One-Step, Catalyst-Free Formation of Phenol from Benzoic Acid Using Water Microdroplets
Yifan Meng, Richard N. Zare, Elumalai Gnanamani
Abstract
Benzoic acid dissolved in water is electrosprayed (−4 kV) by using nitrogen gas at a pressure of 120 psi to form ∼10 μm diameter microdroplets. Analysis with mass spectrometry (MS) and tandem mass spectrometry (MS 2 ) of the resulting microdroplets shows the direct formation of phenol via decarboxylation without any catalyst or added reagents. This process represents an ecofriendly, environmentally benign method for producing phenol and related aromatic alcohols from their corresponding aromatic acids. The mechanism of this transformation was unambiguously characterized using mass spectrometry, radical trapping, and 18 O labeling.
Topics & Concepts
ChemistryDecarboxylationPhenolBenzoic acidCatalysisMass spectrometryReagentTandem mass spectrometryOrganic chemistryPhotochemistryChromatographyInnovative Microfluidic and Catalytic Techniques InnovationMass Spectrometry Techniques and ApplicationsAdvanced Chemical Sensor Technologies