MXPA99003167A - Process for the preparation of monoalkylated aromatic compounds - Google Patents

Abstract

Se describe un proceso para preparar compuestos aromáticos monoalquilados el cual comprende someter un hidrocarburo aromático a alquilación con una olefina que contiene desde 2 hasta 4átomos de carbono, o a transalquilación con un hidrocarburo polialquilaromático, en presencia de zeolita ERS-10.

Description

PROCESS FOR THE PREPARATION OF MONO MOUNTED AROMATIC COMPOUNDS DESCRIPTION OF THE INVENTION A process for preparing monoalkylated aromatics is described, which comprises subjecting an aromatic hydrocarbon to alkylation with an olefin containing from 2 to 4 carbon atoms, or to transalkylation with a polyalkylaromatic hydrocarbon, in the presence of zeolite ERS-10. The above processes, still widely used in the petrochemical industry, for the production of alkylaromatic substances, in particular eumeno and ethylbenzene, comprise the use of a catalyst based on phosphoric acid and infusoria earth, in a fixed bed, for eumeno and A1C13, in suspension, for ethylbenzene and eumeno. However, with these processes there are problems in relation to environmental impact and safety; in fact, the use of these catalysts is particularly problematic due to corrosion, the concomitant production of toxic organic products and the disposal of spent catalysts. The possibility of replacing these catalysts with non-polluting, non-corrosive and regenerable materials such as, for example, zeolitic catalysts, has been known for some time. The use of X and Y zeolites for the preparation of eumeno was first described in 1965 (Minachev, Kr., Isakov, Ya.

I., Garanin, V.I., Piguzova, L.I. Bogomov, V.I., and Vitukina, A.S., Neftekhimiya 5 (1965) 676). Subsequently, Venuto et al. (Venuto, PB, Hamilton, LA, Landis, PS, and ise, JJ, J. Catal. 5 (1966) 81) described the alkylation of benzene with light olefins, such as propylene and ethylene, catalyzed by zeolites with a faujasitic structure. (X and Y), and therefore with wide pores. These zeolites can be stabilized by exchange with rare earth. US Pat. No. 3,251,897 describes the alkylation of aromatic substances in the liquid phase, catalyzed by crystalline porous alumino-silicate, among which are X, Y and mordenite. The North American document 4,292,458 describes the use of zeolites type ZSM-5, in particular boralite with the structure type ZSM-5 capable of catalyzing the alkylation of benzene with propylene. However, this type of zeolitic system, perhaps due to the channels which are too small, only allows the production of eumeno with rather low selectivities. In general, it is therefore stated that zeolites are active in the alkylation of aromatic substances with olefins, but have a different behavior with respect to selectivity. The alkylation reaction, in fact, is accompanied by successive side reactions, such as polyalkylation, and parallel reactions such as olefomerization of olefins. Then, the oligomers can in turn rent the aromatic substances which gives rise to heavy alkylated products or that undergo fractionation or cracking to provide light olefins, different from the main reactant and thus produce, by successive alkylation, other alkylated by-products. Monoalkylated hydrocarbon preparations by the transalkylation of polyalkylated aromatic hydrocarbons which use zeolites with small, medium and large pore sizes are described, for example, in US documents 3,385,906, 4,169,111 and EP 308097. In particular, the reaction of Transalkylation of polyalkylated aromatic hydrocarbons can be carried out appropriately subsequent to the alkylation step, by operating on polyalkylated products recovered downstream of the alkylation. The use of zeolitic catalysts to prepare monoalkylated aromatic hydrocarbons by the transalkylation of polyalkylated products in a step subsequent to the alkylation step is described in US documents 3,385,906, 4,774,377, 4,168,111 and EP 308097, where alkylation and transalkylation processes are combined to obtain better yields for monoalkylated aromatic substances. The documents EP 432,814, EP 439,632, EP 629599 and EP 687500 describe the production of monoalkylated aromatic hydrocarbons from aromatic hydrocarbons by alkylation, transalkylation and a combined process of alkylation and transalkylation, catalyzed by beta zeolite.

