Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
3D model (JSmol)
|Molar mass||404.16 g·mol−1|
|Appearance||Colorless viscous liquid|
|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|
|R-phrases (outdated)||R22 R38 R41 R50/53|
|S-phrases (outdated)||S26 S39 S60 S61|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)|
|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).
|what is ?)(|
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, including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. 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.
Aliquat 336 was used in the total synthesis of Manzamine A by Darren Dixon in an early step to the electrophile.
- 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.
- 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.
- 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.