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(Hyphaene Thebaica) Leaves ﻣﯾﺛﯾ Sudan University of Science and Technology College of Graduate Studies Optimization of Reaction Conditions for Preparing Carboxymethyl Cellulose from Doum palm (Hyphaene thebaica) leaves أمثلة ظروف التفاعل لتحضير كربوكسي ميثيل السليلوز من أوراق الدوم A Dissertation Submitted in Partial Fulfillment of the Requirements of the Master Degree in Chemistry By Abdalwahab Abdalgadier Bsheer Ahmed (BSc., Chemistry-Honours, SUST) Supervisor: Dr. Essa Esmail Mohammad Ahmed October 2020 Dedication To who teach us the deeply meaning of life, To who teach us how to be strong, To my parent, teachers and friends i Acknowledgement First and foremost, I would like to thank Almighty Allah for completing this researh work. I would like to thank Dr.Essa Esmail Mohammed, my supervisor for support and suggestion.My thanks are extended to my colleagues and friends in the Department of Chemistry at Sudan University of science and technology. Finally, a lot of thanks go to Çankırı Karatekin University and Burdur Mehmet Akif Ersoy University in Turkey, especially Dr. Esra Demirdogen for their generous support and helping. ii Abstract In the present study, the synthesis of carboxymethyl cellulose (CMC) from Doum palm (Hyphaene thebaica) leaves as a new source of cellulose was optimized and the produced CMC at optimum conditions was characterized by FTIR, 1H-NMR and TGA. Different solvent mixtures (Ethanol:isopropanol), varying temperatures and reaction time as well as different amounts of monochloro acetic acid (MCAA) were applied. The results showed that the highest degree of substitution (DS) was 1.16. This value was obtained under the following reaction conditions: solvent mixture of (1:1), reaction temperature of 65 ºC, reaction time of 3 hours and MCAA to cellulose ratio of 1:4.5 (moles). The produced CMC (DS1.16) has a creamy color and high water solubility (92%). The FTIR results confirmed the formation of CMC by the presence of carbonyl absorption peak at 1734 cm-1 of carboxymethyl substituent. The TGA results showed that CMC is less thermally stable compared to purified cellulose. iii المستخلص فٍ هذِ انذراست حى ضبظ ظزوف ححضُز كزبىكسٍ يُثُم انسهُهىس يٍ أوراق َخُم انذوو كًصذر جذَذ نهسهُهىس و شخص كزبىكسٍ يُثُم انسهُهىس انًُخج فٍ انظزوف انًثهً بإسخخذاو طُف اﻻشعت ححج انحًزاء وطُف انزٍَُ انًغُطُسً وانخحهُم انحزاري انىسًَ. حى اسخخذاو يخبنُظ يذَببث يخخهفت )اﻹَثبَىل: اﻷَشوبزوببَىل(، درجبث حزارة وأسيبٌ حفبعم يخفبوحت ببﻹضبفت إنً كًُبث يخخهفت يٍ حًض انخهُك أحبدٌ انكهىرو. أظهزث انُخبئج أٌ أعهً درجت إسخبذال (DS) كبَج 7.... حى انحصىل عهً هذِ انقًُت فٍ ظم ظزوف انخفبعم انخبنُت: خهُظ انًذَب ).: .( ، درجت حزارة انخفبعم 76 درجت يئىَت ، سيٍ انخفبعم 3 سبعبث وَسبت MCAA إنً انسهُهىس .: 5.6 )يىل(. َخًُش كزبىكسٍ يُثُم انسهُهىس انًُخج (DS1.16) بهىٌ كزًٍَ وقببهُت عبنُت نهذوببٌ فٍ انًبء )29٪(. أكذث َخبئج طُف اﻻشعت ححج انحًزاء حكىٌ CMC يٍ خﻻل وجىد قًت ايخصبص يجًىعت انكزبىَُم عُذ 835. سى -. نًسخبذل انكزبىكسٍ يُثُم. وأظهزث َخبئج انخحهُم انحزارٌ انىسٍَ أٌ كزبىكسٍ يُثُم انسهُهىس أقم اسخقزا ًرا حزارَبً يقبرَت ببنسهُهىس انًُقً. iv Table of Contents Dedication .............................................................................................................. i Acknowledgement ................................................................................................ii Abstract ............................................................................................................... iii iv ................................................................................................................ انًسخخهص Table of Contents .................................................................................................. v List of Figures ................................................................................................... viii List of Tables ....................................................................................................... ix List of Abbreviations ............................................................................................ x CHAPTER ONE ................................................................................................. 1 Introduction and literature review ......................................................................... 1 1.1 Natural fibers ................................................................................................... 1 1.2 Sources of natural fibers ................................................................................. 1 1.3 Chemical composition of natural fibers: Cellulose ........................................ 2 1.3.1 Source and structure .................................................................................. 2 1.3.2 Crystal structure and morphology of cellulose ......................................... 