The formation of aromatic end group structures in O-alkyl substituted celluloses under alkaline pulping conditions
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Anne Vikkula
Abstract
UV resonance Raman (UVRR) spectroscopy was used to study changes in the structure of reducing end groups of O-alkyl substituted celluloses under conditions simulating the initial phase of soda pulping. The derivatives studied were carboxymethyl cellulose (CMC) with a degree of substitution (DS) of 0.58 and methyl cellulose (MC) with DS of 1.64–1.95. Hot alkaline treatments were carried out in solutions of sodium hydroxide (0.1–1 M) at 95°C in the presence of creosol as a lignin model compound. Alkali-stable aromatic end groups were generated in both cellulose ethers. Moreover, the end groups of methyl cellulose were extensively condensed with creosol. The results demonstrate that aromatisation and condensation depend on the pH and reaction time.
References
Enström, N., Vikkula, A., Teleman, A., Vuorinen, T. (1995) Structure of hemicelluloses in pine kraft cooking liquors. In: Proceedings of the 8th International Symposium on Wood and Pulping Chemistry, Helsinki, Vol. III. pp. 195–200.Search in Google Scholar
Forsskåhl, I., Popoff, T., Theander, O. (1976) Reactions of d-xylose and d-glucose in alkaline, aqueous solutions. Carbohydr. Res.48:13–21.10.1016/S0008-6215(00)83510-7Search in Google Scholar
Fullerton, T.J., Wilkins, A.L. (1985) The mechanism of cleavage of β-ether bonds in lignin model compounds by reducing sugars. J. Wood Chem. Technol.5:189–201.10.1080/02773818508085187Search in Google Scholar
Gierer, J., Wännström, S. (1984) Formation of alkali-stable C-C bonds between wood polymers during kraft pulping. Holzforschung38:181–184.10.1515/hfsg.1984.38.4.181Search in Google Scholar
Halttunen, M., Vyörykkä, J., Hortling, B., Tamminen, T., Batchelder, D., Zimmermann, A., Vuorinen, T. (2001) Study of residual lignin in pulp by UV resonance Raman spectroscopy. Holzforschung55:631–638.10.1515/HF.2001.103Search in Google Scholar
Iversen, T., Wännström, S. (1986) Lignin-carbohydrate bonds in a residual lignin isolated from kraft pulp. Holzforschung40:19–22.10.1515/hfsg.1986.40.1.19Search in Google Scholar
Iversen, T., Westermark, U. (1985) Lignin-carbohydrate bonds in pine lignins dissolved during kraft pulping. Cellulose Chem. Technol.19:531–536.Search in Google Scholar
Johansson, M.H., Samuelson, O. (1977) Alkaline destruction of birch xylan in the light of recent investigations of its structure. Svensk Papperstidn.16:519–524.Search in Google Scholar
Johnson, K.G., Overend, R.P. (1991) Lignin-carbohydrate complexes from Populus deltoides I. Purification and characterization. Holzforschung4:469–475.Search in Google Scholar
Karlsson, O. (1997) Studies on the extent of bonding between lignin and polysaccharides in pulps. Doctoral dissertation. Royal Institute of Technology (KTH), Stockholm. pp. 1–44.Search in Google Scholar
Létumier, F., Ämmänlahti, E., Sipilä, J., Vuorinen, T. (2003) A facile route of formation of lignin-carbohydrate complexes during alkaline pulping. J. Pulp Pap. Sci.29(2):42–47.Search in Google Scholar
Minor, J.L. (1983) Chemical linkage of polysaccharides to residual lignin in pine kraft pulps. In: Proceedings of the International Symposium on Wood and Pulping Chemistry, Japan. pp. 2153–2158.Search in Google Scholar
Ohara, S., Hosoya, S., Nakano, J. (1980) Studies on the formation of lignin-carbohydrate complex during alkaline pulping processes. Mokuzai Gakkaishi26:408–413.Search in Google Scholar
Ragnar, M., Lindgren, C.T., Nilvebrandt, N.-O. (2000) pKa values of guaiacyl and syringyl phenols related to lignin. J. Wood Chem. Technol.20:277–305.10.1080/02773810009349637Search in Google Scholar
