Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5)

Journal article

Millar, RW and Philbin, SP (1998). Clean nitrations: Novel syntheses of nitramines and nitrate esters by nitrodesilylation reactions using dinitrogen pentoxide (N2O5). Tetrahedron. 53 (12), pp. 4371-4386. https://doi.org/10.1016/S0040-4020(97)00093-8
AuthorsMillar, RW and Philbin, SP
Abstract

In this novel nitration method dinitrogen pentoxide (N2O5) in an inert solvent is used as the nitrating agent, thereby removing the need for strong acids as the reaction medium. The N2O5 cleaves heteroatom-silicon bonds, in silylamines and silyl ethers respectively, to yield the desired energetic groupings (nitramines or nitrate esters respectively) without liberation of acids which would occur with conventional substrates (amines or alcohols). These nitrodesilylation reactions proceed cleanly and in good yield, and the scope of the reaction is illustrated by. 29 examples, some of which produce high energy compounds, notably plasticisers and an energetic polymer precursor. These reactions are therefore potentially clean nitrations for the manufacture of energetic compounds which will minimise the impact of this activity on the environment in the future.

Keywords0305 Organic Chemistry; 0304 Medicinal And Biomolecular Chemistry; Organic Chemistry
Year1998
JournalTetrahedron
Journal citation53 (12), pp. 4371-4386
PublisherElsevier
Digital Object Identifier (DOI)https://doi.org/10.1016/S0040-4020(97)00093-8
Publication dates
Print26 Mar 1998
Publication process dates
Deposited24 Sep 2018
Accepted23 Jan 1997
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Zhang, J., Pu, S., Philbin, S., Li, H., Skitmore, M. and Ballesteros-Pérez, P. (2020). Environmental Regulation and Green Productivity of the Construction Industry in China. Proceedings of the Institution of Civil Engineers: Engineering Sustainability. 174 (2). https://doi.org/10.1680/jensu.20.00013
Measuring the Capacity Utilization of China's Transportation Industry under Environmental Constraints
Zhang, J, Cai, W, Philbin, SP, Li, H, Lu, Q, Ballesteros-Pérez, P and Yang, G (2020). Measuring the Capacity Utilization of China's Transportation Industry under Environmental Constraints. Transportation Research Part D: Transport and Environment. 85, pp. 102450-102450. https://doi.org/10.1016/j.trd.2020.102450
Measuring Sustainable Development Goal Targets on Infrastructure Projects
Mansell, P and Philbin, SP (2020). Measuring Sustainable Development Goal Targets on Infrastructure Projects. Journal of Modern Project Management. 8 (1).
Systematic Literature Review of Project Manager’s Leadership Competencies
Ahmed, R., Philbin, S.P. and Cheema, F. (2020). Systematic Literature Review of Project Manager’s Leadership Competencies. Engineering, Construction and Architectural Management. https://doi.org/10.1108/ECAM-05-2019-0276
Measuring PMO Performance – Application of the Balanced Scorecard in a Collaborative Research Context
Philbin, S P and Kaur, R (2020). Measuring PMO Performance – Application of the Balanced Scorecard in a Collaborative Research Context. Journal of Modern Project Management. 7 (4), pp. 1-22. https://doi.org/10.19255/JMPM02212
Studies of Novel Nitro Substituted Nitrogen Heterocyclic Compounds
Philbin, SP, Millar, RW and Coombes, RG (1999). Studies of Novel Nitro Substituted Nitrogen Heterocyclic Compounds. National Defense Industrial Association (NDIA) Annual Symposium on Insensitive Munitions and Energetic Materials Technology. Tampa, Florida, USA 10 - 12 Nov 1999
Current Strands of Research in DERA on the Chemistry of Energetic Materials and Insensitive Munitions
