Beckmann重排反应中催化剂应用研究进展
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摘要
传统的Beckmann重排反应常以磷酸或者浓硫酸等作催化剂,该工艺副产物繁多、操作复杂、环境污染大。本文对近年来Beckmann重排反应新的催化剂发展作了介绍,并归类分成固体酸催化剂、活泼氯化物催化剂、离子液体催化等,这些新发展的催化剂主要特点是用量少、污染少、产品收率高。
The traditional Beckmann rearrangement reaction is often catalyzed by phosphoric acid or concentrated sulfuric acid. The process has many by-products, complex operation and great environmental pollution. In this paper, the development of new catalysts for Beckmann rearrangement reaction in recent years is introduced, and they are classified into solid acid catalysts, active chloride catalysts and ionic liquid catalysts. The main characteristics of these new catalysts are less consumption, less pollution and high yield of products.
The traditional Beckmann rearrangement reaction is often catalyzed by phosphoric acid or concentrated sulfuric acid. The process has many by-products, complex operation and great environmental pollution. In this paper, the development of new catalysts for Beckmann rearrangement reaction in recent years is introduced, and they are classified into solid acid catalysts, active chloride catalysts and ionic liquid catalysts. The main characteristics of these new catalysts are less consumption, less pollution and high yield of products.
引文
[1]陆忠.新型环境友好催化剂催化贝克曼重排反应的研究[D].兰州:西北师范大学, 2008.
[2] Wang B, Gu Y L, Luo C, et al. Sulfamic acid as a costeffective and recyclable catalyst for liquid Beckmann rearrangement, a greenprocess to produce amides from ketoximes without waste[J]. Tetrahedron Lett.,2004,45:3369-3372.
[3] Marziano N C, Ronchin L, Tortato C, et al. Catalyzed Beckmann rearrangement of cyclohexanone oxime in heterogeneous liquid/solid system:Part 2:Influence of acid catalysts and organic promoters[J]. Journal of Molecular Catalysis A Chemical, 2008, 290(1):79-87.
[4]孙群宁,白浩,刘学军.固体酸催化剂的研究进展[J].广东化工, 2013, 40(23):110-112.
[5]毛东森,卢冠忠,陈庆龄,等. B2O3/TiO2-ZrO2催化环己酮肟气相Beckmann重排反应的研究Ⅰ. BXO3含量的影响[J].催化学报, 2002, 23(1):9-14.
[6]陈蕾.复合催化剂在环己烷亚硝化一步制己内酰胺中的催化性能[D].长沙:湖南师范大学, 2008.
[7] Monalisa B, Dilip K. Al Cl3·6H2O/KI/H2O/CHXCN:A New Alternate System for Dehydration of Oximes and Amides in Hydrated Media[J]. Journal of Organic Chemistry, 2002,67(20):7138-7139.
[8] Williams R H, Snyder H R. Preparation of 11-substituted5,6-dihydro-11H-6-oxodibenzo[b,e]azepines(morphanthridines)and their N-dimethylaminoethyl derivatives[J].J.org.chem, 1973, 38(4):809-811.
[9] Barman D C, Thakur A J, Prajapati D, et al. Indium-mediated facile dehydration and Beckmann rearrangement of oximes[J]. Chemistry letters, 2000, 29(10):1196-1197.
[10] Boruah M, Konwar D. Al Cl(3)x 6H(2)O/KI/H(2)O/CH(3)CN:a new alternate system for dehydration of oximes and amides in hydrated media[J]. Journal of Organic Chemistry, 2002, 67(20):7138-7139.
[11] Daisuke Shouro, Yukinori Moriya, Tsuyoshi Nakajima, et al. Mesoporous silica FSM-16 catalysts modified with various oxides for the vapor-phase Beckmann rearrangement of cyclohexanone oxime[J]. APPlied Catalysis A:General,2000, 198:275-282.
[12] Sato H. Characteristics of ultrasonic dispersion of carbon nanotubes aided by antifoam[J]. Catalysis Review Science Engineering, 1997, 39(4):395-424.
[13]尹双凤,徐柏庆.环己酮肟在改性氧化锆催化剂上的Beckmann重排反应Ⅴ.活化焙烧温度对B2O3/ZrO2催化剂的影响[J].催化学报, 2002, 23(6):507-512.
