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United States Patent (19) 11 4,397,788 Sakakibara Et Al

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United States Patent (19) 11 4,397,788 Sakakibara Et Al United States Patent (19) 11 4,397,788 Sakakibara et al. 45) Aug. 9, 1983 54 PROCESS FOR PRODUCING RHODIUM 1298.331 11/1972 United Kingdom................ 568/454 COMPOUNDS 1338225 11/1973 United Kingdom ... ..., 568/454 1357735 6/1974 United Kingdom.... ... 568/454 (75) Inventors: Tadamori Sakakibara; Yoshihisa 1440413 6/1976 United Kingdom ..., ..., 568/454 Matsushima; Yukio Nagashima; Nobukazu Okamoto; Katsumi OTHER PUBLICATIONS Kaneko, all of Ooi; Yohio Ishii, Paulik, "IV Modified Rhodium Catalysts', Catalytic Nagoya; Shozo Wada, Zushi, all of Reviews, vol. 6, No. 1, pp. 66-83, 1972. Japan Cornils et al., "Oxo with Rhodium Catalysts', Hydro carbon Processing, vol. 6, pp. 83-91, 1975. 73) Assignee: Toa Nenryo Kogyo Kabushiki Kaisha, Powergas et al., "Low-Pressure Oxo Process Yields a Tokyo, Japan Better Product Mix', Chemical Engineering, No. 26, (21) Appl. No.: 238,045 pp. 109-115, 1977. Kuno, "Development in Oxo Synthesis Technology', 22) Filed: Feb. 25, 1981 Journal of Synthetic Organic Chemistry, Japan, vol. 35 (8), pp. 683-688, 1977. Related U.S. Application Data Garroa et al., "Redistribution of Reactions of Organo (62) Division of Ser. No. 73,664, Sep. 7, 1979, abandoned. metallic Complexes”, Inorganic Chemistry, vol. 15, No. 3, 1976, pp. 646–647. 30 Foreign Application Priority Data Evans et al., "The Reaction of Hydridocarboxylites Oct. 4, 1978 JP Japan ................................ 53-121456 (Triphenylphosphine)rhodium with Carbon Monoxide Oct. 4, 1978 JP Japan ................................ 53-121457 and of the Reaction Product, Hydridodicarbonyl-bis(- triphenylphosphine) Rhodium and Dimeric's Splices 51) Int. Cl............................. C07F 9/74; C07F 9/92 with Hydrogen', J. Chem. Soc. (A), 1968, pp. 52) U.S.C. ..................................... 260/441; 260/446 2660-2665. 58) Field of Search .................... 568/454; 260/448 C, Steele et al., "Mixed Ligand Carbonyl Complexes of 260/440, 446, 441 Rhodium (I) and Rhodium (III)', J. C. S. Dalton, 1972, 56) References Cited pp. 2161-2169. Sequoia, "Preparation and Reactivity of some Halogen U.S. PATENT DOCUMENTS Bridged Complexes of Rhodium (I)”, J. Organometal. 3,168,553 2/1965 Slaugh .............................. 260/340.3 Chem., vol.43, 1972, pp. 425-430. 3,459,780 8/1969 Wilkinson ...... 260/429 3,487,1 12 12/1969 Paulik et al. ........................ 568/454 Baker et al., "The Preparation and Crystal Structure of 3,527,809 9/1970 Pruett et al. ........................ 568/454 tris-triphenylphosphinetic-phenylarsinerhodium (I) 3,794,671 2/1974 Wilkinson ........................... 568/4.54 Hydride", Chemical Comm. (17) 1970, pp. 1077-1078. 3,821,311 6/1974 Hughes et al. ...................... 568/454 Primary Examiner-Charles F. Warren 3,857,900 12/1974 Wilkinson ........................... 252/431 Assistant Examiner-Raymond Covington 3,939,188 2/1976 McVicker ....................... 252/431 P 3,946,082 3/976 McVicker ........................... 568/463 Attorney, Agent, or Firm-Rebecca Yablonsky 4,012,450 5/1977 Bond ................................... 568/454 (57) ABSTRACT 4,052,461 10/1977 Tinker et al. ....................... 568/.429 4,259,530 3/1981 Matsushima et al. ............... 568/454 This invention relates to rhodium compounds having 4,288,634 9/1981 Sakakibara et al. ................ 568/4.54 the general formula: FOREIGN PATENT DOCUMENTS 992101 6/1976 Canada ................................ 568/454 44-10765 5/1969 Japan ................................... 568/454 50-123611. 9/1975 Japan .............................. 260/429 R. wherein X is phosphorus, arsenic or antimony; Y is 4,397,788 Page 2 arsenic or antimony when X is phosphorus, Y is phos- propylene with carbon monoxide and hydrogen in the phorus or antimony when X is arsenic, or Y is phospho- presence of HRh(CO)PPh3)2(AsPh3)/excess PPh3 and rus, arsenic or antimony when X is antimony; R and R' AsPh3 or HRh(CO)(PPh3)(AsPh3)2/excess PPh3 and are aryl groups; and n is an integer of 1 or 2. Further, it AsPh. relates to a process for the preparation of aldehydes by the hydroformylation of olefins in the presence of a rhodium catalyst, and more particularly for the produc tion of aldehydes by the reaction of olefins such as 1 Claim, 2 Drawing Figures U.S. Patent Aug. 9, 1983 sheet 1 of 2 4,397,788 F.G. 930 1920 1910 1880 1870 Sum of the Pauling electro-negativities (Xip) U.S. Patent Aug. 9, 1983 Sheet 2 of 2 4,397,788 FIG. 2 2005 2000 1995 1985 1980 Sum of the Pauling electro-negativities (Kip) 4,397,788 1. 2 Nucl. Chem. Lett. 1971, 7(9)877-9 (England); J. Chem. PROCESS FOR PRODUCING RHODIUM Soc. Dalton Trans. 