Atmospheric Chemistry of 2-Amino-2-methyl-1-propanol: A Theoretical and Experimental Study of the OH-Initiated Degradation under Simulated Atmospheric Conditions

Tan, Wen; Zhu, Liang; Mikoviny, Tomáš; Nielsen, Claus J.; Tang, Yizhen; Wisthaler, Armin; Eichler, Philipp; Müller, Markus; D’Anna, Barbara; Farren, Naomi J.; Hamilton, Jacqueline F.; Pettersson, Jan B. C.; Hallquist, Mattias; Antonsen, Simen Gjelseth; Stenstrøm, Yngve

doi:10.1021/acs.jpca.1c04898

Cited by 6 publications

(6 citation statements)

References 76 publications

(131 reference statements)

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“…Imines have been detected as major products in the atmospheric gas phase photo-oxidation of amines, − with N -methylmethanimine (CH 3 NCH 2 , MMI) accounting for around 70% of the products formed in dimethylamine and 50% in trimethylamine photo-oxidation . Amines are normally found in the low ppbv-range in the natural atmosphere, with methylamine, dimethylamine, and trimethylamine being among the most abundant .…”

Section: Introductionmentioning

confidence: 99%

Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study

et al. 2022

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The OH-initiated photo-oxidation of N -methylmethanimine, CH 3 N=CH 2 , was investigated in the 200 m 3 EUPHORE atmospheric simulation chamber and in a 240 L stainless steel photochemical reactor employing time-resolved online FTIR and high-resolution PTR-ToF-MS instrumentation and in theoretical calculations based on quantum chemistry results and master equation modeling of the pivotal reaction steps. The quantum chemistry calculations forecast the OH reaction to primarily proceed via H-abstraction from the =CH 2 group and π-system C-addition, whereas H-abstraction from the −CH 3 group is a minor route and forecast that N-addition can be disregarded under atmospheric conditions. Theoretical studies of CH 3 N=CH 2 photolysis and the CH 3 N=CH 2 + O 3 reaction show that these removal processes are too slow to be important in the troposphere. A detailed mechanism for OH-initiated atmospheric degradation of CH 3 N=CH 2 was obtained as part of the theoretical study. The photo-oxidation experiments, obstructed in part by the CH 3 N=CH 2 monomer–trimer equilibrium, surface reactions, and particle formation, find CH 2 =NCHO and CH 3 N=CHOH/CH 2 =NCH 2 OH as the major primary products in a ratio 18:82 ± 3 (3σ-limit). Alignment of the theoretical results to the experimental product distribution results in a rate coefficient, showing a minor pressure dependency under tropospheric conditions and that can be parametrized k ( T ) = 5.70 × 10 –14 × ( T /298 K) 3.18 × exp(1245 K/ T ) cm 3 molecule –1 s –1 with k 298 = 3.7 × 10 –12 cm 3 molecule –1 s –1 . The atmospheric fate of CH 3 N=CH 2 is discussed, and it is concluded that, on a global scale, hydrolysis in the atmospheric aqueous phase to give CH 3 NH 2 + CH 2 O will constitute a dominant loss process. N 2 O will not be formed in the atmospheric gas phase degradation, and there are no indications of nitrosamines and nitramines formed as primary products.

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Section: Introductionmentioning

confidence: 99%

Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study

et al. 2022

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“…We attribute this mis-match to evaporation of particles in the heated sampling lines and, in particular, in the drift tube of the PTR-MS analyzer . A more pronounced example of particle evaporation in the PTR-MS analyzer was reported in AMP (2-amino-2-methyl-1-propanol) photo-oxidation experiments . Also, the (noisy) PIP-NO profile displays a time profile in the later part of the experiment, which conflicts the established gas phase chemistry of amines …”

Section: Resultsmentioning

confidence: 82%

“…105 A more pronounced example of particle evaporation in the PTR-MS analyzer was reported in AMP (2-amino-2-methyl-1-propanol) photo-oxidation experiments. 106 Also, the (noisy) PIP-NO profile displays a time profile in the later part of the experiment, which conflicts the established gas phase chemistry of amines. 20 Considering the inherent uncertainties in the monitor values for NO, NO 2 , and j NOd 2 , and in the derived volume mixing ratios from PTR measurements, the span in the extracted branching is remarkably modest, and the average results, k N−H / k tot = 0.38 ± 0.08 and k C 2 −H /k tot = 0.49 ± 0.19, are in disturbing agreement with the theoretical predictions abstaining us from drawing firm conclusions.…”

Section: The Journal Of Physical Chemistry Amentioning

confidence: 99%

Experimental and Theoretical Study of the OH-Initiated Degradation of Piperidine under Simulated Atmospheric Conditions

