Choline chloride explained

Choline chloride is an organic compound with the formula . It is a quaternary ammonium salt, consisting of choline cations and chloride anions . It is a bifunctional compound, meaning, it contains both a quaternary ammonium functional group and a hydroxyl functional group. The anion of this salt, choline, occurs in nature in living beings.^[1] Choline chloride is a white, water-soluble salt used mainly in animal feed.^[2]

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]

Choline chloride can also be made by treating trimethylamine with 2-chloroethanol.^[5]

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.^[6]

Related salts

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

Notes and References

1. Web site: February 2015 . Choline . 11 November 2019 . Micronutrient Information Center, Linus Pauling Institute, Oregon State University.
2. Encyclopedia: Matthias Frauenkron . Johann-Peter Melder . Günther Ruider . Roland Rossbacher . Hartmut Höke . Ethanolamines and Propanolamines . Ullmann's Encyclopedia of Industrial Chemistry . 2002 . Wiley-VCH . Weinheim . 10.1002/14356007.a10_001 . 3527306730.
3. https://web.archive.org/web/20140918142932/http://www.davyprotech.com/what-we-do/licensed-processes-and-core-technologies/licensed-processes/choline-chloride/specification/ title=Johnson Matthey Process Technology - Choline chloride licensed process
4. Web site: Choline chloride . Screening Information Data Set (SIDS) for High Production Volume Chemicals . . 2009-11-10 . https://web.archive.org/web/20170712141325/http://www.inchem.org/documents/sids/sids/67481.pdf . 2017-07-12 . dead.
5. Book: Kirk-Othmer encyclopedia of chemical technology . Kirk RE . John Wiley & Sons . 2000 . 9780471484943 . 4th . 6 . 100–102 . etal.
6. Web site: What Chemicals Are Used. FracFocus. 19 September 2014. 2 July 2020. https://web.archive.org/web/20200702153204/https://fracfocus.org/chemical-use/what-chemicals-are-used. dead.