Aliquat 336

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Aliquat 336
Aliquat 336.png
IUPAC name
N-Methyl-N,N,N-trioctylammonium chloride
Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
3D model (JSmol)
ECHA InfoCard 100.058.273
RTECS number UZ2997500
Molar mass 404.16 g·mol−1
Appearance Colorless viscous liquid
Density 0.884 g/cm3
Melting point −20 °C (−4 °F; 253 K)
Boiling point 225 °C (437 °F; 498 K)
Viscosity 1500 mPa·s at 30 °C
Main hazards Toxic (USA)
Safety data sheet External MSDS
Harmful (Xn)
R-phrases (outdated) R22 R38 R41 R50/53
S-phrases (outdated) S26 S39 S60 S61
Flash point 113 °C (235 °F; 386 K) (closed cup)
Related compounds
Aliquat 100, Aliquat 134, Aliquat 175, Aliquat HTA-1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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


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[citation needed] or potassium permanganate[citation needed], which produce hazardous wastes.

Aliquat 336 was used in the total synthesis of Manzamine A by Darren Dixon in an early step to the electrophile.[3]


  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; J. E. Hutchison (2000). "An Environmentally Benign Synthesis of Adipic Acid". J. Chem. Educ. 77 (12): 1627–8. doi:10.1021/ed077p1627. 
  3. ^ Jakubec, Pavol; Hawkins, Alison; Felzmann, Wolfgang; Dixon, Darren J. (2012). "Total Synthesis of Manzamine A and Related Alkaloids". Journal of the American Chemical Society . 134 (42): 17482–17485. doi:10.1021/ja308826x.