the production of thymoquinone from thymol and carvacrol

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TABLE OF CONTENTS LIST OF FIGURES ......................................................................................................... ix LIST OF TABLES........................................................................................................... xi CHAPTER 1. INTRODUCTION ..................................................................................... 1 CHAPTER 2. CATALYSTS AND ZEOLITE PROPERTIES ........................................ 3 2.1. Definition of Catalyst and Zeolite .......................................................... 3 2.2. Zeolite as Heterogeneous Catalyst.......................................................... 4 2.3. Structural Features of Zeolite ................................................................. 4 2.4. Properties of Zeolite................................................................................ 6 2.5. Design of Stable Heterogeneous Catalysts ............................................. 7 CHAPTER 3. TRANSITION METALS AND COORDINATION CHEMISTRY....... 10 3.1. Definition and Physical Properties of Transition Metals...................... 10 3.2. Electronic Configuration....................................................................... 11 3.3. Oxidation State and Coordination Number .......................................... 13 3.3.1. Oxidation State ............................................................................... 14 3.3.2. Coordination Number ..................................................................... 15 3.4. Types of Ligands .................................................................................. 15 CHAPTER 4. DESIGN OF INTRAZEOLITE COMPLEXES ...................................... 19 4.1. Flexible Ligand (FL) Method ............................................................... 19 4.2. Ligand Synthesis (LS) Method ............................................................. 21 4.3. Zeolite Synthesis (ZS) Method ............................................................. 21 CHAPTER 5. OXIDATION OF MONOTERPENES.................................................... 24 5.1. Definition of Monoterpene ................................................................... 24 5.2. Chemical Composition of Essential Oils.............................................. 25 5.3. Oxidation of Monoterpenes .................................................................. 26 vi
5.4. Catalytic Monoterpene Oxidation with Hydrogen Peroxide ................ 28 CHAPTER 6. EXPERIMENTAL................................................................................... 32 6.1. Materials ............................................................................................... 32 6.2. Methods ................................................................................................ 32 6.2.1. Catalyst Preparations ...................................................................... 32 6.2.1.1. Preparation of Ligand (H2Salpn) ........................................... 32 6.2.1.2. Preparation of Metal Exchanged Zeolite Y ........................... 33 6.2.1.3. Preparation of Encapsulated Complexes ............................... 33 6.2.2. Catalyst Characterization................................................................. 33 6.2.3. Catalytic Activity............................................................................. 34 6.2.3.1. Decomposition of Hydrogen Peroxide 6.2.3.2. Oxidation of Carvacrol and Thymol....................................... 34 6.2.3.3. Heterogeneity Test.................................................................. 35 CHAPTER 7. RESULTS AND DISCUSSION.............................................................. 37 7.1. Catalyst Characterization...................................................................... 37 7.1.1. Elemental Analysis by Inductively Coupled Plasma Analysis....... 37 7.1.2. Scanning Electron Microscopy (SEM) Analysis ............................ 38 7.1.3. X-Ray Diffraction (XRD) Analysis................................................ 40 7.1.4. FTIR Spectroscopy Analysis .......................................................... 43 7.1.5. Pore Volume and Surface Area Measurement................................ 47 7.1.6. Thermal Analysis............................................................................ 47 7.1.6.1. Differential Scanning Calorimetric Analysis of Ligand…….47 7.1.6.2. Thermal Gravimetric Analysis (TGA)……........................... 48 7.2. Catalytic Activities ............................................................................... 50 7.2.1. Decomposition of Hydrogen Peroxide ........................................... 50 7.2.2. Oxidation of Carvacrol ................................................................... 51 7.2.3. Heterogeneity Test.......................................................................... 57 7.2.4. Cr (salpn)-NaY Catalyst Recycle ................................................... 59 7.3. Effect of Parameters for Carvacrol Oxidation Reactions with Selected Cr(Salpn)- NaY Catalyst ..................................................................... 60 7.3.1. Effect of Catalyst Amount ............................................................. 61 7.3.2. Effect of Temperature.................................................................... 62 vii
Page 1 and 2: THE PRODUCTION OF THYMOQUINONE FROM
Page 3 and 4: ACKNOWLEDGEMENTS I would like to ac
Page 5: ÖZET Bu tezde, genel esnek ligand
Page 9 and 10: LIST OF FIGURES Figure Page Figure
Page 11 and 12: LIST OF TABLES Table Page Table 2.1
Page 13 and 14: of thymoquinone are limited only to
Page 15 and 16: advantages compared to homogeneous
Page 17 and 18: NH4 +2 generates the acid sides. Ca
Page 19 and 20: homogeneous internal structures whi
Page 21 and 22: CHAPTER 3 TRANSITION METALS AND COO
Page 23 and 24: not determined by orbital energy al
Page 25 and 26: 3.3.1. Oxidation State The transiti
Page 27 and 28: it surrounds the metal, forms very
Page 29 and 30: metal complexes catalyze the reacti
Page 31 and 32: Figure 4.1. Flexible ligand method:
Page 33 and 34: included in the synthesis mixture.
Page 35 and 36: CHAPTER 5 OXIDATION OF MONOTERPENES
Page 37 and 38: In the GC-MS analysis of the oil of
Page 39 and 40: There are few studies on monoterpen
Page 41 and 42: Homolytic Pathways: Heterolytic Pat
Page 43 and 44: 6.1. Materials CHAPTER 6 EXPERIMENT
Page 45 and 46: inductively coupled plasma spectrom
Page 47 and 48: These tests were performed in detai
Page 49 and 50: Table 7.1. Metal content of encapsu
Page 51 and 52: 7.1.3. X-ray Diffraction (XRD) Anal
Page 53 and 54: Figure 7.2 (cont.) 42
Page 55 and 56: ands observed in the region 1200-16
Page 57 and 58:
Figure 7.5. IR spectra ligand (H2 s
Page 59 and 60:
Figure 7.6. DSC analysis result sho
Page 61 and 62:
7.2. Catalytic Activities 7.2.1. De
Page 63 and 64:
eaction products, among which TQ wa
Page 65 and 66:
carvacrol conversion (%) 16 14 12 1
Page 67 and 68:
e 11.6% with a small amount of THQ.
Page 69 and 70:
during the oxidation process and th
Page 71 and 72:
leaching of Cr (salpn) complexes fr
Page 73 and 74:
7.3.2. Effect of Temperature Four d
Page 75 and 76:
7.4. Oxidation of Thymol Carvacrol
Page 77 and 78:
at 60 o C. Essentail oil contained
Page 79 and 80:
REFERENCES Anthony, F., 1999. Advan
Page 81 and 82:
Martin, R.R.L., Neves, G. 2001. “
Page 83 and 84:
APPENDIX A DETERMINATION OF HYDROGE
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