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Methods in Lignin Chemistry

Author: Stephen Y Lin; Carlton W Dence
Publisher: Berlin, Heidelberg : Springer Berlin Heidelberg, 1992.
Series: Springer series in wood science.
Edition/Format:   eBook : Document : EnglishView all editions and formats
The structural complexity of lignin has continually challenged the ingenuity of researchers to develop suitable methods for its characterization prior to and following a wide variety of chemical, biological, and physical treatments. Provided here is an up-to-date compilation of lignin methodology. Theoretical background and practical procedures are combined and - whenever possible - a procedure is presented in  Read more...

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Genre/Form: Electronic books
Additional Physical Format: Print version:
Material Type: Document, Internet resource
Document Type: Internet Resource, Computer File
All Authors / Contributors: Stephen Y Lin; Carlton W Dence
ISBN: 9783642740657 3642740650
OCLC Number: 851813665
Description: 1 online resource (xxx, 578 pages 190 illustrations).
Contents: 1 Introduction.- 1 Introduction.- 1.1 General Structural Features of Lignin.- 1.2 Variations in Concentration and Composition of Lignin in Xylem.- 1.3 Isolation and Recovery of Lignin.- 1.4 Physical Properties of Lignin.- 1.5 Structure-Modifying Reactions.- 1.5.1 Modification of the Aromatic Ring.- Electrophilic Substitution.- Conversion of Aromatic Rings to Nonaromatic Cyclic Structures.- Conversion of Cyclic to Acyclic Structures.- Ring Coupling and Condensation Reactions.- 1.5.2 Modification of the Propanoid Side Chain.- Cleavage of Ether Bonds.- Cleavage of Carbon-Carbon Bonds.- Substitution Reactions.- Formation and Elimination of Multiple Bond Functionalities.- 1.5.3 Future Analytical Needs.- References.- 2 Detection and Determination.- 2.1 The Detection of Lignin.- 2.1.1 Introduction.- 2.1.2 Reagents for the Detection of Lignin.- Aliphatic Compounds.- Phenols and Aromatic Amines.- Heterocyclic Compounds.- Inorganic Reagents.- Unclassified Reagents.- 2.1.3 Color-Forming Reaction Sequences.- 2.1.4 Procedures for the Detection of Lignin.- Color Reaction with Phloroglucinol-Hydrochloric Acid.- The Maule Color Reaction.- The Cross and Bevan Color Reaction.- Color Reaction with Tosyl Chloride/Pyridine, p-Nitrosodimethylaniline/Potassium Cyanide.- Color Reaction with Quinone Monochlorimide.- Color Reaction with Potassium Nitrosodisulfonate.- Color Reaction Based on the Formation of Nitrosophenols (Pearl-Benson Method).- References.- 2.2 The Determination of Lignin.- 2.2.1 Introduction.- 2.2.2 Direct Methods.- Acid Hydrolysis of Wood and Pulp.- Determination of Acid-Insoluble (Klason) Lignin in Wood and Pulp.- Determination of Acid-Soluble Lignin in Wood and Pulp.- Acid Hydrolysis of Annual Plants, Developing Wood, and Forage.- Determination of Acid-Insoluble Lignin in Annual Plants, Developing Wood, and Forage.- 2.2.3 Indirect Methods.- Spectrophotometric Methods.- Determination of Lignin in Wood and Pulp by the Acetyl Bromide Method.- Methods Based on Oxidant Consumption.- Determination of the Kappa Number of Pulp.- 2.2.4 Determination of Lignin in Solution.- Determination of Dissolved Lignin by the Modified Pearl-Benson (Nitrosation) Method.- References.- 3 Isolation and Purification.- 3.1 Wood.- 3.1.1 Introduction.- 3.1.2 Preferred Method for Isolation and Purification of Lignin.- Isolation.- Purification.- 3.1.3 Discussion.- Modifications of and Comments on the Preferred Method.