Decomposition of 2-isopropylnaphthalenehydroperoxide into 2-naphthol and acetone: reactor operation parameters

• Published in: Applied catalysis. A, General General, 2003-01, Vol.238 (1), p.85-97
• Main Authors: BOYACI, Fatma Gül, TAKAC, Serpil, CALIK, Güzide, ÖZDAMAR, Tuner H
• Format: Article
• Language: English
• Subjects: 2-Isopropylnaphthalenehydroperoxide; 2-Naphthol; Acetone; Catalysis; Catalytic reactions; Chemistry; Exact sciences and technology; General and physical chemistry; Liquid-phase catalytic reaction; Reactor operation conditions; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 0926-860X; 1873-3875
• DOI: 10.1016/S0926-860X(02)00290-9

Reactor operation parameters for the liquid-phase acid-catalyzed decomposition of 2-isopropylnaphthalenehydroperoxide (2-IPNHP) were investigated to produce simultaneously 2-naphthol and acetone with a high yield. The 2-naphthol and acetone are produced from 2-IPNHP by ionic reactions, nevertheless, dimethyl-2-naphthylcarbinol (DMNC) and 2-acetonaphthone (AN) formations through radical reactions cannot be avoided because of the induced decomposition effects but can be decreased. The decomposition of 2-IPNHP was carried out in the presence of two different aprotic solvents of low dielectric (DE) constant, i.e. 2-isopropylnapthalene (IPN) and acetone (AC), and the protogenic solvent acetic acid (AcOH), with two different oxyacid catalysts, i.e. HClO 4 and H 2SO 4. The production rate of 2-naphthol increases with the increase in the dipole moment (DM) of aprotic solvents. The increase in the initial 2-IPNHP concentration increases 2-IPNHP decomposition and 2-naphthol production rates. 2-Naphthol production rate decreases and the radical by-product AN formation rate increases with increasing temperature. The presence of the impurities DMNC and AN of the reactant mixture and a radical scavenger in the decomposition reaction medium decreased the 2-naphthol production rate. A 70% yield of 2-naphthol was obtained in the presence of IPN by 0.047 mol dm −3 HClO 4 with the initial concentrations of 1.155 mol dm −3 2-IPNHP, 0.470 mol dm −3 DMNC and 0.011 mol dm −3 AN at T=22 °C and N=1000 rpm. The reaction rate equations for the decomposition reaction of 2-IPNHP and production of 2-naphthol are also presented.