Philbin, SP (2000). Current Strands of Research in DERA on the Chemistry of Energetic Materials and Insensitive Munitions. National Defense Industrial Association (NDIA) Annual Conference on Insensitive Munitions and Energetic Materials (IM/EM) Technology. San Antonio, Texas, USA 27 - 30 Nov 2000
Enterprise Education for Engineers with the Technology Evaluation and Commercialisation Framework
Philbin, S. (2019). Enterprise Education for Engineers with the Technology Evaluation and Commercialisation Framework. 2019 International Entrepreneurship Educators Conference (IEEC). Oxford Brookes University 04 - 06 Sep 2019
Developing a Revenue Sharing Method for an Operational Transfer-Operate-Transfer Project
Yanhua Du, Jun Fang, Yongjian Ke, Philbin, S. and Jingxiao Zhang (2019). Developing a Revenue Sharing Method for an Operational Transfer-Operate-Transfer Project. Sustainability. 11, pp. 6436-3454. https://doi.org/10.3390/su11226436
Assessing the Impact of Infrastructure Projects on Global Sustainable Development Goals
Mansell, P., Philbin, S., Broyd, T. and Nicholson, I. (2019). Assessing the Impact of Infrastructure Projects on Global Sustainable Development Goals. Proceedings of the ICE - Engineering Sustainability. https://doi.org/10.1680/jensu.19.00044
Perspectives on the Techno-Economic Analysis of Carbon Capture and Storage
Philbin, S. and Hsueh-Ming, S. (2019). Perspectives on the Techno-Economic Analysis of Carbon Capture and Storage. Journal of technology management & innovation. 14 (3). https://doi.org/10.4067/S0718-27242019000300003
Infrastructure Projects’ Impact on Sustainable Development – Case Study of a Water-Utility Company
Mansell, P., Philbin, S.P. and Broyd, T. (2019). Infrastructure Projects’ Impact on Sustainable Development – Case Study of a Water-Utility Company. International Conference on Organization, Technology and Management in Construction (OTMC). Zagreb, Croatia 04 - 07 Sep 2019
Engineering Education, Skills and Industry Alignment – Comparative Analysis of the UK and USA
Philbin, S., Kauffmann, P. and Wyrick, D. (2019). Engineering Education, Skills and Industry Alignment – Comparative Analysis of the UK and USA. 440th American Society for Engineering Management (ASEM) International Annual Conference. Philadelphia (PA), USA. 23 - 26 Oct 2019
Techno-economic analysis of the adoption of electric vehicles
Kennedy, D and Philbin, S. (2019). Techno-economic analysis of the adoption of electric vehicles. Frontiers of Engineering Management. https://doi.org/10.1007/s42524-019-0048-x
Why project management is critical to achieving the SDGs and how this can be achieved
Mansell, P., Philbin, SP and Plodowski, A (2019). Why project management is critical to achieving the SDGs and how this can be achieved. Delft TU Project Management Congress 2019. Delft, The Netherlands 11 - 12 Apr 2019
‘Call to Arms’: Using the Creating Shared Value Business Governance Paradigm to Deliver Projects’ Business-Society Impact Against the UN SDG 2030 Targets
Mansell, P., Philbin, SP and Konstantinou, E (2019). ‘Call to Arms’: Using the Creating Shared Value Business Governance Paradigm to Deliver Projects’ Business-Society Impact Against the UN SDG 2030 Targets. EURAM (European Academy of Management) 2019 Conference. Lisbon, Portugal 26 - 28 Jun 2019
Clean synthesis of energetic materials using solid-supported reactions and related technologies
Millar, RW, Colclough, ME, Claridge, RP, Hamid, J, Philbin, SP and Chauhan, N (2000). Clean synthesis of energetic materials using solid-supported reactions and related technologies. ChemInform. 31 (49). https://doi.org/10.1002/chin.200049277
Solid Nitrating Agent Incorporating Dinitrogen Pentoxide
Millar, RW, Claridge, RP and Philbin, SP (1999). Solid Nitrating Agent Incorporating Dinitrogen Pentoxide.
Solid Nitrating Reagent
Claridge, RP, Millar, RW and Philbin, SP (2000). Solid Nitrating Reagent.