3 1.3.3 Isolation of cellulose ................................................................................. 4 1.4 Hemicelluloses ................................................................................................ 5 1.5 Lignin .............................................................................................................. 5 1.6 Pectin ............................................................................................................... 5 1.7 Properties of natural plant fibers: physical properties .................................... 5 1.8 Properties of natural plant fibers: Mechanical properties ............................... 6 1.9 Industrial use of natural fibers ........................................................................ 7 1.10 Modification of cellulose .............................................................................. 7 1.10.1 Esterification of cellulose ....................................................................... 8 1.10.2 Alkylation (Methyl cellulose) ................................................................. 9 1.10.3 Hydroxyalkylation .................................................................................. 9 1.10.4 Ionic functionalization .......................................................................... 10 1.10.5 Etherification of cellulose ..................................................................... 11 1.11 Carboxymethylation .................................................................................... 11 v Figure 1.6: The reaction process for the synthesis CMC ................................ 13 1.11.1 Molecular structure of CMC ................................................................. 13 1.11.2 Degrees of substitution in CMC ........................................................... 14 1.11.3 Applications of CMC ............................................................................ 14 1.2 Doum palm (Hyphaene thebaica) tree .......................................................... 17 1.2.1 Description, distribution and uses........................................................... 18 1.3 Previous studies on carboxymethylation of cellulose ............................... 19 1.4 Objectives of the study .................................................................................. 21 CHAPTER TWO .............................................................................................. 22 Materials and methods ........................................................................................ 22 2.1 Sample collection and pretreatments ............................................................ 22 2.2 Chemicals ...................................................................................................... 22 2.3 Chemical composition of Doum palm (Hyphaene thebaica) leaves ............ 22 2.3.1 Extractible contents ................................................................................. 22 2.3.2 Lignin content ......................................................................................... 23 2.3.3 Holocelluloses content ............................................................................ 23 2.3.4 α-Cellulose content ................................................................................. 23 2.3.5 Hemicellulose content............................................................................. 24 2.4 Purification of cellulose from Doum palm leaves ........................................ 24 2.5 Optimization of carboxymethylation reaction of the purified cellulose ....... 24 2.5.1 Effect of solvent ratio on carboxymethylation reaction ......................... 24 2.5.2 Effect of temperature on carboxymethylation reaction .......................... 25 2.5.3 Effect of reaction time on carboxymethylation reaction ........................ 26 2.5.4 Effect of concentration of MCAA on carboxymethylation reaction ...... 26 2.6 Determination of the degree of substitution (DS) ......................................... 27 2.7 Fourier transform infrared spectroscopy ....................................................... 27 2.8 Nuclear magnetic resonance1H-NMR........................................................... 27 2.9 Thermogravimetric analysis .......................................................................... 28 2.10 Viscosity measurements .............................................................................. 28 vi 2.11 Solubility test .............................................................................................. 28 CHAPTER THREE .......................................................................................... 29 Results and discussion .......................................................................................
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