Lithium carbide
Lithium carbide, , often known as dilithium acetylide, is a chemical compound of lithium and carbon, an acetylide. It is an intermediate compound produced during radiocarbon dating procedures. is one of an extensive range of lithium-carbon compounds which include the lithium-rich , , , , , , and the graphite intercalation compounds , , and . is the most thermodynamically-stable lithium-rich compound and the only one that can be obtained directly from the elements. It was first produced by Moissan, in 1896 who reacted coal with lithium carbonate. The other lithium-rich compounds are produced by reacting lithium vapor with chlorinated hydrocarbons, e.g. CCl . Lithium carbide is sometimes confused with the drug lithium carbonate, , because of the similarity of its name. Preparation and chemistry. In the laboratory samples may be prepared by treating acetylene with a solution of lithium in ammonia, on −40°C, with creation of addition compound of LiC • CH • 2NH that decomposes in stream of hydrogen at room temperature giving white powder of LiC Samples prepared in this manner generally are poorly crystalline. Crystalline samples may be prepared by a reaction between molten lithium and graphite at over 1000 °C. LiC can also be prepared by reacting CO with  molten lithium. Other method for production of LiC is heating of metallic lithium in atmosphere of ethylene. Lithium carbide hydrolyzes readily to form acetylene: Lithium hydride reacts with graphite at 400°C forming lithium carbide. Also LiC can be formed when organometallic compound n-Butyllithium reacts with ethyne in THF or EtO used as a solvent, reaction is rapid and highly exothermic. Lithium carbide reacts with acetylene in liquid ammonia rapidly to give a clear solution of lithium acetylide. LiC≡CLi + HC≡CH → 2 LiC≡CH Preparation of the reagent in this way sometimes improves the yield in an ethynylation  over that obtained with reagent prepared from lithium and acetylene. Structure. is a Zintl phase compound and exists as a salt, . Its reactivity, combined with the difficulty in growing suitable single crystals, has made the determination of its crystal structure difficult. It adopts a distorted "anti"-fluorite crystal structure, similar to that of rubidium peroxide () and caesium peroxide (). Each Li atom is surrounded by six carbon atoms from 4 different acetylides, with two acetylides co-ordinating side -on and the other two end-on. The observed C-C distance of 120 pm indicates the presence of a C≡C triple bond. At  high temperatures transforms reversibly to a cubic anti-fluorite structure. Use in radiocarbon dating. There are a number of procedures employed, some that burn the sample producing CO that is then reacted with lithium, and others where the carbon containing sample is reacted directly with lithium metal. The outcome is the same: LiC is produced, which can then be used to create species easy to use in mass spectroscopy, like acetylene and benzene. Note that lithium nitride may be formed and this produces ammonia when hydrolyzed, which contaminates the acetylene gas.