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THERMOCHEMICAL INVESTIGATIONS of NITRORESORCINOLS and RELEVANT METAL SALTS a Thesis Submitted by JOHN ROLAND PAYNE in Candidatur

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THERMOCHEMICAL INVESTIGATIONS of NITRORESORCINOLS and RELEVANT METAL SALTS a Thesis Submitted by JOHN ROLAND PAYNE in Candidatur I I THERMOCHEMICAL INVESTIGATIONS OF NITRORESORCINOLS AND RELEVANT METAL SALTS A thesis submitted by JOHN ROLAND PAYNE in candidature for the degree of Doctor of Philosophy of the University of London. The Bourne Laboratory, (Department of Chemistry) Royal Holloway College, University of London, Egham Hill, Egham, February 1986. Surrey TW20 OEX ProQuest Number: 10097575 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 10097575 Published by ProQuest LLC(2016). 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 THERMOCHEMICAL INVESTIGATIONS OF NITRORESORCINOLS AND RELEVANT METAL SALTS. ABSTRACT The standard enthalpies of formation of 2,4-dihydroxy- 1.3.5-trinitrobenzene (styphnic acid), 2,4-dihydroxy- 3.5-dinitrobenzene (4,6-DNR), 2,4-dihydroxy-1,5- dinitrobenzene (2,4-DNR), 2,6-dinitrotoluene (two crystal forms) have been determined by oxygen static bomb calorimetry. An isoperibol solution reaction calorimeter has been constructed. By the determination of various enthalpies of reaction and solution, the enthalpies of formation of various synthesised polymorphs of lead styphnate, lead 2,4-dinitroresorcinol, and lead 4,6-dinitroresorcinol, thallous styphnate and barium styphnate were found. From these data, enthalpies of decomposition were calculated. By use of a group additivity scheme for solids, the enthalpies of form­ ation for a further five lead polynitroresorcinols was determined. The integral enthalpy of solution for lead nitrate was determined. A differential enthalpy of solution for lead nitrate was determined and an activity correction applied. The enthalpy of transition between the two crystal forms of 2.6-dinitrotoluene was determined and heat capacities of the respective forms in the solid and liquid phase measured. Powder X-ray crystallographic study of the two forms was made. TABLE OF CONTENTS Title-page.................................................. 1 Abstract..................................................... 2 Table of Contents................. 1..................... 3 List of Tables............................................. 15 List of Figures............................................ 18 Acknowledgements........................................... 20 Chapter I-Introduction Title-page.................................................. 22 I-AI: Historical background of Explosives.............. 23 I-AII: Explosive classifications......................... 24 Table I-l................................................... 25 I-AIII: Primary explosives............................... 26 I-AIV: Lead Styphnate..................................... 26 I-BI: Nitro Derivitives of Polyhydric Phenols.......... 27 I-BII: Preparation of Styphnic Acid..................... 28 I-BIII: Preparation of Dinitroresorcinols.............. 29 I-BIV: Properties of the Polynitroresorcinols........ 31 I-CI: Other metal salts of Polynitroresorcinols...... 32 I-CII: Priming Compositions.............................. 32 I-CIII: Uses................................................ 34 I-CIV: Industrial Purification of Lead Styphnate 35 I-CV: Metal Salts of Dinitroresorcinol................ 35 I-CVI: Structures.......................................... 35 I-DI: Nitrotoluenes........................................ 39 I-DII: Mononitrotoluene (MNT)............................ 39 I-DIII: Dinitrotoluene (DNT)............................. 40 Table 1 - 3 ................................................... 40 I-DIV: Historical background to Dinitrotoluene....... 40 I-DV: Uses................................................ 42 Table 1-2................................................. 43 I-EI: References......................................... 44 Chapter II- Purification of Raw Materials, and Preparations Title-page................................................ 47 II-A: Purification of Raw Materials................... 48 II-AI: Styphnic Acid.................................... 48 II-AII: Analysis......................................... 48 II-AIII; 2,4-Dinitroresorcinol......................... 48 II-AIV: Analysis......................................... 49 II-AV: 4 , 6-Dinitroresorcinol........................... 49 II-AVI: Analysis......................................... 49 II-AVII: 2, 6-Dinitrotoluene............................ 50 II-AVIII: Analysis....................................... 50 II-B: Preparations and Analysis........................ 