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The exothermic decompositions of the tosyl azide 1 and two diazides, 4,4'-diazidodiphenyl ether, (N3C6H4)2O 2 and 4,4'-diazidodiphenyl sulfide, (N3C6H4)2S (3), were studied theoretically using the CHETAH protocol, and experimentally using DSC, weight loss TGA-FTIR and C80-FTIR techniques. Numerical modelling and MS-spectroscopy were also performed to estimate the nature of the intrinsic molecular reactivity of the azides 1-3 as possible early stages of an oxidative self-heating process.
Rocznik
Tom
Strony
81--93
Opis fizyczny
Bibliogr. 24 poz.
Twórcy
autor
autor
autor
autor
autor
- Stazione Sperimentale per i Combustibili SSC, Viale A. De Gasperi 3, I-20097- San Donato M.se, Italy, paolo.zanirato@unibo.it
Bibliografia
- [1] Erase S., Gil C., Knepper K., Zimmermann V, Organic Azides: An Exploding Diversity of a Unique Class of Compounds, Angew. Chem. Int. Ed., 2005, 44, 5188-5240.
- [2] Azides and Nitrenes, Reactivity and Utility, (Scriven E.F.V., Ed.), Academic, Orlando 1984.
- [3] Bretherick's Handbook of Reactive Chemicals, 6th Ed, (Urben P.G., Ed.}, Butterworth/Heinemann, Oxford 1999.
- [4] Breslow D.S.; Industrial Applications, in: Azides and Nitrenes, Reactivity and Utility, (Scriven E.F.V. Ed.), Academic, Orlando 1984, p. 509-511.
- [5] The Chemistry oftheAzido Group, (Biffin M.E.C , Miller J., Paul D.B., Patai S., Eds.), Interscience, London 1971, pp. 61-63.
- [6] Spencer H., Explosion of p-toluene sulfonyl azide, Chem. Brit., 1981,17, 106.
- [7] Huynh V.M.-H., Hiskey M.A., Chavez D.E,, Naud D.L., Gilardi R.D., Synthesis, Characterization, and Energetic Properties of Diazido Heteroaromatic High-Nitrogen C-N Compounds, J. Am. Chem. Soc., 2005, 127, 12537-12543.
- [8] Haiges R., Boatz J.A., Vij A., Gerken M., Schneider S., Schroer T., Christie K.O., Polyazide Chemistry: Preparation and Characterization of Te(N3)4 and [P(C6H5)4]2[Te(N3)6] and Evidence for [N(CH3)4][Te(N3)5], Angew. Chem. Int. Ed., 2005, 42, 5847-5851.
- [9] Halevi E.A., Orbital Symmetry and Reaction Mechanism, Springer-Verlag Berlin 1992.
- [10] Rostovtsev V.V., Green L.G., Fokin V.V., Sharpless K.B., Bioconjugation by Copper(I)-Catalyzed Azide-Alkyne [3 + 2] Cycloaddition, Angew. Chem. Int. Ed,, 2002, 41, 2596-2599.
- [11] HahmaA,, Holmberg E., Hore N.,TrymanR., Wallin S., OestmarkH., Synthesis and characterization of phenylpentazoles, Int. Ann. Conf. ICT, (Energetic Materials 33rd), 2002, 62, 1-15.
- [12] Kotoyori T., Critical Temperatures for the Thermal Explosion of Chemicals, Elsevier, Amsterdam 2005.
- [13] Badders N.R., Wei C., Aldeeb A.A., Rogers W.J., Mannan M.S., Predicting the Impact Sensitivities of Polinitro Compounds Using Quantum Chemical Descriptors, J. Energ. Mat., 2006, 24, 17-33.
- [14] DoeringW. vonE.,DePuy C.H., Diazocyclopentadiene, J. Am. Chem. Soc., 1953, 75, 5955-5957.
- [15] Smith P.A.S., Hall J.H., Kinetic Evidence for the Formation of Azene (Electron-deficient Nitrogen) Intermediates from Aryl Azides, ibid, 1962, 84,480-485.
- [16] Minato M., Lahti P.M., Intramolecular Exchange Coupling of Arylnitrenes by Oxygen, J. Phys. Org. Chem., 1994, 4, 495-502.
- [17] FruripD.,WentonL.B., GoingJ.,HarisonB.K.,NiemierJ., Ural E.A., Intramolecular Exchange Coupling of Arylnitrenes by Oxygen, Process Safety Progress, 2004, 23,266-278.
- [18] Seaton W.H., Group Contribution Method for Predicting the potential of a Chemical Composition to Cause an Explosion (SAFETY), J. Chem. Ed., 1989, 66, A137- A147.
- [19] Tl is a Spartan 06 product based on Therrnochemical recipes of different quantum chemical methods that provide thermochemical data. In the present paper other energetics are obtained by functional density method (at B3LYP/6-31G* level) running with the Spartan 06 (www.wavefun.com), 2006.
- [20] Shanley E.S., Melhem G.A, A review of ASTM CHETAH 7.0 hazard evaluation criteria, J. Loss Prev. Process ind, 1995,8,261-264; The oxygen balance criterion for thermal hazards assessment, Process Safety Progress, 1995,14, 29-31.
- [21] Breslow D.S., Sloan M.F., Newburg N.M., Renfrew W.B., Thermal Reactions of Sulfonyl Azides, J. Chem. Soc., I960, 91, 2273-2279.
- [22] Campbell MM., Dunn A.D., Mass Spectra of Some Sulfonyl Azides, Org. Mass Spectr., 1972, 6, 599-600.
- [23] Abramovitch R.A., Kiba P., Scriven E.F.V., Mass Spectrometry of Aryl Azides, J. Org. Chem., 1971, 36, 3796-3803.
- [24] McLafferty F.W., Interpretation of the Mass Spectra, University Science Books, Mill Valley CA1980.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT1-0035-0050
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