A process for preparing monoalkylated aromatic compounds has now been found which comprises subjecting an aromatic hydrocarbon to alkylation with an olefin containing from 2 to 4 carbon atoms, or to transalkylation with a polyalkylaromatic hydrocarbon in the presence of a catalyst containing zeolite ERS-10. . Better results are obtained with the present invention in terms of selectivity to the monoalkylation product in the alkylation process, in particular, there is low formation of heavy products (dialkylated products) and n-propylbenzene. The zeolite ERS-10 is a porous crystalline material described in EP 796821, which has a molar composition of oxides in its calcined and anhydrous form, corresponding to the following formula: where m is a number between 0.01 and 10, M is H + and / or a cation of an alkaline or alkaline earth metal with a valence n, z is a number between 0 and 0.02, X represents one or more elements that are selected from aluminum , iron, gallium, boron, vanadium, arsenic, antimony, chromium and manganese, and Y represents one or more elements that is selected from silicon, germanium, titanium, zirconium, characterized by the following X-ray diffraction spectrum from powders (recorded by means of a vertical goniometer equipped with an electronic pulse counting system and using CuKa (? = 1.54178 A) containing the main reflections indicated in Table A: Table A where d indicates the interplane distance, I / In * 100 represents the relative intensity calculated by measuring the height of the peaks and relating percentage with the weight of the most intense peak, the symbol vs indicates a very strong intensity (60-100), s a strong intensity (40-60), m an average intensity (20-40) and w a weak intensity (0-20). M is preferably selected from sodium, potassium, hydrogen or mixtures thereof. According to a particularly preferred aspect of the present invention, the ERS-10 zeolite is in the acid form, ie, in the form in which the M cationic sites of the zeolite are predominantly occupied by hydrogen ions. It is especially preferable that at least 80% of the cationic sites are occupied by hydrogen ions. X is preferably aluminum and Y is preferably silicon. The zeolite can be used as such or can be extruded with suitable inorganic bonding oxides to form cylindrical or spherical granules, or granules with other commonly used forms. For example, the ligands may be aluminas, silicones, silicoalumines, and clays. Alumina is preferably used. The final catalyst contains from 10 to 90%, preferably from 20 to 80% by weight of ERS-10 zeolite. The aromatic hydrocarbons which may be alkylated or transalkylated according to the present invention are benzene, toluene, xylene and mixtures thereof. The aromatic hydrocarbon is preferably benzene. The olefins which are used for the alkylation of aromatic hydrocarbons according to the present invention are olefins containing 2 to 4 carbon atoms, preferably ethylene or propylene. The olefins are pure or mixed with C2-C4 paraffins, but preferably without dienes, acetylenes, sulfur compounds or nitrogen-containing compounds, which can deactivate the catalyst. The polyalkylated aromatic hydrocarbons which may be used for transalkylation are those which contain two or more alkyl groups, each of which may have from 2 to 4 carbon atoms. Preferably they are of alkylbenzene such as diethylbenzenes or diisopropylbenzenes.

