Recent Advances in Selective Oxidation of Glycerol to Lactic Acid over Noble Metal Catalysts

Haodong Xie; Zunlong Hu; Haobin Wei; Sida Ge; Zixuan Wang; Yuming Zhang; Zhijie Wu

doi:10.7536/PC231114

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Prog Chem ›› 2024, Vol. 36 ›› Issue (7) : 1088-1101. DOI: 10.7536/PC231114

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Recent Advances in Selective Oxidation of Glycerol to Lactic Acid over Noble Metal Catalysts

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Abstract

the problem of excess glycerol as a by-product of biodiesel production has become more and more prominent,and the catalytic conversion of glycerol to high-value-added chemicals is of great significance.in recent years,noble metal catalysts(Au,Pt,Pd,etc.)are often used to catalyze the conversion of glycerol to lactic acid,in which the improvement of lactic acid selectivity and catalyst stability are the key challenges for the catalysts.Here,we summarized the reaction mechanism of selective oxidation of glycerol to lactic acid over supported noble metal catalysts,revealing the role of different metal active sites.At the same time,the effects of metal particle size,support,and pH of the reaction system on the reaction performance are discussed based on the structure and electronic properties of noble metal active sites.Also,the role of metal in the promotion and support of strong interaction on the activation of the hydroxyl groups of glycerol was clarified.Finally,the main challenges and prospects for the selective oxidation of glycerol to lactic acid were clarified。

Contents

1 Introduction

2 Reaction mechanism of glycerol to lactic acid

2.1 Hydrothermal conversion of glycerol to lactic acid

2.2 Selective oxidation of glycerol to lactic acid

2.3 Electrocatalytic oxidation of glycerol to lactic acid

3 Noble metal catalyst

3.1 Au-based catalyst

3.2 Pt-based catalyst

3.3 Other noble metal catalyst

4 Catalyst supports and roles

4.1 Carbon materials

4.2 Zeolite

4.3 Metallic oxide

4.4 Other supports

5 Catalyst deactivation and reusability

6 Conclusion and outlook

Key words

glycerol / lactic acid / selective oxidation / noble metal / catalysts

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Haodong Xie , Zunlong Hu , Haobin Wei , et al . Recent Advances in Selective Oxidation of Glycerol to Lactic Acid over Noble Metal Catalysts[J]. Progress in Chemistry. 2024, 36(7): 1088-1101 https://doi.org/10.7536/PC231114

References

List( Publishing order | Descend order by publishing year | Descend order by cited within ) Chart analysis

[1]	Arcanjo M R A, da Silva I J Jr, Cavalcante C L Jr, Iglesias J, Morales G, Paniagua M, Melero J A, Vieira R S. Biofuels Bioprod. Biorefin., 2020, 14(2): 357. Cited in this article [2]

[2]	Liu Y J, Zhong B Q, Lawal A. RSC Adv., 2022, 12(43): 27997. Cited in this article [1]

[3]	Koranian P, Huang Q, Dalai A K, Sammynaiken R. Catalysts, 2022, 12(8): 897. Cited in this article [1]

[4]	Tang C, Li S M, Yu S S. Chinese J. Mol. Catal., 2022, 36(4): 398. (唐成, 李双明, 于三三. 分子催化, 2022, 36(4): 398.) Cited in this article [1]

[5]	Dodekatos G, Schünemann S, Tüysüz H. ACS Catal., 2018, 8(7): 6301. Cited in this article [1]

[6]	Ghaffar T, Irshad M, Anwar Z, Aqil T, Zulifqar Z, Tariq A, Kamran M, Ehsan N, Mehmood S. J. Radiat. Res. Appl. Sci., 2014, 7(2): 222. Cited in this article [1]

[7]	Wang K, Yang Z Y, Ma Y Y, Zhao W, Sun J Y, Lu T L, He H. Biofuels Bioprod. Biorefin., 2022, 16(5): 1428. Cited in this article [2]

[8]	Dusselier M, Van Wouwe P, Dewaele A, Makshina E, Sels B F. Energy Environ. Sci., 2013, 6(5): 1415. Cited in this article [1]

