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R-phrases (outdated) R22 R38 R41 R50/53
S-phrases (outdated) S26 S39 S60 S61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. It is an ionic liquid.[1]


Aliquat 336 is used as a phase transfer catalyst,[2] including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid.[3] 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.[4]

Aliquat 336 was used in the total synthesis of manzamine A by Darren Dixon in an early step to the electrophile.[5]


  1. ^ Litaiem, Yousra; Dhahbi, Mahmoud (2015). "Physicochemical Properties of an Hydrophobic Ionic Liquid (Aliquat 336) in a Polar Protic Solvent (Formamide) at Different Temperatures". Journal of Dispersion Science and Technology. 36 (5): 641. doi:10.1080/01932691.2013.862170.
  2. ^ C. M. Starks (1971). "Phase-transfer catalysis. I. Heterogeneous reactions involving anion transfer by quaternary ammonium and phosphonium salts". J. Am. Chem. Soc. 93: 195–199. doi:10.1021/ja00730a033.
  3. ^ 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.
  4. ^ Ameta, Suresh C; Ameta, Rakshit (2013-09-11). Green Chemistry: Fundamentals and Applications. ISBN 9781466578265.
  5. ^ 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. PMID 23039372.