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Vol. 26 No. 22 (2014): Vol 26 Issue 22

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Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene Isopinocamphones from a-Pinene

https://doi.org/10.14233/ajchem.2014.17781
Jia-Yu Wang
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Peng-Na Wang
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Jin-Lai Yang
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Jia Shen
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China
Xu Xu
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China; Jiangsu Key Lab of Biomass-based green Fuels and Chemicals, Nanjing 210037, Jiangsu Province, P.R. China
Shi-Fa Wang
College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, Jiangsu Province, P.R. China; Jiangsu Key Lab of Biomass-based green Fuels and Chemicals, Nanjing 210037, Jiangsu Province, P.R. China

Corresponding Author(s) : Xu Xu

xuxu200121@163.com

Asian Journal of Chemistry, Vol. 26 No. 22 (2014): Vol 26 Issue 22

Abstract

A new series of 4-arylidene isopinocamphones were synthesized from a-pinene which is a natural chemical from pine tree and their ultraviolet absorption characteristics were investigated. (+)Isopinocamphone was obtained from a-pinene by hydroboration-oxidation and then it was reacted with benzaldehyde, p-methylbenzaldehyde, p-methoxybenzaldehyde, p-chlorobenzaldehyde, furfural and p-nitrobenzaldehyde in the presence of alkali catalysts to get 4-arylidene isopinocamphones including 2-benzylidene-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one (1), 2,6,6-trimethyl-4-(4-methyl benzyl)bicyclo[3.1.1]heptane-3-one (2), 2-(4-methoxybenzylidene)-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one (3), 2-(4-chlorobenzylidene)-4,6,6-trimethylbicyclo[3.1.1]heptan-3-one (4), 2-(furan-2-methylene)-4,6,6-trimethylbicyclic [3.1.1] heptane-3-one (5) and 2,6,6-trimethyl-4-(4-nitrobenzylidene)bicyclo[3.1.1]heptan-3-one (6). The structures of 4-arylidene isopinocamphones were determined by FT-IR, 1H NMR, 13C NMR and GC-MS technique. Their ultraviolet absorption characteristics and light stability was further examined. The results showed that compounds 1, 2, 3 and 5 could be used as B-type UV absorbents, compounds 4 and 6 could be used as A-type UV absorbents and compounds 6 had both functions as UV-A and UV-B types absorbents. The light stability sequence of these compounds was (2) > (1) » (3) » (4) » (6) > (5).

Keywords

4-Arylidene isopinocamphones Ultraviolet absorbent ( )isopinocamphone α-Pinene Light stability
Wang, J.-Y., Wang, P.-N., Yang, J.-L., Shen, J., Xu, X., & Wang, S.-F. (2014). Synthesis and Ultraviolet Absorption Characteristics of 4-Arylidene Isopinocamphones from a-Pinene. Asian Journal of Chemistry, 26(22), 7779–7784. https://doi.org/10.14233/ajchem.2014.17781
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