[9]	Zavrazhnov S A, Esipovich A L, Danov S M, Zlobin S Y, Belousov A S. Kinet. Catal., 2018, 59(4): 459. Cited in this article [1]

[10]	Zhou C H C, Beltramini J N, Fan Y X, Max Lu G Q. Chem. Soc. Rev., 2008, 37(3): 527. Cited in this article [2]

[11]	Demirel-Gülen S, Lucas M, Claus P. Catal. Today, 2005, 102: 166. Cited in this article [2]

[12]	Gupta G, Roling L T. ChemCatChem, 2023, 15(2): e202201188. Cited in this article [1]

[13]	Yang L H, Li X W, Chen P, Hou Z Y. Chin. J. Catal.-Eur. J., 2019, 40(7): 1020. Cited in this article [1]

[14]	Akbulut D, Özkar S. RSC Adv., 2022, 12(29): 18864. Cited in this article [1]

[15]	Shen Y H, Zhang S H, Li H J, Ren Y, Liu H C. Chem. - Eur. J., 2010, 16(25): 7368. Cited in this article [5]

[16]	Lu T L, Fu X M, Zhou L P, Su Y L, Yang X M, Han L, Wang J F, Song C Y. ACS Catal., 2017, 7(10): 7274. Cited in this article [4]

[17]	Kishida H, Jin F M, Zhou Z Y, Moriya T, Enomoto H. Chem. Lett., 2005, 34(11): 1560. Cited in this article [3]

[18]	Shen Z, Jin F M, Zhang Y L, Wu B, Kishita A, Tohji K, Kishida H. Ind. Eng. Chem. Res., 2009, 48(19): 8920. Cited in this article [2]

[19]	Sharninghausen L S, Campos J, Manas M G, Crabtree R H. Nat. Commun., 2014, 5: 5084. Cited in this article [2]

[20]	Xu S G, Tian Q, Xiao Y, Zhang W Y, Liao S Q, Li J M, Hu C W. J. Catal., 2022, 413: 407. Cited in this article [1]

[21]	Chen L, Ren S J, Ye X P. Fuel Process. Technol., 2014, 120: 40. Cited in this article [3]

[22]	Tang Z C, Liu P, Cao H T, Bals S, Heeres H J, Pescarmona P P. ACS Catal., 2019, 9(11): 9953. Cited in this article [1]

[23]	Lakshmanan P, Upare P P, Le N T, Hwang Y K, Hwang D W, Lee U H, Kim H R, Chang J S. Appl. Catal. A Gen., 2013, 468: 260. Cited in this article [3]

[24]	Xu J L, Zhang H Y, Zhao Y F, Yu B, Chen S, Li Y B, Hao L D, Liu Z M. Green Chem., 2013, 15(6): 1520. Cited in this article [4]

[25]	Cho H J, Chang C C, Fan W. Green Chem., 2014, 16(7): 3428. Cited in this article [4]

[26]	Tao M L, Zhang D, Deng X, Li X Y, Shi J Y, Wang X H. Chem. Commun., 2016, 52(16): 3332. Cited in this article [1]

[27]	Feng S X, Takahashi K, Miura H, Shishido T. Fuel Process. Technol., 2020, 197: 106202. Cited in this article [2]

[28]	Komanoya T, Suzuki A, Nakajima K, Kitano M, Kamata K, Hara M. ChemCatChem, 2016, 8(6): 1094. Cited in this article [2]

[29]	Kano E, Aihara T, Ghampson I T, Nogami T, Miura H, Shishido T. ACS Sustainable Chem. Eng., 2022, 10(37): 12072. Cited in this article [1]

[30]	Pazhavelikkakath Purushothaman R K, Van Haveren J, Melián- Cabrera I, van Eck E R H, Heeres H J. ChemSusChem, 2014, 7(4): 1140. Cited in this article [3]

[31]	Purushothaman R K P, van Haveren J, van Es D S, Melián-Cabrera I, Meeldijk J D, Heeres H J. Appl. Catal. B Environ., 2014, 147: 92. Cited in this article [4]

