Green and Sustainable Chemistry

Volume 1, Issue 4 (November 2011)

ISSN Print: 2160-6951   ISSN Online: 2160-696X

Google-based Impact Factor: 3.35  Citations  

Halogen Exchange in Near-Critical Water

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DOI: 10.4236/gsc.2011.14021    4,656 Downloads   8,408 Views  

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ABSTRACT

Bromoaromatics are ubiquitous in chemistry, and their manufacture is often wasteful. Halogen exchange under hydrothermal conditions constitutes a viable alternative for their synthesis in some cases. The prepara-tion of 1,2-dibromobenzene and 1-bromo-2-chlorobenzene from 1,2-dichlorobenzene, by treatment with hy-drobromic acid in hydrothermal media at temperatures ranging from 240?C to 320?C was investigated as a viable alternative to de novo synthesis. The effects of temperature, exchange duration and the presence of Fe3+ salts on product yields are discussed. Yields for both targeted haloarenes of up to 37% and 48%, respec-tively, were achieved, with very limited formation of 1,3- and 1,4-dihalobenzene isomers. A mechanism for halogen exchange was proposed.

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A. Alhazmi, P. Alburquerque and T. Junk, "Halogen Exchange in Near-Critical Water," Green and Sustainable Chemistry, Vol. 1 No. 4, 2011, pp. 128-131. doi: 10.4236/gsc.2011.14021.

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