Advertisement

Cellulose

pp 1–16 | Cite as

Polyols and rigid polyurethane foams derived from liquefied lignocellulosic and cellulosic biomass

  • Umar Adli Amran
  • Sarani ZakariaEmail author
  • Chin Hua Chia
  • Rasidi Roslan
  • Sharifah Nabihah Syed Jaafar
  • Kushairi Mohd Salleh
Original Research
  • 34 Downloads

Abstract

Liquefaction of lignocellulosic and cellulosic biomasses produces different polyol properties. Hence, direct comparative studies on the properties of both biomass liquefaction-derived polyols and polyurethane foams (PUFs) have been extensively performed. Optimization of oil palm empty fruit bunch fiber (EFB) and EFB-based cellulose (EFBC) liquefactions was performed in cosolvent polyethylene glycol–glycerol to produce polyols. Hydroxyl (OH) and acid numbers, viscosity, molecular weight, and chemical functionalities of the polyols were analyzed and compared. The optimum liquefaction temperature for both EFB and EFBC was 175 °C. However, the optimum liquefaction time of EFBC (180 min) was longer than the time recorded by EFB (90 min). Liquefaction temperature and time had influenced degradation and recondensation of liquefied biomass products, hence affected the properties of polyols. Extreme degradation and recondensation during liquefaction had reduced the OH number of polyols. Recondensation significantly affected the molecular weight and viscosity of the EFB polyol, but not those of EFBC polyol. Rigid PUFs synthesized from the optimum EFB and EFBC polyols were denoted as EFB PUF and EFBC PUF, respectively. EFB PUF possessed larger average cell diameter than that of EFBC PUF. Comparatively, the thermal decomposition and compressive strength of EFB PUF were lower than those of EFBC PUF.

Graphical abstract

Keywords

Cellular morphology Compressive Hydroxyl and acid numbers Oil palm empty fruit bunch Thermal properties 

Notes

Acknowledgments

This study was financed by Universiti Kebangsaan Malaysia (UKM), Universiti Malaysia Pahang (UMP) and Malaysian Ministry of Higher Education (MOHE) via research grants [Grant Numbers AP-2015-005 (from UKM), DIP-2016-004 (from UKM) and RDU160329 (from UMP)]. The authors gratefully acknowledge the instrumental services provided by the Center for Research and Instrumentation Management (CRIM), UKM.

