Akademik Veri Yönetim Sistemi
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, cilt.38, sa.10, ss.3838-3846, 1999 (SCI-Expanded)
Process conditions for the acid-catalyzed decomposition of 2-isopropylnaphthalene hydroperoxide (2-IPNHP) into 2-naphthol and acetone were investigated in the presence of acetic acid and H2O2 as the solvent and oxidizing reagent, respectively. 2-Naphthol and acetone are produced from 2-IPNHP by the ionic decomposition mechanism; however, reaction conditions that lead to the formation of radicals mainly favor the byproducts dimethyl-2-naphthylcarbinol (DMNC) and acetonaphthone (AN). The effects of the catalyst type and concentration on the 2-naphthol yield and on the product distribution were investigated by HClO4, H2SO4, H3PO4, and HCl. The catalytic activities of the acids in the decomposition of 2-IPNHP to produce 2-naphthol decreased in the order HClO4 > H2SO4 > HCl > H3PO4 depending on their acid strengths in acetic acid. The higher the catalyst concentration employed, the higher the 2-naphthol yield obtained. The high concentrations of 2-IPNHP did not lead to the hydroperoxide-induced decomposition reactions; instead they increased the ionic decomposition rate due to the polar character of 2-IPNHP. The increase in the DMNC concentration in the decomposition medium slightly decreased the a-naphthol production rate and yield. The increase in temperature in the range of 22-40 degrees C increased the 2-naphthol production. The process conditions such as law acid strength, low catalyst concentration, and high temperature that lead to radical reactions increased the production of AN. The other byproduct DMNC was also oxidized to 2-IPNHP with H2O2 in the reactor. A 61% yield of 2-naphthol was obtained under the batch reactor conditions of 0.114 mol dm(-3) HClO4 and 1.036 mol dm(-3) initial 2-IPNHP concentrations at 22 degrees C.