Journal of the Japan Petroleum Institute
Online ISSN : 1349-273X
Print ISSN : 1346-8804
ISSN-L : 1346-8804
Regular Paper
Differences in Catalytic Activity and Durability of Nitrogen Sites on Nitrided SBA-15 or Porous Carbon Nitride
Aisa KAWANOTakahiko MOTEKIMasaru OGURA
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Supplementary material

2022 Volume 65 Issue 3 Pages 116-124

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Abstract

Nitrided SBA-15 (NSBA-15) is a solid base catalyst for several reactions, in which the basicity arises from a lone pair on a nitrogen atom substituted in the silicate framework. Porous carbon nitride (PCN) formed on a SBA-15 template is also a solid base catalyst with a nitrogen atom as the active site. In this study, the catalytic activity and durability of nitrogen atoms in nitrided mesoporous silica and porous carbon nitride were compared to evaluate the origin of basicity by using the Knoevenagel condensation of benzaldehyde with active methylene compounds. With malononitrile (pKa of 11.1) as the methylene compound, both NSBA-15 and PCN showed a high product yield. Using ethyl cyanoacetate (pKa of 13.1), only NSBA-15 catalyzed the reaction, probably because the active site of NSBA-15 is a quasi-aliphatic amine and that of PCN is an aromatic amine. On the other hand, PCN showed high durability as the content of nitrogen was not decreased by the catalytic reaction and long-term storage, whereas the Si–N bond in NSBA-15 easily underwent hydrolysis.

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