1972 (19) 2161–9 (England) and U.S. COMPOUNDS . Pat. No. 3,459,780. As a method for synthesizing these compounds, it has been proposed to add to a binuclear rhodium compound (RhCl(CO)L)2 wherein L is tri This is a division of application Ser, No. 73664, filed phenylphosphine, triphenylarsine or triphenylstibine in 9/7/79, now abandoned. " warm benzene an ether solution of 2 mols (equimolar BACKGROUND OF THE INVENTION amount) of L' being triphenylphosphine, triphenylar 1. Field of the Invention sine or triphenylstibine but not the same as L (Journal of This invention relates to new rhodium compounds O Organometallic Chemistry, Vol. 43, No. 2, 1972, page and a process for producing the same. More particu 425). • * , larly, it is concerned with new rhodium compounds Other references of lesser interest, noted because they having a structure isoelectronic to HRh(CO)(PPh3)3 concern rhodium-containing compounds, are U.S. Pat. and a process for the selective production of the same. Nos. 3,939,188 and 3,946,082, which relate to com Further, it relates to use of such products as catalysts in 5 pounds containing reduced, zero valent rhodium and the oxo process, . 4,052,461 which relates to ionic rhodium compounds 2. Description of the Prior Art, but not the hydrides which are non-ionic. Carbonyl tris (triphenylphosphine) rhodium hydride However, mixed ligands-containing rhodium.com is known as a catalyst having activity in various chemi pounds having a structure isoelectronic . to cal reactions for organic syntheses, for example, in hy 20 HRh(CO)(PPh3)3 or three stibines-coordinated rho droformylation. (Japanese Patent Publication No. dium compounds cannot be obtained, or mixtures of 10730/1970 equivalent to U.S. Pat. No. 3,527,809). See various rhodium compounds are only obtained, by the also U.S. Pat. No. 3,821,311 and Canadian Patent above described method or other known methods and it 992,101. As rhodium compounds having a structure is very difficult to isolate such compounds in a pure isoelectronic thereto are known carbonyl tris(triphenyl 25 form. phosphite) rhodium hydride HRh(CO)(P(OPh)3)3(Brit Rhodium phosphine type or rhodium-phosphite type ish Pat. No. 1338225), carbonyl tris(triphenylarsine) complexes are known as catalysts for the hydroformyla rhodium hydride HRh(CO)(AsPh3)3 and carbonyl tris tion of olefins. The stability of a rhodium catalyst is (triphenylarsite) rhodium hydride HRh(CO)(As increased by modification with phosphine, arsine, or (OPh)3)3 (British Patent No. 1357735). As to producing 30 stibine, which permits practicing the oxo reaction at a these compounds, some processes are known. In the rather low pressure. case of HRh(CO)(PPh3)3, for example, there have been According to Japanese Pat. No. 903,326, straight proposed (1) a process comprising reacting rhodium chain-rich aldehydes are prepared at a low total pres trichloride trihydrate, excess triphenylphosphine, an sure with a low partial pressure of carbon monoxide and aqueous solution of formaldehyde and sodium borohy 35 a high partial pressure of hydrogen in the presence of a dride in boiling ethanol (Journal of the Chemical Soci rhodium triarylphosphine catalyst and a triarylphos ety (A), 1968, page 2660), (2) a process comprising phine ligand in a large excess to the rhodium. However, reacting carbonyl bis(triphenylphosphine) rhodium this method has the disadvantage that the hydroformy chloride, excess triphenylphosphine and sodium boro lation reaction rate of an olefin is markedly decreased hydride in boiling ethanol (ibid) and (3) a process com 40 because of using a ligand in a large excess to rhodium, prising contacting carbonyl bis(triphenylphosphine) and a considerable quantity of a paraffin is formed by rhodium chloride and excess triphenylphosphine with the hydrogenation of the olefin ("Hydrocarbon Pro synthesis gas (mixture of H2 and CO) at a temperature of cessing' (4) 112 (1970) due to the reaction at a low total at least 55' C. under a pressure of at least 10 atm. (Japa pressure with a low partial pressure of carbon monoxide nese Patent Publication No. 17572/1978). 45 and a high partial pressure of hydrogen. However, carbonyl tris(triphenylstibine) rhodium Rhodium catalysts in combination with arsines or hydride HRh(CO)(SbFh3)3 having a structure isoelec stibines instead of phosphines have been proposed, but tronic to the above described rhodium compounds has the studies thereof have not been made so intensively not been synthesized and isolated. Moreover, as is evi because of their lower activity compared with tertiary dent from the foregoing description, all the rhodium 50 phosphine-rhodium catalysts. compounds having the above described known struc tures contain respectively a single kind of ligand and SUMMARY OF THE INVENTION those containing different kinds of mixed ligands, for Applicants have made various efforts to obtain new example, phosphines and arsines in the same molecule, rhodium compounds having a structure isoelectronic to are not known, although some monovalent rhodium 55 HRh(CO)(PPh3)3 and, as a result, have succeeded in compounds containing mixed ligands in the same mole obtaining new rhodium compounds represented by the cule are known, for example, carbonyl triphenylphos following general formula in high yield and in a pure phine triphenylarsine rhodium chloride form, thus accomplishing the present invention.
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