Crystallization of organic compounds an industrial perspective

Based on the authors hands-on experiences as process engineers, through the use of case studies and examples of crystallization processes, ranging from laboratory development through manufacturing scale-up, this book guides readers through the practical applications of crystallization and emphasises...

Descripción completa

Detalles Bibliográficos
Otros Autores:	Tung, Hsien-Hsin, 1955- author (author), Paul, Edward L., author, Midler, Michael, 1936-2023, author, McCauley, James A., author
Formato:	Libro electrónico
Idioma:	Inglés
Publicado:	Hoboken, N.J. : John Wiley & Sons, Inc [2024]
Edición:	Second edition
Materias:	Crystallization > Industrial applications. Pharmaceutical chemistry. Pharmaceutical industry. Chemistry, Technical Science
Ver en Biblioteca Universitat Ramon Llull:	https://discovery.url.edu/permalink/34CSUC_URL/1im36ta/alma991009757914706719

Tabla de Contenidos:

Cover
Title Page
Copyright Page
Contents
Preface
Chapter 1 Introduction to Crystallization
1.1 Crystal Properties and Polymorphs (Chapters 2 and 3)
1.2 NUCLEATION AND GROWTH KINETICS (CHAPTER 4)
1.3 MIXING AND SCALE-UP (CHAPTER 5)
1.4 Critical Issues and Quality by Design (Chapter 6)
1.4.1 Critical Issues
1.4.2 Design of Experiment
1.5 Crystallization Process Options (Chapters 7-10)
1.5.1 Cooling (Chapter 7)
1.5.2 Evaporation Solvent (Chapter 8)
1.5.3 Antisolvent Addition (Chapter 9)
1.5.4 Reactive Crystallization (Chapter 10)
1.6 Downstream Operations (Chapters 11 And 12)
1.7 Special Applications (Chapter 13)
Chapter 2 Properties
2.1 Solubility
2.1.1 Free Energy-Composition Phase Diagram
2.1.2 Temperature
2.1.3 Solvent
2.1.4 Impurities
2.1.5 Chemical and Physical Structure, Salt and Co-Crystal Form
2.1.6 Solubility Measurement and Prediction
2.1.7 Significance of Crystallization
2.2 Supersaturation, Metastable Zone, and Induction Time
2.2.1 Free Energy-Composition Phase Diagram
2.2.2 Factors Affecting Metastable Zone Width and Induction Time
2.2.3 Measurement and Prediction
2.2.4 Significance of Crystallization
2.3 Oil, Amorphous, and Crystalline States
2.3.1 Phase Diagram
2.3.2 Measurement
2.3.3 Significance to Crystallization
2.4 Polymorphism
2.4.1 Phase Diagram
2.4.2 Measurement and Prediction
2.4.3 Significance to Crystallization and Downstream Operations
2.5 Solvate
2.5.1 Phase Diagram
2.5.2 Measurement and Prediction
2.5.3 Significance to Crystallization and Downstream Operations
2.6 Solid Compound, Solid Solution, and Solid Mixture
2.6.1 Phase Diagram
2.6.2 Measurement and Prediction
2.6.3 Significance to Crystallization
2.7 Inclusion and Occlusion
2.7.1 Mechanism
2.7.2 Measurement.
2.7.3 Significance to Crystallization and Downstream Operations
2.8 Adsorption, Hygroscopicity, and Deliquesce
2.8.1 Phase Diagram
2.8.2 Measurement
2.8.3 Significance to Crystallization and Downstream Operations
2.9 Crystal Morphology
2.9.1 General Observations
2.9.2 Measurement and Prediction
2.9.3 Significance to Crystallization and Downstream Operations
2.10 Partical Size Distribution and Surface Area
2.10.1 Particle Distribution Definition
