Phenoxy‐Alkyl Maleates as Phase‐Selective Organogelators for Gelation of Edible Oils

Abstract

Phase selective gelation may solve environmental problems such as water pollution and fire accidents during oil storage, a major problem for aquatic bodies. The objective of this work is to synthesize a series of phenoxy‐alkyl maleates (n‐PAM) oleogelators with homologous alkyl chain lengths for efficient phase selective gelation. The n‐PAM molecules are found to form oleogel in various edible oils among which sunflower oil shows best gelation. The gelation behavior increases with an increase in alkyl chain length of the n‐PAM gelators as observed from their low minimum gelation concentration (MGC) values. Oleogels thermal stability is examine through tube inversion method and differential scanning calorimetry (DSC). The rheological studies suggest that the oleogel of sunflower oil is mechanically stable and show typical viscoelastic properties. The field emission scanning electron microscopy (FE‐SEM) study of the gels shows sheet‐like morphology. Furthermore, the n‐PAM gelators exhibit quick phase selective gelation of edible oils at low MGC. Both the edible oil and gelator are quantitatively regained from recovered oleogel by employing the vacuum distillation. It is believed that these n‐PAMs could aid in reducing the environmental impacts of oil spills. Practical Applications: The phenoxy‐alkyl maleates gelators present in the MS show gelation ability in various edible oils at low minimum gelation concentration. These molecules also form efficient phase selective gelation with edible oils. Both oil and gelator can be recovered through vacuum distillation and gelator can be reused multiple times. Thus, all these advantages strongly point that out their bright future, in particular in edible oil spill recovery, could aid in reducing the environmental impacts from oil spills. Herein, the synthesized phenoxy alkyl maleate derivatives are reported as separators of edible oil from the oil‐water biphasic mixture. Initially, the gelator is solubilized in the biphasic mixture by heating. Later, gelation ability is observed by tube inversion method. From the phase selective gel, oil and gelator are separated through a distillation method. The recovered gelator can be reused in oil recovery process. This application may find use in oil recovery from waste plant of edible oil industries.

Supramolecular Glycolipid-Based Hydro-/Organogels with Enzymatic Bioactive Release Ability by Tuning the Chain Length and Headgroup Size

“…It can be observed in Figure i that G ′ was higher in magnitude than G ″ within the experimental frequency range. This indicates the prominent gel characteristic of the sample . The maximum tolerance, i.e., “maximum independent frequency ( f )” value of organogels, displayed a similar trend as observed for the value (Table ).…”

“…This indicates the prominent gel characteristic of the sample. 46 The maximum tolerance, i.e., "maximum independent frequency (f)" value of organogels, displayed a similar trend as observed for the value (Table 2). For hydrogels (16M-W and 22M-W), the f value increased with an increase in chain length.…”

Effect of oil unsaturation and wax composition on stability, properties and food applicability of oleogels

“…Various studies have been performed which include formation of oleogels by using monoglycerides in combination of wax (da Silva et al, 2018;Yılmaz & Ö gütcü, 2014), hydroxypropylmethylcellulose, sodium caseinate with beeswax in vegetable oils (Alizadeh et al, 2020), beeswax and β-sitosterol in sunflower oil etc. Several peptide-based (Guchhait & Roy, 2019) and phenoxyalkyl maleate based oleogelator (Kumar & Nayak, 2019) has also been introduced for phase selective gelation with application in edible oil spill recovery.…”

Harnessing Glycolipids for Supramolecular Gelation: A Contemporary Review

“…Glycolipid-derived supramolecular gels find diverse applications in soft optical devices, CO 2 absorption, lectin binding, oil spill recovery, and the sequestration of alkali metal ions. 7,154 These amphiphilic organo/hydrogels possess the capability to encapsulate hydrophilic/hydrophobic drugs within their selfassembled 3D networks, thereby enabling controlled release of bioactives. 31,155 Hydrogels and gel emulsions exhibit versatile applications in the preparation of food gels by demonstrating several characteristics.…”

“…Generally, there are two main types of gelators, i.e., polymers and small molecules. Molecular gels formed by small organic compounds are termed as low-molecular-weight gelators (LMWGs). − Formation of a 3D gel network by LMWG includes noncovalent interactions, such as electrostatic interactions, van der Waals interactions, hydrogen bonding, π–π stacking, etc., and the resultant gel is known as a “supramolecular gel.” LMWGs have a molecular mass less than 3000 Da. Depending upon the polarity of the solvent used, LMWGs can be further classified into two classes: (a) low-molecular-weight organogelators (LMOGs), which entrap organic solvents, and (b) low-molecular-weight hydrogelators (LMHGs), which entrap water.…”