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Studies on Lignins of Woods and Jute PDF

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r FORDHAM UNIVERSITY GRADUATE SCHOOL 19.51. This dissertation prepared under my direction by Stanley F. Kudzin entitled STUDIES ON LIGNINS OF WOODS AND JUTE has been accepted in partial fulfilment of the requirements for the Degree of Doctor of Philo sophy Dr...F,F....Nqrd..... (Faculty Adviser) STUDIES ON DIGNINS OF WOODS AND JUTE BY STANDBY F* KUDZIN B#S*f F©r&liam G©llegef 1947 M*S*, FordJaam University, 1949 DISSERTATION SUBMITTED IN PART I AD FUDFIDDMENT OF THE REQUIRE­ MENTS FOR THE DEGREE OF DOG TOR OF PHIDOSOPHY IN THE DEPARTMENT OF 0HE1ISTRY AT FORDHAM UNIVERSITY NEW YORK ProQuest Number: 10993000 All rights reserved INFORMATION TO ALL USERS The quality of this reproduction is dependent upon the quality of the copy submitted. In the unlikely event that the author did not send a complete manuscript and there are missing pages, these will be noted. Also, if material had to be removed, a note will indicate the deletion. uest ProQuest 10993000 Published by ProQuest LLC(2018). Copyright of the Dissertation is held by the Author. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code Microform Edition © ProQuest LLC. ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106- 1346 ii r TABLE OF CONTENTS i Page LIST OP TABLES .............. ♦ . iv LIST OP FIGURES ..................................... v ACKNOWLEDGEMENTS ............................. .. ♦ vii I. INTRODUCTION *............................... 1 II* EXPERIMENTAL METHODS ........ 6 A. Microbiological •••••........ 6 B. Analytical • • 8 G. Preparative ••••.... .............. 11 B* Spectroscopic 13 III. EXPERIMENTAL RESULTS ........................ 14 A. Studies on Softwood Lignin ••....••••••...•• 14 1. Infrared Absorption Speotra «••••••••••••• 15 2. Methylation with Biazomethane 18 3. Oxidation with Alkali and Nitrobenzene .. . 21 B. Studies on Hardwood Native Lignins ........ 23 1. Elementary and Methoxyl Analyses of Native Lignins....•••.••••••••••••••.« 25 2. Ultraviolet Absorption Speetra .... 27 3. Solubilities and Color Reactions ••••••••• 30 4* Acetate and Phenylhydrazone Derivatives .. 33 5. Maule Test and Oxidation with Alkali and Nitrobenzene ..*••••.••••••••••••••••••• 37 6. Infrared Absorption Spectra ..•••.•••••••• 39 7* Methylation with Diazomethane ••••••..,••• 41 8. Infrared Absorption Spectra of Methylated Lignins *......... 45 iii r Page ^ C. Studies on Enzymatically liberated Hardwood Lignins .... 47 1* Comparison of Native and Enzymatically Liberated Lignins ..................... 51 D. Studies on Jute Lignin ••.••.•••.•••••••••* 63 it; discussion... ......... 66 Y. SUMMARY ...... ........ 72 REFERENCES . . ...... 74 iV r LIS! OP CABLES 'I I ABLE Page I. Methylation with Biazomethane of White Scots Pine Lignins ........... ....•• 19 II. Oxidation of White Scots Pine Lignins with Alkali and Nitrobenzene ............. 22 III* Analysis of Sulfuric Acid Lignins •..•••.•••• 24 IV. Analysis of Native Lignins •.••«••••..••••*. • 26 V. Solubilities, Reducing Abilities and Color Reactions of Native Lignins ♦•«.••••••••••» 31 VI. Sulfuric Acid Lignins Obtained from Native Hardwood Lignins ...... 32 VII. Acetate and Phenylhydrazone Derivatives of Native Lignins ....... 34 VIII. Oxidation of Native Hardwood Lignins ••••..•* 38 IX. Comparison of Calculated and Pound Methoxyl Contents of Derivatives of Hardwood Native Lignins ........................... 43 X. Methylation of Native Lignins with Diazome- thane ..................................... 44 XI. Effect of the Action of Daedalea quercina on the Composition of Oak, Birch and Maple ... 48 XII. Yields of Lignin Isolated from Sound and Decayed Hardwoods 30 XIII. Comparison of Native and Enzymatically Libe­ rated Hardwood Lignins .... 53 XIV. Effect of Trichoderma viride and of Penicil- lium citrinum on the Composition ofJute S*ibre «... ..7. * * 65 L LIST OF FIGURES FIGURE I* Standard Curves for the Spectrophotometrie Determination of Vanillin and Syringalde- hyde ...... .••••••••..*••« II. Infrared Absorption Spectra of Native and Enzymatically liberated White Scots Pine ' lignins .. III. Infrared Absorption Spectra of the Diazome- thane-Methylated White Scots Pine lignins .. IV. Ultraviolet Absorption Spectra of Oak, Birch, Maple, White Scots Pine and Aspen Native lignins .•«. V. Ultraviolet Absorption Spectra of the Phenyl- hydrazones of Oak, Birch, Maple and White Pine Native lignins .. ....... VI. Ultraviolet Absorption Spectra of the Acetates of Oak, Birch, Maple and White Scots Pine Native Iignms ............................. VII. Infrared Absorption Spectra of Oak, Birch, Maple and White Scots Pine Native lignins .. VIII. Infrared, Absorption Spectra of Diazomethaner Methylated Oak, Birch and Maple Native lignins ..• IX. Ultraviolet Absorption Spectra of Native and Enzymatically liberated Oak, Birch and Maple X. Ultraviolet Absorption Spectra of the Acetates of Native and Enzymatically liberated. Oak,„ Birch and Maple lignins XI. Ultraviolet Absorption Spectra of the Phenyl- hydrazones of.Native and Enzymatically libe­ rated Oak, Birch and Maple lignins ••••••••• / XII. Infrared Absorption Spectra of Native and En­ zymatically liberated Oak lignins •••••••••. XIII. Infrared Absorption Spectra of Native and En­ zymatically liberated Birch lignins ..... vi r FIGURES Page n XIV# Infrared Absorption Spectra of Native and En­ zymatically Liberated Maple Lignins #•##••## 59 XV# Infrared Absorption Spectra of the Diazometha- ne-Methylated Native and Enzymatically Li­ berated Oak Lignins ..... • 60 XVI# Infrared Absorption Spectra of the Diazome- thane-Methylated Native and Enzymatically Liberated Birch Lignins 61 XVII. Infrared Absorption Spectra of the Diazome- thane-Methylated Native and Enzymatically Liberated Maple Lignins # • # . . « . # • 6 2 L _i vii r m ACK3J0WLEIXxMEM?S This dissertation is dedicated t© my mother and father* These investigations were assisted hy a grant from the Office of Uaval Research, and were earried out under the direction ©f Dr* f*P* lord* L

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