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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O626.3

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    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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History
  • Received:August 24,2022
  • Revised:November 23,2022
  • Adopted:December 01,2022
  • Online: May 11,2023
  • Published: