Abstract
Liquefaction of wood-based biomass gives different polyol properties depending on the reagents used. In this article, alder wood sawdust was liquefied with glycerol and poly(ethylene glycol) solvents. Liquefaction reactions were carried out at temperatures of 120, 150 and 170 °C. The obtained bio-polyols were analyzed in order to establish the process efficiency, hydroxyl number, acid value, viscosity and structural characteristics using Fourier transform infrared (FTIR), carbon (13C) and proton (1H) NMR analyses. The results indicate that the optimal conditions for the liquefaction process are at 150 °C for 6 h. The results of the FTIR spectra analysis and the hydroxyl number in the range of 214–687 mg KOH/g showed that the obtained bio-polyols are a potential substitute for petrochemical polyols commonly used for the synthesis of polyurethane polymers. Polyurethane resins containing 90 wt% of bio-polyol were obtained by a one-step method using a hydraulic press. The material was pressed for 15 min (5 MPa) at 100 °C with an NCO/OH ratio in the range of 0.9–1.2. Dynamic mechanical thermal analysis (DMA) showed high cross-linking density and modulus of elasticity in a wide range of 62–1362 MPa.
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Abdel Hakim AA, Nassar M, Emam A, Sultan M (2015) Mater Chem Phys 129:301–307. https://doi.org/10.1016/j.matchemphys.2011.04.008
Amran UA, Zakaria S, Chia CH et al (2019) Polyols and rigid polyurethane foams derived from liquefied lignocellulosic and cellulosic biomass. Cellulose. https://doi.org/10.1007/s10570-019-02271-w
Behrendt F, Neubauer Y, Oevermann M et al (2012) European Psychiatric Association (EPA) guidance on suicide treatment and prevention. Eur Psychiatry 27(2):129–677. https://doi.org/10.1002/ceat.200800077
Budarin VL, Clark JH, Lanigan BA et al (2010) Microwave assisted decomposition of cellulose: a new thermochemical route for biomass exploitation. Bioresour Technol 101:3776–3779. https://doi.org/10.1016/j.biortech.2009.12.110
Budija F, Tavzes Č, Zupančič-Kralj L, Petrič M (2009) Self-crosslinking and film formation ability of liquefied black poplar. Bioresour Technol 100(2):(2):3316–3323–3323. https://doi.org/10.1016/j.biortech.2009.02.004
Cai Z, Gao J, Li X, Xiang B (2007) Synthesis and characterization of symmetrical benzodifuranone compounds with femtosecond time-resolved degenerate four-wave mixing technique. Opt Commun 272:503–508. https://doi.org/10.1016/j.optcom.2006.11.056
Calvo-Correas T, Gabilondo N, Alonso-Varona A et al (2016) Shape-memory properties of crosslinked biobased polyurethanes. Eur Polym J 78:253–263. https://doi.org/10.1016/j.eurpolymj.2016.03.030
Carballo-Meilan A, Goodman AM, Baron MG, Gonzalez-Rodriguez J (2014) A specific case in the classification of woods by FTIR and chemometric : discrimination of Fagales from Malpighiales. Cellulose 21:261–273. https://doi.org/10.1007/s10570-013-0093-2
Chaikumpollert O, Methacanon P, Suchiva K (2004) Structural elucidation of hemicelluloses from Vetiver grass. Carbohydr Polym 57:191–196. https://doi.org/10.1016/j.carbpol.2004.04.011
Chen F, Lu Z (2009) Liquefaction of wheat straw and preparation of rigid polyurethane foam from the liquefaction products. J Appl Polym Sci 111:508–516. https://doi.org/10.1002/app.29107
Collier WE, Schultz TP, Kalasinsky VF (1992) Infrared study of lignin: reexamination of aryl-alkyl ether C—O stretching peak assignments. Holzforschung 46:523–528. https://doi.org/10.1515/hfsg.1992.46.6.523
D’Souza J, Yan N (2013) Producing bark-based polyols through liquefaction: effect of liquefaction temperature. ACS Sustain Chem Eng 1:534–540. https://doi.org/10.1021/sc400013e
Daneshvar S, Behrooz R, Najafi SK et al (2019) Characterization of polyurethane wood adhesive prepared from liquefied sawdust by ethylene carbonate. BioResour 14:796–815. https://doi.org/10.15376/biores.14.1.796-815
Delebecq E, Pascault J-P, Boutevin B, Ganachaud F (2013) On the versatility of urethane/urea bonds: reversibility, blocked isocyanate, and non-isocyanate polyurethane. Chem Rev 113:80–118. https://doi.org/10.1021/cr300195n
De Oliveira F, Ramires EC, Frollini E, Belgacem MN (2015) Lignopolyurethanic materials based on oxypropylated sodium lignosulfonate and castor oil blends. Ind Crops Prod 72:77–86. https://doi.org/10.1016/j.indcrop.2015.01.023
Deng S, Ting Y-P (2005) Characterization of PEI-modified biomass and biosorption of Cu(II), Pb(II) and Ni(II). Water Res 39:2167–2177. https://doi.org/10.1016/j.watres.2005.03.033
Gaikwad MS, Gite VV, Mahulikar PP et al (2015) Eco-friendly polyurethane coatings from cottonseed and karanja oil. Prog Org Coat 86:164–172. https://doi.org/10.1016/j.porgcoat.2015.05.014
Hassan EM, Shukry N (2007) Polyhydric alcohol liquefaction of some lignocellulosic agricultural residues. Ind Crops Prod 7:33–38. https://doi.org/10.1016/j.indcrop.2007.07.004
Heredia-Guerrero JA, Benítez JJ, Domínguez E et al (2014) Infrared and Raman spectroscopic features of plant cuticles: a review. Front Plant Sci 5:1–15. https://doi.org/10.3389/fpls.2014.00305
Hu S, Wan C, Li Y (2012) Production and characterization of biopolyols and polyurethane foams from crude glycerol based liquefaction of soybean straw. Bioresour Technol 103:227–233. https://doi.org/10.1016/j.biortech.2011.09.125
Hu S, Luo X, Li Y (2014) Polyols and polyurethanes from the liquefaction of lignocellulosic biomass. Chemsuschem 7:66–72. https://doi.org/10.1002/cssc.201300760
Jasiukaityte-Grojzdek E, Kunaver M, Crestini C (2012) Lignin structural changes during liquefaction in acidified ethylene glycol. J Wood Chem Technol 32:342–360. https://doi.org/10.1080/02773813.2012.698690
Javni I, Petrović ZS, Guo A, Fuller R (2000) Thermal stability of polyurethanes based on vegetable oils. J Appl Polym Sci 77:1723–1734. https://doi.org/10.1002/1097-4628(20000822)77:8%3c1723:AID-APP9%3e3.0.CO;2-K
Jin Y, Ruan X, Cheng X, Lü Q (2011) Liquefaction of lignin by polyethyleneglycol and glycerol. Bioresour Technol 102:3581–3583. https://doi.org/10.1016/j.biortech.2010.10.050
Kobayashi M, Asano T, Kajiyama M, Tomita B (2004) Analysis on residue formation during wood liquefaction with polyhydric alcohol. J Wood Sci 50:407–414. https://doi.org/10.1007/s10086-003-0596-9
Kong X, Liu G, Curtis JM (2011) Characterization of canola oil based polyurethane wood adhesives. Int J Adhes Adhes 31:559–564. https://doi.org/10.1016/j.ijadhadh.2011.05.004
Kržan A, Kunaver M, Tišler V (2005) Wood liquefaction using dibasic organic acids and glycols. Acta Chim Slov 52:253–258
Kunaver M, Jasiukaityte E, Čuk N, Guthrie JT (2010) Liquefaction of wood, synthesis and characterization of liquefied wood polyester derivatives. J Appl Polym Sci 115:1265–1271. https://doi.org/10.1002/app.31277
Kurimoto Y, Doi S, Tamura Y (1999) Species effects on wood-liquefaction in polyhydric alcohols. Holzforschung 53:617–622. https://doi.org/10.1515/HF.1999.102
Kurimoto Y, Takeda M, Koizumi A et al (2000) Mechanical properties of polyurethane films prepared from liquefied wood with polymeric MDI. Bioresour Technol 74:151–157. https://doi.org/10.1016/S0960-8524(00)00009-2
Kurimoto Y, Koizumi A, Doi S et al (2001) Wood species effects on the characteristics of liquefied wood and the properties of polyurethane films prepared from the liquefied wood. Biomass Bioenerg 21:381–390. https://doi.org/10.1016/S0961-9534(01)00041-1
