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Alkylaromatics Production Herstellung Von Alkylaromaten Production De Composes Alkylaromatiques

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Alkylaromatics Production Herstellung Von Alkylaromaten Production De Composes Alkylaromatiques (19) & (11) EP 1 542 947 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C07C 2/66 (2006.01) 13.01.2010 Bulletin 2010/02 (86) International application number: (21) Application number: 03754437.6 PCT/US2003/027581 (22) Date of filing: 04.09.2003 (87) International publication number: WO 2004/026797 (01.04.2004 Gazette 2004/14) (54) ALKYLAROMATICS PRODUCTION HERSTELLUNG VON ALKYLAROMATEN PRODUCTION DE COMPOSES ALKYLAROMATIQUES (84) Designated Contracting States: • SMITH, Charles, M. AT BE BG CH CY CZ DE DK EE ES FI FR GB GR Houston, TX 77005 (US) HU IE IT LI LU MC NL PT RO SE SI SK TR • CIMINI, Ronald, J. Friendswood, TX 77546 (US) (30) Priority: 23.09.2002 US 252767 • MAERZ, Brian Chelmsford, MA (US) (43) Date of publication of application: 22.06.2005 Bulletin 2005/25 (74) Representative: Dew, Melvyn John et al ExxonMobil Chemical Patents Inc., (73) Proprietors: P.O. Box 105 • ExxonMobil Chemical Patents Inc. 1830 Machelen (BE) Bayton, TX 77520 (US) • Washington Group International, Inc. (56) References cited: Boise, FR-A- 2 706 888 US-A- 4 107 224 Idaho 83712 (US) US-A- 5 430 211 US-A- 5 600 048 (72) Inventors: • DATABASE EPODOC [Online] EUROPEAN • CLARK, Michael, C. PATENT OFFICE, THE HAGUE, NL; XP002275731 Pasadena, 77505 Texas (US) & CN 1 051 166 A (CHINA PETROCHEM COR) 8 May 1991 (1991-05-08) Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 1 542 947 B1 Printed by Jouve, 75001 PARIS (FR) 1 EP 1 542 947 B1 2 Description a yield loss, the PEBs are converted back to ethylben- zene by transalkylation with additional benzene, normally Field of the Invention in a separate transalkylation reactor. [0007] By way of example, vapor phase ethylation of [0001] The present invention relates to a process for 5 benzene over the crystalline aluminosilicate zeolite ZSM- producing alkylaromatic compounds, particularly ethyl- 5 is disclosed in U.S. Patent Nos: 4,107,224 (Dwyer), benzene. 3,751,504 (Keown et al.), 3,751,506 (Burress), and 3,755,483 (Burress). Background of the Invention [0008] In most cases, vapor phase ethylation systems 10 use polymer grade ethylene feeds. Moreover, although [0002] Ethylbenzene is a key raw material in the pro- commercial vapor phase processes employing dilute eth- duction of styrene and is produced by the reaction of ylene feeds have been built and are currently in opera- ethylene and benzene in the presence of an acid catalyst. tion, the investment costs associated with these proc- Old ethylbenzene production plants, typically built before esses is high and the products contain high concentra- 15 1980, used AlCl3 or BF3 as the acidic catalyst. Newer tions of xylene impurities. plants have in general been switching to zeolite-based [0009] In recent years the trend in industry has been acidic catalysts. to shift away from vapor phase reactors to liquid phase [0003] Commercial ethylbenzene manufacturing proc- reactors. Liquid phase reactors operate at a temperature esses typically require the use of polymer grade ethylene, of about 220-270°C, which is under the critical tempera- which has a purity exceeding 99.9 mol %. However, the 20 ture of benzene (290°C). One advantage of the liquid purification of ethylene streams to polymer grade is a phase reactor is the very low formation of xylenes and costly process and hence there is considerable interest oligomers. The rate of the ethylation reaction is lower in developing processes that can operate with lower compared with the vapor phase, but the lower design grade ethylene streams. One such ethylene source is temperature of the liquid phase reaction usually econom- the dilute ethylene obtained as an off gas from the fluid 25 ically compensates for the negatives associated with the catalytic cracking or steam cracking unit of a petroleum higher catalyst volume. Thus, due to the kinetics of the refinery which, after removal of reactive impurities, such lower ethylation temperatures, resulting from the liquid as propylene, typically contains about 20-80 wt% ethyl- phase catalyst, the rate of the chain reactions forming ene, with the remainder being ethane together with minor PEBs is considerably lower; about 5-8% of the ethylben- amounts of hydrogen, methane and benzene. 30 zene is converted to PEBs in liquid phase reactions ver- [0004] Three types of ethylation reactor systems are sus the 15-20% converted in vapor phase reactions. used for producing ethylbenzene, namely, vapor phase Hence the stoichiometric excess of benzene in liquid reactor systems, liquid phase reactor systems, and phase systems is typically 150-400%, compared with mixed phase reactor systems. 