[14]陶伟川,毛东森,陈庆龄,等. Silicalite-1的后处理对其催化环己酮肟气相Beckmann重排反应性能的影响[J].催化学报, 2005, 26(5):417-422.
[15]谢祎.固体磺酸催化环己酮肟液相贝克曼重排制备己内酰胺工艺研究[D].湘潭:湘潭大学, 2016.
[16]周云, Satmon John,陈亨权,等. Amberlyst 36磺酸树脂催化环己酮肟液相重排制己内酰胺[J].合成纤维工业,2016,(3):11-15.
[17] Li D, Shi F, Guo S, et al. Highly efficient Beckmann rearrangement and dehydration of oximes[J]. Cheminform,2005, 36(20):671-674.
[18]贾金锋,隗小山,廖有贵,等.三聚氯氰催化液相重排合成ε-己内酰胺[J].化工技术与开发, 2017, 46(5):25-28.
[19] Zanger M. Synthesis of tetrahydrobenzazepinesulfonamides and their rearrangement to diarylsulfones[J]. Synthetic Communications, 2006, 36(3):355-363.
[20]李曹龙,王洪林,刘光恒.离子液体系中催化环己酮肟重排反应的研究[J].云南化工, 2004, 31(2):4-6.
[21]李红艳,李凌飞,王智慧.离子液体催化反应研究进展[J].黑龙江科技信息, 2017,(14):25-25.
[22]闫华,张红梅,张丽静,等.离子液体研究进展[J].山东化工, 2016, 45(23):55-57.
[23]郭术,邓友全.室温离子液体与固体酸复合催化体系中环己酮肟Beckmann重排反应[C].全国催化学术会议,杭州, 2002.
[24]赵江琨,王荷芳,王延吉,等.酸性离子液体-ZnCl2催化环己酮肟液相Beckmann重排反应[J].高校化学工程学报, 2011, 25(5):838-843.
[25]彭家建,邓友全.离子液体系中催化环己酮肟重排制己内酰胺[J].石油化工, 2001, 30(2):91-92.
[26]张伟,吴巍,张树忠,等.[bmim][BF4]离子液体中PCl3催化的液相贝克曼重排[J].过程工程学报, 2004, 4(3):261-264.
[27] Feng J C, Liu B, Dai L, et al. One-step Beckmann rearrangement from ketones and hydroxylamine in dry media under microwave irradiation[J].中国化学快报:英文版,1998, 9(9):795-796.
[28]程庆彦,朱响林,王延吉,等.超声波辐射P2O5催化环己酮肟液相贝克曼重排合成己内酰胺[J].高校化学工程学报, 2017, 31(1):58-66.
[29] Li Y, Wang K, Qin K, et al. Beckmann rearrangement reaction of cyclohexanone oxime in sub/supercritical water:Byproduct and selectivity[J]. Rsc Advances, 2015, 5(32):25365-25371.
[2] Wang B, Gu Y L, Luo C, et al. Sulfamic acid as a costeffective and recyclable catalyst for liquid Beckmann rearrangement, a greenprocess to produce amides from ketoximes without waste[J]. Tetrahedron Lett.,2004,45:3369-3372.
[3] Marziano N C, Ronchin L, Tortato C, et al. Catalyzed Beckmann rearrangement of cyclohexanone oxime in heterogeneous liquid/solid system:Part 2:Influence of acid catalysts and organic promoters[J]. Journal of Molecular Catalysis A Chemical, 2008, 290(1):79-87.
[4]孙群宁,白浩,刘学军.固体酸催化剂的研究进展[J].广东化工, 2013, 40(23):110-112.
[5]毛东森,卢冠忠,陈庆龄,等. B2O3/TiO2-ZrO2催化环己酮肟气相Beckmann重排反应的研究Ⅰ. BXO3含量的影响[J].催化学报, 2002, 23(1):9-14.
[6]陈蕾.复合催化剂在环己烷亚硝化一步制己内酰胺中的催化性能[D].长沙:湖南师范大学, 2008.
[7] Monalisa B, Dilip K. Al Cl3·6H2O/KI/H2O/CHXCN:A New Alternate System for Dehydration of Oximes and Amides in Hydrated Media[J]. Journal of Organic Chemistry, 2002,67(20):7138-7139.
