中文
Announcement
More
Progress in Chemistry 2012, Vol. 24 Issue (01): 17-30 Previous Articles   Next Articles

Catalysts for Vapor-Phase Selective Hydrogenation of Crotonaldehyde to Crotyl Alcohol

Chen Ping, Xie Guanqun, Luo Mengfei*   

  1. Zhejiang Key Laboratory of Reactive Chemistry on Solid Surfaces, Institute of Physical Chemistry, Zhejiang Normal University, Jinhua 321004, China
  • Received: Revised: Online: Published:
PDF ( 1132 ) Cited
Export

EndNote

Ris

BibTeX

The vapor-phase selective hydrogenation of crotonaldehyde, a classical α, β-unsaturated aldehyde, to crotyl alcohol over heterogeneous catalysts is an appealing green process of great importance from both industrial and academic points of view. This paper reviews the latest progresses of the heterogeneous catalysts for selective hydrogenation of crotonaldehyde to crotyl alcohol in the past ten years. Noble metal catalysts such as platinum, silver, gold and iridium and non-noble metal catalysts such as cobalt and copper employed for selective hydrogenation of crotonaldehyde are summarized. The parameters influencing the catalytic behaviors of the catalyst system such as active sites, metal particle size, support type, promoters are discussed. Also, catalyst deactivation and reaction mechanism are investigated. Finally, the current problems of the vapor-phase selective hydrogenation of crotonaldehyde are summarized and development trend of catalyst systems for this reaction is proposed. It is pointed out that the vapor-phase selective hydrogenation of crotonaldehyde over non-noble metal catalysts will be a main research direction because its much lower cost compared to the noble metal catalysts. As the catalyst deactivation is the main obstacle for this reaction, the research should be focused on the understanding of the reaction and deactivation mechanism. Contents
1 Introduction
2 Noble metal catalysts
2.1 Platinum catalysts
2.2 Gold catalysts
2.3 Other noble metal catalysts
3 Non-noble metal catalysts
3.1 Cobalt catalysts
3.2 Copper catalysts
4 Reaction mechanisms
5 Deactivation of catalysts
6 Conclusions and outlook

CLC Number: 

[1] Mertens P G N, Cuypers F, Vandezande P, Ye X P, Verpoort F, Vankelecom I F J, De Vos D E. Appl. Catal. A: Gen., 2007, 325: 130-139

[2] Mäki-Arvela P, Hájek J, Salmi T, Murzin D Y. Appl. Catal. A: Gen., 2005, 292: 1-49

[3] Grass M E, Rioux R M, Somorjai G A. Catal. Lett., 2009, 128: 1-8

[4] Englisch M, Jentys A, Lercher J A. J. Catal., 1997, 166: 25-35

[5] Mohr C, Hofmeister H, Radnik J, Claus P. J. Am. Chem. Soc., 2003, 125: 1905-1911

[6] Ponec V. Appl. Catal. A: Gen., 1997, 149: 27-48

[7] Delbecq F, Sautet P. Catal. Lett., 1994, 28: 89-98

[8] Reyes P, Rojas H, Fierro J L G. J. Mol. Catal. A: Chem., 2003, 203: 203-211

[9] 黄朋勉(Huang P M), 刘自力(Liu Z L), 郑淼(Zheng M ), 谢先梅(Xie X M). 工业催化(Industrial Catalysis), 2003, 11 (6): 27-30

[10] Gebauer-Henke E, Grams J, Szubiakiewicz E, Farbotko J, Touroude R, Rynkowski J. J. Catal., 2007, 250: 195-208

[11] Ammari F, Lamotte J, Touroude R. J. Catal., 2004, 221: 32-42

[12] ConcepciońP, Corma A, Silvestre-Albero J, Franco V, Chane-Ching J Y. J. Am. Chem. Soc., 2004, 126: 5523-5532

[13] Liberková K, Touroude R. J. Mol. Catal. A: Chem., 2002, 180: 221-230

[14] Jin L Y, Tao L P, Liu X J, Xie G Q, Lu J Q, Luo M F. Indian J. Chem., 2010, 49A: 49-53

[15] Serrano-Ruiz J C, Luettich J, Sepúlveda-Escribano A, Rodríguez-Reinoso F. J. Catal., 2006, 241: 45-55

