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
IUPAC name
2-Hydroxy-N,N,N-trimethylethanaminium chloride OR (2-hydroxyethyl)trimethylammonium chloride
Other names
hepacholine, biocolina and lipotril.
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.596
E number E1001(iii) (additional chemicals)
UNII
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
Safety data sheet External MSDS
NFPA 704 (fire diamond)
Flammability code 0: Will not burn. E.g. waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
2
0
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 produce 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.

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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.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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