Increased handling sensitivity of molten erythritol tetranitrate (ETN)

Lease, Nicholas; Kay, Lisa M.; Chávez, David E.; Robbins, David; Manner, Virginia W.

doi:10.1016/j.jhazmat.2018.12.110

Cited by 24 publications

(32 citation statements)

References 13 publications

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“…Additionally, recent reports from our group have shown that changes to the physical state or melting point can have dramatic changes toward the explosive sensitivity. 11,12 In fact, molten ETN has an impact sensitivity of ∼0.24 J, which is within the error of the azide derivatives. 11 With the nitramine derivatives of ETN, a decrease in the handling sensitivity relative to ETN was observed with the azides, a decrease in the sensitivity was observed.…”

Section: ■ Results and Discussionmentioning

confidence: 71%

“…11,12 In fact, molten ETN has an impact sensitivity of ∼0.24 J, which is within the error of the azide derivatives. 11 With the nitramine derivatives of ETN, a decrease in the handling sensitivity relative to ETN was observed with the azides, a decrease in the sensitivity was observed. The tetranitramine, compound (4), showed a considerably decreased impact sensitivity (12.7 ± 1.0 J) compared to ETN.…”

Section: ■ Results and Discussionmentioning

confidence: 98%

“…The characteristic thermodynamic stabilities and decomposition pathways of each functional group can influence the stability and explosive sensitivity of the molecule. Additionally, altering functional groups on a molecule can change physical characteristics such as melting point, physical state of the compound, and density, all of which have been shown to affect the overall sensitivity of the molecule. − …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity

et al. 2020

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Understanding the factors that affect explosive sensitivity is paramount to the safe handling and development of new explosives molecules. Erythritol tetranitrate (ETN) is an explosive that recently has attracted significant attention in the explosives community because of its ease of synthesis and physical properties. Herein, we report the synthesis of ETN derivatives using azide, nitramine, and nitrate ester functional groups. Impact, spark, and friction sensitivity measurements, computationally calculated explosive properties, and the crystal structure analysis of the ETN derivatives are reported. Mixing explosive functional groups led to changes in the explosive sensitivity, explosive performance as well as physical properties including melting point and physical state at room temperature. Overall, we have demonstrated that combining functional groups can enable the tuning of explosive and physical properties of a molecule. This tunability can potentially aid in the development of new explosives in which characteristics are varied to meet certain specifications.

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Section: ■ Results and Discussionmentioning

confidence: 71%

Section: ■ Results and Discussionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity

et al. 2020

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“…The increase in attention ETN has received can be attributed to the now ubiquitous nature of erythritol as an artificial sweetener, owing to the modern inexpensive production methods via microbial conversion of starch from corn to glucose which can be fermented to form erythritol [2]. As a close cousin to the very common explosive pentaerythritol tetranitrate (PETN), ETN has high explosive performance properties like that of PETN, but is melt‐castable and has a slightly positive oxygen balance [3–6]. Numerous web pages and videos exist on the internet that gives detailed information on the synthesis of ETN.…”

Section: Introductionmentioning

confidence: 99%

Investigation of the Impurities in Erythritol Tetranitrate (ETN) Using UHPLC‐QTOF

Freye

Nguyen

Tappan

2021

Propellants Explo Pyrotec

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In order to further gain a comprehensive chemical understanding of erythritol tetranitrate (ETN), the synthesis impurities of ETN were investigated using ultrahigh performance liquid chromatography with tandem high resolution mass spectrometry (UHPLC‐MS/MS). A total of 12 impurities were identified relating to the synthesis of ETN. We have synthesized pure analytical standards of erythritol‐1,4‐dinitrate (1,4‐EDiN) and erythritol‐1,2,4‐trinitrate (1,2,4‐ETriN). These isomerically pure standards have allowed for confirmation of the identity of some of the discovered impurities. Additionally, partially nitrated with sulfate substituted erythritol was identified which is theorized to have formed from the incomplete displacement of the formed sulfate group on the alcohol position during nitration.

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“…The discovery of nitrate esters shown in Figure 1 dates to the mid‐ to late‐1800’s. Recently erythritol tetranitrate (ETN) has received considerable attention [3–11]. ETN has a similar explosive performance to PETN; albeit at the cost of increased sensitivity [12].…”

Section: Introductionmentioning

confidence: 99%

Characterization of the Hexanitrate Esters of Sugar Alcohols

McLennan

Brown-Nash

Busby

et al. 2021

Propellants Explo Pyrotec

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The hexanitrates of the six‐carbon sugars mannitol and sorbitol were prepared and studied to gain insight in their relative stabilities. Synthesis and characterization of these materials resulted in the identification of two new crystalline polymorphs, one for each hexanitrate. Mannitol hexanitrate (MHN) exposed to elevated temperatures exhibited a different structure when measured by x‐ray diffraction (XRD) and Raman spectroscopy; however, no differences were observed in the thermal behavior. Sorbitol hexanitrate (SHN) has two distinct crystalline polymorphs that result in different melting behavior and differences in Raman and XRD. Thermal stability of these hexanitrates was also examined; despite being isomers, SHN and MHN differ in their long‐term thermal stability.

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Increased handling sensitivity of molten erythritol tetranitrate (ETN)

Cited by 24 publications

References 13 publications

Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity

Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity

Investigation of the Impurities in Erythritol Tetranitrate (ETN) Using UHPLC‐QTOF

Characterization of the Hexanitrate Esters of Sugar Alcohols

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