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A Study of Some Nitroso Compounds. Cilton Watson Tate Louisiana State University and Agricultural & Mechanical College

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A Study of Some Nitroso Compounds. Cilton Watson Tate Louisiana State University and Agricultural & Mechanical College Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1954 A Study of Some Nitroso Compounds. Cilton Watson Tate Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Part of the Chemistry Commons Recommended Citation Tate, Cilton Watson, "A Study of Some Nitroso Compounds." (1954). LSU Historical Dissertations and Theses. 8076. https://digitalcommons.lsu.edu/gradschool_disstheses/8076 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. A STUDY OF SOME MXTROSQ COMPOUNDS PART I * Oxidation of Nitroso Compounds to the corresponding Mitro Cosh pounds. PART IX - Development of Chromat©graphic and Spectrophotoiaetric Methods for the Separation, Identification and Estimation of some Mitros© and Related Compounds. PART XXX- Influences of Mitre Compounds on the Decomposition of Nitroso Compounds. A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy The Department o f Chemistry by C ilton Watson Tate M.S. Louisiana State University, 1950 Aug., 1953 UMI Number: DP69454 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. UMI Dissertation Publishing UMI DP69454 Published by ProQuest LLC (2015). Copyright in the Dissertation held by the Author. Microform Edition © ProQuest LLC. All rights reserved. This work is protected against unauthorized copying under Title 17, United States Code ProQuest ProQuest LLC. 789 East Eisenhower Parkway P.O. Box 1346 Ann Arbor, Ml 48106- 1346 MANUSCRIPT THESES Unpublished theses submitted for the master!s and doctor!s degrees and deposited in the Louisiana State University Library are available for inspection# Use of any thesis is limited by the rights of the author* Bibliographical references may be noted^ but passages may not be copied unless the author has given permission# Credit must be given in subsequent written or published work# A library which borrows this thesis for use by its clientele is expected to make sure that the borrower is aware of the above restrictions# LOUISIANA STATE UNIVERSITY LIBRARY 119-a 2- i S2P0 ACKNOWLEDGrMEWT The author wishes to express hie sincere appreciation to Or* W.R. Edwards, who directed this work for his aid and encouragement, and to Ore* A.R. Choppin and Joseph Reynolds fo r th e ir l& endiy suggestions* y He i s also indebted to Mr* Oct&vious Pasqual fo r his a ssista n ce , and to Mrs* John H* Tate for help in preparing the manuscript* The author wishes to express his appreciation to the Bureau of Ordnance, Department of the Maty and the Office of Ordnance Research, Department of the Amy, whose financial assistance made this work possible* i i ABSTRACTS Fart I - The objects of this part of the work wore (1) to study the effectiveness of hydrogen peroxide as an oxidant for th© conversion of n itro so eempouads i n general to n itr e compounds ( 2 ) to study the effects of possible variations in the conditions upon the progress of such oxidations. Previous work of th is s o rt has consisted o f a lim ite d number of isolated experiments, the reports of which gave little information suitable for the selection of optimum conditions ibr the reactions they described* Five aromatic nitroso compounds (four phenols mid one amine) were studied, with most attention being given to p-nitrosophenol, One aliphatic nitroso compound received similar study* It was found that hydrogen peroxide was generally satisfactory as an oxidant for the aromatiee studied, (presumably for aromatic nitroso compounds in general) and apparently su­ perior to other oxidants, as far as the latter have been examined* In the ease of the single aliphatic nitroso compound studied, hydrogen per­ oxide was found to be inferior to chromic acid* In the study of p-nitrosophenol, i t was observed that a maximum conversion to p-oitrophenol approaching 90$ could be attained* Extension of the time of exposure of reaction mixtures to hydrogen peroxide led in every case to a progressive loss of some of tbs nitre compound Initially formed. It was also observed that as the concentration of the peroxide, and/or the temperature was increased, the time required to reach the maximum yields was shortened* but within the ranges covered in this study, the amounts of such maximum yields did not vary greatly* Examination of the other aromatic nitroso compounds was less