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3,6-二甲基-2,5-吡嗪二甲酸酯的合成及其卷烟加香应用
Synthesis of 3,6-Dimethyl-2,5-pyrazinedicarboxylate and Its Application in Cigarette Flavoring

作  者: (单园园); (来苗); (赵铭钦); (姬小明);

机构地区: 河南农业大学烟草学院,河南郑州450002

出  处: 《精细化工》 2017年第9期1010-1016,共7页

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℃,其失重达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。 3,6-Dimethyl-2,5-pyrazinediformyl chloride was synthesized by oxidation and acylating chlorination from 2,3,5,6-tetramethylpyrazine,and then reacted with 1-octen-3-ol to afford an aroma precursor compound,di( 1-octen-3-yl)-3,6-dimethyl-2,5-pyrazinedicarboxylate( DMPOE). The structure of DMPOE was confirmed by1 HNMR,13CNMR,IR and HRMS techniques. And thermogravimetric( TG-DTG-DSC) analysis and pyrolysis-gas chromatography/mass spectrometry( PyGC/MS) analysis were used to investigate the thermal property of DMPOE. The results showed that the synthetic product was the target compound. The largest mass loss of DMPOE occurred from 220 to 360℃,within the temperature range,the percentage of weight loss was 85. 2%. Compound DMPOE degraded since 225. 9 ℃,and the weight loss rate reached the maximum at 312 ℃ with a percentage of weight loss of 65. 48%. Nine kinds of typical products were identified by pyrolysis analysis,and main pyrolysis products were 2,5-dimethylpyrazine,1-octen-3-ol and 2-isobutyl-3-methylpyrazine and other flavoring substances. When DMPOE( 0. 75 mg/kg) was added into typical middle flavor style fluecured tobacco,DMPOE could improve the smoking quality,increase the aroma quantity,harmonize the aroma,and reduce offensive odor and irritation of cigarettes.

关 键 词: 辛烯 二甲基 吡嗪二甲酸酯 卷烟加香 烟用香原料

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