Choline chloride

Choline chloride is an organic compound with the formula [(CH3)3NCH2CH2OH]Cl. It is bifunctional, containing both quaternary ammonium salt and an alcohol. The cation is choline, which occurs naturally. It is a white, water-soluble salt used mainly in animal feed.[2]

Choline chloride
Names
Preferred IUPAC name
2-Hydroxy-N,N,N-trimethylethan-1-aminium chloride
Other names
  • (2-Hydroxyethyl)trimethylammonium chloride
  • Hepacholine
  • Biocolina
  • Lipotril
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.596
E number E1001(iii) (additional chemicals)
UNII
  • InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1 Y
    Key: SGMZJAMFUVOLNK-UHFFFAOYSA-M Y
  • InChI=1/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1
    Key: SGMZJAMFUVOLNK-REWHXWOFAH
  • [Cl-].OCC[N+](C)(C)C
Properties
C5H14ClNO
Molar mass 139.62 g·mol−1
Appearance White or deliquescent crystals
Melting point 302 °C (576 °F; 575 K) (decomposes)
very soluble (>650 g/l)[1]
Hazards
NFPA 704 (fire diamond)
2
0
0
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis

In the laboratory, choline can be prepared by methylation of dimethylethanolamine with methyl chloride.

Choline chloride is mass-produced with world production estimated at 160 000 tons in 1999.[2] Industrially, it is produced by the reaction of ethylene oxide, hydrogen chloride, and trimethylamine,[3] or from the pre-formed salt:[4]

Applications

It is an important additive in feed especially for chickens where it accelerates growth. It forms a deep eutectic solvent with urea, ethylene glycol, glycerol, and many other compounds.

It is also used as a clay control additive in fluids used for hydraulic fracturing.[5]

Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs, the compound is often present as phosphatidylcholine.

References
  1. "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride" (PDF). Archived from the original (PDF) on 2017-07-12.
  2. Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001. ISBN 3527306730.{{cite encyclopedia}}: CS1 maint: uses authors parameter (link)
  3. |title= Johnson Matthey Process Technology - Choline chloride licensed process
  4. "Choline chloride" (PDF). Screening Information Data Set (SIDS) for High Production Volume Chemicals. IPCS INCHEM. Archived from the original (PDF) on 2017-07-12. Retrieved 2009-11-10.
  5. "What Chemicals Are Used". FracFocus. Retrieved 19 September 2014.
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