Triethylaluminium
Names | |
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IUPAC name
Triethylalumane
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Identifiers | |
3D model (
JSmol ) |
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Abbreviations | TEA,[1] TEAl,[2] TEAL[3] |
ChemSpider | |
ECHA InfoCard
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100.002.382 |
EC Number |
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PubChem CID
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UNII | |
UN number | 3051 |
CompTox Dashboard (EPA)
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Properties | |
C12H30Al2 | |
Molar mass | 228.335 g·mol−1 |
Appearance | Colorless liquid |
Density | 0.8324 g/mL at 25 °C |
Melting point | −46 °C (−51 °F; 227 K) |
Boiling point | 128 to 130 °C (262 to 266 °F; 401 to 403 K) at 50 mmHg |
Reacts | |
Solubility | Ether, hydrocarbons, THF |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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pyrophoric |
GHS labelling: | |
Danger | |
H250, H260, H314 | |
P210, P222, P223, P231+P232, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P402+P404, P405, P422, P501 | |
NFPA 704 (fire diamond) | |
Flash point | −18 °C (0 °F; 255 K) |
Related compounds | |
Related compounds
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Trimethylaluminium Triisobutylaluminium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Triethylaluminium is one of the simplest examples of an
Structure and bonding
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.[6] 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.[7][8]
Synthesis and reactions
Triethylaluminium can be formed via several routes. The discovery of an efficient route was a significant technological achievement. The multistep process uses aluminium,
- 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:[9]
- 6 Al2Cl3Et3 + 18 Na → 3 Al2Et6 + 6 Al + 18 NaCl
Reactivity
The Al–C bonds of triethylaluminium are
- 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
- Al2Et6 + 2 L → 2 LAlEt3
Applications
Precursors to fatty alcohols
Triethylaluminium is used industrially as an intermediate in the production of
- Al2(C2H5)6 + 18 C2H4 → Al2(C8H17)6
Subsequently, these trialkyl compounds are oxidized to aluminium alkoxides, which are then hydrolysed:
- Al2(C8H17)6 + 3 O2 → Al2(OC8H17)6
- Al2(OC8H17)6 + 6 H2O → 6 C8H17OH + 2 Al(OH)3
Co-catalysts in olefin polymerization
A large amount of TEAL and related aluminium alkyls are used in
Reagent in organic and organometallic chemistry
Triethylaluminium has niche uses as a precursor to other organoaluminium compounds, such as diethylaluminium cyanide:[12]
Pyrophoric agent
Triethylaluminium ignites on contact with air and will ignite and/or decompose on contact with water, and with any other oxidizer
Triethylaluminium
See also
- Triethylborane, used as an ignitor in the Pratt & Whitney J58 turbojet/ramjet engines.
- Trimethylaluminium
References
- ^ a b Mission Status Center, June 2, 2010, 1905 GMT, SpaceflightNow, accessed 2010-06-02, Quotation: "The flanges will link the rocket with ground storage tanks containing liquid oxygen, kerosene fuel, helium, gaserous nitrogen and the first stage ignitor source called triethylaluminum-triethylborane, better known as TEA-TEB."
- ^ "Gulbrandsen Chemicals, Metal Alkyls: Triethylaluminum (TEAl)". Gulbrandsen. Archived from the original on December 13, 2017. Retrieved December 12, 2017.
Triethylaluminum (TEAl) is a pyrophoric liquid...
- ^
Malpass, Dennis B.; Band, Elliot (2012). Introduction to Industrial Polypropylene: Properties, Catalysts Processes. John Wiley & Sons. ISBN 9781118463208.
- ^ ISBN 978-3527306732.
- ISBN 978-3-527-29390-2.
- ISBN 0-12-352651-5.
- .
- ISSN 0022-3654.
- ^ Krause, M. J; Orlandi, F; Saurage, A T.; Zietz, J R, "Organic Aluminum Compounds" Wiley-Science 2002.
- ISBN 978-3-527-29390-2
- ISBN 9780470504437.
- ^ Wataru Nagata and Yoshioka Mitsuru (1988). "Diethylaluminum Cyanides". Organic Syntheses; Collected Volumes, vol. 6, p. 436.
- ^ TEA Material Safety Data Sheet Archived 2006-11-14 at the Wayback Machine, accessed March 27, 2007
- ^ "Triethylaluminum (CAS 97-93-8) - Chemical & Physical Properties by Cheméo".
- ^ M202A1 Flame Assault Shoulder Weapon (Flash), inetres.com
- ^ Encyclopedia of Explosives and Related Items, Vol.8, US Army