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United States Patent Office Patented Mar 3,432,267 United States Patent Office Patented Mar. 11, 1969 2 cordingly, the term "degradation products' as used herein 3,432,267 does not apply to tetrahydro derivatives of the anthraqui REGENERATION OF ANTHRAQUINONE WORK none working compound. NG SOLUTION USED IN THE PRODUCTION OF HYDROGEN PEROXDE In U.S. Patent 2,739,875, issued to Jerome W. Sprauer Nathan Dean Lee, Lambertville, and Nelson Nor on Mar. 27, 1956, there is described a process for treating man Schwartz, Trenton, N.J., assignors to FMC Cor an anthraquinone working solution containing degradation poration, New York, N.Y., a corporation of Delaware products whereby the solution can be regenerated to re No Drawing. Filled May 26, 1967, Ser. No. 641,458 store its hydrogen peroxide synthesizing capacity. In ac U.S. C. 23-207 8 Clains cordance with this process, the anthraquinone working Int, C. C01b. 15/02 solution is heated in the presence of either activated alu O mina or activated magnesia, thereby regenerating its hy drogen peroxide synthesizing capacity. ABSTRACT OF THE DISCLOSURE While this process has been found to be useful and A degraded anthraquinone working solution (made up effective in regenerating some working solutions during of an anthraquinone working compound dissolved in one 5 initial use, after repeated cyclic hydrogenation and oxida or more solvents) used in the production of hydrogen tion of an anthraquinone working solution, it develops a peroxide is regenerated by treating it with ozone, extract resistance to being regenerated by activated alumina or ing the resulting solution with an aqueous caustic solution, magnesia. This resistance is not believed due to loss of separating the aqueous caustic extract from the remaining activity on the part of the activated alumina or activated 20 magnesia, since replacement of these activated materials working solution and contacting said solution with either does not result in any substantial improvement in the de activated alumina or activated magnesia. gree of regeneration. While the reason for this resistance to regeneration is not understood, the result is most serious since expensive anthraquinone working compound must BACKGROUND OF THE INVENTION 25 be replaced in the working solution in order to maintain Field of the invention the hydrogen peroxide output of the working solution at a satisfactory level. The invention relates to the regeneration of anthraqui As a result, there is a need for a method of regenerat nonegen peroxide. working solutions used in the maufacture of hydro ing the Working solutions used in the anthraquinone 30 processes whereby the effective peroxide synthesizing ca Description of the prior art pacity of the solutions can be restored, even after repeated It is known that anthraquinone compounds, e.g., cyclic use of the working solution. 2-ethylanthraquinone, and their tetrahydro derivatives can SUMMARY OF THE INVENTION be used as working compounds in a process for producing hydrogen peroxide. In this process, commonly known as 35 We have now found that a degraded anthraquinone the anthraquinone process, the working compound is dis Working solution made up of an anthraquinone working solved in a suitable solvent, or solvent mixture, and is compound dissolved in at least one solvent, and containing alternately reduced and oxidized. During the reducing degradation products of said working compound produced stage, the working compound is hydrogenated in the pres during the alternate, cyclic hydrogenation and oxidation ence of a catalyst to reduce it to its hydroquinone form. 40 of the Working solution to produce hydrogen peroxide, can In the subsequent oxidation step the working compound be regenerated to increase its hydrogen peroxide produc is oxidized with air, oxygen or other oxygen containing ing capacity by contacting the working solution with an gases to convert it to its quinone form with concomitant effective amount of ozone, extracting the ozone-treated formation of hydrogen peroxide. The hydrogen peroxide Working Solution with an aqueous alkali metal hydroxide product is then removed from the working solution, pref 45 Solution of 5-25% (preferably an aqueous Solution of erably by extraction with water, and the remaining work about 5 to 10% by weight of NaOH), separating the work ing solution is recycled to the hydrogenator to again com ing Solution from the extract, contacting said working mence the cyclic process for producing hydrogen peroxide Solution with either activated alumina or activated mag The detailed operation of this process is described fully nesia, and recovering a regenerated working solution from in U.S. Patents Nos. 2,158,525 and 2,215,883. 