N-羟基邻苯二甲酰亚胺与 8-羟基喹啉氧钒 (IV) 配合物协同催化分子氧氧化乙苯

doi:10.1016/S1872-2067(10)60255-0

催化学报 ›› 2011, Vol. 32 ›› Issue (8): 1342-1348.DOI: 10.1016/S1872-2067(10)60255-0

N-羟基邻苯二甲酰亚胺与 8-羟基喹啉氧钒 (IV) 配合物协同催化分子氧氧化乙苯

秦金伟, 伏再辉*, 刘亚纯, 何乡陵, 张德喜, 吴文锋, 王彦龙, 龚兴浪, 邓晓林, 武海涛, 邹艳红, 喻宁亚, 尹笃林

湖南师范大学化学化工学院, 湖南省资源精细化与先进材料重点实验室, 化学生物学和中药分析教育部重点实验室, 湖南长沙 410081

收稿日期:2011-02-28 修回日期:2011-05-13 出版日期:2011-08-05 发布日期:2014-12-26

Aerobic Oxidation of Ethylbenzene Co-catalyzed by N-Hydroxyphthalimide and Oxobis(8-Quinolinolato) Vanadium (IV) Complexes

QIN Jinwei, FU Zaihui*, LIU Yachun, HE Xiangling, ZHANG Dexi, WU Wenfeng, WANG Yanlong, GONG Xinglang, DENG Xiaolin, WU Haitao, ZOU Yanhong, YU Ningya, YIN Dulin

Key Laboratory of Resoruce Fine-Processing and advanced materials of Hunan Province and Key Laboratory of Chemical Biology and Traditional Chinese Medicine Research Ministry of Education of China, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha 410081, Hunan, China

Received:2011-02-28 Revised:2011-05-13 Online:2011-08-05 Published:2014-12-26

摘要/Abstract

摘要： 研究了钒化合物对 N-羟基邻苯二甲酰亚胺 (NHPI) 催化分子氧氧化乙苯反应中的调变效应. 结果表明, 由 8-羟基喹啉及其衍生物与乙酰丙酮氧钒 (IV) 配位制得的 8-羟基喹啉氧钒 (IV) 配合物的催化活性比乙酰丙酮氧钒 (IV), NH4VO3 和 V2O5 的高. 在优化的反应条件下, 乙苯转化率和苯乙酮选择性可分别达 60%~69% 和 97%. 基于液体反应的紫外光谱, 推测钒催化剂能够促进 NHPI 转变为 N-氧基邻苯二甲酰亚胺自由基和 1-苯基过氧化氢转变为苯乙酮.

关键词: N-羟基邻苯二甲酰亚胺, 8-羟基喹啉氧钒 (IV), 需氧氧化, 乙苯, 苯乙酮

Abstract: The mediation effect of vanadium compounds on the N-hydroxyphthalimide (NHPI)-catalyzed aerobic oxidation of ethylbenzene (EB) was investigated at 90 °C in benzonitrile. Among the vanadium mediators examined, a series of oxobis(8-quinolinolato) vanadium (IV) complexes (V^IVOQ₂), which were prepared by the coordination of 8-hydroxyquinoline or its derivatives with oxobis(2,4-pentanedionate) vanadium (IV) (V^IVO(acac)₂) showed a better mediation effect than V^IVO(acac)₂, NH₄VO₃, and V₂O₅ and they gave about 60%–69% EB conversion and 97% of acetophenone (AcPO) selectivity under optimum reaction conditions. This is due to the dual catalysis effects of these V mediators on the transformation of NHPI to the phthalimide-N-oxyl (PINO) radical and the decomposition of 1-phenylethyl hydroperoxide to AcPO, as supported by UV-Vis spectral characterization.

Key words: n-hydroxyphthalimide, oxobis(8-quinolinolato) vanadium (IV), aerobic oxidation, ethylbenzene, acetophenone

秦金伟, 伏再辉, 刘亚纯, 何乡陵, 张德喜, 吴文锋, 王彦龙, 龚兴浪, 邓晓林, 武海涛, 邹艳红, 喻宁亚, 尹笃林. N-羟基邻苯二甲酰亚胺与 8-羟基喹啉氧钒 (IV) 配合物协同催化分子氧氧化乙苯[J]. 催化学报, 2011, 32(8): 1342-1348.

QIN Jin-Wei, FU Zai-Hui, LIU Ya-Chun, HE Xiang-Ling, ZHANG De-Xi, WU Wen-Feng, WANG Yan-Long, GONG Xing-Lang, DENG Xiao-Lin, WU Hai-Tao, ZOU Yan-Hong, YU Ning-Ya, YIN Du-Lin. Aerobic Oxidation of Ethylbenzene Co-catalyzed by N-Hydroxyphthalimide and Oxobis(8-Quinolinolato) Vanadium (IV) Complexes[J]. Chinese Journal of Catalysis, 2011, 32(8): 1342-1348.

×
扫码分享

导出引用管理器 EndNote|Ris|BibTeX

链接本文: https://www.cjcatal.com/CN/10.1016/S1872-2067(10)60255-0

https://www.cjcatal.com/CN/Y2011/V32/I8/1342

参考文献

1Lu C L, Fu Z H, Liu Y C, Liu F L, Wu Y Y, Qin J W, He X L, Yin D L. J Mol Catal A, 2010, 331: 106
2Vetrivel S, Pandurangan A. J Mol Catal A, 2004, 217: 165
3George K, Sugunan S. Catal Commun, 2008, 9: 2149
4Klopstra M, Hage R, Kellogg R M, Feringa B L. Tetrahedron Lett, 2003, 44: 4581
5Balland V, Mathieu D, Pons-Y-Moll N, Bartoli J F, Banse F, Battioni P, Girerd J J, Mansuy D. J Mol Catal A, 2004, 215: 81
6Maurya M R, Arya A, Adao P, Costa Pessoa J. Appl Catal A, 2008, 351: 239
7Schuchardt U, Cardoso D, Sercheli R, Pereira R, Dacruz R S, Guerreiro M C, Mandelli D, Spinace E V, Pires E L. Appl Catal A, 2001, 211: 1
8Ishii Y, Nakayama K, Takeno M, Sakaguchi S, Iwahama T, Nishiyama Y. J Org Chem, 1995, 60: 3934
9Ma H, Xu J, Chen C, Zhang Q H, Ning J B, Miao H, Zhou L P, Li X Q. Catal Lett, 2007, 113: 3
10Recupero F, Punta C. Chem Rev, 2007, 107: 3800
11Iwahama T, Hatta G, Sakaguchi S, Ishii Y. Chem Commun, 2000: 163
12Ishii Y, Sakaguchi S, Iwahama T. Adv Synth Catal, 2001, 343: 393
13Yoshino Y, Hayashi Y, Iwahama T, Sakaguchi S, Ishii Y. J Org Chem, 1997, 62: 6810
14Shibamoto A, Sakaguchi S, Ishii Y. Org Process Res Dev, 2000, 4: 505
15Sakaguchi S, Shimamoto A, Ishii Y. Chem Commun, 2002: 180
16Sawatari N, Yokota T, Sakaguchi S, Ishii Y. J Org Chem, 2001, 66: 7889
17Wentzel B B, Donners M P J, Alsters P L, Feiters M C, Nolte R J M. Tetrahedron, 2000, 56: 7797
18Karimi B, Rajabi J. Synthesis, 2003: 2373
19Cecchetto A, Minisci F, Recupero F, Fontana F, Pedulli G F. Tetrahedron Lett, 2002, 43: 3605
20Kagayama T, Sakaguchi S, Ishii Y. Tetrahedron Lett, 2005, 46: 3687
21Ma H, Xu J, Zhang Q H, Miao H, Wu W H. Catal Commun, 2007, 8: 27
22Yang G Y, Ma Y F, Xu J. J Am Chem Soc, 2004, 126: 10542
23Tong X L, Xu J, Miao H. Adv Synth Catal, 2005, 347: 1953
24Yang X M, Zhou L P, Chen Y, Chen C, Su Y L, Miao H, Xu J. Catal Commun, 2009, 11: 171
25Zheng G X, Liu C H, Wang Q F, Wang M Y, Yang G Y. Adv Synth Catal, 2009, 351: 2638
26Fukuda O, Sakaguchi S, Ishii Y. Tetrahedron Lett, 2001, 42: 3479
27Sakaguchi S, Hirabayashi T, Ishii Y. Chem Commun, 2002: 516
28Minisci F, Recupero F, Gambarotti C, Punta C, Paganelli R. Tetrahedron Lett, 2003, 44: 6919
29Sakaguchi S, Nishiwaki Y, Kitamura T, Ishii Y. Angew Chem, Int Ed, 2001, 40: 222
30Matsunaka K, Iwahama T, Sakaguchi S, Ishii Y. Tetrahedron Lett, 1999, 40: 2165
31Ishii Y, Iwahama T, Sakaguchi S, Nakayama K, Nishiyama Y. J Org Chem, 1996, 61: 4520
32Sheldon R A, Arends I W C E, Reedijk J. Adv Synth Catal, 2004, 346: 1051
33Conte V, Bortolini O. In: Rappoport Z Ed. The Chemistry of Peroxides-Transition Metal Peroxides, Synthesis and Rolein Oxidation Reactions. New York: Wiley, 2006. 1053
34Figiel P J, Sobczak J M. J Catal, 2009, 263: 167
35Kantama M L, Neelima B, Reddya Ch V, Chaudhuri M K, Dehury S K. Catal Lett, 2004, 95: 19
36Wuilloud R G, Wuilloud J C, Olsina R A, Martinez L D. Analyst, 2001, 126: 715
37Evans S, Smith J R L. J Chem Soc, Perkin Trans 2, 2001: 174
38Maurya M R, Chandrakar A K, Chand S. J Mol Catal A, 2007, 270: 225
39Saha B, Koshino N, Espenson J H. J Phys Chem A, 2004, 108: 425
40Maurya M R, Kumar A. J Mol Catal A, 2006, 250: 190
41Graf R. Ann Chem, 1952, 578: 50

