Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer
This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition tempera...
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| Veröffentlicht in: | ChemPlusChem (Weinheim, Germany) Germany), 2019-01, Vol.84 (1), p.107-111 |
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| creator | Wang, Yinglei Liu, Yajing Lu, Tingting Gao, Fulei Zhao, Baodong |
| description | This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ⋅ cm−3, 16 J, 324 N, 235.9 °C and −50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ⋅ cm−3)0.5, and the glass transition temperature of GAP was reduced from −35 °C to −43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.
Explosive temperament: The azido ester 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA) was synthesized with good yield and high purity. It exhibits high energy, remarkable thermostability and good compatibility with glycidyl azide polymer (GAP). This indicates that the new compound has potential application in explosive and propellant formulations. |
| doi_str_mv | 10.1002/cplu.201800531 |
| format | Article |
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Explosive temperament: The azido ester 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA) was synthesized with good yield and high purity. It exhibits high energy, remarkable thermostability and good compatibility with glycidyl azide polymer (GAP). This indicates that the new compound has potential application in explosive and propellant formulations.</description><identifier>ISSN: 2192-6506</identifier><identifier>EISSN: 2192-6506</identifier><identifier>DOI: 10.1002/cplu.201800531</identifier><identifier>PMID: 31950745</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>azido esters ; Chemistry ; density functional calculations ; energetic materials ; Explosive forming ; Formulations ; Glass transition temperature ; Glycidyl azide polymer ; Mathematical analysis ; Molecular dynamics ; organic synthesis ; plasticizers ; Polymers ; Sensitivity ; Solubility parameters ; Synthesis ; Temperature ; Thermal decomposition ; Thermal stability ; Transition temperatures</subject><ispartof>ChemPlusChem (Weinheim, Germany), 2019-01, Vol.84 (1), p.107-111</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4391-ad4337a90f66918f5a1a295769983438af34182e5bdcc9ad46dcc931b0b784933</citedby><cites>FETCH-LOGICAL-c4391-ad4337a90f66918f5a1a295769983438af34182e5bdcc9ad46dcc931b0b784933</cites><orcidid>0000-0003-2260-1029</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fcplu.201800531$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fcplu.201800531$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31950745$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Wang, Yinglei</creatorcontrib><creatorcontrib>Liu, Yajing</creatorcontrib><creatorcontrib>Lu, Tingting</creatorcontrib><creatorcontrib>Gao, Fulei</creatorcontrib><creatorcontrib>Zhao, Baodong</creatorcontrib><title>Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer</title><title>ChemPlusChem (Weinheim, Germany)</title><addtitle>Chempluschem</addtitle><description>This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ⋅ cm−3, 16 J, 324 N, 235.9 °C and −50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ⋅ cm−3)0.5, and the glass transition temperature of GAP was reduced from −35 °C to −43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.
Explosive temperament: The azido ester 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA) was synthesized with good yield and high purity. It exhibits high energy, remarkable thermostability and good compatibility with glycidyl azide polymer (GAP). This indicates that the new compound has potential application in explosive and propellant formulations.</description><subject>azido esters</subject><subject>Chemistry</subject><subject>density functional calculations</subject><subject>energetic materials</subject><subject>Explosive forming</subject><subject>Formulations</subject><subject>Glass transition temperature</subject><subject>Glycidyl azide polymer</subject><subject>Mathematical analysis</subject><subject>Molecular dynamics</subject><subject>organic synthesis</subject><subject>plasticizers</subject><subject>Polymers</subject><subject>Sensitivity</subject><subject>Solubility parameters</subject><subject>Synthesis</subject><subject>Temperature</subject><subject>Thermal decomposition</subject><subject>Thermal stability</subject><subject>Transition