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The Institute of Paper Chemistry The Institute of Paper Chemistry Appleton, Wisconsin Doctor's Dissertation Determination of the Structure of the Black Spruce Glucomannan from the Molecular and Hydrodynamic Properties of its Triacetate Derivative William S. Linnell June, 1965 DETERMINATION OF THE STRUCTURE OF THE BLACK SPRUCE GLUCOMANNAN FROM THE MOLECULAR AND HYDRODYNAMIC PROPERTIES OF ITS TRIACETATE DERIVATIVE A thesis submitted by William S. Linnell B.A. 1960, Carleton College M.S. 1962, Lawrence College in partial fulfillment of the requirements of The Institute of Paper Chemistry for the degree of Doctor of Philosophy from Lawrence University, Appleton, Wisconsin Publication Rights Reserved by The Institute of Paper Chemistry June, 1965 TABLE OF CONTENTS Page SUMMARY 1 INTRODUCTION 3 ISOLATION OF GLUCOMANNAN POLYSACCHARIDES 6 Holocellulose Preparation 6 Extraction and Purification of the Glucomannan Fractions 6 Characterization of Holocellulose and Extracted Residue 7 ACETYLATION, FRACTIONATION, AND CHEMICAL CHARACTERIZATION OF THE MAIN GLUCOMANNAN 9 Chemical Nature of the Main Glucomannan Fractions 9 Acetylation 9 Solubility of the Glucomannan Triacetate 10 Fractionation of the Glucomannan Triacetate 11 Chemical Characterization of the Acetylated Glucomannan Fractions Obtained by Fractional Precipitation 11 Sugar Content 11 Lignin Content 14 ACETYLATION,.PURIFICATION, AND CHEMICAL CHARACTERIZATION OF VARIOUS ISOLATED GLUCOMANNANS AND GALACTOGLUCOMANNANS 15 General 15 Acetylation and Purification of the Various Glucomannans and Galactoglucomannans 15 Chemical Characterization of the Various Acetylated Glucomannans and Galactoglucomannans 16 Sugar Content 16 Infrared Spectra 18 Lignin Content 19 The Spectrum of the Mannose-Containing Polysaccharides of Black Spruce 19 CONFIGURATION OF THE GLUCOMANNAN DETERMINED FROM THE MOLECULAR AND HYDRODYNAMIC PROPERTIES OF THE MAIN ACETYLATED GLUCOMANNAN FRACTIONS 22 iii Molecular and Hydrodynamic Properties of the Main Acetylated Glucomannan Fractions 22 Configuration of the Glucomannan Determined from the Hydrodynamic Properties of Its Triacetate Derivative 25 Intrinsic Viscosity-Molecular Weight Relationship 25 Diffusion Coefficient and Sedimentation Coefficient Versus Molecular Weight Relationships 30 The Eizner-Ptitsyn Theory 33 Discussion 36 MOLECULAR PROPERTIES OF THE VARIOUS GLUCOMANNANS AND GALACTOGLUCOMANNANS 38 Degree of Polymerization in Relation to Resistance to Extraction from the Holocellulose 38 Molecular Properties of Various Acetylated Glucomannans and Galactoglucomannans 39 DISCUSSION OF THE LIGNIN-GLUCOMANNAN LINKAGE 42 Introduction 42 Indication of Lignin-Carbohydrate Linkage 42 Lignin in Relationship to Solubility and Molecular Size of the Glucomannan and Galactoglucomannan Fractions 44 Relationship of Lignin Content to Resistance to Extraction of Glucomannans and Galactoglucomannans 47 Relationship of Lignin Content to Sugar Content 49 DEGREE OF BRANCHING AND NATURE OF THE BRANCH POINTS 50 Possible Structures 50 Degree of Branching 53 The Structure of the Glucomannan Fractions and the Nature of the Branch Points 56 CONCLUSIONS 62 NOMENCLATURE 64 ACKNOWLEDGMENTS 68 LITERATURE CITED 69 ERRATA DETERMINATION OF THE STRUCTURE OF THE BLACK SPRUCE GLUCOMANNAN FROM THE MOLECULAR AND HYDRODYNAMIC PROPERTIES OF ITS TRIACETATE DERIVATIVE By WILLIAM S. LINNELL Page 27, third line from bottom: number or z-average..... Page 29, Fig. 2: Cellulose Trinitrate (199); Cellulose Acetate, DS = 2.3 (188); Cellulose in Cadoxen (194); Cellulose Acetate, DS 2.4 (201); Guaran Triacetate (21); Salep Glucomannan Triacetate (43); Branched Dextran (33) Page 57, next to last column heading should be n e --w Page 58, n instead of M . Page 61, last line: three instead of five. Page 91, 2nd paragraph, line 7: concentration instead of volume. Page 131, left portion of flow chart: Insol. IPyridine Insoluble Insol.' Page 133, under column heading Insol.-2, last no. in column - (1) - to be deleted. Page 143, paragraph 1, line 3: 1COO Page 178, 8th line from bottom of page: would be compensated. Page 187, Page 188, Page 188, Page 191, iv APPENDIX I. LITERATURE ON THE LIGNI-CARBOHYDRATE LINKAGE 80 APPENDIX II. HOLOCELLULOSE PREPARATION 88 APPENDIX III. EXTRACTION AND PURIFICATION OF THE GLUCOMANNAN FRACTIONS 92 APPENDIX IV. CHARACTERIZATION OF HOLOCELLULOSE AND EXTRACTED RESIDUE 105 APPENDIX V. ELECTROPHORESIS 112 APPENDIX VI. ACETYLATION OF THE MAIN GLUCOMANNAN FRACTIONS 114 APPENDIX VII. SOLUBILITY OF THE GLUCOMANNAN TRIACETATE 118 APPENDIX VIII. FRACTIONATION OF THE GLUCOMANNAN TRIACETATE 125 APPENDIX IX. QUALITATIVE SUGAR ANALYSIS OF THE ACETYLATED GLUCOMANNAN FRACTIONS OBTAINED BY FRACTIONAL PRECIPITATION 132 APPENDIX X. RESULTS OF THE ACETYLATION AND PURIFICATION OF VARIOUS GLUCOMANNANS AND