Insights into oxidative conversion of lignin to high-added-value phenolic aldehydes

Industrial and Engineering Chemistry Research

Volumn 50, Issue 2, 2011, Pages 741-748

  Rodrigues Pinto, Paula C ^a   Borges Da Silva, Eduardo A ^a   Rodrigues, Alírio Egídio ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

CONCENTRATION PROFILES; DIFFERENT ORIGINS; HARDWOOD LIGNINS; HIGH REACTIVITY; HIGHER YIELD; ISOLATION PROCESS; KRAFT LIGNIN; MOLECULAR WEIGHT DETERMINATION; NITROBENZENE OXIDATION; ORGANOSOLV; OXIDATIVE CONVERSION; PHENOLIC HYDROXYL; PINUS SPP; PULPING PROCESS; REACTION TIME; REACTIVE MEDIUM; SYRINGALDEHYDE;

ALDEHYDES; MOLECULAR OXYGEN; OXIDATION; PHENOLS; WOOD;

LIGNIN;

ALDEHYDES; ALKALI LIGNINS; LIGNINS; MOLECULAR WEIGHT; ORGANOSOLV LIGNINS; OXIDATION;

EID: 78651404977     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie102132a     Document Type: Conference Paper

References (54)

1. Sjöström, E. Wood Chemistry, Fundamentals and Applications; Academic Press: New York, 1981.
2. Lewin, M.; Goldstein, I. S. Wood Structure and Composition; Marcel Dekker: New York, 1991; pp 183-261.
3. Evtuguin, D. V.; Neto, C. P.; Silva, A. M. S.; Domingues, P. M.; Amado, F. M. L.; Robert, D.; Faix, O. Comprehensive study on the chemical structure of dioxane lignin from plantation Eucalyptus globulus wood J. Agric. Food. Chem. 2001, 49 (9) 4252-4261
4. Pinto, P. C.; Evtuguin, D. V.; Neto, C. P. Effect of structural features of wood biopolymers on hardwood pulping and bleaching performance Ind. Eng. Chem. Res. 2005, 44 (26) 9777-9784
5. Adler, E. Lignin chemistry-past, present and future Wood Sci. Technol. 1977, 11 (3) 169-218
6. Tomani, P.; Axegard, P. In Development and demonstration of the LignoBoost process; The ILI Umbrella Programme and Other Existing and New Approaches in Lignin Research, ILI 8th Forum, Rome, May 10-12; The International Lignin Institute: Rome, 2007; pp 109-113.
7. Tomani, P. In Large scale lignin removal experiences; Nordic Wood Biorefinery Conference, NWBC 2008, Stockholm, March 11-13; STFI-Packforsk, Stockholm, 2008; pp 168-174.
8. Pye, E. K. Industrial Lignin Production and Applications; Wiley-VCH Verlag GmbH: Berlin, Germany, 2008; pp 165-200.
9. Hanselmann, K. W. Lignochemicals Cell. Mol. Life Sci. 1982, 38 (2) 176-189
10. Lora, J. H.; Glasser, W. G. Recent industrial applications of lignin: A sustainable alternative to nonrenewable materials J. Polym. Environ. 2002, 10 (1) 39-48
11. Zakzeski, J.; Bruijnincx, P. C. A.; Jongerius, A. L.; Weckhuysen, B. M. The catalytic valorization of lignin for the production of renewable chemicals Chem. Rev. 2010, 110 (6) 3552-3599
12. ICIS News data base. http://www.icis.com/Articles/2006/12/15/2017991/IN- BRIEF-Consumer-specialities.html (accessed July 1, 2010).
13. Hocking, M. B. Vanillin: synthetic flavoring from spent sulfite liquor J. Chem. Educ. 1997, 74 (9) 1055
14. Bjørsvik, H.-R.; Minisci, F. Fine chemicals from lignosulfonates. 1. Synthesis of vanillin by oxidation of lignosulfonates Org. Process Res. Dev. 1999, 3 (5) 330-340
15. Bjørsvik, H.-R.; Liguori, L. Organic processes to pharmaceutical chemicals based on fine chemicals from lignosulfonates Org. Process Res. Dev. 2002, 6 (3) 279-290
16. Wu, G.; Heitz, M.; Chornet, E. Improved alkaline oxidation process for the production of aldehydes (vanillin and syringaldehyde) from steam-explosion hardwood lignin Ind. Eng. Chem. Res. 1994, 33 (3) 718-723
