Synthesis and Degradation of Hexamethylene Triperoxide Diamine (HMTD)

Oxley, Jimmie C.; Smith, James L.; Porter, Matthew; McLennan, Lindsay; Colizza, Kevin; Zeiri, Yehuda; Kosloff, Ronnie; Dubnikova, Faina

doi:10.1002/prep.201500151

Cited by 24 publications

(16 citation statements)

References 26 publications

(29 reference statements)

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“…al. [24] and Steinkamp et al [25], molecular HMTD vapor was not observed using the methods employed in the course of this study; however, a variety of volatile decomposition products with vapor concentrations estimated in the ppb range were detected. Based on previous work, it was predicted that humidity would have the greatest effect on decomposition as water has been shown to facilitate the decomposition of HMTD.…”

Section: Discussionmentioning

confidence: 44%

“…al. had indicated that residual citric acid can destabilize HMTD [24]. It is presumed that formic acid would have a similar effect.…”

Section: Discussionmentioning

confidence: 99%

“…In one study, Oxley et al identified N,N 0dimethylformamide, N,N 0 -methylenebis(formamide), trimethylamine, and hexamine as decomposition products that comprise the HMTD vapor signature [16]. In another, the headspace of crude and recrystallized HMTD were examined in the presence of different levels of humidity and of different ages, and found trimethylamine and dimethylformamide being in the greatest abundance [24]. Though this study did not go into detail, it appears that variables such as humidity and age affect the presence of these decomposition products.…”

Section: Introductionmentioning

confidence: 99%

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Variation in the headspace of bulk hexamethylene triperoxide diamine (HMTD) with time, environment, and formulation

2017

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a b s t r a c tHexamethylene triperoxide diamine (HMTD) is a homemade peroxide explosive that has become of concern to homeland security due to the ease of synthesis and commercial availability of the materials required for its synthesis. Detection is a challenge because of its exceedingly low vapor pressure and high thermal lability. Though molecular HMTD vapor is essentially undetectable under most circumstances, HTMD is known to degrade under ambient conditions, producing volatile products that could aid in detection. This work studies the evolution of these volatile organic compounds over time and across a number of variables including synthesis method, precursors, storage time, and storage environment. The composition and quantity of these volatiles were compared across these variables. Analysis of the headspace of bulk HMTD was carried out using solid phase microextraction (SPME) with gas chromatography/mass spectrometry (GC/MS). Decomposition was also monitored by gravimetric analysis. Results herein reveal that formic acid is the most abundant decomposition product while formaldehyde is the most commonly detected across all variables. Synthesis method carried the greatest overall effect on decomposition rate and vapor profile composition.Published by Elsevier B.V.

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Section: Discussionmentioning

confidence: 44%

“…al. had indicated that residual citric acid can destabilize HMTD [24]. It is presumed that formic acid would have a similar effect.…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Variation in the headspace of bulk hexamethylene triperoxide diamine (HMTD) with time, environment, and formulation

2017

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“…Most organic peroxide properties allow detection by GC analysis and ion mobility spectrometry (IMS) such as triacetone triperoxide (TATP) and benzoyl peroxide (BPO) [56,57,[71][72][73]. However, other peroxides, such as HMTD, are difficult to analyze through chromatographic methods due to their low vapor pressure and limited solubility [74][75][76][77].…”

Section: Detectionmentioning

confidence: 99%

Peroxide Based Organic Explosives

Türker

2021

EJCS

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In recent years progressively increasing terrorist activities, which use homemade explosives; such as acetone peroxide and other cyclic organic peroxides have led to worldwide awareness by security and defense agencies. Then the development of methodologies for the detection of cyclic organic peroxides have become an urgent need. Until quite recently, most of the current technology in use for trace detection of explosives had been unable to detect these energetic compounds. Differences in physical properties between cyclic organic peroxides is the main barrier for the development of a general method for analysis and detection of the peroxide explosives. In this short review, the most relevant contributions related to preparation, characterization and detection of the most important cyclic organic peroxides have been presented. It also includes few recent investigations about the toxicity and metabolism of some peroxide explosives.

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“…Most explosives teams within the United States train on peroxides provided by a single federal entity. The peroxide HMTD has been shown to have extremely variable odor profiles depending on synthesis and age (24,37). Yet, for safety purposes, a single, high purity synthesis route is followed for the creation of HMTD canine training aids.…”

Section: True Materialsmentioning

confidence: 99%

A Review of the Types of Training Aids Used for Canine Detection Training

Simon¹,

Lazarowski

Singletary

et al. 2020

Front. Vet. Sci.

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The canine detection community is a diverse one, ranging from scientific fields such as behavior, genetics, veterinary medicine, chemistry, and biology to applications in law enforcement, military, medicine, and agricultural/environmental detection. This diversity has allowed for a flourishing and innovative community, yet it has also led to little acceptance and agreement on terminology. This is especially true when discussing the variety of training aids used in olfactory-based exercises. In general, authentic materials and pseudo-scents are the most commonly discussed, with the former accepted widely for training and certification, and the latter more often disregarded. However, as advances are made in the creation of training materials, alternative training aids are being introduced that do not fit into either of these categories. The misconceptions surrounding how these alternative training aids are manufactured has led to confusion on their classification, and therefore their reliance as an effective tool. This manuscript will review the existing language surrounding canine training aids, address relevant research revealing effectiveness, and clarify the different types based on their manufacture, chemical nature, and fundamental function.

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Synthesis and Degradation of Hexamethylene Triperoxide Diamine (HMTD)

Cited by 24 publications

References 26 publications

Variation in the headspace of bulk hexamethylene triperoxide diamine (HMTD) with time, environment, and formulation

Variation in the headspace of bulk hexamethylene triperoxide diamine (HMTD) with time, environment, and formulation

Peroxide Based Organic Explosives

A Review of the Types of Training Aids Used for Canine Detection Training

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