Manufacture, Properties, and Uses of Organolithium Compounds

The various methods of preparing organolithium compounds and the effect on such preparations of factors such as particle size of the lithium metal, solvent, temperature, and time are reviewed. Particular emphasis is placed on some recent studies which show that lithium dispersions can be used to advantage in the preparation of organolithium compounds. For example, phenyllithium can be prepared from chlorobenzene satisfactorily by using lithium dispersions. The general physical and chemical properties of organolithium compounds of interest to commercial producers and users are covered. Comparisons of stabilities of various types of organolithium compounds are of particular interest. In general, only the aryllithium compounds are sufficiently stable in ether to allow extended storage. Even in hydrocarbon solvents, such as benzene and petroleum ether, storage of organolithium compounds at temperatures of 0°C., or lower, is recommended. A review is presented of the more important present and potential commercial uses of organolithium compounds.