Synthesis of surfactants from furfural derived 2[5H]-furanone and fatty amines

Furfural was oxidized to 2[5H]-furanone 2 using hydrogen peroxide. Furanone 2 was transformed with two equivalents of fatty amines. A condensation and a Michael reaction occurred. Ethyl bromoacetate 5 or methyl acrylate 6 were then added to the secondary amine function. Saponification of the ester function leads to amphoteric surfactants 8a,b,c and 10a,b,c possessing two n-alkyl chains as hydrophobic part. The resulting products can also be considered as Gemini surfactants or twin-tail amphoteric surfactants. Biodegradation studies have been performed on these compounds and the surfactant properties of 8a have been determined in detail.