ie061386a_si_001.pdf (38.69 kB)
Self-Neutralizing in Situ Acid Catalysis for Single-Pot Synthesis of Iodobenzene and Methyl Yellow in CO2-Expanded Methanol
journal contribution
posted on 2007-08-01, 00:00 authored by Ross R. Weikel, Jason P. Hallett, Charles L. Liotta, Charles A. EckertDespite widespread use, homogeneous acid catalysis has the drawback of requiring downstream neutralization,
resulting in salt waste. Methylcarbonic acid is a self-neutralizing acid that forms in situ in methanol/CO2
systems at mild pressures (10−47 bar) and then decomposes by depressurization. In the work presented here,
methylcarbonic acid catalyzes the diazotization of aniline, which is either coupled with N,N-dimethyl aniline
to form methyl yellow or reacted with iodide to form iodobenzene. The syntheses of methyl yellow and
iodobenzene represent a class of industrially important reactions.