Aldolisation of unprotected ketoses to surfactants

Biwen Zhu 1
1 CASYEN - Catalyse Synthèse et Environnement
ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
Abstract : In this manuscript, an atom economic route of C-C bond based surfactants has been developed. They are more stable for broader applications. This process involves the use of renewable and relatively low cost raw materials. Ketoses such as 1,3-dihydroxyacetone and D-fructose were used as substrates with aldehydes as alkylation agents without any protection-deprotection step. The synthesis has been divided into two steps, in the first step the deprotonated ketoses react with the aldehydes electrophiles to form the hydroxyketone intermediates. Then, a second step of hydrogenation with Ruthenium on alumina catalyst under hydrogen pressure gave access to the alkylated polyols. The overall yield of this two-step process is moderate considering the difficulty of reacting a highly hydrophobic part with a highly hydrophilic part. Then these tetraols adducts obtained with 1,3-dihydrdoxyacetone were also evaluated as surfactants by making physico-chemical tests (CMC, Krafft point and Phase Inverse Temperature). Results have exhibited this novel C-C bond connected surfactants perform as efficient as other commercially available surfactants in decreasing the surface tension which is a very attractive property for potential applications
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Biwen Zhu. Aldolisation of unprotected ketoses to surfactants. Other. Université de Lyon, 2018. English. ⟨NNT : 2018LYSE1153⟩. ⟨tel-01927348⟩

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