DE2940553C2 - Verfahren zur Herstellung von Monoalkyl-Aromaten - Google Patents
Verfahren zur Herstellung von Monoalkyl-AromatenInfo
- Publication number
- DE2940553C2 DE2940553C2 DE2940553A DE2940553A DE2940553C2 DE 2940553 C2 DE2940553 C2 DE 2940553C2 DE 2940553 A DE2940553 A DE 2940553A DE 2940553 A DE2940553 A DE 2940553A DE 2940553 C2 DE2940553 C2 DE 2940553C2
- Authority
- DE
- Germany
- Prior art keywords
- product
- zone
- aromatic
- transalkylation
- 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.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 238000010555 transalkylation reaction Methods 0.000 claims description 30
- 230000029936 alkylation Effects 0.000 claims description 23
- 238000005804 alkylation reaction Methods 0.000 claims description 23
- 239000000047 product Substances 0.000 claims description 12
- 150000001336 alkenes Chemical class 0.000 claims description 11
- 239000006227 byproduct Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000000926 separation method Methods 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 238000004064 recycling Methods 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 41
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 8
- 239000005977 Ethylene Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 4
- 150000001555 benzenes Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- -1 ethylene, Ethylene Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 229910001510 metal chloride Inorganic materials 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical class Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000010992 reflux Methods 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
- C07C15/067—C8H10 hydrocarbons
- C07C15/073—Ethylbenzene
-
- 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
- C07C6/00—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions
- C07C6/08—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond
- C07C6/12—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring
- C07C6/126—Preparation of hydrocarbons from hydrocarbons containing a different number of carbon atoms by redistribution reactions by conversion at a saturated carbon-to-carbon bond of exclusively hydrocarbons containing a six-membered aromatic ring of more than one hydrocarbon
-
- 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 |
|---|---|---|---|
| US05/950,243 US4179473A (en) | 1978-10-10 | 1978-10-10 | Production of monoalkyl aromatics |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2940553A1 DE2940553A1 (de) | 1980-04-24 |
| DE2940553C2 true DE2940553C2 (de) | 1986-07-17 |
Family
ID=25490155
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2940553A Expired DE2940553C2 (de) | 1978-10-10 | 1979-10-06 | Verfahren zur Herstellung von Monoalkyl-Aromaten |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US4179473A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS5553223A (cg-RX-API-DMAC10.html) |
| DE (1) | DE2940553C2 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2438640B1 (cg-RX-API-DMAC10.html) |
| GB (1) | GB2032946B (cg-RX-API-DMAC10.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3009632A1 (de) * | 1980-03-13 | 1981-09-24 | Basf Ag, 6700 Ludwigshafen | Verfahren zur umsetzung des bei der synthese von ethylbenzol erhaltenen destillationsrueckstandes |
| DE3039760A1 (de) * | 1980-10-22 | 1982-05-27 | Basf Ag, 6700 Ludwigshafen | Verfahren zur kontinuierlichen herstellung von ethylbenzol in heterogener phase |
| US5003119A (en) * | 1988-05-09 | 1991-03-26 | Lummus Crest, Inc. | Manufacture of alkylbenzenes |
| US5227556A (en) * | 1990-04-17 | 1993-07-13 | The Dow Chemical Company | Turbulent flow process, monoalkyl aromatic production process and reactor for such process |
| JPH05506863A (ja) * | 1990-06-08 | 1993-10-07 | エービービー ルーマス クレスト インコーポレイテッド | 触媒スラリーの存在下におけるアルキル交換反応 |
| KR20030037475A (ko) * | 2001-11-05 | 2003-05-14 | 삼성정밀화학 주식회사 | 외부순환식 반응기를 이용한할로히드록시프로필트리알킬암모늄할라이드의 제조방법 |
| KR100559743B1 (ko) | 2004-11-12 | 2006-03-10 | 삼성정밀화학 주식회사 | 농도조절부를 가지는할로히드록시프로필트리알킬암모늄할라이드 제조용 반응기 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2443758A (en) * | 1943-10-07 | 1948-06-22 | Dow Chemical Co | Apparatus for producing alkylated aromatic compounds |
| US2421331A (en) * | 1944-02-29 | 1947-05-27 | Standard Oil Co | Production of alkylaromatics |
| US2747003A (en) * | 1952-06-17 | 1956-05-22 | Phillips Petroleum Co | Method and apparatus for intimately contacting and then separating immiscible fluids |
| US2778862A (en) * | 1953-05-19 | 1957-01-22 | Union Carbide & Carbon Corp | Process for ethylating toluene |
-
1978
- 1978-10-10 US US05/950,243 patent/US4179473A/en not_active Expired - Lifetime
-
1979
- 1979-08-16 GB GB7928578A patent/GB2032946B/en not_active Expired
- 1979-09-07 JP JP11563479A patent/JPS5553223A/ja active Granted
- 1979-10-06 DE DE2940553A patent/DE2940553C2/de not_active Expired
- 1979-10-08 FR FR7924958A patent/FR2438640B1/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5553223A (en) | 1980-04-18 |
| FR2438640B1 (fr) | 1986-08-22 |
| JPS6136729B2 (cg-RX-API-DMAC10.html) | 1986-08-20 |
| US4179473A (en) | 1979-12-18 |
| GB2032946B (en) | 1982-11-03 |
| FR2438640A1 (fr) | 1980-05-09 |
| GB2032946A (en) | 1980-05-14 |
| DE2940553A1 (de) | 1980-04-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |