Epoxidation of α,β-Unsaturated Ketones Catalyzed by Schiff Base Functionalized MCM-41 and Potassium Carbonate

doi:10.3724/SP.J.1095.2013.30061

Chinese Journal of Applied Chemistry

• Full Papers • Previous Articles Next Articles

Epoxidation of α,β-Unsaturated Ketones Catalyzed by Schiff Base Functionalized MCM-41 and Potassium Carbonate

ZHANG Weidong¹, HE Jun², GONG Haiwei¹, ZHANG Peng¹, XIE Zhengfeng^1*

1.Key Laboratory of Oil & Gas Fine Chemicals,Ministry of Education & Xinjiang Uyghur Autonomous Region,College of Chemistry and Chemical Engineering,Xinjiang University,Urumqi 830046,China;
2.The Oil Refinery of Petrochina Dushanzi Petrochemical Company,Dushanzi 833600,China

Received:2013-01-25 Revised:2013-03-25 Published:2013-11-10 Online:2013-11-10
Supported by:

Abstract

Abstract: Mesoporous molecular sieves MCM-41 supported Schiff base was prepared from MCM-41, 3-chloropropyltriethoxysilane, dis-thiocarbohydrazone and salicylide. Both as-prepared supported catalyst and K2CO3 were used to catalyze the epoxidation of α,β-unsaturated ketones in the presence of H2O2. All products from these oxidations were characterized by 1H NMR and IR. The effects of reaction conditions such as metal salts, solvents, reaction temperature, the loading of catalyst, and reaction time on the oxidation reaction were investigated. It was found that the epoxidation products of α,β-unsaturated ketones were easily obtained with excellent yields(up to 93%) at room temperature in a short time. Especially, the heterogeneous catalyst can be reused four times without significant loss of its catalytic activity.

Key words: MCM-41 supported Schiff base, hydrogen peroxide, catalytic composite,epoxidation of &, alpha,&beta-unsaturated ketones, potassium carbonate

CLC Number:

O643.3

ZHANG Weidong, HE Jun, GONG Haiwei, ZHANG Peng, XIE Zhengfeng. Epoxidation of α,β-Unsaturated Ketones Catalyzed by Schiff Base Functionalized MCM-41 and Potassium Carbonate[J]. Chinese Journal of Applied Chemistry, DOI: 10.3724/SP.J.1095.2013.30061.

References

[1] Rink R,Lutje Spelberg J H,Pieters R J,et al. Mutation of Tyrosine Residues Involved in the Alkylation Half Reaction of Epoxide Hydrolase from Agrobacterium Radiobacter AD1 Results in Improved Enantioselectivity[J]. J Am Chem Soc,1999,121:7417-7418.

[2] Koreeda M,Gopalaswamy R. Regio- and Stereocontrolled Synthesis of the Bay-Region anti-Diol Epoxide Metabolites of the Potent Carcinogens Benzo[ɑ]pyrene and 7,12-Dimethylbenz[ɑ]anthracene[J]. J Am Chem Soc,1995,117:10595-10596.

[3] Lau E Y,Newby Z E,Bruice T C. A Theoretical Examination of the Acid-Catalyzed and Noncatalyzed Ring-Opening Reaction of an Oxirane by Nucleophilic Addition of Acetate. Implications to Epoxide Hydrolases[J]. J Am Chem Soc,2001,123:3350-3357.

[4] Takayuki H,Michiko N,Tomoo M,et al. Highly Efficient Epoxidation of α,β-Unsaturated Ketones by Hydrogen Peroxide with a Base Hydrotalcite Catalyst Prepared from Metal Oxides[J]. Tetrahedron Lett,2002,43:6229-6232.

[5] Smit L I,Howard K L.The Action of Aliphatic Diazo Compounds upon α,β-Unsaturated Ketones[J]. J Am Chem Soc,1943,65:159-164.

[6] Lygo B,Wainwright P G. Asymmetric Phase-Transfer Mediated Epoxidation of α,β-Unsaturated Ketones Using Catalysts Derived from Cinchona Alkaloids[J]. Tetrahedron Lett,1998,39:1599-1602.

[7] Ooi T,Ohara D,Maruoka K,et al. Design of New Chiral Phase-Transfer Catalysts with Dual Functions for Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones[J]. J Am Chem Soc,2004,126:6844-6845.

