一种3,6-二甲基-2,5-吡嗪二甲酸酯的合成及其卷烟加香应用
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TQ655.5

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河南省科技厅重点科技攻关项目


Synthesis of a 3,6-Dimethyl-2,5-pyrazinedicarboxylate and Its Application in Cigarette Flavoring
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    摘要:

    以四甲基吡嗪为原料,经氧化和酰氯化反应得到3,6-二甲基-2,5-吡嗪二甲酰氯后,与1-辛烯-3-醇经酯化反应得到潜香化合物——二(1-辛烯-3-醇)-3,6-二甲基-2,5-吡嗪二甲酸酯(DMPOE)。采用1HNMR、13CNMR、IR和HRMS表征其结构,经热重(TG-DTG-DSC)和热裂解-气相色谱/质谱(Py-GC/MS)分析测定其热性能。结果表明:合成产物为目标化合物;DMPOE的主要热失重区间为220~360 ℃,失重达85.2%,从224.9 ℃开始降解,在312 ℃失重率最大,失重约65.48%;热裂解共检测到9种代表性产物,主要有2,5-二甲基吡嗪、1-辛烯-3-醇和2-异丁基-3-甲基吡嗪等香味物质;在典型中间香型烤烟烟叶中加入0.75 mg/kg的DMPOE可以改善卷烟吸食品质,增补烟香,协调香气,降低杂气和刺激性。

    Abstract:

    3,6-Dimethyl-2,5-pyrazinediformyl chloride was synthesized by oxidation and acylating chlorination from 2,3,5,6-tetramethylpyrazine. The aroma precursor compound of di (1-octen-3-yl)-3,6-dimethyl-2,5-pyrazinedicarboxylate was synthesized by esterification with 1-octen-3-ol and 3,6-dimethyl-2,5-pyrazinediformyl chloride. The structure of di (1-octen-3-yl)-3,6-dimethyl-2,5-pyrazinedicarboxylate was confirmed by 1HNMR, 13CNMR, IR and HRMS spectra. The thermal property of DMPOE was measured by the thermogravimetric (TG-DTG-DSC) analysis and pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) analysis. The results showed that: The synthetic product was the target compound; The TG curve showed that the largest mass loss occurred from 220 to 360 ℃, with weight loss of 85.2%. The target compound degraded began from 225.9 ℃, and the weightlessness rate reached the maximum at 312 ℃ with 65.48% of weightlessness. Nine kinds of typical products were identified by pyrolysis analysis, and main pyrolysis products were 2,5-dimethyl pyrazine, 1-octen-3-ol and 2-isobutyl-3-methylpyrazine which were aroma components. With adding of 0.75 mg/kg to typical middle flavor style flue-cured tobacco, it could improve the smoking quality, increase the aroma quantity, reduce offensive odor and irritation and modify the smoke.

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单园园,来苗,赵铭钦,姬小明.一种3,6-二甲基-2,5-吡嗪二甲酸酯的合成及其卷烟加香应用[J].精细化工,2017,34(9):0

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  • 收稿日期:2016-10-17
  • 最后修改日期:2017-03-03
  • 录用日期:2017-03-17
  • 在线发布日期: 2017-08-03
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