反式茴脑低温氧气氧化性质及其产物
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摘要
考察了反式茴脑氧化反应特性,采用自行设计的小型密闭压力容器跟踪反应压力变化,利用碘量法分析了过氧化物浓度,利用气相色谱-质谱联用仪分析了反应产物种类。实验结果表明,压力变化显示,反式茴脑氧化过程分3个阶段:首先是缓慢吸收氧气阶段;然后是快速氧化反应阶段;最后是氧化趋于结束阶段。当反应温度为95℃,反应时间为4 h时,过氧化物浓度最大为85.07 mmol/kg;反式茴脑氧化反应产物比较复杂,最主要的产物有茴香醛、乙醛、茴香环氧化物、茴香二醇、茴香偶酰等,当反应温度为55℃时,茴香醛选择性达到70.36%。
The oxidation characteristic and pressure of trans-anethole were determined using a self-designed mini closed pressure vessel device. Peroxide concentration was measured by iodimetry, and reaction products were analyzed by gas chromatography-mass spectrometry(GC-MS). Results showed that the oxidation reaction of trans-anethole with oxygen included three stages: first, oxygen was absorbed slowly, then the oxidation reaction of trans-anethole occurred rapidly, finally, oxidation process went to end. The peroxide concentration reached a maximum value of 85.07 mmol/kg when the reaction was carried at 95 ℃ for 4 h. The oxidation products were more complicated, mainly composing of anisaldehyde, acetaldehyde, anethole epoxide, anethole diol and p-anisil. A maximum anisaldehyde selectivity of 70.36% was obtained at 55 ℃.
The oxidation characteristic and pressure of trans-anethole were determined using a self-designed mini closed pressure vessel device. Peroxide concentration was measured by iodimetry, and reaction products were analyzed by gas chromatography-mass spectrometry(GC-MS). Results showed that the oxidation reaction of trans-anethole with oxygen included three stages: first, oxygen was absorbed slowly, then the oxidation reaction of trans-anethole occurred rapidly, finally, oxidation process went to end. The peroxide concentration reached a maximum value of 85.07 mmol/kg when the reaction was carried at 95 ℃ for 4 h. The oxidation products were more complicated, mainly composing of anisaldehyde, acetaldehyde, anethole epoxide, anethole diol and p-anisil. A maximum anisaldehyde selectivity of 70.36% was obtained at 55 ℃.
引文
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[9]Li Zhengqiu(李正球),Ha Chengyong(哈成勇),Ma Yijing(马一静),et al.Preparation of anisaldehyde from oxidation of anethole by manganese dioxide[J].Chemistry and Industry of Forest Products(林产化学与工业),2009,29(4):59-62.
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[13]Li Zelin(李则林),Zhang Yongkang(张永康),Cheng Jieping(成阶平).Electro oxidation of anethole to aldehyde[J].Fine Chemicals(精细化工),1995,12(11):16-18.
[14]Su Guijiao(粟桂娇),Liu Xiongmin(刘雄民),Li Weiguang(李伟光),et al.Biotransformation of anethole to anisaldehyde in aqueous organic solvents biphasic systems[J].Fine Chenmicals(精细化工),2009,26(2):136-141.
[15]Shimoni E,Baasov T,Ravid U,et al.The trans-anethole degradation pathway in an Arthrobacter sp[J].Journal of Biological Chemistry,2002,277(14):11866-11872.
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[17]National Health and Family Planning Commission of PRC(中华人民共和国国家卫生和计划生育委员会).peroxide value of food(食品中过氧化值的测定):GB 5009.227-2016[S].Beijing(北京):China Standards Press(中国标准出版社),2017,3.
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[19]Tang Shengwei(唐盛伟).An investigation on the liquid phase oxidation of toluene by air[D].Chengdu:Sichuan University,2005.
[20]He Jie(何洁).The thermal hazards of organic peroxides[D].Nanjing:Nanjing University of Science and Technology,2008.
