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Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride

Year 2021, , 306 - 310, 30.09.2021
https://doi.org/10.18182/tjf.948411

Abstract

In this study, cellulose was isolated from black poplar (Populus nigra L.) sawdust, which is produced by forest industrial processes in large amounts as lignocellulosic waste. Isolated cellulose was then esterified with different concentrations of octanoyl chloride (36–162 mmol, 2–9 equivalent per anhydroglucose unit in cellulose), and the obtained derivatives were characterized in terms of elemental analysis, percent yield, degree of substitution (DS), and solubility. DS values of cellulose derivatives ranged from 1.13 to 2.71, while percent yields varied between 56.36% and 93.23%. Solubility analysis revealed that esterification improved the hydrophobic capacity of cellulose. The findings of the study showed that the produced cellulose derivatives might be appropriate for the production of biodegradable and environmentally degradable plastics, resins, films, and coatings for use in some industrial areas such as in the food and pharmaceutical industries.

References

  • Antova, G., Vasvasova, P., Zlatanov, M., 2004. Studies upon the synthesis of cellulose stearate under microwave heating. Carbohydr. Polym., 57: 131–134.
  • Arikan, E.B., Bilgen, H.D., 2019. Production of bioplastic from potato peel waste and investigation of its biodegradability. International Advanced Researches and Engineering Journal, 3(2): 93-97.
  • Civitarese, V., Acampora, A., Sperandio, G., Assirelli, A., Picchio, R., 2019. Production of wood pellets from poplar trees managed as coppices with Different harvesting cycles. Energies, 12(15): 2973.
  • Crepy, L., Chaveriat, L., Banoub, J., Martin, P., Joly, N., 2009. Synthesis of cellulose fatty esters as plastics-influence of the degree of substitution and the fatty chain length on mechanical properties. ChemSusChem, 2(2): 165–170.
  • Fengel, D., Wegener, G., 1984. Wood-Chemistry, Ultrastructure, Reaction, Walter de Gruyter, Berlin.
  • Gaudet, M., Jorge, V., Paolucci, I., Beritognolo, I., Scarascia Mugnozza, G., Sabatti, M., 2008. Genetic linkage maps of Populus nigra L. including AFLPs, SSRs, SNPs, and sex trait. Tree Genetics and Genomes, 4:25–36. Heredia-Guerrero, J.A., Goldoni, L., Benítez, J.J., Davis, A., Ceseracciu, L., Cingolani, R., Bayer, I.S., Heinze, T., Koschella, A., Heredia, A., Athanassiou, A., 2017. Cellulose-polyhydroxylated fatty acid ester-based bioplastics with tuning properties: Acylation via a mixed anhydride system. Carbohydrate Polymers, 173: 312–320.
  • Joly, N., Granet, R., Krausz, P., 2003. Crosslinking of cellulose by olefin metathesis. Journal of Carbohydrate Chemistry, 22: 47–55.
  • Joly, N., Granet, R., Branland, P., Verneuil, B., Krausz, P., 2005. New methods for acylation of pure and sawdust-extracted cellulose by fatty acid derivatives—Thermal and mechanical analyses of cellulose-based plastic films. Journal of Applied Polymer Science, 97(3): 1266–1278.
  • Joly, N., Martin, P., Lienard, L., Rutot, D., Stassin, F., Granet, R., Krausz, J.P., Cavrot, J-P., 2006. Effect of degree of substitution on the mechanical and thermomechanical properties of lauroyl cellulose ester films. e-Polymers, 70: 1–9.
  • Kahraman, T., Kahraman, F. K., Karakaya, S., Karahan, A., Ünsal, G., Karatay, H., Toplu, F., 2011. Türkiye’de Karakavakta (Populus nigra L.) ıslah çalışmaları ‘Fidanlık aşaması sonuçları’. T.C. Orman ve Su İşleri Bakanlığı Kavak ve Hızlı Gelişen Orman Ağaçları Araştırma Enstitüsü Müdürlüğü, Teknik Bülten No: 210, İzmit, Türkiye.
  • Krassig H.A., 1993. Cellulose: Structure Accessibility and Reactivity. Polymer Monographs, Vol. 11, Gordon and Breach Science Publishers, Amsterdam.
  • Kurschner, K., Hoffer, A., 1969. Ein neues verfahren zur bestimmung der zellulose in hölzern und zellstoffen. Technologie und Chemie der Papier- u. Zellstoff-Fabrikation, 26: 125-139.
  • Lange, J.P., 2007. Lignocellulose conversion: an introduction to chemistry, process and economics. Biofuels, Bioproducts and Biorefining, 1(1): 39–48.
