| Description | Methyltrioctylammonium chloride is a water insoluble quaternary ammonium salt, which is widely used as a counter ion in solvent extraction of anionic metal complexes. It is widely used as a phase transfer catalyst for the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. In comparison to traditional method of oxidizing cyclohexanol or cyclohexanone with nitric acid or potassium permanganate, the usage of methyltrioctylammonium chloride is a more environmentally friendly reaction. |
| Reference | N. Pourreza, H. Zavvar Mousavi, Determination of cadmium by flame atomic absorption spectrometry after preconcentration on naphthalene– methyltrioctylammonium chloride adsorbent as tetraiodocadmate (II) ions, Analytica Chimica Acta, 2004, vol. 503, pp. 279-282
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| Chemical Properties | viscous colourless to pale orange liquid |
| Uses | Methyltrioctylammonium chloride can be used:
- As a catalyst in the synthesis of acridine dione derivatives from aromatic aldehyde, dimedone and amines under ultrasonic irradiations.
- As a catalyst in the synthesis of extended π-systems using aromatic aldehydes and methyldiazines.
- As a component of a catalytic system used in the Suzuki-Miyaura cross-coupling reaction of a variety of aryl and heteroaryl chlorides in H2O.
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| Uses | Mixture of C8 and C10 chains with C8 predominating. Used as a metal extraction reagent and a phase-transfer catalyst. |
| Definition | ChEBI: An organic chloride salt having methyltrioctylammonium as the cation. |
| Flammability and Explosibility | Notclassified |
| Safety Profile | Poison by ingestion and
intraperitoneal routes. When heated to
decomposition it emits very toxic fumes of
NOx, NH3, and Cl-. |
| Purification Methods | A 30% (v/v) of Aliquat 336 solution in *benzene is washed twice with an equal volume of 1.5M HBr. [Petrow & Allen, Anal Chem 33 1303 1961.] It is purified by dissolving 50g in CHCl3 (100mL) and shaking with 20% NaOH solution (200mL) for 10minutes, and followed by 20% NaCl (200mL) for 10minutes. It is then washed with a small volume of H2O and filtered through a dry filter paper [Adam & Pribil Talanta 18 733 1971]. n-Alkylammonium chloride n=2,4,6. Recrystallise them from EtOH or an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985, Chu & Thomas J Am Chem Soc 108 6270 1986.] n-Alkyltrimethylammonium bromide n=10,12,16. Recrystallise them from an EtOH/Et2O mixture. [Hashimoto & Thomas J Am Chem Soc 107 4655 1985.] |
