Abstract
The dominating kraft pulping process leads to kraft pulp and to black liquor (BL), which is incinerated for recovery of inorganic chemicals. A certain part of the BL can also be used as a source of organic chemicals without disturbing the recovery and energy balance of the mill. In this research, the removal of low molecular weight (MW) phenolic products from BL without disturbing the recovery process. Strongly basic anion exchange (AE) resin was utilized to deplete BL from different phenolic derivatives on a preparative scale. The adsorbed low MW phenols can be easily liberated by acidic treatment. Completely depleted BL was then electrochemically treated for further highly selective degradation of kraft lignin. This combined approach enabled the concentration of phenolic substances.
Acknowledgments
The authors thank the Federal Ministry of Food and Agriculture (FKZ 22027208), BASF SE, and the Deutsche Telekom Stiftung for financial support. Providing BL by Dr. Horner (ZPR, Blankenstein, Germany) is highly appreciated.
References
Brodin, I., Sjöholm, E., Gellerstedt, G. (2009) Kraft lignin as feedstock for chemical products: The effects of membrane filtration. Holzforschung 63:290–297.10.1515/HF.2009.049Search in Google Scholar
Caetano, M., Valderrama, C., Farran, A., Cortina, J.L. (2009) Phenol removal from aqueous solution by adsorption and ion exchange mechanisms onto polymeric resins. J. Colloid Interf. Sci. 338:402–409.10.1016/j.jcis.2009.06.062Search in Google Scholar PubMed
Chatel, G., Rogers, R.D. (2014) Review: oxidation of lignin using ionic liquids an innovative strategy to produce renewable chemicals. ACS Sustainable Chem. Eng. 2:322–339.10.1021/sc4004086Search in Google Scholar
Cui, C., Sun, R., Argyropoulos, D.S. (2014) Fractional precipitation of softwood kraft lignin: isolation of narrow fractions common to a variety of lignins. ACS Sustainable Chem. Eng. 2:959–968.10.1021/sc400545dSearch in Google Scholar
Dorfner, K. Ionenaustauscher. De Gruyter, Berlin, 1970.10.1515/9783110836615Search in Google Scholar
Freudenberg, K., Neish, A.C. Constitution and Biosynthesis of Lignin. Springer, New York, 1968.10.1007/978-3-642-85981-6Search in Google Scholar
Gierer, J., Lindeberg O. (1980) Reactions of lignin during sulfate pulping. Part XIX. Isolation and identification of new dimers from a spent sulfate liquor. Acta Chem. Scand. B 34:161–170.10.3891/acta.chem.scand.34b-0161Search in Google Scholar
Kansal, S., Singh, M., Sud, D. (2008) Studies on TiO2/ZnO photocatalysed degradation of lignin. J. Hazard. Mater. 153:412–417.10.1016/j.jhazmat.2007.08.091Search in Google Scholar PubMed
Lange, H., Decina, S., Crestini, C. (2013) Oxidative upgrade of lignin – Recent routes reviewed. Eur. Polym. J. 49:1151–1173.10.1016/j.eurpolymj.2013.03.002Search in Google Scholar
Löwendahl, L., Petersson, G., Samuelson, O.S. (1978) Phenolic compounds in kraft black liquor. Svensk Papperstidn. 81:392–396.Search in Google Scholar
Moreva, Y.L., Alekseeva, N.S., Chernoberezhskii, Y.M.R. (2010) Histograms of the size distribution of kraft lignin particles in aqueous solutions at various pH values. J. Appl. Chem. 83:1281–1283.10.1134/S1070427210070207Search in Google Scholar
Morris, P.C., Welters, P., Garthoff, B. Plants as bioreactors: production and use of plant-derived secondary metabolites, enzymes, and pharmaceutical proteins. In: Renewable raw materials. New feedstocks for the chemical industry. Eds. Ulber, R., Sell, D., Hirth, T. Wiley-VCH, Weinheim, 2011, pp. 13–15.Search in Google Scholar
