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Choline chloride

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Choline chloride
Choline chloride
Names
IUPAC name 2-hydroxy-N,N,N-trimethylethanaminium chloride OR (2-hydroxyethyl)trimethylammonium chloride
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.596 Edit this at Wikidata
E number E1001(iii) (additional chemicals)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1Key: SGMZJAMFUVOLNK-UHFFFAOYSA-M
  • InChI=1/C5H14NO.ClH/c1-6(2,3)4-5-7;/h7H,4-5H2,1-3H3;1H/q+1;/p-1Key: SGMZJAMFUVOLNK-REWHXWOFAH
SMILES
  • .OCC(C)(C)C
Properties
Chemical formula C5H14ClNO
Molar mass 139.62 g·mol
Appearance White or deliquescent crystals
Melting point 302 °C (decomposes)
Solubility in water very soluble (>650 g/l)
Hazards
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
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Choline chloride is an organic compound and a quaternary ammonium salt. It has a choline cation with chloride anion. Alternative names are hepacholine, biocolina and lipotril.

Synthesis

In the laboratory choline can be prepared by methylation of dimethylethanolamine with methyl chloride.

In the industrial Davy Process Technology route choline chloride is produced from ethylene oxide, hydrochloric acid, and trimethylamine, or from the pre-formed salt:

Applications

Choline chloride is mass produced and is an important additive in feed especially for chicken where it accelerates growth. With urea it forms a deep eutectic solvent. Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs the compound is often present as phosphatidylcholine.

References

  1. "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride" (PDF).
  2. Davy Process Technology
  3. "Choline chloride" (PDF). Screening Information Data Set (SIDS) for High Production Volume Chemicals. IPCS INCHEM.
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