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Provides a Process of Hydrogenating 3-Hydroxypropionalde

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Provides a Process of Hydrogenating 3-Hydroxypropionalde USOO7335800B2 (12) United States Patent (10) Patent No.: US 7,335,800 B2 Komplin et al. (45) Date of Patent: Feb. 26, 2008 (54) HYDROGENATION CATALYST AND 5,945,570 A 8/1999 Arhancet et al. ........... 568,862 HYDROGENATION METHOD 5,958,825 A 9/1999 Wulff-Doring et al. ..... 502,300 5,977,013 A 1 1/1999 Elliott et al. ................ 5O2,337 (75) Inventors: Glenn Charles Komplin, Katy, TX 6,152.975 A 1 1/2000 Elliott et al. .............. 48.197 R (US); John Anthony Smegal, Houston, 6,232,511 B1 5/2001 Haas et al. ................. 568,862 TX (US) 6,342.464 B1 1/2002 Arhancet et al. ........... 5O2/257 6,376,720 B1 4/2002 Han ........................... 568,483 (73) Assignee: Shell Oil Company, Houston, TX (US) 6,399,538 B1 6/2002 Hucul ........................ 5O2,325 ( c ) Notice: Subject tO any disclaimer, the term of this 6,429,167 B1 8/2002 Maeno et al. ............... 5O2,325 patent is extended or adjusted under 35 6,670,300 B2 12/2003 Werpy et al. ............... 502f182 U.S.C. 154(b) by 168 days. 6,911,566 B2 6/2005 Tsunoda et al. ............ 568,862 2002/0087.036 A1 7/2002 Haas et al. ................. 568/885 (21) Appl. No.: 11/409,433 2004/0097764 A1 5/2004 Tsunoda et al. ............ 568.860 2004/0225 161 Al 11/2004 Sunkara et al. ............. 568,852 (22) Filed: Apr. 21, 2006 2004/0260125 Al 12/2004 Seapan et al. .............. 568,868 O O 2005/0033099 A1 2/2005 Ryu et al. ................... 585,259 (65) Prior Publication Data 2005/0080300 A1 4/2005 Komplin et al. ............ 568,862 US 2006/0241325 A1 Oct. 26, 2006 Related U.S. Application Data FOREIGN PATENT DOCUMENTS (60) Provisional application No. 60/673,530, filed on Apr. 21, 2005. CN 1122568 C 5, 1996 CN 1342521 4/2002 (51) Int. Cl. CN 1342633 4/2002 C07C 29/14 (2006.01) CN 1428190 T 2003 BOI 2L/08 (2006.01) CN 1428322 T 2003 BOI. 23/28 (2006.01) (52) U.S. Cl. ...................... 568/862; 568/880,568/881: 568/882:568/883: 568/914: 502/257; 502/240; 502/254: 502/255 (Continued) (58) Field of Classification Search ................ 568/862, OTHER PUBLICATIONS 568/880, 881, 882, 883,914: 502/257, 240, 502/254, 255 The Heterogeneous Oxidation of Hydrogen Sulfide at Concentra See application file for complete search history. tions Below 1000 ppm in Nitrogen/Air Mixtures Over Supported Metal Oxide Catalysts; W.G. Cook & R.A. Ross, Atmospheric (56) References Cited Environonment, (1967-1989) 7(2), 145-151 (1973) Pergamon Press (1973). U.S. PATENT DOCUMENTS Effects of Small MoO3 Additions on the Properties of Nickel 2,434,110 A 1/1948 Hatch et al. ................ 260/602 Catalysts for the Steam Reforming of Hydrocarbons II. Ni-Mo/ 3,068.303 A 12, 1962 Pattison ...... ... 260/677 Al2O3 Catalysts in Reforming, Hydrogenolysis and Cracking of 3,098,882. A 7/1963 Arnold .... 260/677 n-butane, Applied Catalysis A. General 230 (2002) 85-97. 3,109,804 A 11, 1963 Martin ....... ... 208/89 3,205.281 A 9/1965 Fleming et al ... 260/683 (Continued) 3,260,759 A 7/1966 Skinner ...................... 260/635 Primary Examiner Elvis O. Price 3,296,325101.co. A 1/19671600 Gross .........................CE.". 260/677380 (74) Attorney, Agent, or Firm Richard B. Taylor 5,093,537.5,015,789 A 3/19925, 1991 ArntzUnruh etet al. al. .....568.862 568,862 (57) ABSTRACT 5,210,318 A 5/1993 Briggs et al. ... ... 568,496 RE34,349 E 8, 1993 Unruh et al. ... ... 568,862 5,256,827 A 10/1993 Slaugh et al. ... ... 568.454 The present invention provides a hydrogenation catalyst 5,334,778 A 8/1994 Haas et al. ................. 568,862 effective for hydrogenating 3-hydroxypropionaldehyde to 5,358,633. A 10/1994 Dai et al. ............... 208,216 R 1,3-propanediol. The hydrogenation catalyst comprises an 5,364.984 A 11/1994 Arntz et al. ................ 568,862 C.-alumina Support, nickel, ruthenium, and a promoter. The 5,389,595 A 2/1995 Simpson et al. ... SO2,315 nickel is deposited on the C-alumina Support, and the 5.449,653 A 9/1995 Briggs et al. ............... 502,166 ruthenium and the promoter are deposited on the nickel and 5,773,657. A 6/1998 Rutter et al. ................ 55 the C-alumina support. The C-alumina support comprises at 5,786,524 A 7, 1998 Powell et al. ............... 568,862 least 92 wt.% of the catalyst, and the nickel comprises from 5,888,380E. A 88.3, 1999 E.et al. t "1 - - - - 1,... R provides1 wt.% to a 6process wt.% ofof thehydrogenating catalyst. The 3-hydroxypropionalde present invention also 300. A 1000 MN, i.202s, hyde to 1,3-propanediol with the catalyst. 