Choline chloride

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Choline chloride
Choline chloride
Names
IUPAC name
2-hydroxy-N,N,N-trimethylethanaminium chloride OR (2-hydroxyethyl)trimethylammonium chloride
Other names
hepacholine, biocolina and lipotril.
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.000.596
E number E1001(iii) (additional chemicals)
UNII
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
Safety data sheet External MSDS
NFPA 704
Flammability code 0: Will not burn. E.g., waterHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
0
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
‹See TfM›☒N verify (what is ☑Y‹See TfM›☒N ?)
Infobox references

Choline chloride is an organic compound with the formula (CH3)3NCH2CH2OH]Cl. It is bifunctional, containing both quaternary ammonium salt and an alcohol. The cation is choline, which occurs naturally. It is a white, water soluble salt used mainly in animal feed.[2]

Synthesis[edit]

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.[2] Industrially, it is produce by the reaction of ethylene oxide, hydrogen chloride, and trimethylamine,[3] or from the pre-formed salt:[4]

Synthesis of choline chloride.png

Applications[edit]

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.[5]

Related salts[edit]

Other commercial choline salts are choline hydroxide and choline bitartrate. In foodstuffs the compound is often present as phosphatidylcholine.

References[edit]

  1. ^ "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride" (PDF).
  2. ^ a b Matthias Frauenkron, Johann-Peter Melder, Günther Ruider, Roland Rossbacher, Hartmut Höke (2002). "Ethanolamines and Propanolamines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a10_001.
  3. ^ Johnson Matthey Process Technology - Choline chloride licensed process
  4. ^ "Choline chloride" (PDF). Screening Information Data Set (SIDS) for High Production Volume Chemicals. IPCS INCHEM.
  5. ^ "What Chemicals Are Used". FracFocus. Retrieved 19 September 2014.