S0112418 patent/DE1618966B1/de active Pending
- 1967-10-16 BE BE705179D patent/BE705179A/xx unknown
- 1967-10-24 GB GB4819867A patent/GB1164210A/en not_active Expired
- 1967-11-14 NL NL6715441A patent/NL6715441A/xx unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2412595A (en) * | 1942-03-03 | 1946-12-17 | Phillips Petroleum Co | Process for reaction of aromatic hydrocarbons with normally gaseous unsaturated hydrocarbons |
| US2837584A (en) * | 1955-10-31 | 1958-06-03 | Standard Oil Co | Process for production of durene |
| US3132189A (en) * | 1961-07-17 | 1964-05-05 | Marathon Oil Co | Preparation of 1, 2, 4, 5-tetrallkylbenzenes from pseudocumene and propylene |
| FR1460349A (fr) * | 1964-12-18 | 1966-11-25 | Gelsenberg Benzin Ag | Procédé de préparation de triméthyl-1,2,4-isopropyl-5-benzène |
Also Published As
| Publication number | Publication date |
|---|---|
| LU54644A1 (enrdf_load_stackoverflow) | 1967-12-11 |
| NL6715441A (enrdf_load_stackoverflow) | 1968-11-25 |
| GB1164210A (en) | 1969-09-17 |
| FR1531632A (fr) | 1968-07-05 |
| BE705179A (enrdf_load_stackoverflow) | 1968-03-01 |
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