Aliquat 336
Template:Hembox Identifiers
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| Names | |
|---|---|
| IUPAC name
N-Methyl-N,N-dioctyloctan-1-ammonium chloride
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| Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
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| Properties | |
| C25H54ClN | |
| 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 |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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Toxic (USA) |
| Flash point | 113 °C (closed cup) |
| Related compounds | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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[citation needed] or potassium permanganate[citation needed], which produce hazardous wastes.
References
- ^ 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. Ed. 77 (12): 1627–8. doi:10.1021/ed077p1627.