Cedric Ernenwein

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.

Low Catalyst Loadings for the Production of Carboxylic Acids from Polysaccharides and Hydrogen Peroxide

The oxidation of starch, xylans, potato flesh and wheat flour by H(2)O(2), in the presence of MSO(4) (M=Cu, Fe) as catalyst, led to depolymerization, and formation of solutions containing polyhydroxycarboxylic acids. Some of these oxidized compounds facilitate the process, leading to efficient transformations even with very low amounts of catalyst.

Sulfonated surfactants obtained from furfural

Furfural obtained from pentose containing biomass such as hemicelluloses is subjected to photooxygenation. The resulting hydroxyfuranone obtained in high yields undergoes acetalization with fatty alcohols. Using NaHSO3, surfactants are obtained by addition of a sulfonate group to α,β-unsaturated carboxyl or carbonyl compounds. Addition occurred either at the CC double bond (6) or at the aldehyde function (7). Compared to conventional surfactants of this type, the resulting compounds possess similar good detergent properties. In the case of compound family 6 and when compared to the corresponding alkylsulfate and alkylsulfonate surfactants, even lower critical micelle concentrations (CMC) are observed. Biodegradation of the new surfactants was determined according to the OECD Test guideline 301 F. Compounds of family 6 are biodegradable. Biodegradation of compounds of family 7 stopped after 10 days.

Mapping and Multivariate Analysis for a Rapid Evaluation of New Green Solvents Characteristics and Efficiency

Current regulations require the substitution of toxic solvents by safer ones. Succinic acid diesters, which are among promising bio-based candidates, have been compared to petrochemical solvents through two complementary approaches. The first one deals with a prediction of solvents dissolution power based on Hansen Solubility Parameters (HSP). HSP values obtained with the model developed by Stefanis-Panayiotou showed good agreement with experimental miscibility maps. The second one explores the physicochemical properties with multivariate statistical methods. Principal Components Analysis and Agglomerative Hierarchical Clustering led to a partition of green solvents into clusters together with toxic solvents, suggesting favourable substitutions in further applications.