Aliquat 336

Aliquat 336
IUPAC name

N-Methyl-N,N-dioctyloctan-1-ammonium chloride
Other names

Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
Identifiers
CAS number 63393-96-4 Y
ChemSpider 19948 Y
RTECS number UZ2997500
Jmol-3D images Image 1
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Properties
Molecular formula C25H54ClN
Molar mass 404.16 g mol−1
Appearance Colorless viscous liquid
Density 0.884 g/cm³
Melting point

-20 °C, 253 K, -4 °F
Boiling point

225 °C, 498 K, 437 °F
Viscosity 1500 mPa·s at 30 °C
Hazards
MSDS External MSDS
EU classification Harmful (Xn)
R-phrases R22 R38 R41 R50/53
S-phrases S26 S39 S60 S61
Main hazards Toxic (USA)
Flash point 113 °C (closed cup)
Related compounds
Related Aliquat 100, Aliquat 134, Aliquat 175, Aliquat HTA-1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Aliquat 336 (Starks' catalyst) is a mixture of C8 (octyl) and C10 (decyl) chains with C8 predominating. It is a quaternary ammonium salt used as a phase transfer catalyst and metal extraction reagent.

Applications

Aliquat 336 is used as a phase transfer catalyst,[1] including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid.[2] This reaction is more environmentally friendly. It is an example of green chemistry, compared with the traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, which produce hazardous wastes.

References

  1. ^ C.M. Starks (1971). "Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts". J. Amer. Chem. 93: 195. doi:10.1021/ja00730a033. 
  2. ^ S.M. Reed and J.E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Ed. 77 (12): 1627–8. doi:10.1021/ed077p1627.