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United States Patent (19) 11) Patent Number: 4,564,514 Drauz Et Al

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United States Patent (19) 11) Patent Number: 4,564,514 Drauz Et Al United States Patent (19) 11) Patent Number: 4,564,514 Drauz et al. 45) Date of Patent: Jan. 14, 1986 (54) PROCESS FOR THE PRODUCTION OF Primary Examiner-Andrew H. Metz WATER-FREE ORGANC HYDROGEN Assistant Examiner-Terryence Chapman PEROXDE SOLUTION Attorney, Agent, or Firm-Cushman, Darby & Cushman 75 Inventors: Karlheinz Drauz, Freigericht; Axel 57 ABSTRACT Kleemann; Rolf Wirthwein, both of The production of organic hydrogen peroxide solutions Hanau, all of Fed. Rep. of Germany which are practically water-free until now has had the 73) Assignee: Degussa Aktiengesellschaft, problem of either too high a water content of the solu Frankfurt, Fed. Rep. of Germany tion or too great a loss of hydrogen peroxide through decomposition and passing over as distillate during the (21) Appl. No.: 510,162 distillative drying. By selection of specific esters in (22) Filed: Jul. 1, 1983 combination with commensurately high pressures in the azeotropic removal of water, these disadvantages can (30) Foreign Application Priority Data be avoided. Extremely low water content solutions of Jul. 7, 1982 (DE Fed. Rep. of Germany ....... 3225.307 hydrogen peroxide in high boiling solutions are pro Mar. 11, 1983 (DE) Fed. Rep. of Germany ....... 3308740 duced by mixing hydrogen peroxide solutions in sol vents whose azeotropic boiling point with water is 51) Int. Cl. ............................................ C01B 15/023 below the boiling point of hydrogen peroxide with 52 U.S. Cl. ................................. 423/589; 423/658.5; higher boiling solvents which form the highest azeo 423/584 trope with water, whose boiling point is near or above 58) Field of Search ................................ 423/584-589, the boiling point of hydrogen peroxide. Thereupon, the 423/658.5 mixture is freed from both water and the lower boiling (56) References Cited solvent. The mixture can be formed by an in situ method. Production of extremely low water containing U.S. PATENT DOCUMENTS solutions of hydrogen peroxide in high boiling solvents 3,682,781 8/1972 Jones et al. ......................... 423/584 are produced by mixing hydrogen peroxide solutions in 3,707,444 12/1972 Schreyer et al. ... 42.3/589 solvents whose azeotrope boiling point with water is 3,737,519 6/1973 Schreyer et al. ... 42.3/589 below the boiling point of hydrogen peroxide with 3,743,706 7/1973 Kabisch et al. ...... ... 42.3/588 3,755, 185 8/1973 Waldmann et al. 42.3/584 higher boiling solvents which form the highest azeo 3,761,581 9/1973 Kabisch et al. .. ... 42.3/589 trope with water, whose boiling point is near or above 3,767,778 10/1973 Giesselmann .... ... 42.3/588 the boiling point of hydrogen peroxide. Thereupon, the 3,819,818 6/1974 Giesselmann ....................... 423/589 mixture is freed from both water and the lower boiling solvent. The above-mentioned mixture can also be pro FOREIGN PATENT DOCUMENTS duced by an in situ method. 2125159 12/1972 Fed. Rep. of Germany ...... 423/529 0931 119 7/1973 United Kingdom ................ 423/589 43 Claims, No Drawings 4,564,514 1 2 peroxide concentrations of 0.28 or 0.6 weight 9% and PROCESS FOR THE PRODUCTION OF 0.26 or 0.8 weight %, respectively, in the distillate. WATER-FREE ORGANIC HYDROGEN PEROXDE Besides, there occurs an additional loss of hydrogen SOLUTION peroxide of 7.5 or 4.1 weight% and 4.7 or 3.9 weight % based on the hydrogen peroxide employed. If there is BACKGROUND OF THE INVENTION calculated the loss of hydrogen peroxide through the It is known that the water content of hydrogen perox amount of the distillate and the decomposition thus at a ide solutions is disturbing in many reactions, e.g., in distillation of 400 or 100 mbar, the total loss is at least oxidations or epoxidations, see, e.g., Organic Reactions 7-8 weight % of the hydrogen peroxide employed. Vol. 7 page 395 (1953). 10 However, if one distills at substantially lower pressure, Thus, there were early attempts to employ corre i.e., far below 100 mbar, then there are found still higher sponding organic solutions in place of pure aqueous amounts of hydrogen peroxide in the distillate which solutions. amounts can be as much as over one weight percent However in the production of these types of solutions based on the distillate; however, the examples were there are difficulties. 