[16] 郑海影(Zheng H Y), 谢冠群(Xie G Q), 王晓霞(Wang X X), 金凌云(Jin L Y), 罗孟飞(Luo M F). 物理化学学报(Acta Physico-Chimica Sinica), 2010, 26 (12): 3273-3277

[17] Ruppert A M, Paryjczak T. Appl. Catal. A: Gen., 2007, 320: 80-90

[18] 谢冠群(Xie G Q), 刘西敬(Liu X J), 鲁继青(Lu J Q), 李小年(Li X N), 罗孟飞(Luo M F). 中国稀土学报(Journal of the Chinese Society of Rare Earths), 2009, 27 (6): 756-760

[19] Kijeński J, Winiarek P. Appl. Catal. A: Gen., 2000, 193: L1-L4

[20] Wang X X, Zheng H Y, Liu X J, Xie G Q, Lu J Q, Jin L Y, Luo M F. Appl. Catal. A: Gen., 2010, 388: 134-140

[21] Huidobro A, Sepúlveda-Escribano A, Rodríguez-Reinoso F. J. Catal., 2002, 212: 94-103

[22] Silvestre-Albero J, Serrano-Ruiz J C, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Appl. Catal. A: Gen., 2005, 292: 244-251

[23] Wu J C S, Cheng T S, Lai C L. Appl. Catal. A: Gen., 2006, 314: 233-239

[24] Torres G C, Ledesma S D, Jablonski E L, de Miguel S R, Scelza O A. Catal. Today, 1999, 48: 65-72

[25] Mahata N, Goncalves F, Pereira M F R, Figueiredo J L. Appl. Catal. A: Gen., 2008, 339: 159-168

[26] Ruiz-Martínez J, Coloma F, Sepúlveda-Escribano A, Anderson J A, Rodríguez-Reinoso F. Catal. Today, 2008, 133/135: 35-41

[27] Ramos-Fernández E V, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Catal. Commun., 2008, 9: 1243-1246

[28] Silvestre-Albero J, Serrano-Ruiz J C, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Appl. Catal. A: Gen., 2008, 351: 16-23

[29] Silvestre-Albero J, Sepúlveda-Escribano A, Rodríguez-Reinoso F, Anderson J A. J. Catal., 2004, 223: 179-190

[30] Merlo A B, Santori G F, Sambeth J, Siria G J, Casella M L, Ferretti O A. Catal. Commun., 2006, 7: 204-208

[31] Consonni M, Jokic D, Murzin D Y, Touroude R. J. Catal., 1999, 188: 165-175

[32] Abid M, Touroude R. Catal. Lett., 2000, 69: 139-144

[33] Liberkova K, Touroude R, Murzin D Y. Chem. Eng. Sci., 2002, 57: 2519-2529

[34] Silvestre-Albero J, Coloma F, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Appl. Catal. A: Gen., 2006, 304: 159-167

[35] Wang D, Ammari F, Touroude R, Su D S, Schögl R. Catal. Today, 2009, 147: 224-230

[36] Ammari F, Milone C, Touroude R. J. Catal., 2005, 235: 1-9

[37] Bachiller-Baeza B, Guerrero-Ruiz A, Rodríguez-Ramos I. Appl. Catal. A: Gen., 2000, 192: 289-297

[38] 陈萍(Chen P), 谢冠群(Xie G Q), 郑海影(Zheng H Y), 朱琳(Zhu L), 罗孟飞(Luo M F). 催化学报(Chinese Journal of Catalysis), 2011, 32 (3): 513-519

[39] Abid M, Paul-Bonurcour V, Touroude R. Appl. Catal. A: Gen., 2006, 297: 48-59

[40] Claus P. Appl. Catal. A: Gen., 2005, 291: 222-229

[41] Bailie J J, Hutchings G J. Chem. Commun., 1999, 2151-2152

[42] Campo B, Volpe M, Ivanova S, Touroude R. J. Catal., 2006, 242: 162-171

[43] Wang M M, He L, Liu Y M, Cao Y, He H Y, Fan K N. Green Chem., 2011, 13: 602-607

[44] 谢冠群(Xie G Q), 刘西敬(Liu X J), 陶丽萍(Tao L P), 鲁继青(Lu J Q), 罗孟飞(Luo M F), 李小年(Li X N). 催化学报(Chinese Journal of Catalysis), 2009, 30 (6): 543-548

