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Cao, Jun, et al. Journal of cleaner production 152 (2017): 399-405.
Methyl trioctyl ammonium chloride (MTOAC) has been successfully employed as a key quaternary ammonium salt for the preparation of a hydrophobic deep eutectic solvent (DES) tailored for the efficient extraction of polyprenyl acetates from Ginkgo biloba leaves. In this study, a ternary DES, named MCO, was formulated by combining MTOAC with capryl alcohol and octylic acid at an optimized molar ratio of 1:2:3. The DES was designed to leverage the tunable hydrophobicity and hydrogen-bonding interactions provided by the ammonium cation and the selected hydrogen-bond donors, thereby enhancing solubilization of target bioactive compounds.
The extraction performance of MCO was systematically optimized using statistical methods, including response surface methodology, to identify the ideal operational parameters. Under these optimized conditions, an extraction yield of 84.11 ± 0.7366% was achieved, significantly surpassing conventional organic solvents such as petroleum ether and n-hexane. Furthermore, the polyprenyl acetates could be efficiently recovered from the MCO solution using macroporous resins (AB-8 or DM130), demonstrating the feasibility of a green, recyclable extraction process.
This work illustrates the critical role of methyl trioctyl ammonium chloride in hydrophobic DES formation, enabling the development of environmentally friendly, high-performance solvents for bioactive compound extraction. Its incorporation not only enhances extraction efficiency but also facilitates the design of tailor-made DESs for sustainable utilization of plant biomass, highlighting its potential in green chemistry applications for pharmaceutical and nutraceutical industries.
Ma, Shaoping, et al. Journal of Molecular Liquids 319 (2020): 114106.
Methyl trioctyl ammonium chloride (MTOAC) has been successfully applied as a hydrogen-bond acceptor in the design of hydrophobic deep eutectic solvents (DESs) for enantioselective liquid-liquid extraction (ELLE) of tryptophan enantiomers. In this study, a biphasic recognition chiral extraction (BRCE) system was constructed using MTOAC in combination with L(+)-diethyl L-tartrate (DE) as a hydrogen-bond donor and paired with a hydrophilic DES (HP-β-CD-L-(-)-malic acid) to establish the MTAC-DE/HC-MA system. This dual DES-based system simultaneously acted as the phase-forming component and chiral selector, eliminating the need for additional chiral agents.
Optimization of the HBA:HBD molar ratio revealed that a 1:2 ratio of MTOAC to DE maximized enantiomeric excess (e.e.) to 38.46% for L-tryptophan in one-step extraction. The enantioseparation efficiency was further influenced by phase volume ratio, initial substrate concentration, pH, and extraction temperature. Mechanistically, increasing DE enhanced selective partitioning of L-Trp into the hydrophobic phase, whereas excess DE promoted migration into the hydrophilic phase, reducing e.e. values.
This application demonstrates the versatility of methyl trioctyl ammonium chloride as a tunable component in hydrophobic DESs for green, efficient, and high-performance chiral separations. Its integration into the BRCE system offers a simple operational procedure with high potential for continuous enantioseparation processes, providing an environmentally friendly alternative to conventional chiral extraction methods and highlighting its promise in pharmaceutical and biochemical applications.
Dalali, N., H. Yavarizadeh, and Y. K. Agrawal. Journal of Industrial and Engineering Chemistry 18.3 (2012): 1001-1005.
Trioctyl methyl ammonium chloride (Aliquat 336) has been effectively employed as a carrier for the selective transport of Cd(II) and Zn(II) ions from aqueous sodium chloride solutions through a bulk liquid membrane (BLM) system. In this study, Aliquat 336 (0.03 M) dissolved in benzene acted as the membrane phase, facilitating ion transfer between the source and receiving aqueous phases under mild room temperature conditions (20 ± 0.2 °C). The system enabled high transport efficiencies, achieving 93.0 (±0.5)% for Cd(II) and 80.0 (±0.7)% for Zn(II) within 5 h, demonstrating significant selectivity toward cadmium ions.
Key parameters influencing transport performance, including chloride concentration, carrier concentration, organic solvent type, and receiving phase composition, were systematically optimized. EDTA (0.3 M) or NH₃ (4 M) solutions served as effective receiving phases, promoting quantitative metal recovery. The BLM system was validated using real-world samples, including zinc plant purification cake and spent Ni-Cd batteries, illustrating its practical applicability for metal recovery. Mechanistically, the quaternary ammonium cation in Aliquat 336 forms lipophilic complexes with metal-chloride species in the feed solution, enabling selective extraction and migration through the organic membrane layer.
This study highlights the utility of trioctyl methyl ammonium chloride as a highly efficient and selective extractant for heavy metal ions, providing a reproducible, environmentally favorable approach for recovery and separation of Cd(II) and Zn(II) from industrial waste streams. Its incorporation into BLM systems offers significant advantages in terms of operational simplicity, high selectivity, and scalability for hydrometallurgical applications.
