FSC 432
Petroleum Processing

Hydrodenitrogenation

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Hydrodenitrogenation

Hydrodenitrogenation (HDN) is a similar process to HDS in which hydrogen is used to remove nitrogen, and for this reason during HDS the nitrogen content of fuels is also reduced. Figure 9.6 shows different types of nitrogen-containing compounds in crude oil and refinery unit products. In addition to reducing the N content in fuels as a finishing process, basic nitrogen compounds such as pyridine and quinoline shown in Figure 9.6 should also be removed as a pretreatment step to protect the acidic catalysts used in processes such as FCC. This is similar to HDS being an important pretreatment process for feedstocks that would be exposed to noble metal catalysts (such as Pt in catalytic reforming process) that are poisoned by sulfur compounds. Figure 9.7 shows examples of HDN reactions and catalysts used for HDN. Similar to HDN reactions for quinoline, shown in Figure 9.7, pyridine (C5H5N) can be reduced to pentane (C5H12) and ammonia (NH3) by adding 5 molesH2 in three steps. The overall HDN reaction for pyridine is C5H5N + 5H2 → C5H12 + NH3.

Basic nitrogen compounds- poison acidic catalysts: 6-membered rings (pyridine), Amines (R-NH2), Neutral or acidic (pyrol, indole, carbazole)
Figure 9.6. Types of nitrogen containing compounds found in crude oil.
Source: Dr. Semih Eser
Quinoline + lots of H2 (and catalyst) becomes propyl benzene and NH3. More info on the general process above. Catalyst: Mo (or W)/Al2O3/Ni
Figure 9.7. HDN reactions and catalysts.
Source: Dr. Semih Eser