Effect of the experimental conditions in the transformation of the bis-1,3-trichloromethylbenzene in the presence of HF and a Lewis acid

• Published in: Journal of molecular catalysis. A, Chemical Chemical, 2008-01, Vol.279 (1), p.119-127
• Main Authors: Salomé, J., Bachmann, C., De Oliveira-Vigier, K., Brunet, S., Lopez, J.
• Format: Article
• Language: English
• Subjects: 1,3-Trichloromethylbenzene; Antimony pentachloride; Catalysis; Chemical Sciences; Chemistry; Cl/F exchanges; DFT calculations; Exact sciences and technology; Fluorination; General and physical chemistry; Hydrogen fluoride; Lewis acid; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 1381-1169; 1873-314X
• DOI: 10.1016/j.molcata.2007.10.003

The transformation of the bis-1,3-trichloromethylbenzene depends on the experimental conditions (temperature, amount of HF and Lewis acid). The formation of the 1-trichloromethyl-3-trifluoromethylbenzene is favored in the presence of HF in default. The presence of a Lewis acid increases the formation of the more stable products at lower temperature. ▪ The transformation of the bis-1,3-trichloromethylbenzene depends on the experimental conditions (temperature, amount of HF and the presence of a Lewis acid). The formation of the 1-trichloromethyl-3-trifluoromethylbenzene is favored in the presence of HF in default. After the consumption of HF, the various fluorinated intermediates compounds were observed to lead to the more thermodynamically stable compounds, i.e., mainly the bis-1,3-trichloromethylbenzene and 1-trichloromethyl-3-trifluoromethylbenzene. These results were explained by theoretical calculations. The presence of a Lewis acid increases the formation of the more stable products at lower temperature. SbCl 5 is the most efficient catalyst corresponding to a decrease of 150 °C to obtain similar results compared with HF alone.