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United States Patent Office Patented Nov 2,859,228 United States Patent Office Patented Nov. 4, 1958 2 plished by reacting a lead halide wherein the halide has an atomic weight greater than 35, that is the chlorides, 2,859,228 bromides, and iodides of lead, and mixed lead halides, with an organo metallic compound of group III A of the MANUEFACTURE OF ORGANOLEAD COMPOUNDS 5 periodic table, that is boron, aluminum gallium, and in Sidney M. Blitzer and Tillmon H. Pearson, Baton Rouge, dium, wherein the group II. A metal is the sole metal La., assignors to Ethyl Corporation, New York, N.Y., in the metallo organic compound. a corporation of Delaware In accordance with this invention, it has been dis covered that to produce organolead compounds it is un No Drawing. Application March 28, 1955 O necessary, to start with a lead alloy, or in fact to em. Seria No. 497,378 ploy metallic lead at all. Among the lead halides that 7 Claims. C.260-437) can be employed in the process of this invention are lead chloride, lead bromide, leadiodide, lead bromoiodide, lead chloroiodide, and lead chlorobromide. This invention relates to a process for the manufacture 5 The process of the present invention can best be under of organolead compounds. In particular, this invention stood by considering the: chemical equation involved. In is directed to an improved process for the manufacture general, the process proceeds according to the equation of tetraethyllead. The process employed in present commercial practice for the manufacture of tetraethylead has been in use for where R is an organic radical and X is halogen having a number of years and, in general, is satisfactory. How atomic weight greater than 35, and M represents a metal ever, it has certain disadvantages, which are overcome by of group III A of the periodic table, namely boron, practicing our invention. It proceeds by reacting a so aluminum, gallium, or indium. In the preferred embodi dium-lead alloy, of composition controlled to correspond ment of this process the organic radicals are hydrocarbons substantially to NaPb, with ethyl chloride according to 25 and particularly are non-aromatic or aromatic. Among the following equation: the non-aromatic.radicals we can employ alkyl or hydro carbon substituted alkyl radicals. In general, we prefer the lower alkyl radicals having up to about eight carbon With the highest yields obtained thereby, only about atoms. Among the aromatic radicals which can be em 22 percent of the lead present in the NaPb. alloy is con 30 ployed in the above reaction are included phenyl and hy verted to tetraethylead. Under conditions of best opera drocarbon substituted phenyl radicals such as the alkaryl tion of this process, no one heretofore, as far as we are radicals. In general, aromatic radicals having up to ten aware, has been able to increase this yield of tetraethyl carbon atoms are satisfactory. Thus, the compounds MR lead by even a few percent, due to the inherent limitation may be considered alkylating or arylating agents with re in yield as is apparent from the consideration of the 35 spect to the lead in the inorganic lead compound. above equation. It should be noted that in this reaction Of greatest current importance from a commercial at least 75 percent of the lead originally employed is not standpoint is the manufacture of tetraethylead by the proc alkylated. Thus, in this reaction, large quantities of lead ess of this invention. This embodiment can be illustrated must be recovered and reprocessed to NaPb alloy in or by reference to the following equation representing the der to make it economical. A further disadvantage of 40 preferred embodiment. such a large quantity of unreacted lead is that valuable reaction space in the reaction vessel is occupied by ma terials which are essentially inert for the manufacture of Illustrative of the alkylating or arylating agents which tetraethyllead under present conditions and mode of opera we can employ are trimethyl aluminum, trimethyl gal tion. 45 lium, trimethyl boron, trimethyl indium, triethyl alumi Other processes for the production of organolead com num, triethyl gallium, triethyl boron, triethyl indium, tri pounds, and in particular tetraethylead, have been de propyl aluminum, tripropyl gallium, tripropyl boron, tri vised to consume the lead produced in the above equa propyl indium, tributyl aluminum, tributyl gallium, tri tion. While such processes are satisfactory from the butyl boron, tributyl indium, triamy aluminum, triamyl. standpoint of lead consumption, they suffer an additional 50 gallium, triamyl boron, triamyl indium, and the like up to drawback in common with the present commercial proc about trioctyl aluminum, trioctyl gallium, trioctyl boron, ess in that they require organohalide as the ethylating trioctyl indium, triphenyl aluminum, triphenyl gallium, agent. One such process is that described in tJ. S. Patent triphenyl boron, triphenyl indium, tribenzyl aluminum, 2,535,190 wherein lead as, for example, that produced