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Chemistry and Industry of Forest Products ›› 2015, Vol. 35 ›› Issue (3): 97-103.doi: 10.3969/j.issn.0253-2417.2015.03.017

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Green Synthesis of Isolongifolenone

PENG Han1, YANG Li-juan1, XU Xu2, WANG Shi-fa1   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
    2. Jiangsu Key Lab of Biomass-based Green Fuels and Chemical, Nanjing 210037, China
  • Received:2014-03-25 Online:2015-06-25 Published:2015-07-03

Abstract: Isolongifolenone was synthesized by using heavy turpentine as the starting material.Firstly,the heavy turpentine was converted to isolongifolene by isomerization reaction with BF3 (C2H5)2O as catalyst.Isolongifolenone was finally obtained from isolongifolene by allylic oxidation with tert-butyl hydroperoxide (TBHP) as oxidizer,Cu as catalyst and tert-butyl alcohol (TBA) as solvent.By investigating the influence of different react conditions on the oxidation of isolongifolene,the optimum conditions were determined as follows:the mass fraction of Cu 3% (based on the mass of isolongifolene),the mole ratio of TBHP and isolongifolene 3.5:1,the mass ratio of TBA and isolongifolene 1:1,reaction temperature 80 ℃ and reaction time 12 h.The yield of isofolenone was over 93%,and the purity was 98.75% under these conditions.

Key words: heavy turpentine, isolongifolene, allylic oxidation, isolongifolenone

CLC Number: