中文
Earlier issues
Announcement
More
Progress in Chemistry 2008, Vol. 20 Issue (10): 1474-1486 Previous Articles   Next Articles

• Review •

Catalytical Selective Oxidation of Glycerol

Li Mingyan1 Zhou Chunhui1** Jorge N Beltramini2 Yu Weihua1 Fan Yongxian1   

  1. (1.College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310032, China; 2. ARC Centre of Excellence for Functional Nanomaterials, The Australian Institute for Bioengineering and Nanotechnology and School of Engineering, The University of Queensland, St. Lucia, QLD 4072, Australia)

  • Received: Revised: Online: Published:
  • Contact: Zhou Chunhui
PDF ( 3133 ) Cited
Export

EndNote

Ris

BibTeX

With the rapid development of biodiesel worldwide, the amount of glycerol, as by-product of biodiesel processes, is increasing so greatly that the effective utilization of glycerol becomes a challenging topic with great significance. Here the recent progress of research and development on the catalytic selective oxidation of glycerol, are specifically reviewed. The reaction networks of catalytic oxidation of glycerol, and related products and their potential applications are summarized. Especially, the catalysts and catalytic mechanism during the process of chemoselective catalytic oxidation of the glycerol are discussed The influence of different catalysts, supported noble or non-noble metal catalysts, porous oxides, and reaction conditions on selectivity, conversion during the oxidation processes of glycerol are summarized and remarked, together with the discussion of catalytic mechanism. The present situation of electrocatalytic selective oxidation of glycerol and novel oxidation-assisted polymerization of glycerol to Polyketomalonate and related catalytic mechanism are introduced. The recent progress of research and process development on production of dihydroxyacetone (DHA) by biocatalytic oxidation of glycerol is summarized. The pending problems and the prospects in the catalytic oxidation of glycerol are stated.
Key words: glycerol, catalytically selective oxidation, electrocatalytic oxidation, oxidation-assisted polymerization, biocatalytic oxidation, polyketomalonate, dihydroxyacetone

CLC Number: 