[8] Williams R H, Snyder H R. Preparation of 11-substituted5,6-dihydro-11H-6-oxodibenzo[b,e]azepines(morphanthridines)and their N-dimethylaminoethyl derivatives[J].J.org.chem, 1973, 38(4):809-811.
[9] Barman D C, Thakur A J, Prajapati D, et al. Indium-mediated facile dehydration and Beckmann rearrangement of oximes[J]. Chemistry letters, 2000, 29(10):1196-1197.
[10] Boruah M, Konwar D. Al Cl(3)x 6H(2)O/KI/H(2)O/CH(3)CN:a new alternate system for dehydration of oximes and amides in hydrated media[J]. Journal of Organic Chemistry, 2002, 67(20):7138-7139.
[11] Daisuke Shouro, Yukinori Moriya, Tsuyoshi Nakajima, et al. Mesoporous silica FSM-16 catalysts modified with various oxides for the vapor-phase Beckmann rearrangement of cyclohexanone oxime[J]. APPlied Catalysis A:General,2000, 198:275-282.
[12] Sato H. Characteristics of ultrasonic dispersion of carbon nanotubes aided by antifoam[J]. Catalysis Review Science Engineering, 1997, 39(4):395-424.
[13]尹双凤,徐柏庆.环己酮肟在改性氧化锆催化剂上的Beckmann重排反应Ⅴ.活化焙烧温度对B2O3/ZrO2催化剂的影响[J].催化学报, 2002, 23(6):507-512.
[14]陶伟川,毛东森,陈庆龄,等. Silicalite-1的后处理对其催化环己酮肟气相Beckmann重排反应性能的影响[J].催化学报, 2005, 26(5):417-422.
[15]谢祎.固体磺酸催化环己酮肟液相贝克曼重排制备己内酰胺工艺研究[D].湘潭:湘潭大学, 2016.
[16]周云, Satmon John,陈亨权,等. Amberlyst 36磺酸树脂催化环己酮肟液相重排制己内酰胺[J].合成纤维工业,2016,(3):11-15.
[17] Li D, Shi F, Guo S, et al. Highly efficient Beckmann rearrangement and dehydration of oximes[J]. Cheminform,2005, 36(20):671-674.
[18]贾金锋,隗小山,廖有贵,等.三聚氯氰催化液相重排合成ε-己内酰胺[J].化工技术与开发, 2017, 46(5):25-28.
[19] Zanger M. Synthesis of tetrahydrobenzazepinesulfonamides and their rearrangement to diarylsulfones[J]. Synthetic Communications, 2006, 36(3):355-363.
[20]李曹龙,王洪林,刘光恒.离子液体系中催化环己酮肟重排反应的研究[J].云南化工, 2004, 31(2):4-6.
[21]李红艳,李凌飞,王智慧.离子液体催化反应研究进展[J].黑龙江科技信息, 2017,(14):25-25.
[22]闫华,张红梅,张丽静,等.离子液体研究进展[J].山东化工, 2016, 45(23):55-57.
[23]郭术,邓友全.室温离子液体与固体酸复合催化体系中环己酮肟Beckmann重排反应[C].全国催化学术会议,杭州, 2002.
[24]赵江琨,王荷芳,王延吉,等.酸性离子液体-ZnCl2催化环己酮肟液相Beckmann重排反应[J].高校化学工程学报, 2011, 25(5):838-843.
[25]彭家建,邓友全.离子液体系中催化环己酮肟重排制己内酰胺[J].石油化工, 2001, 30(2):91-92.
[26]张伟,吴巍,张树忠,等.[bmim][BF4]离子液体中PCl3催化的液相贝克曼重排[J].过程工程学报, 2004, 4(3):261-264.
[27] Feng J C, Liu B, Dai L, et al. One-step Beckmann rearrangement from ketones and hydroxylamine in dry media under microwave irradiation[J].中国化学快报:英文版,1998, 9(9):795-796.
[28]程庆彦,朱响林,王延吉,等.超声波辐射P2O5催化环己酮肟液相贝克曼重排合成己内酰胺[J].高校化学工程学报, 2017, 31(1):58-66.
[29] Li Y, Wang K, Qin K, et al. Beckmann rearrangement reaction of cyclohexanone oxime in sub/supercritical water:Byproduct and selectivity[J]. Rsc Advances, 2015, 5(32):25365-25371.