Clean Synthesis of Energetic Materials Using Solid-Supported Reactions and Related Technologies
Millar, R, Colclough, ME, Claridge, RP, Hamid, J, Philbin, SP and Chauhan, N (2000). Clean Synthesis of Energetic Materials Using Solid-Supported Reactions and Related Technologies. 31st International Annual Conference of Institut für Chemische Technologie (ICT). Karlsruhe, Germany 27 - 30 Jun 2000 Fraunhofer-Institut für Chemische Technologie.
Novel insensitive high explosive compounds based on heterocyclic nuclei- Pyridines, pyrimidines, pyrazines and their benzo analogues
Millar, RW, Philbin, SP, Claridge, RP and Hamid, J (2002). Novel insensitive high explosive compounds based on heterocyclic nuclei- Pyridines, pyrimidines, pyrazines and their benzo analogues. Energetic Materials- Synthesis, Production and Application.
Developing an integrated approach to system safety engineering
Philbin, SP (2010). Developing an integrated approach to system safety engineering. Engineering Management Journal. 22 (2), pp. 56-67. https://doi.org/10.1080/10429247.2010.11431864
Investigating the Scope for Agile Project Management to Be Adopted by Higher Education Institutions
Philbin, SP (2017). Investigating the Scope for Agile Project Management to Be Adopted by Higher Education Institutions. in: Mahmood, Z (ed.) Software Project Management for Distributed Computing Springer. pp. 345-366
Preparation of 2, 5-Diamino-3, 6-Dinitropyrazine (ANPZ-i): A Novel Candidate High Energy Insensitive Explosive
Philbin, SP, Millar, RW and Coombes, RG (2000). Preparation of 2, 5-Diamino-3, 6-Dinitropyrazine (ANPZ-i): A Novel Candidate High Energy Insensitive Explosive. Propellants, Explosives, Pyrotechnics. 25 (6), pp. 302-306. https://doi.org/10.1002/1521-4087%28200012%2925%3A6<302%3A%3AAID-PREP302>3.0.CO%3B2-W
Studies of novel heterocyclic insensitive high explosive compounds: pyridines, pyrimidines, pyrazines and their bicyclic analogues
Millar, RW, Philbin, SP, Claridge, RP and Hamid, J (2004). Studies of novel heterocyclic insensitive high explosive compounds: pyridines, pyrimidines, pyrazines and their bicyclic analogues. Propellants, Explosives, Pyrotechnics. 29 (2), pp. 81-92. https://doi.org/10.1002/prep.200400033
Managing Projects through Systems Engineering Methodologies
Philbin, SP (2008). Managing Projects through Systems Engineering Methodologies. Proceedings of the 29th American Society for Engineering Management (ASEM) Annual Conference. United States Military Academy (USMA) at West Point (NY), USA 12 - 15 Nov 2008
System Safety Engineering for a High-Pressure Experimental Research Facility
Philbin, SP (2009). System Safety Engineering for a High-Pressure Experimental Research Facility. Proceedings of the 30th American Society for Engineering Management (ASEM) Annual Conference. Springfield (MO), USA 14 - 17 Oct 2009
Management Framework for Developing University-Industry Research Collaborations
Philbin, SP (2009). Management Framework for Developing University-Industry Research Collaborations. Proceedings of the Annual Meeting and Symposium of the Society of Research Administrators (SRA) International. Seattle (WA), USA 25 - 28 Oct 2009
Value for Money Model for Industrial Investment in University Research
Philbin, SP (2010). Value for Money Model for Industrial Investment in University Research. Proceedings of the 21st International Society for Professional Innovation Management (ISPIM) Annual Conference on the Dynamics of Innovation. Bilbao, Spain 06 - 09 Jun 2010
An Investigation of Programme Management and Application to a University Research Institute
Philbin, SP (2010). An Investigation of Programme Management and Application to a University Research Institute. Proceedings of the 31st American Society for Engineering Management (ASEM) Annual Conference. Fayetteville (AR), USA 13 - 16 Oct 2010
Case Study Investigation of the Development and Management of a University Research Institute