50 said activated alumina or activated magnesia. During cyclic hydrogenation and oxidation of the work DESCRIPTION OF THE INVENTION AND THE ing solution in the above process, and particularly during PREFERRED EMBODIMENTS the catalytic hydrogenation step, the anthraquinone work In carrying out the present invention a conventional ing compound is gradually converted to degradation prod anthraquinone working solution which has been subjected ucts that are unable to produce hydrogen peroxide. The 55 to repeated cycles of catalytic hydrogenation and oxida rate of formation of these degradation products increases tion to produce hydrogen peroxide is used as the feed. as the temperature of the working solution being hydro The Working solutions which can be used in the present genated and oxidized is elevated. Additionally, as the pro invention are those that contain anthraquinone Working portion of the working compound which is hydrogenated compounds such as 2-ethylanthraquinone or the 2-iso. per pass through the system (also termed "depth of hydro 60 propyl-, 2-sec-butyl-, 2,5-butyl-, 2-sec-amyl-, 2-methyl- or genation') is increased, the amount of degradation prod 1,3-dimethyl-derivatives of anthraquinone as well as other ucts also rises sharply. anthraquinones well known in the hydrogen peroxide art. During the cyclic processing, these anthraquinone work These Working compounds are dissolved in at least one ing compounds also undergo hydrogenation of other than Solvent to form the anthraquinone working solutions; two the quinone groups during the catalytic hydrogenation 65 or more mixed solvents may be used to enhance the solu step. This results in the gradual formation of correspond bility of an anthraquinone working compound in both its ing tetrahydroanthraquinone derivatives of the working hydrogenated form, i.e., the hydroquinone form, and its compound. These compounds, unlike the degradation oxidized form, i.e., the quinone form. products discussed above, will produce hydrogen peroxide In accordance with the present process, the anthra upon cyclic reduction and oxidation in the same manner 70 quinone Working solution which contains degradation as the original anthraquinone working compound. Ac products resulting from cyclic processing is first treated 3,432,267 3 4 with ozone. During the ozonization stage the working metal hydroxide is from about 5 to about 25 weight per solution is passed into a treating tank and the OZone is cent. The preferred alkali metal hydroxide, for reasons passed through the working solution. In a batch type of economy, is sodium hydroxide at concentration levels treatment the ozonization may be carried out in a simple of about 5-10%. The working solution is then extracted tower with candles at the base of the tower to permit with the above aqueous alkali metal hydroxide solution the ozone gas to pass uniformly upwards through the 5 by intimately contacting the two solutions. If desired, a working solution. More complex scrubbing units can also scrubbing apparatus can be employed in which the solu be used in order to promote better gas-liquid contact tions are mechanically agitated while contacting each between the ozone and the working solution. Alternately, other. ozonization may be carried out simultaneously with any The temperature of the extraction operation is not other stage of the anthraquinone process in which the 10 critical; it can take place at temperatures of from ambient working solution is treated, except the catalytic hydrogen room temperature up to 150° C. However, it is preferred ation stage. The ozone may be introduced alone or in to carry out the caustic extraction at from 50 to 70° C. admixture with other gases, e.g., oxygen, air or nitrogen. because phase separation of two liquids is facilitated by The ozonization stage can be carried out at any tempera higher temperatures. At the end of the extraction stage, ture of from -10° C. to about 100° C.; high tempera the aqueous alkali metal hydroxide solution that separates tures, e.g., above 100° C. are not desirable since rapid from the working solution is colored a dark red. The sep decomposition of ozone occurs. arated working solution' becomes clearer and turns a The amount of ozone which is effective in treating the lighter color after extraction. working solution will of course depend upon the amount 20 Upon separation of the aqueous alkaline hydroxide of degradation products in the working solution that must solution, the remaining working solution is then passed be converted and the manner in which the ozonization in contact with either activated alumina or activated is performed. For example, in a batch type ozonization, magnesia. The temperature at which the working solution an effective amount of ozone can be passed through the contacts the activated magnesia or activated alumina is batch of working solution by introducing a gas stream 2 5 not critical and can range from about ambient tempera containing at least about 0.01 weight percent ozone (about ture up to about 1500 C. However, temperatures of from 0.01 to about 3 weight percent ozone can readily be about 50 to 150° C. are preferred, since the regeneration produced by conventional ozonators) and continuing the proceeds more rapidly at elevated temperatures. flow of ozone for from 20 minutes to 10 hours; an excess Any activated alumina or magnesia may be employed of ozone is desired to insure a rapid and complete reac 30 in the present invention.
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