References
- Bozell, J. J. Feedstocks for the Future - Biorefinery Production of Chemicals from Renewable Carbon. Clean Soil. Air. Water 2008, 36, 641–647. DOI: https://doi.org/10.1002/clen.200800100.
- Shinde, S. D.; Meng, X.; Kumar, R.; Ragauskas, A. J. Recent Advances in Understanding the Pseudo-Lignin Formation in a Lignocellulosic Biorefinery. Green Chem. 2018, 20, 2192–2205. DOI: https://doi.org/10.1039/C8GC00353J.
- Tardy, B. L.; Yokota, S.; Ago, M.; Xiang, W.; Kondo, T.; Bordes, R.; Rojas, O. J. Nanocellulose–Surfactant Interactions. Curr. Opin. Colloid Interface Sci. 2017, 29, 57–67. DOI: https://doi.org/10.1016/j.cocis.2017.02.004.
- Dressler, H. Resorcinol: Its Uses and Derivatives. In Topics in Applied Chemistry. New York: Plenum Press, 1994.
- Buono, P.; Duval, A.; Avérous, L.; Habibi, Y. Clicking Biobased Polyphenols: A Sustainable Platform for Aromatic Polymeric Materials. ChemSusChem 2018, 11, 2472–2491. DOI: https://doi.org/10.1002/cssc.201800595.
- Setiati, R.; Siregar, S.; Marhaendrajana, T.; Wahyuningrum, D.; Listyani, A. Sustainable Green Chemical Processing of Surfactant Synthesized from Bagasse for Enhanced Oil Recovery Using Microwave Radiation. IOP Conf. Ser.: Mater. Sci. Eng. 2019, 662, 62005.
- Tao, K.; Yang, J.; Xu, G.; Qiu, L. A Method for Producing 2,6-Dimethyl Aniline; Nantong Dongchang Chemical Industrial Co., Ltd., Nantong, 2012; p. 4.
- Zeng, H.; Qiu, Z.; Domínguez-Huerta, A.; Hearne, Z.; Chen, Z.; Li, C.-J. An Adventure in Sustainable Cross-Coupling of Phenols and Derivatives via Carbon-Oxygen Bond Cleavage. ACS Catal. 2017, 7, 510–519. DOI: https://doi.org/10.1021/acscatal.6b02964.
- Rathod, P. V.; Deonikar, V. G.; Puguan, J. M. C.; Kim, H. Synthesis of Biomass-Based Amines: Metal-Free Catalytic Reductive Amination of Xylose and Biomass-Derived Carbonyl Compounds Using Pyridine-Based Ionic Liquid/Triethoxysilane. Fuel 2020, 264, 116822. DOI: https://doi.org/10.1016/j.fuel.2019.116822.
- Zhou, J.; Zeng, R.; Luo, X-g. Research Progress on Chemical Modification of Lignin. Xianweisu Kexue Yu Jishu 2006, 14, 59–66.
- Du, X.; Li, J.; Lindström, M. E. Modification of Industrial Softwood Kraft Lignin Using Mannich Reaction with and without Phenolation Pretreatment. Ind. Crops Prod. 2014, 52, 729–735. DOI: https://doi.org/10.1016/j.indcrop.2013.11.035.
- Jiao, G.-J.; Peng, P.; Sun, S.-L.; Geng, Z.-C.; She, D. Amination of Biorefinery Technical Lignin by Mannich Reaction for Preparing Highly Efficient Nitrogen Fertilizer. Int. J. Biol. Macromol. 2019, 127, 544–554. DOI: https://doi.org/10.1016/j.ijbiomac.2019.01.076.
- Pan, H.; Sun, G.; Zhao, T. Synthesis and Characterization of Aminated Lignin. Int. J. Biol. Macromol. 2013, 59, 221–226. DOI: https://doi.org/10.1016/j.ijbiomac.2013.04.049.
- Dalimova, G. N.; Malikova, M. K. Amination of Hydrolyzed Lignin of Cotton-Seed Husks. Chem. Nat. Compd. 2004, 40, 168–171. DOI: https://doi.org/10.1023/B:CONC.0000033938.09787.0b.
- Basso, M. C.; Lacoste, C.; Pizzi, A.; Fredon, E.; Delmotte, L. MALDI-TOF and 13C NMR Analysis of Flexible Films and Lacquers Derived from Tannin. Ind. Crops Prod. 2014, 61, 352–360. DOI: https://doi.org/10.1016/j.indcrop.2014.07.019.