17. Marwedel, T., Vanillin from Borregaard gives small CO2 footprints-Aroma Chemicals, March 17, 2009, Borregaard website. http://www.borregaard.com/eway/ default.aspx?pid=270&trg=MainLeft-12930&Main-12928=12930:0:15,4975:1:0: 0:::0:0&MainLeft-12930=12539:25998::1:12564:4:::0:0 (accessed October 10, 2010).
18. Mathias, A. L.; Rodrigues, A. E. Production of vanillin by oxidation of pine kraft lignins with oxygen Holzforschung 1995, 49 (3) 273-278
19. Fargues, C.; Mathias, A.; Rodrigues, A. Kinetics of vanillin production from kraft lignin oxidation Ind. Eng. Chem. Res. 1996, 35 (1) 28-36
20. Vázquez, G.; Antorrena, G.; González, J.; Freire, S. The influence of pulping conditions on the structure of acetosolv Eucalyptus lignins J. Wood Chem. Technol. 1997, 17 (1) 147-162
21. Sales, F. G.; Maranhão, L. C. A.; Filho, N. M. L.; Abreu, C. A. M. Experimental evaluation and continuous catalytic process for fine aldehyde production from lignin Chem. Eng. Sci. 2007, 62 (18-20) 5386-5391
22. Araújo, J. D. P.; Grande, C. A.; Rodrigues, A. E. Structured packed bubble column reactor for continuous production of vanillin from Kraft lignin oxidation Catal. Today 2009, 147, S330-S335, Supplement 1
23. Silva, E. A. B. d.; Zabkova, M.; Araújo, J. D.; Cateto, C. A.; Barreiro, M. F.; Belgacem, M. N.; Rodrigues, A. E. An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin Chem. Eng. Res. Des. 2009, 87 (9) 1276-1292
24. Araújo, J. D. P.; Grande, C. A.; Rodrigues, A. E. Vanillin production from lignin oxidation in a batch reactor Chem. Eng. Res. Des. 2010, 88 (8) 1024-1032
25. Sales, F. G.; MaranhÃo, L. s. C. A.; Lima Filho, N. M.; Abreu, C. A. M. Kinetic evaluation and modeling of lignin catalytic wet oxidation to selective production of aromatic aldehydes Ind. Eng. Chem. Res. 2006, 45 (20) 6627-6631
26. Sales, F. G.; Abreu, C. A. M.; Pereira, J. A. F. R. Catalytic wet-air oxidation of lignin in a three-phase reactor with aromatic aldehyde production Braz. J. Chem. Eng. 2004, 21, 211-218
27. Gellerstedt, G.; Lindfors, E. L. Structural changes in lignin during kraft cooking. Part 4. Phenolic hydroxyl groups in wood and kraft pulps Svensk Papperstidn 1984, 15, 115-118
28. Gellerstedt, G. r.; Gustafsson, K. Structural changes in lignin during kraft cooking. Part 5. Analysis of dissolved lignin by oxidative degradation J. Wood Chem. Technol. 1987, 7 (1) 65-80
29. Robert, D. R.; Bardet, M.; Gellerstedt, G. r.; Lindfors, E. L. Structural changes in lignin during kraft cooking. Part 3. On the structure of dissolved lignins J. Wood Chem. Technol. 1984, 4 (3) 239-263
30. Marques, A. P.; Evtuguin, D. V.; Magina, S.; Amado, F. M. L.; Prates, A. Structure of lignosulphonates from acidic magnesium-based sulphite pulping of Eucalyptus globulus J. Wood Chem. Technol. 2009, 29 (4) 337-357
31. Villar, J. C.; Caperos, A.; García-Ochoa, F. Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant Wood Sci. Technol. 2001, 35 (3) 245-255
32. Gierer, J.; Imsgard, F. The reactions of lignins with oxygen and hydrogen peroxide in alkaline media Svensk Papperstidn 1977, 80, 510-518
33. Tarabanko, V. E.; Fomova, N. A.; Kuznetsov, B. N.; Ivanchenko, N. M.; Kudryashev, A. V. On the mechanism of vanillin formation in the catalytic oxidation of lignin with oxygen React. Kinet. Catal. Lett. 1995, 55 (1) 161-170
34. Tarabanko, V. E.; Petukhov, D. V.; Selyutin, G. E. New mechanism for the catalytic oxidation of lignin to vanillin Kinet. Catal. 2004, 45 (4) 569-577
