Tetrabutylammonium bromide explained
Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[1]
In addition to being cheap, tetrabutylammonium bromide is also environmentally friendly, has a greater degree of selectivity, is operationally simple, non-corrosive, and can be recycled easily as well.[2]
Preparation and reactions
Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane.[1]
Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions.[3]
It serves as a source of bromide ions for substitution reactions. It is a commonly used phase transfer catalyst. As its melting point is just over 100 °C and decreases in the presence of other reagents, it can be considered an ionic liquid.[1]
Role in semi-clathrate formation
TBAB is being extensively studied as a thermodynamic promoter in the formation of semi-clathrate hydrates which greatly brings down the pressure - temperature requirement for forming gas hydrates.[4]
See also
Notes and References
- Book: Paquette. Leo A.. Charette. André B.. Chinchilla. Rafael. Nájera. Carmen. Encyclopedia of Reagents for Organic Synthesis. Tetrabutylammonium Bromide. 2007. 10.1002/047084289X.rt011.pub2. 978-0471936237.
- Chary . M.V. . Keerthysri . N.C. . Vupallapati . S.V.N. . Lingaiah . N. . Kantevari . S. . 2008 . Tetrabutylammonium bromide (TBAB) in isopropanol: An efficient, novel, neutral and recyclable catalytic system for the synthesis of 2,4,5-trisubstituted imidazoles. . Catal. Commun. . 9 . 10 . 2013–2017. 10.1016/j.catcom.2008.03.037 .
- Book: Walter G. Klemperer. W. G.. Klemperer. Inorganic Syntheses. Tetrabutylammonium Isopolyoxometalates. 1990. 27. 74–85 . 10.1002/9780470132586.ch15. 9780470132586., Book: J.. Bojes. T. . Chivers. I.. Drummond . Inorganic Syntheses. Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate. 1978. 18 . 203–206. 10.1002/9780470132494.ch36. 9780470132494., Book: A. . Ceriotti. G. . Longoni. M.. Marchionna. Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C 4 H 9) 4 ] 2 [Pt 6 (Co) 6 (μ-Co) 6 ] . Inorganic Syntheses. 1989. 26. 316–319 . 10.1002/9780470132579.ch57. 978-0-471-50485-6 . ;Book: Inorganic Syntheses. George . Christou. C. David. Garner. A.. Balasubramaniam. Brian. Ridge. H. N.. Rydon. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters. 9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters . 1982. 21. 33–37. 10.1002/9780470132524.ch9. 9780470132524 . .
- Meysel . Philipp . Oellrich . Lothar . Raj Bishnoi . P. . Clarke . Matthew A. . October 2011 . Experimental investigation of incipient equilibrium conditions for the formation of semi-clathrate hydrates from quaternary mixtures of (CO2+ N2+ TBAB + H2O) . The Journal of Chemical Thermodynamics . 43 . 10 . 1475–1479 . 10.1016/j.jct.2011.04.021 . 0021-9614.