Tan,

Zhu,

Mikoviny

et al. 2024

J. Phys. Chem. A

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The OH-initiated photo-oxidation of piperidine and the photolysis of 1-nitrosopiperidine were investigated in a large atmospheric simulation chamber and in theoretical calculations based on CCSD(T*)-F12a/aug-cc-pVTZ//M062X/ aug-cc-pVTZ quantum chemistry results and master equation modeling of the pivotal reaction steps. The rate coefficient for the reaction of piperidine with OH radicals was determined by the relative rate method to be k OH-piperidine = (1.19 ± 0.27) × 10 −10 cm 3 molecule −1 s −1 at 304 ± 2 K and 1014 ± 2 hPa. Product studies show the piperidine + OH reaction to proceed via H-abstraction from both CH 2 and NH groups, resulting in the formation of the corresponding imine (2,3,4,5tetrahydropyridine) as the major product and in the nitramine (1-nitropiperidine) and nitrosamine (1-nitrosopiperidine) as minor products. Analysis of 1-nitrosopiperidine photolysis experiments under natural sunlight conditions gave the relative rates j rel = j 1-nitrosoperidine /j NOd 2 = 0.342 ± 0.007, k 3 /k 4a = 0.53 ± 0.05 and k 2 / k 4a = (7.66 ± 0.18) × 10 −8 that were subsequently employed in modeling the piperidine photo-oxidation experiments, from which the initial branchings between H-abstraction from the NH and CH 2 groups, k N−H /k tot = 0.38 ± 0.08 and k C 2 −H /k tot = 0.49 ± 0.19, were derived. All photo-oxidation experiments were accompanied by particle formation that was initiated by the acid−base reaction of piperidine with nitric acid. Primary photo-oxidation products including both 1-nitrosopiperidine and 1-nitropiperidine were detected in the particles formed. Quantum chemistry calculations on the OH initiated atmospheric photo-oxidation of piperidine suggest the branching in the initial H-abstraction routes to be ∼35% N 1 , ∼50% C 2 , ∼13% C 3 , and ∼2% C 4 . The theoretical study produced an atmospheric photo-oxidation mechanism, according to which H-abstraction from the C 2 position predominantly leads to 2,3,4,5-tetrahydropyridine and H-abstraction from the C 3 position results in ring opening followed by a complex autoxidation, of which the first few steps are mapped in detail. H-abstraction from the C 4 position is shown to result mainly in the formation of piperidin-4-one and 2,3,4,5-tetrahydropyridin-4-ol, whereas H-abstraction from N 1 under atmospheric conditions primarily leads to 2,3,4,5-tetrahydropyridine and in minor amounts of 1-nitrosopiperidine and 1-nitropiperidine. The calculated rate coefficient for the piperidine + OH reaction agrees with the experimental value within 35%, and aligning the theoretical numbers to the experimental value results in k(T) = 2.46 × 10 −12 × exp(486 K/T) cm 3 molecule −1 s −1 (200−400 K).

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“…We used an extended classical GSEA with a large-scale GWAS aggregate dataset to detect the associations between environmental chemical substances and JIA and identified 281 chemical substances, including drugs, organic compounds, inorganic compounds, plants extracts, nutrients, phenols, air pollutants, and heavy metals. As a common component used in many consumer products, 2-amino-2-methyl-1-propanol is a promising amine for use in industrial-scale post-combustion CO, as well as being an atmospheric pollutant [ 48 ]. Yavorskyy et al detected high levels of 2-amino-2-methyl-1-propanol in the synovial fluid of osteoarthritic knees [ 49 ]; thus, it may be related to the onset of joint inflammation to some extent, corroborating our findings.…”

Section: Discussionmentioning

confidence: 99%

Identification of candidate genes and pathways associated with juvenile idiopathic arthritis by integrative transcriptome-wide association studies and mRNA expression profiles

Feng

Chen

et al. 2023

Arthritis Res Ther

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Aim Juvenile idiopathic arthritis (JIA) is the most common chronic rheumatic disease of childhood, with genetic susceptibility and pathological processes such as autoimmunity and autoinflammation, but its pathogenesis is unclear. We conducted a transcriptome-wide association study (TWAS) using expression interpolation from a large-scale genome-wide association study (GWAS) dataset to identify genes, biological pathways, and environmental chemicals associated with JIA. Methods We obtained published GWAS data on JIA for TWAS and used mRNA expression profiling to validate the genes identified by TWAS. Gene Ontology (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) pathway enrichment analyses were performed. A protein–protein interaction (PPI) network was generated, and central genes were obtained using Molecular Complex Detection (MCODE). Finally, chemical gene expression datasets were obtained from the Comparative Toxicogenomics database for chemical genome enrichment analysis. Results TWAS identified 1481 genes associated with JIA, and 154 differentially expressed genes were identified based on mRNA expression profiles. After comparing the results of TWAS and mRNA expression profiles, we obtained eight overlapping genes. GO and KEGG enrichment analyses of the genes identified by TWAS yielded 163 pathways, and PPI network analysis as well as MCODE resolution identified a total of eight clusters. Through chemical gene set enrichment analysis, 287 environmental chemicals associated with JIA were identified. Conclusion By integrating TWAS and mRNA expression profiles, genes, biological pathways, and environmental chemicals associated with JIA were identified. Our findings provide new insights into the pathogenesis of JIA, including candidate genetic and environmental factors contributing to its onset and progression.

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Atmospheric Chemistry of 2-Amino-2-methyl-1-propanol: A Theoretical and Experimental Study of the OH-Initiated Degradation under Simulated Atmospheric Conditions

Cited by 6 publications

References 76 publications

Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study

Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study

Experimental and Theoretical Study of the OH-Initiated Degradation of Piperidine under Simulated Atmospheric Conditions

Identification of candidate genes and pathways associated with juvenile idiopathic arthritis by integrative transcriptome-wide association studies and mRNA expression profiles

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Atmospheric Chemistry of 2-Amino-2-methyl-1-propanol: A Theoretical and Experimental Study of the OH-Initiated Degradation under Simulated Atmospheric Conditions

Cited by 6 publications

References 76 publications

Atmospheric Chemistry of N-Methylmethanimine (CH3N═CH2): A Theoretical and Experimental Study

Atmospheric Chemistry of N-Methylmethanimine (CH3N═CH2): A Theoretical and Experimental Study

Experimental and Theoretical Study of the OH-Initiated Degradation of Piperidine under Simulated Atmospheric Conditions

Identification of candidate genes and pathways associated with juvenile idiopathic arthritis by integrative transcriptome-wide association studies and mRNA expression profiles

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Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study

Atmospheric Chemistry of N-Methylmethanimine (CH₃N═CH₂): A Theoretical and Experimental Study