Choline chloride
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| Preferred IUPAC name
2-Hydroxy-N,N,N-trimethylethan-1-aminium chloride | |
Other names
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PubChem CID
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CompTox Dashboard (EPA)
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| 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 | |
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Main hazards
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Corrosive |
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| NFPA 704 (fire diamond) | |
| 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).
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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]
Synthesis
[edit | edit source]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
[edit | edit source]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
[edit | edit source]Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs, the compound is often present as phosphatidylcholine.
References
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