[21]Li X R,Koseki H.Thermal decomposition kinetic of liquid organic peroxides[J].Journal of Loss Prevention in the Process Industries,2005,18(4/5/6):460-464.
[22]Su Guijiao(粟桂娇),Liu Xiongmin(刘雄民),Li Weiguang(李伟光),et al.Optimization of biotransformation conditions for transformation of trans-Anethole to anisic acid by pseudomonas sp.BT-13[J].Journal of Chemical Engineering of Chinese Universities(高校化学工程学报),2011,25(4):643-649.
[23]Jiang Ping(姜萍),Li Haiyu(李海玉),Mi Wei(米伟).Study on synthesis of anethole derivatives[J].Chemistry and Industry of Forest Products(林产化学与工业),2011,31(1):86-90.
[24]Su Guijiao(粟桂娇).Microbial degradation and biotransformation of trans-anethole to anisaldehyde and anicic acid[D].Nanning:Guangxi University,2011.
[25]Li Yunyan(李云艳),Li Minxian(李敏贤).Progress in the synthesis of anisaldehyde by anethole oxidation[J].Chemical Intermediate(化工中间体),2010,(1):12-15.
[26]Yang Aiyun(杨爱云),Liu Shirong(刘士荣),Cao Guangming(曹光明).On synthesis and utilization of anethole[J].Acta Sci Nat Univ Norm Hunan(湖南师范大学:自然科学学报),1995,18(1):90-96.
[27]Wang Qingjun(王庆军),Liu Fusheng(刘福胜),Yu Shitao(于世涛).Study on the preparation and application of methoxy benzaldehyde[J].Advances in Fine Petrochemicals(精细石油化工进展),2006,7(5):34-38.
[28]Lin Li(林莉).Anisic aldheyde[J].Fine and Specialty Chemicals(精细与专用化学品),2000,(12):33-34.
[2]Zhong Wenhai(钟文海).A modified method of the preparation of anisaldehyde through oxid a tion of anethole[J].Flavour Fragrance cosmetics(香料香精化学),1990,(4):6-7,27.
[3]Zhong Changyong(钟昌勇),Chen Haiyan(陈海燕),Liu Hong(刘虹).The purification technology of anethole anise[J]China Forestry Science and Technological(林业科技开发),2008,22(3):89-90.
[4]Li Zuguang(李祖光),Xu Danqian(许丹倩),Xu Zhenyuan(徐振元).Study on the aroma compounds released from star anise fruits[J].China condiment(中国调味品),2003,(10):13-15,20.
[5]Law Rence B M.A review of the world production of essential oils(1984)[J].Perf and Flav,1985,10(5):1-16.
[6]Marshall AD,Caldwell J.Influence of modulators of epoxide metabolism on the cytotoxicity of trans-anethole in freshly isolated rat hepatocytes[J].Food and Chemical Toxicology,1992,30:467-473.
[7]Marshall AD,Caldwell J.Lack of influence of modulators of epoxide metabolism on the genotoxicity of trans-anethole in freshly isolated rat hepatocytes assessed with the unscheduled DNA synthesis assay[J].Food and Chemical Toxicology,1996,34:337-345.
[8]Xiao Yi,Huang Hongmei,Yin Dulin,et al.Oxidation of anethole with hydrogen peroxide catalyzed by oxovanadium aromatic carboxylate complexes[J].Catalysis Communications,2008,(10):29-32.
[9]Li Zhengqiu(李正球),Ha Chengyong(哈成勇),Ma Yijing(马一静),et al.Preparation of anisaldehyde from oxidation of anethole by manganese dioxide[J].Chemistry and Industry of Forest Products(林产化学与工业),2009,29(4):59-62.
[10]Huang Wenbang(黄文榜),Jiang Qin(姜勤).Anisaldehyde was synthesized by anisole oxidation with phase transfer catalyze potassium permanganate[J].Chemistry world(化学世界),1988,29(6):253-256.
[11]Gao Rong(高蓉),Li Wenhong(李稳宏),Li Dong(李冬),et al.Preparation of anisaldehyde from star anise oil by ozonolysis reaction[J].Chinese Journal of Food Science(食品科学),2008,29(6):174-177.
