Dilithium acetylide
Dilithium acetylide
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Dilithium acetylide

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Dilithium acetylide

Dilithium acetylide is an organometallic compound with the formula Li2C2. It is typically derived by double deprotonation of acetylene. X-ray crystallography confirms the presence of C≡C subunits attached to lithium, resulting in a polymeric structure. Li2C2 is one of an extensive range of lithium-carbon compounds, which include the lithium-rich Li4C, Li6C2, Li8C3, Li6C3, Li4C3, Li4C5, and the graphite intercalation compounds LiC6, LiC12, and LiC18. It is an intermediate compound produced during radiocarbon dating procedures.

Li2C2 is the most thermodynamically-stable lithium-rich carbide 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. CCl4. Lithium carbide is sometimes confused with the drug lithium carbonate, Li2CO3, because of the similarity of its name.

In the laboratory samples may be prepared by treating acetylene with butyl lithium:

Instead of butyl lithium, a solution of lithium in ammonia can be used to prepare Li2C2. In this case, a transient adduct Li2C2·C2H2·2NH3 if formed. It decomposes with release of ammonia at room temperature.

Samples prepared from acetylene generally are poorly crystalline. Crystalline samples may be prepared by a reaction between molten lithium and graphite at over 1000 °C. Li2C2 can also be prepared by reacting CO2 with molten lithium.[citation needed]

Other method for production of Li2C2 is heating of metallic lithium in atmosphere of ethylene. Lithium hydride is a coproduction:

Lithium carbide hydrolyzes readily to form acetylene as well as Lithium hydroxide:

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