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UNITED STATES PATENT of FICE ANSOLE MANUEFACTURE Walter D

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UNITED STATES PATENT of FICE ANSOLE MANUEFACTURE Walter D Patented Dec. 13, 1949 2,490,842 UNITED STATES PATENT of FICE ANSOLE MANUEFACTURE Walter D. Smutz, Bedford, Ohio, assignor to E. I. du Pont de Nemours & Company, Wilmington, Del., a corporation of Delaware No Drawing. Application January 27, 1947, Serial No. 724,718 8 Claims. (C. 260-612) 2 This invention relates to etherification proc contain a plurality of rings, as in the case of esses and more particularly to processes for pro naphthol. There may be a plurality of hydroxy ducing methyl ethers of aromatic hydroxy com groups on the aromatic nucleus, as in the case pounds, especially anisole, in which a methyl of resorcinol. There may be substituent groups sulfate is added to a hot aqueous solution of a . On the ring, as in the case of vanillin. salt selected from the group consisting of alkali The methyl sulfate used according to a proc metal and ammonium salts of aromatic ring ess of this invention may be a sulfate having a substituted hydroxy compounds, the rate of ad methyl group directly attached to the sulfate dition being such that the methyl sulfate does radical. The methyl sulfate may also contain a not exceed its solubility in the solution, whereby 0. metal substituent on the sulfate radical, as in reaction occurs and a methyl ether of the aro the case of sodium methyl sulfate or potassium matic ring-substituted hydroxy compound is methyl sulfate, it may contain an ammonium formed, and the methyl ether is removed from substituent as in the case of ammonium methyl the reaction mixture as fast as it is formed. sulfate, or it may contain a hydrogen substituent Processes for etherifying aromatic hydroxy 15 as in the case of methyl acid sulfate. When compounds heretofore available have Suffered dimethylsulfate is the methyl sulfate used par from the disadvantage that poor yields were ob ticular advantages are achieved, because prob tained based on the amount of etherifying agent lens arising from the sparing solubility of the used. Yields as high as 75% have been consid dimethyl sulfate are overcome according to a ered to be about all that could be expected. Di 20 method of this invention. methylsulfate is often used as an etherifying The methyl Sulfate is added to an aqueous so agent and the poor yields obtained have been lution of a salt selected from the group consist explained on the premise that the first methyl ing of alkali metal and ammonium salts of the group is readily available for reaction and is aromatic ring-substituted hydroxy compound. readily converted but the second group is tena 2 5. Thus, the Solution may, for instance, contain ciously held and that even prolonged exposure Sodium, potassium, lithium, or ammonium of an etherifiable material to the action of di phenate, in which cases the ether formed will methylsulfate would not suffice to increase the be the methyl ether of phenol, anisole. The yield above the 75% maximum. aqueous Solution should remain hot, it being pre Now according to the present invention it has 30 ferred to conduct the reaction at upwards of 80° been found that yields up to almost 100% of C. It is particularly preferred to maintain the theoretical may be achieved in proceSSes for temperature at or above that at which the prod producing methyl ethers of aromatic hydroxy uct formed is steam-distilled off as fast as it is compounds by adding a methyl sulfate to a hot formed. In the case of anisole, for instance, this aqueous solution of a salt selected from the group temperature is about 106° C. consisting of alkali metal and ammonium salts It is desirable that the aqueous solution con of aromatic ring-substituted hydroxy compounds, tain a Substantial concentration of the salt of the rate of addition being such that the methyl the aromatic hydroxy compound. Particularly sulfate does not exceed its solubility in the Solu beneficial results are obtained when the concen tion, whereby reaction occurs and a methyl ether 40 tration is above about 12% by Weight of the salt of the aromatic ring-substituted hydroxy com and in the case of the manufacture of anisole pound is formed, and removing the methyl ether it is especially preferred that the solution con from the reaction mixture as fast as it is formed. tain about 23% of sodium phenate by weight. The invention will be particularly described The rate of addition of the methyl sulfate with relation to processes for producing anisole, 45 should be such that it does not exceed its solu C6H5OCH3 using dimethylsulfate as the methylat bility in the solution. When a metal methyl ing agent but it will be understood that the proc Sulfate or ammonium methyl sulfate is used the esses are applicable to the production