Choline chloride

Choline chloride is an organic compound with the formula [(CH3)3NCH2CH2OH]+Cl−. It is a quaternary ammonium salt, consisting of choline cations ([(CH3)3NCH2CH2OH]+) and chloride anions (Cl−). It is bifunctional compound, meaning, it contains both quaternary ammonium functional group and a hydroxyl functional group. The cation of this salt, choline, occurs in nature in living beings.[2] Choline chloride is a white, water-soluble salt used mainly in animal feed.[3]

Choline chloride
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 checkY
    Key: SGMZJAMFUVOLNK-UHFFFAOYSA-M checkY
  • 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
[(CH3)3NCH2CH2OH]+Cl−
Molar mass 139.62 g·mol−1
Appearance White hygroscopic crystals
Melting point 302 °C (576 °F; 575 K) (decomposes)
very soluble (>650 g/L)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Corrosive
GHS labelling:
Danger
NFPA 704 (fire diamond)
NFPA 704 four-colored 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 checkY☒N ?)
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.[3] Industrially, it is produced by the reaction of ethylene oxide, hydrogen chloride, and trimethylamine,[4] or from the pre-formed salt:[5]

Choline chloride can also be made by treating trimethylamine with 2-chloroethanol.[6]

(CH3)3N + ClCH2CH2OH → [(CH3)3NCH2CH2OH]+Cl−

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.[7]

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. "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.
  3. 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.
  4. |title=Johnson Matthey Process Technology - Choline chloride licensed process
  5. "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.
  6. Kirk RE, et al. (2000). Kirk-Othmer encyclopedia of chemical technology. Vol. 6 (4th ed.). John Wiley & Sons. pp. 100–102. ISBN 9780471484943.
  7. "What Chemicals Are Used". FracFocus. Retrieved 19 September 2014.
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