- Milled Wood Lignin as a Representative of the Lignin in Wood.- Milled Wood Lignin Compared with Brauns Lignin.- Milled Wood Lignin Compared with Cellulolytic Enzyme Lignin.- References.- 3.2 Isolation of Lignin from Pulp.- 3.2.1 Introduction.- 3.2.2 Procedures.- Preparation of Pulp Samples and Enzyme Solution.- Isolation of Residual Lignins in Unbleached Pulps.- Isolation of Residual Lignins from Semi-Bleached Pulps.- Purification of the Residual Lignins.- 3.2.3 Concluding Remarks.- References.- 3.3 Commercial Spent Pulping Liquors.- 3.3.1 Introduction.- 3.3.2 Principle.- Kraft (Sulfate) Lignin.- Lignosulfonate (Sulfite Lignin).- 3.3.3 Methods.- Isolation Procedure for Kraft Lignin.- Isolation Procedure for Lignosulfonates.- 3.3.4 Composition of Isolated Lignin.- Kraft Lignin Fractions.- Lignosulfonate Fractions.- 3.3.5 Discussion.- References.- 4 Characterization in Solid State.- 4.1 Fourier Transform Infrared Spectroscopy.- 4.1.1 Principles and Instrumental Techniques.- Introduction.- Scope of FTIR Spectroscopic Applications.- Description of a Standard FTIR Instrument.- Advantages of FTIR Spectroscopy.- 4.1.2 Method.- FTIR Spectroscopy in Practice.- Procedures.- 4.1.3 Lignin Characterization in the Mid-Infrared Region (4000?500 cm?1).- Band Assignment and Classification of Lignin IR Spectra.- Influence of Carbonyl Groups.- Mathematical Resolution of Spectra.- Effect of Acetylation.- Quantitative Evaluation.- 4.1.4 Lignin Spectra in the Near-Infrared Region (4000?10000 cm?1).- 4.1.5 Lignin Spectra in the Far-Infrared Region (50?500 cm?1).- 4.1.6 Concluding Remarks.- References.- 4.2 Ultraviolet Microscopy.- 4.2.1 Introduction.- 4.2.2 Information Obtained by UV Microscopy.- Photomicrographs.- Lignin Concentration.- UV Absorption Spectra.- 4.2.3 Experimental Methods.- Specimen Preparation.- Photography.- Quantitative Analysis.- 4.2.4 Concluding Remarks.- References.- 4.3 Interference Microscopy.- 4.3.1 Introduction.- 4.3.2 Principle.- 4.3.3 Method.- Specimen Preparation.- Measurement of Refractive Index.- Calculation of Lignin Concentration from Refractive Index.- Measurement of Porosity.- Calculation of Lignin Concentration from Porosity.- 4.3.4 Discussion.- Comparison with Other Techniques.- Types of Specimen that Can be Examined.- Accuracy and Precision.- References.- 4.4 Electron Microscopy.- 4.4.1 Introduction.- 4.4.2 Principles.- Glossary.- Principles of SEM-EDXA and TEM-EDXA.- 4.4.3 Methods.- Specimen Thickness.- Procedure for Bromination-EDXA.- 4.4.4 Lignin Distribution in Cell Walls.- Softwoods.- Hardwoods.- Distribution of Lignin.- Distribution of Guaiacyl and Syringyl Lignins.- 4.4.5 Comparisons of Bromination-EDXA with Other Methods.- References.- 4.5 Cross Polarization/Magic Angle Spinning Nuclear Magnetic Resonance (CP/MAS NMR) Spectroscopy.- 4.5.1 Introduction.- 4.5.2 Principle of CP/MAS NMR.- Cross Polarization.- Magic Angle Spinning.- 4.5.3 Description of Methods for CP/MAS NMR Spectroscopy.- Choice of Spectrometer.- Sample Preparation.- Determination of Lignin in Wood and Pulp.- Interrupted Decoupling.- Estimation of Syringyl/Guaiacyl Ratios.- Estimation of the Degree of Etherification.- Resolution Enhancement.- 4.5.4 Discussion.- 4.5.5 Future Developments.- References.- 4.6 Raman Spectroscopy.- 4.6.1 Introduction.- 4.6.2 Principle.- 4.6.3 Method.- Raman System.- Scattering Geometries.- Specimens and Sampling.- 4.6.4 Spectral Information.- Identification of Native Lignin Features.- Quantitative Analysis of Lignin in Wood.