Oxidative dimerization of phenolic aldehydes related to lignin formation

Journal Article · Wed Mar 09 23:00:00 EST 1994 · Journal of Physical Chemistry; (United States)

DOI:https://doi.org/10.1021/j100061a022· OSTI ID:7267245

Hapiot, P; Pinson, J ^[1]; Francesch, C; Mhamdi, F; Rolando, C ^[2]; Neta, P ^[3]

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1. Laboratoire d'Electrochimie Moleculaire de l'Universite Paris (France)
2. Universite Pierre et Marie Curie, Paris (France)
3. National Inst. of Standards and Technology, Gaithersburg, MD (United States)

The first steps of the polymerization of phenolic aldehydes coumaraldehyde (1H), coniferaldehyde (2H), and sinapaldehyde (3H) have been examined by cyclic voltammetry and pulse radiolysis in aqueous (water/methanol mixture) and in organic solvents (acetonitrile and CH[sub 2]Cl[sub 2]). The mechanism involves an electron transfer of the corresponding phenolate to give the phenoxy radical which dimerizes. The values of the dimerization rate constants have been measured in water and acetonitrile (ACN) and found to be sensitive to the nature of the solvent. The standard potentials for the different phenoxyl radical/phenolate couples have been determined in the different solvents. 34 refs., 5 figs., 2 tabs.

• OSTI ID: 7267245
• Journal Information: Journal of Physical Chemistry; (United States), Journal Name: Journal of Physical Chemistry; (United States) Vol. 98:10; ISSN JPCHAX; ISSN 0022-3654
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
99 GENERAL AND MISCELLANEOUS
990200 -- Mathematics & Computers
ACETONITRILE
ALCOHOLS
ALDEHYDES
AQUEOUS SOLUTIONS
AROMATICS
CARBOHYDRATES
CHEMICAL RADIATION EFFECTS
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
COMPILED DATA
DATA
DECOMPOSITION
DIMERIZATION
DISPERSIONS
HYDROXY COMPOUNDS
INFORMATION
KINETICS
LIGNIN
MATHEMATICAL MODELS
METHANOL
METHYLENE CHLORIDE
MIXTURES
NITRILES
NUMERICAL DATA
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
OXIDATION
PHENOLS
PHENOXY RADICALS
POLYMERIZATION
POLYSACCHARIDES
RADIATION EFFECTS
RADICALS
RADIOLYSIS
REACTION KINETICS
SACCHARIDES
SOLUTIONS
VOLTAMETRY