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(12) United States Patent (10) Patent No.: US 6,852,843 B2 Cavell Et Al

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(12) United States Patent (10) Patent No.: US 6,852,843 B2 Cavell Et Al USOO6852843B2 (12) United States Patent (10) Patent No.: US 6,852,843 B2 Cavell et al. (45) Date of Patent: Feb. 8, 2005 (54) PHOSPHORUS SUPPORTED CARBENE 6,313,331 B1 11/2001 Cavell et al. ................. 556/18 TRANSTION METAL COMPLEXES 6,476,245 B1 11/2002 Cavell et al. .................. 556/9 6,538,115 B2 * 3/2003 Cavell et al. ................. 534/15 (75) Inventors: Ronald G. Cavell, Edmonton (CA); FOREIGN PATENT DOCUMENTS Ruppa P. Kamalesh Babu, Edmonton (CA); Aparna Kasani, Edmonton (CA) WO WO 96/23010 8/1996 (73) Assignee: The Governors of the University of OTHER PUBLICATIONS Alberta (CA) U. Zucchini, E. Albizzati and U. Giannini, Synthesis and Properties of Some Titanium and Zirconium Benzyl Deriva (*) Notice: Subject to any disclaimer, the term of this tives, J. Organometal Chem., 26 (1971) 357-372. patent is extended or adjusted under 35 Von R. Appel und I. Ruppert, Darstellung silyierter Alky U.S.C. 154(b) by 0 days. len-bisiminophosphorane und ihre Cyclisierung mit Phos phor (V)-fluoriden, Zanor. allg. Chem. 406, 131-144 (21) Appl. No.: 10/356.884 (1974). Richard A. Andersen, Chloro- and Methyltris(hexamethyl (22) Filed: Feb. 3, 2003 disilyl) amidozirconium(IV) and -hafnium(IV), 1979 (65) Prior Publication Data American Chemical Society, Inorganic Chemistry, Vol. 18, No. 6, 1979, 1724-1725. US 2003/0158394A1 Aug. 21, 2003 Michael D. FryZuk, David H. McConville & Steven J. Rettig, Synthesis, structure and hydrogenation of n-benzyl Related U.S. Application Data diphosphine complexes of rhodium and iridium, J. or Organ (60) Division of application No. 09/770,979, filed on Jan. 26, mettalic Chemistry, 445 (1993) 245–256. 2001, now Pat. No. 6,538,115, which is a continuation of George J.P. Britovsek, Vernon G. Gibson, Brian S. Kimber application No. 09/375,943, filed on Aug. 17, 1999, now ley, Peter J. Maddox, Stuart J. McTavish, Gregory A. Solan, abandoned, which is a continuation-in-part of application Andrew J.P. White and David J. Williams, Novel Olefin No. 09/174,782, filed on Oct. 19, 1998, now abandoned. polymerization catalysts based on iron and cobalt, Chem. Commun., 1998, p. 849. (51) Int. Cl."................................................... C07F 5/00 (52) U.S. Cl. ... ... 534/15; 568/8; 568/12 * cited by examiner (58) Field of Search ................................ 534/15; 568/8, 568/9, 12, 16, 17; 556/9, 12, 13, 18, 19, Primary Examiner Dameron L. Jones 400 (74) Attorney, Agent, or Firm-Kenneth H. Johnson (57) ABSTRACT (56) References Cited The present invention relates to novel complexes of U.S. PATENT DOCUMENTS (transition) metals containing ligands having phosphorus 5,502,128 A 3/1996 Flores et al. centerS Supporting a carbene atom or heteroalkane radical 5,557,023 A 9/1996. Somogyvariet al. bonded to the (transition) metal. 5,707,913 A 1/1998 Schlund et al. 6,060,568 A * 5/2000 Cavell et al. ............... 526/1.31 35 Claims, No Drawings US 6,852,843 B2 1 2 PHOSPHORUS SUPPORTED CARBENE SUMMARY OF THE INVENTION TRANSTION METAL COMPLEXES The present invention provides a complex having the This is a division of application Ser. No. 09/770,979, formula: filed Jan. 26, 2001, now U.S. Pat. No. 6,538,115, which is 1. R5 a continuation of application Ser. No. 09/375,943, filed Aug. RN o / 17, 1999, now abandoned, which is a continuation-in-part of R -—N application Ser. No. 09/174,782, filed Oct. 19, 1998, now =M1-R abandoned. R3-PEN| Sir FIELD OF THE INVENTION Yss The present invention relates to novel complexes of R4 metals preferably transition metal and to processes for producing Such complexes. The complexes contain at least wherein M is a metal atom; R', R, R and R' are indepen one phosphorus center, and a carbon atom or an alkyl radical 15 dently Selected from the group consisting of a hydrogen bonded to the metal to form a carbene or metal heteroatom atom, a Saturated or unsaturated Straight chained, branched alkenyl bond. or cyclic hydrocarbyl radical which is unsubstituted or substituted by one or more substituents selected from the group consisting of a halogen atom and a C-6, most BACKGROUND OF THE INVENTION preferably a C- alkyl radical; R and Rare independently Currently there is increasing interest in complexes of Selected from the group consisting of a hydrogen atom, a transition metals having a novel Structure. Potentially Such halogen atom, an amide -NR'R'', imide =NR', alkoxide compounds could have significant use in a number of or aryl oxide group -OR', and an-OSi(R) group where applications Such as chemical processing, herbicides, pesti R" and R are defined above, and a saturated or unsaturated cides and possibly medical fields. 