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Process for Producing Acetyl-Substituted Aromatic turopaisches Patentamt European Patent Office © Publication number: 0 21 5 351 Office europeen des brevets A2 <2> EUROPEAN PATENT APPLICATION © Application number: 86111905.5 © int. CI.4: C07C 45/46 C07C , 49/76 , C07C 49/788 C07C 49/825 ®r\ Daten of 28'08-86„ , , f,l,n9: C07C 49/83 , C07C 49/84 © Priority: 31.08.85 JP 191521/85 © Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC. © Date of publication of application: 5-2, Marunouchi 2-chome Chiyoda-Ku 25.03.87 Bulletin 87/13 Tokyo(JP) © Designated Contracting States: @ Inventor: Fujiyama, Susumu DE FR GB IT NL 522-65, Kamitomii Kurashiki-shi(JP) Inventor: Matsumoto, Shunichi 1168-3, Tanoue Kurashiki-shi(JP) Inventor: Yanagawa, Tatsuhiko 1987, Nakashima Kurashiki-shi(JP) © Representative: Patentanwalte Griinecker, Kinkeldey, Stockmair & Partner Maximilianstrasse 58 D-8000 Munchen 22{DE) Process for producing acetyi-substituted aromatic compound. v=y This invention provides a process for producing an acetyi-substituted aromatic compound by making an aromatic compound react with acetyl fluoride in the presence of substantially anhydrous hydrogen fluoride as a catalyst. M It has been already known to acylate- an ar- ^omatic compound with an acid fluoride in the pres- ence of boron fluoride or hydrogen fluoride and O boron fluoride as a catalyst. It has been found that, *^in a reaction of an aromatic compound with acetyl fjfluoride, even when hydrogen fluoride alone is used ■as a catalyst, the intended acetyi-substituted ar- ^omatic compound can be obtained in excellent yield 5 and further the complex compound formed can be ^decomposed without difficulty and the hydrogen flu- yoride catalyst can be easily recovered. srox ixjpy uentre 1 0 215 351 2 PROCESS FOR PRODUCING ACETYL-SU BSTITUTED AROMATIC COMPOUND The aromatic compounds used as the starting BACKGROUND OF THE INVENTION material in this invention include alkylbenzenes such as toluene, xylene, trimethylbenzene, ethyl- This invention relates to a process for produc- benzene, cumene, and butylbenzene; naphthalene ing an acetyi-substituted aromatic compound which 5 and alkylanphthalenes such as methylnaphthalene; comprises acetylating an aromatic compound such phenols and naphthols; and further aromatic ethers as an aromatic hydrocarbon and a phenol with such as anisole and phenyl ether. Particularly pre- acetyl fluoride. ferred are compounds in which the para position to It is disclosed in Japanese Patent Application the substituent in the aromatic ring is vacant and Kokai (Laid-open) No. 135756/79 to produce a 2- io naphthalenes having a substituent in the 2-position. alkyl-6-acylnaphthalene by acylating a 2-alkylnaph- Acetyl fluoride as the other starting material, thalene with an acid fluoride in the presence of can be obtained by mixing acetic anhydride or boron fluoride or hydrogen fluoride and boron flu- acetyl chloride with hydrogen fluoride to produce oride as a catalyst. acetyl fluoride according to the following equation - It is described in the above-mentioned inven- 75 (I) or (2) and separating the free acid simulta- tion that the presence of boron fluoride as a cata- neously formed. lyst component is essential .and the absence of boron fluoride results in low yield of the acylation (CH3CO),0 + HF - CH3COF + CH3COOH - product. However, according to the experiment of (I) the present inventors, it has been found that when 20 boron fluoride is used as a catalyst component in CH3COCI + HF - CH3COF + HCI (2) the reaction of aromatic compound with acetyl flu- It is essential here that the reaction (2) men- oride, it is difficult to decompose the resulting tioned above should be carried out at a slight complex compound on account of the instability of excess of acetic anhydride. Thus, when hydrogen aromatic keton of the reaction product. 25 fluoride is in excess of the equivalent, the maxi- mum azeotropic mixture combined hydrogen flu- oride with the r acid, which leads to the loss of SUMMARY OF THE INVENTION hydrogen fluoride, is formed to become insepa- rable and further the acid formed is contaminated Accordingly, the present inventors have made 30 with fluorine, so that special treatments are re- extensive studies to attain a process for producing quired to remove it. When acetic anhydride is in an acetyi-substituted aromatic compound with high- excess, such difficulties do not occur and hydrogen er efficiency including the steps of the decomposi- fluoride can be quantitatively recovered as acetyl tion of the complex compound and the recovery of fluoride. However, there is no need of large excess the catalyst component. Consequently, it has been 35 and the ratio of excess acetic anhydride to hy- found that, in the reaction of an aromatic com- drogen fluoride may be 5 mol% or below. pound with acetyl fluoride, even when hydrogen The apparatus used for generating acetyl flu- fluoride alone is used as a catalyst the intended oride may be a