Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin. Part 6: A review

Journal of Wood Chemistry and Technology

Volumn 35, Issue 1, 2014, Pages 27-42

  Yokoyama, Tomoya ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Alkyl aryl ether; Bromide; Chloride; Kinetic isotope effect; Sulfate; Veratrylglycerol guaiacyl ether

Indexed keywords

CHLORINE COMPOUNDS; ETHERS; LIGNIN; REACTION INTERMEDIATES; SULFUR COMPOUNDS;

ALKYL ARYL ETHERS; BROMIDE; CHLORIDE; GUAIACYL; KINETIC ISOTOPE EFFECTS; SULFATE;

BROMINE COMPOUNDS;

EID: 84910645819     PISSN: 02773813     EISSN: 15322319     Source Type: Journal    
DOI: 10.1080/02773813.2014.881375     Document Type: Review

References (49)

1. Cramer, A.B.; Hunter, J.M.; Hibbert, H. Studies on lignin and related compounds XXXVII: The ethanolysis of spruce wood. J. Am. Chem. Soc. 1939, 61(2), 509-516.
2. Hunter, J.M.; Cramer, A.B.; Hibbert, H. Studies on lignin and related compounds XXXVIIIII: Ethanolysis of maple wood. J. Am. Chem. Soc. 1939, 61(2), 516-520.
3. Brickman, L.; Hawkins, W.L.; Hibbert, H. Studies on lignin and related compounds XLVIII: Identification of vanillin and vanilloyl methyl ketone as ethanolysis products from spruce wood. J. Am. Chem. Soc. 1940, 62(8), 2149-2154.
4. Mitchell, L.; Hibbert, H. Studies on lignin and related compounds LXXX: The ethanolysis of 1-acetoxy-1-(4-acetoxy-3-methoxyphenyl)-2-propanone and its relation to lignin structure. J. Am. Chem. Soc. 1944, 66(4), 602-604.
5. Fisher, H.E.; Hibbert, H. Studies on lignin and related compounds 83: Synthesis of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)2-propanone. J. Am. Chem. Soc. 1947, 69(5), 1208-1210.
6. Adler, E.; Pepper, J.M.; Eriksoo, E. Action of mineral acid on lignin and model substances of guaiacylglycerol-β-aryl ether type. Ind. Eng. Chem. 1957, 49(9), 1391-1392.
7. Pepper, J.M.; Baylis, P.E.T.; Adler, E. The isolation and properties of lignins obtained by the acidolysis of spruce and aspen woods in dioxane-water medium. Can. J. Chem. 1959, 37(8), 1241-1248.
8. Gellerstedt, G.; Pranda, J.; Lindfors, E.-L. Structural and molecular properties of residual birch kraft lignins. J. Wood Chem. Technol. 1994, 14(4), 467-482.
9. Lundquist, K. Isolation of 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-2-propanone from lignin. Acta Chem. Scand. 1962, 16(9), 2303-2304.
10. Adler, E.; Lundquist, K. Spectrochemical estimation of phenylcoumaran elements in lignin. Acta Chem. Scand. 1963, 17(1), 13-26.
11. Lundquist, K. On the separation of lignin degradation products. Acta Chem. Scand. 1964, 18(5), 1316-1317.
12. Lundquist, K.; Miksche, G. A new linkage principle for guaiacylpropane units in spruce lignin. Tetrahedron Lett. 1965, 6(25), 2131-2136.
13. Adler, E. Lignin chemistry: Past, present and future. Wood Sci. Technol. 1977, 11(3), 169-218.
14. Lapierre, C.; Monties, B.; Rolando, C. Thioacidolysis of lignin: Comparison with acidolysis. J. Wood Chem. Technol. 1985, 5(2), 277-292.
15. Lapierre, C.; Monties, B.; Rolando, C. Preparative thioacidolysis of spruce lignin: Isolation and identification of main monomeric products. Holzforschung 1986, 40(1), 47-50.
16. Lapierre, C.; Monties, B.; Rolando, C. Thioacidolysis of poplar lignins: Identification of monomeric syringyl products and characterization of guaiacyl-syringyl lignin fractions. Holzforschung 1986, 40(2), 113-118.
17. Lu, F.C.; Ralph, J. Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: Protocol for analysis of DFRC monomers. J. Agric. Food Chem. 1997, 45(7), 2590-2592.
18. Lu, F.C.; Ralph, J. DFRC method for lignin analysis 1: New method for β-aryl ether cleavage: Lignin model studies. J. Agric. Food Chem. 1997, 45(12), 4655-4660.
19. Lu, F.C.; Ralph, J. The DFRC method for lignin analysis 2: Monomers from isolated lignins. J. Agric. Food Chem. 1998, 46(2), 574-552.
20. Lu, F.C.; Ralph, J. The DFRC method for lignin analysis part 3: NMR studies. J. Wood Chem. Technol. 1998, 18(2), 219-233.
21. Peng, J.P.; Lu, F.C.; Ralph, J. The DFRC method for lignin analysis 4: Lignin dimers isolated from DFRC-degraded loblolly pine wood. J. Agric. Food Chem. 1998, 46(2), 553-560.
22. Peng, J.P.; Lu, F.C.; Ralph, J. The DFRC method for lignin analysis 6: A simple modification for identifying natural acetates on lignins. J. Agric. Food Chem. 1998, 46(11), 4616-4619.