- Orientation and Composition Studies of Lignin in Woody Tissue.- 4.6.5 Discussion.- Comparison with Other Techniques.- Future Development.- References.- 4.7 Pyrolysis-Gas Chromatography-Mass Spectrometry.- 4.7.1 Introduction.- 4.7.2 Principle and Methods of Analytical Pyrolysis.- Combination of Pyrolysis with Other Instruments.- Pyrolysis Techniques.- Induction Heating (Curie-Point Pyrolysis).- Resistance Heating.- Sample Preparation, Size, Geometry, and Contamination: General Considerations.- 4.7.3 Gas Chromatography.- Operating Conditions.- 4.7.4 Mass Spectrometry.- Instrumentation.- Ionization.- Data Handling.- 4.7.5 Evaluation of Pyrograms and Spectra.- 4.7.6 Utility of the Method.- References.- 4.8 Thermal Analysis.- 4.8.1 Introduction.- 4.8.2 General Principles and Techniques of Thermal Analysis.- Thermogravimetry.- Apparatus.- TG Curve.- Factors Affecting TG Measurements.- DTA and DSC.- Apparatus.- DTA and DSC Curves.- Factors Affecting DTA and DSC Measurements.- 4.8.3 Applications of Thermal Analysis to Lignin.- Kinetic Study of the Thermal Degradation of Lignin.- Glass Transition of Lignin.- Heat Capacity of Lignin.- 4.8.4 Conclusions.- References.- 5 Characterization in Solution: Spectroscopic Methods.- 5.1 Ultraviolet Spectrophotometry.- 5.1.1 Introduction.- 5.1.2 Principle of Measurement.- 5.1.3 Method.- Solvent Selection.- Preparation of Solutions for Spectral Measurements.- Procedure for Quantitative Determination (Neutral Spectra).- Procedure for Measurement of Ionization Difference Spectra.- Second Derivative Photometry.- 5.1.4 Ultraviolet Absorption Characteristics of Lignins and Lignin-Related Model Compounds.- Solvent Effect.- Absorption Bands.- Ionization Difference Spectra.- NaBH4 Reduction Difference Spectra.- Second Derivative Photometry.- The Effect of Chemical Modification on Ultraviolet Absorption.- 5.1.5 Discussion.- References.- 5.2 Fourier Transform Infrared Spectroscopy.- 5.2.1 Introduction.- 5.2.2 Method.- Transmission Cells.- Attenuated Total Reflection (ATR).- Circular Attenuated Total Reflection (CATR).- 5.2.3 Liquid State FTIR Spectroscopy of Lignins.- Acetylated Lignins in Chloroform.- Lignosulfonates in Water.- Lignins in Alkaline Solutions.- FTIR Spectra of Pulping Liquors.- References.- 5.3 Proton (1H) NMR Spectroscopy.- 5.3.1 Introduction.- 5.3.2 Description of Preferred Method.- Acetylation.- Purification of the Acetate Derivative.- NMR Examination.- 5.3.3 Discussion.- Comments on the Preferred Method.- Alternative Conditions for the Recording of Spectra.- References.- 5.4 Carbon-13 Nuclear Magnetic Resonance Spectrometry.- 5.4.1 Introduction.- 5.4.2 Principles of Pulsed Fourier Transform 13C NMR.- Glossary of Terms and Symbols.- Basic Principles and Elements of an NMR Experiment.- Pulsed NMR in the Rotating Frame of Reference.- Relaxation Times.- Acquisition of the Free Induction Decay (FID) and Fourier Transformation (FT) of the FID.- Chemical Shifts.- Spin-Spin Couplings: Scalar and Dipolar.- Signal Intensities.- One- and Two-Dimensional NMR Experiments.- 5.4.3 Experimental Procedures.- Preparation of Samples.- Spectrometer Specifications.- Recording of 13C NMR Spectra: Summary of Acquisition Parameters.- Routine Spectra.- Spectra for Quantitative Analysis.- DEPT (Distortionless Enhancement by Polarization Transfer) Spectra.- Integration of NMR Signals.- 5.4.4 Results and Discussion.- Qualitative Analysis.- 13C NMR DEPT Spectra.- Quantitative Analysis.- 5.4.5 Concluding Remarks.- References.- 5.5 Electron Spin Resonance (ESR) Spectroscopy.