Chemistry of hydrocarbon compounds – Aromatic compound synthesis – By condensation of entire molecules or entire hydrocarbyl...
Patent
1999-01-14
2000-05-09
Griffin, Walter D.
Chemistry of hydrocarbon compounds
Aromatic compound synthesis
By condensation of entire molecules or entire hydrocarbyl...
585446, C07C 268, C07C 264
Patent
active
060606320
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a process for producing ethylbenzene useful as, for example, a starting material for various polymers.
BACKGROUND ART
WO96/20148 discloses a production process of ethylbenzene from benzene and ethylene using a zeolite such as MCM-22, MCM-49 or MCM-56 as a highly selective catalyst. According to this reference, the alkylation is carried out in a liquid phase and the benzene/ethylenemolar ratio is 5 to 10 in most cases and is 5.5 in the Examples.
U.S. Pat. No. 5,334,795 also discloses a synthetic process of ethylbenzene from benzene and ethylene using MCM-22 zeolite. However, in the Examples of this reference, the benzene/ethylene molar ratio is at least 4.6.
JP-B-06043346 discloses a process comprising bringing an organic aromatic compound into contact with a C2.about.C20 olefin to form alkylation products in a distillation column reactor containing a structure obtained by immobilizing a fixed-bed acidic catalyst in a packing for distillation, separating the formed alkylation products and unreacted organic aromatic compound and olefin, and taking out the alkylation products from the distillation reactor at a place under the fixed bed. This reference, however, does not disclose employment of a .beta. zeolite. Moreover, in the Examples of the reference, the benzene/ethylene molar ratio of the reaction products recovered from the bottom is at least 3.47 and the production rate of ethylbenzene relative to the weight of the catalyst is as very low as 0.12 to 0.3.
U.S. Pat. No. 5,118,896 discloses a process in which continuous liquid-phase alkylation of a liquid aromatic compound selected from benzene, toluene and xylene using an olefin as an alkylating agent is carried out in the fixed bed of a reactive-distillation type reactor by using a catalyst comprising a crystalline aluminosilicatezeolite, silica and alumina and having a pore volume of 0.25 to 0.35 ml/g, a pore radius of more than 450 .ANG. and aparticle diameter of not more than 1/64 inch. This reference describes an example using a reactive distillation method in which the molar ratio of the aromatic compound to ethylene is 2. In this example, the conversion of ethylene is as very low as 55%.
JP-A-04187647 discloses a process in which alkylation and transalkylation are carried out together on a molecular sieve catalyst for aromatic alkylation and transalkylation in a liquid phase, and the benzene/ethylene molar ratio is 4 or less and may be about 2. In this reference, a .beta. zeolite is mentioned as the catalyst for alkylation and the benzene/ethylene molar ratio is 5.2 in the Examples. The reference discloses a method for attaining a benzene/ethylene molar ratio of 2 under idealized reaction conditions. However, in this method, the above molar ratio value is attained by feeding ethylene in five stages.
WO96-04225 discloses fixed-bed liquid-phase alkylation by gas-liquid descent parallel-flow method carried out in a trickle bed region by the use of a .beta. zeolite as a catalyst. However, this process has a high productivity but is disadvantageous in that the catalytic activity is greatly changed in the initial stage of the reaction and is difficult to control.
JP-A-03181424 discloses liquid-phase alkylation and transalkylation which use a .beta. zeolite as a catalyst, and the molar ratio of an aromatic hydrocarbon to an olefin is 4 or more in the Examples of this reference.
Zeolite catalysts are used as catalysts for alkylation of aromatic hydrocarbons and can be advantageously used as non-corrosive catalysts in place of the conventional catalysts for Friedel-Crafts reaction. Therefore, various proposals have been put forward for the zeolite catalysts.
However, in most conventional processes, alkylation is carried out at a relatively high benzene/ethylene molar ratio. Since such a high molar ratio increases the amount of unreacted benzene to be recycled and hence the trouble of benzene recovery, it is very disadvantageous from an industrial viewpoint. The reasons why alkylation is carried out at a h
REFERENCES:
patent: 5086193 (1992-02-01), Sy
patent: 5113031 (1992-05-01), Sy
patent: 5118896 (1992-06-01), Steigelmann et al.
patent: 5334795 (1994-08-01), Chu et al.
Ishida Hiroshi
Itani Yoshihito
Takamatsu Yoshikazu
Asahi Kasei Kogyo Kabushiki Kaisha
Dang Thuan D.
Griffin Walter D.
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