  • Lepeniotis, S., Feuer, B.I., 1997. Synthesis of starch acetate: Statistical designed experiments to optimize the reaction conditions. Chemometrics and Intelligent Laboratory Systems, 36(2): 229-243.
  • Mark, H.F., Bikales, N.M., Overberger, C.G., Menges, G., 1985. Encyclopedia of Polymer Science and Engineering, Vol. 3: Cellular Materials to Composites. 2nd ed., Wiley-VCH, pp. 158–226.
  • McCormick, C.L., Callais, P.A., Hutchinson Jr, B.H., 1985. Solution studies of cellulose in lithium chloride and N, N-dimethylacetamide. Macromolecules, 18(12): 2394-2401.
  • Mediavilla, I., Esteban, L.S., Fernández, M.J., 2012. Optimisation of pelletisation conditions for poplar energy crop. Fuel Processing Technology, 104: 7-15.
  • Monedero, E., Portero, H., Lapuerta, M., 2015. Pellet blends of poplar and pine sawdust: Effects of material composition, additive, moisture content and compression die on pellet quality. Fuel Processing Technology, 132: 15-23.
  • Moshood, T.D., Nawanir, G., Mahmud, F., Mohamad, F., Ahmad, M.H., Abdul Ghani, A., 2021. Expanding policy for biodegradable plastic products and market dynamics of bio-based plastics: challenges and opportunities. Sustainability, 13(11): 6170.
  • Nosal, H., Moser, K., Warzała, M., Holzer, A., Stanczyk, D., Sabura, E., 2021. Selected Fatty Acids Esters as Potential PHB-V Bioplasticizers: Effect on Mechanical Properties of the Polymer. Journal of Polymers and the Environment, 29(1): 38-53.
  • Rahn, K., Diamantoglou, M., Klemm, D., Berghmans, H., Heinze, T., 1996. Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamide/LiCl solvent system. Die Angewandte Makromolekulare Chemie: Applied Macromolecular Chemistry and Physics, 238(1): 143-163.
  • Rathmacher, G., Niggemann, M., Kohnen, M., Ziegenhagen, B., Bialozyt, R., 2010. Short distance gene flow in Populus nigra L. accounts for small scale spatial genetic structures: Implications for in situ conservation measures. Conserv. Genet., 11: 1327–1338.
  • Samarasinghe, S., Easteal, A.J., Edmonds, N.R., 2007. Biodegradable plastic composites from corn gluten meal. Polymer International, 57(2): 359–364.
  • Samaranayake, G., Glasser, W.G., 1993. Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr. Polym., 22(1): 1–7.
  • Satge, C., Verneuil, B., Branland, P., Granet, R., Krausz, P., Rozier, J., Petit, C., 2002. Rapid homogeneous esterification of cellulose induced by microwave irradiation. Carbohydrate Polymers, 49: 373–376. Satge, C., Verneuil, B., Branland, P., Krausz, P., 2004. Synthesis and properties of biodegradable plastic films obtained by microwave-assisted cellulose acylation in homogeneous phase. Comptes Rendus Chimie, 7: 135–142.
  • Sealey, J.E., Samaranayake, G., Todd, J.G., Glasser, W.G., 1996. Novel cellulose derivatives. IV. Preparation and thermal analysis of waxy esters of cellulose. Journal of Polymer Science Part B: Polymer Physics, 34(9): 1613–1620.
  • Sjöström, E., 1993. Wood Chemistry, Fundamentals and Applications, Second Edition, Acedemic Press, Inc., San Diego.
  • Sun, R.C., Fang, J.M., Tomkinson, J., Hill, C.A.S., 1999. Esterification of hemicelluloses from poplar chips in homogenous solution of N,N-dimethylformamide/Lithium chloride. Journal of Wood Chemistry and Technology, 19(4): 287-306.
  • Sun, R.C., Fang, J.M., Tomkinson, J., 2000. Characterization and esterification of hemicelluloses from rye straw. Journal Agricultural Food Chemistry, 48(4): 1247-1252.
  • Vaca-Garcia, C., Thiebaud, S., Borredon, M.E., Gozzelino, G., 1998. Cellulose esterification with fatty acids and acetic anhydride in lithium chloride/N,Ndimethylacetamide medium. Journal of the American Oil Chemists’ Society, 75: 315–319.
  • Wang, X., Chen, Z., Yu, G., Yuan, X., 2018. Effects of poplar fibres as solid bridge on the physical characteristics of biomass briquette made from sawdust and bamboo powder. Wood Research, 63(1): 141-153.
  • Willberg-Keyrilainen, P., Ropponen, J., 2019. Evaluation of esterification routes for long chain cellulose esters. Heliyon, 5(11): e02898.

