Chloromethylation of Naphthalene and Mathematical Planning of Experiment for Revealing Optimal Synthetic Conditions

  • V.V. Pak (Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substances) ;
  • R.K. Karimov (Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substance) ;
  • Kh.M. Shakhidoyatov (Acad. S.Yu. Yunusov Institute of the Chemistry of Plant Substance) ;
  • L.M. Yun (Academy of Science) ;
  • Soh, Dea-Wha (Myongji University)
  • Published : 2004.05.01

Abstract

$\alpha$-Chloromethylnaphthalene is a valuable compound for obtaining of the plant growing stimulator - $\alpha$-napthylacetic acid. Chloromethylation of naphthalene by paraformaldehyde in the presence of glacial acetic acid, phosphoric and hydrochloric acids at temperature 80-85$^{\circ}C$ and duration - 6 hours the $\alpha$-chloromethyl-naphthalene yield was 55-57%. Using Box-Wilson method for mathematical planning of experiment carried out optimization of its synthesis for purpose increasing $\alpha$-chloromethylnaphthalene yield. Preliminary, one - factor experiments were carried out for selecting independence main parameters influencing on the synthesis. A full factor experiment of 2$^3$with extended matrix of planning was used for optimization. Aiming to increase the $\alpha$-chloromethylnaphthalene yield, the obtained mathematical model was used for program of sharp raising on the reply surface. The received optimal conditions for the $\alpha$-chloromethylnaphthalene synthesis were selected as following: molar ratio of naphthalene - parapfsormaldehyde of 1 : 2; temperature -105$^{\circ}C$; duration of the reaction -3 hours. The yield of $\alpha$-chloromethylnaphthalene under these optimal conditions was 75 %.

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