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United States Patent (19) 11 4,298,533 Moriya Et Al

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United States Patent (19) 11 4,298,533 Moriya Et Al United States Patent (19) 11 4,298,533 Moriya et al. 45 Nov. 3, 1981 54). PRODUCTION OF MALEICANHYDRIDE 56) References Cited U.S. PATENT DOCUMENTS (75 Inventors: Koji Moriya; Itsuo Furuoya, both of 3,856,824 12/1974 Raffelson et al. .............. 260/346.75 Osaka, Japan 3,899,516 8/1975 Dickason........... ... 260/346.75 73) Assignee: Takeda Chemical Industries, Ltd., 4,220,595 9/1980 Dickason et al. .............. 260/346.75 Osaka, Japan FOREIGN PATENT DOCUMENTS 2255394 8/1973 Fed. Rep. of 21 Appl. No.: 915,301 Germany ........................ 260/346.75 1368168 9/1974 United Kingdom . 22 Filed: Jun. 13, 1978 Primary Examiner-Henry R. Jiles Assistant Examiner-Bernard Dentz Related U.S. Application Data Attorney, Agent, or Firm-Wenderoth, Lind & Pomack 62) Division of Ser. No. 560,802, Mar. 21, 1975, Pat. No. 57 ABSTRACT 4,108,874. Maleic anhydride is obtained in a high yield as well as in a high purity by oxidation of a hydrocarbon of not less 30 Foreign Application Priority Data than four carbon atoms in gaseous phase in the presence Apr. 9, 1974 JP Japan .................................. 49-40566 of a catalyst comprising (a) vanadium oxide, (b) phos May 22, 1974 JP Japan .................................. 49-58117 phorus oxide, (c) thallium oxide and/or alkaline earth metal oxide, and if necessary, further containing (d) iron 51) Int. Cl. ............................................ CO7D 307/60 oxide. 52 U.S. Cl. ................................................ 260/346.75 58) Field of Search .................................... 260/346.75 5 Claims, No Drawings 4,298,533 1. 2 known perse for the manufacture of solid catalysts, one PRODUCTION OF MALEIC ANHYDRIDE of which, for example, may be as follows. Thus, a vanadium-containing compound, a phos This is a division of application Ser. No. 560,802, filed phorus-containing compound, a thallium-containing Mar. 21, 1975, now U.S. Pat. No. 4,108,874. 5 compound and/or an alkaline earth metal-containing The present invention relates to a method for the compound, and, if required, an iron-containing com production of maleic anhydride. More specifically, the pound, each of which can be converted to the corre invention relates to a method for the production of sponding oxide by heating or through a chemical reac maleic anhydride by oxidation of a hydrocarbon of not tion, are dissolved, as required, in a suitable solvent such less than four carbon atoms in gaseous phase in the 10 as water or alcohol, and a carrier is impregnated with presence of a catalyst comprising (a) vanadium oxide, the resulting solution or solutions. The impregnated (b) phosphorus oxide, (c) thallium oxide and/or alkaline carrier (catalyst intermediate) is then calcined at 300 to earth metal oxide, and if necessary, further containing 800° C., preferably at 400 to 600 C., for 1 to 20 hours, (d) iron oxide. preferably 2 to 10 hours. Heretofore, in the production of maleic anhydride by 15 As the aforementioned vanadium-containing com catalytic oxidation of hydrocarbons of not less than four pound, there may be mentioned vanadium oxides carbon atoms such as butane, butene-1, butene-2, butadi (V2O5, V2O4, V2O3, etc.), vanadates (NH4VO3, vana ene, cyclopentadiene, benzene and hydrocarbon materi dyl oxalate, vanadyl sulfate, vanadyl chloride, etc.) and als containing them (e.g. BB fraction, spent BB fraction, so on. As said phosphorus-containing compound, there etc.), it was known to employ a catalyst composed of may be mentioned phosphorus oxides (P2O5, P2O3, vanadium oxide and phosphorus oxide or a catalyst etc.), phosphoric acids (HPO3, H3PO4, H4P2O7, comprising, in addition to vanadium and phosphorus H3PO3, etc.), phosphates ((NH4)3PO4, (NH4)2HPO4, components, a third component such as lithium oxide, (NH4)H2PO4, etc.), phosphorus halides (PCl3, PCls, iron oxide, copper oxide or chromium oxide. However, PBr3, etc.) and so on. As the thallium-containing com with these catalysts, the yields and purities of the prod 25 pound, there may be mentioned thallium oxides (Tl2O, uct have not been fully satisfactory, especially when a Tl2O3), thallium nitrates, thallium halides (TiCl, hydrocarbon material including butane, for example, TlCl3.4H2O, TIF3, TlBr, TIBr3.4H2O, TII, TI3, etc.), thallium sulfates (Tl2SO4, Tl2(SO4)3.7H2O), thallium spent BB fraction, spent-spent BB fraction, etc. is used. carbonate, organic acid thallium salts (e.g., Tl(HCOO), To obviate these disadvantages we conducted inten 30 Tl(CH3COO), CH2(COOTf)2) and so on. The afore sive research, and have found that the above disadvan mentioned alkaline earth metal-containing compound is tages are removed by employing thallium oxide and/or exemplified by alkaline earth metal salts (nitrates, e.g. alkaline earth metal oxide as a third component in addi beryllium nitrate, magnesium nitrate, calcium nitrate, tion to vanadium