conventional distillation column acetyi-substituted aromatic compound can be ob- having a number of plates necessary for fractionat- tained in excellent yield and further the complex 40 ing acetyl fluoride and the free acid. Acetic anhy- compound formed can be readily decomposed and dride and hydrogen fluoride are fed to the appro- the hydrogen fluoride catalyst can be easily recov- priate plate of the distillation column as a mixture ered. This invention has been accomplished on the or separately, the column bottom is heated up to basis of above findings. the boiling point of the acid and the column top is 45 given an appropriate reflux. Such a conventional distillation operation makes it possible to recover DETAILED DESCRIPTION OF THE INVENTION pure acetyl fluoride from the column top and an acid containing no fluorine from the column bottom. Thus, this invention provides a process for Since the reaction proceeds at a high rate, producing an acetyi-substituted aromatic com- 50 virtually no residence time is necessary. The reac- pound which comprises making an aromatic com- tion can be conducted under an ordinary or an pound including an 2-alkylnaphthalene react with applied pressure, for example I kg/cm2G, and either acetyl fluoride in the presence of substantially an- hydrous hydrogen fluoride as a catalyst. 2 o 0 215 351 4 now operauon or Datcnwise operation may De used. The reaction proceeds in a homogeneous liq- The difference of boiling point between acetyl flu- uid phase or, according to circumstances, in two- oride and the acid formed is so large that the two liquid phases consisting of a starting aromatic com- can be easily separated. pound phase and a catalyst phase, so that there is The acetyl fluoride thus formed is used for 5 no need of vigorous stirring. Since the reaction is acetylation as the acetylating agent. The molar slightly exothermic, a reactor provided with heat ratio of acetyl fluoride to the starting aromatic com- removal equipment is used as required. pound is I or below, 0.9 to 0.5 being particularly The acetylation reaction liquid thus obtained is preferable. The presence of excess acetyl fluoride a solution of an aromatic ketone, the acetylation decreases the overall reaction rate (i.e. the space w product, in hydrogen fluoride. On heating the -reac- time yield of the acetylation product). tion liquid, the affinity between the reaction product As the catalyst, a substantially anhydrous hy- and hydrogen fluoride is broken and hydrogen flu- drogen fluoride is used. Its water content is prefer- oride can be easily vaporized and separated. ably 5% or below because the presence of water in It is necessary to conduct the above-mentioned hydrogen fluoride causes the rapid decrease of rs catalyst recovery operation as rapidly as possible catalytic activity. In order to obtain a sufficient in order to avoid the thermal degradation of the reaction rate, the molar ratio of hydrogen fluoride to reaction product. For this purpose, the catalyst be used relative to the acetylating agent is 5 or recovery operation is preferably conducted in a above, preferably in the range of 10 to 20. Hy- flow operation using a multistage gas-liquid contact drogen fluoride used in a molar ratio of 20 or above 20 apparatus (i.e. a distillation column). For catalyst gives little additional effect and hence is not ad- recovery, heating at a temperature of 40°C or from vantageous the economical viewpoint of the higher, particularly 40 to 100 °C, is necessary. The process. decomposition column is preferably fed with an The reaction temperature of acetylation is 0 to amount of heat which is in excess of that neces- 70°C, preferably 10 to 50°C. Since the reaction rate ?5 sary for vaporizing hydrogen fiuoride fed to the increases as the temperature is increased but also column. It is advantageous in the process to con- the side reaction increases, an optimum tempera- duct the catalyst recovery operation under atmo- ture is selected from the above-mentioned range spheric pressure or a slightly increased pressure of depending upon the starting material used. When 2 kg/cm2G or below. In order to make the thermal the starting compound has a high melting point and ?o decomposition of the complex compound between further is insoluble in hydrogen fluoride as in the the acetyi-substituted aromatic compound and hy- :ase of aromatic hydrocarbons, it is effective to drogen fluoride proceed smoothly, the decomposi- jse a suitable solvent in order to make the reaction tion is preferably conducted by heating the com- Droceed smoothly. Preferable solvents are those plex compound under reflux using as a diluent a which can dissolve the starting compound well, are is substance which has a boiling point such that it is :hemically inert under reaction conditions, and easily separable from hydrogen fluoride, has a lave a good compatibility also with the reaction good compatibility with the reaction product, name- iquid formed.
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