Lee W-J, Chao C-Y (2018) Effect of containing polyhydric alcohol liquefied wood on the properties of thermoplastic polyurethane resins. Eur J Wood Prod 76:1745–1752. https://doi.org/10.1007/s00107-018-1338-4
Lee W, Lin M (2008) Preparation and application of polyurethane adhesives made from polyhydric alcohol liquefied Taiwan acacia and China fir. J Appl Polym Sci 109:23–31. https://doi.org/10.1002/app.28007
Lee S-H, Yoshioka M, Shiraishi N (2000) Liquefaction of corn bran (CB) in the presence of alcohols and preparation of polyurethane foam from its liquefied polyol. J Appl Polym Sci 78:319–325. https://doi.org/10.1002/1097-4628(20001010)78:2%3c319:AID-APP120%3e3.0.CO;2-Z
Lee SH, Teramoto Y, Shiraishi N (2002) Acid-catalyzed liquefaction of waste paper in the presence of phenol and its application to Novolak-type phenolic resin. J Appl Polym Sci 83:1473–1481. https://doi.org/10.1002/app.10038
Lee CS, Ooi TL, Chuah CH, Ahmad S (2007) Synthesis of palm oil-based diethanolamides. J Am Oil Chem Soc 84:945–952. https://doi.org/10.1007/s11746-007-1123-8
Lee W, Kuo E-S, Chao C-Y, Kao Y-P (2015) Properties of polyurethane (PUR) films prepared from liquefied wood (LW) and ethylene glycol (EG). Holzforschung 69:547–554. https://doi.org/10.1515/hf-2014-0142
Li H, Xu C, Yuan Z, Wei Q (2018) Synthesis of bio-based polyurethane foams with liquefied wheat straw: process optimization. Biomass Bioenergy 111:134–140. https://doi.org/10.1016/j.biombioe.2018.02.011
Li H, Feng S, Yuan Z et al (2017) Highly efficient liquefaction of wheat straw for the production of bio-polyols and bio-based polyurethane foams. Ind Crop Prod 109:426–433. https://doi.org/10.1016/j.indcrop.2017.08.060
Lu X, Wang Y, Zhang Y et al (2016) Preparation of bio-polyols by liquefaction of hardwood residue and their application in the modification of polyurethane foams. J Wuhan Univ Technol Sci Ed 31:918–924. https://doi.org/10.1007/s11595-016-1468-7
Luo X, Hu S, Zhang X, Li Y (2013) Thermochemical conversion of crude glycerol to biopolyols for the production of polyurethane foams. Bioresour Technol 139:323–329. https://doi.org/10.1016/j.biortech.2013.04.011
Mori R (2015) Inorganic–organic hybrid biodegradable polyurethane resin derived from liquefied Sakura wood. Wood Sci Technol 49:507–516. https://doi.org/10.1007/s00226-015-0707-y
Ni B, Yang L, Wang C et al (2010) Synthesis and thermal properties of soybean oil-based waterborne polyurethane coatings. J Therm Anal Calorim 100:239–246. https://doi.org/10.1007/s10973-009-0418-4
Pan X, Webster DC (2012) New biobased high functionality polyols and their use in polyurethane coatings. Chemsuschem 5:419–429. https://doi.org/10.1002/cssc.201100415
Ristić IS, Budinski-Simendić J, Krakovsky I et al (2012) The properties of polyurethane hybrid materials based on castor oil. Mater Chem Phys 132:74–81. https://doi.org/10.1016/j.matchemphys.2011.10.053
Ruppert AM, Meeldijk JD, Kuipers BWM et al (2016) Glycerol etherification over highly active cao-based materials: new mechanistic aspects and related colloidal particle formation. Chem A Eur J 14:2016–2024. https://doi.org/10.1002/chem.200701757
Saidur R, Abdelaziz EA, Demirbas A et al (2011) A review on biomass as a fuel for boilers. Renew Sustain Energy Rev 15:2262–2289. https://doi.org/10.1016/j.rser.2011.02.015
Sequeiros A, Serrano L, Briones R, Labidi J (2013) Lignin liquefaction under microwave heating. Appl Polym. https://doi.org/10.1002/app.39577
Stefanidis SD, Kalogiannis KG, Iliopoulou EF et al (2014) A study of lignocellulosic biomass pyrolysis via the pyrolysis of cellulose, hemicellulose and lignin. J Anal Appl Pyrolysis 105:143–150. https://doi.org/10.1016/j.jaap.2013.10.013
