期刊
ACS CATALYSIS
卷 7, 期 10, 页码 7363-7370出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b02348
关键词
reductive etherification; 5-hydroxymethyl furfural; furfuryl alcohol; furfural; metal chloride
资金
- Catalysis Center for Energy Innovation, an Energy Frontier Research Center - US Dept. of Energy, Office of Science, Office of Basic Energy Sciences [DE-SC0001004]
- National Institute of General Medical Sciences of the National Institutes of Health [P20GM104316]
Metal chlorides are demonstrated to behave as bifunctional acid catalysts in organic media in the one-pot reductive etherification of 5-hydroxymethylfurfural (HMF) in 2-propanol toward production of biodiesel. Two competing reaction pathways, direct etherification to 5(isopropoxymethyl)furfural and reductive etherification to 2,5-bis(isopropoxymethyl)furan, are proposed with the selectivity depending on the metal ion. Furfural and furfuryl alcohol are used as model compounds to investigate each pathway individually. The roles of Lewis/Bronsted acidity of metal chlorides solution are elucidated by kinetic studies in conjunction with salt speciation using electrospray soft ionization mass spectrometer. Bronsted acidic species, generated from alcoholysis of the metal chlorides, are the predominant catalytically active species in etherification. On the other hand, partially hydrolyzed metal cations produced by alcoholysis/hydrolysis are responsible Lewis acid centers for furfural reduction to furfuryl alcohol. Isotopic labeling experiments, in combination with GCMS and H-1 NMR analysis, reveal an intermolecular hydrogen transfer from the alpha-C of 2-propanol to the alpha-C of furfural as the rate-limiting step of furfural hydrogenation.
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