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›› 2013, Vol. 47 ›› Issue (5): 40-44.doi: 10.3969/j.issn.1673-5854.2013.05.008

• 研究报告 • Previous Articles     Next Articles

Synthesis of p-Menthane-1, 2, 4-Triol and Its Herbicidal Activity for Barnyard Grass

HUANG Dao-zhan, WANG Xiao-shu, ZHU Shou-ji, YAN Fang, LAN Hong-yun, BAI Li-juan   

  1. College of Chemistry and Chemical Engineering, Guangxi University for Nationalities;Guangxi Key Lab. of Chemistry and Engineering of Forest Products, Nanning 530008, China
  • Received:2013-04-26 Revised:1900-01-01 Online:2013-09-30 Published:2013-09-30

Abstract: Oxidation of 4-terpineol with 30% H2O2 catalyzed by quaternary ammonium peroxotungsto-phosphate catalyst[π-C5H5(CH2)11CH3]3PW4O32 in 1,2-dichloroethane gave p-menthane-1,2,4-triol. The product was easily separated as a white crystalline powder by filtration and structurally identified by means of EA, IR, 1H NMR and 13C NMR. Under the optimal reaction conditions, i.e. 4-terpineol 12.3 mmol, 1,2-dichloroethane 5 mL, molar ratio of hydrogen peroxide to 4-terpineol 1.25:1, mass percentage of catalyst to 4-terpineol 2.98%, reaction temperature 50 ℃, reaction time 1.5 h, the conversion rate of 4-terpineol and yield of p-menthane-1,2,4-triol were 99.8% and 58.0%, respectively. The purity of product can reach more than 98%. The preliminary herbicidal assay had that p-menthane-1,2,4-triol had an obvious post-emergence inhibitory effect against shoot growth and root elongation of barnyard grass (Echinochloa crusgalli L.). The percentage inhibition of root growth and shoot elongation at 10 mmol/L concentration in herbicidal test were 100% and 81.4%, respectively.

Key words: 4-terpineol, catalytic oxidation, p-menthane-1, 4-triol, barnyard grass, herbicidal activity

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