Abstract
This research is dedicated to the study on the formation of levoglucosenone and other main volatiles from the catalytic pyrolysis with the addition of phosphoric acid of birch wood and lignocelluloses obtained by birch wood hydrothermal treatment. Py-GC/MS/FID method was used to evaluate the contents of the main products. Lignocelluloses were found to be a more promising precursor to obtain levoglucosenone with lesser content of furfural: For birch wood and lignocelluloses hydrothermally treated at 150 and 180 °C, Py-GC/MS/FID revealed levoglucosenone yields of 12.83, 16.94 and 21.08%, correspondingly (at 5% phosphoric acid addition). When birch wood impregnated with 5% H3PO4 was pyrolized in the laboratory screw-type reactor, the levoglucosenone yield was 6.5%. The composition and content of volatiles formed in analytical pyrolysis, bio-oil and its chloroform extract were compared. Extraction of bio-oil with chloroform and consequent distillation resulted in fractions containing 79.14% of levoglucosenone.
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References
Cao F, Schwartz TJ, McClelland DJ et al (2015) Dehydration of cellulose to levoglucosenone using polar aprotic solvents. Energy Environ Sci 8:1808–1815. https://doi.org/10.1039/C5EE00353A
Carslon TR, Ritter JC, Stauffer CS (2016) Process for producing levoglucosenone. WO 2016/100028 A1
Court GR, Lawrence CH, Raverty WD, et al (2011) Method for converting lignocellulosic materials into useful chemicals. WO 2011/000030 A1
Dobele G, Dizhbite T, Rossinskaya G, Telysheva G (1995) Thermocatalytic destruction of cellulose. Cellul Cellul Deriv. https://doi.org/10.1533/9781845698539.2.125
Dobele G, Meier D, Faix O et al (2001) Volatile products of catalytic flash pyrolysis of celluloses. J Anal Appl Pyrolysis 58–59:453–463. https://doi.org/10.1016/S0165-2370(00)00128-5
Dobele G, Dizhbite T, Rossinskaja G et al (2003) Pre-treatment of biomass with phosphoric acid prior to fast pyrolysis: a promising method for obtaining 1,6-anhydrosaccharides in high yields. J Anal Appl Pyrolysis 68–69:197–211. https://doi.org/10.1016/S0165-2370(03)00063-9
Dobele G, Rossinskaja G, Dizhbite T et al (2005) Application of catalysts for obtaining 1,6-anhydrosaccharides from cellulose and wood by fast pyrolysis. J Anal Appl Pyrolysis 74:401–405
Ermolenko MS (2013) Convenient and efficient synthesis of 2,4-dideoxy-levoglucosan. Synth Commun 43:2841–2845. https://doi.org/10.1080/00397911.2012.745158
Fabbri D, Torri C, Baravelli V (2007) Effect of zeolites and nanopowder metal oxides on the distribution of chiral anhydrosugars evolved from pyrolysis of cellulose: an analytical study. J Anal Appl Pyrolysis 80:24–29. https://doi.org/10.1016/j.jaap.2006.12.025
He X, Li R, Qiu J et al (2012) Synthesis of mesoporous carbons for supercapacitors from coal tar pitch by coupling microwave-assisted KOH activation with a MgO template. Carbon N Y 50:4911–4921. https://doi.org/10.1016/j.carbon.2012.06.020
Hu F, Ragauskas A (2012) Pretreatment and lignocellulosic chemistry. BioEnergy Res 5:1043–1066. https://doi.org/10.1007/s12155-012-9208-0
Johnson RL, Liaw S-S, Garcia-Perez M et al (2009) Pyrolysis gas chromatography mass spectrometry studies to evaluate high-temperature aqueous pretreatment as a way to modify the composition of bio-oil from fast pyrolysis of wheat straw. Energy Fuels 23:6242–6252. https://doi.org/10.1021/ef900742x
Leal GF, Ramos LA, Barrett DH et al (2015) A thermogravimetric analysis (TGA) method to determine the catalytic conversion of cellulose from carbon-supported hydrogenolysis process. Thermochim Acta 616:9–13. https://doi.org/10.1016/J.TCA.2015.07.017
Lu Q, Ye XN, Zhang ZB et al (2014a) Catalytic fast pyrolysis of cellulose and biomass to produce levoglucosenone using magnetic SO42-/TiO2-Fe3O4. Bioresour Technol 171:10–15. https://doi.org/10.1016/j.biortech.2014.08.075WO2016/100028A1