of methyl solubility is relatively high and the rate of ad ethers of other aromatic hydroxy compounds and dition may be relatively rapid at least until the that methyl acid Sulfate may be used as the 50 Solution becomes partially saturated with the methylating agent, metal Sulfate formed by the reaction. A com By the term “aromatic hydroxy compound' is mon ion effect then occurs and the rate of addi meant any compound in Which there is a hy tion may need to be reduced. When methyl acid droxy group attached directly to an aromatic sulfate is used it may be desirable to have pres ring, such as phenol. The aromatic nucleus may 55 ent in the reaction mixture an amount of a basic 2,490,842 3 4 material sufficient to react with the acid sulfate ing-out procedure is nevertheless ordinarily eco radical. On the other hand, when dimethylsul nomically justified. fate is used the rate of addition will need to be In practice all of the foregoing operation steps relatively slow because dimethyl sulfate is only may advantageously be carried out continuously. Sparingly soluble in the reaction medium. In the case of anisole, for instance, the Sodium It is particularly preferred that the reaction phenate may be continuously formed in the re mixture be violently agitated during the addi action mixture by adding phenol and sodium hy tion of the dimethylsulfate and that the dimeth droxide in stoichiometric proportions. A slight yisulfate be added to the bottom of a volume of excess of Sodium hydroxide may be used here in the aqueous Sodium phenate solution. The di O the event that the dimethylsulfate to be used methylsulfate may be run in, for instance, through should contain free sulfuric acid. Steam distill an addition tube extending to the bottom of the lation of anisole, the separation of anisole and reaction tank and an agitator may be so disposed water from the distiliate, the removal of sodium as to create an intense Zone of agitation at the sulfate, and the Saturation of the distillate with end of this addition tube. It will be understood s the Sodium sulfate may all be carried out con that even though the Solution is not saturated tinuously with the operational advantages which with respect to dimethylsulfate the undesirable Such operation entails. condition of having undissolved dimethylsulfate The nature of this invention will be better may nevertheless result unless care is taken to understood by reference to the following illustra disperse the dimethylsulfate as it enters the re 20 tive examples. action mixture. Under the conditions above described a reac Eacample 1 tion occurs and a methyl ether of the aromatic To a reaction vessel there was added 67.2 parts ring-Substituted hydroxy compound is formed. by weight of water and 23 parts by weight of The reaction of dimethylsulfate and Sodium 25 phenol and the mixture was heated with agita phenate, for instance, proceeds according to the tion to 50° C., whereupon the phenol melted and following equation: Went into Solution. There was then added 9.8 parts by weight of sodium hydroxide pellets and 30 the mixture was stirred until the sodium hy It will be noted that this equation calls for the droxide dissolved, whereby reaction occurred and use of both of the methyl groups on the dimethyl sodium phenate was formed. This gave 100 parts Sulfate and the processes of the present invention by weight of a 28.4% sodium phenate solution. accomplish substantially this result. Heretofore This Solution was heated to 112° C., which was it has been regarded as impossible to recover more 35 approximately its boiling point. To the solution than about half of the second methyl group in there was then added, simultaneously, dimethyl the product. Sulfate and a Sodium phenate solution containing As fast as the methyl ether of the aromatic 21% by weight of Sodium phenate and .05% of ring-substituted hydroxy compound is formed it Sodium hydroxide. The purpose of the sodium should be removed from the reaction mixture. 40 hydroxide was to neutralize an equivalent free Where the conditions are right, as in the case of acidity in the dimethylsulfate. The dimethylsul anisole, this may ideally be accomplished by Steam fate was added through an addition tube extend distillation, that is, by carrying out the reaction ing to the bottom of the reaction vessel and the at a temperature Sufficiently high to effectuate reaction mixture was violently agitated, with the steam distillation of the product. The distillate 45 Zone of maximum agitation being at the point may then be condensed, separated as by gravita of delivery of the dimethylsulfate. The dimethyl tion into an anisole layer and an aqueous layer, Sulfate and additional sodium phenate solution and the aqueous layer returned to the reaction Were charged in gradually over a period of two mixture.
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