5,916,838 A 6/1999 Wulff-Doring et al. ..... 502,326 5,936,126 A 8, 1999 Ruhl et al. .................. 564,451 32 Claims, 8 Drawing Sheets US 7,335,800 B2 Page 2 FOREIGN PATENT DOCUMENTS JP 2004-182622 T 2004 WO 00,00456 1, 2000 EP O906258 4f1999 FR 219 1939 2, 1974 OTHER PUBLICATIONS GB 82.94.75 3, 1960 Oxidacion Deshidrogenate De Etilbenceno AEstrieno Sobre Oxidos GB 966270 8, 1964 De Molibdeno Y Niquel, H. Kum & J.L. Seane, Anales De Quimica, GB 101.1270 11, 1965 (1968-1979) 72(7-8), 703-708 (1976) (abstract). GB 1436458 5, 1976 Modification of 3-Hydroxypropanal Hydrogenation Catalyst, Z. Xu, GB 1581379 12, 1980 S. Guo, J. Xie, C. Gu, & P. Wang, Shiyou Huagong, (2005) 34(2), JP 83O49532 7/1979 132-135 (abstract). U.S. Patent Feb. 26, 2008 Sheet 2 of 8 US 7,335,800 B2 U.S. Patent US 7,335,800 B2 U.S. Patent Feb. 26, 2008 Sheet 4 of 8 US 7,335,800 B2 wae,-;), www.www. ********·,?……………. A ? % ? U.S. Patent Feb. 26, 2008 Sheet S of 8 US 7,335,800 B2 U.S. Patent Feb. 26, 2008 US 7,335,800 B2 No.gº------********?. U.S. Patent Feb. 26, 2008 Sheet 7 of 8 US 7,335,800 B2 U.S. Patent US 7,335,800 B2 US 7,335,800 B2 1. 2 HYDROGENATION CATALYST AND catalyst polluting the PDO product stream. Use of the HYDROGENATION METHOD supported ruthenium catalyst in a fixed-bed is preferred. Particularly preferred oxide phase supports are disclosed to CROSS-REFERENCE TO RELATED be oxide phases that are resistant to acidic media Such as APPLICATIONS titanium dioxide, silicon dioxide, aluminum silicate, Zirco nium dioxide, and Zeolites. Aluminum oxide and magne This application claims priority to U.S. Provisional Appli sium oxide are disclosed as having lower acid resistance. cation 60/673,530 filed on Apr. 21, 2005, herein incorpo rated by reference in its entirety. Supported, fixed-bed catalysts must have strong Support 10 materials in order to have a long catalyst life. Hydrogenation FIELD OF THE INVENTION in a fixed trickle bed configuration is favored by small catalyst particle size. Reduction of the particle size, how The present invention relates to a hydrogenation catalyst, ever, reduces the crush strength of the catalyst, which a process for preparing the hydrogenation catalyst, and a reduces the catalyst life. Catalysts having low crush strength process for hydrogenating aldehydes using the hydrogena 15 collapse more readily over time and eventually plug the tion catalyst. More particularly, the present invention relates catalyst bed, at which point the catalyst must be changed. to a hydrogenation catalyst, its method of preparation, and Support materials having high crush strength are gener its use in hydrogenating aldehydes, where the catalyst com ally those that have less porosity. Such as C-alumina. Sup prises an O-alumina Support having nickel deposited on the ports that are less porous, however, have less Surface to Support, and having ruthenium and a promoter deposited on Support the active catalyst metals, and, as a result, have less the nickel and the C-alumina Support, where the promoter is hydrogenation activity. selected from the group consisting of rhenium, tungsten, molybdenum, chromium, lanthanum, tin, iron, silver, cobalt, It is an object of the invention, therefore to provide a copper, or mixtures thereof. catalyst for the hydrogenation of HPA to PDO, wherein the 25 catalyst is a Supported catalyst that has relatively high crush BACKGROUND OF THE INVENTION strength, high activity over the life of the catalyst, long catalyst life, and that is economical and commercially attrac 1,3-propanediol (PDO) is a compound having multiple tive. uses. It is used as a monomer unit in the production of It is also an object of the present invention to provide a polyesters and polyurethanes that are useful as films and as 30 process for using such a catalyst to produce PDO from HPA fibers for carpets and textiles. It is also useful as an engine in a hydrogenation reaction, where the reaction converts a coolant. high rate of HPA to PDO at a high degree of selectivity, and, PDO may be prepared from ethylene oxide (EO) in a where the process is continuous, the volume/time yield of process involving two primary reactions. First, EO and PDO from HPA is high. synthesis gas (H/CO) are catalytically hydroformylated to 35 3-hydroxypropionaldehyde (HPA) in an organic solvent. The HPA is extracted from the solvent with water to form an SUMMARY OF THE INVENTION aqueous solution of HPA, and the aqueous solution of HPA is then hydrogenated to form PDO. In one aspect, the present invention provides a hydroge The hydrogenation of HPA to PDO is performed using a 40 nation catalyst effective for iron, cobalt, silver, copper or hydrogenation catalyst.
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