TY  - JOUR
U1  - Zeitschriftenartikel, wissenschaftlich - begutachtet (reviewed)
A1  - Jolmes, Tristan
A1  - Tayari, Siwar
A1  - Bresser, Marc
A1  - Müller, Sonja
A1  - Glüsen, Birgit
A1  - Schörken, Ulrich
T1  - Comparative Analysis of Bio-Based Amino Acid Surfactants obtained via Diels–Alder Reaction of Cyclic Anhydrides
JF  - Green Processing and Synthesis
N2  - 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.
KW  - Aminosäuren
KW  - Oberflächenspannung
KW  - Green Chemistry
KW  - Bio-Based Surfactants
KW  - Amino Acids
KW  - Antimicrobial Activity
KW  - Surface Tension
UN  - https://nbn-resolving.org/urn:nbn:de:hbz:832-epub4-26325
SN  - 2191-9550
SS  - 2191-9550
U6  - https://doi.org/10.1515/gps-2023-0140
DO  - https://doi.org/10.1515/gps-2023-0140
VL  - 2024
IS  - 1
SP  - 14
S1  - 14
PB  - De Gruyter
ER  -