[1]	Igor B. Krylov, Elena R. Lopat’eva, Irina R. Subbotina, Gennady I. Nikishin, Bing Yu, Alexander O. Terent’ev. 多相/均相TiO₂/N-羟酰亚胺混合体系中可见光诱导分子氧可控光催化氧化苄基反应[J]. 催化学报, 2021, 42(10): 1700-1711.
[2]	王振东, Magdalena O. Cichocka, 罗翼, 张斌, 孙洪敏, 唐颐, 杨为民. 层剥离MWW结构分子筛的直接可控合成[J]. 催化学报, 2020, 41(7): 1062-1066.
[3]	Nagaraju Pasupulety, Muhammad A. Daous, Abdulrahim A. Al-Zahrani, Hafedh Driss, Lachezar A. Petrov. 用于乙苯氧化脱氢制苯乙烯铝-硼催化剂:铝硼组成及制备方法对催化剂性能的影响[J]. 催化学报, 2019, 40(11): 1758-1765.
[4]	章冠群, 王冬娥, 冯培, 石松, 王从新, 郑安达, 吕广, 田志坚. 含超微氧化亚钴颗粒Beta分子筛的合成及其催化乙苯氧化性能[J]. 催化学报, 2017, 38(7): 1207-1215.
[5]	陈可先, 谢海英. 高效多羟胺有机催化剂选择性催化分子氧氧化研究进展[J]. 催化学报, 2017, 38(4): 625-635.
[6]	付玲玲, 鲁怡娟, 刘志刚, 朱润良. 以卟啉为前驱体制备的M-N-C(M=Co,Fe,Mn)催化剂中不同过渡金属中心对催化乙苯氧化反应的影响[J]. 催化学报, 2016, 37(3): 398-404.
[7]	杨为民, 王振东, 孙洪敏, 张斌. 乙苯工艺技术开发及工业应用进展[J]. 催化学报, 2016, 37(1): 16-26.
[8]	田涛, 刘英, 张勋高. 氧化铜修饰羟基磷灰石负载金对醇类需氧氧化的双金属协同催化[J]. 催化学报, 2015, 36(8): 1358-1364.
[9]	王连月, 陈波, 任兰会, 张恒耘, 吕迎, 高爽. 温和条件下钒催化氧化胺、醇和胺直接合成亚胺[J]. 催化学报, 2015, 36(1): 19-23.
[10]	唐沛, 高勇军, 杨敬贺, 李文静, 赵华博, 马丁. 氮掺杂石墨烯的生长机理及其在乙苯选择性氧化中的应用[J]. 催化学报, 2014, 35(6): 922-928.
[11]	张淑芳, 苗成霞, 徐大乾, 孙伟, 夏春谷. 基于四氮配体的铜配合物/TEMPO催化的苄醇与烯丙基醇的氧化反应[J]. 催化学报, 2014, 35(11): 1864-1873.
[12]	慕旭宏, 王殿中, 王永睿, 林民, 程时标, 舒兴田. 纳米分子筛在炼油和石油化工中的应用[J]. 催化学报, 2013, 34(1): 69-79.
[13]	杨朝芬, 杨俊, 孙晓东, 朱艳琴, 王齐1, 陈华. (1S,2S)-1,2-二苯基乙二胺修饰 Ir/SiO₂ 催化苯乙酮及其衍生物不对称加氢[J]. 催化学报, 2012, 33(7): 1154-1160.
[14]	汪薇, 宗敏华, 娄文勇. 不同反应体系中 (S)-1-(4-甲氧基)-苯基乙醇的不对称生物合成[J]. 催化学报, 2011, 32(6): 1003-1010.
[15]	田鹏, 高保娇, 陈英军. 在交联聚苯乙烯微球表面同步合成与固载吡啶基卟啉及固载化钴卟啉的催化氧化性能[J]. 催化学报, 2011, 32(3): 483-489.

N-羟基邻苯二甲酰亚胺与 8-羟基喹啉氧钒 (IV) 配合物协同催化分子氧氧化乙苯

Aerobic Oxidation of Ethylbenzene Co-catalyzed by N-Hydroxyphthalimide and Oxobis(8-Quinolinolato) Vanadium (IV) Complexes

PDF

可视化

摘要/Abstract

引用本文

使用本文

扫码分享

参考文献

相关文章 15

编辑推荐

Metrics