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United States Patent Office Patented Mar 3,567,701 United States Patent Office Patented Mar. 2, 1971 2 3,567,701 be obtained in industry, such as lower aluminium alkyls, PROCESS FOR PREPARNG POLYOLEFENS for example aluminium triisobutyl, and acetylene can be Karl Diether Keil, Frankfurt am Main, Germany, assignor used, without an expensive elimination of the catalyst, for to Farbwerke Hoechst Aktiengesellschaft vormals preparing polyolefins having a narrow molecular weight Meister Lucius & Bruning, Frankfurt am Main, Ger range suitable for further processing the polyolefins. many As aluminium-organic compounds which are prepared No Drawing. Filed May 1, 1968, Ser. No. 725,912 in known manner, there are suitable, for example, reac Claims priority, application Germany, May 20, 1967, tion products of acetylene compounds, such as acetylene, F 52,468 with dialkyl-aluminium hydrides, for example diisobutyl Int, C. C08f 1/42, 3/06 aluminium hydride, as well as with aluminium trialkyls, U.S. C. 260-88.2 1. Claim O for example aluminium triisobutyl. Preferably suitable for the process of the invention are ABSTRACT OF THE DISCLOSURE the dialkyl-aluminium alkenyls which can be prepared with acetylene and which correspond to the formula The present invention relates to a process for the polym 5 R2Al-CH=CH-R in which R represents hydrocarbon erization of ethylene or mixtures of ethylene with up radicals having from 2 to 10 carbon atoms. to 10% by weight of higher o-olefins in the presence of Reaction products which can be prepared from these a mixed catalyst composed of a trivalent chlorine-contain reaction products of acetylene by a thermal treatment ing titanium compound and an aluminium-organic com" at temperatures in the range of from 60 to 200° C., pref ponent obtained by reacting acetylenes with aluminum 20 erably from 140 to 180° C., are especially effective. A hydrocarbons. number of addition-, rearrangement- and re-splitting steps --two-starre-- of an exothermic reaction yield, for example, polymeric aluminium organyls which, according to the process of The present invention provides a process for polymeriz the invention, have a particular activating effect. This ing ethylene and mixtures of ethylene with higher ox-ole 25 effect consists in obtaining a polymer which has the low fins. est possible molecular weight and a reduced specific vis When the polymerization of olefins by the low pressure cosity in the range of from about 1.3 to 2.5 and which is process is carried out in the presence of catalysts con suitable for injection molding, with a high catalyst yield sisting of a small amount of a titanium compound and an and the lowest possible hydrogen feed during the polym excess of a chlorine-free aluminium-organic compound, 30 erization of the olefins. and hydrogen as a molecular weight controlling agent, the The special suitability of the aluminium compounds polymerization rate of the olefin decisively depends on the claimed can be seen from Table 1: The homopolymeriza type of the aluminium organyl. tion of ethylene was carried out under strictly comparable The use of polymeric aluminium-organic compounds as test conditions so that the molecular weights can be cal catalyst components is generally expensive since, in many 35 culated from the i5-values. While aluminium trialkyls hav cases, these compounds are not easily obtainable. Belgian ing relatively small alkyl groups, such as aluminium tri Pat. No. 601,855 discloses the preparation of aluminium isobutyl (a), yield a polymer having a high molecular isoprenyl. weight, the molecular weight considerably decreases un From German Pats. Nos. 1,052,987 and 1,044,082 as der constant polymerization conditions when diisobutyl well as from Liebigs Annalen, vol. 629, page 222 (1960) 40 aluminium isohexenyl (b) and its reaction products (c) it is known that addition products can be prepared from resulting from the thermal treatment, are used. When saturated aluminium hydrocarbons and acetylene or acet higher aluminium alkyls are used as starting products, the ylene derivatives and the corresponding unsaturated com aforesaid effect is somewhat less pronounced since higher pounds may be reacted or subjected to a thermal treat aluminium trialkyls, such as aluminium tridecyl (g), al ment with further aluminium hydrocarbons to yield vis ready provide a polymer having a relatively low molecu cous aluminium compounds from dialkyl-aluminium alke lar weight, in a comparable catalyst yield. nyls in a number of polyadditions or re-splitting reactions Furthermore suitable as aluminium-organic activators and rearrangements. are the reaction products of dialkyl-aluminium alkenyls I have now found that aluminium compounds of this with aluminium trialkyls or dialkyl-aluminium hydrides. type in combination with chlorine-containing titanium The dialkyl-aluminium alkinyls which can be