Download PDF
Synfacts 2019; 15(07): 0779
DOI: 10.1055/s-0039-1689751
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Co-Synthesis of Glycolic Acids, Formamides, and Formates on Copper/Alumina

Contributor(s):
Yasuhiro Uozumi
,
Shun Ichii
Dai X, Adomeit S, Rabeah J, Kreyenschulte C, Brückner A. * Wang H, Shi F. * Lanzhou Institute of Chemical Physics and University of Chinese Academy of Sciences, Beijing, P. R. of China; Leibniz-Institut für Katalyse e.V. an der Universität Rostock (LIKAT), Germany
Sustainable Co-Synthesis of Glycolic Acid, Formamides and Formates from 1,3-Dihydroxyacetone by a Cu/Al2O3 Catalyst with a Single Active Sites.

Angew. Chem. Int. Ed. 2019;
58: 5251-5255
CrossrefPubMedSearch in Google Scholar
Further Information

Publication History

Publication Date:
17 June 2019 (online)

 
 PDF Download Permissions and Reprints

Key words

copper catalysis - formates - dihydroxyacetone - glycolic acid - formylation - formamides

Significance

An alumina-supported copper catalyst (Cu/Al2O3) was prepared by mixing copper(II) chloride with alumina, followed by calcination (eq. 1). Cu/Al2O3 catalyzed the oxidative degradation of 1,3-dihydroxyacetone with hydrogen peroxide in water to give glycolic acid in 91% yield with co-production of formic acid (eq. 2). The reaction also proceeded in the presence of amines or alcohols to afford the corresponding formamides or formates as co-products in 70–99% yield (eq. 3).


#

Comment

In the oxidation of 1,3-dihydroxyacetone, Cu/Al2O3 was recovered by centrifugation and reused twice without loss of its catalytic performance (fresh: 91% yield; third run: 88%). ICP analyses and a filtration test suggested that the reaction proceeds heterogeneously. XRD, HAADF-STEM, and N2 adsorption–desorption experiments on the reused catalyst showed no obvious changes in its structure.


#
#


   Permissions and Reprints