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Enhancing Lignin Dissolution and Extraction: the Effect of Surfactants polymers Article Enhancing Lignin Dissolution and Extraction: The Effect of Surfactants Elodie Melro 1,* , Artur J. M. Valente 1 , Filipe E. Antunes 1, Anabela Romano 2 and Bruno Medronho 2,3 1 Department of Chemistry, University of Coimbra, CQC, Rua Larga, 3004-535 Coimbra, Portugal; [email protected] (A.J.M.V.); [email protected] (F.E.A.) 2 MED—Mediterranean Institute for Agriculture, Environment and Development, Faculdade de Ciências e Tecnologia, Campus de Gambelas, Universidade do Algarve, Ed. 8, 8005-139 Faro, Portugal; [email protected] (A.R.); [email protected] (B.M.) 3 FSCN, Surface and Colloid Engineering, Mid Sweden University, SE-851 70 Sundsvall, Sweden * Correspondence: [email protected] Abstract: The dissolution and extraction of lignin from biomass represents a great challenge due to the complex structure of this natural phenolic biopolymer. In this work, several surfactants (i.e., non-ionic, anionic, and cationic) were used as additives to enhance the dissolution efficiency of model lignin (kraft) and to boost lignin extraction from pine sawdust residues. To the best of our knowledge, cationic surfactants have never been systematically used for lignin dissolution. It was found that ca. 20 wt.% of kraft lignin is completely solubilized using 1 mol L−1 octyltrimethylammonium bromide aqueous solution. A remarkable dissolution efficiency was also obtained using 0.5 mol L−1 polysorbate 20. Furthermore, all surfactants used increased the lignin extraction with formic acid, even at low concentrations, such as 0.01 and 0.1 mol L−1. Higher concentrations of cationic surfactants improve the extraction yield but the purity of extracted lignin decreases. Citation: Melro, E.; Valente, A.J.M.; Keywords: dissolution; extraction; lignin; lignocellulosic waste; maritime pine; surfactants Antunes, F.E.; Romano, A.; Medronho, B. Enhancing Lignin Dissolution and Extraction: The Effect of Surfactants. Polymers 2021, 13, 714. 1. Introduction https://doi.org/10.3390/ polym13050714 The interaction of surfactants with macromolecules, such as proteins, dates from the early 1950s [1]. This research focusing on these interactions was mainly triggered Academic Editor: Debora Puglia by their biological relevance. Later, synthetic polymers with well-defined characteristics appeared, and research was further extended to other polymer–surfactant systems. Due to Received: 8 February 2021 their uses in different applications, such as cosmetics, paints, foods, detergents, pesticides, Accepted: 22 February 2021 and pharmaceutics, polymer–surfactant systems have received a lot of attention in the last Published: 26 February 2021 several decades [2,3]. The combination of polymers and surfactants can offer myriad effects, such as controlling interfacial properties, network formation, and rich phase behavior. The Publisher’s Note: MDPI stays neutral latter effect is particularly relevant in the context of the solubilization of water-insoluble with regard to jurisdictional claims in polymers [4]. Lignin is an example of a polymer that is insoluble in water and many other published maps and institutional affil- traditional solvents. This complex polyphenolic biopolymer is considered the second most iations. available macromolecule on Earth and works as a “natural glue,” holding together cellulose and hemicellulose in the fibers of plant cell walls [5]. Lignin possesses great potential to obtain value-added compounds, but its uses are still scarce; lignin is mainly burnt for energy generation purposes [6]. As mentioned, lignin dissolution is complicated but frequently Copyright: © 2021 by the authors. required as a first step for several applications. Despite the dissolution limitations, several Licensee MDPI, Basel, Switzerland. solvent systems have been successfully developed [7]. In some cases, different additives This article is an open access article have proven to enhance lignin dissolution [8]. In this respect, surfactants are typically good distributed under the terms and candidates to improve polymer solubilization, since their association with macromolecules conditions of the Creative Commons can turn them more hydrophilic, decrease hydrophobic interactions, introduce charges, Attribution (CC BY) license (https:// etc. Surfactant (and polymer) properties, such as hydrophobicity, chain flexibility, charge creativecommons.org/licenses/by/ density, and ionic strength, are expected to affect the binding and aggregation phenomena, 4.0/). Polymers 2021, 13, 714. https://doi.org/10.3390/polym13050714 https://www.mdpi.com/journal/polymers Polymers 2021, 13, x FOR PEER REVIEW 2 of 14 Polymers 2021, 13, 714 2 of 13 interactions, introduce charges, etc. Surfactant (and polymer) properties, such as hydro- phobicity, chain