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

PubChem CID

* 522265

UNII |

* 45I14D8O27 Y

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

| [(CH

3NCH
2CH
2OH]+
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
Main hazards | Corrosive
Safety data sheet | External MSDS
GHS Signal word | Danger
NFPA 704 (fire diamond)  |

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

Choline chloride is an organic compound with the formula [(CH

3NCH
2CH
2OH]+
Cl−
. It is a quaternary ammonium salt, consisting of choline cations ([(CH

3NCH
2CH
2OH]+
) 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]

## Contents

* 1 Synthesis
* 2 Applications
* 3 Related salts
* 4 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]

(CH

3N + ClCH
2CH
2OH → [(CH

3NCH
2CH
2OH]+
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.

## References

1. ↑ "Chemical Safety Information from Intergovernmental Organizations - Choline Chloride". http://www.inchem.org/documents/sids/sids/67481.pdf.
2. ↑ "Choline". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. February 2015. https://lpi.oregonstate.edu/mic/other-nutrients/choline.
3. ↑ 3.0 3.1 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. ISBN 3527306730.
4. ↑ title=Johnson Matthey Process Technology - Choline chloride licensed process
5. ↑ "Choline chloride". Screening Information Data Set (SIDS) for High Production Volume Chemicals. IPCS INCHEM. http://www.inchem.org/documents/sids/sids/67481.pdf.
6. ↑ Kirk-Othmer encyclopedia of chemical technology. 6 (4th ed.). John Wiley & Sons. 2000. pp. 100–102. ISBN 9780471484943.
7. ↑ "What Chemicals Are Used". http://fracfocus.org/chemical-use/what-chemicals-are-used. Retrieved 19 September 2014.

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*[CID]: Compound ID