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Cellulose

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07.04.2017 | Original Paper

Mechanism and kinetics studies of carboxyl group formation on the surface of cellulose fiber in a TEMPO-mediated system

verfasst von: Xiankui Sang, Chengrong Qin, Zhangfa Tong, Song Kong, Zhuan Jia, Guangcong Wan, Xinliang Liu

Erschienen in: Cellulose | Ausgabe 6/2017

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Abstract

2,2,6,6-Tetramethylpiperidine-1-oxyl radical (TEMPO) can selectively oxidize primary hydroxyl groups of cellulose to carboxyl groups. However, the depolymerization also occurs during the process. The kinetics and mechanism of carboxyl group formation on the surface of cellulose fiber oxidized by TEMPO/NaClO₂/NaClO were discussed. The oxidization and depolymerization of cellulose occurred simultaneously, according to analysis of FTIR and ¹³C CP/MAS NMR. The glucuronic acid and some small molecular fragments, formed by hydrolysis or β-elimination during the oxidation, are also discussed. The crystallization index increased and crystal size decreased, as shown by X-ray analysis. The degradation steps in the TEMPO/NaClO₂/NaClO system was discussed, according to carbon conversion analyzed by ¹³C CP/MAS NMR. The oxidation of cellulose can be described well by the kinetics model established based on the degradation of cellulose. It was found that temperature is one of the key parameters for controlling the oxdation and degradation level. The possible mechanism for oxidation of cellulose was composed.

Vorheriger Artikel Catalytic conversion of cellulose into polyols using carbon-nanotube-supported monometallic Pd and bimetallic Pd–Fe catalysts

Nächster Artikel Chemisorption of air CO2 on cellulose: an overlooked feature of the cellulose/NaOH(aq) dissolution system

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Åkerholm M, Hinterstoisser B, Salmén L (2004) Characterization of the crystalline structure of cellulose using static and dynamic FT-IR spectroscopy. Carbohydr Res 339:569–578. doi:10.1016/j.carres.2003.11.012 CrossRef

Araki J, Wada M, Kuga S, Okano T (1998) Flow properties of microcrystalline cellulose suspension prepared by acid treatment of native cellulose. Colloids Surf A 142:75–82CrossRef

Calvini P, Gorassini A, Luciano G, Franceschi E (2006) FTIR and WAXS analysis of periodate oxycellulose: evidence for a cluster mechanism of oxidation. Vib Spectrosc 40:177–183. doi:10.1016/j.vibspec.2005.08.004 CrossRef

Coseri S (2017) Cellulose: to depolymerize… or not to? Biotechnol Adv 35:251–266. doi:10.1016/j.biotechadv.2017.01.002 CrossRef

Coseri S, Biliuta G, Simionescu BC, Stana-Kleinschek K, Ribitsch V, Harabagiu V (2013) Oxidized cellulose—survey of the most recent achievements. Carbohydr Polym 93:207–215. doi:10.1016/j.carbpol.2012.03.086 CrossRef

da Silva Perez D, Montanari S, Vignon MR (2003) TEMPO-mediated oxidation of cellulose III. Biomacromolecules 4:1417–1425CrossRef

Dai L, Dai H, Yuan Y, Sun X, Zhu Z (2011) Effect of TEMPO oxidation system on kinetic constants of cotton fibers. BioResources 6:2619–2631

Dang Z, Zhang J, Ragauskas AJ (2007) Characterizing TEMPO-mediated oxidation of ECF bleached softwood kraft pulps. Carbohydr Polym 70:310–317. doi:10.1016/j.carbpol.2007.04.014 CrossRef

de Nooy AE, Besemer AC, van Bekkum H (1995) Selective oxidation of primary alcohols mediated by nitroxyl radical in aqueous solution. Kinetics and mechanism. Tetrahedron 51:8023–8032CrossRef

deNooy AEJ, Besemer AC, vanBekkum H, vanDijk J, Smit JAM (1996) TEMPO-mediated oxidation of pullulan and influence of ionic strength and linear charge density on the dimensions of the obtained polyelectrolyte chains. Macromolecules 29:6541–6547. doi:10.1021/ma960492t CrossRef

Elboutachfaiti R, Delattre C, Petit E, Michaud P (2011) Polyglucuronic acids: structures, functions and degrading enzymes. Carbohydr Polym 84:1–13. doi:10.1016/j.carbpol.2010.10.063 CrossRef

El-Sakhawy M, Hassan ML (2007) Physical and mechanical properties of microcrystalline cellulose prepared from agricultural residues. Carbohydr Polym 67:1–10CrossRef

Foston M (2014) Advances in solid-state NMR of cellulose. Curr Opin Biotechnol 27:176–184. doi:10.1016/j.copbio.2014.02.002 CrossRef

Fujisawa S, Isogai T, Isogai A (2010) Temperature and pH stability of cellouronic acid. Cellulose 17:607–615. doi:10.1007/s10570-010-9407-9 CrossRef