Karakavak (Populus nigra L.) talaşından izole edilen selülozun oktanoil klorür ile esterlenmesi

Year 2021, , 306 - 310, 30.09.2021
https://doi.org/10.18182/tjf.948411

Abstract

Bu çalışmada, orman endüstrisi proseslerinde büyük miktarlarda lignoselülozik atık olarak ortaya çıkan karakavak (Populus nigra L.) talaşından selüloz izole edilmiştir. İzole edilen selüloz daha sonra farklı konsantrasyonlardaki oktanoil klorür (36-162 mmol, selülozdaki anhidroglukoz birimi başına 2-9 ekivalent) ile esterlenmiş ve elde edilen türevler elementel analiz, yüzde verim, sübstitüsyon derecesi (DS) ve çözünürlük ile karakterize edilmiştir. Selüloz türevlerinin DS değerleri 1.13 ile 2.71 arasında değişirken, verim yüzdelerinin %56.36 ile %93.23 arasında olduğu görülmüştür. Çözünürlük analizi sonucu, esterleme ile selülozun hidrofobik kapasitesinde gelişme olduğu görülmüştür. Çalışma sonuçları, elde edilen selüloz türevlerinin, gıda ve ilaç endüstrileri gibi bazı alanlarda kullanılabilecek biyolojik olarak parçalanabilir ve çevreye karışabilir plastik, reçine, film ve kaplamaların üretimi için uygun olabileceğini göstermiştir.

