Alkaline cleavage of model lignin compounds
The alkaline cleavage of lignin models 2a-h, based upon 2-phenoxy-1-phenyl-1-propanol with electron-donating and -withdrawing groups on the phenoxy ring, proceeds through an internal displacement of the aryloxy group to provide an epoxide intermediate that opens to the glycol. The epoxide (2-methyl-3-phenyloxirane) was observed only after the alkaline cleavage of 2h, 2-(4-nitrophenoxy)-1-phenylpropanol, since the observed rate of disappearance of the epoxide is faster than that of all the lignin models except 2h. The observed rate of reaction was found to be sensitive to steric bulk and polar substituents in the ortho position of the aryloxy ring. Another product, 1-phenyl-2-propanone, is present in the product mixture, which suggests the occurrence of a concurrent pyrolysis mechanism. 13 refs., 1 fig., 1 tab.
- Research Organization:
- Pacific Northwest Lab., Richland, WA
- OSTI ID:
- 6437500
- Journal Information:
- Energy Fuel; (United States), Journal Name: Energy Fuel; (United States) Vol. 1:3; ISSN ENFUE
- Country of Publication:
- United States
- Language:
- English
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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201 -- Chemical & Physicochemical Properties
CARBOHYDRATES
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CLEAVAGE
CRYSTAL STRUCTURE
DECOMPOSITION
HYDROGEN COMPOUNDS
HYDROLYSIS
HYDROXIDES
KINETICS
LIGNIN
LYSIS
MICROSTRUCTURE
ORGANIC COMPOUNDS
OXYGEN COMPOUNDS
POLYSACCHARIDES
PYROLYSIS
REACTION KINETICS
SACCHARIDES
SOLVOLYSIS
THERMOCHEMICAL PROCESSES