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Nited 'States Patent Of?Ce 3,511,891 nited ‘States Patent Of?ce Patented May 12, 1970 1 2 3,511,891 Also included are compounds of the general formula: OLIGOMERISATIO'N PROCESS Keith Andrew Taylor and John Alex Leonard, Runcorn, Rm—Y—R"—Y—Rm England, assignors to Imperial Chemical Industries where m=l or 2, Y and R have the same signi?cance, Limited, Millbank, London, England, a corporation of and R” is a direct linkage or a divalent radical, for ex Great Britain ample —CH2——, -—(CH2)D—~. When two Y atoms are No Drawing. Filed May 19, 1967, Ser. No. 639,659 present in the ligand or two or more ligands of the type Claims priority, application Great Britain, Dec. 21, 1966, YRn are used the Y atoms may be the same or different. 57,122/66, Patent 1,131,146 Int. Cl. C07c 3/10, 11/02 The donor atom or atoms of Group V-B may be in US. Cl. 260—683.15 4 Claims 10 corporated in an aromatic ring. Especially useful ligands are organic or halogen substituted phosphines or phos phites. ABSTRACT OF THE DISCLOSURE Examples of suitable ligands are: A process for the oligomerisation of monoalkenes in which the monomer is contacted in the liquid phase with 15 a homogeneous catalyst formed from a Group VIII metal compound, a ligand containing a donor atom of Group VB and a Lewis acid compound. The components of the catalyst may be added to the reaction mixture singly or 20 as one or more pre-formed complexes. For example, pro- pene and butene are co-dimerised using a bistrialkyl phosphine nickel halide complex/ ethyl aluminium dichlo ride mixture as catalyst. The catalyst may be stabilized by contacting with an ole?n. Catalysts of reduced iso butylene polymerization activity are obtained by using an 25 Al/Ni atomic ratio of 3/1 to 5/1 and conditioning with an isobutene-free monoalkene. This invention relates to a process for the oligomerisa tion of monoalkenes and, in particular to the dimerisation and co-dimerisation of such alkenes. r l According to the present invention a process for the oligomerisation of monoalkenes comprises contacting the 35 where : monomer with a catalyst formed from a compound of a ¢=phenyl metal of Group VIII of the Periodic Table, a ligand con Me=methyl taining a donor atom or atoms of Group V-B of the Et=ethyl Periodic Table and a compound capable of acting as a Bu=n-butyl Lewis acid under the conditions of the process. 40 Preferred Lewis acid compounds are organo aluminium Cyzcyclohexyl compounds such as the chlorides, bromides and alkyl In one form of our invention, the Group VIII metal. chlorides o-r ‘bromides of aluminium; but boron, alumin compound and ligand containing a Goup V~B donor ium, gallium, indium, titanium, zirconium and iron ha atom are chosen so that they form a complex species con lides or organo halides may also be used. 45 taining a metal of Group VIII of the Periodic Table of By the Periodic Table we mean the Long Periodic the Elements in which at least one of the coordination Table, as shown inside the back cover of “General and sites of the metal is occupied by a ligand containing a Inorganic Chemistry” by Partington, published by Mc donor atom or atoms of Group V~B of the Periodic Table Millan, 2nd Edition. of the Elements linked directly to the metal, and at least Preferably, the Group VIII metal compound is one in one other of the said sites is occupied by an anionic lig which the metal is combined with an anionic ligand. and. Suitable compounds include salts of organic acids, such Within the term “complex species containing a metal of as naphthenic or stearic acids or co-ordination com Group VIII” we mean to include any species in which pounds, such as metal acetylacetonates; but salts of in such a metal atom is co-ordinated to at least one of each organic acids may also be used, particularly in anhydrous 55 of the ligands previously mentioned plus such other lig form. and or ligands as are necessary to satisfy the appropriate By the term “ligand containing a donor atom or atoms co-ordination number of the metal. The said other ligands of Group V-B” we mean a compound the whole or part may be anionic, cationic or neutral and may be mono- or of which is capable of bonding to a metal atom. A pre poly-dentate. Thus the species may be neutral, positively ferred Group V-B donor atom is phosphorus. 