Tetralithiomethane

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Tetralithiomethane
Names
IUPAC name
Tetralithiomethane
Other names
  • Carbon tetralithium
  • Lithium carbide
  • Tetralithium carbide
Identifiers
3D model (JSmol)
  • InChI=1S/C.4Li
    Key: SOAIVWSMVGHHPJ-UHFFFAOYSA-N
  • LiC(Li)(Li)Li
Properties
CLi4
Molar mass 39.77 g·mol−1
Appearance Red solid
Melting point 225 °C (437 °F; 498 K)[1] (decomposes)
Hydrolysis
Solubility Soluble in cyclohexane
Hazards
GHS labelling:
GHS02: Flammable
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetralithiomethane, also known as tetralithium carbide, is an organolithium compound with the formula CLi4. It is an extremely pyrophoric red solid and is the lithium analog of methane.[2]

Production

Its main route of production is by the lithiation of tetrakis(chloromercurio)methane by tert-butyllithium. It can also be produced by the reaction of lithium metal and carbon tetrachloride at 900 °C:[2][3]

8 Li + CCl4 → CLi4 + 4 LiCl

However, this method also produces byproducts, such as lithium carbide.

Reactions

Tetralithiomethane hydrolyzes vigorously in contact with water producing methane gas and lithium hydroxide:[2]

CLi4 + 4 H2O → CH4 + 4 LiOH

Deuterated methane can also be produced by reacting heavy water with tetralithiomethane. When tetralithiomethane is heated to 225 °C, it decomposes to lithium carbide and lithium metal.[1][2]

Due to the known affinity of lithium ions for hydrogen molecules and therefore potential applications in hydrogen storage materials, tetralithiomethane has been studied computationally for its aggregation, H2 affinity, and binding to various graphene-type surfaces.[4]

References

  1. ^ a b Lawrence A. Shimp; John A. Morrison; John A. Gurak; John W. Chinn Jr.; Richard J. Lagow (1981). "Observations on the nature of polylithium organic compounds and their rearrangements". Journal of the American Chemical Society. 103 (19): 5951–5953. doi:10.1021/ja00409a074.
  2. ^ a b c d Adalbert Maercker; Manfred Theis (1984). "Tetralithiomethane". Angewandte Chemie International Edition. 23 (12): 995–996. doi:10.1002/anie.198409951.
  3. ^ C. Chung; R. J. Lagow (1972). "Reaction of lithium atoms at 800 °C with chlorocarbons; a new route to polylithium compounds". Journal of the Chemical Society, Chemical Communications (19): 1078–1079. doi:10.1039/C3972001078B.
  4. ^ Er, Süleyman; de Wijs, Gilles A.; Brocks, Geert (2009). "Hydrogen Storage by Polylithiated Molecules and Nanostructures". J. Phys. Chem. C. 113 (20): 8997–9002. arXiv:0902.2339. doi:10.1021/jp901305h. S2CID 17237753.
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