Alkaline hydrolysis of nonphenolic α-carbonyl β-0-4 lignin dimers substituted on the leaving phenoxide ring: Comparison with benzylic hydroxyl analogues

Holzforschung

Volumn 52, Issue 1, 1998, Pages 57-60

  Criss, Dexter L ^a   Fisher, Thomas H ^b   Schultz, Tor P ^a  

^a MISSISSIPPI STATE UNIVERSITY   (United States)

^b MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

Alkaline hydrolysis; Lignin models; Nonphenolic 0 4 bond; SN2 mechanism; Substituent effects; Carbonyl

Indexed keywords

EID: 0040544751     PISSN: 00183830     EISSN: None     Source Type: Journal    
DOI: 10.1515/hfsg.1998.52.1.57     Document Type: Review

References (15)

1. Adler, E., B.O. Lindgren and U. Saeden. 1952. The β-guaiacyl ether of α-veratryl-glycerol as a lignin model. Svensk Papperstidn. 55, 245-254.
2. Chatterjea, J.N., A.K. Sinha and S. Lal. 1979. Synthesis of furano compounds. Part XLIII. J. Indian Chem. Soc. 56, 508-510.
3. Collier, W.E., T.H. Fisher, L.L. Ingram, Jr., A.L. Harris and T.P. Schultz. 1996. Alkaline hydrolysis of nonphenolic β-0-4 lignin model dimers: Further studies of the substituent effect of the leaving phenoxide. Holzforschung, 50, 420-424.
4. Evstigneyeu, E., H. Maiyorova and A. Platonov. 1991. Lignin functionalization and reactivity in alkaline pulping. 6th Int. Symp. on Wood and Pulping Chem., Vol. 2, 131-138.
5. Gierer, J. 1982. The chemistry of delignification. Holzforschung 36, 43-51.
6. Gierer, J. and S. Ljunggren. 1979. The reactions of lignins during sulfate pulping. 16. The kinetics of the cleavage of β-aryl ether linkages in structures containing carbonyl groups. Svensk Papperstidn. 82, 71-81.
7. Gierer J and I. Norén. 1962. Zur Spaltung von β-Hydroxy-Alkyl-Aryläthern durch Alkali. II. Der stereochemische Verlauf. Acta Chem. Scand. 16, 1976-1988.
8. Gierer, J. and I. Norén. 1982. Oxidative pretreatment of pine wood to facilitate delignification during kraft pulping. Holzforschung 36, 123-130.
9. Hubbard, T.F., Jr., Schultz, T.P. and T.H. Fisher. 1992. Alkaline hydrolysis of nonphenolic β-0- 4 lignin model dimers: Substituent effects on the leaving phenoxide in neighboring group vs. direct nucleophilic attack. Holzforschung 46, 315-320.
10. Lindeberg, O. and J. Walding. 1987. Reactions of nitrated kraft lignin in an alkaline oxygen bleaching stage. Tappi J. 70 (10), 119-123.
11. Ljunggren, S. 1980. The significance of aryl ether cleavage in kraft delignification of softwood. Svensk Papperstidn. 83, 363-369.
12. March, J. 1977. Advanced organic chemistry 2nd Ed. McGraw-Hill, New York, p. 319.
13. Meshgini, M. and K.V. Sarkanen. 1989. Synthesis and kinetics of acid-catalyzed hydrolysis of some α-aryl ether lignin model compounds. Holzforschung 43, 239-243.
14. Obst, J.R. 1983. Kinetics of alkaline cleavage of β-aryl ether bonds in lignin models: Significance to delignification. Holzforschung 37, 23-28.
15. Yokayama, S., T. Zshii, G. Takeya and A. Sakakibara. 1969. High resolution nuclear magnetic resonance spectra of model compounds related to lignin using dimethyl as sulfoxide solvent (in Japanese). Kogyo Kagaku Zasshi 72, 346-352.