期刊
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
卷 7, 期 7, 页码 6906-6916出版社
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.8b06467
关键词
Anilines; Biorenewable chemicals; Benzylic oxidation; Beckmann rearrangement; Green Metrics; Bioaromatics
资金
- VLAIO/Catalisti (ARBOREF)
- UAntwerpen (BOF)
- Hercules Foundation
- Research Foundation Flanders (FWO) (WOG and BioFact Excellence of Science project) [30902231]
- BIO-HArT project
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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