51 II-BI: Preparation of Normal Lead Styphnate Monohydrate (a).................................. 51 II-BII: Analysis......................................... 51 II-BIII: Preparation of Monobasic Lead Styphnate (b). 51 II-BIV: Analysis......................................... 52 II-BV: Preparation of Tribasic Lead Styphnate (c).... 52 II-BVI: Analysis......................................... 52 II-BVII: Another Preparation of Tribasic Lead Styphnate (d).................................. 52 II-BVIII: Analysis....................................... 53 II-BIX; Preparation of Pentabasic Lead Styphnate (e). 53 II-BX: Analysis.......................................... 54 II-BXI: Preparation of Silver Styphnate (f)........... 54 II-BXII: Physical Properties........................... 54 II-BXIII; Analysis....................................... 55 Table II-l................................................ 55 II-BXIV: Preparation of Thallous Styphnate (g)....... 56 II-BXV: Analysis......................................... 56 II-BXVI; Another Preparation of Thallous Styphnate (h)............................................. 57 II-BXVII: Analysis....................................... 57 II-BXVIII: Preparation of Barium Styphnate Monohydrate (i)............................. 57 II-BXIX: Analysis........................................ 58 II-BXX: Preparation of Monobasic Lead 4,6- Dinitroresorcinol (j).......................... 59 II-BXXI: Analysis........................................ 59 II-BXXII: Preparation of Dibasic Lead 4,6- Dinitroresorcinol (k)........................ 60 II-BXXIII: Analysis..................................... 60 II-BXXIV: Preparation of Tribasic Lead 4,6- Dinitroresorcinol (1) ....................... 60 II-BXXV: Analysis........................................ 61 II-BXXVI: Preparation of Normal Lead 2,4- Dinitroresorcinol (m)........................ 61 II-BXXVII: Analysis...................................... 62 II-BXXVIII: Preparation of Monobasic Lead 2,4- Dinitroresorcinol (n)...................... 62 II-BXXIX: Analysis....................................... 63 II-BXXX: Preparation of Tribasic Lead 2,4- Dinitroresorcinol (o)......................... 63 II-BXXXI; Analysis....................................... 63 II-BXXXII: Preparation of Quadrabasic Lead 2,4- Dinitroresorcinol (p)....................... 64 II-BXXXIII: Analysis.................................... 64 II-BXXXIV: Micro-Analysis Results (Table II-2) ...... 65 II-BXXXV: References.................................... 66 Chapter III- Combustion Calorimetry Title-page................................................ 67 III-A: Combustion Calorimetry.......................... 68 Figure III-l............................................. 69 Figure III-2............................................. 70 III-B: Procedure......................................... 71 Figure III-3.............................................. 72 Figure III-4.............................................. 73 Figure III-5............................................. 74 III-C: Conditions ofExperimental Work................. 81 III-D: Combustion Experiments.......................... 82 III-E: Discussion......................................... 82 Table III-l................................................ 86 Table III-2................................................ 87 Table III-3................................................ 88 Table III-4................................................ 89 Table III-5............................................... 90 Table III-6............................................... 91 Table III-7............................................... 92 III-F: References......................................... 93 Chapter IV- Solution Calorimetry Title-page................................................ 94 IV-AI: Introduction...................................... 9 5 IV-AII: L.K.B. 8700-1 Precision Calorimetry System... 95 Figure IV-1............................................... 9 6 Figure IV-2............................................... 97 Figure IV-3............................................... 97 Figure IV-4.............................................. 98 Figure IV-5............................................... 98 IV-AIII: Dickinson's Method............................ 99 Figure IV-6............................................... 101 IV-AIV: Calculation Method used with L.K.B. 8700-1 Calorimeter..................................... 102 IV-AV: Calculation Method used with R.H.C./J.R.P. Calorimeter....................................... 102 IV-AVI: Twin-dewar Calorimeter System (R.H.C./J.R.P.) 103 IV-AVIa: Calorimeter
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