[12]Yu Jing(于静),Ha Chengyong(哈成勇),Shen Minmin(沈敏敏),et al.New process for preparation of anisaldehyde based on ozonolysis of anethole in mixture solvent system[J].Journal of Chemical Engineering of Chinese Universities(高校化学工程学报),2012,26(3):475-480.
[13]Li Zelin(李则林),Zhang Yongkang(张永康),Cheng Jieping(成阶平).Electro oxidation of anethole to aldehyde[J].Fine Chemicals(精细化工),1995,12(11):16-18.
[14]Su Guijiao(粟桂娇),Liu Xiongmin(刘雄民),Li Weiguang(李伟光),et al.Biotransformation of anethole to anisaldehyde in aqueous organic solvents biphasic systems[J].Fine Chenmicals(精细化工),2009,26(2):136-141.
[15]Shimoni E,Baasov T,Ravid U,et al.The trans-anethole degradation pathway in an Arthrobacter sp[J].Journal of Biological Chemistry,2002,277(14):11866-11872.
[16]Shimoni E,Baasov T,Ravid U,et al.Biotransformations of propenylbenzenes by an Arthr obacter sp.and its t-anethole blockedmutants[J].Journal of Biotechnology,2003,105(1):61-70.
[17]National Health and Family Planning Commission of PRC(中华人民共和国国家卫生和计划生育委员会).peroxide value of food(食品中过氧化值的测定):GB 5009.227-2016[S].Beijing(北京):China Standards Press(中国标准出版社),2017,3.
[18]Liu Xiongmin(刘雄民),Huang Pinxian(黄品鲜),Li Piaoying(李飘英),et al.Thermal decomposition temperature of organic peroxides studied by CPVT[J].Chemistry world(化学世界),1998,13(10):541-543.
[19]Tang Shengwei(唐盛伟).An investigation on the liquid phase oxidation of toluene by air[D].Chengdu:Sichuan University,2005.
[20]He Jie(何洁).The thermal hazards of organic peroxides[D].Nanjing:Nanjing University of Science and Technology,2008.
[21]Li X R,Koseki H.Thermal decomposition kinetic of liquid organic peroxides[J].Journal of Loss Prevention in the Process Industries,2005,18(4/5/6):460-464.
[22]Su Guijiao(粟桂娇),Liu Xiongmin(刘雄民),Li Weiguang(李伟光),et al.Optimization of biotransformation conditions for transformation of trans-Anethole to anisic acid by pseudomonas sp.BT-13[J].Journal of Chemical Engineering of Chinese Universities(高校化学工程学报),2011,25(4):643-649.
[23]Jiang Ping(姜萍),Li Haiyu(李海玉),Mi Wei(米伟).Study on synthesis of anethole derivatives[J].Chemistry and Industry of Forest Products(林产化学与工业),2011,31(1):86-90.
[24]Su Guijiao(粟桂娇).Microbial degradation and biotransformation of trans-anethole to anisaldehyde and anicic acid[D].Nanning:Guangxi University,2011.
[25]Li Yunyan(李云艳),Li Minxian(李敏贤).Progress in the synthesis of anisaldehyde by anethole oxidation[J].Chemical Intermediate(化工中间体),2010,(1):12-15.
[26]Yang Aiyun(杨爱云),Liu Shirong(刘士荣),Cao Guangming(曹光明).On synthesis and utilization of anethole[J].Acta Sci Nat Univ Norm Hunan(湖南师范大学:自然科学学报),1995,18(1):90-96.
[27]Wang Qingjun(王庆军),Liu Fusheng(刘福胜),Yu Shitao(于世涛).Study on the preparation and application of methoxy benzaldehyde[J].Advances in Fine Petrochemicals(精细石油化工进展),2006,7(5):34-38.
[28]Lin Li(林莉).Anisic aldheyde[J].Fine and Specialty Chemicals(精细与专用化学品),2000,(12):33-34.
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