The reaction products which can preferably be prepared with the process of the present invention are ethylbenzenes obtained by reaction of benzene with ethylene or polyethylbenzenes, preferably diethylbenzenes and eumeno by the reaction of benzene with propylenes or with polyisopropylbecenes, preferably diisopropylbenzenes. The alkylation reaction can be carried out industrially in a continuous, semi-continuous or batchwise manner, and in the gas phase, in the liquid phase or in the mixed phase.; In order to maintain the temperature within a preferred range and reduce the alternating production of aromatic polyalkylated products, the catalyst can be placed in various layers in the reactor. A suspension is made between one layer and another with inert solvents and / or part of the aromatic substance and / or part of the olefin. Under suitable conditions, high proportions of aromatic / olefin substance can be obtained on a single layer, without increasing the total proportion, with the evident advantage of subsequent separation and recycling of the aromatic substances. The temperature control can be carried out either by suspension of reagents and / or inert products, or by intercooling between layers, for example, by insertion of refrigerants. The alkylation reaction can be carried out appropriately in two or more reactors in series, intercooled to control the temperature. The olefin feed can be suitably distributed between the various reactors and the reactor layers, optionally by diluting the olefin itself with an aromatic or inert product to promote temperature control. The olefin feed is such an amount as to obtain a molar ratio [aromatic substance] / [olefin] ranging from 1 to 20, preferably between 2 and 8. The reaction temperature varies from 100 ° C to 300 ° C, preferably between 120 ° C and 230 ° C; the pressure varies from 10 atm to 50 atm, preferably from 20 atm to 45 atm; the space velocity WHSV varies from 0.1 200 hours "1, preferably between 1 and 10 hours" 1. A combination of temperature and pressure conditions is preferably selected so as to ensure that the alkylation reaction takes place at least partially in the liquid phase, and even more preferably substantially in the liquid phase. The transalkylation reaction is carried out at a temperature ranging from 100 to 350 ° C at a pressure ranging from 10 to 50 atm and a WHSV ranging from 0.01 to 200 hours "1. The temperature preferably is between 150 and 300 ° C, the pressure between 20 and 45 atm and the WHSV between 0.1 and 10 hours "1. The transalkylation reaction is preferably carried out under such conditions that it takes place at least partially in the liquid phase, even more preferably under such conditions that it takes place substantially in the liquid phase. The molar ratio between aromatic hydrocarbon and polyalkylaromatic hydrocarbon can vary from 1 to 30, preferably from 1 to 10. According to a preferred aspect in order to maximize the production of monoalkylated product in the reaction of aromatic substances with light olefins, and in Particular benzene with ethylene to provide ethylbenzene and benzene with propylene to provide eumeno, the transalkylation activity of the zeolite ERS-10 can be carried out in the same reactor in which the alkylation process takes place, where, with a time of sufficient residence, the amount of polyalkylated side products can be reduced with respect to the monoalkylated product. According to another aspect of the present invention, to obtain better yields of monoalkylated product, the product obtained in the alkylation can be separated into: (a) an aromatic hydrocarbon fraction, (b) a monoalkylated aromatic fraction, and ( c) a fraction of polyalkylated substances and this last fraction is fed back to the alkylation reactor where it undergoes the transalkylation reaction to provide the monoalkylated product. According to a preferred aspect of the present invention, the fraction of polyalkylated aromatic substances (c) is subjected to transalkylation in a specific reactor, where it is contacted with an aromatic hydrocarbon feed, in the presence of the catalyst containing zeolite ERS -10. For example, the fraction of "eumune residues" produced in the alkylation process to provide eumeno can be used as a polyalkylated aromatic hydrocarbon consisting predominantly of diisopropylbenzenes. A further aspect of the present invention, therefore, relates to a process for the preparation of mono-alkylated aromatic hydrocarbons, which comprises: 1) placing an aromatic hydrocarbon in contact with a C2-C4 olefin, under alkylation conditions, in the presence of a catalyst containing zeolite ERS-10, 2) separate the product obtained in part (a), a fraction containing an aromatic hydrocarbon, (b) a fraction containing a monoalkylated aromatic hydrocarbon and (c) a fraction containing polyalkylated aromatic hydrocarbons, 3) placing the fraction (c) containing polyalkylated aromatic hydrocarbons in contact with an aromatic hydrocarbon, under transalkylation conditions, in the presence of ERS-10 zeolite. Steps 1) and 3) are preferably carried out under partially liquid phase conditions, even more preferably under substantially liquid phase conditions.

EXAMPLE 1 (Preparation of zeolite ERS-10) .4 g of tetraethylorthosilicate are added with stirring to a solution consisting of 45 g of demineralised water, 0.204 g of aluminum isopropylate, 0.19 g of sodium hydroxide and 1.71 g of 6-azoniaspyrroxide hydroxide (5, 5). ) -undecano (Q). These operations are carried out at room temperature. When the hydrolysis is complete, an opalescent solution is obtained, which has the following composition, expressed as molar proportions: Si02 / Al203 = 100/1 Na + / Si02 = .0.095 / 1 Q / Si02 = 0.2 / 1 H20 / Si02 = 50/1 0H "/ Si02 = 0.295.

The solution is then loaded in a steel autoclave, placed in an oven and maintained at 170 ° C, under autogenous pressure, for 14 days. After cooling to room temperature, the crystalline product is separated from the mother liquor by filtration, washed with demineralized water and dried in an oven at 120 ° C for 2 hours. The composition of the crystalline material, determined by elemental chemical analysis, is the following: 67 Si02: 1 A1203: 0.5 Q20: 0.3 Na20: 7 H20 The material obtained is a crystalline aluminosilicate having an X-ray diffraction pattern (performed with a vertical goniometer equipped with an electronic pulse counting system using CuK radiation? = 1.544178 Á) as described in EP 796821, example 1, table 3. The sample is then calcined at 550 ° C for 5 hours in an air stream. The chemical analysis shows the following composition: 67 SiO ,: 1 To 2.VO3 0.3 Na20 The X-ray diffraction spectrum from the powders in relation to this sample in acid form is that indicated in EP 796821, example 1, table 4. The calcined product is subsequently subjected to an acid exchange process by repeated treatment with an ammonium acetate solution at 80 ° C, washed with demineralized water and calcinated at 550 ° C for 5 hours. The sample obtained in this manner has a residual Na content of less than 100 ppm.