400-800% in vapor phase systems. [0005] In vapor-phase reactor systems, the ethylation 35 [0010] Liquid phase ethylation of benzene using zeo- reaction of benzene and ethylene is carried out at a tem- lite beta as the catalyst is disclosed in U.S. Patent No. perature of about 380-420°C and a pressure of 9-15 4,891,458 and European Patent Publication Nos. kg/cm2-g in multiple fixed beds of zeolite catalyst. Ethyl- 0432814 and 0629549. More recently it has been dis- ene exothermally reacts with benzene to form ethylben- closed that MCM-22 and its structural analogues have zene, although undesirable chain and side reactions also 40 utility in these alkylation/transalkylation reactions; see, occur. About 15% of the ethylbenzene formed further re- for example, U.S. Patent No. 4,992,606 (MCM-22), U.S. acts with ethylene to form di-ethylbenzene isomers Patent No. 5,258,565 (MCM-36), U.S. Patent No. (DEB), tri-ethylbenzene isomers (TEB) and heavier aro- 5,371,310 (MCM-49), U.S. Patent No. 5,453,554 (MCM- matic products. All these chain reaction products are 56), U.S. Patent No. 5,149,894 (SSZ-25); U.S. Patent commonly referred as polyethylated benzenes (PEBs). 45 No. 6,077,498 (ITQ-1); International Patent Publication In addition to the ethylation reactions, the formation of Nos. WO97/17290 and WO01/21562 (ITQ-2). xylene isomers as trace products occurs by side reac- [0011] Commercial liquid phase ethylbenzene plants tions. This xylene formation in vapor phase processes normally employ polymer grade ethylene. Moreover, al- can yield an ethylbenzene product with about 0.05-0.20 though plants can be designed to accept ethylene wt % of xylenes. The xylenes show up as an impurity in 50 streams containing up to 30 mol% ethane by increasing the subsequent styrene product and are generally con- the operating pressure, the costs associated with the de- sidered undesirable. sign and operation of these plants are significant. [0006] In order to minimize the formation of PEBs, a [0012] Technology has also been developed for the stoichiometric excess of benzene, about 400-900% per production of ethylbenzene in a mixed phase using re- pass, is applied, depending on process optimization. The 55 active distillation. Such a process is described in U.S. effluent from the ethylation reactor contains about 70-85 Patent No. 5,476,978. Mixed phase processes can be wt % of unreacted benzene, about 12-20 wt % of ethyl- used with dilute ethylene streams since the reaction tem- benzene product and about 3-4 wt % of PEBs. To avoid perature of the ethylation reactor is below the dew point 2 3 EP 1 542 947 B1 4 of the dilute ethylene/benzene mixture but well above the [0017] In said one embodiment, said conditions in step bubble point. The diluents of the ethylene feed, ethane, (a) include a temperature of 150 to 270°C and a pressure methane and hydrogen, remain essentially in the vapor of 675 to 8300 kPa. phase. The benzene in the reactor is split between vapor [0018] Conveniently, said alkylation catalyst is select- phase and liquid phase, and the ethylbenzene and PEB 5 ed from MCM-22, PSH-3, SSZ-25, ERB-1, ITQ-1, ITQ- reaction products remain essentially in the liquid phase. 2, MCM-36, MCM-49, MCM-56, faujasite, mordenite and However, reactive distillation units are complex and ex- zeolite beta. pensive and the catalyst is prone to deactivation as a result of the production of ethylene oligomers. Description of the Drawings [0013] U.S. Patent No. 6,252,126 discloses a mixed 10 phase process for producing ethylbenzene by reaction [0019] The accompanying drawing is a flow diagram of a dilute ethylene stream containing 3 to 50 mol% eth- of a process for producing ethylbenzene in accordance ylene with a benzene stream containing 75 to 100 wt% with one example of the invention. benzene. The reaction is conducted in an isothermal ethylation section of a reactor vessel which also includes 15 Detailed Description of the Embodiments a benzene stripping section, where the unreacted ben- zene is thermally stripped from the ethylation products. [0020] The present invention provides a mixed phase Integrated, countercurrent vapor and liquid traffic is main- process for producing alkylaromatic compounds from a tained between the ethylation section and the benzene dilute alkene feedstock, in which the feedstock also in- stripping section. 20 cludes an alkane and typically other impurities. Although the process is particularly directed to the production of Summary of the Invention ethylbenzene from dilute ethylene, it is equally applicable to the production of other C2-C6 alkylaromatic com- [0014] The present invention resides in a process for pounds, such as cumene, as well as C6+ alkylaromatics, 25 producing an alkylaromatic compound by reacting an such as C8-C16 linear alkylbenzenes.
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