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 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]

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
CAS Number	67-48-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:133341 N
ChEMBL	ChEMBL282468 N
ChemSpider	5974 Y
ECHA InfoCard	100.000.596
E number	E1001(iii) (additional chemicals)
PubChem CID	522265
UNII	45I14D8O27 Y
CompTox Dashboard (EPA)	DTXSID4020325
InChI InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1 Y Key: SGMZJAMFUVOLNK-UHFFFAOYSA-M Y InChI=1/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1 Key: SGMZJAMFUVOLNK-REWHXWOFAH
SMILES [Cl-].OCC[N+](C)(C)C
Properties
Chemical formula	[(CH3)3NCH2CH2OH]+Cl−
Molar mass	139.62 g·mol−1
Appearance	White hygroscopic crystals
Melting point	302 °C (576 °F; 575 K) (decomposes)
Solubility in water	very soluble (>650 g/L)[1]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Corrosive
GHS labelling:
Signal word	Danger
NFPA 704 (fire 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 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.^[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.