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The Nitration and Fractionation of Whole Wood THE NITRATION AND FRACTIONATION OF WHOLE WOOD by WILMA ETHEL ELIAS B.A. (Hons.)* University of Saskatchewan, 1947 M.A., University of Saskatchewan, 1950 A THESIS SUBMITTED IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in the Department of Chemistry We accept this thesis as conforming to the required standard. THE UNIVERSITY OF BRITISH COLUMBIA October, 1956 In presenting this thesis in partial fulfilment of the requirements for an advanced degree at the University of British Columbia, I agree that the Library shall make it freely available for reference and study. I further agree that permission for extensive copying of this thesis for scholarly purposes may be granted by the Head of my Department or by his representative. It is under• stood that copying or publication of this thesis for financial gain shall not be allowed without my written permission. Department The. University of British Columbia, Vancouver &, .Canada. Faculty of Graduate Studies PROGRAMME OF THE FINAL ORAL EXAMINATION FOR THE DEGREE OF DOCTOR OF PHILOSOPHY of WILMA ETHEL ELI AS B.A. (Saskatchewan), 1947 M.A. (Saskatchewan), 19-50 MONDAY, OCTOBER 15th, 1956, 'at 11:30 "a.m. IN CHSMI'ST-RY LIBRARY COMMITTEE IN CHARGE DEAN G. M. SHRUM, Chairman DEAN F. H. SOWARD DR. L. D. HAYWARD ' PROF. H. ADASKIN DR. G. G. S. DUTTON Dii. W. A. BRYGE DR. C. A. MCDOWELL DEAN G. S. ALLEN External Examiner: PROFESSOR C. PURVES McGill University THE NITRATION AND FRACTIONATION OF WHOLE WOOD ABSTRACT In an attempt to develop a method by which the chemical components of whole wood samples could be separated on a quantitative basis, the reactions of gaseous dinitrogen pentoxide with model subtsances and with acetone-extracted wood have been studied. The crystalline compounds D-mannitol, benzoic acid and D,L-tartaric acid were smoothly nitrated by exposure to an excess of the pentoxide at 0 ± 2°C. and the crystalline products D-mannitol hexanitrate, D,L-tartaric acid dinitrate and /w-nitrobenzoic acid were recovered directly in quantitative yield. Good yields of the crystalline although somewhat less pure nitrates of D,L-mandelic acid, B-methyl-D-glucopyranoside and D-sorbitol were obtained in similar nitra• tions. D-Mannose, D-fructose, dulcitol, sucrose, maltose, lactose, cellobiose, vanillic acid, salicylic acid and vanillin gave poor yields of syrupy nitrated products. A beechwood xylan and holocellulose and lignin of western red cedar, isolated by conventional technics, were nitrated by the gaseous pentoxide method in yields and nitrogen contents comparable to those reported for other nitration methods. The xylan and holocellulose nitrates were incompletely soluble in acetone and the solubility of the nitrated lignin varied with the time of nitration. Optimum conditions were established for the nitration of acetone-extracted western red cedar heartwood. The weight ratio of nitrated wood : wood was closely reproducible and exceeded previously reported values; total nitrogen and ester nitrogen contents of the nitrated wood were reproducible within the experi• mental error of the determinations. The nitration reaction was not entirely quantitative since an average of 2.3% methoxyl was lost from the wood and the weight increase calculated from the total nitrogen content was, on the average, 3% lower than the observed value. Successive extraction with anhydrous acetone and methanol applied alter• nately, dissolved up to thirty-Eve percent of the nitro-wood and indicated that the nitration-solvent extraction technic should have value as a tool in the study of wood chemistry. GRADUATE STUDIES Field of Study: Chemistry Statistical Mechanics Dr. J. G. Hooley Stereochemistry Dr. L. D. Hayward Conjugated Systems and Aromatic Character ......Dr. G. G. S. Dutton Cellulose, Lignin and Related Compounds ; Dr. L. D. Hayward Organic Seminar Dr. G. G. S. Dutton Molecular Rearrangements - Dr. A. Rosenthal Other Studies: Wave Mechanics Dr. G. M. Volkoff Research in Wood Anatomy Mr. J. W. Wilson Seminar in Biochemistry Dr. S. Zbarsky Outside Interest: Music. Faculty of Graduate Studies 'PROGRAMME OF THE 'FINAL ORAL EXAMINATION -FOR THE DEGREE OF DOCTOR OF PHILOSOPHY of WILMA ETHEL ELI AS B.A. .(Saskatchewan), 1947 M.A. (Saskatchewan), 1950 MONDAY, 'OCTOBER 15th, '195.6, sat 11:30 .a.rn. TN CHEMISTRY LIBRARY r • COMMITTEE' IN CHARGE DSAN G. M... SHRUM, .Chairman DEAN • F.. H, ..SOWARD DR. L. D. HAYWARD 'PROF. H. ADASKIN . DR. • G. G. - S. DUTTON Da. -W. • A.. BRYCE DR.