15 carried out at these pressures which were considered as Generally, to obtain organic hydrogen peroxide solu preferred, see loc. cit. tions, there are employed aqueous solutions of hydro gen peroxide as the starting material. These are either Also, in the use of aliphatic esters as solvents for only diluted with the desired organic compound and hydrogen peroxide, the azeotropic removal of water is subsequently the water removed by distillation or the 20 carried out at pressures which are far below 100 mbar, aqueous solutions are extracted with the organic com see British Pat. No. 931,119 Example 1. pound and if desired the water removed. Upon repeating the preparation of a solution of hy In both cases there are indeed obtained organic solu drogen peroxide in n-propyl acetate and the azeotropic tions of hydrogen peroxide whose water content, how removal of water from this solution, it has turned out ever, always is approximately 1 weight % or more, see, 25 that the distillate contains more than 0.5 weight % of e.g., German Pat. No. 2038319 and German Pat. No. hydrogen peroxide at a pressure of 65 mm. 2038320 as well as Kabisch U.S. Pat. No. 3,743,706 and Therefore, according to the state of the art, there British Pat. No. 931,119. The entire disclosures of the must be formed the impression that in a distillative dry aforementioned German patents, Kabisch U.S. Pat., and ing of organic hydrogen peroxide solutions which is to the British patent are hereby incorporated by reference 30 be carried out at a reduced pressure necessarily, as a and relied upon. consequence, there must be considerable losses of hy Thereby, according to the process of German Pat. drogen peroxide in large scale carrying out of the pro Nos. 2038319 and 2038320, there have been attempts to CeSS remove the water present in the organic solutions by However, not only the loss of hydrogen peroxide distillation at reduced pressure or by azeotropic distilla 35 represents a considerable disadvantage of the previ tion with an additional entraining agent. ously known process, additionally the distillation resi In the process of Kabisch U.S. Pat. No. 3,743,706, the dues were not free from water. extraction agent itself can be used as entraining agent Thus, the organophosphorus solutions have e.g., re for an azeotropic distillation. However, more precise sidual water contents which are between 0.97 to 9.5 details are missing. 40 weight %. However, these types of solutions cannot be Also in British Pat. No. 931,119 there is employed a employed for oxidation or epoxidation. component of the mixture for azeotropic distillation of Also, in the single example in German Pat. No. water. However, in the production of organic hydrogen 2038320, the water content in the organic phase was peroxide solutions from aqueous solutions besides the 11.4 weight %. frequent too high content of water there is manifest a 45 further, more substantial disadvantage. Thus, a task of the process of the present invention is During the removal of water at the pressures em to produce a solution of hydrogen peroxide in an or ployed, a certain percentage of hydrogen peroxide is ganic solvent in which there is no mentionable loss of entrained with the distillate which leads to substantial hydrogen peroxide employed and which solution has a losses of hydrogen peroxide. In repeating two of these 50 water content below 0.5 weight %. procedures, the losses were between 0.5 and 0.6 weight SUMMARY OF THE INVENTION %. Besides, there occur further losses through decompo It has now been found that practically water-free sition in the sump. organic solution of hydrogen peroxide can be obtained In the process of German Pat. Nos. 2,038,319 and 55 from aqueous solutions of hydrogen peroxide by mixing 2,038,320, there are employed organic phosphorus com the aqueous solutions with carboxylic acid esters if the pounds or heterocyclic nitrogen compounds, in the aqueous hydrogen peroxide solutions are mixed with process of British Pat. No. 931,119 and Kabisch U.S. alkyl or cycloalkyl esters of saturated aliphatic carbox Pat. No. 3,743,706 aliphatic or cycloaliphatic esters. ylic acids which have a total carbon atom content of While in Kabisch U.S. Pat. No. 3,743,706 there is 60 4-8 and form an azeotrope with water and the azeo present no data in regard to carrying out an azeotropic tropic removal of water is carried out at a pressure distillation, in the processes of the other three patents between 160 and 1000 mbar. mentioned, the operation is carried out at pressures far Preferably, the distillation is carried out at 200 to below 100 mbar, see the examples. 1000 mbar. Although both German patents specify a general 65 As preferred carboxylic acid esters, there are men pressure range below 400 mbar, repeating the procee tioned: of formic acid: the propylesters to the hexylest dure using triethyl phosphate or N-methyl pyrrolidone ers, e.g. propylformate, isopropylformate, n-butylfor at pressures of 400 and 100 mbar resulted in hydrogen mate, amylformate. 4,564,514 3 4 Of acetic acid: the ethyl ester to the hexyl ester, e.g., The process of the invention operates without any ethyl acetate, propyl acetate, isopropyl acetate, butyl additional entraining agent; the resulting azeotrope of acetate, sec.
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