[8] Wu F H,Li H M,Deng L,et al. Construction of Quaternary Stereocenters by Efficient and Practical Conjugate Additions to α,β-Unsaturated Ketones with a Chiral Organic Catalyst[J]. Angew Chem,2006,118:961-964.

[9] Righi G,Achille R D. Regioselective Opening of 3-Substituted N-Ethoxycarbonyl Aziridine-2-Carboxylates with Metal Halides Toward the Preparation of α and β-Amino Acids[J]. Tetrahedron Lett,1996,38:6893-6896.

[10] Liu X,Li Y,Wang G,et al. Effective and Recyclable Dendritic Ligands for the Enantioselective Epoxidation of Enones[J]. Tetrahedron:Asymmetry,2006,17:750-755.

[11] ZHANG Fuli,TANG Kun. Epoxidation of Cyclohexene Catalyzed by Metal Iron Schiff Base Complexes[J]. Chinese J Org Chem,2011,31:921-924(in Chinese).

张付利，汤昆. Schiff 碱铁配合物催化环己烯环氧化[J]. 有机化学，2011,31:921-924.

[12] Liu X Y,Li Y W,Wang G Y,et al. Effective and Recyclable Dendritic Ligands for the Enantioselective Epoxidation of Enones[J]. Tetrahedron:Asymmetry,2006,17:750-755.

[13] Lattanzi A. Enantioselective Epoxidation of α,β-Enones Promoted by α,α-Diphenyl-L-prolinol as Bifunctional Organocatalyst[J]. Org Lett,2005,7:2579-2582.

[14] Lattanzi A,Russo A. Diaryl-2-pyrrolidinemethanols Catalyzed Enantioselective Epoxidation of α,β-Enones:New Insight into the Effect of Structural Modification of the Catalyst on Reaction Efficiency[J]. Tetrahedron,2006,62:12264-12269.

[15] Lu J,Xu Y H,Liu F,et al Enantioselective Epoxidation of α,β-Enones Promoted by(1R,3S,4S)-2-Azanorbornyl-3-methanol as an Organocatalyst[J]. Tetrahedron Lett,2008,49:6007-6008.

[16] Makó A,Rapi Z,Keglevich G,et al. Asymmetric Epoxidation of Substituted Chalcones and Chalcone Analogues Catalyzed by α-D-glucose- and α-D-mannose-based Crown Ethers[J]. Tetrahedron:Asymmetry,2010,21:919-925.

[17] Wu M,Wang S F,Xia C G,et al. Asymmetric Epoxidation of Olefins with Chiral Bioinspired Manganese Complexes[J]. Org Lett,2009,11:3622-3625.

[18] Okamoto S,Takano K,Ishikawa T,et al. Activity and Behavior of Imidazolium Salts as a Phase Transfer Catalyst for a Liquid-liquid Phase System[J]. Tetrahedron Lett,2006,47:8055-8058.

[19] Hori K,Tamura M,Tani K,et al. Asymmetric Epoxidation Catalyzed by Novel Azacrown Ether-type Chiral Quaternary Ammonium Salts under Phase-transfer Catalytic Conditions[J]. Tetrahedron Lett,2006,47:3115-3118.

[20] OUYANG Xiaoyue. Studies on the Oxidation of Olefins with Green Oxidants[D]. Hefei:University of Science and Technology of China,2006(in Chinese).

欧阳小月. 绿色氧化剂对烯烃类的氧化反应研究[D]. 合肥:中国科技大学，2006.

[21] Yoo M S,Kim D G,Ha M W,et al. Synthesis of (αR,βS)-Epoxyketones by Asymmetric Epoxidation of Chalcones with Cinchona Phase-transfer Catalysts[J]. Tetrahedron Lett,2010,51:5601-5603.

[22] ZHANG Aiping,GAO Shuang,XU Jie,et al. Green Epoxidation of α,β-Unsaturated Ketones[J]. Chinese J Catal,2009,30:69-72(in Chinese).

张爱平,高爽,徐杰,等. α,β-不饱和酮的绿色环氧化[J]. 催化学报,2009,30:69-72.

