Short chain glycerol 1-monoethers—a new class of green solvo-surfactants

Abstract

The synthesis of short eco-friendly amphiphilic compounds derived from glycerol was carried out. These compounds, called solvo-surfactants, are of great interest since they exhibit both properties of solvents, e.g. volatility, solubilization of organics, and surfactants, e.g. reduction of interfacial tensions, formation of emulsions and microemulsions. Their surface activity was studied, and binary phase diagrams with water were drawn. Their sensitivity to various electrolytes from Hofmeister's series was also investigated. Short chain glycerol 1-monoethers constitute a new class of green solvo-surfactants with excellent properties, that should be seriously considered for the replacement of reprotoxic glycol ethers. They have, moreover, the advantage of helping to solve the problem of an over-production of glycerol, which is a major side-product of the biocarburant industry.

Etherification of glycerol with benzyl alcohol catalyzed by solid acids

“…Glycerol ethers have many potential uses, such as fuel additives, 12 solvents, 13 cryogenics, 14 and anti-bacterial agents. 15 Reactions of glycerol with isobutene 16 or tertbutanol 17 under acid catalysis conditions afford tert-butylglycerol ethers, which have potential for blending with diesel.…”

Classification of Organic Solvents Revisited by Using the COSMO‐RS Approach

“…[34] Such result was unexpected as propylene glycol and 1,4-dioxane are two low-polymer affinity solvents. The COSMO-RS s-potential approach may rationalise these experimental observations.…”

“…Solubility data of nitrocellulose (of type H23, A. Hagedorn & Co) in numerous solvents has been reported by Hansen, [33,34] eighty of them being included in the dataset of the present classification shown in Table 1. Hansen used the following protocol: Nitrocellulose (0.5 g) was immersed in 5 mL of solvent and the solubilisation was qualitatively scored from 1 (total solubilisation) to 6 (no noticeable change).…”

“…[32][33][34] This active research area stimulates the development of theoretical descriptor-based classifications since they offer the possibility to evaluate in silico the properties of potential new solvents, prior to any synthetic work. These a priori methods allow consequently the screening of a great deal of virtual solvents and the selection of the most promising candidates for any specific application.…”

Oxygenated Glycerol Derivatives as an Alternative Source of Energy: A Review

“…Glycerol alkyl ethers can be synthesized as described by Williamson 21,22 , though a bimolecular nucleophilic substitution of alkyl halide with alkoxide ions (S N 2). Another acceptable process for ether formation is etherification with an alcohol or olefin in the presence of an acid catalyst 23 .…”