Lu Q, Zhang Y, Dong C et al (2014b) The mechanism for the formation of levoglucosenone during pyrolysis of β-d-glucopyranose and cellobiose: a density functional theory study. J Anal Appl Pyrolysis 110:34–43. https://doi.org/10.1016/J.JAAP.2014.08.002
Meng X, Zhang H, Liu C, Xiao R (2016) Comparison of acids and sulfates for producing levoglucosan and levoglucosenone by selective catalytic fast pyrolysis of cellulose using Py-GC/MS. Energy Fuels 30:8369–8376. https://doi.org/10.1021/acs.energyfuels.6b01436
Norske Skog (2016) FC5 Bio-chemical Prototype Plant Environmental Effects Report (extraction of sawdust with sulfolane and phosphoric acid). https://epa.tas.gov.au/Documents/Norske%20Skog%20Paper%20Mills%20(Australia)%20Ltd%20-%20Environmental%20Effects%20Report.pdf. Accessed 27 Dec 2019
Ostermeier M, Schobert R (2014) Total synthesis of (+)-chloriolide. J Org Chem. https://doi.org/10.1021/jo500527g
Paris C, Moliner M, Corma A (2013) Metal-containing zeolites as efficient catalysts for the transformation of highly valuable chiral biomass-derived products. Green Chem 15:2101. https://doi.org/10.1039/c3gc40267c
Relvas FM, Morais ARC, Bogel-Lukasik R (2015) Selective hydrolysis of wheat straw hemicellulose using high-pressure CO2 as catalyst. RSC Adv 5:73935–73944. https://doi.org/10.1039/C5RA14632A
Richardson DE, Raverty WD (2016) Predicted environmental effects from liquid emissions in the manufacture of levoglucosenone and Cyrene ™. Appita J 69:344–351
Shafizadeh F, Lai YZ, McIntyre CR (1978) Thermal degradation of 6-chlorocellulose and cellulose–zinc chloride mixture. J Appl Polym Sci 22:1183–1193. https://doi.org/10.1002/app.1978.070220503
Shafizadeh F, Furneaux RH, Cochran TG et al (1979a) Production of levoglucosan and glucose from pyrolysis of cellulosic materials. J Appl Polym Sci 23:3525–3539. https://doi.org/10.1002/app.1979.070231209
Shafizadeh F, Furneaux RH, Stevenson TT (1979b) Some reactions of levoglucosenone. Carbohydr Res 71:169–191. https://doi.org/10.1016/S0008-6215(00)86069-3
Shibagaki M, Takahashi K, Kuno H, et al (1991) Method of preparing levoglucosenone. EP0416577A2
Sui X, Wang Z, Liao B et al (2012) Bioresource technology preparation of levoglucosenone through sulfuric acid promoted pyrolysis of bagasse at low temperature. Bioresour Technol 103:466–469. https://doi.org/10.1016/j.biortech.2011.10.010
Urabe D, Nishikawa T, Isobe M (2006) An efficient total synthesis of optically active tetrodotoxin from levoglucosenone. Chem Asian J 1:125–135. https://doi.org/10.1002/asia.200600038
Wang S, Wang Y, Leng F, Chen J (2016) Stepwise enrichment of sugars from the heavy fraction of bio-oil. Energy Fuels 30:2233–2239. https://doi.org/10.1021/acs.energyfuels.6b00039
Wei X, Wang Z, Wu Y et al (2014) Fast pyrolysis of cellulose with solid acid catalysts for levoglucosenone. J Anal Appl Pyrolysis 107:150–154. https://doi.org/10.1016/j.jaap.2014.02.015
Xiao L-P, Song G-Y, Sun R-C (2017) Effect of hydrothermal processing on hemicellulose structure. Hydrothermal processing in biorefineries. Springer, Cham, pp 45–94
Zandersons J, Zhurinsh A, Dobele G et al (2013) Feasibility of broadening the feedstock choice for levoglucosenone production by acid pre-treatment of wood and catalytic pyrolysis of the obtained lignocellulose. J Anal Appl Pyrolysis 103:222–226. https://doi.org/10.1016/j.jaap.2013.01.014
Zhang H, Meng X, Liu C et al (2017) Selective low-temperature pyrolysis of microcrystalline cellulose to produce levoglucosan and levoglucosenone in a fixed bed reactor. Fuel Process Technol 167:484–490. https://doi.org/10.1016/j.fuproc.2017.08.007
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This research was supported by ERAF project Nr.1.1.1.1/16/A/010.
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Dobele, G., Zhurinsh, A., Volperts, A. et al. Study of levoglucosenone obtained in analytical pyrolysis and screw-type reactor, separation and distillation. Wood Sci Technol 54, 383–400 (2020). https://doi.org/10.1007/s00226-020-01164-7
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DOI: https://doi.org/10.1007/s00226-020-01164-7