References

  • Antova, G., Vasvasova, P., Zlatanov, M., 2004. Studies upon the synthesis of cellulose stearate under microwave heating. Carbohydr. Polym., 57: 131–134.
  • Arikan, E.B., Bilgen, H.D., 2019. Production of bioplastic from potato peel waste and investigation of its biodegradability. International Advanced Researches and Engineering Journal, 3(2): 93-97.
  • Civitarese, V., Acampora, A., Sperandio, G., Assirelli, A., Picchio, R., 2019. Production of wood pellets from poplar trees managed as coppices with Different harvesting cycles. Energies, 12(15): 2973.
  • Crepy, L., Chaveriat, L., Banoub, J., Martin, P., Joly, N., 2009. Synthesis of cellulose fatty esters as plastics-influence of the degree of substitution and the fatty chain length on mechanical properties. ChemSusChem, 2(2): 165–170.
  • Fengel, D., Wegener, G., 1984. Wood-Chemistry, Ultrastructure, Reaction, Walter de Gruyter, Berlin.
  • Gaudet, M., Jorge, V., Paolucci, I., Beritognolo, I., Scarascia Mugnozza, G., Sabatti, M., 2008. Genetic linkage maps of Populus nigra L. including AFLPs, SSRs, SNPs, and sex trait. Tree Genetics and Genomes, 4:25–36. Heredia-Guerrero, J.A., Goldoni, L., Benítez, J.J., Davis, A., Ceseracciu, L., Cingolani, R., Bayer, I.S., Heinze, T., Koschella, A., Heredia, A., Athanassiou, A., 2017. Cellulose-polyhydroxylated fatty acid ester-based bioplastics with tuning properties: Acylation via a mixed anhydride system. Carbohydrate Polymers, 173: 312–320.
  • Joly, N., Granet, R., Krausz, P., 2003. Crosslinking of cellulose by olefin metathesis. Journal of Carbohydrate Chemistry, 22: 47–55.
  • Joly, N., Granet, R., Branland, P., Verneuil, B., Krausz, P., 2005. New methods for acylation of pure and sawdust-extracted cellulose by fatty acid derivatives—Thermal and mechanical analyses of cellulose-based plastic films. Journal of Applied Polymer Science, 97(3): 1266–1278.
  • Joly, N., Martin, P., Lienard, L., Rutot, D., Stassin, F., Granet, R., Krausz, J.P., Cavrot, J-P., 2006. Effect of degree of substitution on the mechanical and thermomechanical properties of lauroyl cellulose ester films. e-Polymers, 70: 1–9.
  • Kahraman, T., Kahraman, F. K., Karakaya, S., Karahan, A., Ünsal, G., Karatay, H., Toplu, F., 2011. Türkiye’de Karakavakta (Populus nigra L.) ıslah çalışmaları ‘Fidanlık aşaması sonuçları’. T.C. Orman ve Su İşleri Bakanlığı Kavak ve Hızlı Gelişen Orman Ağaçları Araştırma Enstitüsü Müdürlüğü, Teknik Bülten No: 210, İzmit, Türkiye.
  • Krassig H.A., 1993. Cellulose: Structure Accessibility and Reactivity. Polymer Monographs, Vol. 11, Gordon and Breach Science Publishers, Amsterdam.
  • Kurschner, K., Hoffer, A., 1969. Ein neues verfahren zur bestimmung der zellulose in hölzern und zellstoffen. Technologie und Chemie der Papier- u. Zellstoff-Fabrikation, 26: 125-139.
  • Lange, J.P., 2007. Lignocellulose conversion: an introduction to chemistry, process and economics. Biofuels, Bioproducts and Biorefining, 1(1): 39–48.
  • Lepeniotis, S., Feuer, B.I., 1997. Synthesis of starch acetate: Statistical designed experiments to optimize the reaction conditions. Chemometrics and Intelligent Laboratory Systems, 36(2): 229-243.
  • Mark, H.F., Bikales, N.M., Overberger, C.G., Menges, G., 1985. Encyclopedia of Polymer Science and Engineering, Vol. 3: Cellular Materials to Composites. 2nd ed., Wiley-VCH, pp. 158–226.
  • McCormick, C.L., Callais, P.A., Hutchinson Jr, B.H., 1985. Solution studies of cellulose in lithium chloride and N, N-dimethylacetamide. Macromolecules, 18(12): 2394-2401.
  • Mediavilla, I., Esteban, L.S., Fernández, M.J., 2012. Optimisation of pelletisation conditions for poplar energy crop. Fuel Processing Technology, 104: 7-15.
  • Monedero, E., Portero, H., Lapuerta, M., 2015. Pellet blends of poplar and pine sawdust: Effects of material composition, additive, moisture content and compression die on pellet quality. Fuel Processing Technology, 132: 15-23.
  • Moshood, T.D., Nawanir, G., Mahmud, F., Mohamad, F., Ahmad, M.H., Abdul Ghani, A., 2021. Expanding policy for biodegradable plastic products and market dynamics of bio-based plastics: challenges and opportunities. Sustainability, 13(11): 6170.
  • Nosal, H., Moser, K., Warzała, M., Holzer, A., Stanczyk, D., Sabura, E., 2021. Selected Fatty Acids Esters as Potential PHB-V Bioplasticizers: Effect on Mechanical Properties of the Polymer. Journal of Polymers and the Environment, 29(1): 38-53.
  • Rahn, K., Diamantoglou, M., Klemm, D., Berghmans, H., Heinze, T., 1996. Homogeneous synthesis of cellulose p-toluenesulfonates in N,N-dimethylacetamide/LiCl solvent system. Die Angewandte Makromolekulare Chemie: Applied Macromolecular Chemistry and Physics, 238(1): 143-163.
  • Rathmacher, G., Niggemann, M., Kohnen, M., Ziegenhagen, B., Bialozyt, R., 2010. Short distance gene flow in Populus nigra L. accounts for small scale spatial genetic structures: Implications for in situ conservation measures. Conserv. Genet., 11: 1327–1338.
  • Samarasinghe, S., Easteal, A.J., Edmonds, N.R., 2007. Biodegradable plastic composites from corn gluten meal. Polymer International, 57(2): 359–364.
  • Samaranayake, G., Glasser, W.G., 1993. Cellulose derivatives with low DS. I. A novel acylation system. Carbohydr. Polym., 22(1): 1–7.
  • Satge, C., Verneuil, B., Branland, P., Granet, R., Krausz, P., Rozier, J., Petit, C., 2002. Rapid homogeneous esterification of cellulose induced by microwave irradiation. Carbohydrate Polymers, 49: 373–376. Satge, C., Verneuil, B., Branland, P., Krausz, P., 2004. Synthesis and properties of biodegradable plastic films obtained by microwave-assisted cellulose acylation in homogeneous phase. Comptes Rendus Chimie, 7: 135–142.
  • Sealey, J.E., Samaranayake, G., Todd, J.G., Glasser, W.G., 1996. Novel cellulose derivatives. IV. Preparation and thermal analysis of waxy esters of cellulose. Journal of Polymer Science Part B: Polymer Physics, 34(9): 1613–1620.
  • Sjöström, E., 1993. Wood Chemistry, Fundamentals and Applications, Second Edition, Acedemic Press, Inc., San Diego.
  • Sun, R.C., Fang, J.M., Tomkinson, J., Hill, C.A.S., 1999. Esterification of hemicelluloses from poplar chips in homogenous solution of N,N-dimethylformamide/Lithium chloride. Journal of Wood Chemistry and Technology, 19(4): 287-306.
  • Sun, R.C., Fang, J.M., Tomkinson, J., 2000. Characterization and esterification of hemicelluloses from rye straw. Journal Agricultural Food Chemistry, 48(4): 1247-1252.
  • Vaca-Garcia, C., Thiebaud, S., Borredon, M.E., Gozzelino, G., 1998. Cellulose esterification with fatty acids and acetic anhydride in lithium chloride/N,Ndimethylacetamide medium. Journal of the American Oil Chemists’ Society, 75: 315–319.
  • Wang, X., Chen, Z., Yu, G., Yuan, X., 2018. Effects of poplar fibres as solid bridge on the physical characteristics of biomass briquette made from sawdust and bamboo powder. Wood Research, 63(1): 141-153.
  • Willberg-Keyrilainen, P., Ropponen, J., 2019. Evaluation of esterification routes for long chain cellulose esters. Heliyon, 5(11): e02898.
There are 32 citations in total.

