两种新型羰基呋喃类香料前体的制备及其热性能
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河南农业大学烟草学院

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O626.3

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新型吡嗪类香味化合物的合成及其应用研究(NO. 30600715);河南农业大学拔尖人才项目(NO. 30501028)


Preparation and thermal properties of two new carbonyl furan flavor precursors
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College of Tobacco Science, Henan Agricultural University

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    摘要:

    为开发羰基呋喃类香料前体,分别以2-乙酰基吡啶、2-乙酰基噻吩和糠醇为起始原料,在iprPNP型Pincer锰催化剂的催化作用下经脱氢偶联反应一步合成3-(呋喃-2-基)-1-(吡啶-2-基)丙-1-酮 (Ⅲa)和3-(呋喃-2-基)-1-(噻吩-2-基)丙-1-酮 (Ⅲb)。通过1H NMR、13C NMR、HRMS表征目标化合物的结构,并对其热性能进行鉴定。结果表明,目标化合物Ⅲa从99.9 ℃开始降解,主要失重区间为99.9~875 ℃,在259 ℃失重速率最大,总失重为97.31%;目标化合物Ⅲb从116.2 ℃开始降解,主要失重区间为116.2~875 ℃,在274 ℃失重速率最大,总失重为98.41%。在300~900 ℃的有氧裂解氛围下,目标化合物Ⅲa裂解后主要有烷基呋喃类、烷基吡啶类、2-乙酰吡啶等特征香味物质;目标化合物Ⅲb裂解后鉴定出烷基呋喃类、烷基噻吩类、2-乙酰呋喃等特征香味物质。通过对单料烟进行加香效应评价,确定目标化合物Ⅲb的最适宜添加量为3mg/kg。

    Abstract:

    In order to develop carbonyl furan flavor precursors, 2-acetylpyridine, 2-acetylthiophene and furfuryl alcohol were used as raw materials to synthesize 1-(furan-2-yl)-1-(Pyridin-2-yl) propan-1-one (Ⅲa) and 1-(furan-2-yl)-1-(thiophen-2-yl) propan-1-one (Ⅲb) in one step via dehydrogenative coupling reaction using iprPNP pincer manganese catalyst. The structure of the compounds Ⅲa and Ⅲb was characterized by 1H NMR, 13C NMR and HRMS, and its thermal properties were identified. The results showed that the target compound Ⅲa began to degrade from 99.9 °C, the main weightlessness interval was 99.9-875 °C, and the weightlessness rate was the largest at 259 °C, with a total weightlessness of 97.31%. The target compound Ⅲb began to degrade from 116.2 °C, the main weightlessness interval was 116.2~875 °C, and the maximum weightlessness rate at 274 °C was 98.41%. Under the aerobic cracking atmosphere of 300~900 °C, a total of 9 volatile products were identified after the cracking of the target compound Ⅲa, mainly including alkyl furans, alkyl pyridines, 2-acetylpyridine and other characteristic fragrance substances; After the cracking of the target compound Ⅲb, a total of 13 volatile products were identified, mainly including alkyl furans, alkyl thiophenes, 2-acetylfurans and other characteristic fragrance substances. According to the changes in the types and relative contents of the main cleavage products, the cracking mechanism was preliminarily revealed. The most suitable addition amount of target compound Ⅲb in a single cigarette is 3mg/kg through the evaluation of incense effect.

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李欣燕,张晓雨,赵巧玥,崔冰,来洪涛,邵志晖,赵铭钦.两种新型羰基呋喃类香料前体的制备及其热性能[J].精细化工,2023,40(6):

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  • 收稿日期:2022-08-24
  • 最后修改日期:2022-11-23
  • 录用日期:2022-12-01
  • 在线发布日期: 2023-05-11
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