Studies on electro-oxidation of lignin and lignin model compounds. Part 2: N-Hydroxyphthalimide (NHPI)-mediated indirect electro-oxidation of non-phenolic lignin model compounds

Holzforschung

Volumn 66, Issue 3, 2012, Pages 311-315

  Shiraishi, Takumi ^a   Takano, Toshiyuki ^a   Kamitakahara, Hiroshi ^a   Nakatsubo, Fumiaki ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

C carbonylation; cyclic voltammetry (CV); hydrogen atom transfer; indirect electro oxidation; lignin; N hydroxyphthalimide (NHPI)

Indexed keywords

CLEAVAGE PRODUCTS; CYCLIC VOLTAMMOGRAMS; DIMERIC COMPOUNDS; ELECTRONIC MEDIATORS; GUAIACYL; HIGH YIELD; HYDROGEN-ATOM TRANSFER; INDIRECT ELECTRO-OXIDATION; LIGNIN MODEL COMPOUND; N-HYDROXYPHTHALIMIDES; NON-PHENOLIC LIGNIN;

CARBONYL COMPOUNDS; CARBONYLATION; CYCLIC VOLTAMMETRY; ETHANOL; ETHERS; HYDROGEN; OXIDATION; PHENOLS;

LIGNIN;

EID: 84860646499     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/hf.2011.140     Document Type: Article

References (26)

1. Annunziatini, C., Baiocco, P., Gerini, M.F., Lanzalunga, O., Sjögren, B. (2005) Aryl substituted N-hydroxyphthalimides as mediators in the laccase-catalysed oxidation of lignin model compounds and delignification of wood pulp. J. Mol. Catal. B: Enzym. 32:89-96.
2. Bourbonnais, R., Leech, D., Paice, M.G. (1998) Electrochemical analysis of the interactions of laccase mediators with lignin model compounds. Biochim. Biophys. Acta 1379:381-390.
3. Cantarella, G. (2003) Free radical versus electron-transfer routes of oxidation of hydrocarbons by laccase/mediator systems: catalytic or stoichiometric procedures. J. Mol. Catal. B: Enzym. 22: 135-144.
4. Coseri, S. (2009) Phthalimide-N-oxyl (PINO) radical, a powerful catalytic agent: its generation and versatility towards various organic substrates. Catal. Rev. 51:218-292.
5. Crestini, C., D'Auria, M. (1997) Singlet oxygen in the photodegradation of lignin models. Tetrahedron 53:7877-7888.
6. Fabbrini, M., Galli, C., Gentili, P. (2002) Radical or electron-trnsfer mechanism of oxidation with some laccase/mediator systems. J. Mol. Catal. B: Enzym. 18:169-171.
7. Galli, C., Gentili, P. (2004) Chemical messengers: mediated oxidations with the enzyme laccase. J. Phys. Org. Chem. 17:973-977.
8. Gierer, J., Norén, I. (1982) Oxidative pretreatment of pine wood to facilitate delignification during kraft pulping. Holzforschung 36:123-130.
9. González Arzola, K., Arévalo, M.C., Falcón, M.A. (2009) Catalytic efficiency of natural and synthetic compounds used as laccasemediators in oxidising veratryl alcohol and kraft lignin, estimated by electrochemical analysis. Electrochim. Acta 54:2621-2629.
10. Gorgy, K., Lepretre, J.-C., Saint-Aman, E., Einhorn, C., Einhorn, J., Marcadal, C., Pierre, J.-L. (1998) Electrocatalytic oxidation of alcohols using substituted N-hydroxyphthalimides as catalysts. Electrochim. Acta 44:385-393.
11. Kim, H.-C., Mickel, M., Bartling, S., Hampp, N. (2001) Electrochemically mediated bleaching of pulp fibers. Electrochim. Acta 47:799-805.
12. Kishioka, S., Yamada, A. (2005) Kinetic study of the catalytic oxidation of benzyl alcohols by phthlimide-N-oxyl radical electrogenerated in acetonitrile using rotating disk electrode voltammetry. J. Electroanal. Chem. 578:71-77.
13. Kishioka, S., Yamada, A. (2006) Electro-oxidation of N-hydroxy imides for redox mediator in acetonitrile containing lutidine as a base. Electrochim. Acta 51:4582-4588.
14. Limosin, D., Pierre, G., Cauquis, G. (1986) Oxydation electrochimique de quelques echantillons de lignine en solution aqueuse basique. Holzforschung 40:31-36.
15. Limosin, D., Pierre, G., Cauquis, G., Chopin, J., Chadenson, M., Hauteville, M. (1985)é tudeélectrochimique de quelques composés diméres modéles de la lignine. Holzforschung 39: 91-98.
16. Ljunggren, S., Olsson A. (1984) The specificity in oxidation of some lignin and carbohydrate models and pine wood shavings with permanganate and pyridinum dichloromate before the kraft pulping process. Holzforschung 38:91-99.
17. Masui, M., Ueshima, T., Ozaki, S. (1983) N-hydroxyphthalimide as an effective mediator for the oxidation alcohols by electrolysis. J. Chem. Soc. Chem. Commun. 12:479-480.
18. Mickel, M., Kim H.-C, Noll S., Hampp N. (2003) Electrochemical mediator-based delignification, mediator properties and process performance. J. Electrochem. Soc. 150:E595-E600.
19. Morozova, O.V., Shumankovich, G.P., Shleev, S.V., Yaroporov, Ya. I. (2007) Laccase-mediator systems and their applications: a review. Appl. Biochem. Microbiol. 43:523-535.
20. Pardini, V.L., Smith, C.Z., Utley, J.H.P., Vargas, R.R., Viertler, H. (1991) Electroorganic reactions. 38. Mechanism of electrooxidative cleavage of lignin model dimmers. J. Org. Chem. 56: 7305-7313.
21. Rochefort, D., Bourbonnais, R., Leech, D., Paice, M.G. (2002a) Oxidation of lignin model compounds by organic and transition metal-based electron transfer mediators. Chem. Comm. 11: 1182-1183.
22. Rochefort, D., Bourbonnais, R., Leech, D. Renaud, S., Paice, M.G. (2002b) Electrochemical oxidation of transition metal-based mediators for pulp delignification. J. Electrochem. Soc. 149: D15-D20.
23. Serve, D. (1975) Oxidation anodique de quelques N-arylhydroxylamies et proprietes electrochimiques des radicaux nitroxydes en milieu acetonitrile. Electrochim. Acta 20:469-477.
24. Shiraishi, T., Takano, T., Kamitakahara, H., Nakatsubo, F. (2011) Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds. Holzforschung. DOI: 10.1515/HF.2011.069.
25. Ueda, C., Noyama, M., Ohmori, H., Masui, M. (1987) Reactivity of phthalimide-N-oxyl: a kinetic study. Chem. Pharm. Bull. 35:1372-1377.
26. Weinberg, N.L., Weinberg, H.R. (1968) Electrochemical oxidation of organic compounds. Chem. Rev. 68:449-523.