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2,3-吡嗪二甲酸二茴香酯的合成及其热裂解

Synthesis and Pyrolysis of 2, 3-Pyrazinedicarboxylic Acid Dianisalcohol Ester

  • 摘要: 为了开发新型吡嗪类烟用香料,以茴香醇和2,3-吡嗪二甲酸为原料,N,N'-二环己基碳二亚胺(DCC)为缩水剂,在4-二甲氨基吡啶(DMAP)的催化作用下,合成了化合物Ⅰ。通过IR,1H NMR,13C NMR和HRMS等波谱技术确证了产物结构,并进行了热裂解实验。结果表明:①化合物Ⅰ为目标产物2,3-吡嗪二甲酸二茴香酯。②合成化合物Ⅰ的最佳条件为:2,3-吡嗪二甲酸:茴香醇=1:2.1(摩尔比),2,3-吡嗪二甲酸和DMAP的用量均为1.5 mmol,常温下反应12 h,收率57%。③化合物Ⅰ的初次裂解温度为266.9℃,二次裂解温度为530.8℃;在400℃左右失重约70.62%,失重率在274.9℃时达到最大。④裂解温度对热裂解产物的种类和相对质量分数影响较大;各温度下的主要裂解产物有吡嗪、对甲基茴香醚、大茴香醚、大茴香醛和苯甲醛等香味成分。

     

    Abstract: In order to develop novel tobacco flavors of pyrazines, Compound Ⅲ was synthesized from 2, 3-pyrazinedicarboxylic acid and anisalcohol with N,N'-dicyclohexylcarbodiimide(DCC) as dehydration reagent under the catalysis of 4-(dimethylamino) pyridine(DMAP). The structure of Compound Ⅲ was confirmed by IR, 1H NMR, 13C NMR and HRMS spectra, the pyrolysis of Compound Ⅲ was tested. The results showed that: 1) Compound Ⅲ was the target compound, 2, 3-pyrazinedicarboxylic acid dianisalcohol ester. 2) The yield of Compound Ⅲ reached 57%under the optimal reaction conditions of the mole ratio of the acid and anisalcohol 1:2.1, with an amount of 1.5 mmol each for the acid and DMAP, reacting for 12 hours at room temperature. 3) The primary and secondary pyrolysis temperatures of Compound Ⅲ were 266.9and 530.8 Ⅲ, respectively. Its mass loss reached about 70.62% around 400 Ⅲ and mass loss rate peaked at 274.9 Ⅲ. 4) Pyrolysis temperature affected the composition and relative contents of pyrolysis products significantly. The major pyrolysis products at different temperatures included pyrazine, 4-methylanisole, anisole, p-anisaldehyde and benzaldehyde among others.

     

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