60 or negatively charged, in toto, so that it may take the Each ligand containing a donor atom or atoms of form of a complex compound as such or, alternatively, it Group V-B may be mono- or poly-dentate. Suitable lig may exist as a complex cation or anion, in which case it ands include compounds of the general formula: YR“, will be associated with one or more other anions or ca n=2 or 3, Y is a donor atom of Group V-B the sub tions. Suitable Group VIII metals include nickel and co stituents R, which may be the same or different, are hy balt. Nickel is a particularly effective metal. drogen atoms or monovalent radicals, such as hydrocar The speci?ed anionic ligand or ligands may be, for byl radical for example alkyl, alkenyl, aryl, alkaryl, aral example, Cl—, Br“, I-, SCN-, Nof, naphthenate, kyl and cycloalkyl, or a substituted derivative thereof. R stearate, acetylacetonate and when more than one is pres may also be halogen, pseudo-halogen, —OR', —SR', ent they may be the same or different. or —NR'2 where R’ is a substituted or unsubstituted hy When the Group VIII ‘metal compound and donor drocarbyl radical. When both R and R’ are hydrocarbyl atom ligand are chosen as above, the complex formed radicals, they may be the same or different. may be isolated (hereinafter referred to as a preformed 3,511,891 4 Group VIII metal complex). Thus, it may be convenient be mixed and treated with a gaseous or liquid ole?n to use the catalyst as a two-component mixture, i.e. pre before or simultaneously with the addition of the Lewis formed Group VIII metal complex/Lewis acid mixture. acid compound. Group VIII metal complexes which may be used in (2) A gaseous ole?n, for example ethylene or propene, this way, may be prepared by well-established published may be bubbled through a solution of a Group VIII metal procedures, for examples, see Jensen, et al, Acta Chemica complex before addition of the Lewis acid compound. Scandinavica, 17, 1963, 1115-1125. Examples of such (3) The Group VIII metal complex may be dissolved complexes include: in a liquid ole?n, for example liquid n-butene, or re cycled heavy ends from subsequent dimer recovery stages, 10 and the Lewies acid compound added to the resulting solution. (4) The Group VIII metal complex or Group VIII metal compound and donor atom ligand may be dis solved in a non-ole?nic solvent, e.g. chlorobenzene, and a 15 liquid ole?n and a Lewis acid compound added simul taneously. ‘Once a stabilised catalyst mixture has been prepared by the aforementioned stabilising process, it appears to be stable for at least several hours, as indicated by the ab 20 sence of discolouration or precipitation from the solution. As previously mentioned, the catalyst mixture may also Whereas it is convenient to use the appropriate stoichio be stabilised by keeping it below 0° C. We have also metric proportions of nickel compound and donor atom found that with certain mixtures, for example, nickel his ligand when preparing the de?ned Group VIII metal com trialkylphosphine dihalide/ aluminium alkyl halide, a single plexes, it is within our invention to use non-stoichiometric 25 complex may be isolated on cooling the solution to —-78° proportions of these two components of our catalyst sys C. These complexes have been shown to contain the two tem. It has been found that ratios of donor atom ligand: components of the mixture in de?nite proportions which Group VIII metal in the range 0.2:1 to 20:1 may be may be expressed as an aluminium/nickel ratio. In the used (expressed in g. atoms of ligand and metal) espe case of a (Bu3P)2NiCl2/EtAlCl2 mixture, a blue complex cially when isolation of the Group VIII metal complex having an aluminium/nickel ratio of 3/1 may be isolated. is not envisaged. This complex may be conveniently stored at temperatures Although the components of our catalyst (i.e. Group between -—20° C. and =80° C. until required. When such VIII metal compound/donor atom ligand/Lewis acid or a complex is added to a suitable liquid monomer or mono Group VIII metal complex/Lewis acid) may be added mer solution and the solution allowed to warm to ambient to the oligomerisation reaction mixture in any order, if temperature, the blue complex turns yellow and then acts they are mixed before being brought into contact with as an oligomerisation catalyst. This method of catalyst the monomer, there may ‘be some reduction of activity preparation allows close control of the ratio of aluminium of the catalyst which, under particularly adverse condi to nickel which may be extremely desirable under certain tions, may be accompanied by deposition of the ‘Group conditions, as discussed later. VIII metal. Monoalkenes which may be oligomerised by the process This loss of activity of the mixture is accelerated by of our invention include ethylene, propene, but-l-ene and rise of temperature of the mixture and also by undue but-Z-ene (cis and trans), or mixtures of the same.
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