Bio-based Aromatic Amines from Lignin-Derived Monomers
2019
Blondiaux, Enguerrand | Bomon, Jeroen | Smoleń, Michał | Kaval, Nadya | Lemière, Filip | Sergeyev, Sergey | Diels, Ludo | Sels, Bert | Maes, Bert U. W.
A new approach to synthesize valuable 3,4-dialkoxyanilines and alkyl propionates from lignin-derived 4-propylguaiacol and -catechol with overall isolated yields up to 65% has been described. The strategy is based on the introduction of nitrogen via a Beckmann rearrangement. Amino introduction therefore coincides with a C-defunctionalization reaction; overall a replacement of the propyl chain by an amino group is obtained. The process only requires cheap bulk chemicals as reagents/reactants and does not involve column chromatography to purify the reaction products. Furthermore, all carbon atoms from the biorenewable lignin-derived monomers are transformed into valuable compounds. Greenness was assessed by performing a Green Metrics analysis on two dialkoxyanilines. A comparison was made with literature routes for these compounds starting from a petrochemical substrate.
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