EXAMPLE 2 (Alkylation test: synthesis of eumeno) The catalyst of the ERS-10 powder form obtained in Example 1 is manufactured into tablets, sieved into particles having 20-40 mesh dimensions and tested in an alkylation process of benzene with propylene to provide eumeno. 3.0 g of this catalyst is charged to a fixed-bed reactor having a diameter of 1.2 cm and equipped with a container with an internal thermometer into which the thermocouple for temperature control is inserted. The reactor is immersed in a heated oil bath to obtain better temperature control. The catalyst is first activated in nitrogen at 180 ° C to eliminate any residual traces of moisture present therein. The conditions adopted for the alkylation test are: molar ratio of benzene / propylene = 7/1 temperature = 150 ° C pressure = 38 bar WHSV = 1 hour "1 The products were analyzed using a gas chromatograph (Hewlett-Packard 5890 equipped with FID analyzer) having a PONA capillary column (50 m x 0.21 mm x 0.5 μm). The following table 1 indicates the results of the test: steam time (hours) 22.5 propylene conversion (%) 99.3 distribution of standardized products with respect to benzene (% by weight) oligomers 0.25 eumeno 92.64 n-propylbenzene (ppm / cumene) 158 diisopropylbenzene (DIPB) 5.88 other 0.92 selectivity (C9 / C6) 94.82 (C9 / C3) 89.52 (IPB / C3) 97.93 where : (C9 / C6) = selectivity to eumeno in reference to benzene (C9 / C3) = selectivity to eumeno in reference to propylene (IPB / C3) = selectivity to isopropylbenzene (IPB) (eumeno, diisopropilbenzene) in reference to propylene.

EXAMPLE 3 (alkylation test: eumeno synthesis) Example 2 is repeated under the following conditions: molar ratio of benzene / propylene 7/1 temperature = 170 ° C pressure = 38 bar WHSV = 1 hour "1 Table 2 below indicates the results of the test: steam time (hours) 22.5 propylene conversion (%) 99.5 distribution of standardized products with respect to benzene (% by weight) oligomers 0.23 eumeno 88.34 n-propylbenzene (ppm / cumeo 265 diisopropylbenzene (DIPB) 10.45 other 0.77 selectivity (% ¡(C9 / C6) 91.37 (C9 / C3) 83.71 (IPB / C3) 98.68 EXAMPLE 4 Example 2 is repeated under the following conditions molar ratio of benzene / propylene 7/1 temperature = 185 ° C pressure = 38 bar WHSV = 1 hour "1 Table 3 below indicates the results of the test: steam time (hours) 87.5 propylene conversion (% ', 99.5 distribution of standardized products with respect to benzene (% by weight) oligomers 0. 21 eumeno 86. 61 n-propylbenzene (ppm / eumeno) 360 diisopropylbenzene (DIPB) 12.3 other 0.68 selectivity (%) (C9 / C6) 89.98 (C9 / C3) 81.43 (IPB / C3) 98.56 EXAMPLE 5 (comparative) It was repeated in Example 2 using as catalyst a USY zeolite (330 HUA from Tosoh Corporation) under the following conditions: charged catalyst = 3.0 g molar ratio of benzene / propylene 7/1 temperature = 150 ° C pressure = 38 bar WHSV = 1 hour "1 Table 4 below indicates the results of the test: propylene conversion (%) 98.1 distribution of standardized products with respect to benzene (% by weight) oligomers 0.33 eumeno 73.05 n-propylbenzene (ppm / eumeno! 170 diisopropylbenzene (DIPB) 21.88 other 4.51 selectivity (%) (C9 / C6) 79.36 (C9 / C3) 63.69 (IPB / C3) 91.93 When comparing these results with those obtained, under the same operating conditions in example 2, it can be observed that zeolite ERS-10 has a much higher selectivity for eumeno than zeolite Y, with respect to both benzene and propylene . It should also be noted that both in example 2 and comparative example 5, the conversion of propylene is total and as regards the production of isopropylbenzenes (IPB), the values obtained with zeolite ERS-10 are much higher than those obtained with zeolite Y.

