Epoxidation of methyl abietate catalyzed by tetrabutylammonium divacant lacunary silicotungstate

HUANG Daozhan1,2, LAN Hongyun2, CHEN Qiaoping2, HE Zhibiao2, LEI Fuhou2, ZENG Tao1*

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2009, Vol. 33 ›› Issue (05) : 95.

JOURNAL OF NANJING FORESTRY UNIVERSITY ›› 2009, Vol. 33 ›› Issue (05) : 95. DOI: 10.3969/j.jssn.1000-2006.2009.05.021

Epoxidation of methyl abietate catalyzed by tetrabutylammonium divacant lacunary silicotungstate

  • HUANG Daozhan1,2, LAN Hongyun2, CHEN Qiaoping2, HE Zhibiao2, LEI Fuhou2, ZENG Tao1*
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Abstract

The epoxidation reaction of methyl abietate with 30% H2O2 as oxidant catalyzed by tetrabutylammonium divacant lacunary silicotungsate in acetonitrile solvent was studied. UV, IR, GC and GC/MS spectra of the oxidation products showed that monoepoxide and diepoxide of methyl abietate were mainly formed by the mild selective oxidation of methyl abietate with H2O2. The influences of catalyst and oxidant dosage, temperature, reaction time on oxidation conversion and selectivity were investigated by monitoring the course of reaction. The optimum conditions were investigated as follow: methyl abietate 5 mmol, catalyst 10 μmol,30% H2O2 0.45 mL, acetonitrile 5 mL, reaction temperature 50℃ and reaction time 10 h. The oxidation conversion of methyl abietate and the epoxidation selectivity were 98% and 62%, respectively under that conditions.

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HUANG Daozhan1,2, LAN Hongyun2, CHEN Qiaoping2, HE Zhibiao2, LEI Fuhou2, ZENG Tao1*. Epoxidation of methyl abietate catalyzed by tetrabutylammonium divacant lacunary silicotungstate[J]. JOURNAL OF NANJING FORESTRY UNIVERSITY. 2009, 33(05): 95 https://doi.org/10.3969/j.jssn.1000-2006.2009.05.021

References

[1]程芝. 天然树脂生产工艺学[M]. 北京:中国林业出版社,1996.
[2]姚兴东,聂园梅,蓝丽红,等. 一种枞酸的制备方法:CN101020630[P]. 2007.
[3]孔振武,黄焕,王定选. 松香松节油在环氧树脂及固化剂中的应用进展[J]. 东北林业大学学报,2004,32(5):66-69.
[4]张招贵,刘锋,黄旺生,等. 有机硅化合物改性环氧松香[C]//中国化学会第四届有机化学学术会议论文集:下册. 2005.
[5]王涛,粟子安. 枞酸自动氧化产物的研究[J]. 林产化学与工业,1991,11(3):173-181.
[6]Kuzakov E V, Shmidt E N, Bagryanskaya I Y, et al. Reactions of diterpenoids on solid supports. I. oxidation of methyl abietate on the sorbents Al2O3 and SiO2 containing potassium permanganate[J]. Chemistry of Natural Compounds, 1994, 30(3): 339-345.
[7]Arbuzov B A, Khismatullina A G. The monooxide and dioxide of abietic acid[J]. Russian Chemical Bulletin, 1961, 10(7): 1190-1196.
[8]Valverde S, Lopez J C, Rabanal R M, et al .Reactions of abietic acid methyl ester with mchloroperbenzoic acid[J]. Tetrahedron, 1986, 42(2): 573-582.
[9]Mizuno N, Yamaguchi K. Polyoxometalate catalysts: Toward the development of green H2O2based epoxidation systems[J]. Chemical Record, 2006, 6(1): 12-22.
[10]Noritaka Mizuno, Kazuya Yamaguchi, Keigo Kamata. Epoxidation of olefins[J]. Coordination Chemistry Reviews, 2005, 249(17-18): 1944-1956.
[11]欧阳小月,江焕峰. 以双氧水为氧源的烯烃环氧化反应[J]. 有机化学,2007,27(3):358-367.
[12]李丽,彭军,张龙. 杂多化合物催化过氧化氢氧化烯烃环氧化反应研究进展[J]. 精细化工中间体,2006,36(5):24-29.
[13]Keigo Kamata, Yoshinao Nakagawa, Kazuya Yamaguchi, et al. Efficient regioselective epoxidation of dienes with hydrogen peroxide catalyzed by [γSiW10O34(H2O)2]4-[J]. Journal of Catalysis, 2004, 224(1): 224-228.
[14]丁勇,高强,李贵贤,等. Keggin 类杂多化合物催化环氧化环戊烯的谱学研究[J]. 化学学报,2005,63(13):1167-1174.
[15]程时标.丁烯1在[(nC4H9)4N][γSiW10O36]催化剂上的环氧化[J]. 石油学报:石油加工,2004,20(3):80-84.
[16]韩广甸,赵树纬,李述文. 有机制备化学手册:下册[M]. 北京:石油化学工业出版社,1978.
[17]王恩波,刘连利,沈恩洪,等. 含ⅡA主族元素杂多钨酸盐的合成及性质[J]. 应用化学,1991,8(5):13-16.
[18]陈霞,章亚东,高晓蕾,等. 若干磷钼酸季铵盐的合成及其催化H2O2反应性能研究[J]. 河南化工,2004(3):14-17.

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