Recyclable Nonionic–Anionic Bola Surfactant as a Stabilizer of Size-Controllable and pH-Responsive Pickering Emulsions

A novel nonionic–anionic Bola surfactant (abbreviated as CH 3 O(EO) 7 -R 11 -COOH) was designed and synthesized by condensation of methyl polyoxyethylene (7) ether with 12-bromododecanoic acid. In neutral aqueous solution, the surfactant behaves as a nonionic one and can stabilize oil-in-water (O/W) conventional emulsions alone and costabilize O/W Pickering emulsions with positively charged alumina nanoparticles with n -decane as the oil. In alkaline solution, the carboxylic acid group is deprotonated, becoming anionic and the surfactant is converted to Bola form, which is an inferior emulsifier and does not adsorb on particle surfaces, resulting in demulsification of both kinds of emulsions. With strong hydrophilicity, both the Bola surfactant and the bare particles return to the aqueous phase after demulsification, which is therefore recyclable and reusable in accordance with sustainable chemistry and engineering. In acidic media between pH 3 and 6, the ethyleneoxy groups tend to desorb from particle surfaces, slightly reducing the hydrophobicity of the particles. However, Pickering emulsions are still stable but their droplet size increases on lowering the pH. The Pickering emulsions are therefore pH-responsive and size-controllable. This newly designed Bola surfactant is effective in preparing smart emulsions, which are extensively applied in heterogeneous catalysis, oil product transportation, emulsion polymerization, and new material preparation.