[ 1 ] 闵恩泽(Min E Z) . 绿色化学技术( Green Chemistry Technology) . 南昌: 江西科学技术出版社(Nanchang : Jiangxi Science &Technology Press) , 2001. 1 —28
[ 2 ] 闵恩泽(Min E Z) . 化工学报(Journal of Chemical Industry and Engineering) , 2006 , 57(8) : 1739 —1745
[ 3 ] 王庆昭(Wang Q Z) , 郑宗宝(Zheng Z B) , 刘子鹤(Liu Z H)等. 化学进展(Progress in Chemistry) , 2007 , 19(7P8) : 1198 —1205
[ 4 ] 匡廷云(Kuang T Y) , 张新时(Zhang X S) , 陈勇(Chen Y) 等.中国能源可持续发展若干重大问题研究(Major Problems for Sustainable Development of China Energy Resouces) . 严陆光, 陈俊武主编(eds. Yan L G, Chen J W) . 北京: 科学出版社(Beijing : Science Press) , 2007. 353 —376
[ 5 ] 匡廷云(Kuang T Y) , 白克智(Bai K Z) , 杨秀山(Yang X S) .化学进展(Progress in Chemistry) , 2007 , 19(7P8) : 1060 —1063
[ 6 ] 陈曦(Chen X) , 韩志群(Han Z Q) , 孔繁华(Kong F H) 等. 化学进展(Progress in Chemistry) , 2007 , 19(7P8) : 1091 —1097
[ 7 ] 伍丹(Wu D) , 施永聪(Shi Y C) , 龙正松(Long Z S) 等. 贵州化工(Guizhou Chemical Industry) , 2007 , 32(2) : 16 —19
[ 8 ] 何延青(He Y Q) , 吴永强(Wu Y Q) , 闻建平(Wen J P) . 中国油脂(China Oils and Fats) , 2007 , 32(5) : 47 —51
[ 9 ] Suppes G J , Dasari M A , Doskocil E J , et al . Appl . Catal , A:Gen. , 2004 , 257 (2) : 213 —223
[10] Yazdani S S , Gonzalezs R. Current Opinion in Biotechnol . ,2007 , 18(3) : 213 —219
[11] 刘宏娟(Liu H J ) , 杜伟(Du W) , 刘德华(Liu D H) . 化学进展(Progress in Chemistry) , 2007 , 19(7P8) : 1185 —1189
[12] 1996-09-01[2008-09-09 ] . http://www.biodiesel.org/resources/reportsdatabase/reports/gen/19960901-gen-235.pdf
[13] Tyson K S , Bozell J , Wallace R , Moens L. NREL/TP-510-34796 , 2004
[14] Zhou C H , Beltramini J N , Fan Y X. Lu G. Q. Chem. Soc.Rev. , 2008 , 37 : 527 —549
[15] 冯建(Feng J) , 袁茂林(Yuan ML) , 陈华(Chen H) , 李贤均(Li X Y) 等. 化学进展(Progress in Chemistry) , 2007 , 19 (5) :651 —658
[16] 2007-12-6 [ 2008-09-09 ] . http://www. chemyq.com/xz/xz5/43727icioq.htm
[17] 2008-08-28 [ 2008-09-09 ] . http://www. hxchem.net/hyselldetail.php?id = 448235&user=zhongyitai
[18] 2006-07-25 [ 2008-09-09 ] . http://www. gongkong.com/webpage/paper/200607/6-94F2-57071979BC27.htm
[19] Avelino C , Sara I , Alexandra V. Chem. Rev. , 2007 , 107 :2411 —2502
[20] Demirel-Gülen S , Lucas M, Claus P. Catal . Today , 2005 , 102 :166 —172
[21] Bemito G G, Ozores M, Pena M. Bioresour. Technol . , 1994 ,49 : 209 —212
[22] Bisping B , Hecker D , Rehm H J . Appl . Microbiol . Biotechnol . ,1989 , 32 : 119 —123
[23] Bisping B , Rehm H J . Appl . Microbiol . Biotechnol . , 1990 , 32 :380 —383
[24] 胡云良(Hu Y L) , 楼哲丰(Lou Z F) , 楼文文(Lou W W) 等.中国卫生检验杂志( Chinese Journal of Health Laboratory Technology) , 2003 , 13(4) : 425 —426
[25] Takehiro I , Hiroyuki H , Akira F , Yukinaga Y. JP 05 331 100 ,1993
[26] Teruyuki N , Yoshinori K. JP 1 168 292 , 1989
[27] 2008-05-16 [ 2008-09-09 ] . http://www.chem59.com/info/detail3206.html
[28] 2008-09-04 [ 2008-09-09 ] . http://en.wikipedia.org/wiki/Dihydroxyacetone