Fujisawa S, Okita Y, Fukuzumi H, Saito T, Isogai A (2011) Preparation and characterization of TEMPO-oxidized cellulose nanofibril films with free carboxyl groups. Carbohydr Polym 84:579–583. doi:10.1016/j.carbpol.2010.12.029 CrossRef

Henriksson M, Henriksson G, Berglund LA, Lindstrom T (2007) An environmentally friendly method for enzyme-assisted preparation of microfibrillated cellulose (MFC) nanofibers. Eur Polym J 43:3434–3441. doi:10.1016/j.eurpolymj.2007.05.038 CrossRef

Hiraoki R, Ono Y, Saito T, Isogai A (2015) Molecular mass and molecular-mass distribution of TEMPO-oxidized celluloses and TEMPO-oxidized cellulose nanofibrils. Biomacromolecules 16:675–681. doi:10.1021/bm501857c CrossRef

Hirota M, Tamura N, Saito T, Isogai A (2009) Oxidation of regenerated cellulose with NaClO₂ catalyzed by TEMPO and NaClO under acid-neutral conditions. Carbohydr Polym 78:330–335. doi:10.1016/j.carbpol.2009.04.012 CrossRef

Hult E-L, Larsson PT, Iversen T (2000) A comparative CP/MAS 13C-NMR study of cellulose structure in spruce wood and kraft pulp. Cellulose 7:35–55. doi:10.1023/a:1009236932134 CrossRef

Isogai A, Kato Y (1998) Preparation of polyuronic acid from cellulose by TEMPO-mediated oxidation. Cellulose 5:153–164. doi:10.1023/A:1009208603673 CrossRef

Isogai T, Yanagisawa M, Isogai A (2009) Degrees of polymerization (DP) and DP distribution of cellouronic acids prepared from alkali-treated celluloses and ball-milled native celluloses by TEMPO-mediated oxidation. Cellulose 16:117–127. doi:10.1007/s10570-008-9245-1 CrossRef

Isogai A, Saito T, Fukuzumi H (2011) TEMPO-oxidized cellulose nanofibers. Nanoscale 3:71–85. doi:10.1039/c0nr00583e CrossRef

Johansson EE, Lind J (2005) Free radical mediated cellulose degradation during high consistency ozonation. J Wood Chem Technol 25:171–186. doi:10.1080/02773810500191773 CrossRef

Kekäläinen K, Liimatainen H, Illikainen M, Maloney TC, Niinimäki J (2014) The role of hornification in the disintegration behaviour of TEMPO-oxidized bleached hardwood fibres in a high-shear homogenizer. Cellulose 21:1163–1174. doi:10.1007/s10570-014-0210-x CrossRef

Kéri M, Palcsu L, Túri M, Heim E, Czébely A, Novák L, Bányai I (2015) 13C NMR analysis of cellulose samples from different preparation methods. Cellulose 22:2211–2220. doi:10.1007/s10570-015-0642-y CrossRef

Kono H, Yunoki S, Shikano T, Fujiwara M, Erata T, Takai M (2002) CP/MAS 13C NMR study of cellulose and cellulose derivatives. 1. Complete assignment of the CP/MAS 13C NMR spectrum of the native cellulose. J Am Chem Soc 124:7506–7511. doi:10.1021/ja010704o CrossRef

Lai C, Zhang S, Sheng L, Liao S, Xi T, Zhang Z (2013) TEMPO-mediated oxidation of bacterial cellulose in a bromide-free system. Colloid Polym Sci 291:2985–2992CrossRef

Li L, Zhao S, Zhang J, Zhang ZX, Hu H, Xin Z, Kim JK (2013) TEMPO-mediated oxidation of microcrystalline cellulose: influence of temperature and oxidation procedure on yields of water-soluble products and crystal structures of water-insoluble residues. Fibers Polym 14:352–357. doi:10.1007/s12221-013-0352-8 CrossRef

Liu X, Wang L, Song X, Song H, Zhao JR, Wang S (2012) A kinetic model for oxidative degradation of bagasse pulp fiber by sodium periodate. Carbohydr Polym 90:218–223CrossRef

Okita Y, Saito T, Isogai A (2010) Entire surface oxidation of various cellulose microfibrils by TEMPO-mediated oxidation. Biomacromolecules 11:1696–1700CrossRef

Redouan E, Emmanuel P, Michelle P, Bernard C, Josiane C, Cédric D (2011) Evaluation of antioxidant capacity of ulvan-like polymer obtained by regioselective oxidation of gellan exopolysaccharide. Food Chem 127:976–983. doi:10.1016/j.foodchem.2011.01.067 CrossRef

Revol J, Dietrich A, Goring D (1987) Effect of mercerization on the crystallite size and crystallinity index in cellulose from different sources. Can J Chem 65:1724–1725CrossRef

Saito T, Isogai A (2004) TEMPO-mediated oxidation of native cellulose. The effect of oxidation conditions on chemical and crystal structures of the water-insoluble fractions. Biomacromolecules 5:1983–1989CrossRef

