Electrochemical Oxidation of Alkylnitro Compounds
WP-1345
Objective
Electrochemical Oxidation of TNT
Many energetic materials of importance to Department of Defense (DoD) applications, such as bis-dinitropropyl acetal-formal (BDNPA/F), 2,2’,4,4’,6,6’-hexanitrostillbene (HNS), 2,2-dimethyl-2,2-dinitrobutane (DMDNB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), and 1,3,3-trinitroazetidine (TNAZ), share energetic structural elements consisting of nitro groups bound to carbon atoms. The production of such materials is generally accomplished with numerous powerful chemical oxidizers. Use of these reagents generates pernicious waste streams, and these chemical oxidizers are themselves environmentally costly to produce. The developent of environmentally benign production methods for these energetic materials would be beneficial to DoD.
The objective of this project was to develop a general technology for the synthesis of energetic materials using clean electrochemical oxidation methodology. This approach eliminates the use of strong chemical oxidizing agents and thus their byproducts and waste streams, providing a more environmentally sound manufacturing approach.
Technical Approach
This project explored the application of electrochemical oxidation technology to manufacture energetic materials of DoD interest such as BDNPA/F, TNAZ, TATB, and HNS. The oxidation of trinitrotoluene (TNT), 1-t-butyl-3-hydroxymethyl-3-nitroazetidine (HMNAz), phloroglucinol, and nitroethane were carried out under electrochemical conditions to manufacture the target compounds. These oxidations were evaluated for their efficacy and ability to be scaled to industrially useful quantities. Cursory economic feasibility of the approach at a production scale was estimated, and recommendations were made for further pursuit.
Results
Voltammetric investigations and electrochemical synthesis of the targeted chemistries were performed with several of these applications appearing to be promising. An electrochemical oxidation cell was used to perform bulk electrolysis experiments to isolate quantities of some of these materials for chemical identification. DMDNB, 2,2-dinitropropanol (DNPOH), the precursor to BDNPA/F, and 1-tert-butyl-3,3-dinitroazetidine (DNAZ), the precursor to TNAZ, were isolated and characterized. Application of this approach to manufacturing of these materials appears feasible, pending further development. Work to develop an electrochemical oxidation process continues under SERDP project WP-1460.
Benefits
Electrochemical reactions are among the cleanest of chemical conversion alternatives in that only electricity, catalytic electrode surfaces, and a solvent are required. Organic materials are minimized, and solvents may be recycled and reused. The industrial production of energetic materials using electrochemical synthesis could dramatically reduce the environmental impact of their manufacture by removing the need for chemical oxidizers and avoiding also the costs incurred in the disposal of waste by-products (Project Completed - 2004)
Project Documents
Points of Contact
Principal Investigator
Dr. Kirstin Warner
Naval Sea Systems Command (NAVSEA)
Phone: 301-744-4525
Fax: 301-744-6223
Project Documents
Document Types
- Fact Sheet - Brief project summary with links to related documents and points of contact.
- Final Report - Comprehensive report for every completed SERDP and ESTCP project that contains all technical results.
- Cost & Performance Report - Overview of ESTCP demonstration activities, results, and conclusions, standardized to facilitate implementation decisions.
- Technical Report - Additional interim reports, laboratory reports, demonstration reports, and technology survey reports.
- Guidance - Instructional information on technical topics such as protocols and user’s guides.
- Workshop Report - Summary of workshop discussion and findings.
- Multimedia - On demand videos, animations, and webcasts highlighting featured initiatives or technologies.
- Model/Software - Computer programs and applications available for download.
- Database - Digitally organized collection of data available to search and access.