Lignin-phenol-formaldehyde adhesives with residual. lignin from hardwood bioethanol production
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1 Lignin-phenol-formaldehyde adhesives with residual lignin from hardwood bioethanol production Soo Jung Lee Bioenergy research center at chonnam national university
2 Contents 1. Background 2. Isolation of lignin from saccharification residues 3. Analysis of isolated lignin 4. Lignin-Phenol-formaldehyde adhesives 5. Conclusion
3 Background Utilization? Effective utilization of lignocellulosic biomass feedstock Value-added application for low-cost bioethanol production
4 Characterization of saccharification residue Utilization of saccharification residues as alternative adhesives to replace phenol? Residue -1) Residu e Raw materia l Wavenmber (cm - 1 ) prepared nonliquid high proportion of polysaccharide low reactivity impure lignin
5 Compositional analysis of saccharification residue Yield (%) Chemical composition Holocellulose 37% Organic extractives 11% Monosaccharide composition acid soluble lignin 0.03% Klason Lignin 46% Lignin monomer Lignin monomer composition by Nitrobenzene oxidation(nbo) Hydroxy Benzaldehyde Hydroxy benzoic acid Vanillin Vanillic acid Syringaldehyde Syringic acid S/G ratio Yield (%)
6 Lignin-Structure CH 2 OH Hydroxylphenyl propane CH 2 OH OH Guaiacyl OCH 3 OH CH 2 OH Lignin of beech wood Nimz, H., Angew. Chem., 86 (9), H 3 CO OH Syringyl OCH 3
7 Isolation of lignin in saccharification residues Residue after saccharification of hardwood (Quercus acutissima) Treatment with NaOH Treatment with Ethanol-Water H 2 SO 4 /NaOH Residues Filtrate Residues Filtrate 1. Neutralization 2. Concentration 3. Precipitation 1. Remove ethanol by evaporation 2. Acidified Acid insoluble Lignin (AIL) Hemicellulose, Water-soluble Lignincarbohydrate complex Organosolv Lignin (Acid-OSL/Alkali-OSL)
8 Lignin yield (%)* Yield of isolated lignin * Lignin yield based on klason lignin
9 Phenolic compound (mg GAE/100g sample) Determination of phenolic compound Analysis of isolated lignin by Folin-Ciocalteau method
10 Influence of extraction condition Alkali concnetration (%) for alkali-osl Lignin yield (%) NaOH concentration (%) for AIL Ethanol concentration (%) for OSL
11 Chemical composition of isolated lignin Yield (%) 14 Vanillin Vanillic acid Syringaldehyde 12 Syringic acid AIL Acid-OSL Alkali-OSL Lignin monomer composition of isolated lignin using nitrobenzene oxidation by GC * Yield (%) based on lignin sample weight
12 FTIR-ATR analysis of isolated lignins Alkali-OSL AIL 1460 C-H defoprmantion: aromatic skeletal vibration of benzene ring in lignin Acid-OSL 1505 aromatic skeletal vibration of benzene ring in lignin 1594 C=O stretching conjugated to the aromatic ring AIL Acid-OSL Alkali- OSL (cm-1) Wavenumbers -1 )
13 1H-NMR of isolated lignin using acetylation 1 Aliphatic acetate Acetyl groups in xylan 3 Aromatic acetae 4 H γ, H β, H α in β-o-4 structure 7 Aromatic proton in S- unit 8 Aromatic proton in G-unit 9 Protons in methoxyl groups Residues AIL Acid-OSL ppm
14 Quantitative analysis of isolated lignin Chemical structure of isolated lignins studied by 1 H NMR Sample H G δ H H S δ H OH phen. δ H OH aliph. δ H 2.1 OH ph : OH aliph G:S Residue :61 AIL :63 Acid-OSL :62 Comparison of S/G ratio between methods Comparison of phenolic OH between methods S/G ratio NBO method 1 H-NMR Phenolic OH group UV at 300 nm (%) 1 H-NMR Oak-S-R AIL Acid-OSL Oak-S-R AIL Acid-OSL
15 Bond strength (N/mm 2 ) Performance of adhesives with different lignin Preparation of LPF adhesives Phenol(lignin)/formaldehyde ratio=1:1.5 Mixing : first (phenol+lignin), second (formaldehyde), third (NaOH) Viscosity: mpas Phenol AIL 30% Acid OSL 30% Alkali OSL 30% Residue 30% 110 ± 2 mm 10 ± 0.2 mm
16 Effect of lignin substitution ratios to phenol
17 Thermal properties of adhesives Fig. TG curves of PF and LPF obtained from TGA analysis Table. Thermal behavior of LPF compared to PF Adhesives Phenol- Formaldehyde First thermal event T max ( o C) Second thermal event T max ( o C) Third thermal event T max ( o C) Weight residue (%) % Acid-OSL % Acid-OSL % Acid-OSL % AIL % Alkali OSL
18 FTIR-ATR analysis of LPF-adhesives C-O streching of phenolic OH group 1020 Methylol-OH, aliphatic OH of lignin PF AIL 40% OSL 40% Wav enumbers (cm-1) Wavenumbers (cm -1 )
19 Conclusion Isolation of lignin from saccharification necessary because of low reactivity High yield of lignin obtained using alkaline solution or ethanol at room temperature Acid-OSL has higher phenolic OH group and lower S/G ratio compared AIL, supposed more suitable for lignin-phenol-formaldehyde formulation With the increase of the substitution rate of lignin to phenol decreased bonding strength Replacement up to 10% in AIL and acid-osl showed improved adhesive strength 40% of substitution rate in acid-osl decrease only 25% of strength in PF, greater potential to alternative phenol in production of PF-adhesives
20 Thank you for your attention
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