- 5.5.1 Introduction.- 5.5.2 Principle of ESR.- 5.5.3 Spectral Parameters.- The g-Value.- Intensity.- Line Shape.- Hyperfine Structure.- 5.5.4 Methods.- Sample Preparation.- ESR Measurements.- ESR Operation.- 5.5.5 ESR of Lignin.- Detection of Mechanoradicals in Lignin.- Detection of Free Radicals in Photoirradiated Lignin.- Detection of Free Radicals in a Photoirradiated Lignin Model Compound.- 5.5.6 Discussion.- References.- 6 Characterization in Solution: Chemical Degradation Methods.- 6.1 Acidolysis.- 6.1.1 Introduction.- 6.1.2 Characterization of Lignins by Analysis of Low-Molecular Weight Acidolysis Products.- 6.1.3 Applications of the Acidolysis Method.- 6.1.4 Preferred Acidolysis Procedure.- Preparation of the Acidolysis Reagent.- Acidolysis Reaction.- Work-Up of Acidolysis Mixture.- Analysis of Acidolysis Products.- 6.1.5 Discussion of Procedure.- 6.1.6 Dimeric Acidolysis Products.- References.- 6.2 Nitrobenzene and Cupric Oxide Oxidations.- 6.2.1 Introduction.- Nitrobenzene Oxidation.- Cupric Oxide Oxidation.- Nitrobenzene and Cupric Oxide Oxidations of Lignins in Grass Tissues.- 6.2.2 Experimental Procedures.- Sample Preparation.- Nitrobenzene Oxidation.- Cupric Oxide Oxidation.- Qualitative Determination of Oxidation Products.- Gas Chromatography (GC).- Gas Chromatography-Mass Spectrometry (GC-MS).- Quantitative Determination of Oxidation Products.- Gas Chromatography (GC).- High Performance Liquid Chromatography (HPLC).- Determination of p-Hydroxycinnamic Acid and Ferulic Acid Ester Units in Grass Lignins.- Interpretation of Mass Spectra.- 6.2.3 Discussion of the Methods.- References.- 6.3 Chemical Degradation Methods: Permanganate Oxidation.- 6.3.1 Introduction.- 6.3.2 Experimental Procedure.- Preparation of Samples.- Alkylation.- Oxidation with Potassium Permanganate.- Oxidation with Hydrogen Peroxide.- Esterification.- Gas Chromatographic Analysis.- 6.3.3 Discussion of Method.- Reaction Selectivity.- Identification and Estimation of Structural Unit Types.- Estimation of Phenolic Hydroxyl Groups.- References.- 6.4 Thioacidolysis.- 6.4.1 Introduction.- 6.4.2 Thioacidolysis Reactions of Lignin.- 6.4.3 Description of Method.- Reagents.- Treatment of Lignin with Thioacidolysis Reagent.- GC Analysis of Monomeric Products.- Quantitative Determination of the Main Monomeric Products.- 6.4.4 Discussion of Method.- Sensitivity and Reproducibility.- Identification of the Major Thioacidolysis Products.- Quantitative Aspects of the Thioacidolysis Method.- References.- 6.5 Hydrogenolysis.- 6.5.1 Introduction.- 6.5.2 Proposed Sequence for Hydrogenolysis.- 6.5.3 Hydrogenolysis and Hydrogenation Reactions.- Cleavage of Interunitary Linkages.- Hydrogenation of Side Chain and Aromatic Ring.- 6.5.4 Factors Affecting Hydrogenolysis.- Catalyst Activity.- Catalyst Amount.- Hydrogen Pressure.- Solvent.- 6.5.5 Hydrogenolysis to Monomeric Products.- 6.5.6 Hydrogenolysis to Dimeric and Trimeric Products.- References.- 6.6 Nucleus Exchange Reaction.- 6.6.1 Introduction.- 6.6.2 Reaction Mechanism.- Phenolation.- Nucleus Exchange.- Demethylation.- The Response of Various Structural Units in Lignins to the NE Treatment.- 6.6.3 Description of the NE Method.- Sample Preparation.- Preparation of Reagent.- Description of Procedure.- Quantitative Analysis of Products by Gas Chromatography.- 6.6.4 Quantitative Determination of Noncondensed and Condensed Guaiacyl Nuclei in Softwood Protolignins.- 6.6.5 Quantitative Determination of Noncondensed and Condensed Phenyl Nuclei in Hardwood Protolignins.