Synthesis of Resorcinol and Chlorophenol from Irradiation of 1,3-Dichlorobenzene in a Water Ice Environment by Low-Energy Electrons.

Dichlorobenzene is beneficial to industries, however, the release of this compound into the environment causes significant damage to ecosystems and human health, as it exhibits resistance to biodegradation. Here, we show that chlorophenol and resorcinol are synthesized from 1,3-dichlorobenzene in a water ice environment (1) directly on a poly-crystalline gold surface and (2) after low-energy (<12 eV) electron irradiation of admixture films. For the latter, at energies below 5.5 eV, the electrons solely decompose the chlorinated compound into radicals that further undergo reaction with surrounding water molecules. At higher energies (i.e., >5.5 eV) additional fragments, e.g., hydroxyl radicals, produced from the dissociation of water molecules, may also be involved in the chemistry. The present results may suggest strategies for potential eco-friendly, sustainable, and scalable processes for the mitigation of these halogenated compounds such as cold plasma and radiation, in which low-energy (<10 eV) electrons are predominantly produced.