Synthesis of camphorquinone from α-pinene

doi:10.3969/j.issn.1000-2006.2013.03.022

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2013, Vol. 37 ›› Issue (03): 123-128.doi: 10.3969/j.issn.1000-2006.2013.03.022

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Synthesis of camphorquinone from α-pinene

LIANG Zhihua¹, LI Haojin¹, XU Xu^1,2, WANG Shifa^1,2*

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

Online:2013-06-18 Published:2013-06-18

Abstract

Abstract: Synthesis of camphorquinone was carried out by using α-pinene as the starting material. 2-chlorinated bornane was prepared by addition and isomerization of α-pinene and dry hydrogen chloride, and it was further eliminated HCl in order to obtain bornylene. Camphorquinone was finally obtained by oxidation of bornylene with KMnO₄ in mixed acetone-water solvent. Influences of phase-transfer catalysts and solvent systems, the amount of KMnO₄, acetone/H₂O ratio and the amount of mixed solvent, reaction temperature and reaction time on the oxidation of bornylene were examined in detail, and the suitable oxidation conditions were determined as follows:KMnO₄ was used as the oxidant for oxidizing bornylene into camphorquinone, and KMnO₄/bornylene molar ratio was 3.0:1; acetone/H₂O mixture with a volume ratio 3:1 was used as the solvent, and the solvent/bornylene ratio was 20:1(mL/g); the oxidation of bornylene was conducted at 30 ℃ for 4 h. The yield of camphorquinone was over 85% under the aforesaid conditions, and its chemical structure was determined with GC-MS, FTIR, ¹H NMR, and ¹³C NMR spectra.

CLC Number:

TQ245

LIANG Zhihua, LI Haojin, XU Xu, WANG Shifa. Synthesis of camphorquinone from α-pinene[J]. JOURNAL OF NANJING FORESTRY UNIVERSITY, 2013, 37(03): 123-128.

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