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United States Patent (19) 11) Patent Number: 5,015,786 Araki Et Al

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United States Patent (19) 11) Patent Number: 5,015,786 Araki Et Al United States Patent (19) 11) Patent Number: 5,015,786 Araki et al. 45 Date of Patent: May 14, 1991 54 PREPARATION OF CUMENE THROUGH 4,267,380 5/1981 Austin et al. ........................ 568/385 ALKYLATION OF ANAROMATIC 4,268,454 5/1981 Pez et al. ............................. 568/880 4,567,304 l/1986 Fulmer ................................ 568/385 COMPOUND AND PREPARATION OF 4,783,559 11/1988 Matsushita et al.................. 568/862 PHENOL THROUGH CUMENE 4,877,909 10/1989 Mizusaki et al. .................... 568/880 75) Inventors: Shintaro Araki, Ichihara; Fujihisa Matsunaga, Wakayama; Hiroshi FOREIGN PATENT DOCUMENTS Fukuhara, Ichihara, all of Japan O164568 12/1985 European Pat. Off. ............ 568/385 0025653 5/1974 Japan ................................... 568/385 73) Assignee: Mitsui Petrochemical Industries Inc., 0073796 6/1980 Japan ................................... 568/385 Tokyo, Japan Primary Examiner-Werren B. Lone 21 Appl. No.: 441,477 Attorney, Agent, or Firm-Nixon & Vanderhye 22 Filed: Nov. 27, 1989 57 ABSTRACT (30) Foreign Application Priority Data In a first form, a process is provided for preparing phe nol by converting acetone by-produced by the cumene Nov. 28, 1988 (JP) Japan ................................ 63-300300 process into isopropanol, and alkylating benzene with Nov. 30, 1988 JP Japan ...... ... 63-302617 the isopropanol and optional propylene, thereby form Dec. 12, 1988 (JP) Japan ................................ 63-328722 ing phenol without acetone by-product. And cumene is 51) Int. Cl. ....................... C07C37/07; CO7C39/04 prepared by alkylating benzene in the presence of a 52 U.S. C. .................................... 568/798; 568/362; zeolite catalyst using isopropanol or a mixture of isopro 568/385; 568/754; 568/768; 568/862; 585/446 panol and propylene as an alkylating agent. Further 58) Field of Search ................ 585/446; 568/569, 573, provided is the continuous alkylation of benzene with 568/798, 754, 768,846, 862, 880; 586/385, 362, isopropanol wherein a reaction mixture is divided into 754, 768, 798 first and second portions, with the first portion being References Cited recycled to the reactor and the second portion being (56) taken out as a reaction product. U.S. PATENT DOCUMENTS 4,238,417 12/1980 Austin et al. ........................ 568/385 7 Claims, 1 Drawing Sheet (A+B) U.S. Patent May 14, 1991 5,015,786 F G. 1 5,015,786 1. 2 known as disclosed in Japanese Patent Application PREPARATION OF CUMENE THROUGH Kokai Nos. 159427/1983 and 159430/1983. Reaction ALKYLATION OF AN AROMATIC COMPOUND under liquid phase conditions is also proposed as dis AND PREPARATION OF PHENOL THROUGH closed in U.S. Pat. No. 4,011,278. CUMENE As to the reuse of the acetone which is by-produced in the cumene process, for example, by its conversion This invention relates to the preparation of cumene into isopropanol, no useful proposals have been made. by alkylating an aromatic compound, the preparation of The phenol preparing process generally known as the phenol via cumene, and the alkylation of an aromatic cumene process is characterized by the production of compound using an alcohol as the alkylating agent. O acetone by-product, which is advantageous from some aspects, but disadvantageous from other aspects. More BACKGROUND OF THE INVENTION particularly, it is an advantage in that simultaneous Alkylated aromatic compounds obtained by alkylat production of two products in a single preparation unit ing aromatic compounds are commercially important is more efficient than individual production in separate intermediate stock materials. For example, cumene ob 15 units. In turn, if the proportion of phenol and acetone tained by reacting benzene with propylene is a very produced is unbalanced relative to their commercial important compound as a reactant for the synthesis of demands, one for less demand is produced largely in phenol. vain. Cumene is generally produced by alkylating benzene As is known in the art, acetone is available in surplus with propylene. Numerous studies have been made on 20 for these years. Thus the production of acetone by-pro this alkylation process. For example, Japanese Patent duct is now considered as a serious drawback of the Application Kokai No. 40419/1982 discloses alkylation cumene process. Although acetone has found the ma under liquid phase conditions using Lewis acid cata jority of its application as a starting material for prepar lysts. U.S. Pat. No. 2,375,724 discloses the use of solid ing methyl methacrylate, the demand for acetone is phosphoric acid catalysts. 