• C. A. MCDOWELL .DEAN.G. S.. ALLEN ^External' Examiner: '•;PR©FESSOR < C. >;PUR VES McGill University THE NITRATION AND FRACTIONATION OF WHOLE WOOD ABSTRACT In an attempt to develop a method by which the chemical components of whole wood samples could be separated on a quantitative basis, the reactions of gaseous dinitrogen pentoxide with model subtsances and with acetone-extracted wood have been studied. The crystalline compounds D-mannitol, benzoic acid and D,L-tartaric acid were smoothly nitrated by exposure to an excess of the pentoxide at 0 ± 2°C. and the crystalline products D-mannitol hexanitrate, D,L-tartaric acid dinitrate and w-nitrobenzoic acid were recovered directly in quantitative yield. Good yields of the crystalline although somewhat less pure nitrates of D,L-mandelic acid, B-methyl-D-glucopyranoside and D-sorbitol were obtained in similar nitra• tions. D-Mannose, D-fructose, dulcitol, sucrose, maltose, lactose, cellobiose, vanillic acid, salicylic acid and vanillin gave poor yields of syrupy nitrated products. A beechwood xylan and holocellulose and lignin of western red cedar, isolated by conventional technics, were nitrated by the gaseous pentoxide method in yields and nitrogen contents comparable to those reported for other nitration methods. The xylan and holocellulose nitrates were incompletely soluble in acetone and the solubility of the nitrated lignin varied with the time of nitration. Optimum conditions were established for the nitration of acetone-extracted western red cedar heartwood. The weight ratio of nitrated wood : wood was closely reproducible and exceeded previously reported values; total nitrogen and ester nitrogen contents of the nitrated wood were reproducible within the experi• mental error of the determinations. The nitration reaction was not entirely quantitative since an average of 2.3% methoxyl was lost from the wood and the weight increase calculated from the total nitrogen content was, on the average, 3% lower than the observed value. Successive extraction with anhydrous acetone and methanol applied alter• nately, dissolved up to thirty-five percent of the nitro-wood and indicated that the nitration-solvent extraction technic should have value as a tool in the study of wood chemistry. GRADUATE STUDIES Field of Study: Chemistry Statistical Mechanics Dr. J. G. Hooley Stereochemistry Dr. L. D. Hayward Conjugated Systems and Aromatic Ch¥racter::.:..;..::::...'Dr.-G. G. S. Dutton Cellulose, Lignin and Related Compounds..-. ........Dr. L. D. Hayward Organic Seminar Dr. G. G. S. Dutton Molecular Rearrangements ^D"r. A. Rosenthal Other Studies: Wave Mechanics Dr. G. M. Volkoff Research in Wood Anatomy Mr. J. W. Wilson Seminar in Biochemistry Dr. S. Zbarsky Outside Interest: Music. I ii ABSTRACT In an attempt to develop a method by which the chemical com• ponents of whole wood samples could be separated on a quantitative basis, the reactions of gaseous dinitrogen pentoxide with model sub• stances and with acetone-extracted wood have been studied. The crystalline compounds D-mannitol, benzoic acid and D,L- tartaric acid were smoothly nitrated by exposure to an excess of the pentoxide at 0 - 2° C. and the crystalline products D-mannitol hexanitrate, D,L-tartaric acid dinitrate and m-nitrobenzoic acid were recovered directly in quantitative yield. Good yields of the crystalline although somewhat less pure nitrates of D,L-mandelic acid, 8-methjd.-D-glucopyranoside and D-sorbitol were obtained in similar nitrations. D-Mannose, D-fructose, dulcitol, sucrose, maltose, lactose, cellobiose, vanillic acid, salicylic acid and vanillin gave poor yields of syrupy nitrated products. A beechwood xylan and holocellulose and lignin of western red cedar, isolated by conventional technics, were nitrated by the gaseous pentoxide method in ydlelds and nitrogen contents comparable to those reported for other nitration methods. The xylan and holocellulose nitrates were incompletely soluble in acetone and the solubility of the nitrated lignin varied with the time of nitration. Optimum conditions were established for the nitration of acetone- extracted western red cedar heartwood. The weight ratio vof nitrated wood : wood was closely reproducible and exceeded previously reported values; total nitrogen and ester nitrogen contents of the nitrated wood were reproducible within, the experimental error of the deter- iii minations. The nitration reaction was not entirely quantitative since an average of 2.5$ methoxyl was lost from the wood and the weight increase calculated from the total nitrogen content was, on the average, 5$ lower than the observed value. Successive extraction with anhydrous acetone and methanol applied alternately, dissolved up to thirty-five percent of the nitro-wood and indicated that the nitration-solvent extraction technic should hawe value as a tool in the study of wood chemistry. iv TABLE OF CONTENTS Page I. INTRODUCTION 1 II. HISTORICAL SURVEY .. .. 3 A. The Nitration Reaction 3 {l) Introduction 3 (2) The Mechanism of Nitration 4 (3) Nitrating Reagents 5 (4) Dinitrogen Pentoxide 6 (a) Preparation '.. 6 (b) Properties 9 (c) The Structure of Dinitrogen Pentoxide .. 10 B. The Scope and Limitations of the Nitration Reaction 11 (1) Miscellaneous Nitrating Reagents .. 11 (a) Nitryl Hal ides .. .. 11 (b) Other Reactions .. ... 12 (2) Mixtures of Nitric and Sulfuric Acids .. 12 (3) Acyl Nitrates 13 (4) Nitric Acid 15 (5) Mixtures of Nitric Acid with Acetic Acid and/or Anhydride 18 (6) Mixtures of Nitric Acid with Phosphoric Acid and Phosphoric Anhydride 22 (7) Dinitrogen Pentoxide 25 (a) Solutions of Dinitrogen Pentoxide in Polar Solvents .. 25 Page (b) Solutions of Dinitrogen Pentoxide in Inert Organic Solvents .'.
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