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United States Patent Office Patented July 17, 1962 1 3,045,050 United States Patent Office Patented July 17, 1962 1. 2 3,045,050 is reacted in the presence of a condensation agent, for METHOD OF PRODUCING AROMATIC example aluminum chloride. However, this method is SULPONES not very suitable for the production of ketones or com Cornelis Johannes' Schoot, Klaas Hinderikus Klaassens, and Johannes Jacobus Ponjee, Eindhoven, Netherlands, pounds which contain an aliphatic or cyclic ether or thio assignors to North American Philips Company, Inc., ether group. In these compounds, generally the ether New York, N.Y., a corporation of Delaware or thio-ether bond will be split as a secondary reaction No Drawing. Fied July 30, 1958, Ser. No. 751,885 by the action of the condensation agent, in the method in Claims priority, application Netherlands Aug. 14, 1957 accordance with the invention this disadvantage does not 10 Claims. (Cl. 260-607) occur, ether and thio-ether bonds are substantially not 10 attacked. This invention relates to a method of producing aro Suitable metal salts of sulfuric acid are the salts of the matic sulphones, characterized in that an aromatic com metals of the subgroups of the periods IV, V and VI and pound RH or RH or a mixture of these compounds, of the group VIII of the periodic table of the elements where R and R' can be equal or different and both rep and the salts of manganese, and particularly the salts of resent a benzene, naphthalene or thiophen nucleus which 15 the group comprising silver, zinc, cadmium, copper, carries at least one hydrocarbon radical or at least one mercury, tin and lead. The reaction proceeds smoothly ether or thioether group, or a non-substituted thiophen and completely with the use of salts of the metals silver, nucleus, is heated in the presence of a halide of ortho-, Zinc or cadmium and especially the salts of silver. meta- or pyrophosphoric acid or a mixture of these acids As is well known, there are several halides of the and a metal salt of sulphuric acid, with the exception of 20 above-mentioned phosphoric acids. This is due on the the salts of the alkaline earth and alkaline metals. one hand to the fact that one or more hydroxyl groups In the sulphones produced by this method sulphur is can be replaced by halogen atoms while on the other directly bound to the aromatic nuclei. hand in producing a halide of one of the said phosphoric This is illustrated by the following equation, which can acids generally a mixture is obtained the exact composi represent the reaction when the aromatic compound RH 25 tion of which cannot readily be ascertained. It has been is heated in the presence of silver sulphate and phos found that these mixtures can be used to advantage. phorus oxychloride: However, in practice those halides are preferred in which all the hydroxyl groups are replaced by halogen atoms. A suitable halide is the acid chloride, more particularly Suitable aromatic compounds are compounds according 30 phosphorus oxychloride. to the formula RH, where R represents a benzene, naph In the method according to Friedel-Crafts the initial thalene, or thiophen nucleus carrying at least one, more materials are sulphohalides. These compounds must be particularly 1 to 3 hydrocarbon radicals, which can be previously produced separately. In contradistinction an alkyl, aralkyl or aryl group, for example a methyl, thereto, in the method in accordance with the invention benzyl or phenyl group. Especially good results are ob 35 the initial materials are aromatic compounds which do tained with benzene derivatives. It was found that suit not contain the sulphohalide group. This is a special able substituents are alkyl groups having 1 to 18 carbon advantage of the present method which thus has an at atoms each, for example a hexyl, octyl or decyl group, tractive simplicity. A further advantage consists in that more particularly groups having 1 to 5 carbon atoms this method is particularly suited for the production of each, such as, for example, an ethyl, propyl, isopropyl, 40 Symmetric sulphones. For this purpose one aromatic butyl or tertiary butyl group, and preferably a methyl compound is chosen as the initial material. However, group. Further suitable materials are benzene and naph the present method also enables mixed sulphones to be thalene derivatives having at least one, more particularly produced. For this purpose the initial material must 1 to 3 and preferably one ether or thio-ether group, which be a mixture of two different aromatic compounds RH may be either an alkoxy, aralkoxy or aryloxy group or and R'H. the corresponding thio-ether group, as substituents in In the present method a heterogeneous reaction is the nucleus. Especially good results are obtained with involved since the metal salt is present in the solid state. benzene