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Chemistry and Industry of Forest Products ›› 2014, Vol. 34 ›› Issue (2): 103-107.doi: 10.3969/j.issn.0253-2417.2014.02.018

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Synthetic of 6-(4-Methylpent-3-enyl)naphthalene-1,4-dione

FENG Hong-jun1, YANG Jiu-fang1, GAO Fei-fei1, LUO Jin-yue1 2, LU Qiang1, XU Xu1 2   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. Jiangsu Key Lab of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China
  • Received:2013-04-01 Online:2014-04-25 Published:2014-04-26

Abstract: The myrcene and 1,4-benzoquinone are used as raw materials to synthesize naphthalene catechol derivatives of naphthalene-1,4-diol. Further the naphthalene catechol derivatives of naphthalene-1,4-dione is synthesized by aromatization. The structure of the product is identified as 6-(4-methylpent-3-enyl)naphthalene-1,4-dione by GC-MS, the FT-IR, 1H NMR characterization. The synthesis conditions from hydronaphthoquinone to morkit were investigated. The experimental parameters such as different type of catalysts, catalyst amount, reaction solvent, reaction temperature and reaction time have been investigated systematically with single-factor experimentation to obtain maximum yield. It is concluded that the fittest catalyst is manganese(IV) oxide, while the dosage of naphthalene-1,4-diol and catalyst is 0.02 mol and 0.05 mol, respectively. Acetic ester is chosen as solvent and the reaction temperature is 80 ℃, reaction time is 22 h. Under this condition, the yield of product reached 88.6%. Manganese(IV) oxide catalyst can be reused four times, while the yield decline is not obvious.

Key words: hydronaphthoquinone, morkit, aromatization, myrcene

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