[32]	Pescarmona P P, Janssen K P F, Delaet C, Stroobants C, Houthoofd K, Philippaerts A, De Jonghe C, Paul J S, Jacobs P A, Sels B F. Green Chem., 2010, 12(6): 1083. Cited in this article [1]

[33]	Li L, Collard X, Bertrand A, Sels B F, Pescarmona P P, Aprile C. J. Catal., 2014, 314: 56. Cited in this article [1]

[34]	Lux S, Stehring P, Siebenhofer M. Sep. Sci. Technol., 2010, 4512-13: 1921. Cited in this article [1]

[35]	Dai C C, Sun L B, Liao H B, Khezri B, Webster R D, Fisher A C, Xu Z J. J. Catal., 2017, 356: 14. Cited in this article [3]

[36]	Yan Y F, Wang Q Y, Hao P J, Zhou H, Kong X G, Li Z H, Shao M F. ACS Appl. Mater. Interfaces, 2023, 15(19): 23265. Cited in this article [1]

[37]	He Z Y, Ning X M, Yang G X, Wang H J, Cao Y H, Peng F, Yu H. Catal. Today, 2021, 365: 162. Cited in this article [2]

[38]	Yang H L, Li G G, Jiang G X, Zhang Z S, Hao Z P. Appl. Catal. B Environ., 2023, 325: 122384. Cited in this article [1]

[39]	Villa A, Dimitratos N, Chan-Thaw C E, Hammond C, Prati L, Hutchings G J. Acc. Chem. Res., 2015, 48(5): 1403. Cited in this article [2]

[40]	Davis S E, Ide M S, Davis R J. Green Chem., 2013, 15(1): 17. Cited in this article [2]

[41]	Della Pina C, Falletta E, Rossi M. Chem. Soc. Rev., 2012, 41(1): 350. Cited in this article [1]

[42]	Hashmi A S K. Chem. Rev., 2007, 107(7): 3180. Cited in this article [1]

[43]	Meng Y, Zou S H, Zhou Y H, Yi W Z, Yan Y, Ye B, Xiao L P, Liu J J, Kobayashi H, Fan J. Catal. Sci. Technol., 2018, 8(14): 3704. Cited in this article [1]

[44]	Biella S, Prati L, Rossi M. J. Catal., 2002, 206(2): 242. Cited in this article [1]

[45]	Bianchi C, Porta F, Prati L, Rossi M. Top. Catal., 2000, 13(3): 231. Cited in this article [2]

[46]	Ketchie W C, Murayama M, Davis R J. J. Catal., 2007, 250(2): 264. Cited in this article [1]

[47]	Redina E A, Kirichenko O A, Greish A A, Kucherov A V, Tkachenko O P, Kapustin G I, Mishin I V, Kustov L M. Catal. Today, 2015, 246: 216. Cited in this article [1]

[48]	Zope B N, Hibbitts D D, Neurock M, Davis R J. Science, 2010, 330(6000): 74. Cited in this article [1]

[49]	Purushothaman R K P, van Haveren J, Mayoral A, Melián-Cabrera I, Heeres H J. Top. Catal., 2014, 57(17): 1445. Cited in this article [1]

[50]	Shen Y H, Li Y M, Liu H C. J. Energy Chem., 2015, 24(5): 669. Cited in this article [1]

[51]	Tang Z C, Fiorilli S L, Heeres H J, Pescarmona P P. ACS Sustainable Chem. Eng., 2018, 6(8): 10923. Cited in this article [2]

[52]	Tang Z C, Boer D G, Syariati A, Enache M, Rudolf P, Heeres H J, Pescarmona P P. Green Chem., 2019, 21(15): 4115. Cited in this article [3]

[53]	Zhou L P, Xu Y Y, Yang X M, Lu T L, Han L. Energy Convers. Manag., 2019, 196: 277. Cited in this article [1]

[54]	Bruno A M, Chagas C A, Souza M M V M, Manfro R L. Renew. Energy, 2018, 118: 160. Cited in this article [2]