References

  1. Abdel Hakim AA, Nassar M, Emam A, Sultan M (2011) Preparation and characterization of rigid polyurethane foam prepared from sugar-cane bagasse polyol. Mater Chem Phys 129:301–307.  https://doi.org/10.1016/j.matchemphys.2011.04.008 CrossRefGoogle Scholar
  2. Akindoyo JO, Beg MDH, Ghazali S, Islam MR, Jeyaratnam N, Yuvaraj AR (2016) Polyurethane types, synthesis and applications: a review. RSC Adv 6:114453–114482.  https://doi.org/10.1039/c6ra14525f CrossRefGoogle Scholar
  3. Amran UA, Zakaria S, Chia CH, Jaafar SNS, Roslan R (2015) Mechanical properties and water absorption of glass fibre reinforced bio-phenolic elastomer (BPE) composite. Ind Crops Prod 72:54–59.  https://doi.org/10.1016/j.indcrop.2015.01.054 CrossRefGoogle Scholar
  4. Amran UA, Zakaria S, Chia CH, Fang Z, Masli MZ (2017) Production of liquefied oil palm empty fruit bunch based polyols via microwave heating. Energy Fuels 31:10975–10982.  https://doi.org/10.1021/acs.energyfuels.7b02098 CrossRefGoogle Scholar
  5. Aracri E, Díaz Blanco C, Tzanov T (2014) An enzymatic approach to develop a lignin-based adhesive for wool floor coverings. Green Chem 16:2597–2603.  https://doi.org/10.1039/C4GC00063C CrossRefGoogle Scholar
  6. ASTM (2008) D1622/D1622 M-14, Standard test method for apparent density of rigid cellular plastics. ASTM International, West Conshohocken, PA.  https://doi.org/10.1520/d1622_d1622m-14
  7. ASTM (2015a) D4662, Standard test methods for polyurethane raw materials: determination of acid and alkalinity numbers of polyols. ASTM International, West Conshohocken, PA.  https://doi.org/10.1520/d4662-15
  8. ASTM (2015b) D6226-15, Standard test method for open cell content of rigid cellular plastics. ASTM International, West Conshohocken, PA.  https://doi.org/10.1520/d6226-15
  9. ASTM (2016a) D1621-16, Standard test method for compressive properties of rigid cellular plastics. ASTM International, West Conshohocken, PA.  https://doi.org/10.1520/d1621-16
  10. ASTM (2016b) D4274-16, Standard test methods for testing polyurethane raw materials, determination of hydroxyl numbers of polyols. ASTM International, West Conshohocken, PA.  https://doi.org/10.1520/d4274-16
  11. Bhattacharjee D, Engineer R (1996) An improved technique for the determination of isocyanurate and isocyanate conversion by photoacoustic FTIR. J Cell Plast 32:260–273.  https://doi.org/10.1177/0021955x9603200304 CrossRefGoogle Scholar
  12. Blazsó M, Tóth T (1986) Thermal decomposition of methylene bridges and methyl groups at aromatic rings in phenol-formaldehyde polycondensates. J Anal Appl Pyrol 10:41–50.  https://doi.org/10.1016/0165-2370(86)85018-5 CrossRefGoogle Scholar
  13. Cao S et al (2017) A thermal self-healing polyurethane thermoset based on phenolic urethane. Polym J 49:775.  https://doi.org/10.1038/pj.2017.48 CrossRefGoogle Scholar
  14. Chattopadhyay DK, Webster DC (2009) Thermal stability and flame retardancy of polyurethanes. Prog Polym Sci 34:1068–1133.  https://doi.org/10.1016/j.progpolymsci.2009.06.002 CrossRefGoogle Scholar
  15. 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 CrossRefGoogle Scholar
  16. Chen Y, Das R, Battley M (2015) Effects of cell size and cell wall thickness variations on the stiffness of closed-cell foams. Int J Solids Struct 52:150–164.  https://doi.org/10.1016/j.ijsolstr.2014.09.022 CrossRefGoogle Scholar
  17. Chen W et al (2018) Fabrication and characterization of gefitinib-releasing polyurethane foam as a coating for drug-eluting stent in the treatment of bronchotracheal cancer. Int J Pharm 548:803–811.  https://doi.org/10.1016/j.ijpharm.2017.10.026 CrossRefGoogle Scholar
  18. 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 CrossRefGoogle Scholar
  19. Dislich C et al (2017) A review of the ecosystem functions in oil palm plantations, using forests as a reference system. Biol Rev 92:1539–1569.  https://doi.org/10.1111/brv.12295 CrossRefGoogle Scholar
  20. Effendi A, Gerhauser H, Bridgwater AV (2008) Production of renewable phenolic resins by thermochemical conversion of biomass: a review. Renew Sustain Energy Rev 12:2092–2116.  https://doi.org/10.1016/j.rser.2007.04.008 CrossRefGoogle Scholar
  21. Ek M, Gellerstedt G, Henriksson G (2009) Volume 1 wood chemistry and wood biotechnology. Walter de Gruyter, Berlin.  https://doi.org/10.1515/9783110213409 CrossRefGoogle Scholar
  22. Gan S, Zakaria S, Chia CH, Padzil FNM, Ng P (2015) Effect of hydrothermal pretreatment on solubility and formation of kenaf cellulose membrane and hydrogel. Carbohydr Polym 115:62–68.  https://doi.org/10.1016/j.carbpol.2014.08.093 CrossRefGoogle Scholar
