Selective Extraction of N‐Heterocyclic Precursors of 1,3,5,7‐Tetranitro‐1,3,5,7‐tetraazacyclooctane (HMX) Using Molecularly Imprinted Polymers

Wang, Lei; Xu, Zhibin; Wang, Peng; Xue, Min; Dong, Xuemin; Meng, Zihui; Zhao, Lin

doi:10.1002/prep.201300016

Cited by 3 publications

(3 citation statements)

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“…It is still a great challenge to use MIPs to selectively extract N-heterocyclic targets from interference with high similarity in size and functionality. Wang et al developed a molecular imprinting technology to selectively extract the precursor of HMX, 1,3,5,7-tetraacetyl-1,3,5,7-tetraazacyclooctane (TAT), from a mixture of TAT and 1,3,5-triacetyl-1,3,5triazacyclohexane (the precursor of RDX) [25]. However, thus far, using MIP to isolate pure HMX and RDX from RDX/HMX mixtures had not been reported.…”

Section: F I G U R E 1 Molecular Structures Of Hmx and Rdxmentioning

confidence: 99%

“…Wang et al. developed a molecular imprinting technology to selectively extract the precursor of HMX, 1,3,5,7‐tetraacetyl‐1,3,5,7‐tetraazacyclooctane (TAT), from a mixture of TAT and 1,3,5‐triacetyl‐1,3,5‐triazacyclohexane (the precursor of RDX) . However, thus far, using MIP to isolate pure HMX and RDX from RDX/HMX mixtures had not been reported.…”

Section: Introductionmentioning

confidence: 99%

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Separation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5- triazacyclohexane by molecularly imprinted solid-phase extraction

et al. 2017

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Synthesis of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5-triazacyclohexane by the Bachmann process leads to a mixture of both. The separation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5-triazacyclohexane from their mixture is difficult because the sizes and physical properties of these homologous compounds are similar. For this purpose, seven molecularly imprinted polymers have been synthesized for each explosive, and a selective solid-phase extraction procedure has been developed. A molecularly imprinted polymer, synthesized with 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane as the template, methacrylic acid as the monomer and trimethylolpropane trimethacrylate as the cross-linking agent in a molar ratio of 1:8:8 showed the best separation capability. A packed cartridge containing this polymer can be reused for 23 solid-phase extraction cycles without repacking, and the total separation capability toward 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane reached 6.81 mg per gram of polymer. 1,3,5-Trinitro-1,3,5-triazacyclohexane was not detected in the separated 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane by high-performance liquid chromatography and vice versa. This newly developed method had the advantages of high recovery (100%) and purity, environmental friendliness, and room temperature operability. This study showed that some molecularly imprinted polymers that cannot absorb target analytes well in the solvent in which the polymers were polymerized might have high-binding capacity for the analytes and show imprinting effects in other solvents.

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Section: F I G U R E 1 Molecular Structures Of Hmx and Rdxmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Separation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5- triazacyclohexane by molecularly imprinted solid-phase extraction

et al. 2017

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“…1,3,5‐Triacetyl‐1,3,5‐triazacyclohexane (TRAT, Figure (b)) is a by‐product of the preparation of TAT. In our previous study on solid phase extraction, MIPs were prepared with TAT and TRAT as templates respectively (Wang et al, ). The TAT‐MIP can selectively absorb TAT, and TRAT‐MIPs prepared with the same imprinting method and imprinting system including functional monomer, crosslinker, and solvent cannot absorb its template TRAT.…”

Section: Introductionmentioning

confidence: 99%

Understanding the relationships between molecule structure and imprinting effect of two acetyl‐nitrogen heterocyclic compounds

Wang

Dong

Xue

et al. 2016

J of Molecular Recognition

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The molecularly imprinted polymers (MIPs) for two structural analogs, 1,3,5-triacetyl-1,3,5-triazacyclohexane (TRAT) and 1,3,5,7-tetraacetyl-1,3,5,7-tetraazacyclooctane (TAT), have been synthesized respectively under the same conditions. The TAT-MIP showed excellent imprinting effect, whereas the TRAT-MIP did not. To understand the different imprinting effects of the MIPs prepared from these two templates, the geometric structures and energetic properties of complexes formed around TAT and TRAT were studied computationally. The results indicate that in liquid phase, for the complexes formed with TAT and its nearest neighbor molecules, the magnitude of the binding energy increases with the number of surrounding TAT, methacrylic acid, and acetonitrile (ACT), whereas for the cases of TRAT, the magnitude of the binding energy increases with the number of surrounding TRAT and trimethylolpropane trimethacrylate. The studied systems form stronger and thus more stable networks encapsulating TAT than with TRAT. ACT may also play an important role in the polymerization phase in stabilizing the shapes of the cavities that TATs reside in. We propose these as the major factors that affect the different imprinting effects of the two MIPs. Copyright © 2016 John Wiley & Sons, Ltd.

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Molecularly Imprinted Polymers

2018

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Molecularly imprinted polymers are synthetic receptors for a targeted molecule. As such, they are analogues of the natural antibody–antigen systems. In this review, after a recounting of the early history of the general field, we specifically focus on the application of these polymers as sensors. In these applications, the polymers are paired with a reporting system, which may be electrical, electrochemical, optical, or gravimetric. The presence of the targeted molecule effects a change in the reporting agent, and a calibrated quantity of the target is recorded. In this review, we describe the imprinted polymer production processes, the techniques used for reporting, and the applications of the reported sensors. A brief survey of recent applications to gas-phase sensing is included, but the focus is primarily on the development of sensors for targets in solution. Included among the applications are those designed to detect toxic chemicals, toxins in foods, drugs, explosives, and pathogens. The application of computational chemistry to the development of new imprinted polymers is included as is a brief assessment of future developments.

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Selective Extraction of N‐Heterocyclic Precursors of 1,3,5,7‐Tetranitro‐1,3,5,7‐tetraazacyclooctane (HMX) Using Molecularly Imprinted Polymers

Cited by 3 publications

References 28 publications

Separation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5- triazacyclohexane by molecularly imprinted solid-phase extraction

Separation of 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane and 1,3,5-trinitro-1,3,5- triazacyclohexane by molecularly imprinted solid-phase extraction

Understanding the relationships between molecule structure and imprinting effect of two acetyl‐nitrogen heterocyclic compounds

Molecularly Imprinted Polymers

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