oxide and phosphorus oxide, that is by strontium nitrate, barium nitrate, radium nitrate; ha employing a catalyst which comprises vanadium oxide, 35 lides, e.g. magnesium chloride, calcium chloride, bar phosphorus oxide, thallium oxide and/or alkaline earth ium chloride carbonates, e.g. magnesium carbonate, metal oxide, and if necessary further containing iron strontium carbonate, barium carbonate; sulfates, e.g. oxide. The present invention is accomplished on the calcium sulfate, barium sulfate; organic acid salts, e.g. basis of these new findings, magnesium acetate, calcium acetate; and so on), alkaline It is an object of the present invention to provide an 40 earth metal hydroxides (e.g. magnesium hydroxide, industrially feasible method for the production of ma calcium hydroxide, strontium hydroxide, barium hy leic anhydride in a high yield as well as in a high purity droxide), alkaline earth metal oxides (e.g. beryllium by oxidation of a hydrocarbon of not less than four oxide, magnesium oxide, calcium oxide, strontium ox carbon atoms in gaseous phase. ide, barium oxide, radium oxide) and so on. Another object of the present invention is to provide 45 As the aforementioned iron-containing compound, a novel, highly active and long-life catalyst useful for there may be mentioned iron oxides (Fe2O3, Fe3O4), the production of maleic anhydride in a high yield as iron hydroxides (Fe(OH)3, Fe(OH)2), iron nitrates (Fe(- well as in a high purity by oxidation of a hydrocarbon of NO3)2.9H2O, Fe(NO3)2.6H2O), iron chlorides (e.g. not less than four carbon atoms in gaseous phase. FeCl3.6H2O, FeCl2.nH2O), iron alums, iron sulfates Other objects will be apparent hereinafter. 50 (e.g. Fe2(SO4)3.nH2O), organic acid iron salts (e.g. The catalyst used according to the present invention FeC4H2O4, FeC2O4.2H2O), iron phosphates (FePO4.n- comprises, as active ingredients, any of a compound H2O, Fe3(PO4)2.8H2O) and so on. Thus, in each in oxide or a mixture of vanadium oxide, alkaline earth stance, oxides or compounds which can be easily con metal oxide and phosphorus oxide; a compound oxide verted to oxides are employed. or mixture of vanadium oxide, thallium oxide and phos 55 In the manufacture of the catalyst to be employed in phorus oxide; a compound oxide or mixture of vana the practice of the present invention, the proportions of dium oxide, alkaline earth metal oxide, phosphorus said vanadium-containing compound, phosphorus-con oxide and thallium oxide; a compound oxide or mixture taining compound, thallium-containing compound and of vanadium oxide, alkaline earth metal oxide, phospho alkaline earth metal-containing compound may be var rus oxide and iron oxide; a compound oxide or mixture 60 ied, although the atomic ratio of vanadium to phospho of vanadium oxide, phosphorus oxide, thallium oxide rus is preferably 2:1 to 1:10 and, for still better results, and iron oxide; or a compound oxide or mixture of 1:1 to 1:5, and the atomic ratio of vanadium to thallium vanadium oxide, alkaline earth metal oxide, phosphorus is preferably 1:5 to 100:1 and, for still better results, 1:2 oxide, thallium oxide and iron oxide; and usually, each to 20:1. The atomic ratio of vanadium to alkaline earth of these compound oxides or mixtures is used as sup 65 metal is 1:10 to 40:1 and, for still better results, 1:5 to ported on a carrier. 15:1. When the catalyst contains iron as well, the atomic The catalyst to be employed in the practice of the ratio of vanadium to iron is preferably 1:5 to 100:1 and, present invention can be prepared by procedures for still better results, 1:2 to 20:1. 4,298,533 3 4. As for the carrier material, heat-resistant inorganic (4) a high yield even when a hydrocarbon material compounds such as, alumina, silicon carbide, titanium including butane is used as a starting material; and also oxide, silica, magnesia, diatomaceous earth, pumice, enables an increase in the space-time yield (STY) more Zirconia, cerium oxide, titanium phosphate, aluminum easily than has been possible with the prior art method, phosphate, silicon phosphate, gypsum and their mix in addition to the increased amenability to purification tures may be desirably employed. While the amount of which provides for a more economical production of catalytically active components to be supported de maleic anhydride in high purity. pends upon the particular type of carrier material and The following examples, are intended to further de the method of preparing the catalyst, among other con scribe the present invention. It should, however, be ditions, it is usually not less than 3 percent by weight 10 understood that the available methods for manufactur and, preferably, not less than 10 percent by weight. ing the catalyst are not limited to those set forth in the The method for manufacturing the catalyst to be examples but any suitable method may be adopted employed for the purposes of the present invention will within the framework of the invention thus far de be further described in detail.
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