3-(2'-羟基亚苄基)诺蒎酮的合成、表征及其酸碱指示性能研究

doi:10.3969/j.issn.0253-2417.2016.05.001

Chemistry and Industry of Forest Products ›› 2016, Vol. 36 ›› Issue (5): 1-7.doi: 10.3969/j.issn.0253-2417.2016.05.001

Synthesis and Characterization of 3-(2'-Hydroxybenzylidene) Nopinone and Its Acid-base Indicator Performance

YANG Jin-lai^1,2, ZHANG Yan¹, RUI Jian¹, SUN Nan¹, XU Xu^1,3,5, YANG Yi-qin⁴, WANG Shi-fa^1,3,5

1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China;
2. China National Bamboo Research Center, Hangzhou 310012, China;
3. Jiangsu Co-innovation Center of Efficient Process and Utilization of Forest Resources, Nanjing Forestry University, Nanjing 210037, China;
4. College of Light Industry Science and Engineering, Nanjing Forestry University, Nanjing 210037, China;
5. Jiangsu Key Lab. of Biomass-based Green Fuels and Chemicals, Nanjing 210037, China

Received:2015-12-08 Online:2016-10-25 Published:2016-11-05

Abstract

Abstract: Nopinone was first synthesized by oxidation reaction of β-pinene. 3-(2'-Hydroxybenzylidene)nopinone was further synthesized by aldol condensation reaction of nopinone and salicylaldehyde and the process conditions were optimized by single factor and orthogonal experiment. The optimal condensation reaction conditions were determined as follows:1.43 g nopinone, tert-butyl alcohol (30 mL) as the solvent, potassium tert-butoxide (2.5 g) as the catalyst, the molar ratio of nopinone and salicylaldehyde 1:1.2 and the reflux reaction time 2 h. Under these condition, the yield of 3-(2'-hydroxybenzylidene)nopinone was 79.46%. The structure of 3-(2'-hydroxybenzylidene)nopinone was characterized and confirmed by MS, IR, NMR, and X-ray diffraction, and the crystal was in monoclinic system with P212121 space group. The acid-base indicator performance of 3-(2'-hydroxybenzylidene)nopinone was investigated. The results showed that the final color was orange and the measured concentration of hydrochloric acid was 0.259 6 mol/L with the RSD of 0.089%. When this compound was used to titrate hydrochloric acid standard solution (0.257 4 mol/L). As an acid-base indicator, 3-(2'-hydroxybenzylidene)nopinone was better than phenolphthanlein because of its high sensitivity and small deviation.

Key words: nopinone, aldol condensation, 3-(2'-hydroxybenzylidene)nopinone, acid-base indicator

CLC Number:

TQ35

YANG Jin-lai, ZHANG Yan, RUI Jian, SUN Nan, XU Xu, YANG Yi-qin, WANG Shi-fa. Synthesis and Characterization of 3-(2'-Hydroxybenzylidene) Nopinone and Its Acid-base Indicator Performance[J]. Chemistry and Industry of Forest Products, 2016, 36(5): 1-7.

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Synthesis and Characterization of 3-(2'-Hydroxybenzylidene) Nopinone and Its Acid-base Indicator Performance

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