EXAMPLE 6 (comparative) Example 2 was repeated using a CBV40 mordenite (PQ Corporation) as a catalyst under the following conditions: charged catalyst = 3.0 g molar ratio of benzene / propylene 7/1 temperature = 150 ° C pressure = 38 bar WHSV = 1 hour "1 Table 5 below indicates the results of the test: propylene conversion (% ¡99.8 distribution of standardized products with respect to benzene (% by weight) oligomers 0.31 eumeno 89.1 n-propylbenzene (ppm / eumeno) 163 diisopropylbenzene (DIPB) 10.58 other 0.33 selectivity (% 1 (C9 / C6) 91. 85 (C9 / C3) 84. 25 (IPB / C3) 99. 05 When comparing these results with those obtained, under the same operating conditions, in example 2, it can be observed that zeolite ERS-10 has a much higher selectivity to eumeno than mordenite, with respect to both benzene and propylene. Furthermore, in this case, it can be noted that both in example 2 and comparative example 6, the conversion of propylene is total as regards the production of isopropylbenzene (IPB), the values obtained with zeolite ERS-10 they are much higher than those obtained with mordenite. Therefore, it can generally be asserted that zeolite ERS-10 results in a higher production of eumeno and a lower formation of by-products such as diisopropylbenzenes, oligomers and n-propylbenzenes.

EXAMPLE 7 - (transalkylation catalytic test) A transalkylation test was carried out using the ERS-10 catalyst prepared as described in Example 1, transformed into granules having 20-40 mesh dimensions. The test is carried out in a fixed bed plant in a continuous manner where 2.0 g of catalyst are loaded. The feed liquid consists of a mixture of benzene (80% by weight) and 1,3-diisopropylbenzene (20% by weight). The reaction conditions are the following: temperature = 200, 220 and 240 ° C pressure = 50 bar WHSV = 5 hours "1 The results of the test are indicated in table 1 TABLE 1

Claims (35)