Philbin, SP (2010). Case Study Investigation of the Development and Management of a University Research Institute. Proceedings of the Annual Meeting and Symposium of the Society of Research Administrators (SRA) International. Chicago (IL), USA 24 - 28 Oct 2010
University-Industry Strategic Alliances: Management Framework and Case Study Investigation
Philbin, SP (2011). University-Industry Strategic Alliances: Management Framework and Case Study Investigation. Proceedings of the 32nd American Society for Engineering Management (ASEM) International Annual Conference. Lubbock (TX), USA 19 - 22 Oct 2011
Knowledge Management Strategy for University-Industry Research Collaboration
Philbin, SP (2012). Knowledge Management Strategy for University-Industry Research Collaboration. Proceedings of the 33rd American Society for Engineering Management (ASEM) International Annual Conference. Virginia Beach (VA), USA 17 - 20 Oct 2012
Developing an Integrated Systems Perspective of Engineering Project Management
Philbin, SP (2013). Developing an Integrated Systems Perspective of Engineering Project Management. Proceedings of the 34th American Society for Engineering Management (ASEM) International Annual Conference. Minneapolis (MN), USA 03 - 05 Oct 2013
In Search of New Organisational Forms – The Case for Open Innovation and Crowdsourcing
Philbin, SP (2014). In Search of New Organisational Forms – The Case for Open Innovation and Crowdsourcing. Proceedings of the 35th American Society for Engineering Management (ASEM) International Annual Conference. Virginia Beach (VA), USA 15 - 18 Oct 2014 pp. 1-1
Exploring the application of agile management practices to higher education institutions
Philbin, SP (2015). Exploring the application of agile management practices to higher education institutions. Proceedings of the 36th American Society for Engineering Management (ASEM) International Annual Conference. Indianapolis (IN), USA 07 - 10 Oct 2015 pp. 1-1
Investigation of a systems-based design and planning approach to a facilities development project
Philbin, SP (2009). Investigation of a systems-based design and planning approach to a facilities development project. 2009 IEEE International Conference on Industrial Engineering and Engineering Management. Hong Kong, China 08 - 11 Dec 2009 pp. 608-612 https://doi.org/10.1109/IEEM.2009.5373261
Developing and Managing University-Industry Research Collaborations through a Process Methodology/Industrial Sector Approach.
Philbin, SP (2010). Developing and Managing University-Industry Research Collaborations through a Process Methodology/Industrial Sector Approach. Journal of Research Administration. 41 (3), pp. 51-68.
An environmentally-friendly route to nitramines and nitrate esters via nitrodesilylation chemistry using dinitrogen pentoxide
Millar, RW and Philbin, SP (1996). An environmentally-friendly route to nitramines and nitrate esters via nitrodesilylation chemistry using dinitrogen pentoxide. 27th International Annual Conference of ICT. Karlsruhe, Germany 25 - 28 Jun 1996 pp. 26-1
Managing complex technology projects
Philbin, SP (2008). Managing complex technology projects. Research-Technology Management. 51, pp. 32-39. https://doi.org/10.1080/08956308.2008.11657493
Measuring the performance of research collaborations
Philbin, SP (2008). Measuring the performance of research collaborations. Measuring Business Excellence. 12 (3), pp. 16-23. https://doi.org/10.1108/13683040810900368
Application of systems engineering and systems thinking to project management
Philbin, SP (2010). Application of systems engineering and systems thinking to project management. in: Collins, RJ (ed.) Project Management Nova Science Publishers, Inc.. pp. 153-168
An Investigation of the Development and Management of University Research Institutes.
Philbin, SP (2011). An Investigation of the Development and Management of University Research Institutes. Journal of Research Administration. 42 (Spring), pp. 103-122.
