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Novel 1,3-dipolar cycloadditions of dinitraminic acid: Implications for the chemical stability of ammonium dinitramide
KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Fysikalisk kemi.ORCID-id: 0000-0003-2673-075X
2008 (engelsk)Inngår i: Journal of Physical Chemistry A, ISSN 1089-5639, E-ISSN 1520-5215, Vol. 112, nr 11, s. 2456-2463Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Density functional theory at the B3LYP/6-31+G(d,p) level and ab initio calculations at the CBS-QB3 level have been used to analyze 1,3 dipolar cycloaddition reactions of dinitraminic acid (HDN) and its proton transfer isomer (HO(O)NNNO2). It is shown that the nitro group of HDN and the -N-N = O functionality of the isomer react readily with carbon-carbon double bonds. Cycloadditions of HDN are compared with the corresponding reactions with azides and nitrile oxides as 1,3 dipoles. It is shown that the reactivities of HDN and its proton transfer isomer decrease with increasing electron withdrawing power of the substituents adjacent to the carbon-carbon double bond. In contrast, for azides and nitrile oxides, the highest reactivity is obtained with dipolarophiles with strongly electron withdrawing substituents. The observed reactivity trends allow for the design of unsaturated compounds that are highly reactive toward azides and chemically inert toward dinitramides. This may be of relevance for the development of binder materials for ammonium dinitramide based propellants.

sted, utgiver, år, opplag, sider
2008. Vol. 112, nr 11, s. 2456-2463
Identifikatorer
URN: urn:nbn:se:kth:diva-17373DOI: 10.1021/jp710559gISI: 000253946100035Scopus ID: 2-s2.0-46849106047OAI: oai:DiVA.org:kth-17373DiVA, id: diva2:335417
Merknad
QC 20100525Tilgjengelig fra: 2010-08-05 Laget: 2010-08-05 Sist oppdatert: 2017-12-12bibliografisk kontrollert
Inngår i avhandling
1. Green Propellants
Åpne denne publikasjonen i ny fane eller vindu >>Green Propellants
2010 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

To enable future environmentally friendly access to space by means of solid rocket propulsion a viable replacement to the hazardous ammonium perchlorate oxidizer is needed. Ammonium dinitramide (ADN) is one of few such compounds currently known. Unfortunately compatibility issues with many polymer binder systems and unexplained solid-state behavior have thus far hampered the development of ADN-based propellants.

Chapters one, two and three offer a general introduction to the thesis, and into relevant aspects of quantum chemistry and polymer chemistry.

Chapter four of this thesis presents extensive quantum chemical and spectroscopic studies that explain much of ADN’s anomalous reactivity, solid-state behavior and thermal stability. Polarization of surface dinitramide anions has been identified as the main reason for the decreased stability of solid ADN, and theoretical models have been developed to explain and predict the solid-state stability of general dinitramide salts. Experimental decomposition characteristics for ADN, such as activation energy and decomposition products, have been explained for different physical conditions. The reactivity of ADN towards many chemical groups is explained by ammonium-mediated conjugate addition reactions. It is predicted that ADN can be stabilized by changing the surface chemistry with additives, for example by using hydrogen bond donors, and by trapping radical intermediates using suitable amine-functionalities.

Chapter five presents several conceptual green energetic materials (GEMs), including different pentazolate derivatives, which have been subjected to thorough theoretical studies. One of these, trinitramide (TNA), has been synthesized and characterized by vibrational and nuclear magnetic resonance spectroscopy.

Finally, chapter six covers the synthesis of several polymeric materials based on polyoxetanes, which have been tested for compatibility with ADN. Successful formation of polymer matrices based on the ADN-compatible polyglycidyl azide polymer (GAP) has been demonstrated using a novel type of macromolecular curing agent. In light of these results further work towards ADN-propellants is strongly encouraged.

sted, utgiver, år, opplag, sider
Stockholm: KTH, 2010. s. 77
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2010:43
Emneord
Quantum chemistry, reaction kinetics, ammonium dinitramide, high energy density materials, rocket propellants, chemical spectroscopy, polymer synthesis
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-25835 (URN)978-91-7415-758-1 (ISBN)
Disputas
2010-11-23, F1, Lindstedtsvägen 22, KTH, Stockholm, 09:30 (engelsk)
Opponent
Veileder
Merknad
QC 20101103Tilgjengelig fra: 2010-11-03 Laget: 2010-11-02 Sist oppdatert: 2011-03-21bibliografisk kontrollert

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