Structure-function relationships in the phenolation of lignins from different sources

ACS Sustainable Chemistry and Engineering

Volumn 3, Issue 10, 2015, Pages 2526-2532

  Podschun, Jacob ^a   Stücker, Alexander ^b   Saake, Bodo ^a   Lehnen, Ralph ^b  

^a UNIVERSITY OF HAMBURG   (Germany)

^b Institute for Wood Physics and Mechanical Technology of Wood   (Germany)

Author keywords

31P NMR; Elemental analysis; GPC; Organosolv lignins; Phenolation; Technical lignins; Thermosetting resins

Indexed keywords

CHEMICAL ACTIVATION; CHEMICAL ANALYSIS; HARDWOODS; ION EXCHANGE; PHENOLIC RESINS; RESINS; SOFTWOODS; THERMOSETS;

31P-NMR; ALIPHATIC HYDROXYL GROUPS; COMMERCIAL PROCESS; ORGANOSOLV LIGNIN; PHENOL FORMALDEHYDE RESINS; PHENOLATION; SOFTWOOD KRAFT LIGNINS; STRUCTURE-FUNCTION RELATIONSHIP;

LIGNIN;

FORMALDEHYDE; LIGNINS; MOLECULAR WEIGHT; ORGANOSOLV LIGNINS;

EID: 84990930968     PISSN: None     EISSN: 21680485     Source Type: Journal    
DOI: 10.1021/acssuschemeng.5b00705     Document Type: Article

References (40)

