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(12) United States Patent (10) Patent No.: US 8.471,085 B2 Sydora (45) Date of Patent: Jun

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(12) United States Patent (10) Patent No.: US 8.471,085 B2 Sydora (45) Date of Patent: Jun US008471085B2 (12) United States Patent (10) Patent No.: US 8.471,085 B2 Sydora (45) Date of Patent: Jun. 25, 2013 (54) OLIGOMERIZATION CATALYST SYSTEM (56) References Cited AND PROCESS FOR OLGOMERIZING OLEFNS U.S. PATENT DOCUMENTS 2.935,495 A 5/1960 Kennedy (75) Inventor: Orson L. Sydora, Houston, TX (US) 3,100,764 A 8, 1963 Jezlet al. 3,231,550 A 1/1966 Manyik et al. (73) Assignee: YoshiyiphysicompanyO O 3,300,4583,242,099 A 3/19661/1967 Manyik et al. , The Woodlands, TX (US) 3,347,840 A 10/1967 Manyik et al. - 3,534,006 A 10/1970 Kamaishi et al. (*) Notice: Subject to any disclaimer, the term of this 3,558,676 A 1/1971 Doherty et al. patent is extended or adjusted under 35 3,635,869 A 1/1972 Steele et al. U.S.C. 154(b) by 281 days. 3,819,746 A 6, 1974 Katzakian, Jr. et al. (Continued) (21) Appl. No.: 12/771,122 FOREIGN PATENT DOCUMENTS (22) Filed: Apr. 30, 2010 CA 2087578 T 1994 CN 12.56968 6, 2000 (65) Prior Publication Data (Continued) US 2010/O274O65A1 Oct. 28, 2010 OTHER PUBLICATIONS International Application PCT/2001/033431 Search Report dated Related U.S. ApplicationO O Data Jun. 22, 2011. (63) Continuation-in-part of application No. 12/609,272, (Continued) filed on Oct. 30, 2009. Primary Examiner — Yun Qian (60) Provisional application No. 61/110,396, filed on Oct. (74) Attorney, Agent, or Firm — Merchant & Gould P.C. 31, 2008, provisional application No. 61/110,407, (57) ABSTRACT filed on Oct. 31, 2008, provisional application No. 61/110,476, filed on Oct. 31, 2008. Among other things, this disclosure provides an olefin oligo merization system and process, the system comprising: a) a (51) Int. Cl. transition metal compound; b) a pyrrole compound having a CD7C2/24 (2006.01) hydrogenatom on at the 5-position or the 2- and 5-position of C07C2/02 (2006.01) apyrrole compound and having a bulky Substituent located on BOI 3/14 (2006.01) each carbon atom, adjacent to the carbon atom bearing a (52) U.S. Cl. hydrogen atom at the 5-position or the 2- and 5-position of a USPC ........... ssss 13.502/102, so2/103.502/256: pyrrole compound. These catalyst system have significantly 5O2/167: 502/123585/604 improved productivities, selectivities to 1-hexene, and pro (58)58) tField OSSOof Classification SeaS h s s lystvides Systems higher purityusing 2,4-dimethyl1-hexene within pyrrole. the C fraction than cata See application file for complete search history. 28 Claims, 2 Drawing Sheets 120,000 --2,5-DMP -o-2,5-DBP --2,4-DMP -e-pyrrole sar 2,5-DEP a -2-M-A-LPP 100,000 80,000 60,000 40,000 20,000 40 60 80 OO 20 40 18O Oligomerization Temperature (°C) US 8,471,085 B2 Page 2 U.S. PATENT DOCUMENTS 2002/0182124 A1 12/2002 Woodard et al. 2004/0236163 A1 11/2004 Ewert et al. 3,838,101 9, 1974 Steele et al. 2005/0187391 A1 8/2005 Knudsen et al. 3,873,602 3, 1975 Katzakian, Jr. et al. 2005/O197521 A1 9, 2005 Kreischer 3,932.285 1, 1976 Ceprini et al. 2005/0222350 A1 10/2005 Small et al. 3,962, 182 6, 1976 Steele et al. 2005/0255987 A1 11/2005 McDaniel et al. 3,968, 135 7, 1976 Steele et al. 2006, O247483 A1 11/2006 McConville et al. 3,977,996 8, 1976 Katzakian, Jr. et al. 2007,0185361 A1 8/2007 Buchanan et al. 3,978,026 8, 1976 Katzakian, Jr. et al. 2007,0185.364 A1 8/2007 Buchanan et al. 4.017.429 4, 1977 Steele et al. 2008/0051545 A1 2/2008 McDaniel et al. 4,224, 181 9, 1980 Langer, Jr. 2008/0058534 A1 3/2008 Knudsen et al. 4,603, 184 T. 1986 Sato et al. 2008/O177122 A1 7/2008 Knudsen et al. 4,668,808 5, 1987 Smith 2008/0293899 A1 11/2008 McConville et al. 4,668,838 5, 1987 Briggs 2010.0030000 A1 2/2010 Emoto et al. 4,716,206 12, 1987 Fujita et al. 2010.0113852 A1 5/2010 Sydora 4,721,762 1, 1988 Commereuc et al. 2010.0137669 A1* 6/2010 Han et al. ...................... 