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Lignin for Bioeconomy: the Present and Future Role of Technical Lignin

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Lignin for Bioeconomy: the Present and Future Role of Technical Lignin International Journal of Molecular Sciences Review Lignin for Bioeconomy: The Present and Future Role of Technical Lignin Adam Ekielski 1,† and Pawan Kumar Mishra 2,*,† 1 Department of Production Engineering, Warsaw University of Life Sciences, 02-776 Warsaw, Poland; [email protected] 2 Faculty of Business and Economics, Mendel University in Brno, 61300 Brno, Czech Republic * Correspondence: [email protected] † These authors contributed equally to this work. Abstract: Lignin, the term commonly used in literature, represents a group of heterogeneous aro- matic compounds of plant origin. Protolignin or lignin in the cell wall is entirely different from the commercially available technical lignin due to changes during the delignification process. In this paper, we assess the status of lignin valorization in terms of commercial products. We start with existing knowledge of the lignin/protolignin structure in its native form and move to the technical lignin from various sources. Special attention is given to the patents and lignin-based commercial products. We observed that the technical lignin-based commercial products utilize coarse properties of the technical lignin in marketed formulations. Additionally, the general principles of polymers chemistry and self-assembly are difficult to apply in lignin-based nanotechnology, and lignin-centric investigations must be carried out. The alternate upcoming approach is to develop lignin-centric or lignin first bio-refineries for high-value applications; however, that brings its own technological challenges. The assessment of the gap between lab-scale applications and lignin-based commercial products delineates the challenges lignin nanoparticles-based technologies must meet to be a commercially viable alternative. Keywords: lignin; technical lignin; self-assembly; lignin nanoparticles; lignin; bioeconomy Citation: Ekielski, A.; Mishra, P.K. Lignin for Bioeconomy: The Present 1. Introduction and Future Role of Technical Lignin. Int. J. Mol. Sci. 2021, 22, 63. https:// Technical lignin refers to the “native-lignin” or “proto-lignin” derivative obtained dx.doi.org/10.3390/ijms22010063 as the result of the delignification process of the lignocellulosic-biomass [1]. The tech- nical lignin structure can vary with the process and chemical reactions utilized in the Received: 8 December 2020 biomass/starting material treatment [2]. Traditionally, technical lignin has been obtained Accepted: 19 December 2020 as a by-product of paper mills wherein the revenue is primarily generated by the cellulose- Published: 23 December 2020 based products, and therefore every process has been optimized to maximize the qualitative and quantitative yield of the cellulose [3]. The recent progress in technology and the arrival Publisher’s Note: MDPI stays neu- of “lignin-centric biorefinery” or “lignin-first biorefinery” is a welcomed addition to the tral with regard to jurisdictional claims biomass treatment strategies. It has renewed the interest in lignin from “valorization” to in published maps and institutional “application” approaches [4–7]. It has also provided an impetus to the search for struc- affiliations. turally homogeneous lignin that can be easily applied in efficient and scalable technology for lignin-based reagents production [8]. The relatively new addition in lignin-based clean (biocompatible and non-toxic) products include nanomaterials and those used in biomedi- Copyright: © 2020 by the authors. Li- cal applications [9–11]. As presented in Figure1, a multi-fold rise in the number of patents censee MDPI, Basel, Switzerland. This registered in the Scopus database in the period of the last 20 years (2000–2019) can be seen. article is an open access article distributed The maximum number of patents were registered in the United States Patent and Trade- under the terms and conditions of the mark Office (45,268), followed by the Japan Patent Office (16,547), the World Intellectual Creative Commons Attribution (CC BY) property organization (10,657), the European Patent office (8180) and the United Kingdom license (https://creativecommons.org/ Intellectual Property office (332). These results were obtained from the Scopus database licenses/by/4.0/). Int. J. Mol. Sci. 2021, 22, 63. https://dx.doi.org/10.3390/ijms22010063 https://www.mdpi.com/journal/ijms Int. J. Mol. Sci. 2021, 22, 63 2 of 24 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 2 of 23 fromwith the Scopus keyword database “lignin”. with It reflectsthe keyword the commercial “lignin”. It relevance reflects the of commercial lignin-based relevance research ofand lignin-based development research of technology and development for its high–value of technology utilization. for its high–value utilization. Figure 1. Number of patents registered in diff differenterent agencies and the nu numbermber of total patents in the duration of 2000–2019 (Results were obtained from thethe ScopusScopus databasedatabase usingusing thethe keywordkeyword “lignin”).