Studies on Energetic Salts Based on (2,4,6‐Trinitrophenyl)guanidine
Identifieur interne : 000D39 ( Istex/Corpus ); précédent : 000D38; suivant : 000D40Studies on Energetic Salts Based on (2,4,6‐Trinitrophenyl)guanidine
Auteurs : Thomas M. Klapötke ; Frank Mieskes ; Jörg Stierstorfer ; Michael WeyrautherSource :
- Propellants, Explosives, Pyrotechnics [ 0721-3115 ] ; 2016-04.
Abstract
(2,4,6‐Trinitrophenyl)guanidine was synthesized and its thermal and energetic properties were investigated. The reaction of (2,4,6‐trinitrophenyl)guanidine with different acids, such as nitric, picric, perchloric, and hydrochloric acid results in protonation of (2,4,6‐trinitrophenyl)guanidine and the formation of the corresponding salts (cation : anion ratio 1 : 1). The reactions are performed at ambient temperature in H2O or EtOH and produce qualitatively pure products with energetic properties, which are typical of those of secondary explosives. The compounds were characterized using multinuclear NMR spectroscopy, IR and Raman spectroscopy, as well as mass spectrometry. Single crystal X‐ray diffraction studies were performed and the structures of the four different salts at low temperatures were determined. The thermal stabilities were measured using differential scanning calorimetry (DSC). The sensitivities were determined using the BAM drophammer and friction tests. The heats of formation were calculated by the atomization method based on CBS‐4M enthalpies. Using these values as well as the X‐ray or pycnometric densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code.
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DOI: 10.1002/prep.201500338
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Klapötke</name><affiliation><mods:affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</mods:affiliation></affiliation><affiliation><mods:affiliation>E-mail: tmk@cup.uni‐muenchen.de</mods:affiliation></affiliation><affiliation><mods:affiliation>Correspondence address: Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</mods:affiliation></affiliation></author><author><name sortKey="Mieskes, Frank" sort="Mieskes, Frank" uniqKey="Mieskes F" first="Frank" last="Mieskes">Frank Mieskes</name><affiliation><mods:affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</mods:affiliation></affiliation></author><author><name sortKey="Stierstorfer, Jorg" sort="Stierstorfer, Jorg" uniqKey="Stierstorfer J" first="Jörg" last="Stierstorfer">Jörg Stierstorfer</name><affiliation><mods:affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</mods:affiliation></affiliation></author><author><name sortKey="Weyrauther, Michael" sort="Weyrauther, Michael" uniqKey="Weyrauther M" first="Michael" last="Weyrauther">Michael Weyrauther</name><affiliation><mods:affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</mods:affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Propellants, Explosives, Pyrotechnics</title><title level="j" type="alt">PROPELLANTS, EXPLOSIVES, PYROTECHNICS</title><idno type="ISSN">0721-3115</idno><idno type="eISSN">1521-4087</idno><imprint><biblScope unit="vol">41</biblScope><biblScope unit="issue">2</biblScope><biblScope unit="page" from="217">217</biblScope><biblScope unit="page" to="222">222</biblScope><biblScope unit="page-count">6</biblScope><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2016-04">2016-04</date></imprint><idno type="ISSN">0721-3115</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0721-3115</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">(2,4,6‐Trinitrophenyl)guanidine was synthesized and its thermal and energetic properties were investigated. The reaction of (2,4,6‐trinitrophenyl)guanidine with different acids, such as nitric, picric, perchloric, and hydrochloric acid results in protonation of (2,4,6‐trinitrophenyl)guanidine and the formation of the corresponding salts (cation : anion ratio 1 : 1). The reactions are performed at ambient temperature in H2O or EtOH and produce qualitatively pure products with energetic properties, which are typical of those of secondary explosives. The compounds were characterized using multinuclear NMR spectroscopy, IR and Raman spectroscopy, as well as mass spectrometry. Single crystal X‐ray diffraction studies were performed and the structures of the four different salts at low temperatures were determined. The thermal stabilities were measured using differential scanning calorimetry (DSC). The sensitivities were determined using the BAM drophammer and friction tests. The heats of formation were calculated by the atomization method based on CBS‐4M enthalpies. Using these values as well as the X‐ray or pycnometric densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code.</div></front></TEI><istex><corpusName>wiley</corpusName><author><json:item><name>Thomas M. 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Such materials are peer reviewed and may be re‐organized for online delivery, but are not copy‐edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
