Reactions of Organic Peroxides with Alcohols in Atmospheric Pressure Chemical Ionization—the Pitfalls of Quantifying Triacetone Triperoxide (TATP)

Colizza, Kevin; Yevdokimov, Alexander; McLennan, Lindsay; Smith, James L.; Oxley, Jimmie C.

doi:10.1007/s13361-017-1836-3

Cited by 11 publications

(10 citation statements)

References 39 publications

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“…However, the composition of MEKPO remains an unresolved issue to this day, which requires further study. Colizza et al 35 (2018) claimed that since the MEKPO lacked any true 'standard', stability determinations or quantitative analysis of any specific species was not possible. There are only limited studies on the composition of MEKPO.…”

Section: Conversion Of Mek and H 2 O 2 Yield And Reaction Molementioning

confidence: 99%

“…Black et al 36 (2019) claimed that the MEKPO they prepared was confirmed by liquid chromatography-mass spectrometry (LCMS) analysis to contain the linear dimer, trimer, and tetramer as the major constituents, and also the cyclic trimer as a minor constituent. Colizza et al 35 (2018) claimed that there had been no definitive identification of the cyclic MEKPO species. They also provided possible evidence for the presence of the cyclic trimer.…”

Section: Conversion Of Mek and H 2 O 2 Yield And Reaction Molementioning

confidence: 99%

See 1 more Smart Citation

Efficient Continuous-Flow Synthesis of Methyl Ethyl Ketone Peroxide in a Microreaction System

Yang

Fang

Zhong

et al. 2022

Ind. Eng. Chem. Res.

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Organic peroxides are important to the fine chemical industry because of their applications in polymerization and curing initiators. However, as a hazardous process, the peroxidation reaction to synthesize organic peroxide involves explosive intermediates, sensitive products, and exothermic reactions, resulting in many accidents reported each year. Recently, continuous-flow microreaction synthesis has emerged as a new technology for producing chemicals efficiently and safely. This work introduced a novel efficient continuous-flow microreaction system to intensify the methyl ethyl ketone peroxide (MEKPO) production process. A microreaction platform for MEKPO synthesis was established, with quantitative methods to uncover the effects of reaction conditions on the kinetics and thermodynamics of the reaction, which had never been reported before. Then, a continuous-flow microreaction process was developed to replace the existing batch method by optimizing the peroxidation reaction, phase separation, and dilution steps. Compared to the current batch process for the commercial MEKPO product V688, the conversion of MEK and H 2 O 2 reached 69.11% (4% higher than V688) and 70.01%, respectively, when the nitric acid concentration in H 2 O 2 was 0.5 wt % and the reaction reach time was 270 s at a temperature of 25 °C. Also, our product can achieve the same performance (gel time and gel to cure time) as V688 with a lower active oxygen content (9.5% for V688, 8−9% for microreaction products). These results indicated that both the safety of the peroxidation reaction process and the activity of products were improved by replacing the existing batch process with our continuous microreaction process, which provides great potential for the industrial scale-up of such a system.

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Section: Conversion Of Mek and H 2 O 2 Yield And Reaction Molementioning

confidence: 99%

Section: Conversion Of Mek and H 2 O 2 Yield And Reaction Molementioning

confidence: 99%

Efficient Continuous-Flow Synthesis of Methyl Ethyl Ketone Peroxide in a Microreaction System

Yang

Fang

Zhong

et al. 2022

Ind. Eng. Chem. Res.

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“…In one of their works Oxley and coworkers considered quantification of organic peroxide explosives based on mass spectral analysis [92]. While for analytical purposes, fragments which are not fully characterized in terms of origin and intensity as a function of experimental conditions have been used, understanding the nature of those species is 186 very important.…”

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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“…8 Due to the thermal vaporization process and energetic plasma caused by corona discharge, various kinds of in-source reactions have been reported and attracted many chemists' attentions. K. Colizza et al 9 explored the formation mechanism of unusual fragments of organic peroxides during APCI process. For instance, they discussed the frequently observed fragment of triacetone triperoxide (TATP) at m/z 89 which was identified as the gas-phase reaction product of TATP with one or two methanol molecules/ions.…”

Section: ■ Introductionmentioning

confidence: 99%

Gas-Phase Alcoholysis of Benzylic Halides in the Atmospheric Pressure Ionization Source

Shen,

Chai,

Feng

et al. 2024

J. Am. Soc. Mass Spectrom.

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The present study investigates the gas-phase alcoholysis reaction of benzylic halides under atmospheric pressure chemical ionization (APCI) conditions. The APCI corona discharge is used to initiate the novel reaction, which is monitored by ion trap mass spectrometry (IT-MS). The model compound α,α,α-trifluorotoluene is applied to observe the cascade methoxylation reaction during the +APCI-MS analysis, resulting in the formation of [PhC(OCH 3 ) 2 ] + . Based on the results of isotopic labeling and substrate expansion experiments, an addition− elimination mechanism is proposed: initially, the reaction was initiated by the dissociation of fluorine from PhCF 3 under APCI condition, leading to the formation of [PhCF 2 ] + ; subsequently, two methanol molecules nucleophilicly attack [PhCF 2 ] + stepwisely, accompanied by the elimination of HF, yielding the product ion [PhC(OCH 3 ) 2 ] + . The proposed mechanism was further corroborated by theoretical calculations. The results of substrate scope expansion experiments suggest that this in-source reaction has the potential to differentiate the positional isomers of alcohols and phenols.

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Reactions of Organic Peroxides with Alcohols in Atmospheric Pressure Chemical Ionization—the Pitfalls of Quantifying Triacetone Triperoxide (TATP)

Cited by 11 publications

References 39 publications

Efficient Continuous-Flow Synthesis of Methyl Ethyl Ketone Peroxide in a Microreaction System

Efficient Continuous-Flow Synthesis of Methyl Ethyl Ketone Peroxide in a Microreaction System

Peroxide Based Organic Explosives

Gas-Phase Alcoholysis of Benzylic Halides in the Atmospheric Pressure Ionization Source

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