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Comparison of Copper and Vanadium Homogeneous Catalysts for Aerobic Oxidation of Lignin Models
Abstract
The reactivity of copper and vanadium catalysts toward the aerobic oxidation of lignin models has been explored. Both (dipic)V V (O)(O i Pr) ( 3 ) (dipic = dipicolinate) and CuCl/TEMPO (TEMPO = tetramethylpiperidine N -oxide) catalyzed the aerobic oxidation of the lignin model compound 1,2-diphenyl-2-methoxyethanol ( 2 ). The vanadium catalyst 3 produced benzoic acid (85%) and methyl benzoate (84%) as the major products via the intermediate ketone benzoin methyl ether ( 4 ). The copper catalyzed reaction afforded benzaldehyde (84%) and methylbenzoate (88%) directly, with no intermediate formation of 4 . The more complex lignin model system 1-(3,5-dimethoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol-[2,3- 13 C 2 ] ( 5 - 13 C 2 ) was oxidized under air by vanadium catalyst 3, affording ketone 7 - 13 C 2 (65%), dehydrated ketone 8 - 13 C 2 (5%), alkene product 9 - 13 C 2 (14%), 3,5-dimethoxybenzoic acid (11%), 3,5-dimethoxybenzaldehyde (2%), 2-methoxyphenol, and formic acid- 13 C 1 (4%). Aerobic oxidation of ketone 7 - 13 C 2 using catalyst 3 produced dehydrated ketone 8 - 13 C 2, 3,5-dimethoxybenzoic acid, and formic acid- 13 C 1, suggesting that 7 is further oxidized under the catalytic conditions. In contrast, oxidation of β-O-4 model 5 - 13 C 2 using CuCl/TEMPO affords 3,5-dimethoxybenzaldehyde (43%), 3,5-dimethoxybenzoic acid (13%), 2-methoxyphenol (7%), formic acid- 13 C 1 (7%), ketone- 7 13 C 2 (1%), dehydrated ketone 8 - 13 C 2 (2%), and a number of higher molecular weight products, as determined by 1 H and 13 C NMR, GC-MS, and LC-MS. Attempted oxidation of ketone 7 using CuCl/TEMPO yielded primarily dehydrated ketone 8, indicating that the ketone is not an intermediate in the formation of the aldehyde product. The reactivities of the copper and vanadium catalysts in the oxidation of lignin model compounds 2 and 5 are discussed. Remarkably different selectivities were observed for the vanadium and copper catalyzed reactions, suggesting the potential of homogeneous catalysts for controlling selectivity in the aerobic oxidation of lignin.
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Cites
The Catalytic Valorization of Lignin for the Production of Renewable Chemicals
Zakzeski, J., Bruijnincx, P. C. A., Jongerius, A. L., & Weckhuysen, B. M. (2010) · Chemical Reviews · doi:10.1021/cr900354u · Cited by 4,468
Cited by
Catalytic Applications of Vanadium: A Mechanistic Perspective
Langeslay, R. R., Kaphan, D. M., Marshall, C. L., Stair, P. C., Sattelberger, A. P., & Delferro, M. (2019) · Chemical Reviews · doi:10.1021/acs.chemrev.8b00245 · Cited by 503
Homogeneous catalysis for the conversion of biomass and biomass-derived platform chemicals
Deuss, P. J., Barta, K., & de Vries, J. G. (2014) · Catal. Sci. Technol. · doi:10.1039/c3cy01058a · Cited by 316
Hanson, S. K., Wu, R., & Silks, L. A. “. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201107020 · Cited by 294
Self-citationNaturally occurring phenolic sources: monomers and polymers
Lochab, B., Shukla, S., & Varma, I. K. (2014) · RSC Adv. · doi:10.1039/c4ra00181h · Cited by 293
Advances in lignin valorization towards bio-based chemicals and fuels: lignin biorefinery
Cao, Y., Chen, S. S., Zhang, S., Ok, Y. S., Matsagar, B. M., Wu, K. C.-W., & Tsang, D. C. W. (2019) · Bioresource Technology · doi:10.1016/j.biortech.2019.121878 · Cited by 267
Figueirêdo, M. B., Hita, I., Deuss, P. J., Venderbosch, R. H., & Heeres, H. J. (2022) · Green Chemistry · doi:10.1039/d2gc00302c · Cited by 146
Zhang, J.-W., Lu, G.-P., & Cai, C. (2017) · Green Chemistry · doi:10.1039/c7gc02087b · Cited by 101
Cao, Y., Chen, S. S., Tsang, D. C. W., Clark, J. H., Budarin, V. L., Hu, C., Wu, K. C.-W., & Zhang, S. (2020) · Green Chemistry · doi:10.1039/c9gc03553b · Cited by 76
Metadata
- Authors
- Sedai, B., Díaz-Urrutia, C., Baker, R. T., Wu, R., Silks, L. A. “., & Hanson, S. K.
- Venue
- ACS Catalysis
- Publisher
- American Chemical Society (ACS)
- Published
- 2011-06-02
- Volume
- 1
- Issue
- 7
- Pages
- 794-804
- ISSN
- 2155-5435 (ISSN-L)
- OpenAlex
- W2320507318
- Cited by
- 187
- References
- 1
- FWCI
- 6.02
- Type
- journal article
- Language
- en
- Open access
- closed
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