Highly Selective Mitsunobu Esterification of Cellulose with Hydroxycinnamic Acids

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

  • Thomas Elschner - , Dresden University of Technology (Author)
  • Erica Brendler - , Freiberg University of Mining and Technology (Author)
  • Steffen Fischer - , Dresden University of Technology (Author)

Abstract

Cellulose esters of hydroxycinnamic acids, namely ferulic-, p-coumaric-, and caffeic acid, are synthesized by Mitsunobu esterification applying triphenylphosphine and diisopropyl azodicarboxylate in N,N-dimethylacetamide/LiCl. The reaction is found to be highly selective and took place at primary hydroxyl groups at position 6 of cellulose without undesired conversion of double bonds and phenolic hydroxyl groups. Molecular structure characterization is performed by FTIR- and NMR spectroscopy. The products are soluble in dimethyl sulfoxide and possessed degree of substitution (DS) values of up to 0.5. DS values are determined by two independent methods, namely H-1 NMR spectroscopy of peracetylated derivatives and UV spectroscopy of extracted ferulic acid. The synthesis of cellulose hydroxycinnamates is very important to design lignocellulosic model systems and antioxidative bioinspired materials.

Details

Original languageEnglish
Article number2100232
Number of pages6
JournalMacromolecular chemistry and physics : MCP
Volume222
Issue number21
Publication statusPublished - Nov 2021
Peer-reviewedYes
Externally publishedYes

External IDs

Scopus 85116830984

Keywords

Keywords

  • cellulose, ferulic acid, hydroxycinnamate, Mitsunobu reaction, selective esterification, ANTIOXIDANT ACTIVITY EVALUATION, FERULIC ACID