35. Tarabanko, V. E.; Koropatchinskaya, N. V.; Kudryashev, A. V.; Kuznetsov, B. N. Influence of lignin origin on the efficiency of the catalytic oxidation of lignin into vanillin and syringaldehyde Russ. Chem. Bull. 1995, 2, 367-371
36. Tomlinson, G. H.; Hibbert, H. Studies on lignin and related compounds. XXV. Mechanism of vanillin formation from spruce lignin sulfonic acids in relation to lignin structure J. Am. Chem. Soc. 1936, 58 (2) 348-353
37. Pinto, P. C.; Evtuguin, D. V.; Neto, C. P.; Silvestre, A. J. D. Behavior of Eucalyptus globulus lignin during kraft pulping. I. Analysis by chemical degradation methods J. Wood Chem. Technol. 2002, 22 (2) 93-108
38. Pinto, P. C.; Evtuguin, D. V.; Neto, C. P.; Silvestre, A. J. D.; Amado, F. M. L. Behavior of Eucalyptus globulus lignin during kraft pulping. II. Analysis by NMR, ESI/MS and GPC J. Wood Chem. Technol. 2002, 22 (2) 109-125
39. Browning, B. L. Methods in Wood Chemistry; Interscience Publishers: New York, 1967; Vol. 2.
40. Coimbra, M. A.; Waldron, K. W.; Selvendran, R. R. Isolation and characterisation of cell wall polymers from olive pulp (Olea europaea L.) Carbohydr. Res. 1994, 252, 245-262
41. Chen, C.-L. Nitrobenzene and cupric oxide oxidations. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, New York, 1992.
42. Pinto, P. C.; Borges da Silva, E. A.; Rodrigues, A. E., Comparative study of solid-phase extraction and liquid-liquid extraction for the reliable quantification of high value-added compounds from oxidation processes of wood derived lignin. Ind. Eng. Chem. Res. 2010; DOI: 10.1021/ie101680s, Publication Date (Web): October 27, 2010.
43. Lai, Y. Z., Determination of phenolic hydroxyl groups. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, New York, 1992.
44. Schultz, T. P.; Templeton, M. C. Proposed mechanism for the nitrobenzene oxidation of lignin Holzforschung 1986, 40 (2) 93-97
45. Gierer, J. Chemistry of delignification Wood Sci. Technol. 1985, 19 (4) 289-312
46. Ekeberg, D.; Gretland, K. S.; Gustafsson, J.; Bråten, S. M.; Fredheim, G. E. Characterisation of lignosulphonates and kraft lignin by hydrophobic interaction chromatography Anal. Chim. Acta 2006, 565 (1) 121-128
47. Lebo, S. E.; Gargulak, J. D.; McNally, T. J. Lignin. In Kirk-Othmer Encyclopedia of Chemical Technology; John Wiley & Sons, Inc.: New York, 2000.
48. Lora, J. H.; Wu, C. F.; Pye, E. K.; Balatinecz, J. J., Characteristics and potential applications of lignin produced by an organosolv pulping process. In Lignin; ACS Symposium Series Vol. 397; American Chemical Society: Washington, DC, 1989.
49. McDonough, J. The chemistry of organosolv delignification; Institute of Paper Science and Technology: Atlanta, GA, 1992.
50. Mansouri, N.-E. E.; Salvadó, J. Structural characterization of technical lignins for the production of adhesives: Application to lignosulfonate, kraft, soda-anthraquinone, organosolv and ethanol process lignins Ind. Crops Prod. 2006, 24 (1) 8-16
51. Lange, W.; Schweers, W. The carboxymethylation of organosolv and kraft lignins Wood Sci. Technol. 1980, 14 (1) 1-7
52. Ragnar, M.; Lindgren, C. T.; Nilvebrant, N.-O. pKa-Values of guaiacyl and syringyl phenols related to lignin J. Wood Chem. Technol. 2000, 20 (3) 277-305
53. Sultanov, V. S.; Wallis, A. F. A. Reactivities of guaiacyl and syringyl lignin model phenols towards oxidation with oxygen-alkali J. Wood Chem. Technol. 1991, 11 (3) 291-305
54. Tsutsumi, Y.; Kondo, R.; Sakai, K.; Imamura, H. The difference of reactivity between syringyl lignin and guaiacyl lignin in alkaline systems Holzforschung 1995, 49 (5) 423-428