Document Type : Research Paper

Authors

1 Assistant Prof., Polymer Reaction Engineering Department, Faculty of Chemical Engineering, Tarbiat Modares University, Tehran, I.R. Iran

2 -MSc., Polymer Reaction Engineering Department, Faculty of Chemical Engineering, Tarbiat Modares University, Tehran, I.R. Iran

3 Faculty Member, Development Division of Chemical, Polymer and Petrochemical Technology, Research Institute of Petroleum Industry, Tehran, I.R. Iran

4 MSc., Manufacturing Engineering Department, Faculty of Mechanical Engineering, Tarbiat Modares University, Tehran, I.R. Iran

Abstract

In this research, two types of lignin, i.e. one extracted from industrial waste water of the Iran wood and paper (choka) factory as black liquor and another provided from Aldrich company, were studied. Firstly, the lignin was precipitated from its black liquor by a dilute acid and was then purified by dissolving in tetrahydrofuran (THF). Lignin samples were characterized using Fourier transform infrared (FTIR) and proton nuclear magnetic resonance (1HNMR) spectroscopies. It was found from results that the Aldrich lignin has a structure similar with the lignosulfonate while lignin extracted from black liquor does not have a hydrophilic sulfonate group and has a Kraft lignin structure. Using acetylation of Kraft lignin and complementary characterization with 1HNMR spectroscopy, the ratio of hydroxyl functional groups to methoxy groups was calculated to be 1.11 to 1, and amount of the hydroxyl groups was calculated to be 5.91 mmol/g of acetylated lignin, where 53% of the hydroxyl groups is related to the aromatic hydroxyl groups. By having the molecular weight of the Kraft lignin which was obtained from the gel permeation chromatography (GPC) analysis of the acetylated Kraft lignin to be 1260 g/mol, average number of the hydroxyl groups per acetylated lignin chain was calculated to be 7.44.

Keywords

Main Subjects

-Abdulkhani A., Mirshokraie S.A., Hamzeh Y., Hejazi S. and Nouri A., 2011. Elucidation of chemical structure of wood lignin by dissolving in 1-butyl-3-methylimidazolium chloride ionic liquid. Iran J Polym Sci Technol (Persian) 24(4): 279-289.
-Adler, E. and Hernestam, S., 1995. Estimation of phenolic hydroxyl groups in lignin. I. Periodate oxidation of guaiacol compounds. Analytica Chimica Acta, 9 (2): 319-334.
-Andes, M.V., 2008. Lignin separation from kraft black liquors by tangential ultrafiltration. La Chimica e I’Industria, 06(1): 88-95.
-Braunecker, W.A. and Matyjaszewski, K., 2007. “Controlled/living radical polymerization: Features, developments, and perspectives. Progress in Polymer Science, 32(1): 93–146.
-Chen, C.L., Dence, C. and Lin, S., 1992. Methods in Lignin Chemistry. Springer-Verlag, Germany, 578p.
-Diao, B., Zhang, Z., Zhu, J. and Li, J., 2014. Biomass-based thermogelling copolymers consisting of lignin and grafted poly (n-isopropylacrylamide), poly (ethylene glycol), and poly(propylene glycol). RSC Advances, 4(81): 42996–43003.
-Hill, C.A.S., 2007. Various technical lignins. Industrial Crops and Products, 26(2): 116–124.
-Kim, Y.S. and Kadla, J.F., 2010 .Preparation of a thermoresponsive lignin-based biomaterial through atom transfer radical polymerization. Biomacromolecules, 11 (4): 981–988.
-Liu, X., Yin, H., Zhang, Z., Diao, B. and Li, J., 2015. Functionalization of lignin through ATRP grafting of poly(2-dimethylaminoethyl methacrylate) for gene delivery. Colloids and Surfaces B: Biointerfaces, 125(1): 230–237.
-Lu, F., Ralph, J., 2010. Chapter 6- lignin. In: Cereal Straw as a Resource for Sustainable Biomaterials and Biofuels. Amsterdam: Elsevier; pp. 169–207.
-Mansouri, N. and Salvadó J., 2007. Analytical methods for determining functional groups in various technical lignins. Industrial Crops and Products, 26(2): 116-124.
-Mansson, P., 1983. Quantitative determination of phenolic and total hydroxyl groups in lignins. Holzforschung, 37(3): 143-146.
-Matyjaszewski, K. and Xia, J., 2001. Atom transfer radical polymerization. Chemical Reviews, 101(9): 2921–2990.
-Meister J.J., 1991. Addition polymerization of acrylamide, acrylic acid, 2-methoxy ethyl ester and lignin. US3200098.
-Mirshokraie S.A., Larie J., Mostaghni F., Abdulkhani A., 2014. Analysis of photodegraded lignin and lignin model compounds by ATR-FTIR spectroscopy, Iranian Journal of Wood and Paper Science Research (Persian) 29(3): 343-353.
-Mirshokraie S.A., Abdulkhani A. and Karimi A., 2008. Chemical structure elucidation of milled wood lignin and cellulytic lignin from Poplar. Iranian Journal of Wood and Paper Science Research (Persian) 23(2): 102-122.
-Pourmahdi M., 2015. Synthesis of Lignin/Acrylamide Graft Copolymer by Redox Radical Polymerization for Use in the Water-Based Drilling Fluid, MSc Thesis, Tarbiat Modares University, Tehran, Iran.
-Teodorescu, M. and Matyjaszewski, K., 1999 .Atom transfer radical polymerization of (meth) acrylamides. Macromolecules, 32 (15): 4826–4831.
-Thring, R.W., Chornet, E. and Overend, R.P., 1990. Recovery of a solvolytic lignin: effects of spent liquor/acid volume ratio, acid concentration and temperature. Biomass, 23(4): 289–305.
-Zakis, G., 1994. Functional Analysis of Lignins and Their Derivatives. Tappi, USA, 102 p.
-Zeisel, S., 1885. Über ein ve rfahren zum quantitative nachweis von methoxyl. Monatshefte für Chemie, 6(1): 989-996.