Saito T, Isogai A (2006) Introduction of aldehyde groups on surfaces of native cellulose fibers by TEMPO-mediated oxidation. Colloids Surf A 289:219–225. doi:10.1016/j.colsurfa.2006.04.038 CrossRef

Saito T, Nishiyama Y, Putaux J-L, Vignon M, Isogai A (2006) Homogeneous suspensions of individualized microfibrils from TEMPO-catalyzed oxidation of native cellulose. Biomacromolecules 7:1687–1691CrossRef

Saito T, Kimura S, Nishiyama Y, Isogai A (2007) Cellulose nanofibers prepared by TEMPO-mediated oxidation of native cellulose. Biomacromolecules 8:2485–2491CrossRef

Saito T, Hirota M, Tamura N, Kimura S, Fukuzumi H, Heux L, Isogai A (2009) Individualization of nano-sized plant cellulose fibrils by direct surface carboxylation using TEMPO catalyst under neutral conditions. Biomacromolecules 10:1992–1996CrossRef

Shibata I, Isogai A (2003) Depolymerization of cellouronic acid during TEMPO-mediated oxidation. Cellulose 10:151–158CrossRef

Shinoda R, Saito T, Okita Y, Isogai A (2012) Relationship between length and degree of polymerization of TEMPO-oxidized cellulose nanofibrils. Biomacromolecules 13:842–849. doi:10.1021/bm2017542 CrossRef

Sun B, Gu C, Ma J, Liang B (2005) Kinetic study on TEMPO-mediated selective oxidation of regenerated cellulose. Cellulose 12:59–66CrossRef

Sun Y, Zhuang J, Lin L, Ouyang P (2009) Clean conversion of cellulose into fermentable glucose. Biotechnol Adv 27:625–632. doi:10.1016/j.biotechadv.2009.04.023 CrossRef

Sun X-F, Jing Z, Fowler P, Wu Y, Rajaratnam M (2011) Structural characterization and isolation of lignin and hemicelluloses from barley straw. Ind Crops Prod 33:588–598. doi:10.1016/j.indcrop.2010.12.005 CrossRef

Takaichi S, Isogai A (2013) Oxidation of wood cellulose using 2-azaadamantane N-oxyl (AZADO) or 1-methyl-AZADO catalyst in NaBr/NaClO system. Cellulose 20:1979–1988. doi:10.1007/s10570-013-9932-4 CrossRef

Tanaka R, Saito T, Isogai A (2012) Cellulose nanofibrils prepared from softwood cellulose by TEMPO/NaClO/NaClO(2) systems in water at pH 4.8 or 6.8. Int J Biol Macromol 51:228–234. doi:10.1016/j.ijbiomac.2012.05.016 CrossRef

Tsuguyuki S, Masayuki H, Naoyuki T, Akira I (2010) Oxidation of bleached wood pulp by TEMPO/NaClO/NaClO₂ system: effect of the oxidation conditions on carboxylate content and degree of polymerization. J Wood Sci 56:227–232. doi:10.1007/s10086-009-1092-7 CrossRef

Wada M, Sugiyama J, Okano T (1993) Native celluloses on the basis of two crystalline phase (Iα/Iβ) system. J Appl Polym Sci 49:1491–1496CrossRef

Wada M, Okano T, Sugiyama J (1997) Synchrotron-radiated X-ray and neutron diffraction study of native cellulose. Cellulose 4:221–232CrossRef

Wickholm K, Larsson PT, Iversen T (1998) Assignment of non-crystalline forms in cellulose I by CP/MAS 13C NMR spectroscopy. Carbohydr Res 312:123–129. doi:10.1016/S0008-6215(98)00236-5 CrossRef

Zhan H, Liu Q, Chen J, Han Q, Ban W (2010) Pulping principles and engineering. China Light Industry Press, Beijing

Zhao M, Li J, Mano E, Song Z, Tschaen DM, Grabowski EJ, Reider PJ (1999) Oxidation of primary alcohols to carboxylic acids with sodium chlorite catalyzed by TEMPO and bleach. J Org Chem 64:2564–2566CrossRef

Zhou Z, Jaaskelainen A, Vuorinen T (2008) Oxidation of cellulose and carboxylic acids by hypochlorous acid: kinetics and mechanisms. J Pulp Pap Sci 34:212

Titel: Mechanism and kinetics studies of carboxyl group formation on the surface of cellulose fiber in a TEMPO-mediated system
verfasst von: Xiankui Sang
Chengrong Qin
Zhangfa Tong
Song Kong
Zhuan Jia
Guangcong Wan
Xinliang Liu
Publikationsdatum: 07.04.2017
Verlag: Springer Netherlands
Erschienen in: Cellulose / Ausgabe 6/2017
Print ISSN: 0969-0239
Elektronische ISSN: 1572-882X
DOI: https://doi.org/10.1007/s10570-017-1279-9

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