Saariaho, A.-M., Jääskeläinen, A-.S., Nuopponen, M., Vuorinen, T. (2003) Ultraviolet resonance Raman spectroscopy in lignin analysis: Determination of characteristic vibrations of p-hydroxyphenyl, guaiacyl and syringyl lignin structures. Appl. Spectrosc.57:58–66.10.1366/000370203321165214Search in Google Scholar PubMed
Sjöström, E. (1993) Wood Chemistry. Fundamentals and Applications. 2nd ed. Academic Press. pp. 136–137.Search in Google Scholar
Valkama, J.-P. (2002) Model compound studies of the formation of C-C bonds between lignin and polysaccharide under kraft pulping conditions. Master's thesis, Helsinki University of Technology, Espoo.Search in Google Scholar
Vikkula, A. (1999). Hemicelluloses in kraft cooking liquors. Licentiate's thesis, Helsinki University of Technology, Espoo. pp. 68–71.Search in Google Scholar
Vikkula, A., Létumier, F., Tenkanen, M., Sipilä, J., Vuorinen, T. (2001) Generation of phenol-xylan complexes in kraft pulping conditions. In: Proceedings of the 11th International Symposium on Wood and Pulping Chemistry (ISWPC), Nice, Vol. 1. pp. 51–54.Search in Google Scholar
Vikkula, A., Valkama, J., Vuorinen, T. (2006) Formation of aromatic and other unsaturated end groups in carboxymethyl cellulose during hot alkaline treatment. Cellulose, in press.10.1007/s10570-005-9024-1Search in Google Scholar
Yamasaki, T., Hosoya, S., Chen, C.-T., Gratzl, J.S., Chang, H. (1981) Characterization of residual lignin in kraft pulp. In: Proceedings of the International Symposium On Wood and Pulping Chemistry, Stockholm, Vol. II. pp. 34–42.Search in Google Scholar
©2006 by Walter de Gruyter Berlin New York
Articles in the same Issue
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Articles in the same Issue
- Upgrading of paper-grade pulps to dissolving pulps by nitren extraction: Optimisation of extraction parameters and application to different pulps
- De-esterification and sulfonation in spruce CTMP: Effects on pulp and paper properties
- The nature of chromophores in high-extractives mechanical pulps: Western red cedar (Thuja plicata Donn) chemithermomechanical pulp (CTMP)
- On the relationship between fibre length, cellulose chain length and pulp viscosity of a softwood sulfite pulp
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- Kraft pulp from budworm-infested Jack pine
- Elucidation of the structure of cellulolytic enzyme lignin
- Effect of acetyl groups on enzymatic hydrolysis of cellulosic substrates
- NIR PLSR results obtained by calibration with noisy, low-precision reference values: Are the results acceptable?
- The hydration of paper studied with solid-state magnetisation-exchange 1H NMR spectroscopy
- Impact of drying temperature and pressing time factor on VOC emissions from OSB made of Scots pine
- Factors influencing timber gluability with one-part polyurethanes – studied with nine Australian timber species
- Mechanical characterisation of wood-adhesive interphase cell walls by nanoindentation
- Parameters of wood welding: A study with infrared thermography
- Polycarboxylic acids as non-formaldehyde anti-swelling agents for wood
- Influence of variation in modulus of elasticity on creep of wood during changing process of moisture
- Permeability changes in heartwood of Picea abies and Abies alba induced by incubation with Physisporinus vitreus
- Combined effect of boron compounds and heat treatments on wood properties: Boron release and decay and termite resistance
- Antioxidant activity of extracts from the bark of Chamaecyparis lawsoniana (A. Murray) Parl.
- Obituary Carlton W. Dence (1926–2006)
- Characteristics of NAEM salt-catalyzed alcohol organosolv pulping as a biorefinery
