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Characterization of Wood-Based Industrial Biorefinery

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Characterization of Wood-Based Industrial Biorefinery Waste and Biomass Valorization (2020) 11:5835–5845 https://doi.org/10.1007/s12649-019-00878-5 ORIGINAL PAPER Characterization of Wood‑based Industrial Biorefnery Lignosulfonates and Supercritical Water Hydrolysis Lignin Venla Hemmilä1 · Reza Hosseinpourpia1 · Stergios Adamopoulos1 · Arantxa Eceiza2 Received: 29 March 2019 / Accepted: 11 November 2019 / Published online: 14 November 2019 © The Author(s) 2019 Abstract Understanding the properties of any particular biorefnery or pulping residue lignin is crucial when choosing the right lignin for the right end use. In this paper, three diferent residual lignin types [supercritical water hydrolysis lignin (SCWH), ammonium lignosulfonate (A-LS), and sodium lignosulfonate (S-LS)] were evaluated for their chemical structure, thermal properties and water vapor adsorption behavior. SCWH lignin was found to have a high amount of phenolic hydroxyl groups and the highest amount of β-O-4 linkages. Combined with a low ash content, it shows potential to be used for conversion into aromatic or platform chemicals. A-LS and S-LS had more aliphatic hydroxyl groups, aliphatic double bonds and C=O structures. All lignins had available C 3/C5 positions, which can increase reactivity towards adhesive precursors. The glass transition temperature (Tg) data indicated that the SCWH and S-LS lignin types can be suitable for production of carbon fbers. Lignosulfonates exhibited considerable higher water vapor adsorption as compared to the SCWH lignin. In conclu- sion, this study demonstrated that the SCWH difered greatly from the lignosulfonates in purity, chemical structure, thermal stability and water sorption behavior. SCWH lignin showed great potential as raw material for aromatic compounds, carbon fbers, adhesives or polymers. Lignosulfonates are less suited for conversion into chemicals or carbon fbers, but due to the high amount of aliphatic hydroxyl groups, they can potentially be modifed or used as adhesives, dispersants, or reinforce- ment material in polymers. For most value-adding applications, energy-intensive purifcation of the lignosulfonates would be required. Graphic Abstract Keywords Ammonium lignosulfonate · Sodium lignosulfonate · Hydrolysis lignin · Phenolics · Aromatics Extended author information available on the last page of the article Vol.:(0123456789)1 3 5836 Waste and Biomass Valorization (2020) 11:5835–5845 Statement of Novelty this, more environmentally friendly solvents are wished for, especially as they enable co-production of a sugar Supercritical water hydrolysis (SCWH) lignin is novel type stream for fermentation. Organosolv and steam explosion of lignin from a biorefnery process that only uses water. processes are more suitable than sulfur-based pulping Because of this, SCWH lignin is closer to its natural state processes in that respect, but the most environmentally than other industrial residual lignin types. In this work, friendly solvent is water. Water above its critical point can the SCWH biorefnery lignin residue has been compared act as the reactant or catalyst for breaking down biomass to another less common biorefnery residual lignin type: [13, 14]. Supercritical water can dissolve and hydrolyze lignosulfonates. Chemical, thermal and vapor sorption lignin for potential production of phenolic chemicals or characterization of the residual lignin types have been for upgrading lignin for fuels [15]. The temperature and done in order to fnd optimal value-added application. reaction time greatly afects the depolymerization pathway and rate of the hydrolysis [16]. Like the chemical pulp- ing processes, the main reactions in supercritical water hydrolysis are cleavage of the β-O-4 linkages and propane Introduction side chains and demethoxylation [17, 18]. Annually, more than 50 million tons of lignin worldwide Utilization of lignocellulosic raw materials provides an are used as a combustion fuel in pulp mills while a very excellent alternative to petroleum based ones, as they are small portion of lignin (around 2 wt%) is used commercially, sustainable, do not compete with food sources, and can mainly in low-value applications [19, 20]. There are three have a positive impact on reduction of global greenhouse pathways to create value-added products from lignin: (i) Due emissions. Value-adding applications are desired espe- to the large amounts of aromatic structures present in lignin, cially for lignins from biorefnery processes, due to the it can be depolymerized into aromatic or platform chemicals. increase in conversion of biomass into transportation fuels Fragmentation of lignin into smaller aromatic compounds that will generate substantially more lignin than necessary