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Comparative Analysis of Bio-Based Amino Acid Surfactants obtained via Diels–Alder Reaction of Cyclic Anhydrides

  • Current changes in environmental legislation and customer demands set an urge for the development of more sustainable surfactants. Thus, the objective of this work was the development of novel environmentally friendly amino acid surfactants. Combining Diels–Alder cyclization of myrcene with maleic or citraconic anhydride followed by ring opening with amino acids enabled a synthesis route with a principal 100% atom economy. Variation of amino acids resulted in a large structural variety of anionic and amphoteric surfactants. Lysine gave access to either a mono-acylated product bearing a cationic side chain or a bi-acylated gemini surfactant. First, anhydride precursors were synthesized in yields of >90% in a Diels–Alder reaction under microwave radiation and subsequent amino acid coupling in aqueous environment gave fully bio-based surfactants in good yields and purity. Physicochemical characterization showed an enhanced decrease in surface tension upon addition of amino acids to the myrcene–anhydride backbone, resulting in a minimal value of 31 mN·m−1 for gemini–lysine. Foamabilitiy and foam stability were significantly increased at skin-friendly pH 5.5 by incorporation of amino acids. The carboxylic groups of surfactants with arginine were esterified with ethanol to access cationic compounds. Comparative analysis revealed moderate antimicrobial effects against yeast, Gram-positive bacteria, and Gram-negative bacteria.
Metadaten
Author:Tristan Jolmes, Siwar Tayari, Marc Bresser, Sonja Müller, Birgit Glüsen, Ulrich Schörken
URN:urn:nbn:de:hbz:832-epub4-26325
DOI:https://doi.org/10.1515/gps-2023-0140
ISSN:2191-9550
Parent Title (English):Green Processing and Synthesis
Descirption of the primary publication:09.02.2024
Publisher:De Gruyter
Document Type:Article
Language:English
Date of Publication (online):2024/02/29
GND-Keyword:Aminosäuren; Oberflächenspannung
Tag:Amino Acids; Antimicrobial Activity; Bio-Based Surfactants; Green Chemistry; Surface Tension
Volume:2024
Issue:1
Article Number:20230140
Page Number:14
Institutes:Angewandte Naturwissenschaften (F11)
Dewey Decimal Classification:500 Naturwissenschaften und Mathematik
Open Access:Open Access
OA-Publicationfonds TH Köln:OA-Publicationfonds TH Köln
Licence (German):License LogoCreative Commons - CC BY - Namensnennung 4.0 International