Pyrolytic cleavage mechanisms of lignin-ether linkages: A study on p-substituted dimers and trimers

Holzforschung

Volumn 62, Issue 1, 2008, Pages 50-56

  Kawamoto, Haruo ^a   Nakamura, Takeshi ^a   Saka, Shiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

ether; ether; Bond dissociation energy (BDE); Cleavage mechanism; Dimer; Hammett's substituent constant; Heterolytic; Homolytic; Lignin; Pyrolysis; Substituent effect; Trimer

Indexed keywords

DIMERS; DISSOCIATION; ETHERS; KETONES; PYROLYSIS; REACTION KINETICS;

HETEROLYTIC CLEAVAGE; PYROLYTIC CLEAVAGE; SUBSTITUENT CONSTANTS;

LIGNIN;

DIMERS; DISSOCIATION; ETHERS; KETONES; LIGNINS; PYROLYSIS; REACTION KINETICS;

EID: 36849011024     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/HF.2008.007     Document Type: Article

References (21)

1. Autrey, S.T., Alnajjar, M.S., Nelson, D.A., Franz, J.A. (1991) Absolute rate constants for β-Scission reaction of the 1-phenyl-2-phenoxypropyl radical: a model for radical reactions of lignin. J. Org. Chem. 56:2197-2202.
2. Brežný , R., Mihálov, V., Kováčik, V. (1983) Low temperature thermolysis of lignins. I. Reactions of β-O-4 model compounds. Holzforschung 37:199-204.
3. Brežný, R., Šurina, I.V., Kováčik, V. (1984) Low temperature thermolysis of lignins. II. Thermofractography and thermal analysis of β-O-4 model compounds. Holzforschung 38:19-24.
4. Britt, P.F., Buchanan, A.C. III, Thomas, K.B., Lee, S.-K. (1995) Pyrolysis mechanisms of lignin: surface-immobilized model compound investigation of acid-catalyzed and free-radical reaction pathways. J. Anal. Appl. Pyrolysis 33:1-19.
5. Dimmel, D.R., Shepard, D. (1982) Synthesis of lignin model dimers by novel techniques. J. Wood Chem. Technol. 2:297-315.
6. Evans, R.J., Milne, T.A., Soltys, M.N. (1986) Direct mass-spectrometric studies of the pyrolysis of carbonaceous fuels. III. Primary pyrolysis of lignin. J. Anal. Appl. Pyrolysis 9:207-236.
7. Faix, O., Meier D., Fortmann, I. (1988) Pyrolysis-gas chromatography-mass spectrometry of two trimeric lignin model compounds with alkyl-aryl ether structure. J. Anal. Appl. Pyrolysis 14:135-148.
8. Kawamoto, H., Horigoshi, S., Saka, S. (2007a) Pyrolysis reactions of various lignin model dimers. J. Wood. Sci. 53:168-174.
9. Kawamoto, H., Horigoshi, S., Saka, S. (2007b) Effects of sidechain hydroxyl groups on pyrolytic β-ether cleavage of phenolic lignin model dimer. J. Wood. Sci. 53:268-271.
10. Kishimoto, T., Sano, Y. (2002) Delignification mechanism during high-boiling solvent pulping. Part 2. Homolysis of guaiacylglycerol-β- guaiacyl ether. Holzforschung 56:623-631.
11. Klein, M.T., Virk, P.S. (1983) Model pathways in lignin thermolysis. 1. Phenethyl phenyl ether. Ind. Eng. Chem. Fundam. 22:35-45.
12. Li, S., Lundquist, K. (2001) Reaction of the β-aryl ether lignin model 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1-propanol on heating in aqueous solution. Holzforschung 55:296-301.
13. Nakamura, T., Kawamoto, H., Saka, S. (2007) Pyrolysis behavior of Japanese cedar wood lignin studied with various model dimers. J. Anal. Appl. Pyrolysis, in press.
14. Ponomarev, D.A. (1997) Formation of quinone methides: an alternative pathway to thermal degradation of some β-O-4-ether as compounds modeling lignin. Russian J. Appl. Chem. 70:824-826.
15. Ralph, J., Young, A. (1983) Stereochemical aspects of addition reactions involving lignin model quinine methides. J. Wood. Chem. Technol. 3:161-181.
16. Sano, Y. (1975) Hydrolysis of lignin with dioxane and water XV. Hydrolysis of 1-guaiacyl-2-guaiacoxy-1-propene-3-ol and guaiacylglycerol-β- guaiacyl ether. Mokuzai Gakkaishi 21:508-519.
17. Sano, Y. (1989) Reactivity of β-O-4 linkages in lignin during solvolysis pulping. Degradation of β-O-4 lignin model compounds. Mokuzai Gakkaishi 35:813-819.
18. Scalbert, A., Monties, B., Rolando, C., Sierra-Escudero, A. (1986) Formation of ether linkage between phenolic acids and Gramineae lignin: a possible mechanism involving quinone methides. Holzforschung 40:191-195.
19. Suryan, M.M., Kafafi, S.A., Stein, S.E. (1989) Dissociation of substituted anisoles: substituent effects on bond strengths. J. Am. Chem. Soc. 111:4594-4600.
20. Tanahashi, M., Karina, M., Tamabuchi, K., Higuchi, M. (1989) Degradation mechanism of lignin accompanying steam explosions. I. Degradation products of lignin and β-O-4 lignin substructure model dimers. Mokuzai Gakkaishi 35:135-143.
21. 3 bond dissociation energies in phenol and anisole. J. Org. Chem. 61:7904-7910.