[29] 2008-02-01 [ 2008-09-09 ] . http://www.6chem.com/07.asp?id=1319
[30] 徐克勋(Xu K X) . 精细有机化工原料及中间体( The Fine Chemical and Intermediate) . 北京: 化学工业出版社(Beijing :Chemical Industry Press) , 2002
[31] 田克胜(Tian K S) , 王保伟(Wang B W) , 许根慧(Xu G H) .天然气化工(Chemical Engineering of Gas) , 2006 , 31 : 60 —71
[32] 王东方(Wang D F) . 化工技术经济( Chemical Techno Economics) , 2003 , 21(3) : 20 —22
[33] 赵光辉(Zhao G H) , 任敦泾(Ren D J ) , 李建忠(Li J Z) . 化工科技市场(Chemical Technology Market) , 2006 , 2 : 32 —35
[34] http://www.zbdongfang.com.cn/ArticleShow.asp?ArticleID=196
[35] Kimura H. App. Catal . A: Gen. , 1993 , 105 (2) : 147 —158
[36] Kimura H , Tsuto K. Appl . Catal . A: Gen. , 1993 , 96 ( 2) :217 —228
[37] Carrettin S , McMorn P , Johnston P , Hutchings GJ , et al . Phys.Chem. Chem. Phys. , 2003 , 5(6) : 1329 —1336
[38] Behr A , Botulinski A , Carduck F. EP4 107 986 , 1991
[39] Besson M, Gallezot P. Catal . Today 2000 , 57(1P2) : 127 —141
[40] Mallat T , Baiker A. Catal . Today , 1994 , 19(2) : 247 —283
[41] Prati L , Rossi M. J . Catal . , 1998 , 176 (2) : 552 —560
[42] Biella S , Castiglioni G L , Fumagalli C , Prati L , et al . Catal .Today , 2002 , 72(1/2) : 43 —49
[43] Carrettin S , McMorn P , Hutchings GJ . Chem. Commun. , 2002 ,696 —697
[44] Enache D I , Edwards J K, Landon P , Hutchings G J , et al .Science , 2006 , 311 (5759) : 362 —365
[45] Garcia R , Besson M, Gallezot P. Appl . Catal . A: Gen. , 1995 ,127(1/2) : 165 —176
[46] Fordham P , Besson M, Gallezot P. Catal . Lett . , 1997 , 46 (3/4) : 195 —199
[47] Demirel S , Lehnert K, Lucas M, Claus P. Appl . Catal . B :Environ. , 2007 , 70(1/4) : 637 —643
[48] Demirel-Gülen S , Clucase M, Claus P L. Catal . Today , 2005 ,102 : 166 —172
[49] Ketchie W C , Fang Y L , Wong M S , et al . J . Catal . , 2007 ,250 : 94 —101
[50] Ketchie W C , Murayama M, Davis R J . Topics in Catal . , 2007 ,44(1/2) : 307 —317
[51] Porta F , Prati L. J . Catal . , 2004 , 224 : 397 —403
[52] Dimitratos N , Porta F , Prati L. Appl . Catal . A: Gen. , 2005 ,291 : 210 —214
[53] Dimitratos N , Porta F , Prati L , et al . Catal . Lett . , 2005 , 99 (3/4) : 181 —185
[54] Carrettin S , McMorn P , Johnston P , et al . Topics Catal . , 2004 ,27 (1/4) : 131 —136
[55] Dimitratos N , Messi C , Prati L , et al . J . Mol . Catal . A:Chem. , 2006 , 256 , 21 —28
[56] Bianchi C L , Canton P , Prati L , et al . Catal . Today , 2005 ,102 , 203 —212
[57] McMorn P , Roberts G, Hutchings G J , et al . Catal . Lett . ,1999 , 63 (3/4) : 193 —197
[58] Zhou C H , Beltramini J N , Abeydeera P , Lu G Q. The Proceedings of the 14th International Congress on Catalysis , Seoul .2008
[59] Abbadi A , Bekkum H. Appl . Catal . A: Gen. , 1996 , 148 :113 —122
[60] Hutchings GJ , Carrettin S , Landon P , et al . Topics in Catal . ,2006 , 38(4) : 223 —230
[61] Kluytmans J H J , Markusse A P , Kuster B F M, et al . Catal .Today , 2000 , 57(1/2) , 143 —155
