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Tetraethylammonium hydroxide

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Tetraethylammonium hydroxide
Names
IUPAC name Tetraethylazanium hydroxide
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.977 Edit this at Wikidata
EC Number
  • 201-073-3
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H20N.H2O/c1-5-9(6-2,7-3)8-4;/h5-8H2,1-4H3;1H2/q+1;/p-1Key: LRGJRHZIDJQFCL-UHFFFAOYSA-M
SMILES
  • CC(CC)(CC)CC.
Properties
Chemical formula C8H21NO
Molar mass 147.262 g·mol
Appearance colorless solutions
Hazards
GHS labelling:
Pictograms GHS05: CorrosiveGHS09: Environmental hazard
Signal word Warning
Hazard statements H314, H410
Precautionary statements P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Tetraethylammonium hydroxide is the organic compound with the formula (C2H5)4NOH, abbreviated Et4NOH. It is the tetraethylammonium salt of hydroxide. It is used and dispensed as solutions in water or alcohols, which are colorless and highly alkaline. The compound is a common reagent in organic synthesis. It is also employed in the preparation of zeolites.

Structure

Structure of Et4NOH4H2O.

Tetraethylammonium hydroxide is most commonly encountered as an aqueous solution. Several hydrates NEt4OH·xH2O. have been crystallized, including x = 4, 5, 9. These salts feature well separated Et4N cations and hydroxide anions. The hydroxide groups are linked by hydrogen bonds to the water of crystallization. Anhydrous Tetraethylammonium hydroxide has not been isolated.

Synthesis and reactions

It is prepared from tetraethylammonium bromide by salt metathesis, using a hydroxide-loaded ion exchange column or by the action of silver oxide. Attempted isolation of Et4NOH induces Hofmann elimination, leading to triethylamine and ethylene.

Treatment of Et4NOH with a wide range of acids gives water and the other tetraethylammonium salts:

Et 4 NOH + HX ⟶ Et 4 NX + H 2 O {\displaystyle {\ce {Et4NOH + HX -> Et4NX + H2O}}}

References

  1. Matsukata, Masahiko; Ogura, Masaru; Osaki, Takayuki; Hari Prasad Rao, Poladi Raja; Nomura, Mikihiro; Kikuchi, Eiichi (1999). "Conversion of dry gel to microporous crystals in gas phase". Topics in Catalysis. 9: 77–92. doi:10.1023/A:1019106421183. S2CID 92539225.
  2. Wiebcke, Michael; Felsche, Jürgen (2000). "NEt4OH·4H2O Xontaining Infinite Hydroxide–Water Ribbons". Acta Crystallographica Section C Crystal Structure Communications. 56 (7): 901–902. doi:10.1107/S0108270100005886. PMID 10935124.
  3. Pelletier, Guillaume (2013). "Tetraethylammonium Hydroxide". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01547. ISBN 978-0471936237.
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