Mechanistic Rationale for Ketene Formation during Dabbing and Vaping

Munger, Kaelas R.; Anreise, Killian M.; Jensen, Robert P.; Peyton, David H.; Strongin, Robert M.

doi:10.1021/jacsau.4c00436

Cited by 1 publication

(2 citation statements)

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“…Also of significant concern is the sustained nonlethal ketene exposure affecting larger numbers of people as the longer-term health impacts of this remain unknown. Employing deuterated isotopically labeled CBN-OAc-D 3 , Strongin et al unambiguously reconfirmed that the acetate moiety is the ketene source. Since VEA had the acetate moiety, while VE did not, when the vaping solution was switched from VEA to VE, our results (Figure ) showed that no ketene was detected within experimental error, confirming that the acetate moiety of VEA was the ketene source.…”

Section: Discussionmentioning

confidence: 99%

“…Importantly as many vaping flavor chemicals contain ester functional groups, their thermal decomposition temperatures are dependent upon individual ester chemical structures and their individual thermal degradation chemistries . Although the uncatalyzed gas-phase thermal degradation of phenyl acetate forming phenol and ketene occurs between 650–850 °C under real-world vaping conditions, ketene was detectable upon vaping CBN-acetates even as low as 278 °C using a dab platform, where ambient O 2 significantly promoted the ketene generation . Canchola et al reported that the presence of O 2 significantly enhances the degradation of VEA at both high (356 °C) and low (176 °C) temperatures, resulting in the formation of numerous degradation products previously identified in VEA vaping emissions.…”

Section: Discussionmentioning

confidence: 99%

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Conditions Leading to Ketene Formation in Vaping Devices and Implications for Public Health

Wang,

Jacob,

Wang

et al. 2024

Chem. Res. Toxicol.

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The outbreak of e-cigarette or vaping use-associated lung injury (EVALI) in the United States in 2019 led to a total of 2807 hospitalizations with 68 deaths. While the exact causes of this vaping-related lung illness are still being debated, laboratory analyses of products from victims of EVALI have shown that vitamin E acetate (VEA), an additive in some tetrahydrocannabinol (THC)containing products, is strongly linked to the EVALI outbreak. Because of its similar appearance and viscosity to pure THC oil, VEA was used as a diluent agent in cannabis oils in illicit markets. A potential mechanism for EVALI may involve VEA's thermal decomposition product, ketene, a highly poisonous gas, being generated under vaping conditions. In this study, a novel approach was developed to evaluate ketene production from VEA vaping under measurable temperature conditions in real-world devices. Ketene in generated aerosols was captured by two different chemical agents and analyzed by gas chromatography−mass spectrometry (GC-MS) and liquid chromatography with tandem mass spectrometry (LC-MS/MS). The LC-MS/MS method takes advantage of the high sensitivity and specificity of tandem mass spectrometry and appears to be more suitable than GC-MS for the analysis of large batches of samples. Our results confirmed the formation of ketene when VEA was vaped. The production of ketene increased with repeat puffs and showed a correlation to temperatures (200 to 500 °C) measured within vaping devices. Device battery power strength, which affects the heating temperature, plays an important role in ketene formation. In addition to ketene, the organic oxidant duroquinone was also obtained as another thermal degradation product of VEA. Ketene was not detected when vitamin E was vaped under the same conditions, confirming the importance of the acetate group for its generation.

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Section: Discussionmentioning

confidence: 99%