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]
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| Names | |
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| IUPAC name
N-Methyl-N,N,N-trioctylammonium chloride
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| Other names
Starks' catalyst; Tricaprylmethylammonium chloride, Methyltrioctylammonium chloride
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.023.542 |
PubChem CID
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CompTox Dashboard (EPA)
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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) |
| GHS labelling: | |
   
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| Danger | |
| H301, H315, H318, H319, H410 | |
| P264, P270, P273, P280, P301+P310, P302+P352, P305+P351+P338, P310, P321, P330, P332+P313, P337+P313, P362, P391, P405, P501 | |
| Flash point | 113 °C (235 °F; 386 K) (closed cup) |
| Safety data sheet (SDS) | External MSDS |
| Related compounds | |
Related
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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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Applications edit
Organic Chemistry edit
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 an example of green chemistry, as it is more environmentally friendly than 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.[5]
Solvent extraction of metals edit
Aliquat 336 has been used for the extraction of metals by acting as a liquid anion exchanger. It is commonly used as a solution in hydrocarbon solvents such as aromatic kerosene. Aliphatic kerosene can also be used, but requires the addition of a phase modifier (typically a long chain alcohol) to prevent the formation of third phase.
Waste treatment edit
Several applications have been successfully carried out with Aliquat 336, such as the recovery of acids or acid salts, or the removal of certain metals from wastewater. In addition, foaming has also been controlled by using this agent during the treatment of wastewater containing anionic surfactants.
References edit
- ^ 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. S2CID 95868263.
- ^ 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.
- ^ 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.
- ^ Ameta, Suresh C; Ameta, Rakshit (2013-09-11). Green Chemistry: Fundamentals and Applications. CRC Press. ISBN 9781466578265.
- ^ 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.