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Concept
Triethylaluminium
Summary
Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name the compound has the formula Al2(C2H5)6 (abbreviated as Al2Et6 or TEA). This colorless liquid is pyrophoric. It is an industrially important compound, closely related to trimethylaluminium.
The structure and bonding in Al2R6 and diborane are analogous (R = alkyl). Referring to Al2Me6, the Al-C(terminal) and Al-C(bridging) distances are 1.97 and 2.14 Å, respectively. The Al center is tetrahedral. The carbon atoms of the bridging ethyl groups are each surrounded by five neighbors: carbon, two hydrogen atoms and two aluminium atoms. The ethyl groups interchange readily intramolecularly. At higher temperatures, the dimer cracks into monomeric AlEt3.
Triethylaluminium can be formed via several routes. The discovery of an efficient route was a significant technological achievement. The multistep process uses aluminium metal, hydrogen gas, and ethylene, summarized as follows:
2 Al + 3 H2 + 6 C2H4 → Al2Et6
Because of this efficient synthesis, triethylaluminium is one of the most available organoaluminium compounds.
Triethylaluminium can also be generated from ethylaluminium sesquichloride (Al2Cl3Et3), which arises by treating aluminium powder with chloroethane. Reduction of ethylaluminium sesquichloride with an alkali metal such as sodium gives triethylaluminium:
6 Al2Cl3Et3 + 18 Na → 3 Al2Et6 + 6 Al + 18 NaCl
The Al–C bonds of triethylaluminium are polarized to such an extent that the carbon is easily protonated, releasing ethane:
Al2Et6 + 6 HX → 2 AlX3 + 6 EtH
For this reaction, even weak acids can be employed such as terminal acetylenes and alcohols.
The linkage between the pair of aluminium centres is relatively weak and can be cleaved by Lewis bases (L) to give adducts with the formula AlEt3L:
Al2Et6 + 2 L → 2 LAlEt3
Triethylaluminium is used industrially as an intermediate in the production of fatty alcohols, which are converted to detergents.
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