N-丁基-2-甲基-3-乙酰基-5-(1',2',3',4'-四羟基丁基)吡咯的热裂解气相色谱-质谱分析  

Analysis on 3-Acetyl-N-butyl-2-methyl-5-( 1',2',3',4'-tetrahydroxybutyl) Pyrrol by Gas Chromatography-Mass Spectrometry

作　　者：陶陶[1] 赵华新[2] 姬小明[1] 来苗 祁令凯[1] 

机构地区：[1]河南农业大学烟草学院,河南郑州450002 [2]河南农业大学生命科学学院,河南郑州450002

出　　处：《精细化工》2015年第12期1388-1393,共6页Fine Chemicals

基　　金：河南省科技厅重点科技攻关项目(152102210058)~~

摘　　要：以D-(+)-氨基葡萄糖盐酸盐为原料,通过环化和烷基化反应合成了目标化合物N-丁基-2-甲基-3-乙酰基-5-(1',2',3',4'-四羟基丁基)吡咯,并通过~1HNMR、^(13)CNMR、IR和HRMS技术对其结构进行表征。采用热重-微分热重-差示扫描量热法(TG-DTG-DSC)分析了目标化合物的热变化情况,结合热裂解-气相色谱-质谱技术(Py-GC-MS)研究了目标化合物在300、600、900℃的热裂解行为,并对目标化合物进行卷烟加香评吸。结果表明:目标化合物的初始裂解温度为137.6℃,二次裂解温度为224.9℃,900℃时裂解物失重约65%;裂解产物总共有43种,其中有2,3-二甲基吡咯、N-甲基-3-乙酰基吡咯、2,4-二甲基-3-乙酰基吡咯等多种具有香味特征的物质;随着温度的升高,总裂解产物的量有增加趋势;目标化合物能够有效改善卷烟品质,增加卷烟香气,并以添加相对烟丝质量的0.03%时,其加香效果最为适宜。初步探讨了目标化合物可能的裂解机理,为研究其在卷烟燃烧过程中的转化行为提供参考。3-Acetyl-N-butyl-2-methyl-5- （ 1＇, 2＇, 3＇, 4＇-tetrahydroxy-butyl ） pyrrol was synthesized by cyclization reaction and alkylation reaction, then its structure was confirmed by 1 HNMR, 13 CNMR, IR and HRMS spectra. The thermo change was studied by themogravimetry-derivative themogravimetry- differential scanning calorimetry（ TG-DTG-DSC ）. Its pyrolysis behavior was investigated by pyrolysis- gas chromatography-mass spectrometry （Py-GC-MS） at 300,600,900 ℃ and the application of the target compound in cigarette flavoring was studied. The results indicated that the initial pyrolysis temperature of the target compound was 137.6 ℃, and the secondary pyrolysis temperature was 224.9℃. The thermal mass loss of the target compound reached about 65 % at 900 ℃. 43 pyrolysis products were detected, including the flavorous substances such as 2,3-dimethyl-lH-pyrrole, 3-aeetyl-N-methyl pyrrol and 3-acetyl-2,4-dimethylpyrrole, and the amount of total products increased with the increase of temperature. The target compound could improve and increase aroma quality, and with adding 0. 03% of cut tobacco weight, it showed the most appropriate flavoring effect. Possible pyrolysis mechanism of 3- acetyl-N-butyl-2-methyl-5- （ 1＇, 2＇, 3 ＇, 4＇-tetrahydroxy-butyl ） pyrrol was preliminarily discussed, which would provide a reference for the study of its conversion behavior in cigarette combustion process.

关 键 词：N-丁基-2-甲基-3-乙酰基-5-(1’ 2’  3’ 4'-四羟基丁基)吡咯 热裂解 热失重 烟草添加剂 香料与香精 

分 类 号：TQ655.5[化学工程—精细化工]