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United States Patent (19) [11] 3,832,391 Parshall (45) Aug

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United States Patent (19) [11] 3,832,391 Parshall (45) Aug United States Patent (19) [11] 3,832,391 Parshall (45) Aug. 27, 1974 54 CATALYSS BY DISPERSIONS OF METAL 260/570.8 R, 260/5709, 260/593 R HALDES IN MOLTEN (51) int. Cl........................ C07c51/14, C07c45/08 TRHALOSTANNATE (II) AND 58) Field of Search... 260/604 HF, 533 A, 533 AN, TRIHALOGERMANATE (II) SALTS 260/497 B, 497 V 75) Inventor: George W. Parshall, Wilmington, 56) References Cited Del. UNITED STATES PATENTS 73) Assignee: E. I. du Pont de Nemours and 3,700,706 10/1972 Butter......................... 260/533 AX Company, Wilmington, Del. FOREIGN PATENTS ORAPPLICATIONS 22 Filed: Dec. 30, 1971 1,965,942 10/1970 Germany........................ 200/533 A 21 Appl. No.: 214,376 Primary Examiner-Lorraine A. Weinberger Related U.S. Application Data Assistant Examiner-Richard D. Kelly 60) Division of Ser. No. 92,541, Nov. 24, 1970, Pat. No. 3,657,368, Continuation-in-part of Ser. No. 727,710, 57 ABSTRACT May 8, 1968, Pat. No. 3,565,823. Dispersions of transition and other metal halides in 52 U.S. CI........ 260/497 A, 260/410.5, 260/410.6, molten tetrahydrocarbylammonium or phosphonium 260/410.9 R, 260/413, 260/468 M, 260/469, trihalostannate (II) and trihalogermanate (II) salts are 260/476 R, 260/483, 260/485 R, 260/485 G, useful as catalysts for the hydrogenation, isomeri 260/491, 260/514 M, 260/515 R, 260/598, zation or carbonylation of olefins and the hydrogena 260/599, 260/601 R, 260/604 HF, 260/409, tion of nitriles. 260/497 R, 260/526 R, 260/563 R, 9 Claims, No Drawings 3,832,391 1 2 CATALYSS BY DESPERSIONS OF METAL catalyst for the hydrogenation of terminal olefins and HALIDES IN MOLTEN TRIHALOSTANNATE (I) for the hydrogenation and isomerization of dienes. AND TRHALOGERMANATE (II) SALTS 11. L. J. Kehoe et al., J. Org. Chem., 35, 2846 (1970). Solutions of chloroplatinic acid and SnCl2 in RELATED APPLICATION 5 ketones or ethers are used to catalyze the carbonyla This application is a division of my copending appli tion of terminal olefins to alkyl esters. cation Ser. No. 92,541, filed Nov. 24, 1970, and now U.S. Pat. No. 3,657,368, itself a division and continua SUMMARY OF THE INVENTION tion-in-part of my copending application Ser. No. This invention is directed to processes employing as 727,710 filed May 8, 1968, and now U.S. Pat. No. O catalysts the liquid dispersions of my above-identified 3,565,823. copending application. These dispersions, which in clude molecular dispersions, consist essentially of: (A) BACKGROUND OF THE INVENTION at least 0.05 weight percent of a chloride-, bromide- or A. Field of the Invention iodide-containing salt of a metal having an atomic num 5 ber of 26-28, 44-46 or 76-78, and (B) a molten salt This invention relates to the use of the dispersions of of a compound of the formula (R'R'R'R''QYXa metal halides in molten quaternary ammonium triha wherein R, R, R and R, independently, contain up lostannate(II) or trihalogermanate(II) salts of my to 18 carbons and are alkyl, cycloalkyl, aryl, alkaryl or above-mentioned application as catalysts in processes aralkyl; or R and R', conjointly, contain 4 to 6 carbons for hydrogenating, isomerizing and carbonylating ole and is alkylene; or R, R, R and Q conjointly is pyri fins and for hydrogenating nitriles. dinium or quinolinium; Q is nitrogen or phosphorus; Y B. Description of the Prior Art is tin or germanium; and X is chlorine or bromine. The dispersions can be made, for example, by mixing The following references are of interest in connec components A and B at a temperature above the melt tion with the invention of this application: 25 ing point of component B, as is fully disclosed in my co 1. R. D. Cramer et al., J. Am. Chem. Soc., 85, 1691 pending application. Dispersions formed and claimed (1963). Solutions of chloroplatinic acid and stannous in the copending application include the following: chloride are effective catalysts for the hydrogenation of N,N,N,N-tetraethylammonium trichlorostannate(II) olefins. - containing: PtCl2, PdCl2; RuCls hydrate; RhCl3 hydrate; 2. G. C. Bond et al., J. Catal.., 7, 217 (1967). Solu 30 IrCl34HO, OsCl ReCls, CoCl2, CoCl26H2O, tions of chloroplatinic acid and stannous chloride are HPtClinHO; FeCl; FeCls, MnOl. CrCl; CrCla; effective catalysts for the isomerization of 1-pentene to VC, TiCl, NiCl, NiBr. NiI6HO; IrBra; KPtCl; its equilibrium mixture with 2-pentenes. KPdCI, WCls, MoCla; (Etap):PtCl(Et is ethyl); 3. H. van Bekkum et al., J. Catal. 