Alkaline Condensation of Benzotrichloride with 4-Alkylphenols as the Synthesis Method of Copper Extractants

• Published in: Industrial & engineering chemistry research 1996-02, Vol.35 (2), p.422-429
• Main Authors: Olszanowski, Andrzej, Błaszczak, Jan, Szymanowski, Jan
• Format: Article
• Language: English
• Subjects: Applied sciences; Chemical industry and chemicals; Exact sciences and technology; Industrial chemicals; Organic industry
• ISSN: 0888-5885; 1520-5045
• DOI: 10.1021/ie950080t

Alkaline condensation of benzotrichloride with alkylphenols and phenol chloro and bromo derivatives is studied. The effects of reaction conditions upon the process course and the product composition and scale-up are determined. Condensation with hydrophobic alkylphenols containing at least four carbon atoms in the alkyl group gives high quality 2-hydroxy-5-alkylbenzophenones, and the method is useful for synthesis of these reagents. Scale-up may be successfully carried out by the recirculation of the well-dispersed reaction mixture. Different reaction courses observed for hydrophilic and hydrophobic alkylphenols may be explained by the adsorption of hydrophilic alkylphenolates at the interfacial surface area that favors the C-acylation of the alkylphenol. 2-Hydroxy-5-alkylbenzophenones synthesized via alkaline condensation are suitable intermediates to obtain copper extractants that have a good extraction performance. Condensation of benzotrichloride with halogen derivatives of phenol having chloride and bromine at the 4-position gives atypical products with elimination of halogen and acylation of phenol derivatives at the 4-position.