Management system for multidisciplinary university research institutes
Philbin, SP (2011). Management system for multidisciplinary university research institutes. First International Technology Management Conference. San Jose, CA, USA 27 - 30 Jun 2011 pp. 657-665
Emerging Requirements for Technology Management: A Sector-based Scenario Planning Approach
Philbin, SP (2013). Emerging Requirements for Technology Management: A Sector-based Scenario Planning Approach. Journal of technology management & innovation. 8 (3), pp. 34-44. https://doi.org/10.4067/S0718-27242013000400004
Exploring research institutes: Structures, functioning and typology
Philbin, SP, Jones, D, Brandon, NP and Hawkes, AD (2014). Exploring research institutes: Structures, functioning and typology. PICMET '14 Conference: Portland International Center for Management of Engineering and Technology; Infrastructure and Service Integration. Kanazawa, Japan 27 - 31 Jul 2014 pp. 2569-2582
Diagnostic framework and health check tool for engineering and technology projects
Philbin, SP and Kennedy, DA (2014). Diagnostic framework and health check tool for engineering and technology projects. Journal of Industrial Engineering and Management. 7 (5), pp. 1145-1166. https://doi.org/10.3926/jiem.1150
Exploring the challenges and opportunities for higher education institutions: Work domain analysis and development of strategic options
Philbin, SP (2015). Exploring the challenges and opportunities for higher education institutions: Work domain analysis and development of strategic options. PICMET '15 Conference: Portland International Center for Management of Engineering and Technology; Management of the Technology Age. Portland, Oregon, USA 02 - 06 Aug 2015 pp. 1137-1150
Process model for university-industry research collaboration
Philbin, SP (2008). Process model for university-industry research collaboration. European Journal of Innovation Management. 11 (4), pp. 488-521. https://doi.org/10.1108/14601060810911138
Bid management: A systems engineering approach
Philbin, SP (2008). Bid management: A systems engineering approach. The Journal of High Technology Management Research. 19 (2), pp. 114-127. https://doi.org/10.1016/j.hitech.2008.10.004
Design and implementation of the Balanced Scorecard at a university institute
Philbin, SP (2011). Design and implementation of the Balanced Scorecard at a university institute. Measuring Business Excellence. 15 (3), pp. 34-45. https://doi.org/10.1108/13683041111161148
Resource-based view of university-industry research collaboration
Philbin, SP (2012). Resource-based view of university-industry research collaboration. 2012 Proceedings of PICMET '12: Technology Management for Emerging Technologies.. IEEE 29 Jul - 02 Aug 2012 pp. 400-411
Managing university-industry research partnerships through a process of alignment
Philbin, SP (2013). Managing university-industry research partnerships through a process of alignment. 2013 Proceedings of PICMET '13: Technology Management for Emerging Technologies.. 28 Jul - 01 Aug 2013 pp. 1848-1859
Applying an Integrated Systems Perspective to the Management of Engineering Projects
Philbin, SP (2015). Applying an Integrated Systems Perspective to the Management of Engineering Projects. Frontiers of Engineering Management. 2 (1), pp. 19-30. https://doi.org/10.15302/J-FEM-2015004
Research and Grant Management: The Role of the Project Management Office (PMO) in a European Research Consortium Context.
Wedekind, GK and Philbin, SP (2018). Research and Grant Management: The Role of the Project Management Office (PMO) in a European Research Consortium Context. Journal of Research Administration. 49 (1), pp. 43-62.
University-Industry Research Collaborations - Trends, Insights and Management Practice
Philbin, SP (2018). University-Industry Research Collaborations - Trends, Insights and Management Practice. Workshop - When Science and Business Talk. Birkbeck, University of London 04 May 2018
The imperative need to develop guidelines to manage human versus machine intelligence
Kennedy, D and Philbin, SP (2018). The imperative need to develop guidelines to manage human versus machine intelligence. Frontiers of Engineering Management. 5 (2), pp. 182-194. https://doi.org/10.15302/J-FEM-2018085
PMO Implementation for Project Management in a Collaborative Research Context
Philbin, SP (2018). PMO Implementation for Project Management in a Collaborative Research Context. Proceedings of the 39th American Society for Engineering Management (ASEM) International Annual Conference. Coeur d'Alene (ID), USA 17 - 20 Oct 2018
Investigating the Critical Success Factors for the Management of Carbon Capture and Storage (CCS) Projects
Philbin, SP and Hsueh Ming Wang, S (2017). Investigating the Critical Success Factors for the Management of Carbon Capture and Storage (CCS) Projects. International Forum on Engineering Science and Technology Development Strategy – Clean Energy Technology and Engineering Management, Chinese Academy of Engineering (CAE). Beijing, China 17 - 19 May 2017
Building a Project Management Office to Support Collaborative Research Projects
Philbin, SP (2017). Building a Project Management Office to Support Collaborative Research Projects. Annual Meeting of the Society of Research Administrators (SRA) International. Vancouver, Canada 14 - 18 Oct 2017
Investigating the Application of Project Management Principles to Research Projects – An Exploratory Study
Philbin, SP (2017). Investigating the Application of Project Management Principles to Research Projects – An Exploratory Study. Proceedings of the 38th American Society for Engineering Management (ASEM) International Annual Conference. Huntsville (AL), USA 18 - 21 Oct 2017
Becoming a Complete Project Leader
Philbin, SP and Kennedy, D (2016). Becoming a Complete Project Leader. Industrial Engineer. 48 (2), pp. 39-43.