prepared compounds are excellently suitable for the polymerization from dialkyl-aluminium halides and light metal acetylides of ethylene and the mixtures thereof with up to 10% by in inert hydrocarbons and which correspond to the formu weight of higher a-olefins in solution, suspension or in la R2Al-C=C-R' in which R and R' each represents the gaseous phase at temperatures in the range of from a hydrocarbon radical having from 1 to 10, preferably 20° to 250° C., preferably from 60° to 130° C., under from 3 to 6, carbon atoms, as well as the reaction products a pressure of from 0 to 10 atmospheres gage, preferably 5 5 thereof with aluminium trialkyls or dialkyl-aluminium hy from 2 to 6 atmospheres gage, in the presence of a mixed drides are also suitable activators. catalyst consisting of a trivalent chlorine-containing ti The aluminium compounds that do not come within this tanium compound in a concentration of from 0.03 to invention, are prepared either in substance or rather in 0.5 millimol per liter of dispersing agent or per 0.5 liter dilution with inert dispersing agents. Small amounts of of reactor volume and an aluminium-organic component 60 cuprene which have formed are filtered off prior to the in a concentration of from 0.01 to 3 millimols of alumini use as polymerization catalyst. A slight color of the crude um per liter of dispersing agent or reactor volume, while metallo-organic compounds, which may be present in controlling the medium molecular weight by hydrogen, Some cases, especially in the compounds of the polymeric which polymerization process comprises carrying out the type, can be neglected since the proportions of the alu polymerization in the presence of a mixed catalyst, the 65 minium components used with regard to the amount of albiminium-organic component of which has been pre polymer obtained, are small and, moreover, they do not pared by reacting acetylene or acetylene derivatives with remain entirely in the polymer in the case of a solution aluminium hydrocarbons whose organy radicals contain or suspension polymerization. from 1 to 10, preferably 3 to 6, carbon atoms. For the polymerization of ethylene or mixtures of The technical advance of the process of the invention 70 ethylene with up to 10% by weight of higher ox-olefins, resides in the fact that components that can very easily preferably propylene or butene-1, the aluminium com 3,567,701 3 4. pounds are used in amounts in the range of from 0.01 to 9 hours at 35° C. by gently cooling, whereupon 25 grams 3 millimols of aluminium per liter of dispersing agent or of acetylene were absorbed (conversion rate 96%). A per liter of reactor volume, depending on the purity of light yellow solution was filtered off from the slight amount the dispersing agent or solvent and of the olefins to be of cuprene that had formed; prior to the use as a polym reacted. The higher the content of minor impurities, for erization activator, unreacted acetylene which was still example water, oxygen or CO2, the larger the amount of 5 dissolved in the solution was eliminated by passing nitro aluminium compound required which, however, does in gen through it. For subjecting it to a thermal treatment, no case exceed an amount that leads to an ash content of the diisobutyl-aluminium isohexenyl solution was heated more than 300 p.p.m. If necessary, the olefins and the dis under reflux to 150° C. for 2 hours. 60 grams of a dis persing agent or solvent have to be purified by known O tillate (predominantly consisting of isobutylene) escaped methods. As dispersing agents and solvents the inert hy over the intensely cooling reflux condenser and were con drocarbons commonly used for Ziegler-polymerizations densed in a cooling trap at a temperature of -78 C. are employed. The titanium compounds used are trivalent chlorine-con EXAMPLE 2 taining titanium compounds, such as titanium chloride or 5 Preparation of the titanium catalyst titanium alkoxy-chloride, which are prepared by a re (a) With the use of heated diisobutyl-aluminium iso duction of titanium tetrachloride or chloro-alkoxy-titanate hexenyl: 333 milliliters of a 25%-by-weight solution of the formula Ti(OR)4-Cl in which n is an integer of (0.333 mol) of diisobutyl-aluminium isohexenyl (Exam from 1 to 4 and R represents hydrocarbon radicals having ple 1) heated to 150° C. were added dropwise, while from 2 to 8 carbon atoms, by means of aluminium-organic 20 stirring and cooling, within an hour at 0° C. to a solu compounds, for example alkyl-aluminium Sesquichloride, tion of 110 milliliters (1 mol) of titanium tetrachloride dialkyl-aluminium monochloride, aluminium trialkyls or in 250 milliliters of a diesel oil fraction boiling from 150 aluminium polymers, for example aluminium isoprenyl. to 160 C. Stirring was continued for another 2 hours at Especially suitable for the reduction of the tetravalent 0 C.
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