Ball-milled hexagonal boron nitride was investigated as a solid base catalyst. The ball-milled boron nitrides were heated in a vacuum or air and used for Knoevenagel condensation. Measurements by X-ray diffraction, nitrogen adsorption, thermogravimetry-mass spectrometry, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy indicated that the heat treatment under vacuum hardly changed the physicochemical properties including crystal structure and surface composition whereas the heat treatment in air significantly altered the properties due to the formation of B2O3. The number of basic sites increased with the increase of the evacuation temperature. The boron nitrides after evacuation gave moderate product yield for Knoevenagel condensation of benzaldehyde with malononitrile at 40 °C. The boron nitrides after calcination showed different activity, dependent on the calcination temperature. The boron nitride after ball-milling, followed by calcination at 300 °C exhibited the highest activity. The catalytic activity was not directly related to the base amount and the surface areas, suggesting that acid-base bifunctionality plays an important role in Knoevenagel condensation using the ball-milled boron nitride catalysts.
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