Tetramethylammonium sulfate

Tetramethylammonium sulfate
Tetramethylammonium sulfate skeletal formula
Names
IUPAC name
Bis(tetramethylazanium) sulfate[1]
Other names
  • Tetramethylammonium sulfate[1]
  • Tetramethylammonium sulfate (2:1)[1]
  • Methanaminium, N,N,N-trimethyl-, sulfate (2:1)[1]
  • Bis(N,N,N-trimethylmethanaminium) sulfate[1]
  • TMA-SO4[2]
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.570
EC Number
  • 238-043-4
  • InChI=1S/2C4H12N.H2O4S/c3*1-5(2,3)4/h2*1-4H3;(H2,1,2,3,4)/q2*+1;/p-2
    Key: KJFVITRRNTVAPC-UHFFFAOYSA-L
  • C[N+](C)(C)C.C[N+](C)(C)C.[O-]S(=O)(=O)[O-]
Properties
[N(CH3)4]2SO4
Molar mass 244.35 g·mol−1
Appearance White hygroscopic crystalline powder[3][4]
Melting point 285 °C (545 °F; 558 K)[4] (decomposes)
Soluble[4]
Solubility Soluble in polar organic solvents[2]
Structure
Tetrahedral at N and S
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Serious eye damage and irritation
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Related compounds
Other anions
Other cations
 Ammonium sulfate
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tetramethylammonium sulfate is a chemical compound with the chemical formula [N(CH3)4]2SO4. It is a white hygroscopic crystalline powder. It is a quaternary ammonium salt. It consists of tetramethylammonium cations [N(CH3)4]+ and sulfate anions SO2−4. It forms the tetrahydrate [N(CH3)4]2SO4·4H2O.[5]

Structure

Tetramethylammonium sulfate tetrahydrate is orthorhombic, with a space group of Pnam, with the lattice constants a = 15.438 Å, b = 13.832 Å, c = 7.923 Å at −26 °C (−15 °F). The crystal structure contains ordered tetramethylammonium cations in channels formed by hydrogen‐bonded chains of water molecules cross linked by interaction with the sulfate anions which are disordered.[5]

Synthesis

Tetramethylammonium sulfate can be synthesized by the reaction between tetramethylammonium hydroxide and sulfuric acid, followed by careful evaporation and crystallization.[6]

2 [N(CH3)4]OH + H2SO4 → [N(CH3)4]2SO4 + 2 H2O

Uses

Tetramethylammonium sulfate is used as a phase transfer catalyst and in organic synthesis. It exhibits properties typical of quaternary ammonium compounds, such as being a surfactant and having antimicrobial activity.[2]

Zinc metal is considered as a promising metal anode for aqueous rechargeable metal ion batteries due to its low electrochemical potential and high theoretical capacity. However, zinc metal suffers from hydrogen evolution reaction and dendrite growth during plating and stripping. A low-cost, effective and non-toxic electrolyte additive, tetramethylammonium sulfate, as a simple cationic surfactant additive for zinc-ion batteries is proposed, to trigger the smooth zinc deposition during battery charging and discharging. It is found that tetramethylammonium sulfate enables the deposition of zinc cations (Zn2+) along the surface of zinc foil laterally without stacking and thus dendrite growth and side reactions are greatly avoided by the electrolyte additive of tetramethylammonium sulfate.[7]

References

  1. 1 2 3 4 5 PubChem. "Tetramethylammonium sulphate (2:1)". pubchem.ncbi.nlm.nih.gov. Retrieved 21 April 2026.
  2. 1 2 3 Cymit Química. "CAS 14190-16-0: Tetramethylammonium sulfate". cymitquimica.com. Retrieved 22 April 2026.
  3. ↑ Sigma-Aldrich. "Tetramethylammonium sulfate". www.sigmaaldrich.com. Retrieved 22 April 2026.
  4. 1 2 3 TCI. "Tetramethylammonium Sulfate". www.tcichemicals.com. Retrieved 22 April 2026.
  5. 1 2 McLean, W. J.; Jeffrey, G.A. (15 November 1968). "Crystal Structure of Tetramethylammonium Sulfate Tetrahydrate". The Journal of Chemical Physics. 49 (10): 4556–4564. Bibcode:1968JChPh..49.4556M. doi:10.1063/1.1669912.
  6. ↑ Suyuan Chemical. "Tetramethylammonium Sulfate: A Comprehensive Commentary". www.ascent-surfactant.com. Retrieved 22 April 2026.
  7. ↑ Cao, H.; Huang, X.; Liu, Y.; Hu, Q.; Zheng, Q.; Huo, Y.; Xie, F.; Zhao, J.; Lin, D. (2022). "An efficient electrolyte additive of tetramethylammonium sulfate hydrate for Dendritic-Free zinc anode for aqueous Zinc-ion batteries". Journal of Colloid and Interface Science. 627: 367–374. Bibcode:2022JCIS..627..367C. doi:10.1016/j.jcis.2022.07.081. PMID 35863195.
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