A class of surfactants via PEG modification of the oleate moiety of lactonic sophorolipids: synthesis, characterisation and application

Abstract

There is ever increasing demand to develop surfactants based on sophorolipids because they are produced by non-pathogenic organisms, biodegradable and less toxic to humans and the environment. Herein, commercially available...

Synthesis, Characterization, and Physicochemical Performance of Nonionic Surfactants via PEG Modification of Epoxides of Alkyl Oleate Esters

“…A wide range of homogeneous and heterogeneous metal and non-metal Lewis acid catalysts were first screened at different reaction conditions: ytterbium(III) triflate, Yb(TFA) 3 ; indium(III) triflate, In(TFA) 3 ; iron(III) triflate, Fe(TFA) 3 ; scandium(III) triflate, Sc(TFA) 3 ; silica-supported boron trifluoride, Si-BF 3 ; boron trifluoride diethyl etherate, BF 3 -Et 2 O; sulfuric acid, H 2 SO 4 ; iron(III) chloride, FeCl 3 ; iron-exchanged montmorillonite clay, Fe-mont; aluminum-exchanged montmorillonite clay, Al-mont; and aluminum-exchanged zeolite clay, Al-zeolite. Most of these catalysts are less well known for this type of reaction. , The metal-exchanged montmorillonite catalysts were prepared as earlier reported. ,, …”

“…29,30 The metal-exchanged montmorillonite catalysts were prepared as earlier reported. 17,31,32 Results of catalyst screening (SI section 9.0 Table SI-4) showed that Si-BF 3 gave high selectivity toward the PEGylated oleate esters. Heterogeneous silica-supported BF 3 is corrosive but significantly less hazardous than its unsupported free form.…”

“…Other studies have reported epoxy ring opening of methyl and ethyl oleate epoxides with nucleophiles such as alkyl glycosides and oligoethene glycols using erbium(III) triflate and tin tetrachloride as catalysts. , However, these syntheses employed catalysts and solvents that present issues such as difficulty in removal and reuse of the catalyst, corrosiveness, and toxicity. Recently, functionalization of the double bond of the fatty ester unit of lactonic sophorolipid via epoxy ring opening with polyethylene glycols was demonstrated . The resulting surfactants gave promising results that could further be exploited in personal and home care products.…”

“…Recently, functionalization of the double bond of the fatty ester unit of lactonic sophorolipid via epoxy ring opening with polyethylene glycols was demonstrated. 17 The resulting surfactants gave promising results that could further be exploited in personal and home care products. A comprehensive list of the nucleophiles most commonly used to functionalize fatty derivatives, as well as the chemistry of fatty epoxide ring-opening reactions leading to valuable chemicals was recently reported by Moser and co-workers.…”

Ozonolysis of Symmetrical Bola Sophorosides Yields Key Precursors for the Development of Functional Sophorolipid Derivatives

“…While the enzymatic modifications are generally aimed at the regioselective modification of the SL’s sugar head, chemical modifications of SLs seem to provide more possibilities to increase the molecular variety and generate a library of SL derivatives. − For example, with respect to the chemical modification of SLs, Delbeke et al recently showed that lactonic SLs can be used as starting materials leading to the production of novel quaternary ammonium sophorosides (QASSs) . In addition to displaying antimicrobial properties, a number of the synthesized QASSs exhibited high transfection efficacies, showing that high-added-value applications may also be targeted within the SL platform. , The QASSs were produced from a C9:0 ω-1-sophoroside aldehyde precursor, which was obtained following an elaborate synthetic derivatization pathway.…”