Reactive Epoxy Nanofiltration Membranes with Disulfide Bonds for the Separation of Multicomponent Chemical Mixtures

Abstract

This article reports the fabrication of organic solvent nanofiltration membranes containing a labile disulfide bond, which is broken by reaction with a chemical stimulus. These membranes are a new generation of smart membranes that have tailored selectivities and flux that can be altered by reacting with a chemical stimulus. The selectivity and flux of chemicals through the membranes was controlled by varying the concentration of disulfide bonds in the membrane. When the disulfide bonds were cleaved, the pores in the membrane became larger and yielded different separation properties. The membrane selectivity was changed by up to 70% and flux was increased up to 5×. The rapid change in selectivity of the membrane allowed for the separation of three-component mixtures. A three-component mixture of 33.3% m-dinitrobenzene, 33.3% triphenylmethane, and 33.3% 1,3,5-tris(diphenylamino)benzene (TDAB) was separated into three different fractions that were significantly enriched in one of the three molecules. The first fraction contained m-dinitrobenzene at 82% purity and 84% yield, the second fraction contained triphenylmethane at 67% purity and 49% yield, and the third fraction contained TDAB at 71% purity and 88% yield.

Welding and reprocessing of disulfide‐containing thermoset epoxy resin exhibiting behavior reminiscent of a thermoplastic

“…The epoxidation was confirmed by CO stretching of oxirane ring at approximately 912 cm −1 in the spectrum of BGPDS. [ 33,34 ] The appearance of CS vibration at approximately 1,493 cm −1 indicated the presence of disulfide groups attached to the aromatic ring in both spectra, showing that the disulfide bonds were stable during the epoxidation reaction.…”

Advanced stimuli-responsive membranes for smart separation

“…In this study, Gilmer et al fabricated novel epoxy nanofiltration membranes via one-pot homogeneous polymerization between diepoxide and dianilines containing disulfide bonds. 181 Disulfide bonds are able to cleave in the presence of chemical stimuli such as cysteamine, which increases pore size and consequently affects the separation performances. This membrane was used to separate three-component mixtures, and three different fractions enriched in one of the three molecules were obtained.…”

Nonlinear Flux–Pressure Behavior of Solvent Permeation through a Hydrophobic Nanofiltration Membrane

“…Edible oil processing is the third-largest food-processing sector in the world; ∼73 MMT of vegetable oil is produced through solvent extraction, which consumes a relatively large amount of energy for solvent recovery in the oil extraction process. Organic solvent nanofiltration (OSN) is a potential alternative to conventional evaporation, − which focuses on separating nonaqueous systems without a phase change by employing solvent-resistant nanofiltration (SRNF) membranes. Therefore, it is imperative to understand the transport mechanism of solvents in SRNF membranes to predict their performance and for induction in the intended process step.…”