25 Straight chained, branched or cyclic hydrocarbyl radical Recently there has been Significant interest in the catalyst which are unsubstituted or Substituted by a halogen atom or of Brookhart et all which may activate later transition metals a C alkyl radical or a Lewis base (neutral coordinating in a polymerization process. Such complexes are disclosed, ligands) which may contain a donor heteroatom including for example, in World patent application 96/23010 jointly in but not limited to ethers, tertiary amines, tertiary phosphines the names of The University of Carolina at Chapel Hill and and cyclic amines; and each R is independently selected E.I. DuPont published Aug. 1, 1996. The Brookhart et al from the group consisting of radicals Selected from the patent application does not teach the complexes of the group consisting of Saturated and unsaturated Straight present invention. chained, branched and cyclic hydrocarbyl radicals, prefer ably Cls Saturated or unsaturated Straight chained, The recent paper (Chem. Comm (1998) p. 849) by the 35 branched or cyclic hydrocarbyl radicals most preferably Cs coworkers of Gibson at Imperial College UK (and BP) teach Straight or branched alkyl radicals and C2 cyclic aliphatic complexes having a novel Structure that is dissimilar to the or aromatic radical; radicals of the formula Si(R) wherein complexes of the present invention. It is postulated the each R is independently selected from the group consisting complexes of Gibson will have utility in the polymerization of Saturated or unsaturated Straight chained, branched or of certain monomerS Such as alpha olefins. 40 cyclic hydrocarbyl radicals, preferably Co Saturated or There has been a great deal of work recently by both unsaturated Straight chained, branched or cyclic hydrocarbyl Exxon in the field of metallocene chemistry and by the Dow radicals; and radicals of the formula III: Chemical Company in Single Site constrained geometry complexes. AS far as applicant has been able to determine R9 R10 none of the chemistry proposed by either Exxon or Dow 45 contain a carbene atom or a constrained alkyl carbon bonded to a transition metal. There are Several patents relating to amidinato complexes of transition metals which are Suitable for the polymeriza tion of various olefins. U.S. Pat. No. 5,502,128 issued Mar. 50 R11 R12 26, 1996, assigned to the University of Massachusetts, wherein R, R', R'' and R'' are independently selected teaches Such complexes may be used to polymerize vinyl from the group consisting of a hydrogen atom, a fluorine aromatic monomers; and U.S. Pat. No. 5,707,913 issued Jan. atom, a NO2 radical, a C- alkyl radical, and a Cs-12 aryl 13, 1998, assigned to BASF, teaches such compounds may 55 radical and E is an endocyclic nitrogen atom or a C-CN be used polymerize olefins. Neither of these patents disclose grOup. complexes of the Structure of the present invention. The present invention provides a complex dilithium Salt U.S. Pat. No. 5,557,023 issued September, 1996, teaches of the formula II: the use of Some complexes of transition metals to oligomer ize lower alpha olefins Such as ethylene to higher olefins 60 R1 R2 R3 R4 Such as hexene and the like. The complexes of the patent do not contain a carbene atom or Substituted carbon bonded to Nl1. crisy/ the transition metal. Applicant has been unable to identify any prior art dis R -N Nin R5 closing the complexes of the present invention. In short the 65 complexes of the present invention represent a novel chem wherein R', R, R and R" are independently selected from istry having potential applications in many fields. the group consisting of a hydrogen atom, a Saturated or US 6,852,843 B2 3 4 unsaturated Straight chained, branched or cyclic hydrocarbyl and n are as defined above, X and Y are independently radical which is unsubstituted or substituted by one or more Selected from a group consisting of an alkyl, preferably Substituents Selected from the group consisting of a halogen having from 1 to 10 carbon atoms which is unsubstituted or atom and a C, most preferably a C alkyl radical; and Substituted by a C- alkyl radical or a Co aryl (e.g. each R is independently selected from the group consisting benzyl) radical, a silylated amido or imido complex-N(Si of radicals Selected from the group consisting of a Saturated (R)) or =NCSi(R) where R is defined above, or imido or unsaturated Straight chained, branched or cyclic hydro =NR radicals where R is a Co alkyl or a Co aryl carbyl radicals preferably C. Saturated or unsaturated radical, a halogen atom, an alkoxy radical preferably having Straight chained, branched or cyclic hydrocarbyl radicals, most preferably Cs straight or branched alkyl radicals and from 1 to 10 carbon atoms and aryloxy radical preferably C-2 cyclic aliphatic or aromatic radicals, radicals of the having from 6 to 10 carbon atoms, and the Sum of S and t formula Si(R) wherein each R is independently selected equal the valence of the transition metal M and provided that from tho group consisting of Saturated or unsaturated at least two of the X and Y groups can be eliminated from Straight chained, branched or cyclic hydrocarbyl radicals, the molecule, in a Cs2 hydrocarbyl Solvent or a Coether preferably Co Saturated or unsaturated Straight chained, solvent at a temperature from 20° C.
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