“lignin”). TechnicalTechnical lignin is derived mainly from lignocellulosic biomass, and therefore its structurestructure directly directly depends depends on on the the source source and and method of of extraction. Once Once the the lignin lignin (pro- (pro- tolignin/nativetolignin/native lignin) lignin) leaves leaves the the cell cell wall wall (extracted), (extracted), its its structure structure completely completely changed; changed; however,however, monomers monomers can can still still be be identified. identified. The The lignin lignin monomers monomers include include p-coumarylp-coumaryl al- cohol,alcohol, coniferyl coniferyl alcohol, alcohol, and and sinapyl sinapyl alcohol, alcohol, bearing bearing p-hydroxyphenylp-hydroxyphenyl (H), (H),guaiacyl guaiacyl (G), and(G), syringyl and syringyl (S) units, (S) units, as represented as represented in Figure in Figure 2. The2 .source-dependent The source-dependent variation variation in lignin in canlignin be canobserved be observed in herbaceous in herbaceous crop-based crop-based (rich in (rich H units), in H units), gymnosperm/softwood gymnosperm/softwood (lack- ing(lacking S units), S units), and andangiosperm/hardwood angiosperm/hardwood (rich (rich in G in and G andS) lignin S) lignin [1,12] [1,.12 The]. The variation variation in monomersin monomers composition composition is issupported supported by by variation variation in in nature nature and and the the extent extent of of chemical bonding.bonding. Different Different bonds bonds observed observed in inlignin, lignin, along along with with their their numbering numbering system, system, are pre- are sentedpresented in Figure in Figure 3. The3. Theβ -O-4β-O-4 linkage linkage represents represents the most the mostdominant dominant linkage linkage of all ofthree all (softwood,three (softwood, hardwood, hardwood, and grasses) and grasses) types of types sources; of sources; however, however, their comparative their comparative content followscontent the follows order the grasses order > grasseshardwood > hardwood > softwood. > The softwood. two diastereomers, The two diastereomers, the erythro and the threoerythro forms and threoof β -O-4 forms linkage, of β-O-4 can linkage, be found can in be nature. found inThe nature. softwood The softwoodlignin has lignin approxi- has matelyapproximately the same the amount same amountof both forms; of both the forms; erythro the erythroform is formprevalent is prevalent in hardwood in hardwood lignin. Thelignin. quantification The quantification of the two of theforms two (ratio forms and (ratio total and amount) total amount) of these of two these forms two can forms be donecan be by done ozonation by ozonation that leads that to leadsthe formatio to the formationn erythronic erythronic (from erythro (from form) erythro and form) threonic and threonic (from threo form) acid, respectively [13]. The β-O-4 linkage is also the most easily (from threo form) acid, respectively [13]. The β -O-4 linkage is also the most easily affected affected bonding in the lignin by different treatment methods. Despite the relatively lesser bonding in the lignin by different treatment methods. Despite the relatively lesser number number of β-O-4 linkage, the softwood lignin is primarily composed of coniferyl alcohol, of β -O-4 linkage, the softwood lignin is primarily composed of coniferyl alcohol, highly highly condensed and a higher number of C-C bonds, 50 linkages, β-β, and β-5 bonds, condensed and a higher number of C-C bonds, 5′ linkages, β-β, and β-5 bonds, cross-link- cross-linking, and branching. These properties make softwood challenging to degrade ing, and branching. These properties make softwood challenging to degrade and rela- and relatively more resistant to chemical treatments (Table1). Another aromatic material tively more resistant to chemical treatments (Table 1). Another aromatic material (not a (not a lignin derivative) found in pulp analysis is termed pseudolignin. It consists of lignin derivative) found in pulp analysis is termed pseudolignin. It consists of aliphatic and aromatic groups (methoxyl, carboxyl, and carbonyl groups) of non-lignin origin. Int. J. Mol. Sci. 2021, 22, 63 3 of 24 Int. J. Mol. Sci. 2020, 21, x FOR PEER REVIEW 3 of 23 Int. J. Mol. Sci. aliphatic2020, 21, x FOR and PEER aromatic REVIEW groups (methoxyl, carboxyl, and carbonyl groups) of non-lignin 3 of 23 origin.Pseudolignin Pseudolignin has also has been also observed been observed in pulp obtained in pulp by obtained steam explosion by steam and explosion dilute acid and dilutehydrolysis
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