25 decreasing because of a switch of the starting material Cumene is also produced by alkylating benzene with for preparing methyl methacrylate to another. isopropanol. Reaction undergas phase conditions using Under the circumstances, there is a need for the de solid acids is well known as disclosed in Japanese Patent velopment of a phenol preparing process which is de Application Kokai No. 159427/1983 and 159430/1983. void of production of acetone and other by-products. Reaction under liquid phase conditions has also been 30 Although several proposals have been made, there is proposed. For example, U.S. Pat. No. 4,011,278 dis available no process capable of preparing phenol in closes alkylation in the presence of an H-mordenite satisfactory yields. catalyst having a silica-to-alumina ratio adjusted to 40. In addition, impurities in propylene often cause a These processes for the synthesis of cumene have drawback during the preparing step of cumene from several problems. For example, the alkylation using 35 benzene and propylene in the cumene process for the Lewis acids needs the presence of alcohols because the preparation of phenol. That is, propylene for use in the catalysts are readily deactivated by water in the reac cumene preparation is manufactured generally using tion system, and alkylation with alcohols is impossible. crude oil as the starting material. Crude oil, however, The gas phase alkylation with isopropanol is substan contains sulfur compounds and various heavy metals, tially impractical because of low alkylation conversion and these impurities are sometimes carried in propylene and quick deterioration of the catalyst which must be as trace contaminants during its manufacturing process. frequently regenerated to compensate for such a short For example, carbonyl sulfide (COS) as a sulfur com lifetime. The liquid phase alkylation with isopropanol is pound or As as a heavy metal contaminant in propylene high in alkylation conversion, but is doubtful about its inhibits function of a catalyst (aluminum chloride-HCl practical effectiveness because the percent yield of the 45 complex) for use in the cumene preparation, thus dis end product is not demonstrated. This process has left a turbing normal progress of the cumene synthesis. problem to be overcome for commercial production Therefore, a strict purification process is perproduced because expensive catalysts such as ZSM-5 zeolite hav to avoid contamination of propylene with these impuri ing a high silica-to-alumina ratio and dealuminated H ties. Types and quantity of these contaminants, how mordenite are used for water repellency. 50 ever, vary depending on not only the crude oil source It is well known in the prior art to react benzene with but also the difference in the process conditions for the propylene to produce cumene, to oxidize cumene to preparation of propylene from crude oil. Such irregu produce cumene hydroperoxide, and to acid cleave larity burdens the propylene purification process with cumene hydroperoxide into phenol and acetone. A exceptionally complex and severe steps. conventional phenol preparing process having these 55 In consequence, a process for the preparation of steps combined is generally known as the cumene or propylene with highly stable purity containing no such cunol-phenol process. impurities has been expected to be established, for the It is also an old well-known technique to hydrogenate purpose of reducing the extreme burden of steps in the acetone into isopropanol. This technique is still widely propylene purification process. used at present for the assay of the catalytic activity of 60 As to the alkylation of aromatic compounds, a variety a hydrogenating catalyst and other purposes. For exam of processes are known in the art. For example, the ple, the activity of Raney nickel catalysts is often exam alkylating process using olefins has been widely used in ined by comparing their acetone hydrogenating ability. the industry, becoming one of the important industrial Several advanced processes have been proposed as techniques. Various proposals have also been made on disclosed in Japanese Patent Application Kokai Nos. 65 the alkylating process using alcohols. 12729/1987 and 7338/1987. Several prior art techniques for the alkylation of For the alkylation of benzene with isopropanol, reac aromatic compounds using alcohols are described be tion under gas phase conditions using solid acids is well low. (1) Japanese Patent Application Kokai No. 5,015,786 3 4. 159430/1983 discloses a process for preparing a 1,4-dial Moreover, cumene synthesized by using isopropanol kylbenzene compound in the presence of an oxide which has been converted from acetone by means of modified zeolite catalyst. hydrogenation does not contain any of the sulfur com (2) Japanese Patent Application Kokai No. pounds and heavy metals which are contained in the 263934/1986 discloses a process for preparing p-xylene 5 alkylation process of benzene using propylene which is by alkylating toluene with methanol in the presence of manufactured generally using crude oil as the starting a ZSM-5 type zeolite catalyst. material. (3) Japanese Patent Application Kokai No. In one form of the present invention, the object can 216128/1983 and 159427/1983 disclose processes for be attained by properly combining the following steps preparing a monoalkylbenzene or dialkylbenzene by O of: reacting benzene or alkylbenzene with an alcohol in the (a) alkylating benzene with isopropanol and/or prop presence of a proton-exchanged mordenite type zeolite ylene to synthesize cumene, catalyst.
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