derivatives containing an alkoxy group having A rapid and complete conversion requires the use of the from 1 to 5 carbon atoms, for example an ethoxy, pro metal salt as a fine powder. poxy or butoxy group, and preferably a methoxy group, The reaction should be performed under substantially in the nucleus. Monomethoxy benzene is particularly anhydrous conditions. This implies that the reactants suitable. must be entirely or substantially anhydrous so that from Furthermore the method in accordance with the in metal salts which contain water of crystallization, this vention is of particular importance for the production water must previously be removed entirely or substan of sulphones of compounds according to the formula RH, tially entirely. This can be effected by heating, prefer where R represents a thiophen nucleus which may be ably at a reduced pressure. Since the crystallized silver substituted, provided that neither the nucleus nor the sub Sulphates contain no water of crystallization, these salts stituents contain free hydroxyl, Sulphydryl or amino are to be preferred for this reason also. groups. Suitable substituents in the thiophen nucleus are In addition it was surprising to find that for the reac particularly alkyl groups, more particularly groups hav 60 tion to proceed smoothly and completely the reaction ing 1 to 18 carbon atoms each, for example, a hexyl, mixture must contain a slight amount of water. As long octyl or decyl group, and preferably groups having 1 as the reaction mixture is completely dry, no reaction is to 5 carbon atoms each, for example, an ethyl, propyl, initiated. This may be shown by first working under isopropyl, butyl or tertiary butyl group, and especially completely dry conditions and then adding a few drops a methyl group, and furthermore aliphatic ether or thio 65 of water. Generally it can then be observed that heat ether groups, particularly groups having 1 to 5 carbon generation occurs only after the addition of water owing atoms each and preferably groups having 1 carbon atom to the reaction being initiated. each. Thiocoumarone is also suitable. Alternatively the reaction can be performed in the presence of a diluent which is a solvent for the aro A known method of producing aromatic and mixed 70 matic compound RH. As inert diluents use can be made aliphatic-aromatic sulphones is that according to Friedel of aliphatic hydrocarbons, such as benzene, aromatic hy Crafts, in which an aromatic or aliphatic sulphohalide drocarbons, such as chlorobenzene and nitrobenzene, ali 3,045,050 3 4 phatic ethers, for example dibutyl ether, and aliphatic Example III-4,4'-Dimethoxy-Diphenylsulphone esters, such as butyl acetate. It has also been found that the use of a nitro-alkane as the diluent increases the -- 3Hg2SO4 – 2PO Cls --> yield. Hence very suitable diluents are nitromethane and nitropropane. 5 3CH3O- S ork >-0 CH3 - 3IgCl2 - 2IPO Alternatively, an excess of the aromatic compound RH can be used as a diluent. In a flask of capacity 200 ccs., which was provided In the present method monosulphones are produced with a reflux cooler and a tube containing calcium chlo Substantially only. Disulphones are not or substantially ride, a mixture of 49.7 gms. (0.1 mole) of Substantially not produced. It has been found that this production of 0 anhydrous mercuro-sulphate, 10.2 gms. (0.067 mole) of monosulphones does not depend upon the proportions of phosphorous oxy-chloride and 42 gms. of methoxyben the amounts of the reactants. Even if too slight an zene were heated on a water bath for 2 hours. Subse amount of the aromatic compound RH is used, mono quently the mixture was heated to 150 C. on an oil Sulphones are produced substantially only. bath for 2 hours. Then the reaction mixture was Sub The reaction is preferably performed at an elevated jected to a distillation with the aid of steam in order to temperature of between 80° C. and 180° C., preferably remove the excess methoxybenzene. The distillation res between 100° C. and 150° C. idue was filtered off and the separated mercury Salts The sulphones to be produced by the method accord were extracted with hot benzene. The filtrate and the ex ing to the invention can be used for a variety of pur tract were dried together over calcium chloride and then poses. Certain sulphones may, for example, be used as 20 filtered, the benzene being distilled off subsequently. initial materials for syntheses, as solvents or diluents, as Yield of 4,4'-dimethoxy-diphenylsulphone: 11.1 gms.- softeners, in dielectrics and insulating material, as tanning 40%. materials, as antibiotics, as basic materials for the produc After crystallization from ethanol, the melting point was tion of dyestuffs, as bactericides and as therapeutic agents. 126 C. The invention will now be illustrated by the following Mixed melting point: 126° C.
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