FR2706888A1 - Process for the alkylation of aromatic compounds - Google Patents
Process for the alkylation of aromatic compounds Download PDFInfo
- Publication number
- FR2706888A1 FR2706888A1 FR9307878A FR9307878A FR2706888A1 FR 2706888 A1 FR2706888 A1 FR 2706888A1 FR 9307878 A FR9307878 A FR 9307878A FR 9307878 A FR9307878 A FR 9307878A FR 2706888 A1 FR2706888 A1 FR 2706888A1
- Authority
- FR
- France
- Prior art keywords
- zone
- compounds
- effluent
- liquid effluent
- benzene
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 238000005804 alkylation reaction Methods 0.000 title claims abstract description 12
- 230000029936 alkylation Effects 0.000 title claims description 9
- 150000001491 aromatic compounds Chemical class 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 75
- 150000001875 compounds Chemical class 0.000 claims abstract description 43
- 239000007788 liquid Substances 0.000 claims abstract description 43
- 238000006243 chemical reaction Methods 0.000 claims abstract description 28
- 238000000926 separation method Methods 0.000 claims abstract description 15
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims abstract description 12
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 11
- 238000004064 recycling Methods 0.000 claims abstract description 11
- 150000001336 alkenes Chemical class 0.000 claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 239000010457 zeolite Substances 0.000 claims description 18
- 229910021536 Zeolite Inorganic materials 0.000 claims description 17
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims description 17
- 238000010926 purge Methods 0.000 claims description 6
- 239000000945 filler Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000011159 matrix material Substances 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 5
- 229930195733 hydrocarbon Natural products 0.000 abstract description 5
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 abstract description 5
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000010555 transalkylation reaction Methods 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 229910052810 boron oxide Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- JKWMSGQKBLHBQQ-UHFFFAOYSA-N diboron trioxide Chemical compound O=BOB=O JKWMSGQKBLHBQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000001125 extrusion Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000005673 monoalkenes Chemical class 0.000 description 1
- 238000005453 pelletization Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/08—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of the faujasite type, e.g. type X or Y
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)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9307878A FR2706888A1 (en) | 1993-06-25 | 1993-06-25 | Process for the alkylation of aromatic compounds |
| CN94108918A CN1043879C (zh) | 1993-06-25 | 1994-06-24 | 芳烃的烷基化方法 |
| JP6142101A JPH0748291A (ja) | 1993-06-25 | 1994-06-24 | 芳香族のアルキル化方法 |
| KR1019940014719A KR950000635A (ko) | 1993-06-25 | 1994-06-25 | 방향족 화합물의 알킬화 방법 |
| TW083106094A TW363953B (en) | 1993-06-25 | 1994-07-04 | Aromatic alkylation process |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9307878A FR2706888A1 (en) | 1993-06-25 | 1993-06-25 | Process for the alkylation of aromatic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2706888A1 true FR2706888A1 (en) | 1994-12-30 |
| FR2706888B1 FR2706888B1 (enrdf_load_stackoverflow) | 1995-10-20 |
Family
ID=9448653
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR9307878A Granted FR2706888A1 (en) | 1993-06-25 | 1993-06-25 | Process for the alkylation of aromatic compounds |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPH0748291A (enrdf_load_stackoverflow) |
| KR (1) | KR950000635A (enrdf_load_stackoverflow) |
| CN (1) | CN1043879C (enrdf_load_stackoverflow) |
| FR (1) | FR2706888A1 (enrdf_load_stackoverflow) |
| TW (1) | TW363953B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004026797A3 (en) * | 2002-09-23 | 2004-05-27 | Exxon Mobil Chem Patents Inc | Alkylaromatics production |
| US7425659B2 (en) | 2006-01-31 | 2008-09-16 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US7501547B2 (en) | 2006-05-10 | 2009-03-10 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| CN115138302A (zh) * | 2021-03-31 | 2022-10-04 | 中国石油天然气股份有限公司 | 液体酸烷基化反应工艺及反应系统 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100225625B1 (ko) * | 1996-02-27 | 1999-10-15 | 윤종용 | 전자렌지의 음식물 가열온도 제어장치 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2756221A1 (de) * | 1977-02-11 | 1978-08-17 | Mobil Oil Corp | Verfahren zur aethylierung von benzol |