Tavares LB, Boas CV, Schleder GR et al (2016) Bio-based polyurethane prepared from Kraft lignin and modified castor oil. Express Polym Lett 10:927–940. https://doi.org/10.3144/expresspolymlett.2016.86
Taylor P, Petrovi ZS (2008) Polyurethanes from vegetable oils. Polym Rev 48:37–41. https://doi.org/10.1080/15583720701834224
Trovati G, Sanches EA, De SSM et al (2014) Rigid and semi rigid polyurethane resins: a structural investigation using DMA, SAXS and Le Bail method. J Mol Struct 1075:589–593. https://doi.org/10.1016/j.molstruc.2014.07.024
Wang H, Chen H (2007) A novel method of utilizing the biomass resource: rapid liquefaction of wheat straw and preparation of biodegradable polyurethane foam (PUF). J Chin Inst Chem Eng 38:95–102. https://doi.org/10.1016/j.jcice.2006.10.004
Wang Y, Wu J, Wan Y et al (2009) Liquefaction of corn stover using industrial biodiesel glycerol. Int J Agric Biol Eng 2:32–40. https://doi.org/10.3965/j.issn.1934-6344.2009.02.032-040
Wang H, Ni Y, Jahan MS et al (2011) Stability of cross-linked acetic acid lignin-containing polyurethane. J Therm Anal Calorim 103:293–302. https://doi.org/10.1007/s10973-010-1052-x
Wei Y, Cheng F, Li H, Yu J (2004) Synthesis and properties of polyurethane resins based on liquefied wood. J Appl Polym Sci 92:351–356. https://doi.org/10.1002/app.20023
Xu F, Sun JX, Liu CF, Sun RC (2006) Comparative study of alkali- and acidic organic solvent-soluble hemicellulosic polysaccharides from sugarcane bagasse. Carbohydr Res 341:253–261. https://doi.org/10.1016/j.carres.2005.10.019
Xue B, Wen J, Sun R (2015) Producing lignin-based polyols through microwave-assisted liquefaction for rigid polyurethane foam production. Materials (Basel) 8:586–599. https://doi.org/10.3390/ma8020586
Yao Y, Yoshioka M, Shiraishi N (1996) Water-absorbing polyurethane foams from liquefied starch. J Appl Polym Sci 60:1939–1949. https://doi.org/10.1002/(SICI)1097-4628(19960613)60:11%3c1939:AID-APP18%3e3.0.CO;2-W
Ye L, Zhang J, Zhao J, Tu S (2014) Liquefaction of bamboo shoot shell for the production of polyols. Bioresour Technol 153:147–153. https://doi.org/10.1016/j.biortech.2013.11.070
Yue D, Oribayo O, Rempel GL, Pan Q (2017) Liquefaction of waste pine wood and its application in the synthesis of a flame retardant polyurethane foam. RSC Adv 7:30334–30344. https://doi.org/10.1039/C7RA03546B
Zhang Y, Ikeda A, Hori N et al (2006) Characterization of liquefied product from cellulose with phenol in the presence of sulfuric acid. Bioresour Technol 97:313–321. https://doi.org/10.1016/j.biortech.2005.02.019
Zhang T, Zhou Y, Liu D, Petrus L (2007) Qualitative analysis of products formed during the acid catalyzed liquefaction of bagasse in ethylene glycol. Bioresour Technol 98:1454–1459. https://doi.org/10.1016/j.biortech.2006.03.029
Zhang H, Ding F, Luo C et al (2012) Liquefaction and characterization of acid hydrolysis residue of corncob in polyhydric alcohols. Ind Crop Prod 39:47–51. https://doi.org/10.1016/j.indcrop.2012.02.010
Zhao Y, Yan N, Feng M (2012) Polyurethane foams derived from liquefied mountain pine beetle-infested barks. J Appl Polym Sci 123:2849–2858. https://doi.org/10.1002/app.34806
Zou X, Qin T, Huang L et al (2009) Mechanisms and main regularities of biomass liquefaction with alcoholic solvents. Energy Fuels 23:5213–5218. https://doi.org/10.1021/ef900590b
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Gosz, K., Kowalkowska-Zedler, D., Haponiuk, J. et al. Liquefaction of alder wood as the source of renewable and sustainable polyols for preparation of polyurethane resins. Wood Sci Technol 54, 103–121 (2020). https://doi.org/10.1007/s00226-019-01152-6
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DOI: https://doi.org/10.1007/s00226-019-01152-6