[62] Dimitratos N , Lopez Sanchez J A , Prati L , et al . Catal . Lett . ,2006 , 108 (3/4) : 147 —153
[63] Biella S , Porta F , Prati L , et al . Catal . Lett . , 2003 , 85 (1/2) :91 —96
[64] Bond G C , Thompson D. Cat . Rev. Sci . Eng. , 1999 , 41 (3/4) : 319 —388
[65] Gallezot P. Catal . Today , 1997 , 37(4) : 405 —418
[66] Abad A , Almela C , Corma A , Garcia H. Tetrahedron , 2006 , 62(28) : 6666 —6672
[67] Mallat T , Baiker A. Catal . Today , 1995 , 24(1/2) : 143 —150
[68] Smits P C C , Kuster B F M, van der Wiele K, et al . Appl .Catal . , 1987 , 33 (1) : 83 —96
[69] Abbadi A , van Bekkum H. Appl . Catal . A: Gen. , 1995 , 124(2) : 409 —417
[70] Fordham P , Besson M, Gallezot P. Catal . Lett . , 1997 , 46 (3/4) : 195 —199
[71] Mallat T , Bodnar Z , Hug P , Baiker A. J . Catal , 1995 , 153 :131 —143
[72] Fordham P. Besson M. Gallezot P. Appl . Catal . A: Gen. ,1995 , 133 (2) : 179 —184
[73] Davis R J , Ketchie W C. Abstracts of Papers , 234th ACS National Meeting , Boston , MA. , 2007
[74] Ketchie W C , Murayama M, Davis R J . J . Catal . , 2007 , 250(2) : 264 —273
[75] Shaffer P A , Friedemann T E. J . Biol . Chem. 1930 , 86 : 345 —374
[76] Wang D , Villa A , Prati L , et al . Chem. Commun. , 2006 ,1956 —1958
[77] Dimitratos N , Villa A , Prati L , et al . J . Catal . , 2006 , 244 :113 —121
[78] Axel G. Topics in Catal . , 2006 , 37(1) : 29 —39
[79] Yildiz , G, Kadirgan F. Annali di Chimica (Rome) , 1994 , 84(9/10) : 455 —466
[80] Yildiz G, Kadirgan F. Kim. Kim. Muhendisligi Semp. , 8th (ed.Aydin A) . 1992 , 1 , 187 —189
[81] Yildiz , G, Kadirgan F. J . Electrochem. Soc. , 1994 , 141 (3) :725 —730
[82] Roquet L , Belgsir E M, Leger J M, Lamy C. Electrochimica Acta , 1994 , 39(16) : 2387 —2394
[83] Kyriacou D , Tougas T P. J . Org. Chem. , 1987 , 52 ( 11) :2318 —2319
[84] Venancio E C , Napporn W T , Motheo A J . Electrochim. Acta ,2002 , 47(9) : 1495 —1501
[85] Ciriminna R , Palmisano G, Pina C D , Pagliaro M R M.Tetrahedron Lett . , 2006 , 47(39) : 6993 —6995
[86] De Nooy A E J , Besemer A C , van Bekkum H. Synthesis -Stuttgart , 1996 , 10 : 1153 —1174
[87] Ciriminna R , Pagliaro M. Adv. Synth. Catal . , 2003 , 345 (3) :383 —388
[88] Kimura H. J . Polym. Sci . A: Polym. Chem. , 1996 , 34 (17) :3595 —3605
[89] Kimura. H. J . Polym. Sci , A: Polym. Chem. , 1996 , 34 :3607 —3614
[90] Kimura H. J . Polym. Sci . A: Polym. Chem. , 1996 , 34 :3615 —3620
[91] Kimura H. J . Polym. Sci . A: Polym. Chem. , 1998 , 36 : 195 —205
[92] Kimura. H. Polym. Adv. Technol . , 2001 , 12 (11P12) : 697 —710
[93] Kimura H. J . Polym. Sci . A: Polym. Chem. , 1998 , 36 :2993 —2994
[94] Kimura H. JP 151 346 , 1996
[95] Salusjaervi T , Povelainen M, Hvorslev N , et al . Appl . Microb.Biotechnol . , 2004 , 65 : 306 —314
[96] Hekmat D , Bauer R , Fricke J . Bioprocess Biosyst . Eng. , 2003 ,26 : 109 —116