23. Peng, J.P.; Lu, F.C.; Ralph, J. The DFRC method for lignin analysis 5: Isochroman lignin trimers from DFRC-degraded Pines taeda. Phytochemistry 1999, 50(4), 659-666.
24. Lu, F.C.; Ralph, J. The DFRC method for lignin analysis 7: Behavior of cinnamyl end groups. J. Agric. Food Chem. 1999, 47(5), 1981-1987.
25. Lundquist, K.; Hedlund, K. Acid degradation of lignin I: The formation of ketones of the guaiacylpropane series. Acta Chem. Scand. 1967, 21(7), 1750-1754.
26. Lundquist, K. Acid degradation of lignin II: Separation and identification of low molecular weight phenols. Acta Chem. Scand. 1970, 24(3), 889-907.
27. Lundquist, K.; Ericsson, L. Acid degradation of lignin III: Formation of formaldehyde. Acta Chem. Scand. 1970, 24(10), 3681-3686.
28. Lundquist, K.; Ericsson, L. Acid degradation of lignin VI: Formation of methanol. Acta Chem. Scand. 1971, 25(2), 756-758.
29. Lundquist, K.; Kirk, T.K. Acid degradation of lignin IV: Analysis of lignin acidolysis products by gas chromatography, using trimethylsilyl derivatives. Acta Chem. Scand. 1971, 25(3), 889-894.
30. Lundquist, K.; Hedlund, K. Acid degradation of lignin V: Degradation products related to the phenylcoumaran type of structure. Acta Chem. Scand. 1971, 25(6), 2199-2210.
31. Lundquist, K.; Lundgren, R. Acid degradation of lignin part VII: The cleavage of ether bonds. Acta Chem. Scand. 1972, 26(5), 2005-2023.
32. Lundquist, K. Acid degradation of lignin part VIII: Low molecular weight phenols from acidolysis of birch lignin. Acta Chem. Scand. 1973, 27(7), 2597-2606.
33. Karlsson, O.; Lundquist, K.; Meuller, S.; Westlid, K. On the acidolytic cleavage of arylglycerol β-aryl ethers. Acta Chem. Scand. 1988, B42(1), 48-51.
34. Karlsson, O.; Lundquist, K. Acid reactions of hydrobenzoins: Effects of catalyst and reaction medium on product composition. Acta Chem. Scand. 1992, 46(3), 283-289.
35. Li, S.; Lundquist, K.; Stenhagen, G. Studies on the formation of 1-(4-hydroxy-3,5-dimet-hoxyphenyl)-2-(4-hydroxy-3-methoxyphenyl)-1-propanone and 2-(4-hydroxy-3,5-dimethoxy-phenyl)-1-(4-hydroxy-3-methoxyphenyl)-1-propanone on acid treatment of birch lignin. Holzforschung 1996, 50(3), 253-257.
36. Li, S.; Karlsson, O.; Lundquist, K.; Stomberg, R. Acid reactions of the lignin model 1,2-bis(3,4-dimethoxyphenyl)-1,3-propanediol. Acta Chem. Scand. 1997, 51(3), 431-437.
37. Li, S.; Karlsson, O.; Lundquist, K. Acid reactions of lignin models of β-5 type. Holzforschung 1999, 53(1), 39-42.
38. Li, S.; Lundquist, K.; Westermark, U. Cleavage of arylglycerol β-aryl ethers under neutral and acid conditions. Nord. Pulp Pap. Res. J. 2000, 15(4), 292-299.
39. 3 type model compound. J. Wood Chem. Technol. 2011, 31(2), 172-182.
40. Yasuda, S.; Terashima, N.; Ito, T. Chemical structures of sulfuric acid lignin II: Chemical structures of condensation products from arylglycerol-β-aryl ether type structures. Mokuzai Gakkaishi 1981, 27(3), 216-222.
41. Ito, T.; Terashima, N.; Yasuda, S. Chemical structures of sulfuric acid lignin III: Reaction of arylglycerol-β-aryl ether with five percent sulfuric acid. Mokuzai Gakkaishi 1981, 27(6), 484-490.
42. 2-enol ethers in the acid-catalyzed hydrolysis of erythro-veratrylglycerol-β-(2-methoxyphnenyl) ether. J. Wood Chem. Technol. 1983, 3(2), 223-243.
43. Yasuda, S.; Ota, K. Chemical structures of sulfuric acid lignin X: Reaction of syringylglycerol-β-syringyl ether and condensation of syringyl nucleus with guaiacyl lignin model compounds in sulfuric acid. Holzforschung 1987, 41(1), 59-65.
44. Yasuda, S.; Terashima, N.; Kaneko, H. Chemical structures of hydrochloric acid lignin II: Reaction of arylglycerol-β-aryl ether with hydrochloric acid. Mokuzai Gakkaishi 1982, 28(9), 570-576.
45. Yasuda, S.; Adachi, K.; Terashima, N.; Ota, K. Chemical structures of sulfuric acid lignin VIII: Reactions of 1,2-diaryl-1,3-propanediol and pinoresinol with sulfuric acid. Mokuzai Gakkaishi 1985, 31(2), 125-131.
46. 2 type model compounds. Holzforschung 2008, 62(2), 164-168.
47. 2 type model compounds. J. Wood Chem. Technol. 2010, 30(3), 269-282.
48. Imai, T.; Yokoyama, T.; Matsumoto, Y. Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin IV: Dependence of acidolysis reaction on the type of acid. J. Wood Sci. 2011, 57(3), 219-225.
49. Imai, T.; Yokoyama, T.; Matsumoto, Y. Revisiting the mechanism of β-O-4 bond cleavage during acidolysis of lignin part V: On the characteristics of acidolysis using hydrobromic acid. J. Wood Chem. Technol. 2012, 32(2), 165-174.