7, 292 (1967). So (NO)RuOl3HO; AuCla; and lutions of chloroplatinic acid and stannous chloride 35 N.N.N,N-tetraethylammonium trichloroger catalyze the hydrogenation of cyclohexene and the se manate(II) containing: NiBréHO, CoCl2, PdCl2; lective hydrogenation of dienes to monoenes. RuCl3HO, RhCls HO, etc. 4. L. P. van't Hoffet al., J. Catal.., 7, 295 (1967). So In the present invention, all the above-mentioned dis lutions of chloroplatinic acid and stannous chloride are persions serve as catalysts in: used as catalysts for the hydrogenation of soybean oil. 40 A. A process for the hydrogenation of olefins and ni Methyl linoleate gives predominantly methyl oleate. triles and for the isomerization of olefins; and 5. E. L. Jenner et al., U.S. Pat. No. 2,876,254 (1959). The carboxymethylation of propylene gives a product B. A process for the carbonylation of olefins. mixture containing approximately equal amounts of A. HYDROGENATION AND ISOMERIZATION methylbutyrate and methyl isobutyrate. 45 The process for the hydrogenation of olefins or ni 6. F. N. Jones, J. Org. Chem., 32, 1667 (1967) and triles is conducted by heating a mixture of hydrogen U.S. Pat. No. 3,397,252 (1968). Inter alia, vinyl chlo and an olefin, including a cycloolefin, or a nitrile in the ride is reductively coupled to yield butadiene by Sn(II presence of a catalytically effective amount of at least in solutions containing catalytic amounts of PtCl2, ce one of the above-noted metal halide-trihalostannate(II) sium fluoride acting as cocatalyst. 50 or -trihalogermanate(II) dispersions at a temperature The following art may also be of interest: of at least the melting point temperature of said disper 7. Th. Kruck et al., Angew Chem. internat. Edit., 8, sion, 679 (1969). The reaction of trichlorostannate salts Any olefin can be hydrogenated according to the in with metal carbonyls is used to produce complexes vention, but the reaction may be expressed more par containing the SnCls ligand. Tetraethylammonium tri 55 ticularly by the equation which follows (A signifies that chlorostannate is used in one experiment although not the temperature is high enough to keep the catalyst above its melting point. molten): 8. Japanese Patent 7,005,255 (1970). Aliphatic poly olefins will hydrogenate to monoolefins with the cata 60 R5 R8 Rs. Rs N A lyst HPtSnCl(PR). C=C - H -- H-C-C-H 9. W. Wilkinson, U.S. Pat. No. 3,501,531 (1970). / cat. Complexes prepared from mixtures of rhodium chlo R7 R8 R7 R8 ride and stannous chloride are used as catalysts for the hydroformylation of olefins. 10. R. W. Adams et al., Inorg. Nucl. Chem. Letters, 65 wherein R, R, R and R, individually, are hydrogen, 4,455 (1968). A mixture of dichlorobis(triphenylphos alkyl of up to 12 carbons, alkenyl of up to 12 carbons, phine)-platinum and stannous chloride is effective as a aryl of up to 10 carbons, aralkyl of up to 10 carbons, 3,832,391 3 4 alkaryl of up to 10 carbons, aralkenyl of up to 10 car position of the group consisting of hydrogen, water and bons, alkoxycarbonylalkyl of up to 14 carbons, alkox alcohols. Except for the reactants, all three of these re ycarbonylalkenyl of up to 14 carbons, -COOR or actions employ essentially the conditions of the hydro -COR where R is lower alkyl; or R and R conjointly genations noted above. is alkylene or alkenylene of 4 to 6 carbons; or R and Hydroformylation is conducted by heating a mixture R is alkylene or alkenylene of up to 10 carbons or the of carbon monoxide, hydrogen and any olefin in the divalent radical of the formula:- presence of a catalytically effective amount of at least one of the metal halide-trihalostannate(II) or -trihalo -(-CH2-)-CH CH-CH-)-CH A. CH-CH2-)-2, germanate(II) dispersions at a temperature of at least with the proviso that at least two of R, R, R and R' 10 the melting point temperature of said dispersion. The are hydrogen. Included within the definition of the ole process of hydroformylation may be particularly ex fin are 1,5-cyclooctadiene, 1,5-cyclododecadiene and pressed by the equation: l,5,9-cyclododecatriene. t In the hydrogenation of olefins, as in all the processes of the invention, an effective catalytic amount of the 15 dispersions of my above-mentioned application or mix tures thereof is used. In general, an effective catalytic amount will be dependent upon the conditions, the re Rs R6 actants, the particular process and metal halide disper Yc-c -- H -- CO A ( R7 R8 sion. Preferably, 0.005 to 10 weight percent of the 20 RF R8 cat, \ H R R' metal halide in the dispersion based on the olefin reac OscC-C-C-H tant is used. Most preferably, 0.5 to 5 weight percent k k. of the metal halide in the dispersion is used. The rates of reaction of the processes are dependent upon the temperature and the reactants used.
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