585,514 4,806,513 2, 1989 McDaniel et al. 4,814,308 3, 1989 Konrad et al. FOREIGN PATENT DOCUMENTS 5, 198,563 3, 1993 Reagen et al. 5,288,823 2, 1994 Reagan et al. EP O194596 A2 9, 1986 5,331,070 T. 1994 Pettijohn et al. EP 0207220 A2 1, 1987 5,331, 104 T. 1994 Reagen et al. EP O416304 A2 3, 1991 5,340,785 8, 1994 Reagen et al. EP O608447 A1 8, 1994 5,360,879 11, 1994 Reagen et al. EP O78O353 A1 6, 1997 5,376,612 12, 1994 Reagen et al. EP 0608447 B1 10, 2001 5,382,738 1, 1995 Reagen et al. FR 2253029 6, 1975 5,393,719 2, 1995 Pettijohn et al. WO WO97,11082 3, 1997 5,399,539 3, 1995 Reagen et al. WO WO 2006,109 194 A2 10, 2006 5.438,027 8, 1995 Reagen et al. WO WO, 2008/088178 * 7/2008 5,451,645 9, 1995 Reagen et al. OTHER PUBLICATIONS 5,470,926 11, 1995 Reagen et al. 5,523,507 6, 1996 Reagen et al. Briggs, J., Chem. Commun., Selective Trimerization of Ethylene to 5,543,375 8, 1996 Lashier et al. 5,563,312 10, 1996 Knudsen et al. Hex-1-ene, J. Chem. Soc., 1989, pp. 674-675. 5,689,028 11, 1997 Lashier et al. Hart, Robert et al., “Synthesis and Structures of Metal Carboxylate 5,763,723 6, 1998 Reagen et al. Liquids.” Shepherd Chemical Company, Mar. 23, 2009, National 5,786,431 7, 1998 Reagen et al. Meeting of the American Chemical Society. 5,814,575 9, 1998 Reagen et al. Mehrotra, R.C. et al., “Metal Carboxylates.” Jaipur 302004, 1983, 5,856.257 1, 1999 Freeman et al. Academic Press, pp. 22-27. 5,856,612 1, 1999 Araki et al. Mehrotra, R.C. et al., “Metal Carboxylates.” Jaipur 302004, 1983, 5,859,303 1, 1999 Lashier Academic Press, pp. 233-317. 5,910,619 6, 1999 Urata et al. Tille, D., Z. Anorg. Alleg. Chem. Organometal Compounds of Nitro 5,919,996 7, 1999 Freeman et al. gen Systems, 1971, 384, pp. 136-146. 5,986,153 11, 1999 Kallenbach Tille, D., Zeitschrift fur Naturforschung, Pyrrolylchromium Com 6,043,401 3, 2000 Bagheri et al. 6,133,495 10, 2000 Urata et al. pounds, 1966, 21b, p. 1239. 6, 191,076 2, 2001 Gee International Search Report and Written Opinion for PCT/US2009/ 6,380.451 4, 2002 Kreischer et al. 062700, Jan. 28, 2010. 6,455,648 9, 2002 Freeman et al. U.S. Appl. No. 61/110,396, filed Oct. 31, 2008, entitled “System and 6,521,806 2, 2003 Tamura et al. Method for Diluting Metal Precursors for Oligomerization Catalyst 7,045,632 5, 2006 Small Systems”. 7,129,304 10, 2006 Small et al. U.S. Appl. No. 61/110,407, filed Oct. 31, 2008, entitled “System and 7,157,612 1/2007 Ewert et al. Method for Deactivating and Quenching an Oligomerization Cata 7,259,284 8, 2007 Hope et al. lyst”. 7,268,096 9, 2007 Small et al. U.S. Appl. No. 61/110,476, filed Oct. 31, 2008, entitled 7,271,121 9, 2007 Small et al. “Oligomerization Catalyst System and Process for Oligomerizing 7,297,832 11/2007 Blann et al. ................... 58.5/527 Olefins. 7,309,805 12, 2007 Hope et al. 7,351,780 4, 2008 Hope et al. International Preliminary Report on Patentability for PCT/US2009/ 7,378,537 5/2008 Small et al. 062700 mailed May 12, 2011, The International Bureau of WIPO, 7 7,384,886 6, 2008 Knudsen et al. pageS. 7,396,970 T/2008 Battiste U.S. Official Action dated Jun. 20, 2012 in U.S. Appl. No. 7,425,661 9, 2008 McConville et al. 12/609,272, 17 pages. 7,456,284 11, 2008 Small 7,476,775 B2 1/2009 Kreischer * cited by examiner U.S. Patent US 8471,085 B2 U.S. Patent Jun. 25, 2013 Sheet 2 of 2 US 8471,085 B2 ( US 8,471,085 B2 1. 2 OLGOMERIZATION CATALYST SYSTEM In one aspect, this disclosure provides for a catalyst system AND PROCESS FOR OLGOMERIZING comprising: a) a transition metal compound; b) a pyrrole OLEFNS compound having i) a hydrogen atom located on at least one pyrrole ring carbonatom adjacent to the nitrogen atom of the CROSS REFERENCE TO RELATED pyrrole ring, and ii) a bulky Cs to Cs organyl group or a bulky APPLICATIONS C. to Co. silyl group located on a pyrrole ring carbon atom adjacent to any pyrrole ring carbon atom bearing the hydro This application is a Continuation-In-Part application to gen atom adjacent to the nitrogen atom of the pyrrole ring; U.S. patent application Ser. No. 12/609,272 filed Oct. 30, and c) a metal alkyl. In an embodiment, the bulky substituent 2009 which in turn claims priority to and the benefit of U.S. 10 located on pyrrole ring carbon atom adjacent to any pyrrole Provisional Patent Application No. 61/110,396 filed Oct. 31, ring carbon atom bearing the hydrogen atom adjacent to the 2008, U.S. Provisional Patent Application No.
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