[23] Geng X L,Wang Z,Li X Q,et al. A Simple Method for Epoxidation of Olefins Using Sodium Chlorite as an Oxidant without a Catalyst[J]. J Org Chem,2005,70:9610-9613.

[24] Porter M J,SkidmoreJ. Asymmetric Epoxidation of Electron-deficient Olefins[J]. Chem Commun,2000,14:1215-1225.

[25] Lee A,Kim W,Lee J,et al. Heterogeneous Asymmetric Nitro-Mannich Reaction Using a Bis(oxazoline) Ligand Grafted on Mesoporous Silica[J]. Tetrahedron:Asymmetry,2004,15:2595-2598.

[26] Yong Y L,Wan N N,Xie Z F,et al. Synthesis of Bis(indolyl) Methanes Catalyzed by Schiff Base-Cu(Ⅱ) Complex[J]. Chinese Chem Lett,2011,22:1071-1074.

[27] CHEN Yongcheng,CHEN Yuanyuan,XIE Zhengfeng,et al. Friedel-Crafts Reaction of Indoles with Nitroalkenes Catalyzed by Yb(OTf)3[J]. Chinese J Org Chem,2011,31:1672-1677(in Chinese).

陈永成，陈圆圆，解正峰,等. 三氟甲磺酸镱催化吲哚与硝基烯Friedel-Crafts反应的研究[J]. 有机化学，2011,31:1672-1677.

[28] Wan N N,Hui Y H,Xie Z F,et al. Friedel-Crafts Alkylation of Indoles with Nitroalkenes Catalyzed by Zn(Ⅱ)-Thiourea Complex[J]. Chinese J Chem,2012,30:311-315.

[29] ZHOU Guangpeng,YU Lei,XIE Zhengfeng,et al. Study on the Epoxidation of α,β-Unsaturated Ketones Catalyzed by MCM-41 Supported Schiff Base[J]. Acta Chim Sin,2012,70(11):1289-1294(in Chinese).

周广鹏，余蕾，解正峰,等. MCM-41负载席夫碱催化α,β-不饱和酮的环氧化反应研究[J]. 化学学报,2012,70(11):1289-1294.

[30] Oliveira P,Machado A,Ramos A M,et al. MCM-41 Anchored Manganese Salen Complexes as Catalysts for Limonene Oxidation[J]. Micropor Mesopor Mater,2009,120:432-440.

[31] LI Zaiguo,WANG Qingmin,HUANG Junmin. Preparation of Organic Intermediates[M]. Second Edition. Beijing:Chemical Industry Press,1996:51(in Chinese).

李在国,汪清民,黄君珉. 有机中间体制备[M]. 第2版. 北京:化学工业出版社,1996:51.

[32] Li Y W,Liu X Y,Zhao G,et al. 4-Substituted-α,α-diaryl-prolinols Improve the Enantioselective Catalytic Epoxidation of α,β-Enones[J]. J Org Chem,2007,72:288-291.

Epoxidation of α,β-Unsaturated Ketones Catalyzed by Schiff Base Functionalized MCM-41 and Potassium Carbonate