2.10.2 Measurement
2.10.3 Significance to Crystallization and Downstream Operations
Chapter 3 Polymorphism
3.1 Phase Rule
3.2 Phase Transition
3.2.1 Enantiotropy and Monotropy
3.2.2 Metastable Equilibrium and Suspended Transformation
3.2.3 Measurement
3.3 Prediction of Crystal Structure and its Formation
3.3.1 Equilibrium Approach
3.3.2 Kinetic Approach
3.4 Selection and Screening of Crystal Forms
3.4.1 Selection Criteria
3.4.2 Candidates for Forming Salts and Co-crystals
3.4.3 High Throughput and Process-Based Screening
3.5 Examples
EXAMPLE 3.1
EXAMPLE 3.2
EXAMPLE 3.3
EXAMPLE 3.4
EXAMPLE 3.5
EXAMPLE 3.6
EXAMPLE 3.7
EXAMPLE 3.8
EXAMPLE 3.9
Chapter 4 Kinetics
4.1 SUPERSATURATION AND RATE PROCESSES
4.2 Nucleation
4.2.1 Homogeneous Nucleation
4.2.2 Heterogeneous Nucleation
4.2.3 Secondary Nucleation
4.3 Crystal Growth and Agglomeration
4.3.1 Crystal Growth Mechanisms
4.3.2 Agglomeration Mechanism
4.3.3 Measurement of Crystal Growth Rate
4.3.4 Crystal Population Balance
4.4 Nucleate/Seed Aging and Ostwald Ripening
4.5 DELIVERED PRODUCT: PURITY, CYSTAL FORM, SIZE AND MORPHOLOGY, AND CHEMICAL and PHYSICAL STABILITY
4.6 Design of Experiment (DOE)-Model-Based Approach
4.7 Model-Free Feedback Control
Chapter 5 Mixing and Crystallization
5.1 INTRODUCTION.
5.2 Mixing Considerations and Factors
5.2.1 Mixing Time
5.2.2 Mixing Intensity
5.2.3 Mixing Distribution
5.3 Mixing Effects on Nucleation
5.3.1 Primary Nucleation
5.3.2 Secondary Nucleation and Particle Breakage
5.3.3 Damkoehler Number for Nucleation
5.3.4 Scale-Up of Nucleation-Based Processes
5.4 Mixing Effects on Crystal Growth
5.4.1 Mass Transfer Rate
5.4.2 Da Number for Crystallization
5.4.3 Conflicting Mixing Effects
5.4.4 Experimentation on Mixing Effects
5.4.5 Effects of Mixing on PSD
5.5 Mixing Distribution and Scale-Up
5.5.1 Power
5.5.2 Off-Bottom Suspension
5.6 Crystallization Equipment
5.6.1 Stirred Vessels
5.6.2 Fluidized Bed Crystallizer
5.6.3 Impinging Jet Crystallizer
5.7 Process Design and Examples
EXAMPLE 5.1
EXAMPLE 5.2
Chapter 6 Critical Issues and Quality by Design
6.1 Quality By Design
6.2 Basic Properties
6.2.1 Solubility and Crystal Forms
6.2.2 Particle Size and Morphology
6.3 Seed
6.3.1 Determination of Seed Form, Size, and Quantity
6.3.2 Effectiveness of Seeding
6.4 Supersaturation
6.4.1 Generation of Supersaturation
6.4.2 Oiling Out, Agglomeration/Aggregation
6.4.3 Nucleation
6.4.4 Crystal Growth
6.5 Mixing and Scale-Selection of Equipment and Operating Procedures
6.5.1 Stirred Vessels
6.5.2 In-line Mixers
6.5.3 Fluidized Bed
6.6 Strategic Considerations for Crystallization Process Development
6.7 Summary of Critical Issues
Chapter 7 Cooling Crystallization
7.1 Batch Operation
7.1.1 Rate of Cooling
7.1.2 Metastable Region
7.1.3 Seeding Versus Spontaneous Nucleation
7.1.4 Mixing and Mass Transfer
7.1.5 Solvent
7.1.6 Impurities (Dissolved and Undissolved)
7.2 Continuous Operations
7.2.1 The Attraction of Continuous Processing.
7.2.2 Operating Strategy for Continuous Cooling Crystallizers
7.2.3 Plug Flow and Cascade Operation
7.2.4 Fluidized Bed Continuous Cooling Crystallizer Designs