thorough* i l l but as far as it went* the results obtained were similar to those obtained with p-aitro* ophenol* When nitropropane wee oxidised with hydrogen peroxide, much smaller yields, ranging firm £ to 35SS. were obtained; the maximum yield being obtained only under narrow conditions of temperature and concentration* This compares with an 83$ possible yield when using chromic acid* P art U - The objects of thia part of the work were (l) to study the chromatographic and spectrophotometric characteristics of some selected n itr o , n itro so , amino, aso, and azoxy compounds; ( 2 ) to develop (and to study the effectiveness of) chromatographic and spectrophotometric pro* eedures for the identification, separation, and quantitative estimation of these compounds in solutions containing one or more of them* The re la tiv e rate s o f movement of these compounds on standard chromatographic columns were determined* By varying the adsorbents, the solvents, and the developing solutions, sufficient data were obtained to make possible the separations* For those compound* whioh gave a colorless seme, methods for locatlr^ the sons m the column were developed* The sensitivities, or the mini* sum ecncentrations necessary to give sones which could be discerned, were ascertained fo r sev eral o f them* Solutions o f known concentrations of the individual compounds in absolute ethyl alcohol were made up and the absorption curves of these solutions were obtained on a Beckman Model D.U. Quartz Spectrophotometer. Solutions of known concentrations of the individual compounds, and mixtures of two or more of the compounds, were made up in the proper sol­ vents, and separated on a chromatographic column* The zones, were cut out, dried, eluted, ml the solutions obtained diluted to the desired volume* The concentrations of these solutions were determined, using iv the Beckman Spectrophotometer and the standard curves which had been obtained as described* From the results obtained, it was concluded that ehromatographic and speetrophotcmetric techniques could be used as an efficient method lor the separation, partial identification, and estimation (with a range of error of approximately ^2%) of these compounds in mixtures* The objects o f th is work were (1) to s tudy the in te ra c tio n s, i f any, o f n itro confounds with n itro so compoundsi ( 2 ) to study any influences (exerted by interaction or otherwise) of nitro compounds upon the thermal and/or photochemical decomposition of nitroso compounds. The nitroso compounds studied in this part of the work were p-nitrosophenol and p-nitrosodimethyleniline. The nitro compounds used included nitrobcnsene, p*ehlor onitrobensene, p~nitrotoluene, p~nitro~ phenol and p-nitrobenaoie acid. In the ease of the amine i t was found that* there was some evidence of interaction, but that i t was usually small compared to the spontaneous decomposition of the n itro so compound. The extent o f the in te ra c tio n varied with conditions, being negligible or marly so under mild conditions, but more conspicuous under severe conditions of light or temperature. The oxidation of the nitroso compound to the analogous nitro compound, pre­ sumably by the oxidation action of the nitro compound in itially present, was observed in several instances but was at best small compared to other changes in the nitroso compound. When p^nitrosophenol was decomposed therm ally e r photoehemically in the presence of a nitro compound, i t responded in a manner which con* treated sharply with the behavior of the p-nitrosodimethylanillne. In the case of the phenol, the nitro compound exerted a decided inhibiting action upon such decomposition. This was studied in a variety of ways, v and while a complete end assured explanation of i t remains to be found, eons light has been shed on It by the present work* Indications are that the Inhibiting effect is not catalytic in nature, and that it is not to be ascribed to the absorption of ultra-violet radiations by the n itro compound. A p a r tia l and te n ta tiv e explanation of th is phenomena has been offered. v i TABLE OF CONTENTS Page PART I * OXIDATION OF NITROSO COMPOUNDS INTRODUCTION - 1 REVIEW OF THE LITERATURE -------------------------------- - $ EXPERIMENTAL------------------------------ 10 TABLES I TO I H ------------ IS FIGURES 1 TO S ------------------ 23 DISCUSSION OF RESULTS--------------------- 27 SUMMARY--------------------------- - ------------ 33 PART I I - DEVELOm.^T OF CHROMATOGRAPHIC AND SFECiROPHOaOMETRIC
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