"TBAB" redirects here. For t-butylamine borane, see borane tert-butylamine complex.

Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst.[4] It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions. The anhydrous form is a white solid.[2]

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.[5]

Preparation and reactions

Tetrabutylammonium bromide can be prepared by the alkylation of tributylamine with 1-bromobutane.[2]

Tetrabutylammonium bromide is used to prepare other salts of the tetrabutylammonium cation by salt metathesis reactions.[6]

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.[2]

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.[7]

See also

References

  1. ^ Mark R. J. Elsegood (2011). "Tetra-n-butylammonium bromide: a redetermination at 150 K addressing the merohedral twinning". Acta Crystallographica Section E. 67 (10): 2599. Bibcode:2011AcCrE..67o2599E. doi:10.1107/S1600536811032612.
  2. ^ a b c d Charette, André B.; Chinchilla, Rafael; Nájera, Carmen (2007). "Tetrabutylammonium Bromide". In Paquette, Leo A. (ed.). Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt011.pub2. ISBN 978-0471936237.
  3. ^ Applied Catalysis A: General 241 (2003) 227–233
  4. ^ Henry J. Ledon (1988). "Diazo transfer by means of phase-transfer catalysis: di-tert-butyl diazomalonate". Organic Syntheses; Collected Volumes, vol. 6, p. 414.
  5. ^ 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. doi:10.1016/j.catcom.2008.03.037.
  6. ^ Klemperer, W. G. (1990). "Tetrabutylammonium Isopolyoxometalates". Inorganic Syntheses. Vol. 27. pp. 74–85. doi:10.1002/9780470132586.ch15. ISBN 9780470132586., Bojes, J.; Chivers, T.; Drummond, I. (1978). "Heptathiazocine(Heptasulfurimide) and Tetrabutylammonium Tetrathionitrate". Inorganic Syntheses. Vol. 18. pp. 203–206. doi:10.1002/9780470132494.ch36. ISBN 9780470132494., Ceriotti, A.; Longoni, G.; Marchionna, M. (1989). "Bis(Tetrabutylammonium) Hexa-μ-Carbonyl-Hexacarbonylhexaplatinate(2 -), [N(C 4 H 9 ) 4 ] 2 [Pt 6 (Co) 6 (μ-Co) 6 ]". Inorganic Syntheses. Vol. 26. pp. 316–319. doi:10.1002/9780470132579.ch57. ISBN 978-0-471-50485-6.;Christou, George; Garner, C. David; Balasubramaniam, A.; Ridge, Brian; Rydon, H. N. (1982). "9. Tetranuclear Iron-Sulfur and Iron-Selenium Clusters". Tetranuclear Iron-Sulfur and Iron-Selenium Clusters. Inorganic Syntheses. Vol. 21. pp. 33–37. doi:10.1002/9780470132524.ch9. ISBN 9780470132524..
  7. ^ 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. doi:10.1016/j.jct.2011.04.021. ISSN 0021-9614.