The reverse flotation of quartz and other gangue silicate minerals with alkyl amines is an important and well known strategy for the processing of iron ore, low grade bauxite ore, and phosphate rock. Some details of amine adsorption by quartz have been described in the literature, but little is known about the disposition of amine during bubble attachment. Now, a new experimental procedure involving vibrational sum frequency spectroscopy (VSFS) has been developed to provide, for the first time, a more detailed analysis of the state of dodecyl amine (DDA) adsorption at different interfaces during bubble attachment/detachment at a silica surface. The results show that the hydrophobic surface state at the silica surface is created by the transfer of a well-organized monolayer of DDA from the bubble surface to the silica surface during bubble contact and attachment.