[45] Bailie J E, Abdullah H A, Anderson J A, Rochester C H, Richardson N V, Hodge N, Zhang J G, Burrows A, Kiely C J, Hutchings G J. Phys. Chem. Chem. Phys., 2001, 3: 4113-4121

[46] Zhu Y, Tian L, Zheng J, Pei Y, Xie S, Qiao M H, Fan K N. J. Catal., 2011, 281: 106-118

[47] 田莉(Tian L), 周功兵(Zhou G B), 李振华(Li Z H), 裴燕(Pei Y), 乔明华(Qiao M H), 范康年(Fan K N). 物理化学学报(Acta Physico-Chimica Sinica), 2011, 27 (4): 946-952

[48] Yang Q Y, Zhu Y, Tian L, Xie S H, Pei Y, Li H, Li H X, Qiao M H, Fan K N. Appl. Catal. A: Gen., 2009, 369: 67-76

[49] Zanella R, Louis C, Giorgio S, Touroude R. J. Catal., 2004, 223: 328-339

[50] Campo B, Petit C, Volpe M. J. Catal., 2008, 254: 71-78

[51] Hammer B, Norskov K. Nature, 1995, 376: 238-240

[52] Morrell D G. Catalysis of Organic Reactions. NY: Marcel Dekker, 2003. 577-586

[53] Reyes P, Aguirre M C, Melián-Cabrera I, Granados M L, Fierro J L G. J. Catal., 2002, 208: 229-237

[54] Reyes P, Aguirre M C, Pecchia G, Fierro J L G. J. Mol. Catal. A: Chem., 2000, 164: 245-251

[55] Gebauer-Henke E, Farbotko J, Touroude R, Rynkowski J. Kinet. Catal., 2008, 49: 574-580

[56] Ramos-Fernández E V, Silvestre-Albero J, Sepúlveda-Escribano A, Rodríguez-Reinoso F. Appl. Catal. A: Gen., 2010, 374: 221-227

[57] Ruiz-Martínez J, Fukui Y, Komatsu T, Sepúlveda-Escribano A. J. Catal., 2008, 260: 150-156

[58] Bachiller-Baeza B, Rodríguez-Ramos I, Guerrero-Ruiz A. Appl. Catal. A: Gen., 2001, 205: 227-237

[59] Yang X, Wang A, Wang X, Zhang T, Han K, Li J. J. Phys. Chem. C, 2009, 113: 20918-20926

[60] Tian L, Yang X, Jiang Z, Zhu Y, Pei Y, Qiao M, Fan K. Chem. Commun., 2011, 47: 6168-6170

[61] Iwasa N, Takizawa M, Arai M. Appl. Catal. A: Gen., 2005, 283: 255-263

[62] Rodrigues E L, Bueno J M C. Appl. Catal. A: Gen., 2002, 232: 147-158

[63] Rodrigues E L, Bueno J M C. Appl. Catal. A: Gen., 2004, 257: 201-211

[64] 裴燕(Pei Y), 方敬(Fang J), 胡华荣(Hu H R), 庄继华(Zhuang J H), 范康年(Fan K N), 李和兴(Li H X), 乔明华(Qiao M H). 化学学报(Acta Chimica Sinica), 2005, 63(4): 289-294

[65] Pei Y, Guo P, Qiao M, Li H, Wei S, He H, Fan K. J. Catal., 2007, 248: 303-310

[66] Pei Y, Hu H, Fang J, Qiao M, Dai W, Fan K, Li H. J. Mol. Catal. A: Chem., 2004, 211: 243-249

[67] Djerboua F, Benachour D, Touroude R. Appl. Catal. A: Gen., 2005, 282: 123-133

[68] Bailie J E, Hutchings G J, Abdullah H A, Anderson J A, Rochester C H. Phys. Chem. Chem. Phys., 2000, 2: 283-290

[69] Rodrigues E L, Marchi A J, Apesteguia C R, Bueno J M C. Appl. Catal. A: Gen., 2005, 294: 197-207

[70] Catillon-Mucherie S, Ammari F, Krafft J M, Lauron-Pernot H, Touroude R, Louis C. J. Phys. Chem. C, 2007, 111: 11619-11626

[71] Catillon-Mucherie S, Lauron-Pernot H, Louis C. J. Phys. Chem. C, 2010, 114: 11140-11147