GALACTOGLUCOMANNANS 136 APPENDIX XI. QUALITATIVE SUGAR CONTENTS OF THE VARIOUS ACETYLATED GLUCOMANNAN AND GALACTOGLUCOMANNAN FRACTIONS 140 APPENDIX XII. INFRARED SPECTRA 142 APPENDIX XIII. COMPARISON OF THE GLUCOMANNAN AND GALACTOGLUCOMANNAN FRACTIONS ISOLATED IN THIS INVESTIGATION WITH THE FRACTIONS ISOLATED BY THOMPSON (2) IN A QUANTITATIVE MATERIAL BALANCE OF BLACK SPRUCE HOLOCELLULOSE 149 APPENDIX XIV. PURIFICATION OF SOLVENTS 153 APPENDIX XV. OSMOMETRY 154 APPENDIX XVI. VISCOMETRY 159 APPENDIX XVII. LIGHT SCATTERING 164 APPENDIX XVIII. SEDIMENTATION EQUILIBRIUM 166 APPENDIX XIX. MOLECULAR WEIGHT HETEROGENEITY AND DISTRIBUTION 191 APPENDIX XX. DIFFUSION COEFFICIENTS 193 APPENDIX XXI. SEDIMENTATION COEFFICIENTS 203 APPENDIX XXII. COMPARISON OF HYDRODYNAMIC PROPERTIES OF VARIOUS POLYSACCHARIDES 205 v APPENDIX XXIII. RELATIVE SHAPE AND SIZE OF THE GLUCOMANNAN TRIACETATE MOLECULE 210 APPENDIX XXIV. THE EIZNER-PTITSYN THEORY 214 APPENDIX XXV. SECOND VIRIAL COEFFICIENT FROM OSMOMETRY 229 APPENDIX XXVI. VISCOSITY EXTRAPOLATION CONSTANTS 231 APPENDIX XXVII. VISCOSITIES IN CUPRIETHYLENEDIAMINE 237 APPENDIX XXVIII. ESTIMATION OF LIGNIN CONTENTS IN THE UNACETYLATED FRACTIONS 242 APPENDIX XXIX. POSSIBLE APPLICATIONS OF THE CROSS LINKED LIGNIN-CARBOHYDRATE MATRIX CONCEPT 243 SUMMARY Chemical evidence is presently available in the literature for and against the existence of branches other than the unit galactose side chains in softwood glucomannans; however, chemical methods will provide no information on the length of the branches. The goal of the present study is to determine if long-chain branching occurs in the glucomannan isolated from black spruce (Picea mariana) and to elucidate the extent and nature of possible branch points. A glucomannan was isolated from the 10% sodium hydroxide extract of a black spruce holocellulose prepared by a mild acidified sodium chlorite delignification at room temperature. The purified glucomannan was shown to be typical of conifer- ous glucomannans by quantitative sugar analysis, electrophoresis, and its infrared spectrum. The glucomannan was acetylated and carefully fractionated by fractional precipitation. The hydrodynamic and molecular properties of the acetylated frac- tions were determined by osmometry, viscometry, sedimentation equilibrium experi- ments, and analysis of the transient state during ultracentrifugation. Analysis of these properties according to existing polymer theories showed that the gluco- mannan had a relatively compact molecular configuration in comparison to linear D-1,4 linked polysaccharides and, therefore, definitely contained long-chain branches. Lignin was found to be tenaciously associated with glucomannan fractions which had been extensively purified and the hypothesis was made that lignin may be involved in the long-chain branching. A detailed inspection of the behavior of the glucomannan fractions in relationship to the lignin content, molecular properties, solubility properties, and ease of extraction from the holocellulose and a critical review of the literature indicated that lignin was quite probably chemically linked to the glucomannan chains. The results of this investigation were consistent with a model involving the cross-linking of essentially linear -2- glucomannan chains through common lignin moieties. This model adequately explained the fact that degrees of polymerization found in this study were higher than prev- iously reported in the literature for wood glucomannans and was consistent with the increase in the degree of branching with increasing degree of polymerization exhibited by the black spruce glucomannan fractions. The above hypothesis gained support from a theoretical treatment of the viscosity-molecular weight results in order to obtain a measure of the degree of branching. This treatment showed that the results were best described by a model involving cross-linking of linear chains. Using this model the number of cross- links per molecule increased from 0.1 for an essentially linear fraction with a weight average degree of polymerization (DP ) of 82 to a value of 7.1 for a highly branched fraction with DP equal to 557. The calculated degree of polymer- --w ization of the linear chains which are cross-linked together was constant within a narrow range for all fractions (with an average value of 77), regardless of the degree of polymerization of the entire cross-linked molecule. This constant value is good support for the validity of the crosslinked model which was employed. Extension of the results of this investigation to the original state of the glucomannan within the fiber indicates that the glucomannan and lignin are present in a cross-linked matrix containing at least occasional lignin-carbohydrate linkages. Supplementary investigations carried
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