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Studies on the Synthesis of Chujramine and Hydrazine

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Studies on the Synthesis of Chujramine and Hydrazine STUDIES ON THE SYNTHESIS OF CHUJRAMINE AND HYDRAZINE DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Bussell Stephen Drago, B. S. The Ohio State University 195*+ Approved hy: Adviser Department of Chemistry i ACKNOWLEDGEMENT The author wishes to eaqpress his sincere appreciation to Dr. Harry H. Sisler for having accepted me as one of his students and for having proposed this problem. His able suggestions and continuing interest were a great aid to the progress of this work and his enthusiasm and pleasant disposition were an inspiration to the author. Thanks are due to many other members of the staff who have in one way or another contributed to the accomplishment of this research. Special thanks are due to Dr. T. Rubin and Dr. J. Calvert for their suggestions concerning the calculations of the thermodynamic quantities. The author acknowledges with gratitude the fact that the Davison Chemical Company has, through a contract with the Ohio State University Research Foundation, given generous support to the research reported in this dissertation. The author is greatly indebted to his wife, Ruth Ann, both for typing this dissertation and for her continuous support and encouragement • ii TABUS OF CONTESTS Page Introduction 1 Chapter I Historical A. Chloramine Synthesis: the Beactlon of Chlorine with Ammonia 3 B. The Baschig Synthesis for Hydrazine 6 C. The Synthesis of Hydrazine in Liquid Ammonia 1 1 D. Preparation and Properties of Anhydrous 13 Hydrazine Chapter II The Synthesis of Chloramine 20 A. Introduction 20 B. Experimental 20 1. Materials 20 2. Experimental Procedure 21 C. Besults 2U 1. Initial Buns 2^ 2. Investigations with a New Ammonia Inlet 25 3. Corrected Flow Calculations 28 Investigations to Test the Flow Bate Theory 32 D. Conclusions 3^ Chapter III The Bole of Caustic, Gelatin and Ammonium Ion in the Aqueous Chloramine-Ammonia Beactlon 37 A. Introduction 37 B. Experimental 33 1. Materials 38 2. Experimental Procedure 38 iii C. Be suits l+o 1 . The Bole of Caustic k 0 2. The Effect of Anmanium Chloride 52 3. The Effect of Gelatin 5 ^ D. Conclusions 5L Chapter XV The Effect of Fixed Baseand Gelatin on the 57 Chloramine-Ammonia Beactlon in Liquid Ammonia and in Ethyl Alcohol A. Introduction 57 B. Experimental 57 1. Materials 57 2. Experimental Procedure 57 C. Besuits 58 Chapter V The Separation of Anhydrous Hydrazine from Ammonium Chloride-Ammonia-Hydrazine Mixtures 6 l A. Introduction 6 l B. Experimental 6 l 1. Materials and Equipment 6 l 2. Experimental Procedure 63 C. Besults 70 1. Preliminary Experimente 70 2. Liquid Composition-Vapor Composition Data 72 Obtained vlth the Sodium Hydroxide Coated Apparatus 3. Liquid Composition-Vapor Composition Data 73 Obtained vith the Teflon Coated Apparatus D. Conclusions 75 iV g&sa Chapter VI Vapor Pressure-Composition Studies on 76 the System Ammonia-Hydrazine at Elevated Temperatures A. Introduction. 76 B. Experimental 76 1. Materials 76 2. Experimental Procedure 76 C. Besuits and Thermodynamic Calculations 87 1. Results 87 2. Thermodynamic Calculations 97 D. Conclusions 119 Chapter VII Summary 120 Bibliography 123 Autobiography 126 STUDIES ON THE SYNTHESIS OF CHLORAMINE ANT HYDRAZINE Introduction^- The application of hydrazine both as a rocket propellant and as a versatile raw material for the synthesis of other hydronitrogen compounds has given rise to a considerable amount of research on the synthesis, application and physical properties of this Bubstance. There is a tremendous amount of patent literature concerning application of hydrazine but its actual industrial use has been limited by the present high cost of the material. A more economical process for the synthesis of hydrazine would undoubtedly bring about an increase in the utiliza­ tion of this compound. At present, hydrazine is produced commercially by methods which 2 entail slight modifications of the original Raschig process. In all instances the reaction is carried out in an aqueous solution and the very stable hydrazine hydrate is obtained as the product. An additional expense is encountered when anhydrous hydrazine is desired because it is necessary to distill the hydrate with barium oxide or caustic, or apply some similarly expensive process to remove the water. The current high cost of hydrazine indicates that this synthesis is an expensive chemical process. 