New insight: Nitrosation of n-phenyl-β-naphthylamine in the early stage of nitroplasticizer aging

Chen, Kitmin; Kress, Joel D.; Yang, Dali

doi:10.1016/j.polymdegradstab.2023.110541

Polymer Degradation and Stability

2023

DOI: 10.1016/j.polymdegradstab.2023.110541

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New insight: Nitrosation of n-phenyl-β-naphthylamine in the early stage of nitroplasticizer aging

Kitmin Chen,

Joel D. Kress,

Dali Yang

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Cited by 3 publications

References 27 publications

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A new catalyst Cu(I)@TpFO-PA with high activities to C-N coupling reactions

Yu,

Tian,

et al. 2024

Applied Surface Science

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A new catalyst Cu(I)@TpFO-PA with high activities to C-N coupling reactions

Yu,

Tian,

et al. 2024

Applied Surface Science

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Recent progress in aging studies of a eutectic mixture of bis(2,2-dinitropropyl) acetal and formal nitroplasticizer

Yang,

Chen,

Edgar

et al. 2023

Polymer Degradation and Stability

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Tandem MS Elucidation of the Late-Stage Degradation Mechanism of Nitroplasticizer

Chen,

Yang

2024

ACS Omega

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Understanding the degradation behavior of nitroplasticizer (NP) and the subsequent production of nitro-organics is crucial for both environmental monitoring and material development. A nontargeted approach via LC-QTOF-MS was employed to thoroughly study the degradation mechanism of NP in its late aging stage. Both positive and negative modes of ESI were performed to increase the compound coverage. To shed light on the fragmentation behavior of NP degradants (e.g., compounds containing a high density of NO2 moieties and oxygen sites) in the positive mode, which is rarely reported, the high-resolution tandem MS information on precursor ions at m/z 251(+), 254(+), 266(+), and 270(+) and a pair of isomeric ions at m/z 284(+) was investigated to extract their common diagnostic ions and dissociation channels, including the neutral loss of 2,2-dinitropropanol, nitro-nitrite rearrangement, homolytic cleavage of NO2, and simple inductive cleavage. Additionally, leveraging the sensitivity for nitroaromatics in the negative polarity, negative ions m/z 182(−) and 233(−) are identified as dinitroaniline and dinitronaphthol, respectively, which confirm the secondary hydrolysis pathway of the antioxidant (e.g., N-phenyl-2-naphthylamine) postulated in our previous work. In addition to earlier findings, the detection of these eight degradants further supports the evidence of increased acid concentration and aging temperatures in the late-stage NP environment, which contribute to intricate degradation behaviors in different aging environments.

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New insight: Nitrosation of n-phenyl-β-naphthylamine in the early stage of nitroplasticizer aging

Cited by 3 publications

References 27 publications

A new catalyst Cu(I)@TpFO-PA with high activities to C-N coupling reactions

A new catalyst Cu(I)@TpFO-PA with high activities to C-N coupling reactions

Recent progress in aging studies of a eutectic mixture of bis(2,2-dinitropropyl) acetal and formal nitroplasticizer

Tandem MS Elucidation of the Late-Stage Degradation Mechanism of Nitroplasticizer

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