  23. Gibson LJ, Ashby MF (1999) Cellular solids: structure and properties, 2nd edn. Cambridge University Press, CambridgeGoogle Scholar
  24. Heredia-Guerrero JA, Benítez JJ, Domínguez E, Bayer IS, Cingolani R, Athanassiou A, Heredia A (2014) Infrared and Raman spectroscopic features of plant cuticles: a review. Front Plant Sci 5:305.  https://doi.org/10.3389/fpls.2014.00305 CrossRefGoogle Scholar
  25. 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 CrossRefGoogle Scholar
  26. Huang X, De Hoop CF, Xie J, Wu Q, Boldor D, Qi J (2018) High bio-content polyurethane (PU) foam made from bio-polyol and cellulose nanocrystals (CNCs) via microwave liquefaction. Mater Des 138:11–20.  https://doi.org/10.1016/j.matdes.2017.10.058 CrossRefGoogle Scholar
  27. Hubbell CA, Ragauskas AJ (2010) Effect of acid-chlorite delignification on cellulose degree of polymerization. Biores Technol 101:7410–7415.  https://doi.org/10.1016/j.biortech.2010.04.029 CrossRefGoogle Scholar
  28. Islam SM, Hasan M, Ahmad MB (eds) (2014) Chemical modification and properties of cellulose-based polymer composites. In: Lignocellulosic polymer composites. Wiley, New York, pp 301–324.  https://doi.org/10.1002/9781118773949.ch14
  29. Jasiukaitytė E, Kunaver M, Strlič M (2009) Cellulose liquefaction in acidified ethylene glycol. Cellulose 16:393–405.  https://doi.org/10.1007/s10570-009-9288-y CrossRefGoogle Scholar
  30. Jiao L, Xiao H, Wang Q, Sun J (2013) Thermal degradation characteristics of rigid polyurethane foam and the volatile products analysis with TG-FTIR-MS. Polym Degrad Stab 98:2687–2696.  https://doi.org/10.1016/j.polymdegradstab.2013.09.032 CrossRefGoogle Scholar
  31. Jin Y, Ruan X, Cheng X, Lü Q (2011) Liquefaction of lignin by polyethyleneglycol and glycerol. Biores Technol 102:3581–3583.  https://doi.org/10.1016/j.biortech.2010.10.050 CrossRefGoogle Scholar
  32. 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 CrossRefGoogle Scholar
  33. Kosmela P, Hejna A, Formela K, Haponiuk JT, Piszczyk Ł (2016) Biopolyols obtained via crude glycerol-based liquefaction of cellulose: their structural, rheological and thermal characterization. Cellulose 23:2929–2942.  https://doi.org/10.1007/s10570-016-1034-7 CrossRefGoogle Scholar
  34. Li Y, Luo X, Hu S (2015) Bio-based polyols and polyurethanes. Springer, BerlinCrossRefGoogle Scholar
  35. Li J, Wang W, Zhang S, Gao Q, Zhang W, Li J (2016) Preparation and characterization of lignin demethylated at atmospheric pressure and its application in fast curing biobased phenolic resins. RSC Adv 6:67435–67443.  https://doi.org/10.1039/C6RA11966B CrossRefGoogle Scholar
  36. Li H, Xu C, Yuan Z, Wei Q (2018) Synthesis of bio-based polyurethane foams with liquefied wheat straw: process optimization. Biomass Bioenerg 111:134–140.  https://doi.org/10.1016/j.biombioe.2018.02.011 CrossRefGoogle Scholar
  37. Lv P, Almeida G, Perré P (2015) TGA-FTIR analysis of torrefaction of lignocellulosic components (cellulose, xylan, lignin) in isothermal conditions over a wide range of time durations. Bioresources 10:4239–4251Google Scholar
  38. Lyu H et al (2015) Two-stage nanofiltration process for high-value chemical production from hydrolysates of lignocellulosic biomass through hydrothermal liquefaction. Sep Purif Technol 147:276–283.  https://doi.org/10.1016/j.seppur.2015.04.032 CrossRefGoogle Scholar
  39. Mainka H, Hilfert L, Busse S, Edelmann F, Haak E, Herrmann AS (2015) Characterization of the major reactions during conversion of lignin to carbon fiber. J Mater Res Technol 4:377–391.  https://doi.org/10.1016/j.jmrt.2015.04.005 CrossRefGoogle Scholar
  40. Matsushita Y, Kakehi A, Miyawaki S, Yasuda S (2004) Formation and chemical structures of acid-soluble lignin II: reaction of aromatic nuclei model compounds with xylan in the presence of a counterpart for condensation, and behavior of lignin model compounds with guaiacyl and syringyl nuclei in 72% sulfuric acid. J Wood Sci 50:136–141.  https://doi.org/10.1007/s10086-003-0543-9 CrossRefGoogle Scholar
  41. MPOB (2017) Malaysian oil palm statistics. Department of Statistics Malaysia. http://bepi.mpob.gov.my/images/overview/Overview_of_Industry_2016.pdf. Accessed 25 Oct 2017
  42. Mu L, Shi Y, Wang H, Zhu J (2016) Lignin in ethylene glycol and poly(ethylene glycol): fortified lubricants with internal hydrogen bonding. ACS Sustain Chem Eng 4:1840–1849.  https://doi.org/10.1021/acssuschemeng.6b00049 CrossRefGoogle Scholar
