Hydrazoic Acid and Azides

Jobelius, Horst H.; Scharff, Hans-Dieter

doi:10.1002/14356007.a13_193

Cited by 5 publications

(4 citation statements)

References 9 publications

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“…All articles describing human azide exposure were included. Reports of physical trauma due to airbag deployment alone were excluded as were articles on azides other than sodium, since NaN 3 is the principal azide species produced and it is available for purchase online [ 2 , 20 , 21 ]. Finally, we excluded articles that were duplicated cases, had insufficient data, or irrelevant account, such as no discussion of human azide poisoning.…”

Section: Methodsmentioning

confidence: 99%

Sodium azide poisoning: a narrative review

Tat

Heskett

Satomi

et al. 2021

Clinical Toxicology

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Context: Sodium azide is a highly toxic chemical. Its production has increased dramatically over the last 30 years due to its widespread use in vehicular airbags, and it is available for purchase online. Thus, accidental exposure to azide or use as a homicidal or suicidal agent could be on the rise, and secondary exposure to medical personnel can occur. No antidote exists for azide poisoning. We conducted a systematic review of azide poisoning to assess recent poisoning reports, exposure scenarios, clinical presentations, and treatment strategies. Methods: We searched both medical and newspaper databases to review the literature between 01/ 01/2000 and 12/31/2020, pairing the controlled vocabulary and keyword terms "sodium azide" or "hydrazoic acid" with terms relating to exposures and outcomes, such as "ingestion," "inhalation," "exposure," "poisoning," and "death." We included all peer-reviewed papers and news articles describing human azide poisoning cases from English and non-English publications that could be identified using English keywords. Data abstracted included the number, age, and gender of cases, mode of exposure, exposure setting, azide dose and route of exposure, symptoms, outcome, and treatment modalities. Results: We identified 663 peer-reviewed papers and 303 newspaper articles. After removing duplicated and non-qualifying sources, 54 publications were reviewed describing 156 cases, yielding an average of 7.8 reported azide poisoning cases per year. This rate is three times higher than in a previous review covering the period of 1927 to 1999. Poisoning occurred most commonly in laboratory workers, during secondary exposure of medical personnel, or from a ripped airbag. Hypotension occurred commonly, in some cases requiring vasopressors and one patient received an intra-aortic ballon pump. Gastric lavage and/or activated charcoal were used for oral azide ingestion, and sodium nitrite, sodium thiosulfate, and/or hydroxocobalamin were used in severely poisoned patients. Conclusions: Recent increases in azide poisoning reports may stem from greater commercial use and availability. Treatment of systemic poisoning may require aggressive hemodynamic support due to profound hypotension. Based on mechanistic considerations, hydroxocobalamin is a rational choice for treating azide poisoning.

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Section: Methodsmentioning

confidence: 99%

Sodium azide poisoning: a narrative review

Tat

Heskett

Satomi

et al. 2021

Clinical Toxicology

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“…Considering the scaled-up synthesis of edoxaban based on Daiichi-Sankyo's original synthetic route (Scheme 1), the largest challenge is the azide group introduction step, more specifically, safety concerns and the suppression of undesired diastereomer generation. The requisite nucleophile, sodium azide, is highly explosive and toxic, 6 and hence storing and handling large quantities of this material is a safety and regulatory hurdle. Differential scanning calorimetry (DSC) measurements of the azide intermediate 7 showed that the exothermic starting temperature was 220 °C (Figure S1).…”

Section: ■ Introductionmentioning

confidence: 99%

“…The requisite nucleophile, sodium azide, is highly explosive and toxic, and hence storing and handling large quantities of this material is a safety and regulatory hurdle. Differential scanning calorimetry (DSC) measurements of the azide intermediate 7 showed that the exothermic starting temperature was 220 °C (Figure S1).…”

Section: Introductionmentioning

confidence: 99%

Stereoinvertive Deoxyamination of trans-2-Aminocyclohexanol Using Bose–Mitsunobu Azidation and Staudinger Reaction for the Stereoselective Synthesis of Edoxaban

Ochiai,

Kubota,

Sasagawa

et al. 2023

Org. Process Res. Dev.

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Stereoinvertive deoxyamination involving Bose−Mitsunobu azidation and the Staudinger reaction, which proceeds under mild conditions in the presence of a neighboring group, was successfully applied for the synthesis of edoxaban. The one-pot process allowed access to key intermediates of edoxaban without isolating azide intermediates. Furthermore, the efficiency of the Bose−Mitsunobu azidation was dramatically improved by changing the substituent on the neighboring group from the Boc group to a thiazole carbonyl unit.

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“…Accounting for correction factors, the total cooling load requirement translates to 2.87 kW h/kg and total heating load requirement translates to 2.60 MJ/kg (0.0602 m 3 of natural gas per kg of sodium azide). In the next step sodium azide (solid phase) is reacted with hydrochloric acid (liquid phase) at 65 °C, to produce hydrazoic acid (HN 3 ) and sodium chloride salt . Since one of the products is a gas and the other a solid, the two phases can be separated through a one step flash drum.…”

Section: Introductionmentioning

confidence: 99%

Energetic Ionic Materials: How Green Are They? A Comparative Life Cycle Assessment Study

Mehrkesh

Karunanithi

2013

ACS Sustainable Chem. Eng.

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Recently, several energetic ionic salts and liquids have been proposed as novel high-energy materials, propellants, and explosives. The life cycle environmental impacts of these new energetic salts have not been previously studied. Environmental impacts arise both from release of these energetic materials themselves as well as from their synthesis. In this work, for the first time, we report the results of cradle-to-gate life cycle environmental impacts of production of energetic ionic salt 1,2,3-triazolium nitrate and compare it with traditional energetic material 2,4,6-trinitrotoluene (TNT). The results indicate that the production processes of ionic salt have a significantly higher environmental footprint than conventional energetic materials. The above result was consistent across all nine impact categories analyzed and can be directly attributed to energy intensive steps needed to prepare the ionic salt and its precursors. The findings suggest that ionic energetic materials have higher environmental impact than TNT from a life cycle perspective.

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Hydrazoic Acid and Azides

Cited by 5 publications

References 9 publications

Sodium azide poisoning: a narrative review

Sodium azide poisoning: a narrative review

Stereoinvertive Deoxyamination of trans-2-Aminocyclohexanol Using Bose–Mitsunobu Azidation and Staudinger Reaction for the Stereoselective Synthesis of Edoxaban

Energetic Ionic Materials: How Green Are They? A Comparative Life Cycle Assessment Study

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