[97] Ruediger B , Dariusch H. Biotechnol . Progress , 2006 , 22 (1) :278 —284
[98] Matsushita K, Toyoma H , Adachi O. Adv. Microb. Physio. ,1994 , 136 : 247 —301
[99] Prust C , Hoffmeister M, Liesegang H , et al . Nat . Biotechnol . ,2005 , 23(2) : 195 —200
[100] Ameyama M, Shinagawa E , Matsushita K, Adachi O. Agric.Biol . Chem. , 1985 , 49 : 1001 —1010
[101] Claret C , Salmon J M, Romieu C , Bories A. Appl . Microb.Biotechnol . , 1994 , 41 : 359 —365
[102] Bories A , Claret C , Soucaille P. Process Biochem. , 1991 , 26 ,(4) : 243 —248
[103] Claret C , Bories A , Soucaille P. Current Microb. , 1992 , 25 (3) :149 —155
[104] Bories A , Claret C , Soucaille P. Journal of Industrial Microbiology , 1993 , 11 (2) : 105 —112.
[105] Ohrem H L , Voss H. Biotechnol . Lett . , 1995 , 17 (9) : 981 —984
[106] Wethmar M, Deckwer W D. Biotechnol . Tech. , 1999 , 13 (4) :283 —287
[107] Svitel J , Sturdik E J . Ferment . Technol . , 1994 , 78 (5) : 351 —355
[108] Tkac J , Navratil M, Sturdik E , Gemeiner P. Enzyme Microb.Technol . , 2001 , 28(4/5) : 383 —388
[109] Bauer R. , Katsikis N , Varga S , Hekmat D. Bioprocess Biosyst Eng. , 2005 , 28(1) : 37 —43
[110] Wei S , Song Q , Wei D. Prep. Biochem. Biotechnol . , 2007 , 37(1) : 67 —76
[111] G? etgens C , Degner U , Bringer-Meyer S. Appl . Microb.Biotechnol . , 2007 , 76(3) : 553 —559
[112] Mostafa N A , Magdy Y H. Energy Convers Mgmt . , 1998 , 39(7) : 671 —677
[113] Hekmat D , Bauer R , Neff V. Process Biochem. , 2007 , 42 (1) :71 —76
[114] Dimitratos N , Villa A , Bianchi C L , Prati L , Makkee M. Appl .Catal . A: Gen. , 2006 , 311 : 185 —192
[115] Meurig T J , Raja R. Catal . Today , 2006 , 117 (1/3) : 22 —31
[116] Schamann M, Schafer H J . Euopean J , Org. Chem. , 2003 , 2 :351 —358
[1] Sun Jia, Wang Pu, Zhang Pengpeng, Huang Jin. Application of Glycerol in Microbial Biosynthesis and Biocatalysis [J]. Progress in Chemistry, 2016, 28(9): 1426-1434.
[2] Hua Donglong, Zhuang Xiaoyu, Tong Dongshen, Yu Weihua, Zhou Chunhui. Catalytic Oxidehydration of Glycerol to Acrylic Acid [J]. Progress in Chemistry, 2016, 28(2/3): 375-390.
[3] Ren Fangfang, Jiang Fengxing, Zhou Weiqiang, Du Yukou, Xu Jingkun. Application of Conducting Polymers/Metal Composites for C1 Molecules Electrooxidation [J]. Progress in Chemistry, 2012, (9): 1818-1836.
[4] Feng Guodong, Cheng Lihua, Xu Xinhua, Zhang Lin, Chen Huanlin. Strategies in Genetic Engineering of Microalgae for High-Lipid Production [J]. Progress in Chemistry, 2012, 24(07): 1413-1426.
[5] . Advances on Technology of Microalgal High-lipid Production [J]. Progress in Chemistry, 2010, 22(06): 1221-1232.
[6] Feng Jian,Yuan Maolin,Chen Hua*,Li Xianjun. Studies and Applications of Catalytic Hydrogenolysis of Glycerol [J]. Progress in Chemistry, 2007, 19(05): 651-658.