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Synthesis and Characterization of Protic Ammonium Based Ionic Liquids

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Synthesis and Characterization of Protic Ammonium Based Ionic Liquids SYNTHESIS AND CHARACTERIZATION OF PROTIC AMMONIUM BASED IONIC LIQUIDS M. Sc THESIS A DISSERTATION SUBMITTED FOR THE PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE (M. Sc) IN ORGANIC CHEMISTRY SUBMITTED BY KHADIZA STUDENT ID: 0416032602F REGISTRATION NO: 0416032602 SESSION: APRIL’ 2016 MAY, 2019 ORGANIC CHEMISTRY RESEARCH LABORATORY DEPARTMENT OF CHEMISTRY BANGLADESH UNIVERSITY OF ENGINEERING AND TECHNOLOGY BUET DHAKA-1000 i Dedicated To ii iii DEPARTMENT OF CHEMISTRY BANGLADESH UNIVERSITY OF ENGINEERING AND TECHNOLOGY BUET DHAKA-1000 STUDENT’S DECLARATION I hereby certify that this material, which I now submit for assessment on the program of study leading to the award of M.Sc is entirely my own work, and I also declare this thesis or any part of it has not been submitted elsewhere for the award of any degree or diploma. Signature of the Student Date: ……………….. .………………...………… KHADIZA (Candidate) ID No. : 0416032602F Session: April‟2016 Department of Chemistry BUET, Dhaka-1000 iv ABSTRACT Ionic Liquids (ILs) have attracted extensive research interest in recent years as environmentally benign solvents and it has also been considered as the “engineering solvents” having its tunable physical and chemical properties. ILs are typically consist of organic nitrogen-containing heterocyclic/aliphatic cations and inorganic or organic anions. The ILs designed and synthesized for carrying out specified task are referred as functionalized ILs, which show great application potential in various processes. The efforts to produce functionalized ILs, characterized them, and evaluate their properties and applications are presented in this thesis. A series of Seven (7) achiral and chiral protic diisopropylethylammonium based ILs were designed, synthesized and characterized. Out of these six are achiral, one is chiral based ILs. All diisopropylethylammonium based ILs were characterized by analytical data obtained from: FT-IR, UV-VIS, 1H-NMR spectroscopy. Anti-microbial and toxicity studies were carried out using the well-diffusion technique with ILs solutions of two different concentrations. The six human pathogens were as follows: Bacillus cereus (+), Staphylococcus aureus (+), Sarcina lutea (+), Eschericia coli (-), Salmonella typhi (-), Pseudomonas aeruginosa (-). Two protic Diisopropylethylammonium based ILs were chosen to employ in Mannich reaction to synthesis of β-amino carbonyl compounds and esterification reaction. The synthesized protic ionic liquids (PILs) showed catalytic effect on Mannich reaction and esterification reaction in very short time. Keywords: Ionic liquids, Engineering solvent, Mannich reaction, β-amino carbonyl compound, Esterification reaction, Diisopropylethylammonium cation. v ACKNOWLEDGEMENT First and Foremost, I would like to thank to my honorable supervisor Prof. Dr. Md. Wahab Khan for giving me the opportunity to work in his group and for his continuous guidance throughout my MS study and research. His supportive discussions and enthusiasm for chemistry always replenished my energy to work. I would like to thank his mercy tolerating the impurity of my ILs. Besides my supervisor, I would like to thank my course teachers: Prof. Dr. Nazrul Islam, Prof. Dr. Abdur Rashid, Prof. Dr. Shakila Rahman and Dr. Ayub Ali, for their help and advice. I desire to offer my pleasant thanks to Prof. Dr. M. A. Rashid, Department of pharmacy (State University Bangladesh), for his kind help to carry out biological test of various synthesized ILs. I am thankful to Bangladesh University of Engineering and Technology (BUET) for financial support. I would also like to thank all staffs Department of Chemistry at BUET for their enormous support. Special thanks to Mr. Monir Uzzaman, Department of Chemistry at BUET, Dhaka for his cooperation in taking FT-IR spectrums. I am thankful to my fellow lab mates in ionic liquids research laboratory (ILRL): Md. Jahirul Islam, Walid Bin Kader, Maidul Islam, Mithy, Ajoy Kumer, Asutosh Nath, Laila Afrin, Saidul Islam for their friendly behavior and fruitful suggestions. In particular, I am grateful to Md. Jahirul Islam (for any organic synthesis problem sessions), Ashutosh Nath (for technical problem sessions) and Ajoy Kumer (for the help during my thesis writing). Lastly, I am very grateful to my family for giving me inspiration, advice and for their great sacrifice and parents supporting me spiritually throughout my life. Author (Khadiza) vi Compounds List in this Thesis Code No. Compound name Abbreviation No. K-IL01 N,N-Diisopropylethylammonium formate [DIPEAH][F] 1 K-IL02 N,N-Diisopropylethylammonium acetate [DIPEAH][A] 2 K-IL03 N,N-Diisopropylethylammonium propionate [DIPEAH][P] 