Details

Primary Language English
Subjects Engineering
Journal Section Orijinal Araştırma Makalesi
Authors

Samim Yaşar 0000-0002-4742-3348

Publication Date September 30, 2021
Acceptance Date August 5, 2021
Published in Issue Year 2021

Cite

APA Yaşar, S. (2021). Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride. Turkish Journal of Forestry, 22(3), 306-310. https://doi.org/10.18182/tjf.948411
AMA Yaşar S. Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride. Turkish Journal of Forestry. September 2021;22(3):306-310. doi:10.18182/tjf.948411
Chicago Yaşar, Samim. “Esterification of Cellulose Isolated from Black Poplar (Populus Nigra L.) Sawdust With Octanoyl Chloride”. Turkish Journal of Forestry 22, no. 3 (September 2021): 306-10. https://doi.org/10.18182/tjf.948411.
EndNote Yaşar S (September 1, 2021) Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride. Turkish Journal of Forestry 22 3 306–310.
IEEE S. Yaşar, “Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride”, Turkish Journal of Forestry, vol. 22, no. 3, pp. 306–310, 2021, doi: 10.18182/tjf.948411.
ISNAD Yaşar, Samim. “Esterification of Cellulose Isolated from Black Poplar (Populus Nigra L.) Sawdust With Octanoyl Chloride”. Turkish Journal of Forestry 22/3 (September 2021), 306-310. https://doi.org/10.18182/tjf.948411.
JAMA Yaşar S. Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride. Turkish Journal of Forestry. 2021;22:306–310.
MLA Yaşar, Samim. “Esterification of Cellulose Isolated from Black Poplar (Populus Nigra L.) Sawdust With Octanoyl Chloride”. Turkish Journal of Forestry, vol. 22, no. 3, 2021, pp. 306-10, doi:10.18182/tjf.948411.
Vancouver Yaşar S. Esterification of cellulose isolated from black poplar (Populus nigra L.) sawdust with octanoyl chloride. Turkish Journal of Forestry. 2021;22(3):306-10.