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 a bifunctional compound, meaning, it contains both a 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]
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]
Related salts
Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs, the compound is often present as phosphatidylcholine.
References
- ^ "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride" (PDF). Archived from the original (PDF) on 2017-07-12.
- ^ "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. Retrieved 11 November 2019.
- ^ a b 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.
- ^ title=Johnson Matthey Process Technology - Choline chloride licensed process
- ^ "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.
- ^ Kirk RE, et al. (2000). Kirk-Othmer encyclopedia of chemical technology. Vol. 6 (4th ed.). John Wiley & Sons. pp. 100–102. ISBN 9780471484943.
- ^ "What Chemicals Are Used". FracFocus. Archived from the original on 2 July 2020. Retrieved 19 September 2014.