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›› 2013, Vol. 33 ›› Issue (5): 61-66.doi: 10.3969/j.issn.0253-2417.2013.05.012

• 1研究报告 • Previous Articles     Next Articles

Synthesis of Camphoric Anhydride from α-Pinene

LIANG Zhi-hua1, LI Hao-jin1, XU Xu1,2, WANG You-xiang3, WANG Shi-fa1,2   

  1. 1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;2. Jiangsu Key Lab ofBiomass-based Green Fuels and Chemicals, Nanjing 210037, China;3. Chongyi Forestry, Chongyi 341300, China
  • Received:2012-08-27 Revised:1900-01-01 Online:2013-10-30 Published:2013-10-30

Abstract: Synthesis of camphoric anhydride was carried out using α-pinene as the starting material. 2-chlorocamphane was prepared by addition and isomerization of α-pinene and dry hydrogen chloride, and it was further eliminated HCl in alkaline condition to obtain bornylene. Camphoric anhydride was finally obtained by oxidation of bornylene with KMnO4 in mixed acetic anhydride-water solvent. Influences of solvent systems, volume ratio of acetic anhydride and water, the amount of KMnO4, reaction temperature and reaction time on the oxidation of bornylene were examined in detail. The suitable oxidation conditions were determined as follows: KMnO4 used as the oxidant for oxidizing bornylene into camphoric anhydride, KMnO4/bornylene molar ratio 2.5:1, acetic anhydride/H2O mixture with a volume ratio of 3:1 used as the solvent, solvent/bornylene ratio 20:1(mL:g), reaction temperature 40℃ and reaction time 4 h. The yield of camphoric anhydride was over 94% under the aforesaid conditions. Its chemical structure was determined with GC-MS, FT-IR, 1H NMR, and 13C NMR spectra.

Key words: α-pinene, camphoric anhydride, 2-chlorocamphane, bornylene, oxidation

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