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Batch and Continuous Crystallization of Form II Paracetamol through the Assistance of Additives

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Table of Contents摘要 iAbstract iii誌謝 vTable of Contents viiList of Tables xiiList of Figures xivList of Schemes xxvChapter 1 Introduction 11.1 Pharmaceutical Industry 11.2 Crystallization Process 51.2.1 Fundamental

s of Crystallization 51.2.2 Batch and Continuous Crystallization 111.3 Solid Dosage Forms of API 131.3.1 Polymorphism 141.3.2 Co-crystal 161.4 Paracetamol and Its Polymorphs 181.4.1 Brief Introduction of Paracetamol 181.4.2 Polymorphs of PCA 191.5 Prep

aration of Metastable Form of PCA 211.5.1 Evaporation and Cooling Crystallization without Seeding or Additive 231.5.2 Evaporation and Cooling Crystallization with Seeding 251.5.3 Contact Line Crystallization 261.5.4 Ultrasound-Assisted Crystallization 271.5.5 Heterogene

ous Crystallization 281.5.6 Reaction Coupling 311.5.7 Multicomponent Crystallization 321.5.8 Summary 351.6 Polymorph Assembly by the Presence of Co-former 36Chapter 2 Experimental Procedures 422.1 Chemicals and Solvents 422.2 Experimental Procedures 432.2

.1 Additive Screening for PCA Polymorphs 432.2.2 Effects of the Additive Amounts on the Polymorphic Formation of PCA 442.2.3 Effects of Using ADI, FUM, MLC, SUC and OXADH as Seeds on the Polymorphic Formation of PCA 462.2.4 Solubility Measurements of Form I PCA in Aqueous Soluti

ons of OXA and FUM 472.2.5 Effects of Degrees of Supersaturation on the Cooling Recrystallization of PCA with OXA and FUM 482.2.6 Preparation of PCA Crystals by Cooling Recrystallization in the Aqueous Solutions at pH 1 and 2 482.2.7 Removal of FUM from the Produced Form II

PCA-FUM Mixed Crystals 492.2.8 Cooling Recrystallization of PCA in the Presence of Additives in a 500 mL-sized Stirred Tank 502.2.9 Cooling Recrystallization of PCA in the Presence of FUM in a Tubular Crystallizer 522.2.10 Preparation of PCA-MAL Co-crystals by Cooling Recrysta

llization 552.2.11 Establishment of the Ternary Phase Diagram of PCA-MAL-Water 552.3 Analytical Methods and Instruments 562.3.1 Optical Microscopy (OM) 562.3.2 Fourier Transform Infrared Microscopy (FTIR) 572.3.3 Powder X-ray Diffraction (PXRD) 572.3.4 Thermogravi

metric Analysis (TGA) 582.3.5 Differential Scanning Calorimetry (DSC) 582.3.6 Low-Temperature Differential Scanning Calorimetry (LT-DSC) 592.3.7 Nuclear Magnetic Resonance Spectroscopy (NMR) 592.3.8 High Performance Liquid Chromatography (HPLC) 602.3.9 Photoluminescence

Spectroscopy (PL) 61Chapter 3 Selective Polymorphic Formation of PCA by Additive Addition 623.1 Additive Screening for PCA Polymorphs 623.2 Effects of the Additive Amounts on the Polymorphic Crystallization of PCA 793.3 Effects of Using ADI, FUM, MLC, SUC and OXADH crystals

as Seeds to Induce Form II PCA 883.4 Freezing Point Measurement of the PCA-Additive Aqueous Solutions 933.5 Solubility Diagrams of the PCA-FUM and PCA-OXA Aqueous Solutions 953.6 Effects of Degrees of Supersaturation on the Recrystallization of PCA with FUM and OXA 1063.7 Re

moval of FUM Crystals from the Mixture of Form II PCA and FUM by Solvent Rinsing 113Chapter 4 Preparation of Polymorphic PCA in a Batch and a Continuous Crystallizer 1184.1 Recrystallization of PCA with FUM or OXA in a Stirred Tank 1184.2 Recrystallization of PCA with FUM or OXA in

a Tubular Crystallizer 127Chapter 5 1:1 Co-crystal of PCA-MAL 1365.1 Isomerization of MAL 1365.2 Preparation and Characterization of PCA-MAL Co-crystal 138Chapter 6 Conclusions and Future Works 1476.1 Conclusions 1476.2 Future Works 149Appendices 151A.

Abbreviations and Notations 151B. Thermal Scanning for PCA and Co-former 153C. Form Space Establishment 154D. Crystallographic Data 157E. Solubility Data 158References 161