The Chemistry of Lignin

The Chemistry of Lignin provides a critical review of the literature published from 1949 to 1958. This book provides information pertinent to the fundamental aspects of lignin chemistry.

Organized into 27 chapters, this book begins with an overview of the derivatives that are prepared for the characterization of the mother substance. This text then examines the various kinds of lignin and biosynthetic lignin-like products, which have been characterized by their behavior toward oxidation with nitrobenzene and alkali. Other chapters consider the morphological distribution of lignin in the wood fiber and the place of origin of lignin precursors and of the lignification process. This book discusses as well the formation or biosynthesis of lignin in plants and reviews the structure, isolation, and biosynthesis of lignin. The final chapter deals with producing lignin by the action of enzymes.

This book is a valuable resource for lignin chemists, scientists, research workers, and botanists.

I. Introduction

II. The Evolution of Lignin Chemistry

III. The Definition and Distribution of Lignin

IV. Color Reactions of Lignified Materials

A. Introduction

B. Color Reactions with Aliphatic Compounds

C. Color Reactions with Phenolic Compounds

D. Color Reactions with Aromatic Amines

E. Color Reactions with Heterocyelic Compounds

F. Color Reactions with Inorganic Reagents

G. Color Reactions with Dyestuffs

V. The Isolation of Lignin

A. Preparation of the Plant Material

B. Native Lignins

C. Insoluble Lignins

D. Organosolv Lignins

E. Lignins Extracted with Inorganic Reagents

F. Lignin Isolated by Hydrotropic Solvents

G. Lignin Isolated by a Mild Hydrogenation

H. Lignins Isolated from Barks

VI. The Determination of Lignin

A. Introduction

B. Direct Methods

C. Indirect Methods

D. Determination of Lignin in Spent Sulfite Liquor

E. Comparison of Lignin Determination Methods

F. Some Reported Lignin Contents

VII. The Physical Properties of Lignin

A. Introduction

B. Solubility

C. Melting Point

D. Heat of Combustion

E. Color

F. Density

G. Viscosity

H. Molecular Weight

I. Spreading Experiments

J. The Colloidal Nature of Lignin

K. The Electrophoresis of Lignin

L. X-Ray Investigations of Lignin

M. Refractive Index

N and O. Optical Activity and Fluorescence of Lignin

P. and Q. Ultraviolet and Infrared Absorption Spectra

VIII. The Elementary Composition and Constituent Groups of Lignin

A. Elementary Composition

B. The Phenylpropane Carbon Structure

C. Methoxyl Groups

D. Hydroxyl Groups

E. The Carbonyl Group

F. Carboxyl Groups

G. Double Bonds

IX. The Acylation and Acylysis of Lignin

X. The Alkylation of Lignin

XI. The Halogenation of Lignin

A. Fluorination

B. Chlorination

C. Bromination

D. Iodination

XII. The Nitration of Lignin

A. Introduction

B. The Action of Nitric Acid on Protolignin

C. Nitrolignins from Isolated Lignins

D. The Nitric Acid Pulping Process

XIII. The Sulfonation of Lignin

A. Introduction

B. The Sulfonation of Protolignin

C. The Sulfonation of Isolated Lignins

D. Reactions with Low-sulfonated Lignosulfonic Acids

E. The Effect of Phenolic Compounds on the Sulfonation of Lignin

F. The Sulfonation of Model Substances

G. Miscellaneous Research with Lignosulfonic Acid and Spent Sulfite Liquors

H. Theoretical Aspects of the Sulfonation of Lignin

XIV. The Hydrolysis of Lignin

A. In an Aqueous Neutral Solution

B. In an Alkaline Medium

C. Acid Hydrolysis

XV. The Alcoholysis of Lignin

A. Introduction

B. Alcohol Lignins

C. Polyalcohol Lignins

D. Alcoholysis to Monomolecular Lignin Building Stones

E. Theories on the Formation of Alcohol Lignin

XVI. The Mercaptolysis of Lignin

A. Introduction

B. Protolignin

C. Isolated Lignins

D. Reactions with Model Compounds

E. Conclusions

XVII. The Phenolysis of Lignin

XVIII. Reduction, Hydrogenation, and Hydrogenolysis of Lignin

XIX. The Oxidation of Lignin

A. Introduction

B. Oxidation in a Neutral Solution

C. In an Acid Medium

D. In an Alkaline Medium

XX. The Alkali Fusion of Lignin

XXI. Special Reactions with Lignin

A. The Condensation of Lignin with Halofatty Acids

B. The Condensation of Lignin with Maleic and Succinic Anhydride

C. The Condensation of Lignin with Methylene Iodide

D. The Condensation of Lignin with Acetylene

E. The Condensation of Lignin with Formaldehyde

F. The Condensation of Lignin with Dimethylamine, or Piperidine, and Formaldehyde

G. The Condensation of Lignin with Hexamethylenetetramine

H. The Condensation of Lignin with Thiourea

I. An Attempted Kolbe-Schmidt Reaction with Protolignin

J. The Action of Sodium in Liquid Ammonia on Lignin

K. The Effect of Irradiation on Lignin

L. The Effect of Gamma Radiation on Lignin

ΧΧII. The Thermal Decomposition of Lignin

XXIII. The Biological Decomposition of Lignin

A. Decomposition by Digestive Microörganisms (Metabolism of Lignin)

B. Decomposition by Soil Microörganisms

C. Decomposition by Wood-Destroying Fungi

XXIV. Theories on the Structure of Lignin

XXV. The Linkage of Lignin in the Plant

XXVI. The Biosynthesis of Lignin

A. Introduction

B. The Lignification Process

C. The Biosynthesis of Lignin Building Stones

D. The Biosynthesis of Ligninlike Products

E. Conclusions

XXVII. Synthetic Lignins

Appendix

A. Methods

B. Commercial Lignins

C. The Utilization of Lignin

Author Index

Subject Index