Hydrotreatment is extensively used for the production of clean fuel. Attaining an understanding of the structural conversion of the nitrogen species during hydrotreatment is very challenging due to the compositional complexity and the absence of a proper characterization method. In the presented work, we coupled hydrogen/deuterium exchange (HDX) with positive-ion electrospray ionization high-resolution mass spectrometry ((+) ESI HR MS) to investigate the difference between the composition of the nitrogen-containing species and the functional groups before and after hydrotreatment. The solvent and additive were optimized for HDX (+) ESI HRMS through systematic evaluations on model nitrogen-containing compounds. We found that adding deuterated water (D₂O) and deuterated formic acid (DCOOD) significantly increased the degree of HDX and thus facilitated the identification of nitrogen functional groups. After application to the hydrotreated petroleum samples, the compositional variation of intermediate amine compounds during the heavy petroleum hydrotreatment process was clearly revealed.

中文翻译：

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使用氢/氘交换电喷雾电离高分辨率质谱法确定加氢处理石油分子中的氮官能团。

加氢处理被广泛用于生产清洁燃料。由于组成复杂且缺乏合适的表征方法，因此加氢处理过程中对氮物种结构转化的理解非常具有挑战性。在提出的工作中，我们将氢/氘交换（HDX）与阳离子电喷雾电离高分辨率质谱（（+）ESI HR MS）耦合，以研究含氮物质的组成与官能团之间的差异加氢处理前后。通过对模型含氮化合物进行系统评估，针对HDX（+）ESI HRMS优化了溶剂和添加剂。我们发现添加氘化水（D ₂O）和氘代甲酸（DCOOD）显着增加了HDX的程度，因此有助于鉴定氮官能团。应用于加氢处理的石油样品后，在重质石油加氢处理过程中，中间体胺化合物的组成变化清晰可见。