3 Mattair and Sisler were the first to report the synthesis of hydrazine in liquid ammonia by the reaction of chloramine and anhydrous ammonia. Chloramine, the Raschig synthesis intermediate, is produced in the Sisler-Mattair process by the gas phase reaction of chlorine and anhydrous ammonia. Since ammonia does not form a stable solvate with hydrazine it was hoped that this synthesis might be developed into an economical process for producing anhydrous hydrazine. Further k 5 studies have been carried out in this laboratory by Boatman , Neth , 6 7 8 Hurley , She liman , and Kelmers . These investigations have been extended in the present study and the results will be presented in this dissertation. Conditions leading to almost quantitative yields of chloramine by the gas phase reaction of ammonia and chlorine have been discovered. The possibility of obtaining anhydrous hydrazine from the chloramine-ammonia reaction mixture by a high pressure distillation has been qualitatively demonstrated. The partial pressures of hydrazine and ammonia in equilibrium with various liquid mixtures of these two substances have been measured at several elevated temperatures. Activities of the components have been calculated for this system. The effects of the Baechig synthesis additives on the hydrazine-forming reaction between chloramine and ammonia have been studied in water, liquid ammonia and alcohol. A discussion of these topics is presented in this dissertation. 3 Chapter I Historical A. CSLORAMHig SYNTHESIS: THE REACTION OF CHLORINE WITH AMMONIA The earliest observations on the reaction of ammonia and chlorine 9 10 were reported by Simon , Donny, and Mareska , Simon noted that explosions occur when chlorine gae 1b bubbled through concentrated eolutione of aqueous ammonia. When ammonia is present in excess of okve the chlorine the products formed/\nitrogen and ammonium chloride. When an excess of chlorine is reacted with either aqueous ammonia or an aqueous solution of an ammonium salt, nitrogen trichloride is 10 formed. Explosions also occur when gaseous ammonia is bubbled into 11 liquid chlorine. Valentin! reported that ammonia gas burns in chlorine gas when mixed at ordinary temperatures. The reaction is described by the equation: 8NH3+ 3C12---> 61111*0 1 + N2 (1) 12 These results were later confirmed by Schwarz and Striebich . 13 Selivanoff reported that the stoichiometry for the reaction of aqueous ammonia with an excess of chlorine is represented by the equation: *+WH3 3C12 -— » NCI3+ 3NH^C1 (2) 1^ This reaction was studied in more detail by Noyes and Iyon , who arrived at the following equation for the reaction in aqueous solution from a quantitative study of the products and reactants: 12NH3 + 6 CI2 --- *N2 + NCI3 + 9NHjjCl (3) These studies vere performed at an ammonia to chlorine mole ratio of two to one. Bray and Dowell postulated a mechanism for the ammonia-chlorine reaction In aqueouB solution Based on the formation of chloramine as an Intermediate. They stated that chloramine behaves as the intermediate in the formation of nitrogen from the reaction in basic solution, and also as the intermediate in the formation of nitrogen trichloride in acid solution. Theee reactions were represented as proceeding according to the following equations: 6NH3 + 6 CI2 ) 6nh2ci + 6HC1 ( M 3MH2 C 1 * Ng +N H 4 CI+ 2HC1 (5) 3NH2 C1 + NH^Cl --- > 3NH3 + NC13 + HC1 (6 ) Reaction (k), the very rapid primary reaction, is followed almost quantitatively by reactions (5) or (6) or both, depending upon conditions. Noyee accepted thiB mechanism and pointed out that the summation of reactions (10, (5)> and (6) results in the equation: 3NH3 + 6 CI2 ---» N2 + NC13 + 9HC1 lU which is similar to reaction (3 ) that he had reported. Dowell and Bray ^ reported the following reaction between nitrogen trichloride and aqueous ammonia: 1«H3+ NC1 3 --- > N2 + 3WH^C1 (7) Combination of this equation with (3) yields: 8MH-+ 3 CI3 ---> 6 NHkCl+ N2 5 11 which is equation (l) reported by Valentini for the complete oxidation of ammonia in the gas phase. 17 Noyes and Haw studied the reaction between chlorine and ammonia in the gas phase, as well as in carbon tetrachloride, chloroform and pentane solutions. In these experiments mole ratios ranging from 1.5 up to 5 moles of ammonia to 4 moles of chlorine were employed. They represented the reaction in these concentration ranges by the equation: Unh3 + 3C12 --- > MH^Cl + NCl^ (8) Chloramine and dlchloraaine were postulated as intermediate products. These authors also found that chloramine and dichloramine are produced in the reaction of chlorine with ammonium salts. O The synthesis of chloramine was first reported by Raschig . ^.ualitative tests indicated that chloramine is formed from the reaction of equimolar quantities of aqueous ammonia and sodium hypochlorite. Several reactions which chloramine undergoes are reported in this reference. 1.8 Markwald and Wille report the preparation and isolation of chloramine. The pure material was prepared by drawing the vapors from an aqueous solution of sodium hypochlorite and ammonia through anhydrous potassium hydroxide at water aspirator pressures. A substance was o ° obtained which upon removal of ammonia at -70 C solidified at -60 C, sometimes to a crystalline form and other times to a glass. The Q substance exploded at -50 C forming nitrogen, chlorine and ammonium chloride. The material was analyzed by dissolving it in ethyl alcohol and determining the nitrogen and chlorine content. The analysis con­ firmed the presence of chloramine. 3 Sislor and Mattair prepared chloramine by the gas phase reaction of chlorine and ammonia.
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