- 6.6.6 Discussion of Method.- Confirmation of the Quantitative Nature of the NE Reaction.- Use of the NE Method.- References.- 6.7 Ozonation.- 6.7.1 Introduction.- 6.7.2 Mechanism of Ozonation.- 6.7.3 Factors Involved in the Design of an Ozonation Procedure.- Conditions Used for the Reaction with Ozone.- Work-Up of Ozonation Product Mixtures.- Procedures for Separation and Identification of Ozonation Products.- Procedures for Quantitative Determination of Ozonation Products.- 6.7.4 Ozonation Procedure.- Ozonation, Saponification, and Derivatization.- Gas Chromatography and Gas Chromatography-Mass Spectrometry.- 6.7.5 Information on the Structure of the Lignin Side Chain.- 6.7.6 Conclusion.- References.- 7 Functional Group Analysis.- 7.1 Determination of Total and Aliphatic Hydroxyl Groups.- 7.1.1 Introduction.- 7.1.2 Determination of Total Hydroxyl Groups.- Acetylation of the Lignin Preparation.- Determination of Total O-Acetyl Groups.- The Kuhn-Roth Procedure.- The Modified Bethge-Lindstroem Procedure.- Total Hydroxyl Content.- Total Aliphatic Hydroxyl Content.- 7.1.3 Discussion of the Methods.- Precision and Accuracy of the Methods.- In-House as Opposed to Commercial O-Acetyl Analysis.- References.- 7.2 Determination of Phenolic Hydroxyl Groups.- 7.2.1 Significance of the Analysis.- 7.2.2 Survey of Analytical Approaches.- 7.2.3 Description of Procedures.- Aminolysis.- Instrumentation and Chemicals.- Calibration of Internal Standard.- Procedure.- Periodate Oxidation.- Instrumentation and Chemicals.- Calibration of Internal Standard.- Procedure.- Calculation.- 7.2.4 Discussion of Methods.- References.- 7.3 Determination of Ethylenic Groups.- 7.3.1 Ethylenic Structures in Lignin.- 7.3.2 Survey of Methods.- 7.3.3 Determination of Total Cinnamaldehyde and Cinnamyl Alcohol Units.- Pre-Reduction of Carbonyl Groups with Lithium Aluminum Hydride.- Catalytic Hydrogenation.- Measurement of Hydrogenation Difference Spectrum.- 7.3.4 Determination of Stilbenoid Units.- Pre-Reduction of Carbonyl Groups with Lithium Aluminum Hydride (LiAlH4).- Measurement of Ionization Difference Spectrum.- 7.3.5 Discussion of Procedures.- References.- 7.4 Determination of Carbonyl Groups.- 7.4.1 Introduction.- 7.4.2 Proposed Methods for the Determination of Carbonyl Groups.- 7.4.3 Determination of Total Carbonyl Content of Lignins by Reaction with Hydroxylamine Hydrochloride.- 7.4.4 Determination of Conjugated Carbonyl Groups by UV Spectroscopy.- Preparation of Lignin Sample Stock Solution.- UV Spectrum of Lignin in Alkaline Solution.- UV Spectrum of Sodium Borohydride-Reduced Lignin in Alkaline Solution.- Reduction Difference (??r) Spectrum.- Calculation of the Conjugated Carbonyl Contents.- 7.4.5 Discussion of the Methods.- Comparison of the Hydroxylamine Hydrochloride and Borohydride Methods.- Accuracy of the Procedure for Determining Conjugated Carbonyl Groups.- References.- 7.5 Determination of Carboxyl Groups.- 7.5.1 Introduction.- 7.5.2 Determination of Carboxyl Groups by Nonaqueous Potentiometric Titration.- Instrumentation and Chemicals.- Standardization of Titrant.- Procedure for Carboxyl Group Determination.- Calculation.- 7.5.3 Discussion of Method.- References.- 7.6 Determination of Methoxyl Groups.- 7.6.1 Introduction.- 7.6.2 Sample Preparation.- 7.6.3 Determination of Methoxyl Content by the Vieboeck Schwappach Procedure.- 7.6.4 Discussion of Method.- References.- 7.7 Determination of Sulfonate Groups and Total Sulfur.- 7.7.1 Significance of the Analysis.- 7.7.2 Survey of Available Methods.