Norgren, M., Lindström, B. (2000) Dissociation of phenolic groups in kraft lignin at elevated temperatures. Holzforschung 54:519–527.10.1515/HF.2000.088Search in Google Scholar
Pan, K., Tian, M., Jiang, Z.-H., Kjartanson, B., Chen, A. (2012) High-performance liquid chromatography/high-resolution multiple stage tandem mass spectrometry using negative-ion-mode hydroxide-doped electrospray ionization for the characterization of lignin degradation products. Electrochim. Acta 60:147–153.10.1016/j.electacta.2011.11.025Search in Google Scholar
Parpot, P., Bettencourt, A.P., Carvalho, A., Belgsier, E.M. (2000) Biomass conversion: attempted electrooxidation of lignin for vanillin production. J. Appl. Electrochem. 30:727–731.10.1023/A:1004003613883Search in Google Scholar
Partenheimer, W. (2009) The aerobic oxidative cleavage of lignin to produce hydroxyaromatic benzaldehydes and carboxylic acids via metal/bromide catalysts in acetic acid/water mixtures. Adv. Synth. Catal. 351:456–466.10.1002/adsc.200800614Search in Google Scholar
Ralph, J., Lundquist, K., Brunow, G., Lu, F., Kim, H., Schatz, P.F., Marita, J.M., Hatfield, R.D., Ralph, S.A., Christensen, J.H. (2004) Lignins: natural polymers from oxidative coupling of 4-hydroxyphenyl- propanoids. Phytochem. Rev. 3:29–60.10.1023/B:PHYT.0000047809.65444.a4Search in Google Scholar
Reichert, E., Wintringer, R., Volmer, D.A., Hempelmann, R. (2012) Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid. Phys. Chem. Chem. Phys. 14:5214–5221.10.1039/c2cp23596jSearch in Google Scholar PubMed
Schmitt, D., Regenbrecht, C., Hartmer, M., Stecker, F., Waldvogel, S.R. (2015) Highly selective generation of vanillin by anodic degradation of lignin: a combined approach of electrochemistry and product isolation by adsorption. Beilstein J. Org. Chem. 11:473–480.10.3762/bjoc.11.53Search in Google Scholar PubMed PubMed Central
Smith, C.Z., Utley, J.H.P., Hammond, J.K. (2011) Electro-organic reactions. Part 60[1]. The electro-oxidative conversion at laboratory scale of a lignosulfonate into vanillin in an FM01 filter press flow reactor: preparative and mechanistic aspects. J. Appl. Electrochem. 41:363–375.10.1007/s10800-010-0245-0Search in Google Scholar
Tolba, R., Tian, M., Wen, J., Jiang, Z.-H., Chen, A., (2010) Electrochemical oxidation of lignin at IrO2-based oxide electrodes. J. Electroanal. Chem. 649:9–15.10.1016/j.jelechem.2009.12.013Search in Google Scholar
Ulrich, J., Stelzer, T., Niemi, H., Lathi, J., Hatakka, H., Kärki, S., Rovio, S., Kallioinen, M., Mänttäri, M., Louhi-Kultanen, M. (2011) Fractionation of organic and inorganic compounds from Black liquor by combining membrane separation and crystallization. Chem. Eng. Technol. 34:141–148.Search in Google Scholar
Wang, S.-H., McCarthy, J.L., Ferguson, J.F. (1993) Utilization of glucoisosacharinic acid and components of kraft black liquor as energy source for growth of anaerobic bacteria. Holzforschung 47:141–148.10.1515/hfsg.1993.47.2.141Search in Google Scholar
Zhang, Q., Chuang, K.T. (2001) Adsorption of organic pollutants from effluents of a Kraft pulp mill on activated carbon and polymer resin. Adv. Environ. Res. 5:251–258.10.1016/S1093-0191(00)00059-9Search in Google Scholar
Zhu, L., Deng, Y., Zhang, J., Chen, J. (2011) Adsorption of phenol from water by N-butylimidazolium functionalized strongly basic anion exchange resin. J. Colloid Interf. Sci. 364:462–468.10.1016/j.jcis.2011.08.068Search in Google Scholar PubMed
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