| Publication Type |
Journal Article |
| Title |
Biomass-Based and Oxidant-Free Preparation of Hydroquinone from Quinic Acid |
| Authors |
Benedicta Assoah Luis F. Veiros Carlos A. M. Afonso Nuno R. Candeias |
| Groups |
IOARC |
| Journal |
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY |
| Year |
2016 |
| Month |
August |
| Volume |
|
| Number |
22 |
| Pages |
3856-3861 |
| Abstract |
A biomass-based route to the preparation of hydroquinone starting from the renewable starting material quinic acid is described. Amberlyst-15 in the dry form promoted the one-step formation of hydroquinone from quinic acid in toluene without any oxidants or metal catalysts in 72 \% yield. Several acidic polymer-based resins and organic acids as promoters as well as a variety of reaction conditions were screened including temperature, concentration and low- and high-boiling-point solvents. A 1: 4 (w/w) ratio of quinic acid/Amberlyst-15 was determined to be optimal to promote hydroquinone formation with only traces of a dimeric side-product. A mechanism has been proposed based on the decarbonylation of protonated quino-1,5-lactone that is supported by experimental and computational calculation data. |
| DOI |
http://dx.doi.org/10.1002/ejoc.201600616 |
| ISBN |
|
| Publisher |
WILEY-V C H VERLAG GMBH |
| Book Title |
|
| ISSN |
1434-193X |
| EISSN |
1099-0690 |
| Conference Name |
|
| Bibtex ID |
ISI:000382768400026 |
| Observations |
|