1. CLAIMS 1. A process for the alkylation of aromatic hydrocarbons, characterized in that it comprises placing the aromatic hydrocarbon in contact with an olefin containing from 2 to 4 carbon atoms, in the presence of a catalyst comprising zeolite ERS-10.
2. 2. The process according to claim 1, characterized in that it is carried out at a temperature ranging from 100 to 300 ° C, at a pressure varying from 10 to 50 atm, at a space velocity WHSV ranging from 0.1 to 200. hours "1 and with a molar ratio of [aromatic compound] / [olefin] ranging from 1 to 20.
3. 3. The process according to claim 2, characterized in that the temperature is between 120 and 230 ° C, the pressure is between 20 and 45 atm, the space velocity WHSV is between 1 and 10 hours "1, and the molar ratio between the aromatic compound and the olefin is between 2 and 8.
4. 4. The process according to claims 1 to 3, characterized in that it comprises placing the aromatic hydrocarbon in contact with an olefin under conditions at least partially liquid phase.
5. 5. The process according to claim 4, characterized in that it comprises placing the aromatic hydrocarbon in contact with an olefin under conditions in substantially liquid phase.
6. 6. The process according to claim 1, characterized in that the cationic sites in the zeolite ERS-10 are occupied predominantly by hydrogen ions.
7. 7. The process according to claim ß, characterized in that at least 80% of the cationic sites are occupied by hydrogen ions.
8. 8. The process according to claim 1, characterized in that the ERS-10 zeolite is based on aluminum and silicon oxides.
9. 9. The process according to claim 1, characterized in that the ERS-10 zeolite is combined with an inorganic oxide as a ligand.
10. 10. The process according to claim 9, characterized in that the inorganic oxide is alumina.
11. 11. The process according to claim 9, characterized in that the ERS-10 zeolite is in an amount ranging from 20 to 80% by weight.
12. 12. The process according to claim 1, characterized in that the aromatic hydrocarbon is selected from benzene, toluene, xylene or mixtures thereof.
13. 13. The process according to claim 12, characterized in that the aromatic hydrocarbon is benzene.
14. 14. The process according to claim 1, characterized in that the olefin is selected from ethylene and propylene.
15. 15. The process according to claim 1, characterized in that the olefin is added in at least two stages.
16. 16. The process according to claim 1, characterized in that two or more catalytic beds or reactors are used in series.
17. 17. A process for the transalkylation of aromatic hydrocarbons, characterized in that it comprises placing an aromatic hydrocarbon in contact with a polyalkylated aromatic hydrocarbon in the presence of a catalyst containing zeolite ERS-10.
18. 18. The process according to claim 17, characterized in that it is carried out at a temperature ranging from 100 to 350 ° C, at a pressure ranging from 10 to 50 atm, and at a space velocity WHSV ranging from 0.1 to 200. hours "1, and with a molar ratio between aromatic hydrocarbon and polyalkylated aromatic hydrocarbon ranging from 1 to 30.
19. 19. The process according to claim 18, characterized in that the temperature is between 150 and 300 ° C, the pressure is between 20 and 45 atm, the space velocity WHSV is between 1 and 10 hours "1, and the molar ratio between hydrocarbon aromatic and polyalkylated aromatic hydrocarbon is between 1 and 10.
20. 20. The process in accordance with the claims 17 to 19, characterized in that it comprises placing an aromatic hydrocarbon in contact with a polyalkylated aromatic hydrocarbon under at least partially liquid phase conditions.
21. 21. The process according to claim 17, characterized in that the aromatic hydrocarbon is selected from benzene, toluene, xylene or mixtures thereof.
22. 22. The process according to claim 21, characterized in that the aromatic hydrocarbon in benzene.
23. 23. The process according to claim 17, characterized in that the polyalkylated aromatic hydrocarbon is selected from diethylbecene and diisopropylbenzene.
24. 24. The process according to claim 17, characterized in that the ERS-10 zeolite is based on aluminum and silicon oxides.
25. 25. The process according to claim 17, characterized in that the ERS-10 zeolite is combined with an inorganic oxide as a ligand.
26. 26. The process according to claim 25, characterized in that the ERS-10 zeolite is in an amount ranging from 20 to 80% by weight.
27. 27. The process according to claim 17, characterized in that the cationic sites in the zeolite ERS-10 are occupied predominantly by hydrogen ions.
28. 28. The process according to claim 27, characterized in that at least 80% of the cationic sites are occupied by hydrogen ions.
29. 29. A process for the preparation of monoalkylated aromatic hydrocarbons, characterized in that it comprises: i) placing an aromatic hydrocarbon in contact with a C2-C4 olefin, under catalytic conditions, in the presence of a catalyst comprising zeolite ERS-10, ii) separating the product obtained in: (a) a fraction containing an aromatic hydrocarbon, (b) a fraction containing a monoalkylated aromatic hydrocarbon, and (c) a fraction containing polyalkylated aromatic hydrocarbons, iii) placing the fraction containing polyalkylated aromatic hydrocarbons in contact with an aromatic hydrocarbon, under transalkylation conditions, in the presence of a catalyst comprising zeolite ERS-10.
30. 30. The process according to claim 29, characterized in that step (i) is carried out at a temperature ranging from 100 to 300 ° C, at a pressure ranging from 10 to 50 atm and at a space velocity WHSV that varies from 0.1 to 200 hours "1 and a molar ratio of [aromatic substances] / [olefin] ranging from 1 to 20, and step (iii) is carried out at a temperature ranging from 100 to 350 ° C, a pressure that varies from 10 to 50 atm, and a space velocity WHSV that varies from 0.1 to 200 hours "1, and with a molar ratio between aromatic hydrocarbon and polyalkylated aromatic hydrocarbon ranging from 1 to 30.
31. 31. The process according to claim 30, characterized in that in step (i) the temperature is between 120 and 230 ° C, the pressure is between 20 and 45 atm, the space velocity WHSV is between 1 and 10 hours "1 and the molar ratio between aromatic substance and olefin is between 2 and 8, and in stage (iii) the temperature is between 150 and 300 ° C, the pressure is between 20 and 45 atm, the space velocity WHSV is between 1 and 10 hours "1 and the molar ratio between aromatic hydrocarbon and polyalkylated aromatic hydrocarbon is between 1 and 10.
32. 32. The process according to claims 29 to 31, characterized in that it comprises placing the aromatic hydrocarbon in contact with the olefin under at least partially liquid phase conditions.
33. 33. The process according to claim 29, characterized in that at least 80% of the cationic sites of the zeolite ERS-10 are occupied by hydrogen ions.
34. 34. The process according to claim 29, characterized in that the ERS-10 zeolite is based on aluminum and silicon oxides.
35. 35. The process according to claim 29, characterized in that the aromatic hydrocarbon is benzene. 37. The process according to claim 29, characterized in that the olefin is selected from ethylene and propylene. 38. The process according to claim 29, characterized in that the polyalkylated aromatic hydrocarbon is diethylbenzene or diisopripylbenzene.