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Ao YU, Guo-Ming MA, Long-Tao ZHU, Ping PENG, Fang-Fang LI. Electrochemical Reduction of Carbon Dioxide to Carbon Materials for Two⁃Electron Oxygen Reduction Reaction [J]. Chinese Journal of Applied Chemistry, 2022, 39(4): 657-665.
[2]	SUN Li'na,LI Yan,GUO Hantao,HUANG Tingting,YAO Bixia,WENG Wen. Preparation of Nitrogen and Iron Co-doped Carbon Nanoparticles and Their Applications in Detection of Hydrogen Peroxide and Glucose [J]. Chinese Journal of Applied Chemistry, 2020, 37(3): 350-358.
[3]	Xin SHI,Chuanzhi LIU,Ping GONG,wei LI,Yue HOU. Hydrogen Peroxide and Glucose Sensitive Colorimetric Method Based on Deuterohemin-Ala His Thr Val Glu Lys [J]. Chinese Journal of Applied Chemistry, 2019, 36(7): 847-854.
[4]	LIU Di,TONG Huan,YUAN Linjie,ZHANG Zipeng,MA Kangfu,YUAN Lin,ZHANG Wanyu,CHEN Lidong,WANG Xiangsheng,GUO Hongchen. Preparation of High Activity Oxidative Desulfurization Catalyst from Phosphomolybdic Acid and Titania Silica Nanocomposite [J]. Chinese Journal of Applied Chemistry, 2018, 35(11): 1351-1356.
[5]	CHEN Lidong, TONG Huan, WANG Xuyang, SONG Pengyue, LIU Di, JI Yanqing, YUE Qian, DING Wei, JIA Yixin, CHEN Yongying, JIANG Chunjie. Preparation of High Activity Oxidative DesulfurizationCatalyst with Polycation and Heteropolyanion Keggin Structure [J]. Chinese Journal of Applied Chemistry, 2017, 34(11): 1301-1306.
[6]	XIAO Yi, YANG Xiya, JIANG Xiaoying, SHI Huizhen, HUANG Hongmei, YIN Dulin, MAO Liqiu. Oxidation of Isoeugenol with Hydrogen Peroxide Catalyzed by Nano/Microscale Copper Metal-Organic Frameworks [J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1168-1174.
[7]	SONG Pengyue, ZHU Jiang, YU Bohao, WANG Xuyang, YANG Jiao, LI Yumeng, LI Chuanpeng, YANG Xiaoyu, CHEN Lidong, JIANG Chunjie. Performance of Phosphotungstic Acid-Urea/Ferroferric Oxide Magnetic Oxidative Desulfurization Catalyst [J]. Chinese Journal of Applied Chemistry, 2015, 32(3): 317-321.
[8]	ZHOU Shuolin, XU Qiong, XIAO Jiafu, LIU Wei, YIN Dulin*. Investigation of UV Shielding Property of TiO2 Pigments by H2O2 Decomposition Kinetics [J]. Chinese Journal of Applied Chemistry, 2014, 31(10): 1234-1236.
[9]	LUO Dong, GAO Meixiang, MAO Liqiu*, YIN Dulin. Oxidation of Cyclohexylamine to Cyclohexanone Oxime Catalyzed by NaY Zeolite Molecular Sieves [J]. Chinese Journal of Applied Chemistry, 2013, 30(12): 1443-1448.
[10]	ZHANG Peipei, WANG Aijun, LIU Xueyan, ZHU Hongqiao, DU Junfang, CHEN Xuan, FENG Jiuju*. Layer-by-layer Self-assembled Prussian Blue Modified Electrode and Its Application for the Detection of Hydrogen Peroxide [J]. Chinese Journal of Applied Chemistry, 2012, 29(05): 585-590.
[11]	LIU Caisheng1, QIAO Haiyan2, GU Ningyu1, TANG Jilin2. Determination of Hydrogen Peroxide Using 4-(2-Pyridylazo)-Resorcinol Polymer Film Modified Glassy Carbon Electrode [J]. Chinese Journal of Applied Chemistry, 2012, 29(02): 216-221.
[12]	HUA Yingjie, WANG Chongtai*, SUN Zhenfan, LIU Yanling, ZHOU Changsheng. Photocatalytic Degradation of Aniline by a Novel Photo-Fenton-Like System Consisting of PW₁₁O₃₉Fe(Ⅲ)(H₂O)^4-/H₂O₂ [J]. Chinese Journal of Applied Chemistry, 2012, 29(01): 63-68.
[13]	LIU Yutang*, PAN Kexue, LIU Chengbin. Preparation of Poly(anthranilic acid)-Copper Particles Modified Electrode and Its Electrochemical Preparation of Poly(anthranilic acid)-Copper Composite Modified Electrode and Its Electrochemical Properties [J]. Chinese Journal of Applied Chemistry, 2011, 28(09): 1052-1057.
[14]	ZHAO Su-Cai, ZHANG Mei, WAN Ling-Li, SONG Yong-Hai, WANG Li*. Preparation and Electrocatalytic Behaviors of GCE/DNA/PFS/RTIL/HRP Modified Electrode [J]. Chinese Journal of Applied Chemistry, 2011, 28(03): 333-337.
[15]	ZHU Dan-Dan, ZHANG Ya-Dong*, WANG Zhen-Xing. A Solvent-free Method for Preparation of 1,2-Epoxycyclopentane [J]. Chinese Journal of Applied Chemistry, 2010, 27(12): 1392-1395.