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

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 lactonic sophorolipid was modified via epoxidation of the fatty acid units C...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2021-12, Vol.23 (24), p.9906-9915
Main Authors: Ogunjobi, Joseph K., McElroy, Con R., Clark, James H., Thornthwaite, David, Omoruyi, Osaretin E., Farmer, Thomas J.
Format: Article
Language:English
Subjects:
Acetic acid
Biodegradability
Biodegradation
Catalysis
Chemical synthesis
Detergents
Epoxidation
Ethyl acetate
Ethylene oxide
Fatty acids
Green chemistry
Lipophilic
Montmorillonite
Pollutants
Polyethylene glycol
Reaction time
Ring opening
Surfactants
Wetting
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Summary: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 lactonic sophorolipid was modified via epoxidation of the fatty acid units CC and subsequent ring-opening of the oxirane with poly(ethylene glycol) of vary chain lengths to deliver a novel range of non-ionic sophorolipid-based surfactants. The methods employed for ring-opening reaction lead to a final surfactant synthesis involving heterogeneous catalysis (metal-exchanged montmorillonite), use of a benign solvent (ethyl acetate) and short reaction time (60 minutes). The resulting surfactants were structurally characterised and a prediction of their potential applications achieved using the hydrophilic-lipophilic balance (HLB) concept, foam capacity and stability of the surfactants at 0.25% surfactant solution. This new family of bio-derivable non-ionic surfactants will be useful as wetting and solubilising agents, oil-in-water emulsifiers and detergents.
ISSN:1463-9262
1463-9270
DOI:10.1039/D1GC02247D