Exploration of mandelicacid‐basedpolymethacrylates: Synthesis, properties, and stereochemical effects

Abstract

Mandelic acid (MA) was utilized as a chiral biomass-based precursor to synthesize methacrylic monomers suitable for radical polymerization. A series of polymers were made that incorporated varying feeds of monomer stereopurity and the properties of these materials were investigated. High molar masses (>90 kg/mol) were achieved and the chirality in each polymer closely reflected the stereopurity of the monomer feeds. It was discovered that stereochemical effects had very little influence on the thermal and viscoelastic properties of the polymers produced, however, the steric bulk of the chiral pendants resulted in glassy, amorphous, and thermally stable materials with very low degrees of entanglement. The synthesis, thermal, and viscoelastic properties are discussed.

Stereoselective Reduction of Steroidal 4-Ene-3-ketones in the Presence of Biomass-Derived Ionic Liquids Leading to Biologically Important 5β-Steroids

“…4,5 One possibility to improve their green character is their synthesis from easily available, renewable resources. 6 Amino acids 7 available from proteins or natural carboxylic acids from biomass, such as Llactic acid, 8 L-malic acid, 9,10 or L-mandelic acid, 11 can serve as building blocks of greener ionic liquids. By using them as chiral solvents or additives, they present an opportunity to utilize chirality in synthetic procedures.…”

“…However, some ionic liquids or their degradation products are found to be toxic. , One possibility to improve their green character is their synthesis from easily available, renewable resources . Amino acids available from proteins or natural carboxylic acids from biomass, such as l -lactic acid, l -malic acid, , or l -mandelic acid, can serve as building blocks of greener ionic liquids. By using them as chiral solvents or additives, they present an opportunity to utilize chirality in synthetic procedures. , Hydrogenation reactions in ionic liquids are widely studied , as the immobilization of catalysts in ionic liquids facilitates the separation of the products and the recycling of the catalytic species.…”