- Grigsby, W.; Warnes, J. Potential of Tannin Extracts as Resorcinol Replacements in Cold Cure Thermoset Adhesives. Holz Roh. Werkst. 2004, 62, 433–438. DOI: https://doi.org/10.1007/s00107-004-0504-z.
- de Vera, G. A.; Gernjak, W.; Weinberg, H.; Farré, M. J.; Keller, J.; von Gunten, U. Kinetics and Mechanisms of Nitrate and Ammonium Formation during Ozonation of Dissolved Organic Nitrogen. Water Res. 2017, 108, 451–461. DOI: https://doi.org/10.1016/j.watres.2016.10.021.
- Northup, R. R.; Yu, Z.; Dahlgren, R. A.; Vogt, K. A. Polyphenol Control of Nitrogen Release from Pine Litter. Nature 1995, 377, 227–229. DOI: https://doi.org/10.1038/377227a0.
- Zeller, W. E. Activity, Purification, and Analysis of Condensed Tannins: Current State of Affairs and Future Endeavors. Crop Sci. 2019, 59, 886–904. DOI: https://doi.org/10.2135/cropsci2018.05.0323.
- Sepperer, T.; Tondi, G.; Petutschnigg, A.; Young, T. M.; Steiner, K. Mitigation of Ammonia Emissions from Cattle Manure Slurry by Tannins and Tannin-Based Polymers. Biomolecules 2020, 10, 581. DOI: https://doi.org/10.3390/biom10040581.
- Hashida, K.; Makino, R.; Ohara, S. Amination of Pyrogallol Nucleus of Condensed Tannins and Related Polyphenols by Ammonia Water Treatment. Holzforschung 2009, 63, 319–326. DOI: https://doi.org/10.1515/HF.2009.043.
- Thébault, M.; Pizzi, A.; Santiago-Medina, F. J.; Al-Marzouki, F. M.; Abdalla, S. Isocyanate-Free Polyurethanes by Coreaction of Condensed Tannins with Aminated Tannins. J. Renew. Mater. 2017, 5, 21–29. DOI: https://doi.org/10.7569/JRM.2016.634116.
- Braghiroli, F. L.; Fierro, V.; Izquierdo, M. T.; Parmentier, J.; Pizzi, A.; Celzard, A. Nitrogen-Doped Carbon Materials Produced from Hydrothermally Treated Tannin. Carbon 2012, 50, 5411–5420. DOI: https://doi.org/10.1016/j.carbon.2012.07.027.
- Braghiroli, F. L.; Fierro, V.; Izquierdo, M. T.; Parmentier, J.; Pizzi, A.; Delmotte, L.; Fioux, P.; Celzard, A. High Surface – Highly N-Doped Carbons from Hydrothermally Treated Tannin. Ind. Crops Prod. 2015, 66, 282–290. DOI: https://doi.org/10.1016/j.indcrop.2014.11.022.
- Herrick, F. W. Chemistry and Utilization of Western Hemlock Bark Extractives. J. Agric. Food Chem. 1980, 28, 228–237. DOI: https://doi.org/10.1021/jf60228a060.
- Amination reactions were carried out in a Teflon lined stainless steel laboratory reactor (100 mL) fitted with a stirrer bar and immersed in a heated oil bath. Catechin or tannin (0.5 g) was weighed into the reactor liner and briefly vacuum dried before transferring and assembling the reactor. The reactor was evacuated, cooled with a dry ice/acetone bath and adding ammonia (20 g). The reactor was then sealed and heated at the specified temperature and time. After the reaction, the reactor was cooled and then ammonia released before recovering the product and vacuum drying. Full details provided in the Supplementary Materials.
- Braghiroli, F.; Fierro, V.; Pizzi, A.; Rode, K.; Radke, W.; Delmotte, L.; Parmentier, J.; Celzard, A. Reaction of Condensed Tannins with Ammonia. Ind. Crops Prod. 2013, 44, 330–335. DOI: https://doi.org/10.1016/j.indcrop.2012.11.024.
- Ramos-Tejada, M. M.; Durán, J. D. G.; Ontiveros-Ortega, A.; Espinosa-Jimenez, M.; Perea-Carpio, R.; Chibowski, E. Investigation of Alumina/(+)-Catechin System Properties. Part I: A Study of the System by FTIR-UV-Vis Spectroscopy. Colloids Surf. B. 2002, 24, 297–308. DOI: https://doi.org/10.1016/S0927-7765(01)00284-3.
- Grigsby, W. J.; Bridson, J. H.; Schrade, C. Modifying Biodegradable Plastics with Additives Based on Condensed Tannin Esters. J. Appl. Polym. Sci. 2014, 132, 41626. DOI: https://doi.org/10.1002/app.41626.