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United States Patent (19) 11) Patent Number: 5,498,796 Deckers Et Al

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United States Patent (19) 11) Patent Number: 5,498,796 Deckers Et Al IIII USOO54987.96A United States Patent (19) 11) Patent Number: 5,498,796 Deckers et al. (45) Date of Patent: Mar 12, 1996 54 PROCESS FOR THE PREPARATION OF 56) References Cited AMINES BY CATALYTIC HYDROGENATION OF NITRLES FOREIGN PATENT DOCUMENTS 322049 6/1989 European Pat. Off. ......... BOJ 23/74 75) Inventors: Gregor Deckers, Xanten; Dieter 340848 11/1989 European Pat. Off. ............... 564,493 Frohning, Wesel, both of Germany 384542 8/1990 European Pat. Off. ..... CO7C 209748 398668 11/1990 European Pat. Off. ......... BO 23,74 73) Assignee: Hoechst Aktiengesellschaft, Germany 472918 3/1992 European Pat. Off. ......... BO1 23/74 490382 6/1992 European Pat. Off. ............... 564,493 21 Appl. No.: 426,142 Primary Examiner-Brian M. Burn 22) Filed: Apr. 19, 1995 Attorney, Agent, or Firm-Bierman and Muserlian Related U.S. Application Data 57 ABSTRACT 63 Continuation of Ser. No. 259,117, Jun. 10, 1994, abandoned, A process for the preparation of amines by catalytic hydro which is a continuation of Ser. No. 990,730, Dec. 15, 1992, genation of nitriles in the presence of a nickel-containing abandoned. support catalyst. The support catalyst contains Mg and Ni in (30) Foreign Application Priority Data coprecipitated form and in a molar ratio of 0.0075 to 0.075:1.There is 17 to 60 g of a water-insoluble support per Dec. 18, 1991 (DE) Germany .......................... 41 4771.2 mol of nickel, and 65% to 97% of the BET total Surface area of the support catalyst is formed by pores having a radius (51) Int. Cl. .......................................... CO7C 209/.48 52 U.S. Cl. ............ ... 564/493; 502/.328; 564/415 rs2.5 nm. 58 Field of Search ..................................... 564/493, 511, 564/415, 490; 502/328 30 Claims, No Drawings 5,498,796 1 2 PROCESS FOR THE PREPARATION OF (BET) method which is described in the J. Amer. Chem. Soc. AMNES BY CATALYTIC HYDROGENATION 60., (1938) page 309. As a result of the aforementioned OF NITRLES narrow distribution of pore radii (limited to rs2.5 nm), the catalyst gains certain special properties which lead to an This application is a continuation of application Ser. No. 5 increase in activity and an improvement in the selectivity of 08/259,117 filed Jun. 10, 1994, now abandoned, which is a the reaction which form the basis of the present invention. continuation of Ser. No. 07/990730, filed Dec. 15, 1992, now abandoned. DETAILED DESCRIPTION OF THE This Application claims the benefit of priority of German INVENTION Application 41 41 771.2, filed Dec. 18, 1991. O The present invention relates to a process for preparing A feature of the catalyst is its composition, indicated by amines by catalytic hydrogenation of nitriles in the presence the molar ratio of Mg to Ni. As previously mentioned, in of a nickel-containing, Supported catalyst. The catalytic reduced form, the catalyst contains Mg and Ni in a molar hydrogenation of nitriles, in particular saturated or unsatur ratio of 0.0075 to 0.075:1. It has proven particularly suc ated fatty acid nitriles, leads to the corresponding saturated 15 cessful to select a molar ratio of Mg:Ni of 0.015 to 0.060:1, or unsaturated primary or secondary amines, depending on more preferably 0.022 to 0.055:1. 1 mol of Mg or 1 mol of the starting material and the reaction conditions selected in Mg" corresponds to 24.305 g of Mg or 24.305 g of Mg'", each case. and 1 mol of Ni or 1 mol of Ni" corresponds to 58.71 g of Ni or 58.71 g of Ni’". When the catalyst is in its reduced BACKGROUND OF THE INVENTION 20 state, the magnesium is present as Mg' and the nickel mainly or almost completely in metallic form. The definition EP 384 542 describes a process for preparing secondary of the molar ratio is precisely worded as the ratio of mols of alkylamines by catalytic hydrogenation in the presence of a Mg':(mol of Ni--mol of unreduced Ni). nickel-containing catalyst which contains copper, and The composition of the novel catalystis further defined by optionally cobalt as a promoter. 