in tribenzyl gallium, tribenzyl boron, tribenzyl indium, tri-. the commercial process, is treated with metallic mag 55 tolyl aluminum, tritolyl gallium, tritolyl boron, tritolyl nesium and ethyl chloride in the presence of a catalyst indium, triphenethyl aluminum, triphenethyl gallium, tri preferably an alkyl ether. Thus, in this process as well phenethyl boron, triphenethyl indium, tributylphenyl alu as the present commercial process, the tetraethylead man minum, tributylphenyl gallium, tributylphenyl boron, tri ufacturing operation is restricted by the necessary balance butylphenyl indium, tri(diethylphenyl) aluminum, tri(di between the metallic sodium required and the organic 60 ethylphenyl) gallium, tri(diethylphenyl) boron, tri(die chlorine in the ethyl chloride. ethylphenyl) indium and the like. In addition to the nor It is therefore an object of this invention to provide a mal alkyl aluminum, boron, gallium and indium com process for the manufacture of organolead., compounds pounds indicated heretofore, the branched chain isomers which overcomes the above objections to the present com can be employed. Furthermore, mixed organo aluminum mercial process and those processes which have been pro 65 compounds can be employed to produce mixed organo posed more recently as an improvement thereover. Par lead-compounds. Such raw materials include, for ex ticularly, it is an object of the invention to increase the ample, dimethyl ethyl aluminum, dimethyl phenyl alumi conversion of lead to tetraethyllead above that obtained num, dibutyl phenyl gallium, diphenyl methylboron, and in present commercial practice without requiring the use the like. of metallic sodium, metallic lead, or alkyl halogen com 70 By the process of this invention, as much as 50 percent pounds. of the lead in the foregoing lead salts is directly converted These and other objects of this invention are accorn to organolead, or in particular, in a commercial embodi m 3 - - - 4 ment, to tetraethyllead. The remaining portion of the of the product suitable for other applications or so that lead is in a highly active form as lead metal and is ideally they can be readily removed by distillation at a tempera suited for employment in the commercial process em ture at which the organolead compound will not decom ploying sodium-lead alloy or in that which proposes the pose. Other inert carrier liquids are satisfactory and reaction of metallic lead with an alkylating agent in the where the product is a liquid such as, for example, in presence of magnesium and a catalyst. Conversely, the the manufacture of tetraethyllead, the organolead com lead so produced by this invention can be recycled eco pound itself can be employed as a carrier liquid. In such nomically to the present process by conversion to the an operation, economies are effected by obviating the ne appropriate lead salt. W cessity of recovery by other means than merely filtration . Our invention is adaptable to the production of organo 0 of the co-produced solids. Another class of carrier liq lead compounds generally, such as tetraethyllead, tetra uids comprises the liquid amines, liquid ammonia, and methyllead, dimethyldiethyllead, tetraphenylead, triethyl ethers. The principal criterion of choice, therefore, of a phenylead and tetrapropyllead. Nevertheless, for con carrier is the physical characteristic of the organolead venience in describing our invention hereafter, specific compound produced, and the inertness of the liquid to reference will be made to tetraethylead, the most widely 5 the organo aluminum reactant. Certain of the afore known because of its use as an anti-knock agent. When in entioned reactant carriers, while inert to the reactants, ever, in the following description, this material is referred exhibit a beneficial effect on the reaction which may be. to, it is to be understood that other organolead com considered catalytic in nature and contribute to the ease pounds or mixtures can be made by our process. of reaction and rapidity of arriving at completion of the Likewise, aluminum triethyl is the preferred organic 20 reaction at relatively lower temperatures and pressures. reactant in the process of this invention and for conven In general, when conducting this process in the pres ience, sometimes hereinafter the invention will be de ence of a liquid carrier as above, the amount of carrier scribed with reference to the employment of aluminum should be proportioned so as to provide adequate heatre triethyl. However, when this material is referred to, it moval facilities. In general, the load on the heat trans is to be understood that the other group III A metals can fer medium is proportional to the concentration or rela be employed as the metallic organic reactant of this tive proportion of the reactants and carrier. In a batch process. operation, it is preferred to employ the liquid diluent in Generally, the process of this invention is conducted as the proportion of as much as 1,000 parts per part of follows.
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