flexibility, charge density, and ionic strength, are expected to affect the binding and aggregation phenomena, and even control the dissolution process [9]. De- andspite even being control appealing, the dissolution surfactant process application [9]. Despite in lignin being dissolution appealing, has surfactant been surprisingly application inscarce. lignin Among dissolution the few has reports, been surprisingly Xu et al. ha scarce.ve demonstrated Among the fewthe enhancement reports, Xu et of al. lignin have demonstrateddissolution in aqueous-based the enhancement systems of lignin containing dissolution the in nonionic aqueous-based surfactant systems tween containing 80 [10]. In theanother nonionic work, surfactant Norgren tweenet al. have 80 [10 used]. In bile another acid work,salts (a Norgren special class et al. of have biological used bile surfac- acid saltstants) (a to special successfully classof increase biological the solubility surfactants) and to colloidal successfully stability increase of kraft the lignin solubility [11]. andThe colloidalsearch for stability efficient of lignin kraft lignin extraction [11]. Themethods search is for a topic efficient of great lignin scientific extraction and methods industrial is a topicinterest. of great Lignin scientific is an effective and industrial source interest.of biomass, Lignin with is anenzymatic effective hydrolysis source of biomass, being key with to enzymaticits use [12,13]. hydrolysis In lignocellulosic being key to biomass its use [12 pr,13ocessing,]. In lignocellulosic non-ionic biomasssurfactants processing, are typically non- ionicused surfactantsto enhance arelignin typically extraction used [14,15]. to enhance These lignin surfactants extraction play [14 the,15 ].role These of additives surfactants in playthe soda the rolepulping of additives of bagasse in the [16] soda and pulping increase of the bagasse yield [of16 kraft] and lignin increase removal the yield in the of kraft pre- lignincipitation removal step [17]. in the Non-charged precipitation surfactants, step [17]. Non-charged mainly the tween-type, surfactants, are mainly important the tween- in en- type,zymatic are hydrolysis, important inand enzymatic thus are widely hydrolysis, used andfor the thus conversion are widely of used lignocellulosic for the conversion biomass ofinto lignocellulosic bioethanol. Other biomass surfactant into bioethanol. systems have Other been surfactant reported systems to assist have the beenenzymatic reported hy- todrolysis assist in the different enzymatic lignocellulosic hydrolysis inbiomass different matrixes lignocellulosic [18–26]. During biomass these matrixes processes, [18– 26lig-]. Duringnin acts these as a physical processes, barrier lignin to acts the as enzymes a physical and barrier can even to the absorb enzymes them and via can strong even interac- absorb them via strong interactions (hydrophobic, electrostatic, and hydrogen-bonding) [27,28]. tions (hydrophobic, electrostatic, and hydrogen-bonding) [27,28]. Surfactants facilitate the Surfactants facilitate the access of the enzyme to cellulose by removing the lignin [18]. access of the enzyme to cellulose by removing the lignin [18]. The presence of surfactants The presence of surfactants not only may increase the reaction yield but also allows a not only may increase the reaction yield but also allows a substantial reduction in the substantial reduction in the amount of needed enzyme (up to ca. 50%), while maintaining a amount of needed enzyme (up to ca. 50%), while maintaining a superior yield [23]. The superior yield [23]. The surfactant efficiency in lignin removal can be influenced by several surfactant efficiency in lignin removal can be influenced by several factors, such as its factors, such as its critical micelle concentration (CMC) [22], the chemical and molar mass critical micelle concentration (CMC) [22], the chemical and molar mass properties of lignin properties of lignin [8], hydrolysis conditions [28], and substrate type [29]. [8], hydrolysis conditions [28], and substrate type [29]. To our knowledge, charged surfactants have never been used to dissolve lignin. To our knowledge, charged surfactants have never been used to dissolve lignin. Thorough studies comparing several classes of surfactants are lacking. Therefore, in the Thorough studies comparing several classes of surfactants are lacking. Therefore, in the first part of this study, different cationic and anionic surfactants (Figure1) were used in an first part of this study, different cationic and anionic surfactants (Figure 1) were used in aqueous solution to dissolve model kraft lignin. Non-ionic surfactants were also tested for comparison.an aqueous solution In this first to dissolve part, the model interaction kraft lig betweennin. Non-ionic
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