Journal
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
Volume 5, Issue 11, Pages 9818-9825Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acssuschemeng.7b01725
Keywords
Oxidation; Lignin; Vanadium; Copper; Kinetics
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Funding
- Cluster of Excellence Tailor Made Fuels from Biomass (TMFB) - Excellence Initiative of the German federal government
- Spanish Ministry of Science and Innovation [Prometeo 11/203/011, SEV2012-0267]
- NRW Graduate School BrenaRo
- German Academic Exchange Service (DAAD)
- Cluster of Excellence Tailor Made Fuels from Biomass (TMFB) - Excellence Initiative of the German state government
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The depolymerization of kraft lignin with a copper-vanadium hydrotalcite-like catalyst (HTc-Cu-V) and V(acac)(3)/Cu(NO3)(2).3H(2)O mixtures to monomeric aromatic aldehydes and aromatic acids such as vanillin and vanillic acid using molecular oxygen as oxidant is reported. The obtained products correlate to model-based studies with erythro-1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol (1a). Kinetic investigations with 1a demonstrate that there is a combined effect of V(acac)(3) together with Cu(NO3)(2.)3H(2)O that enhances the catalytic activity and increases the selectivity and yield for the cleavage products veratric acid and veratraldehyde. Veratric acid is formed through reaction pathways involving either the transient oxidation products 1-(3,4-dimethoxyphenyl)-3-hydroxy-2-(2-methoxyphenoxy)propan-1-one (2) and 1-(3,4-dimethoxyphenyl)-2-(2-methoxyphenoxy)prop-2-en-1-one (5) or through overoxidation of veratraldehyde. The formation of veratraldehyde likely proceeds through C-C bond cleavage involving either a retro-aldol or a single electron transfer mechanism.
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