Chemistry:Tetrapropylammonium chloride

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Tetrapropylammonium chloride
Tetrapropylammonium chloride structural formula
Names
IUPAC name
Tetrapropylazanium chloride[1]
Other names
  • 1-Propanaminium, N,N,N-tripropyl-, chloride[1]
  • TPAC[2]
  • TPACl[3]
  • TPrACl[4]
Identifiers
3D model (JSmol)
ChemSpider
EC Number
  • 227-375-5
Properties
[(CH
3CH
2CH
2)
4N]Cl
Molar mass 221.81 g·mol−1
Appearance White crystalline solid[5][3][1]
Odor Odorless[1]
Melting point 240–242 °C (464–468 °F; 513–515 K)[5]
Soluble[3]
Solubility Soluble in polar solvents like alcohols.[3] Soluble in acetone.[4]
Structure
Tetrahedral at N
Hazards
Main hazards Serious eye irritation
GHS pictograms GHS07: Harmful
GHS Signal word Warning
HH315Script error: No such module "Preview warning".Category:GHS errors, HH319Script error: No such module "Preview warning".Category:GHS errors, HH335Script error: No such module "Preview warning".Category:GHS errors
PP261Script error: No such module "Preview warning".Category:GHS errors, PP264Script error: No such module "Preview warning".Category:GHS errors, PP264+P265Script error: No such module "Preview warning".Category:GHS errors, PP271Script error: No such module "Preview warning".Category:GHS errors, PP280Script error: No such module "Preview warning".Category:GHS errors, PP302+P352Script error: No such module "Preview warning".Category:GHS errors, PP304+P340Script error: No such module "Preview warning".Category:GHS errors, PP305+P351+P338Script error: No such module "Preview warning".Category:GHS errors, PP319Script error: No such module "Preview warning".Category:GHS errors, PP321Script error: No such module "Preview warning".Category:GHS errors, PP332+P317Script error: No such module "Preview warning".Category:GHS errors, PP337+P317Script error: No such module "Preview warning".Category:GHS errors, PP362+P364Script error: No such module "Preview warning".Category:GHS errors, PP403+P233Script error: No such module "Preview warning".Category:GHS errors, PP405Script error: No such module "Preview warning".Category:GHS errors, PP501Script error: No such module "Preview warning".Category:GHS errors
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity (yellow): no hazard codeSpecial hazards (white): no code
1
2
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetrapropylammonium chloride is an organic compound with the chemical formula [(CH
3CH
2CH
2)
4N]Cl. It is a white, very hygroscopic crystalline solid.[2][6] Tetrapropylammonium chloride is a quaternary ammonium salt. It consists of tetrapropylammonium cations [(CH
3CH
2CH
2)
4N]+
 and chloride anions Cl−
.

Synthesis and properties

Tetrapropylammonium chloride is synthesized by reaction between tripropylamine and 1-chloropropane.[2]

(CH
3CH
2CH
2)
3N + CH
3CH
2CH
2Cl → [(CH
3CH
2CH
2)
4N]Cl

The density of a concentrated aqueous solution of tetrapropylammonium chloride is less than that of a dilute solution at the same temperature.[6]

The fully deuterated form of tetrapropylammonium chloride, [(CD
3CD
2CD
2)
4N]Cl, is also a white solid.[3]

Uses

Tetrapropylammonium chloride is used as antimicrobial agent.[3] It is also widely used as a phase-transfer catalyst in organic synthesis, facilitating the transfer of reactants between immiscible phases. It is used to stabilize emulsions and enhance solubility of hydrophobic compounds in aqueous solutions.[2][3]

References

  1. ↑ 1.0 1.1 1.2 1.3 PubChem. "Tetrapropylammonium chloride". https://pubchem.ncbi.nlm.nih.gov/compound/Tetrapropylammonium-chloride. 
  2. ↑ 2.0 2.1 2.2 2.3 BENCHCHEM. "Tetrapropylammonium Chloride: A Comprehensive Technical Guide to its Synthesis and Applications". https://pdf.benchchem.com/153/Tetrapropylammonium_Chloride_A_Comprehensive_Technical_Guide_to_its_Synthesis_and_Applications.pdf. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 cymitquimica.com. "CAS 5810-42-4: Tetrapropylammonium chloride". https://cymitquimica.com/cas/5810-42-4/. 
  4. ↑ 4.0 4.1 ChemSpider. "TPrACl". https://www.chemspider.com/Chemical-Structure.72171.html. 
  5. ↑ 5.0 5.1 Sigma-Aldrich. "Tetrapropylammonium chloride". https://www.sigmaaldrich.com/GB/en/sds/aldrich/438243. 
  6. ↑ 6.0 6.1 McDavid, J. W. (15 September 2014). "XXXVI.—Specific Volume of Solutions of Tetra-propyl-ammonium Chloride" (in en). Proceedings of the Royal Society of Edinburgh 30: 515–520. doi:10.1017/S0370164600030959. ISSN 0370-1646. https://www.cambridge.org/core/journals/proceedings-of-the-royal-society-of-edinburgh/article/abs/xxxvispecific-volume-of-solutions-of-tetrapropylammonium-chloride/C2A7754D86A9C35CE22BE0ACF084786C. 



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