  43. Niu M, Zhao G-j, Alma MH (2011) Polycondensation reaction and its mechanism during lignocellulosic liquefaction by an acid catalyst: a review. For Stud China 13:71–79.  https://doi.org/10.1007/s11632-011-0109-7 CrossRefGoogle Scholar
  44. Pan H, Shupe TF, Hse C-Y (2007) Characterization of liquefied wood residues from different liquefaction conditions. J Appl Polym Sci 105:3740–3746.  https://doi.org/10.1002/app.26435 CrossRefGoogle Scholar
  45. Paruzel A, Michałowski S, Hodan J, Horák P, Prociak A, Beneš H (2017) Rigid polyurethane foam fabrication using medium chain glycerides of coconut oil and plastics from end-of-life vehicles. ACS Sustain Chem Eng 5:6237–6246.  https://doi.org/10.1021/acssuschemeng.7b01197 CrossRefGoogle Scholar
  46. Popescu CM, Popescu MC, Vasile C (2010) Structural changes in biodegraded lime wood. Carbohydr Polym 79:362–372.  https://doi.org/10.1016/j.carbpol.2009.08.015 CrossRefGoogle Scholar
  47. Rajendran K (2017) Effect of moisture content on lignocellulosic power generation: energy. Econ Environ Impacts Proces 5:78Google Scholar
  48. Roslan R, Zakaria S, Chia CH, Boehm R, Laborie M-P (2014) Physico-mechanical properties of resol phenolic adhesives derived from liquefaction of oil palm empty fruit bunch fibres. Ind Crops Prod 62:119–124CrossRefGoogle Scholar
  49. Russell JA, Miller RK, Molton PM (1983) Formation of aromatic compounds from condensation reactions of cellulose degradation products. Biomass 3:43–57.  https://doi.org/10.1016/0144-4565(83)90007-0 CrossRefGoogle Scholar
  50. Timilsena YP, Audu IG, Rakshit SK, Brosse N (2013) Impact of the lignin structure of three lignocellulosic feedstocks on their organosolv delignification. Effect of carbonium ion scavengers. Biomass Bioenergy 52:151–158.  https://doi.org/10.1016/j.biombioe.2013.02.040 CrossRefGoogle Scholar
  51. Tsutsumi Y, Kondo R, Sakai K, Imamura H (1995) The difference of reactivity between syringyl lignin and guaiacyl lignin in alkaline systems. Holzforschung Int J Biol Chem Phys Technol Wood 49:423–428.  https://doi.org/10.1515/hfsg.1995.49.5.423 Google Scholar
  52. USDA (2017) Oilseeds: world markets and trade. Foreign Agricultural Service. USDA Office of Global Analysis. https://apps.fas.usda.gov/psdonline/circulars/oilseeds.pdf. Accessed 25 Oct 2017
  53. Wang K, Kim KH, Brown RC (2014) Catalytic pyrolysis of individual components of lignocellulosic biomass. Green Chem 16:727–735.  https://doi.org/10.1039/C3GC41288A CrossRefGoogle Scholar
  54. Wu H, Chen F, Liu M, Wang J (2017) Preparation of microcrystalline cellulose by liquefaction of eucalyptus sawdust in ethylene glycol catalyzed by acidic ionic liquid. Bioresources 12:3766–3777Google Scholar
  55. Yamada T, Hu Y, Ono H (2001) Condensation reaction of degraded lignocellulose during wood liquefaction in the presence of polyhydricalcohols. J Adhes Soc Jpn 37:471–478.  https://doi.org/10.11618/adhesion.37.471 CrossRefGoogle Scholar
  56. Yamada T, Aratani M, Kubo S, Ono H (2007) Chemical analysis of the product in acid-catalyzed solvolysis of cellulose using polyethylene glycol and ethylene carbonate. J Wood Sci 53:487–493.  https://doi.org/10.1007/s10086-007-0886-8 CrossRefGoogle Scholar
  57. Yang H, Yan R, Chen H, Lee DH, Zheng C (2007) Characteristics of hemicellulose, cellulose and lignin pyrolysis. Fuel 86:1781–1788.  https://doi.org/10.1016/j.fuel.2006.12.013 CrossRefGoogle Scholar
  58. Yue D, Oribayo O, Rempel G, Pan Q (2017) Liquefaction of waste pine wood and its application in the synthesis of a flame retardant polyurethane foam RSC. Advances 7:30334–30344.  https://doi.org/10.1039/C7RA03546B Google Scholar
  59. Zakaria S, Roslan R, Amran UA, Chia CH, Bakaruddin SB (2014) Characterization of residue from EFB and kenaf core fibres in the liquefaction process. Sains Malays 43:429–435Google Scholar
  60. Zhang T, Zhou Y, Liu D, Petrus L (2007) Qualitative analysis of products formed during the acid catalyzed liquefaction of bagasse in ethylene glycol. Biores Technol 98:1454–1459.  https://doi.org/10.1016/j.biortech.2006.03.029 CrossRefGoogle Scholar
  61. 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 CrossRefGoogle Scholar

Copyright information

© Springer Nature B.V. 2019

Authors and Affiliations

  1. 1.Bioresources and Biorefinery Laboratory, Materials Science Program, Faculty of Science and TechnologyUniversiti Kebangsaan MalaysiaBangiMalaysia
  2. 2.Faculty of Industrial Sciences and TechnologyUniversiti Malaysia PahangGambangMalaysia

Personalised recommendations