Business Planning Methodology to Support the Development of Strategic Academic Programs.
Philbin, SP and Mallo, CA (2016). Business Planning Methodology to Support the Development of Strategic Academic Programs. Journal of Research Administration. 47 (1), pp. 23-39.
Insights from Managing Complex Research, Technology and Engineering Projects in Academia
Philbin, SP (2016). Insights from Managing Complex Research, Technology and Engineering Projects in Academia. Bernie Sarchet Graduate Seminar Series to Commemorate 50th Anniversary of the Engineering Management & Systems Engineering Department at Missouri University of Science and Technology. Rolla, Missouri, USA
Exploring the Project Management Office (PMO)–Role, Structure and Processes
Philbin, SP (2016). Exploring the Project Management Office (PMO)–Role, Structure and Processes. Proceedings of the 37th American Society for Engineering Management (ASEM) International Annual Conference. Charlotte (NC), USA. 26 - 29 Oct 2016 pp. 1-11
Management of Engineering Projects - Critical Success Factors and Integrated Systems Perspective
Philbin, SP (2015). Management of Engineering Projects - Critical Success Factors and Integrated Systems Perspective. International Summit Forum on Engineering Science and Technology Development Strategy, Chinese Academy of Engineering (CAE). Guangzhou, China 12 - 15 May 2015
Corporate Partnering and Knowledge Transfer at Imperial College London
Philbin, SP (2014). Corporate Partnering and Knowledge Transfer at Imperial College London. 2nd Severance Global Patent Fair at Yonsei University Health System. Seoul, Korea 27 Jan 2014
Strategies for Managing Successful Partnerships with Industry
Philbin, SP (2014). Strategies for Managing Successful Partnerships with Industry. Annual Meeting of the Society of Research Administrators (SRA) International. San Diego (CA), USA 20 - 21 Oct 2014
Applying a little reason to your projects
Kennedy, D and Philbin, SP (2013). Applying a little reason to your projects. Industrial Management. 55 (2).
Insights from the Development and Management of the Institute of Shock Physics
Philbin, SP (2011). Insights from the Development and Management of the Institute of Shock Physics. University of Cambridge and Imperial College Business School Joint Workshop on Managing University-Industry Centres. Imperial College London 27 Sep 2011
Enterprise Projects – Creating a New University Institute
Philbin, SP (2011). Enterprise Projects – Creating a New University Institute. 32nd American Society for Engineering Management (ASEM) International Annual Conference. Lubbock, Texas, USA 19 - 22 Oct 2011
Systems Engineering Tools for the Surveillance and Protection of Complex Networks and their Infrastructures
Philbin, SP (2007). Systems Engineering Tools for the Surveillance and Protection of Complex Networks and their Infrastructures. 2nd European Conference on Security Research. Berlin, Germany 26 - 27 Mar 2007
Studies of novel nitro-substituted nitrogen heterocyclic compounds
Philbin, SP (2001). Studies of novel nitro-substituted nitrogen heterocyclic compounds. PhD Thesis Brunel University Chemistry Unit, Institute of Physical and Environmental Sciences