7.3 Process Design-Examples
EXAMPLE 7.1
EXAMPLE 7.2
EXAMPLE 7.3
EXAMPLE 7.4
EXAMPLE 7.5
EXAMPLE 7.6
Chapter 8 Evaporative Crystallization
8.1 INTRODUCTION
8.2 Solubility Diagrams
8.2.1 Increasing Solubility
8.2.2 Decreasing Solubility
8.2.3 Change in Solvent
8.3 FACTORS AFFECTING NUCLEATION AND GROWTH
8.4 Scale-Up
8.5 Equipment
8.5.1 Heat Transfer
8.5.2 Overconcentration
8.5.3 Combination of Evaporation and Cooling
8.6 Process Design and Examples
EXAMPLE 8.1
EXAMPLE 8.2
EXAMPLE 8.3
Chapter 9 Anti-solvent Crystallization
9.1 Operation
9.1.1 Normal Mode of Addition
9.1.2 Reverse Addition
9.1.3 Simultaneous Mode of Addition
9.1.4 Addition Strategy
9.1.5 Seeding
9.2 IN-LINE MIXING CRYSTALLIZATION
9.3 Process Design and Examples
EXAMPLE 9.1
EXAMPLE 9.2
EXAMPLE 9.3
EXAMPLE 9.4
EXAMPLE 9.5
EXAMPLE 9.6
EXAMPLE 9.7
Chapter 10 Reactive Crystallization
10.1 INTRODUCTION
10.1.1 Utilization
10.1.2 Literature
10.2 Control of Particle Size
10.2.1 Controlling for Growth
10.3 Key Issues in Organic Reactive Crystallization
10.3.1 Mixing Issues
10.3.2 Mixing and Growth
10.3.3 Induction Time and Nucleation
10.3.4 Supersaturation Control
10.3.5 Seeding
10.3.6 Crystal Growth
10.3.7 Impurities/Additives
10.3.8 Secondary Effects
10.4 Creation of Fine Particles-In-Line Reactive Crystallization
10.5 Process Design and Scale-Up
EXAMPLE 10.1
EXAMPLE 10.2
EXAMPLE 10.3
EXAMPLE 10.4
Chapter 11 Filtration
11.1 INTRODUCTION
11.2 BASIC PROPERTIES
11.2.1 Particle Size
11.2.2 Filter Medium
11.2.3 Wash Solvents.
11.2.4 Temperature
11.3 KINETICS
11.3.1 Filtrate Concentration Profile During Filtration/Washing
11.3.2 Filtration and Cake Wash Protocol
11.3.3 Filtration Model
11.3.4 Settling Rate vs Filtration Rate
11.4 process design and scale-up
11.4.1 Agitated Filter Dryer
11.4.2 Centrifuge Filter
11.4.3 Other Operation Complications
Chapter 12 Drying
12.1 INTRODUCTION
12.2 BASIC PROPERTIES
12.2.1 Vapor-Liquid Equilibrium
12.2.2 Solvation and Desolvation
12.2.3 Hardness and Brittleness of Solid Particles
12.2.4 Agglomerates and Granules of Solid Particles
12.3 KINETICS
12.3.1 Drying Profiles
12.3.2 Particle Fracture and Agglomeration
12.3.3 Inter-Relationship Between Drying Stage and Particle Behavior
12.4 PROCESS DESIGN AND SCALE-UP
12.4.1 Process Design
12.4.2 Scale-up
Chapter 13 Special Applications
13.1 INTRODUCTION
13.2 CRYSTALLIZATION WITH SUPERCRITICAL FLUIDS
13.3 Resolution of Stereo-Isomers
13.3.1 Option 1: Use of a Chiral Additive to Create a Diastereoisomeric Set of Compounds
13.3.2 Option 2: Chiral Chemistry to Improve Reaction Chiral Selectivity of the Desired Isomer
13.3.3 Option 3: Kinetic and Dynamic Resolution
13.3.4 Option 4: Use of Chromatography, Membrane, Enzyme, or Other Separation Technology
13.4 WET MILLS IN CRYSTALLIZATION
13.5 COMPUTATIONAL FLUID DYNAMICS IN CRYSTALLIZATION
13.6 Solid Dispersion-Crystalline and/or Amorphous Drugs
13.7 Process Design and Examples
EXAMPLE 13.1
EXAMPLE 13.2
EXAMPLE 13.3
EXAMPLE 13.4
EXAMPLE 13.5
EXAMPLE 13.6
EXAMPLE 13.7
References
Index
EULA.

Crystallization of organic compounds an industrial perspective

Ejemplares similares