[55]	Ftouni J, Villandier N, Auneau F, Besson M, Djakovitch L, Pinel C. Catal. Today, 2015, 257: 267. Cited in this article [1]

[56]	Checa M, Auneau F, Hidalgo-Carrillo J, Marinas A, Marinas J M, Pinel C, Urbano F J. Catal. Today, 2012, 196(1): 91. Cited in this article [1]

[57]	Wu G D, Liu Y N, He Y F, Feng J T, Li D Q. Appl. Catal. B Environ., 2021, 291: 120061. Cited in this article [3]

[58]	Zhang C, Wang T, Ding Y J. Catal. Lett., 2017, 147(5): 1197. Cited in this article [2]

[59]	Oberhauser W, Evangelisti C, Tiozzo C, Vizza F, Psaro R. ACS Catal., 2016, 6(3): 1671. Cited in this article [1]

[60]	An Z, Zhang Z L, Huang Z Y, Han H B, Song B B, Zhang J, Ping Q, Zhu Y R, Song H Y, Wang B, Zheng L R, He J. Nat. Commun., 2022, 13: 5467. Cited in this article [1]

[61]	Li Y, Zaera F. J. Catal., 2015, 326: 116. Cited in this article [1]

[62]	Lei J Q, Dong H, Duan X Z, Chen W Y, Qian G, Chen D, Zhou X G. Ind. Eng. Chem. Res., 2016, 55(2): 420. Cited in this article [2]

[63]	Sun Y Y, Li X W, Wang J G, Ning W S, Fu J, Lu X Y, Hou Z Y. Appl. Catal. B Environ., 2017, 218: 538. Cited in this article [2]

[64]	Zhang C, Wang T, Liu X, Ding Y J. J. Mol. Catal. A Chem., 2016, 424: 91. Cited in this article [1]

[65]	Zhang G Y, Jin X, Guan Y N, Yin B, Chen X B, Liu Y B, Feng X, Shan H H, Yang C H. Ind. Eng. Chem. Res., 2019, 58(31): 14548. Cited in this article [2]

[66]	Li Y B, Chen S, Xu J L, Zhang H Y, Zhao Y F, Wang Y B, Liu Z M. CLEAN, 2014, 42(8): 1140. Cited in this article [2]

[67]	Rinaudo M G, Beltrán A M, Fernández A, Cadús L E, Morales M R. Results Eng., 2022, 16: 100737. Cited in this article [1]

[68]	Marques F L, Oliveira A C, Mendes Filho J, Rodríguez-Castellón E, Cavalcante C L, Vieira R S. Fuel Process. Technol., 2015, 138: 228. Cited in this article [1]

[69]	Arcanjo M R A, Silva I J, Rodríguez-Castellón E, Infantes-Molina A, Vieira R S. Catal. Today, 2017, 279: 317. Cited in this article [1]

[70]	Shen L Q, Yu Z Y, Zhang D, Yin H B, Wang C T, Wang A L. J. Chem. Technol. Biotechnol., 2019, 94(1): 204. Cited in this article [1]

[71]	Ten S A, Kurmanova M D, Kurmanbayeva K, Torbina V V, Stonkus O A, Vodyankina O V. Appl. Catal. A Gen., 2024, 674: 119603. Cited in this article [1]

[72]	Li Y, Nielsen M, Li B, Dixneuf P H, Junge H, Beller M. Green Chem., 2015, 17(1): 193. Cited in this article [1]

[73]	Wang S, Yin K H, Zhang Y C, Liu H C. ACS Catal., 2013, 3(9): 2112. Cited in this article [1]

[74]	Jiang Z W, Zhang Z R, Wu T B, Zhang P, Song J L, Xie C, Han B X. Chem., 2017, 12(13): 1598. Cited in this article [1]

[75]	Pemmana H R, Barnwal P K, Uppaluri R V, Peela N R. J. Ind. Eng. Chem., 2023, 124: 224. Cited in this article [1]