- 7.7.3 Sulfonate Group Determination.- Principle of Conductometric Titration.- Description of Conductometric Titration of Pulp.- 7.7.4 Total Sulfur Determination.- Principle of Combustion/Ion Chromatography.- Description of Combustion/Ion Chromatography.- 7.7.5 Discussion of Methods.- References.- 8 Determination of Molecular Weight, Size, and Distribution.- 8.1 Gel Permeation Chromatography.- 8.1.1 Introduction.- Chromatography of Lignins on Sephadex Gels.- Modified Sephadex Gels.- 8.1.2 High-Performance Size Exclusion Chromatography (HPSEC).- 8.1.3 Experimental.- Equipment.- Sample Preparation.- Acetylation.- Methylation.- 8.1.4 Discussion of Method.- Problems Encountered in Gel Permeation Chromatography.- HPSEC on Styragel.- References.- 8.2 Light Scattering.- 8.2.1 Introduction.- 8.2.2 Principle.- Optical Anisotropy Correction.- Absorbance Correction.- Influence of Fluorescence.- 8.2.3 Method.- Instrument Description.- Procedure.- Solvents and Solutions.- Measurements.- Determination of Rayleigh Factors.- Specific Retractive Index Increment, dn/dc.- Data Processing.- 8.2.4 Discussion.- Clarification of Solvents and Solutions.- Influence of Fluorescence.- Influence of Anisotropy.- Typical Analytical Data.- Accuracy of the Method.- References.- 8.3 Vapor Pressure Osmometry.- 8.3.1 Introduction.- 8.3.2 Principle.- 8.3.3 Method.- Instrument Description.- Procedure.- Selection of Solvents.- Measurement Steps.- Evaluation of Results.- Calibration Factor.- Number-Average Molecular Weight.- 8.3.4 Discussion.- Drop Size Effects.- Response Time.- Purity of Solvents and Lignin.- Constancy of the Calibration Factor.- Typical Analytical Data.- References.- 8.4 Ultrafiltration.- 8.4.1 Introduction.- 8.4.2 Principle.- 8.4.3 Method.- UF Equipment and Membranes.- Preparation of Feed Solution.- Procedure.- Data Presentation.- 8.4.4 Discussion of Method.- References.- 9 Separation of Identification of Low-Molecular Weight Fragments and Model Compounds.- 9.1 Gas Chromatography-Mass Spectrometry (GC-MS).- 9.1.1 Introduction.- 9.1.2 Sample Preparation.- Extraction of Mixtures of Chemical Degradation Products.- Extraction of Spent Pulping Liquors and Bleaching Effluents.- Derivatization.- Preparation of Sample Solution.- 9.1.3 GC-MS Analysis.- Selection of Capillary Column for GC Analysis.- Selection of Optimum Conditions for GC Operation.- Selection of Most Suitable Mode for MS Operation.- GC-MS Operation.- Retrieval and Editing of Mass Spectral Data.- 9.1.4 Discussion of Method.- Validity of Structural Assignments.- Mass Spectra Quality.- Interpretation of Mass Spectra.- References.- 9.2 High Performance Liquid Chromatography (HPLC).- 9.2.1 Significance of the Analysis.- 9.2.2 Survey of Available Methods.- 9.2.3 Principle of the Preferred Method.- Adsorption Chromatography.- Reversed Phase Chromatography.- Chromatographic Theory.- 9.2.4 Description of the Preferred Method.- Mobile Phase and Pump Considerations.- HPLC Column: Attachment, Equilibration, and Performance Checks.- E/Z Monolignols - Separation and Calibration.- 9.2.5 Discussion of Methods.- Monomers.- Dimers.- Trimers and Higher Oligomers (Lignin Model Compounds).- References.
Series Title: Springer series in wood science.
Responsibility: edited by Stephen Y. Lin, Carlton W. Dence.


An up-to-date compilation of the theoretical background and practical procedures involved in lignin characterization. The advantages and limitations of individual methods are discussed and, more  Read more...


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