ofers a signifcant market potential, but it is less developed to power the operation [1]. than the use of lignin as a macromolecule [21]. (ii) Lignin as Valorization of lignin, however, is challenging due to an unchanged macromolecule is used as additive or polymer its amorphous and robust structure [2]. Besides the origin blend [2]. (iii) Lignin consists of about 50–60% of carbon, of the lignin, the extraction method plays a key role in and can thus be directly used as a precursor for carbon mate- the fnal lignin structure [2–4]. Like other lignin types rials such as activated carbons and carbon fbers [22]. obtained from chemical pulping processes (e.g. kraft Aromatic compounds such as benzene, toluene, xylenes, lignin, and the less common soda and organosolv lignins), phenols and vanilin can be depolymerized from lignin by the lignins from the sulfte process (lignosulfonates) con- combining solvotic extraction with reductive depolymeriza- tain low amount of β-O-4 linkages (less than 10%) and tion [23]. Low molecular weight and high amount of reac- high amounts of C–C bonds [3, 5]. However, unlike kraft tive groups (e.g. carbonyl groups) have a positive impact on and hydrolysis lignin, lignosulfonates are water-soluble the depolymerization process [24]. The amount of β-O-4 over almost the entire pH-range [3] and are currently used linkages in the lignin also correlates closely with the yields as dispersants for various applications [6]. They provide of syringyl, guaiacyl and p-hydroxyphenyl aromatic prod- up to 90% of commercial lignin and have annual world- ucts [25]. However, especially for lignins from chemical wide production of approximately 1.8 million tons [7]. processes, the amount of β-O-4 linkages is typically so Characterization studies have shown that lignosulfonates low, that mild cleavage methods (oxidative, reductive and have high molecular weight and contain high amounts of redox-neutral methods) do not have a major efect [3]. If sulfonate groups. Both of these properties are crucial in depolymerization is desired, conditions capable of breaking determining their dispersing efciency and use for other the C–C bonds, such as pyrolysis, hydrogenolysis and treat- applications [8–11]. Controlling the molecular weight of ment with supercritical water, need to be applied [3]. These lignosulfonates can be done by various techniques, such processes are often less selective and lead to highly complex as separation, depolymerization, and chemical modifca- chemical compositions that need to be further catalytically tion [12]. Characterization studies have led to the partial converted to the desired end-products [26]. Lignin gasifca- elucidation of the structure of lignosulfonates, however tion, for example, depolymerizes the lignin into syngas that much of their overall global structure and shape is still can be used to generate electricity, pure hydrogen, or other not well known. chemicals [2, 3]. Sulfur used in both kraft and sulfte pulping processes, In adhesive, additive and polymer applications, lignin is however, is an environmental concern [2]. Because of used in its macromolecular state [2]. The chemical struc- ture and thermal behavior of lignin determines its suitability 1 3 Waste and Biomass Valorization (2020) 11:5835–5845 5837 towards these diferent applications. The most developed infrared (FTIR) spectroscopy, thermogravimetric analysis adhesive application for lignin is replacement of phenols (TGA), diferential scanning calorimetry (DSC) and auto- in phenol–formaldehyde adhesives [27]. Besides active mated vapor sorption (AVS) analysis. These characteriza- sites, the amount of aliphatic and phenolic hydroxyl groups tions should provide further understanding of the mentioned increase the reactivity of lignin towards synthetic adhesive industrial residual lignin types in order to help developing precursors such as aldehydes, tannins, phenols and isocy- value-added polymers and bioproducts. anates [28, 29]. The number of available reactive groups (e.g. COOH, phenolic and aliphatic hydroxyl groups) also determines the reinforcement efect of lignin in diferent polymer blends. Grafting of lignin is often required to make Materials and Methods it compatible with polymers such as polylactic acid, polypro- pylene, and polyvinyl alcohol [30]. Macromolecular lignin Materials can have several potential functions in polymeric materi- als, such as UV degradation or thermo-oxidation stabilizer, Ammonium lignosulfonate (A-LS) and sodium lignosul- lubricant, hydrophobing agent, plasticizer, adsorbent for fonate (S-LS) samples were obtained as by-products of com- wastewater purifcation or starting material for green hydro- mercial biorefnery processes and received from the sup- gels [31, 32]. plier in dry powder form. Both lignosulfonates were derived In the production of carbon fbers from
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