25 the ratio of the parts by weight of the water-insoluble DE 39 14875 C2 relates to a process for the catalytic Support to nickel, the term nickel again being understood to hydrogenation of aliphatic nitriles to amines using a nickel mean the sum of the mols of metallic nickel and the mols of catalyst on a support containing magnesium oxide and Ni2. silicon dioxide. The catalyst has a molar ratio of silicon Various water-insoluble materials are suitable as supports. dioxide to nickel of between 0.1 and 0.3 and a molar ratio 30 These include silicates, such as calcium, magnesium and/or of magnesium to nickel of between 0.25 and 0.05, as well as aluminium silicates; Al-O, SiO, and/or kieselguhr. Mag an average pore radius of 1.5 to 4.0 nm. nesium silicates (especially in the form of pumice), Al-O, However, despite comparatively good hydrogenation and/or kieselgur, are especially useful. Pumice, AO, SiO, results, the state-of-the-art processes generally have some and/or kieselguhr are preferred and SiO, and/or kieselguhr weaknesses, including (1) the reaction conditions (pressure, 35 deserve special mention as being most preferred. Kieselguhr temperature), (2) the activity of the catalyst used for hydro has proven particularly successful. genation, (3) the filterability of the catalyst, and (4) the The support material should normally be present in the selectivity of the reaction. Furthermore, it is desirable to form of fine particles. Its particles should exhibit a grain size have a process with a wide range of applications which of 1 to 30, in particular 2 to 25, preferably 3 to 20 um. The makes it possible to prepare, as desired, a saturated primary 40 catalyst contains 17.0 to 60.0, in particular 25 to 50, pref amine, a saturated secondary amine, or an unsaturated erably 30 to 40 g of support per mol of Ni. As already primary amine, in high yields. mentioned herein, moles of nickel is understood to mean the total nickel in both reduced and unreduced form. The active SUMMARY OF THE INVENTION 45 nickel metal surface area of the catalyst is 110 to 180, in This problem is solved by a process for preparing amines particular 125 to 160, preferably 130 to 150 m/g of nickel. by catalytic hydrogenation of nitriles in the presence of a It is determined on the basis of a method described in the nickel-containing supported catalyst, with the optional addi Journal of Catalysis 81, (1983) page 204 and 96, (1985) page tion of ammonia, at elevated temperature and optionally at 517 by measurement of the amount of hydrogen chemi elevated pressure. 50 Sorbed at 20° C. Such catalysts have the following characteristics: Of the BET total surface area, 65% to 97%, in particular 70% to 95%, preferably 75% to 95% is formed by pores (1) Mg and Ni are present in coprecipitated form having a radius rs2.5 nm (25 A). Moreover, it is a further (2) The molar ratio of Mg to Ni is 0.0075-0.075:1 improvement that 60% to 95%, in particular 70% to 95%, (3) There is 17 to 60 g of water-insoluble support per mol 55 preferably 73% to 90%, or the BET total surface area is of Ni formed by pores having a radius r of 1.5 to 2.5 nm (15 to (4) The active Nimetal surface is 110 to 180 m/g of Ni 25A). It is more advantageous if pores having a radius r of (5) 65% to 97% of the BET total surface area of the 1.8 to 2.5 nm (18 to 25 A) form 35% to 85%, in particular catalyst is formed by pores of radius rs2.5 nm. 45% to 76%, preferably 50% to 70% of the BET total A major feature of the inventive support catalyst is the 60 surface area. The pore radii are determined according to a narrow distribution of pore radii, indicated by a high pro method described in Adsorption Surface Area and Porosity portion of the BET total surface area being attributable to by S. J. Gregg and K. S. W. Sing (Academic Press New pores having a radius rs2.5 nm. The BET total surface area York-London 1967), pages 160 to 182. is 160 to 450, in particular 180 to 380, preferably 200 to 350, The process for preparing the catalyst starts with an mig of catalyst. The m” BET total surface area is under 65 aqueous solution containing nickel and magnesium salts. stood to mean the surface area determined by the adsorption This mixed salt solution contains 10 to 100, in particular 20 of nitrogen according to the Brunauer, Emmett and Teller to 80, preferably 30 to 50 g of Ni/liter. It exhibits magnesium 5,498,796 3 4 corresponding to 0.2 to 15, in particular 0.5 to 12, preferably factory to dry at temperatures of 50° to 120, in particular 1 to 10 g of MgO/liter. 55° to 100, preferably 60° to 90° C. using conventional The mixed salt solution is prepared by dissolving water processes, such as placing the material to be dried in a fixed soluble, inorganic, organic, or complex salts of nickel and or moving bed, e.g. a fluidized bed. The catalyst mixture is magnesium in water. Well-suited salts are the sulfates, reduced using hydrogen or hydrogen-containing gas mix chlorides, acetates, propionates, butyrates, and nitrates.
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