3 K-IL04 N,N-Diisopropylethylammonium butyrate [DIPEAH][B] 4 K-IL05 N,N-Diisopropylethylammonium trifluoroacetate [DIPEAH][TFA] 5 K-IL06 N,N-Diisopropylethylammonium 2- [DIPEAH][2BrP] 6 bromopropionate K-IL07 N,N-Diisopropylethylammonium 2-chloroacetate [DMAPyH][2ClA] 7 vii CONTENT ABSTRACT ....................................................................................................................... v ACKNOWLEDGEMENT ................................................................................................. vi COMPOUND LIST ........................................................................................................ vii ABBREVIATION .............................................................................................................xi CHAPTER 1 INTRODUCTION TO IONIC LIQUIDS 1. Introduction to ionic liquids… ..................................................................................... 01 What is an ionic liquid ................................................................................................ 01 Brief history of ionic liquids ....................................................................................... 02 Types of ionic liquids...................................................................................................03 Quarternary Ammonium based ILs… ......................................................................... 06 Properties of ILs .......................................................................................................... 07 General Properties of ammonium ILs… ........................................................................ 16 Importance of ionic liquids in organic synthesis ......................................................... 17 Method of synthesis .................................................................................................... 31 Synthesis of Ammonium ILS .......................................................................................... 33 CHAPTER 2 PRESENT WORK Title ............................................................................................................................. 35 Rationale ..................................................................................................................... 36 EXPERIMENTAL .............................................................. 37 Materials and Methodology ....................................................................................... 38 General procedure of N,N-Diisopropylethylammonium based ILs ............................. 38 General procedure of of N,N-Diisopropylethylammonium trifluroacetate .............. 41 viii General procedure of N,N-Diisopropylethylammonium 2-bromopropionate .......... 42 General procedure of N,N-Diisopropylethylammonium 2-chloroacetate ................ 43 Synthesis of Mannich base...........................................................................................43 Synthesis of ester ......................................................................................................... 44 RESULTS AND DISCUSSION .............................................. 46 Characterization of N,N -Diisopropylethylammonium trifluroacetate ........................ 47 Characterization of N,N-Diisopropylethylammonium 2-bromopropionate ............. 48 Characterization of N,N -Diisopropylethylammonium 2-chloroacetate ................... 49 Characterization of ester (E -01) .................................................................................. 51 Characterization of 2- amino carbonyl compound, (MB-01) ..................................... 52 CHAPTER 3 BIOLOGICAL EVALUATION OF IONIC LIQUIDS Introduction… ............................................................................................................. 79 Literature review… ..................................................................................................... 79 Antimicrobial agents ................................................................................................... 80 3.3.1 Antibacterial agents… .............................................................................................. 81 Biological applications of AMMONIUM based ILs… ................................................ 82 Methods for antimicrobial activity evaluation of ILs ................................................. 83 Disc diffusion method ......................................................................................................... 83 Broth and agar dilution method ...................................................................... 85 Agar diffusion method .................................................................................... 85 Dilution method .............................................................................................. 86 Antimicrobial
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