1. Tomani, P. The lignoboost process. Cellul. Chem. Technol. 2010, 44, 53-58.
2. 2 precipitated Kraft lignin to promote its utilization. Green Chem. 2010, 12 (1), 31-34.
3. Velez, J., Thies, M. C. Solvated liquid-lignin fractions from a Kraft black liquor. Bioresour. Technol. 2013, 148, 586-590.
4. Kouisni, L., Holt-Hindle, P., Maki, K., Paleologou, M. The Lignoforce System: A new process for the production of high-quality lignin from black liquor. J. Sci. Technol. For. Prod. Proc. 2012, 2 (4), 6-10.
5. FAO. Pulp and Paper Capacities 2013-2018, Rome, 2014.
6. Lora, J. H. Industrial commercial lignins: Sources, properties and applications. In Monomers, Polymers and Composites from Renewable Resources, Belgacem, M. N., Gandini, A., Eds., Elsevier Ltd., 2008, pp 225-241.
7. Larsen, J., Haven, M. O., Thirup, L. Inbicon makes lignocellulosic ethanol a commercial reality. Biomass Bioenergy 2012, 46, 36-45.
8. Leskinen, T., Kelley, S. S., Argyropoulos, D. S. Refining of Ethanol Biorefinery Residues to Isolate Value Added Lignins. ACS Sustainable Chem. Eng. 2015, 3 (7), 1632-1641.
9. McCoy, M. Enzymes poised for cellulosic success. Chem. Eng. News Arch. 2012, 90 (41), 22-25.
10. Environmental Entrepreneurs. E2 Advanced biofuel market report, 2015.
11. www.demoplants.bioenergy2020.eu, www.iowarfa.org/resources-ethanol-refineries.php and company homepages www.betarenewables.com, www.abengoabioenergy.com, www.iogen.ca, www.ineos.com, www.zeachem.com (accessed May 11, 2015), www. adityabirla.com, www.asianlignin.com (accessed July 27, 2015).
12. Deep Research Report on Global and China Lignin and Lignin-Based Products Industry. www.deepresearchreports.com/112435.html (accessed May 11, 2015).
13. Strassberger, Z., Tanase, S., Rothenberg, G. The pros and cons of lignin valorisation in an integrated biorefinery. RSC Adv. 2014, 4 (48), 25310-25318.
14. Ragauskas, A J., Beckham, G. T., Biddy, M. J., Chandra, R., Chen, F., Davis, M. F., Davison, B. H., Dixon, R. A., Gilna, P., Keller, M., et al. Lignin valorization: improving lignin processing in the biorefinery. Science 2014, 344 (6158), 1246843.
15. Strassberger, Z., Prinsen, P., Van Der Klis, F., Van Es, D. S., Tanase, S., Rothenberg, G. Lignin solubilisation and gentle fractionation in liquid ammonia. Green Chem. 2015, 17, 325-334.
16. Hu, L., Pan, H., Zhou, Y., Zhang, M. Methods to improve lignin's reactivity as a phenol substitute and as replacement for other phenolic compounds: A brief review. BioResources 2011, 6 (3), 3515-3525.
17. Duval, A., Lawoko, M. A review on lignin-based polymeric, micro-and nano-structured materials. React. Funct. Polym. 2014, 85, 78-96.
18. Laurichesse, S., Averous, L. Chemical modification of lignins: Towards biobased polymers. Prog. Polym. Sci. 2014, 39 (7), 1266-1290.
19. Funaoka, M. Sequential transformation and utilization of natural network polymer "LIGNIN". React. Funct. Polym. 2013, 73 (2), 396-404.
20. Podschun, J., Saake, B., Lehnen, R. Reactivity enhancement of organosolv lignin by phenolation for improved bio-based thermosets. Eur. Polym. J. 2015, 67, 1-11.
21. Cetin, N. S., Ozmen, N. Use of organosolv lignin in phenol-formaldehyde resins for particleboard production: I. Organosolv lignin modified resins. Int. J. Adhes. Adhes. 2002, 22, 477-480.
22. Cetin, N. S., Ozmen, N. Use of organosolv lignin in phenol-formaldehyde resins for particleboard production: II. Particleboard production and properties. Int. J. Adhes. Adhes. 2002, 22, 481-486.
23. Ono, H., Sudo, K. Wood adhesives from phenolysis lignin: A way to use lignin from steam-explosion process. In Lignin Properties and Materials, ACS symposium series 397, Glasser, W. G., Sarkanen, S., Eds., American Chemical Society: Washington DC, 1989, pp 334-345.
24. Alonso, M. V., Oliet, M., Rodriguez, F., Garcia, J., Gilarranz, M. A., Rodr guez, J. J. Modification of ammonium lignosulfonate by phenolation for use in phenolic resins. Bioresour. Technol. 2005, 96 (9), 1013-1018.
25. Du, X., Li, J., Lindstrom, M. E. Modification of industrial softwood kraft lignin using Mannich reaction with and without phenolation pretreatment. Ind. Crops Prod. 2014, 52, 729-735.
26. Yang, S., Wen, J.-L., Yuan, T.-Q., Sun, R.-C. Characterization and phenolation of biorefinery technical lignins for lignin-phenol-formaldehyde resin adhesive synthesis. RSC Adv. 2014, 4 (101), 57996-58004.
27. Puls, J., Schreiber, A., Saake, B. Conversion of Beechwood into Platform Chemicals after Organosolv Treatment. Proceedings of the 15th ISWFPC, Oslo, Norway, June 15-18, 2009.
28. Granata, A., Argyropoulos, D. S. 2-Chloro-4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaphospholane, a reagent for the accurate determination of the uncondensed and condensed phenolic moieties in lignins. J. Agric. Food Chem. 1995, 43, 1538-1544.
29. Zawadzki, M., Ragauskas, A. N-hydroxy compounds as new internal standards for the 31P-NMR determination of lignin hydroxy functional groups. Holzforschung 2001 , 55 (3), 283-285.
30. Viebock, F., Schwappach, A. Eine neue Methode zur mafianalytischen Bestimmung der Methoxyl-und Athoxylgruppe. Ber. Dtsch. Chem. Ges. A/B 1930, 63 (10), 2818-2823.
31. Willfor, S., Pranovich, A., Tamminen, T., Puls, J., Laine, C., Suurnakki, A., Saake, B., Uotila, K., Simolin, H., Hemming, J., et al. Carbohydrate analysis of plant materials with uronic acid-containing polysaccharides-A comparison between different hydrolysis and subsequent chromatographic analytical techniques. Ind. Crops Prod. 2009, 29 (2-3), 571-580.
32. TAPPI UM 250. Acid-soluble lignin in wood and pulp, Atlanta, GA, 1985.
33. Huijgen, W. J. J., Telysheva, G., Arshanitsa, A., Gosselink, R. J. A., de Wild, P. J. Characteristics of wheat straw lignins from ethanol-based organosolv treatment. Ind. Crops Prod. 2014, 59, 85-95.
34. Mansouri, N. E. El, Salvado, 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, 8-16.
35. Gosselink, R. J. A., van Dam, J. E. G., de Jong, E., Scott, E. L., Sanders, J. P. M., Li, J., Gellerstedt, G. Fractionation, analysis, and PCA modeling of properties of four technical lignins for prediction of their application potential in binders. Holzforschung 2010, 64 (2), 193-200.
36. Lin, B. L., Yao, Y., Shiraishi, N. Liquefaction Mechanism of /7-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis Part 1. Identification of the Reaction Products. Holzforschung 2001, 55, 617-624.
37. Lin, L., Nakagame, S., Yao, Y., Yoshioka, M., Shiraishi, N. Liquefaction Mechanism of /7-O-4 Lignin Model Compound in the Presence of Phenol under Acid Catalysis Part 2. Reaction Behavior and Pathways. Holzforschung 2001, 55, 625-630.
38. Koda, K., Gaspar, A. R., Yu, L., Argyropoulos, D. S. Molecular weight-functional group relations in softwood residual kraft lignins. Holzforschung 2005, 59, 612-619.
39. Wroblewski, A. E., Lensink, C., Markuszewski, R., Verkade, J. G. 31P NMR Spectroscopic Analysis of Coal Pyrolysis Condensates and Extracts for Heteroatom Functionalities Possessing Labile Hydrogen. Energy Fuels 1988, 2 (6), 765-774.
40. Liang, F. B., Song, Y. L., Huang, C. P., Li, Y. X., Chen, B. H. Synthesis of novel lignin-based ion-exchange resin and its utilization in heavy metals removal. Ind. Eng. Chem. Res. 2013, 52 (3), 1267-1274.