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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
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
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
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 ?)

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,[2] or from the pre-formed salt:[3]

Applications

Choline chloride is mass-produced and is an important additive in feed especially for chickens 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. It is also used as an additive in fluids used for hydraulic fracturing.[4]

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.
  4. ^ "What Chemicals Are Used". FracFocus. Retrieved 19 September 2014.
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