| FR2662438A1 (fr) * | 1990-05-22 | 1991-11-29 | Inst Francais Du Petrole | Procede de production d'alkylbenzenes utilisant des catalyseurs a base de zeolithe y desaluminee. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4079093A (en) * | 1977-05-31 | 1978-03-14 | Uop Inc. | Aromatic hydrocarbon alkylation process |
| US4237328A (en) * | 1979-10-09 | 1980-12-02 | Uop Inc. | Process for HF-catalyzed alkylation of aromatic hydrocarbons |
| US4503277A (en) * | 1983-11-30 | 1985-03-05 | Uop Inc. | HF regeneration in aromatic hydrocarbon alkylation process |
-
1993
- 1993-06-25 FR FR9307878A patent/FR2706888A1/fr active Granted
-
1994
- 1994-06-24 JP JP6142101A patent/JPH0748291A/ja not_active Withdrawn
- 1994-06-24 CN CN94108918A patent/CN1043879C/zh not_active Expired - Fee Related
- 1994-06-25 KR KR1019940014719A patent/KR950000635A/ko not_active Ceased
- 1994-07-04 TW TW083106094A patent/TW363953B/zh active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2756221A1 (de) * | 1977-02-11 | 1978-08-17 | Mobil Oil Corp | Verfahren zur aethylierung von benzol |
| FR2662438A1 (fr) * | 1990-05-22 | 1991-11-29 | Inst Francais Du Petrole | Procede de production d'alkylbenzenes utilisant des catalyseurs a base de zeolithe y desaluminee. |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004026797A3 (en) * | 2002-09-23 | 2004-05-27 | Exxon Mobil Chem Patents Inc | Alkylaromatics production |
| US6995295B2 (en) | 2002-09-23 | 2006-02-07 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US7425659B2 (en) | 2006-01-31 | 2008-09-16 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US7803976B2 (en) | 2006-01-31 | 2010-09-28 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US7501547B2 (en) | 2006-05-10 | 2009-03-10 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| US7772448B2 (en) | 2006-05-10 | 2010-08-10 | Badger Licensing Llc | Alkylaromatics production |
| US7868218B2 (en) | 2006-05-10 | 2011-01-11 | Exxonmobil Chemical Patents Inc. | Alkylaromatics production |
| CN115138302A (zh) * | 2021-03-31 | 2022-10-04 | 中国石油天然气股份有限公司 | 液体酸烷基化反应工艺及反应系统 |
Also Published As
| Publication number | Publication date |
|---|---|
| KR950000635A (ko) | 1995-01-03 |
| TW363953B (en) | 1999-07-11 |
| CN1043879C (zh) | 1999-06-30 |
| FR2706888B1 (enrdf_load_stackoverflow) | 1995-10-20 |
| CN1106369A (zh) | 1995-08-09 |
| JPH0748291A (ja) | 1995-02-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5981819A (en) | Process of generating C3 - and C4 -olefins from a feed mixture containing C4 to C7 olefins | |
| CA2043026C (fr) | Procede de production d'alkylbenzenes utilisant des catalyseurs a base de zeolithe y desaluminee | |
| EP0402202B1 (fr) | Procédé de production d'alkylbenzènes utilisant un catalyseur à base de zéolithe Y désaluminée et un catalyseur à base de mordenité désaluminée | |
| JP3844734B2 (ja) | メタノールからプロピレンを製造する方法 | |
| DE60123694T2 (de) | Integriertes Hydroisomerizierungs- und Alkylierungsverfahren | |
| JP4637434B2 (ja) | 炭化水素からｃ２−及びｃ３−オレフィンを製造する方法 | |
| JPH01284586A (ja) | エチレンとアセチレンとガソリンを含む通常ガス状の原料の液相における選択的接触水素添加法 | |
| NO831758L (no) | Fremgangsmaate for fremstilling av tert. butylalkyletere og buten-1. | |
| CN103140458A (zh) | 由异丁醇制造烯烃的组合方法 | |
| JPS62230885A (ja) | ガソリンの製造方法 | |
| FR2757533A1 (fr) | Procede de preparation d'une matiere premiere de melange pour essence exempte de benzene et isomerisee utlisant un catalyseur a double fonction | |
| CA1150178A (fr) | Procede de valorisation des coupes c.sub.4 olefiniques | |
| FR2706888A1 (en) | Process for the alkylation of aromatic compounds | |
| FR2697246A1 (fr) | Procédé de production de phénylalcanes utilisant un catalyseur à base de zéolithe Y modifiée. | |
| EP1456155B1 (fr) | Procede de production de phenylalcanes utilisant une combinaison de deux catalyseurs | |
| US9227885B2 (en) | Process to make olefins from isobutanol | |
| Schaap et al. | The Potassium-catalyzed Reaction of Olefins with Arylalkanes1 | |
| CN1463290A (zh) | 由气态烃类原料生产汽油的方法 | |
| FR2662438A1 (fr) | Procede de production d'alkylbenzenes utilisant des catalyseurs a base de zeolithe y desaluminee. | |
| Badger et al. | 51. The formation of aromatic hydrocarbons at high temperatures. Part VI. The pyrolysis of tetralin | |
| CN103889935A (zh) | 用于制备乙烯和/或丙烯以及异烯烃贫化的烯烃产物的方法 | |
| US3168591A (en) | Alkylation process | |
| US20150183696A1 (en) | Naphthalene-Depleted Fluids | |
| JP4458766B2 (ja) | オレフィンオリゴマーの製造方法 | |
| US3860497A (en) | Multi-stage distillation of bicycloheptadiene |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |
Effective date: 20100226 |