Studies on electrooxidation of lignin and lignin model compounds. Part 1: Direct electrooxidation of non-phenolic lignin model compounds

Holzforschung

Volumn 66, Issue 3, 2012, Pages 303-309

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

^a KYOTO UNIVERSITY   (Japan)

Author keywords

C carbonylation; cyclic voltammetry (CV); direct electrooxidation; ECEC mechanism; lignin

Indexed keywords

BULK ELECTROLYSIS; DIMERIC COMPOUNDS; ECEC MECHANISMS; ELECTROCHEMICAL BEHAVIORS; ELECTROLYSIS REACTION; GUAIACYL; HIGH YIELD; LIGNIN MODEL COMPOUND; MODEL COMPOUND; NON-PHENOLIC LIGNIN;

ANODIC OXIDATION; CARBONYL COMPOUNDS; CARBONYLATION; CYCLIC VOLTAMMETRY; ELECTROLYSIS; ELECTROOXIDATION; ETHANOL; ETHERS; PHENOLS;

LIGNIN;

EID: 84860619349     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/hf.2011.069     Document Type: Article

References (30)

1. Aoyagi, T., Hosoya, S., Nakano, J. (1980) Contribution of a-carbonyl groups to the degradation of lignin during oxygen-alkali cooking. Mokuzai Gakkaishi 26:27-30.
2. Baciocchi, E., Bietti, M., Lanzalunga, O. (2000) Mechanistic aspects of b-bond-cleavage reactions of aromatic radical cations. Acc. Chem. Res. 33:243-251.
3. Bortolomeazzi, R., Sebastianutto, N., Toniolo, R., Pizzariello, A. (2007) Comparative evaluation of the antioxidant capacity of smoke flavouring phenols by crocin bleaching inhibition, DPPH radical scavenging and oxidation potential. Food Chem. 100: 1481-1489.
4. Britton, W., Steelink, C. (1974) The electrochemical oxidation of lignin model compounds II. Oxidation of 3,5-dimethoxy-4- hydroxyacetophenone. Tetrahedron Lett. 33:2873-2876.
5. Bruno, F., Pham, M.C., Dubois, J.E. (1977) Polaromicrotribometric study of polyphenylene oxide film formation on metal electrodes by electrolysis of disubstituted phenols. Electrochim. Acta 22: 451-457.
6. Chabaud, B., Sundholm, F. (1978) Aniodic oxidation of some phenols related to lignin II. Oxidation of isoeugenol methylether and 4-propylveratrole in acetonitrile. Electrochim. Acta 23: 659-667.
7. Crestini, C., D'Auria, M. (1997) Singlet oxygen in the photodegradation of lignin models. Tetrahedron 53:7877-7888.
8. Ezerskis, Z., Jusys, Z. (2001) Electropolymerization of chlorinated phenols on a Pt electrode in alkaline solution Part I: A cyclic voltammetry study. J. Appl. Electrochem. 31:1117-1124.
9. Gierer, J., Ljunggren, S. (1979) The reactions of lignin during sulfate pulping Part 16. The kinetics of the cleavage of b-aryl ether linkages in structures containing carbonyl groups. Svensk Papperstidning 82:71-81.
10. Gierer, J., Norén, I. (1982) Oxidative pretreatment of pine wood to facilitate delignification during kraft pulping. Holzforschung 36:123-130.
11. Gierer, J., Ljunggren, S., Ljungquist, P., Norén, I. (1980) The reactions of lignin during sulfate pulping. Part 18. The significance of a-carbonyl groups for the cleavage of b-aryl ether structures. Svensk Papperstidning 83:363-369.
12. Hammerich, O., Parker, V.D. (1973) The reversible oxidation of aromatic cation radicals to dications. Solvents of low nucleophilicity. Electrochim. Acta 18:537-541.
13. Hosoya, S., Nakano, J. (1980) Reaction of a-carbonyl group in lignin during alkaline hydrogen peroxide bleaching. Mokuzai Gakkaishi 26:97-101.
14. Lalvani, S.B., Rajagopal, P. (1993) Hydrogen production from lignin- water solution by electrolysis. Holzforschung 47:283-286.
15. Limosin, D., Canquis, G.P. (1985)é tudeélectrochimique de quelques composes diméres modéles de la lignine. Holzforschung 39:91-98.
16. Limosin, D., Pierre, G., Cauquis, G. (1986) Oxidation electrochimique de quelques echantillons de lignine en solution aqueus basique. Holzforschung 40:31-36.
17. Ljunggren, S. (1980) The significance of aryl ether cleavage in kraft delignification of softwood. Svensk Papperstidning 83:363-369.
18. 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.
19. Löbbecke, J.G., Lindner, A., Wegner, G., Wabner, G.W. (1990) Anodic modification of lignin during electrolysis in the organocell process. Holzforschung 44:401-406.
20. Nakatsubo, F., Sato, K., Higuchi, T. (1975) Synthesis of guaiacylglycerol- b-guaiacyl ether. Holzforschung 29:165-168.
21. 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.
22. Pardini, V.L., Vargas, R.R., Viertler, H., Utley, J.H.P. (1992) Anodic cleavage of lignin model dimers in methanol. Tetrahedron 48: 7221-7228.
23. Parpot, P., Bettencourt, A.P., Carvalho, A.M., Belgsier, E.M. (2000) Biomass conversion; attempted electrooxidation of lignin for vanillin production. J. Appl. Electrochem. 30:727-731.
24. Rochefort, D., Bourbonnais, R., Leech, D., Paice, M.G. (2002) Oxidation of lignin model compounds by organic and transition metal- based electron transfer mediators. Chem. Comm. 11: 1182-1183.
25. Sawyer, D.T., Sobkowiak, A., Roberts, J.L. (1995) Electrochemistry for Chemists, 2nd Edn. Wiley, New York.
26. Sjöblom, K. (1996) Extended delignification in kraft cooking through improved selectivity. Nord. Pulp Pap. Res. J. 11:177-185.
27. Smith, C., Utley, J., Petrescu, M., Viertler, H. (1989) Biomass electrochemistry: anodic oxidation of an organo-solv lignin in the presence of nitroaromatics. J. Appl. Electrochem. 19:535-539.
28. Steelink, C., Britton, W. (1974) The electrochemical oxidation of lignin model compounds I. Oxidation of 3,5-dimethoxy-4- hydroxy-a-methylbenzyl alcohol. Tetrahedron Lett. 33:2869-2872.
29. Sundholm, F. (1982) Anodic oxidation as a tool for mechanistics studies, guaiacol and 4-propyl-guaiacol in aprotic media. Holzforschung 36:7-74.
30. Tobimatsu, Y., Takano, T., Kamitakahara, H., Nakatsubo, F. (2008) Studies on the dehydrogenative polymerizations of monolignol b-glycosides. Part3: Horseradish peroxidase-catalysed polymerizations of triandrin and isosyringin. J. Wood Chem. Technol. 28:69-83.