Choline chloride

Chemical compound From Wikipedia, the free encyclopedia

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 as an animal and human dietary supplement.[3]

Quick facts Names, Identifiers ...
Choline chloride
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 Edit this at Wikidata
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 diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 ?)
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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 a dietary supplement used to accelerate the growth of chickens.

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

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