</p><supportingInfoItem><mediaResource alt="supporting information" href="urn-x:wiley:07213115:media:prep201500338:prep_201500338_sm_miscellaneous_information"></mediaResource><caption>miscellaneous_information</caption></supportingInfoItem></supportingInformation><abstractGroup><abstract type="main" xml:lang="en"><title type="main">Abstract</title><p>(2,4,6‐Trinitrophenyl)guanidine was synthesized and its thermal and energetic properties were investigated. The reaction of (2,4,6‐trinitrophenyl)guanidine with different acids, such as nitric, picric, perchloric, and hydrochloric acid results in protonation of (2,4,6‐trinitrophenyl)guanidine and the formation of the corresponding salts (cation : anion ratio 1 : 1). The reactions are performed at ambient temperature in H<sub>2</sub>O or EtOH and produce qualitatively pure products with energetic properties, which are typical of those of secondary explosives. The compounds were characterized using multinuclear NMR spectroscopy, IR and Raman spectroscopy, as well as mass spectrometry. Single crystal X‐ray diffraction studies were performed and the structures of the four different salts at low temperatures were determined. The thermal stabilities were measured using differential scanning calorimetry (DSC). The sensitivities were determined using the BAM drophammer and friction tests. The heats of formation were calculated by the atomization method based on CBS‐4M enthalpies. Using these values as well as the X‐ray or pycnometric densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code.</p></abstract><abstract type="graphical" xml:lang="en"><p><blockFixed type="graphic"><mediaResourceGroup><mediaResource alt="image" href="urn:x-wiley:07213115:media:PREP201500338:content" eRights="yes" copyright="WILEY-VCH"></mediaResource></mediaResourceGroup></blockFixed></p></abstract></abstractGroup></contentMeta></header></component></istex:document></istex:metadataXml><mods version="3.6"><titleInfo lang="en"><title>Studies on Energetic Salts Based on (2,4,6‐Trinitrophenyl)guanidine</title></titleInfo><titleInfo type="alternative" contentType="CDATA" lang="en"><title>Studies on Energetic Salts Based on (2,4,6‐Trinitrophenyl)guanidine</title></titleInfo><name type="personal"><namePart type="given">Thomas M.</namePart><namePart type="family">Klapötke</namePart><affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</affiliation><affiliation>E-mail: tmk@cup.uni‐muenchen.de</affiliation><affiliation>Correspondence address: Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Frank</namePart><namePart type="family">Mieskes</namePart><affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Jörg</namePart><namePart type="family">Stierstorfer</namePart><affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><name type="personal"><namePart type="given">Michael</namePart><namePart type="family">Weyrauther</namePart><affiliation>Department of Chemistry, Ludwig‐Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany</affiliation><role><roleTerm type="text">author</roleTerm></role></name><typeOfResource>text</typeOfResource><genre type="article" displayLabel="article" authority="ISTEX" authorityURI="https://content-type.data.istex.fr" valueURI="https://content-type.data.istex.fr/ark:/67375/XTP-6N5SZHKN-D">article</genre><originInfo><publisher>WILEY‐VCH Verlag</publisher><place><placeTerm type="text">Weinheim</placeTerm></place><dateIssued encoding="w3cdtf">2016-04</dateIssued><dateCaptured encoding="w3cdtf">2015-12-10</dateCaptured><copyrightDate encoding="w3cdtf">2016</copyrightDate></originInfo><language><languageTerm type="code" authority="rfc3066">en</languageTerm><languageTerm type="code" authority="iso639-2b">eng</languageTerm></language><physicalDescription><extent unit="figures">6</extent><extent unit="tables">1</extent><extent unit="references">34</extent></physicalDescription><abstract lang="en">(2,4,6‐Trinitrophenyl)guanidine was synthesized and its thermal and energetic properties were investigated. The reaction of (2,4,6‐trinitrophenyl)guanidine with different acids, such as nitric, picric, perchloric, and hydrochloric acid results in protonation of (2,4,6‐trinitrophenyl)guanidine and the formation of the corresponding salts (cation : anion ratio 1 : 1). The reactions are performed at ambient temperature in H2O or EtOH and produce qualitatively pure products with energetic properties, which are typical of those of secondary explosives. The compounds were characterized using multinuclear NMR spectroscopy, IR and Raman spectroscopy, as well as mass spectrometry. Single crystal X‐ray diffraction studies were performed and the structures of the four different salts at low temperatures were determined. The thermal stabilities were measured using differential scanning calorimetry (DSC). The sensitivities were determined using the BAM drophammer and friction tests. The heats of formation were calculated by the atomization method based on CBS‐4M enthalpies. Using these values as well as the X‐ray or pycnometric densities, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code.</abstract><abstract type="graphical" lang="en"></abstract><note type="funding">U.S. Army Research Laboratory (ARL) - No. W911NF‐09‐2‐0018; </note><note type="funding">Armament Research, Development and Engineering Center (ARDEC) - No. W911NF‐12‐1‐0467; </note><note type="funding">Office of Naval Research (ONR) - No. ONR.N00014‐10‐1‐0535; No. ONR.N00014‐12‐1–0538; </note><subject lang="en"><genre>keywords</genre><topic>Energetic materials</topic><topic>Explosives</topic><topic>Crystal structures</topic><topic>Nitrobenzenes</topic><topic>Salt formation</topic></subject><relatedItem type="host"><titleInfo><title>Propellants, Explosives, Pyrotechnics</title></titleInfo><titleInfo type="abbreviated"><title>Propellants, Explosives, Pyrotechnics</title></titleInfo><genre type="journal" authority="ISTEX" authorityURI="https://publication-type.data.istex.fr" valueURI="https://publication-type.data.istex.fr/ark:/67375/JMC-0GLKJH51-B">journal</genre><note type="content"> As a service to our authors and readers, this journal provides supporting information supplied by the authors. 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