Preparation of Bromodeoxycellulose and Derivatives from Shambat Cotton Lint Using Dimethyl Acetamide / Lithium Bromide Solvent System

  • Inaam A. M. Salim 1Department of Chemistry, Faculty of Science, University of Kordofan, El Obeid, Sudan.
  • Yousif A. Ragab Department of Applied Chemistry & Chemical Technology, Facult of Engineering & Technology, University of Gezira, Wad Medani, Sudan

Abstract

This study was designed to prepare cellulose derivatives  with


different   functional  groups  from  Sudanese  Shambat  cotton lint


using   a homogenous   solubilisation  medium. The raw cotton lint


was   mercerized    in   (15%)   NaOH     solution   to   weaken   the


aggregation   of    the   bundles   of   cellulose    fibers;    and    was


subsequently      dissolved      in     N,N-dimethylacetamide/lithium


bromide    (DMA/LiBr)    as    a homogenous      solvent     system.


Bromodeoxycellulose   was    synthesized   by   treatment,   of   the


 


 


solubilised   cotton  cellulose with N-bromosuccinimide (NBS)  in


the    presence   of   triphenylphosphine   (Ph3P)   to   convert   the


hydroxyl  groups  into  the  bromodeoxy  derivative  of   cellulose.


The  chemical   structure  this  derivative  was  investigated  using


infrared  spectroscopy,  elemental  analysis  which  confirmed  the


presence  of  C-Br   bonds.  Thermal   analysis   (TGA,  DSC)  has


shown     that    unlike   chlorordeoxycellulose    and    unmodified


mercerized  cotton, bromodeoxycellulose was relatively thermally


stable.  Azido  and  amino  deoxycellulose  were   easily  prepared


from   bromodeoxycellulose   since   bromide   is  a good  leaving.


Solubility in some organic solvents was tested to explore possible


new uses and applications.

References

Abbott, To, Palmer, Do, Gordon, S. and Bagby , M. (1988),
Solid state of plant polymer by FTIR. Journal of Wood
Chemistry Technology . Vol (8): pp:l-28.
Billmeyer, Fe W, (1984). Textbook of Polymer
Science. (3rd Edition John Wiley & Sons Inc ., Singapore,
pp:151-153.
Buschle-Diller, G. and Zeronian, S.H. (1992). Enhancing the
reactivity and strength of cotton fibres. Journal of Applied
Polymer science, vol 967 - 979.
Furuhata K-1 ., Koganai K., Chang H-U., Aoki N, Sakamoto
M. (1992).
Dissolution of celliilose in lithium bromide-organic solvent
systems and homogenous bromination of cellulose in N-
bromosuccinimide - triphenyl-phosphine in lithium bromide-
N,Nwdimethylacetamide. Carbohydrate Research, 230:165 – 77.
Gandini, A. (2008)0 Polymers from renewable resources: a
challenge for the future of macromolecular materials.
Macromolecules, 41 (24), pp: 9491-9504.



Heinze, T. and Liebert, T. (2001). Unconventional methods in
cellulose functionalization, Progress in Polymers Science,
Vol (2), No. l, pp: 1723 - 1760.

Krylova, K.Ge; Usov, Ael. ayd Suleimanoya, F.R. (1978).
Preparation of 6-Chloro -6- Deoxy - and -6- Iodo -6-
deoxycellulose. Syria Khimicheskayo No. 9, pp: 2158 -
2160.
McCormick, CL. and Callias, P.A. (1987). Derivatization of
cellulose in lithium chloride and N,N-Dimethylacetamide
solutions. Polymer, Vol (28), pp:23 17-23.

Mischnic, P. , and Momclovic, D., (2010). Chemical structure
analysis of starch and cellulose derivatives. Advances in
Carbohydrate Chemistry and Biochemistry, Vol (64), pp: 118
- 184.

Monika, S. and Woolfgang, K., (2008). Thermogravimetric
analysis in combination with FTIR. Water GMBH, Eschborn,
Germany.
Morrison, R, T. and Boyd, N. B. (1992). Organic Chemistry
(6th Edition). Pearson Education Inc.. pp: 175-185.

Nada, A.Aa (2010). The modification of cellulosic surface with
fatty acids via plasma mediated reactions, PhD. Thesis,
University of North Carolina, USA.

Salim, I. A. MO (2012). Preparation of deoxycelluloses from
Shambat cotton lint uslng dimethylacetamide/lithium chloride
and phosphoric acid solvent systems. Ph. D. Thesis,
University of Gezira, Sudan,
Shafizadeh, F., Lai, Y.Z., and Nelson, R.C. (1976)'Thermal
degradation of 6-chlorocarbohydrates, Journal of Applied
Science, Vol. (26), pp: 139
Tseng, He; Ken - Ishi, F.; and Manenori, S. (1994).
Bromination of regenerated chitin with N-bromosuccinimide
And triphenylphosphine homogenous conditions in lithium
bromide N,N- dimethylacetaminde, Carbohydrate Research.
Vol (270). pp: 149 - 161.
WHO the International Pharmacopeia (2011). Oxygen flask
combustion method, fourth edition, pp: 128.
Published
2013-11-07
How to Cite
A. M. SALIM, Inaam; A. RAGAB, Yousif. Preparation of Bromodeoxycellulose and Derivatives from Shambat Cotton Lint Using Dimethyl Acetamide / Lithium Bromide Solvent System. Gezira Journal of Engineering and Applied Sciences, [S.l.], v. 8, n. 2, p. 57 - 84, nov. 2013. ISSN 1858-5698. Available at: <http://journals.uofg.edu.sd/index.php/gjeas/article/view/2138>. Date accessed: 27 oct. 2021.
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