[76]	Lari G M, García-Muelas R, Mondelli C, López N, Pérez-Ramírez J. Green Chem., 2016, 18(17): 4682. Cited in this article [1]

[77]	Tao M L, Zhang D, Guan H Y, Huang G H, Wang X H. Sci. Rep., 2016, 6: 29840. Cited in this article [1]

[78]	Gong Y T, Xie L, Chen C H, Liu J R, Antonietti M, Wang Y. Prog. Mater. Sci., 2023, 132: 101048. Cited in this article [1]

[79]	Zhang M Y, Liang D, Nie R F, Lu X Y, Chen P, Hou Z Y. Chin. J. Catal., 2012, 33(7-8): 1340. Cited in this article [1]

[80]	Schiros T, Nordlund D, Pálová L, Prezzi D, Zhao L Y, Kim K S, Wurstbauer U, Gutiérrez C, Delongchamp D, Jaye C, Fischer D, Ogasawara H, Pettersson L G M, Reichman D R, Kim P, Hybertsen M S, Pasupathy A N. Nano Lett., 2012, 12(8): 4025. Cited in this article [1]

[81]	Chen S S, Qi P Y, Chen J, Yuan Y Z. RSC Adv., 2015, 5(40): 31566. Cited in this article [2]

[82]	Zhang M Y, Shi J J, Sun Y Y, Ning W S, Hou Z Y. Catal. Commun., 2015, 70: 72. Cited in this article [2]

[83]	Sun Q M, Wang N, Yu J H. Adv. Mater., 2021, 33(51): 2104442. Cited in this article [1]

[84]	Suib S L, Přech J, Szaniawska E, Čejka J. Chem. Rev., 2023, 123(3): 877. Cited in this article [1]

[85]	Xia Y Q, Wu K Y, Liu C, Zhao X J, Wang J, Cao J X, Chen Z X, Fang M C, Yu J, Zhu C, Zhang X H, Wang Z L. Adv. Sci., 2024, 11(10): 2306533. Cited in this article [1]

[86]	Asgar Pour Z, Boer D G, Fang S, Tang Z C, Pescarmona P P. Catalysts, 2021, 11(11): 1346. Cited in this article [1]

[87]	Tang B, Wang D, Li A, Tang H M, Yang E C, Dai W L. Microporous Mesoporous Mater., 2023, 347: 112348. Cited in this article [3]

[88]	Cho H J, Dornath P, Fan W. ACS Catal., 2014, 4(6): 2029. Cited in this article [1]

[89]	Douthwaite M, Powell N, Taylor A, Ford G, López J M, Solsona B, Yang N T, Sanahuja-Parejo O, He Q, Morgan D J, Garcia T, Taylor S H. ChemCatChem, 2020, 12(11): 3097. Cited in this article [1]

[90]	Ide M S, Davis R J. Acc. Chem. Res., 2014, 47(3): 825. Cited in this article [1]

[91]	Pan Y N, Wu G D, He Y F, Feng J T, Li D Q. J. Catal., 2019, 369: 222. Cited in this article [3]

[92]	Evans C D, Kondrat S A, Smith P J, Manning T D, Miedziak P J, Brett G L, Armstrong R D, Bartley J K, Taylor S H, Rosseinsky M J, Hutchings G J. Faraday Discuss., 2016, 188: 427. Cited in this article [1]

[93]	An Z, Ma H H, Han H B, Huang Z Y, Jiang Y T, Wang W L, Zhu Y R, Song H Y, Shu X, Xiang X, He J. ACS Catal., 2020, 10(21): 12437. Cited in this article [1]

[94]	Wang C Y, Zhang X Q, Li J F, Qi X Y, Guo Z Y, Wei H, Chu H B. ACS Appl. Mater. Interfaces, 2021, 13(1): 522. Cited in this article [2]

[95]	Gándara F, Perles J, Snejko N, Iglesias M, Gómez-Lor B, Gutiérrez-Puebla E, Monge M Á. Angew. Chem. Int. Ed., 2006, 45(47): 7998. Cited in this article [1]