1,3,5‐Trichloro‐2,4,6‐Trinitrobenzene: The Elusive Impurity Standard,Propellants, Explosives, Pyrotechnics

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1,3,5‐Trichloro‐2,4,6‐Trinitrobenzene: The Elusive Impurity Standard
Propellants, Explosives, Pyrotechnics ( IF 1.7 ) Pub Date : 2021-02-07 , DOI: 10.1002/prep.202000223
Kristin Kelly ₁ , Geoff Brown ₁

Affiliation

1,3,5‐triamino‐2,4,6‐trinitrobenzene (TATB) is an insensitive high explosive synthesized in two steps; 1,3,5‐trichloro‐2,4,6‐trinitrobenzene (TCTNB) is the only intermediate. Due to solubility limitations, TATB is often dissolved in dimethylsulfoxide (DMSO) for liquid chromatography‐mass spectrometry (LC–MS) analyses; however, DMSO is capable of participating in a wide variety of reactions. Intending to use it as an impurity standard, TCTNB was dissolved in DMSO. A stark color change from colorless to yellow accompanied by wavelength and ion chromatogram changes occurred over 24 hours. Three compounds were identified as causing the color change. All three were present in both acetone and DMSO solutions, but, overtime the absorbance spectra of the DMSO solution changed indicating an underlying reaction occurs between these compounds and DMSO. The chemical formulas of impurities present in the TCTNB sample as well as reaction products are identified via quadrupole time of flight mass spectrometry. The chemical structures are also proposed. The combination of the solvent system, ionization technique, and halogenated/nitrated aromatic ring structures resulted in substitutions of both the chlorine and nitro groups to hydroxyl groups. Three proposed structures were closely related to TCTNB, but only one was detected at a consistent mass and absorbance wavelength in both acetone and DMSO. This compound had undergone a chlorine to hydroxyl substitution and should be utilized for TCTNB detection.

中文翻译：

1,3,5-三氯-2,4,6-三硝基苯：难以捉摸的杂质标准

1,3,5-三氨基-2,4,6-三硝基苯（TATB）是一种不敏感的高爆炸药，可分两步合成。1,3,5-三氯-2-2,4,6-三硝基苯（TCTNB）是唯一的中间体。由于溶解度的限制，TATB通常溶解在二甲基亚砜（DMSO）中，以进行液相色谱-质谱（LC-MS）分析。但是，DMSO能够参与各种各样的反应。为了将其用作杂质标准品，将TCTNB溶解在DMSO中。在24小时内，颜色发生了从无色到黄色的鲜明变化，并伴随着波长和离子色谱图的变化。鉴定出三种化合物引起颜色变化。丙酮和DMSO溶液中都存在这三种化合物，但是随着时间的流逝，DMSO溶液的吸收光谱发生了变化，表明这些化合物和DMSO之间发生了潜在的反应。通过四极杆飞行时间质谱法鉴定TCTNB样品中存在的杂质以及反应产物的化学式。还提出了化学结构。溶剂系统，电离技术和卤化/硝化的芳环结构的结合导致氯和硝基均被羟基取代。提出的三种结构与TCTNB密切相关，但是在丙酮和DMSO中，只有一种在质量和吸收波长一致的情况下被检测到。该化合物已被氯取代为羟基，应用于TCTNB检测。溶剂系统，电离技术和卤化/硝化的芳环结构的结合导致氯和硝基均被羟基取代。提出的三种结构与TCTNB密切相关，但是在丙酮和DMSO中，只有一种在质量和吸收波长一致的情况下被检测到。该化合物已被氯取代为羟基，应用于TCTNB检测。溶剂系统，电离技术和卤化/硝化的芳环结构的结合导致氯和硝基均被羟基取代。提出的三种结构与TCTNB密切相关，但是在丙酮和DMSO中，只有一种在质量和吸收波长一致的情况下被检测到。该化合物已被氯取代为羟基，应用于TCTNB检测。

更新日期：2021-03-31

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