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.

Applications

Organic Chemistry

Aliquat 336 is used as a phase transfer catalyst, including in the catalytic oxidation of cyclohexene to 1,6-hexanedioic acid. 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. Aliquat 336 was used in the total synthesis of manzamine A by Darren Dixon.

Solvent extraction of metals

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

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.