[72] Reyes P, Pecchi G, Fierro J L G. Langmuir, 2001, 17: 522-527

[73] Dandekar A, Baker R T K, Vannice M A. J. Catal., 1999, 184: 421-439

[74] Coloma F, Marquez F, Rochester C H, Anderson J A. Phys. Chem. Chem. Phys., 2000, 2: 5320-5327

[75] 王月娟(Wang Y J), 王雪俐(Wang X L), 谢冠群(Xie G Q), 鲁继青(Lu J Q), 金炜阳(Jin W Y), 刘西敬(Liu X J), 罗孟飞(Luo M F). 催化学报 (Chinese Journal of Catalysis), 2008, 29 (5): 482-488

[76] Hutchings G J, King F, Okoye I P, Padley M B, Rochester C H. J. Catal., 1994, 148: 453-463

[77] Chiu M E, Watson D J, Kyriakou G, TikhovM S, Lambert R M. Angew. Chem. Int. Ed., 2006, 45: 7530-7534

[78] 刘自力(Liu Z L), 刘其海(Liu Q H). 工业催化(Industrial Catalysis), 2006, 14 (7): 38-41

[79] Abdullah H A, Rochester C H, Anderson J A, Bailie J E, Richardson N V, Hutchings G J. Phys. Chem. Chem. Phys., 2000, 2: 3925-3932

[80] Delbecq F, Sautet P. J. Catal., 1995, 152: 217-236

[81] Delbecq F, Sautet P. J. Catal., 2002, 211: 398-406

[82] Cao X M, Burch R, Hardacre C, Hu P. Catal. Today, 2011, 165: 71-79

[83] Laref S, Delbecq F, Loffreda D. J. Catal., 2009, 285: 35-42

[84] Urquhart A J, Williams F J, Vaughan O P H, Cropley R L, Lambert R M. Chem. Commun., 2005, 1977-1979

[85] Hirschl R, Delbecq F, Sautet P, Hafner J. J. Catal., 2003, 217: 354-366

[86] Jerdev D I, Olivas A, Koel1 B E. J. Catal., 2002, 205: 278-288

[87] Chiu M E, Kyriakou G, Williams F J, Watson D J, Tikhov M S, Lambert R M. Chem. Commun., 2006, 1283-1285

[88] Hammer B, Nrskov K. Nature, 1995, 376: 238-240

[89] Consonni M, Touroude R, Murzin D Y. Chem. Eng. Technol., 1998, 21: 605-609

[90] Englisch M, Ranade V S, Lercher J A. Appl. Catal. A: Gen., 1997, 163: 111-122

[91] Margitfalvi J L, Tompos A, Kolosova I, Valyon J. J. Catal., 1998, 174: 246-249

[92] Serrano-Ruiz J C, López-Cudero A, Solla-Gullón J, Sepúlveda-Escribano A, Aldaz A, Rodríguez-Reinoso F. J. Catal., 2008, 253: 159-166
[1] Bai Ying, Peng Jiajian, Li Jiayun, Lai Guoqiao, Li Xiaonian. Preparation Methods and Application of Heterogeneous Catalysts for Hydrosilylation [J]. Progress in Chemistry, 2011, 23(12): 2466-2477.
[2] Wang Haiming,Wang Zheng,Ding Kuiling. Recent Progress in Self-Supported Chiral Catalysts [J]. Progress in Chemistry, 2010, 22(07): 1471-1481.
[3] . Cross-Metathesis Reaction of Olefins over Heterogeneous Catalysts [J]. Progress in Chemistry, 2009, 21(04): 784-790.
[4] Li Xin|Zhang Weiping**|Li Xiujie|Liu Shenglin. Heterogeneous Catalysts for Olefin Cross-Metathesis [J]. Progress in Chemistry, 2008, 20(0708): 1021-1031.
[5] Luo Shuwen1,2|Chen Tong1**|Zeng Yi1|Wang Gongying1. Titanium-silicate mesoporous Molecular Sieves [J]. Progress in Chemistry, 2008, 20(0203): 212-220.
[6] Lu Fang,Liu Jing,Xu Jie*. Ruthenium Supported Catalysts in Selective Hydrogenation of Benzene to Cyclohexene [J]. Progress in Chemistry, 2003, 15(04): 338-.
[7] Li Xiaohong,Li Can**. Progress in Enantioselective Hydrogenation on Heterogeneous Catalysts [J]. Progress in Chemistry, 2003, 15(03): 204-.