Acylation of unprotected lactose with 1,18‐octadec‐9‐enedioyl chloride for the synthesis of monocatenary and bolaform agro‐based surfactants

Abstract

Agro‐based surfactants have one of two hydrophilic or hydrophobic parts of vegetable origin. They can be produced from renewable and readily available resources. Carbohydrate fatty acid esters are non‐toxic, non‐ionic, and biodegradable agro‐based surfactants with applications in the pharmaceutical, cosmetic, and food industries. In this work, the chemical synthesis of agro‐based surfactants through lactose acylation with 1,18‐octadec‐9‐enedioyl chloride (Acyl‐Cl) was investigated at room temperature. The acylation reaction proved to be regioselective to the primary hydroxyl group of the glucose‐moiety in the lactose molecule and was promoted by an excess of lactose to produce higher substituted derivatives. Acyl‐Cl conversion was ∼98 % after 1 h of reaction. The production of monocatenary agro‐based surfactant, mono‐lactose 1,18‐octadec‐9‐enoate, was favoured with a molar ratio lactose/Acyl‐Cl of 1 achieving a yield of 48 % after 20 min. Moreover, production of bolaform agro‐based surfactant, di‐lactose 1,18‐octadec‐9‐enedioate, was favoured with a molar ratio of 3 lactose/Acyl‐Cl with a yield of 33 % after 1 h of reaction. A one‐pot synthesis of agro‐based bolaform surfactant was successfully achieved for the first time in the open literature. Monocatenary and bolaform agro‐based surfactants were isolated by preparative liquid chromatography with high purity according to their chemical structure identification by liquid chromatography coupled to mass spectrometry and 1H nuclear magnetic resonance. Their critical micellar concentration (12–9 μM) determined by fluorescence spectroscopy with pyrene used as a probe, and hydrophilic:lipophilic balance values (10.7–14.2) indicated that monocatenary and bolaform agro‐based surfactants can act as oils in water emulsion.

Synthesis and Characterization of a New Organocatalytic Biosourced Surfactant

“…The average diameter was 158.0 ± 0.4 nm, which is highly likely due to the filtration which eliminated the biggest aggregates. This size of aggregates is more typical of the formation of vesicles, [46] which are generally obtained with bolaform surfactants [47,48]. Compound 1 can be actually considered as bolaform as it has hydrophilic groups at both ends of the hydrophobic hydrocarbon chain.…”

Effect of Amphiphilic CaCO3 Nanoparticles on the Plant Surfactant Saponin Solution on the Oil–Water Interface: A Feasibility Research of Enhanced Oil Recovery

“…13−15 Surfactants can reduce the oil−water interface tension to increase the efficiency of oil washing. 16−20 Meanwhile, the molecule structure of surfactants has lipophilic groups and hydrophilic groups, 21 which can emulsify oil and water into the single-phase emulsion. 22,23 If the emulsion is the O/W emulsion, it can reduce the viscosity of crude oil, improve the water−oil mobility ratio, and expand the sweep volume.…”

“…In chemical flooding, surfactant flooding is a kind of chemical flooding method which has wide fitness for purpose and development potential. − Surfactants can reduce the oil–water interface tension to increase the efficiency of oil washing. − Meanwhile, the molecule structure of surfactants has lipophilic groups and hydrophilic groups, which can emulsify oil and water into the single-phase emulsion. , If the emulsion is the O/W emulsion, it can reduce the viscosity of crude oil, improve the water–oil mobility ratio, and expand the sweep volume. , Conversely, if the emulsion belongs the W/O emulsion, it can form a stable front to expand the sweep volume . In addition, the emulsion can plug large pores owing to the “Jamin effect”, resulting in the subsequent fluid divert into the low permeability zones to enhance oil recovery. , However, the emulsion system is very unstable owing to the imbalance of the interaction force between the surfactant and the oil–water phase, and the emulsion is extremely easy to be destroyed under the influence of gravity and temperature, resulting in the separation of oil and water .…”

A Journey across Food & Chemical Engineering Dyad: Symposium in memory of Professor Khaled Belkacemi

“…The second topic picked up a couple of biotechnology applications (enzyme immobilization on magnetic nanoparticles and cell adhesion on collagen scaffolds). The third one accrued agri‐food and plant valorization contributions (free‐radical anthocyanin oxidation, synthesis of agro‐based surfactants, rare‐earth toxicity in horticultural plants, and extraction of cereal wax‐like components). Finally, the fourth topic included contributions on a few aqueous‐based environmental and mineral processing methods (methyl violet by low‐cost waste, chromium sunlight photocatalytic reduction, and gold dissolution from silver‐bearing sulphide mineral ores).…”