temperatures</subject><issn>2192-6506</issn><issn>2192-6506</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkc1qGzEUhUVJSUKSbZZF0E0KtaP_GWVnTNoEDDW0WQvNzB2iIM84koYyXuUR8ox9ksp1fko2uQudi-53DxcOQqeUTCkh7Lxe-2HKCC0JkZx-QIeMajZRkqi9__oDdBLjHcmliGQF30cHnGpJCiEP0ebn2KVbiC5i2zV4Gfo1hOQg4r7F_M_D42zjmj4r-8ryW7l4Zrc_K0i3o_-yzvzoMXsGbQ3JJrjAM7zsE3TJWY__TfBlTBDw0tuYXO02EI7Rx9b6CCdPeoRuvl3-ml9NFj--X89ni0ktuKYT2wjOC6tJq5SmZSsttUzLQmldcsFL23JBSwayaupaZ1ptldOKVEUpNOdH6Gznm4-9HyAms3KxBu9tB_0QDcv7igkpVEY_v0Hv-iF0-TrDGC0E40qTTE13VB36GAO0Zh3cyobRUGK2wZhtMOYlmLzw6cl2qFbQvODPMWRA74DfzsP4jp2ZLxc3r-Z_AVvanOo</recordid><startdate>201901</startdate><enddate>201901</enddate><creator>Wang, Yinglei</creator><creator>Liu, Yajing</creator><creator>Lu, Tingting</creator><creator>Gao, Fulei</creator><creator>Zhao, Baodong</creator><general>Blackwell Publishing Ltd</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>4T-</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2260-1029</orcidid></search><sort><creationdate>201901</creationdate><title>Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer</title><author>Wang, Yinglei ; Liu, Yajing ; Lu, Tingting ; Gao, Fulei ; Zhao, Baodong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4391-ad4337a90f66918f5a1a295769983438af34182e5bdcc9ad46dcc931b0b784933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>azido esters</topic><topic>Chemistry</topic><topic>density functional calculations</topic><topic>energetic materials</topic><topic>Explosive forming</topic><topic>Formulations</topic><topic>Glass transition temperature</topic><topic>Glycidyl azide polymer</topic><topic>Mathematical analysis</topic><topic>Molecular dynamics</topic><topic>organic synthesis</topic><topic>plasticizers</topic><topic>Polymers</topic><topic>Sensitivity</topic><topic>Solubility parameters</topic><topic>Synthesis</topic><topic>Temperature</topic><topic>Thermal decomposition</topic><topic>Thermal stability</topic><topic>Transition temperatures</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Yinglei</creatorcontrib><creatorcontrib>Liu, Yajing</creatorcontrib><creatorcontrib>Lu, Tingting</creatorcontrib><creatorcontrib>Gao, Fulei</creatorcontrib><creatorcontrib>Zhao, Baodong</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Docstoc</collection><collection>MEDLINE - Academic</collection><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Yinglei</au><au>Liu, Yajing</au><au>Lu, Tingting</au><au>Gao, Fulei</au><au>Zhao, Baodong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer</atitle><jtitle>ChemPlusChem (Weinheim, Germany)</jtitle><addtitle>Chempluschem</addtitle><date>2019-01</date><risdate>2019</risdate><volume>84</volume><issue>1</issue><spage>107</spage><epage>111</epage><pages>107-111</pages><issn>2192-6506</issn><eissn>2192-6506</eissn><abstract>This study reports the synthesis and characterization of a novel azido ester plasticizer, 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA), with good yield and high purity. The density, impact sensitivity, friction sensitivity, thermal decomposition temperature and glass transition temperature were determined to be 1.326 g ⋅ cm−3, 16 J, 324 N, 235.9 °C and −50.4 °C, respectively. The plasticizing effect of ABAMPA on glycidyl azide polymer (GAP) was calculated by molecular dynamics, the solubility parameter difference value was 1.7(J ⋅ cm−3)0.5, and the glass transition temperature of GAP was reduced from −35 °C to −43 °C when the weight ratio of ABAMPA and GAP was 50 : 50. The new azido ester exhibits high energy, remarkable thermostability and good compatibility with GAP, which indicates that it would have potential application in explosive and propellant formulations.
Explosive temperament: The azido ester 3‐azido‐2,2‐bis(azidomethyl)propyl 2‐azidoacetate (ABAMPA) was synthesized with good yield and high purity. It exhibits high energy, remarkable thermostability and good compatibility with glycidyl azide polymer (GAP). This indicates that the new compound has potential application in explosive and propellant formulations.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>31950745</pmid><doi>10.1002/cplu.201800531</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0003-2260-1029</orcidid></addata></record> |
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| subjects | azido esters Chemistry density functional calculations energetic materials Explosive forming Formulations Glass transition temperature Glycidyl azide polymer Mathematical analysis Molecular dynamics organic synthesis plasticizers Polymers Sensitivity Solubility parameters Synthesis Temperature Thermal decomposition Thermal stability Transition temperatures |
| title | Synthesis and Properties of 3‐Azido‐2,2‐bis(azidomethyl)propyl 2‐Azidoacetate: A Potential Azido Ester Plasticizer |
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