A switchable route to valuable commodity chemicals from glycerol via electrocatalytic oxidation with an earth abundant metal oxidation catalyst

Green Chemistry

Volumn 19, Issue 8, 2017, Pages 1958-1968

  Lam, Chun Ho ^a   Bloomfield, Aaron J ^b   Anastas, Paul T ^a,b  

^a Yale University   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85020198937     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c7gc00371d     Document Type: Article

References (68)

1. T. Werpy, G. Petersen, A. Aden, J. Bozell, J. Holladay, J. White, A. Manheim, D. Eliot, L. Lasure and S. Jones, Top Value Added Chemicals From Biomass. Volume 1 - Results of Screening for Potential Candidates From Sugars and Synthesis Gas, Department of Energy, Washington, DC, 2004
2. F. L. Marques A. C. Oliveira J. Mendes Filho E. Rodríguez-Castellón C. L. Cavalcante Jr. R. S. Vieira Fuel Process. Technol. 2015 138 228 235
3. R. K. P. Purushothaman J. van Haveren D. S. van Es I. Melián-Cabrera J. D. Meeldijk H. J. Heeres Appl. Catal., B 2014 147 92 100
4. J. Xu H. Zhang Y. Zhao B. Yu S. Chen Y. Li L. Hao Z. Liu Green Chem. 2013 15 1520 1525
5. T. Komanoya A. Suzuki K. Nakajima M. Kitano K. Kamata M. Hara ChemCatChem 2016 8 1094 1099
6. R. K. Pazhavelikkakath Purushothaman J. van Haveren I. Melián-Cabrera E. R. H. van Eck H. J. Heeres ChemSusChem 2014 7 1140 1147
7. C. H. Zhou J. N. Beltramini C. X. Lin Z. P. Xu G. Q. Lu A. Tanksale Catal. Sci. Technol. 2011 1 111 122
8. W. Hu D. Knight B. Lowry A. Varma Ind. Eng. Chem. Res. 2010 49 10876 10882
9. L. Xu Z. Han Q. Yao J. Deng Y. Zhang Y. Fu Q. Guo Green Chem. 2015 17 2426 2435
10. Y. Zhang X. Yan B. Niu J. Zhao Green Chem. 2016 18 3139 3151
11. N. D. Kim J. R. Park D. S. Park B. K. Kwak J. Yi Green Chem. 2012 14 2638 2646
12. C. Pendem P. Gupta N. Chaudhary S. Singh J. Kumar T. Sasaki A. Datta R. Bal Green Chem. 2012 14 3107 3113
13. J. Zhou J. Zhang X. Guo J. Mao S. Zhang Green Chem. 2012 14 156 163
14. F. Cai G. Xiao Catal. Sci. Technol. 2016 6 5656
15. C.-H. Zhou J. N. Beltramini Y.-X. Fan G. Q. Lu Chem. Soc. Rev. 2008 37 527 549
16. J. ten Dam U. Hanefeld ChemSusChem 2011 4 1017 1034
17. B. Katryniok H. Kimura E. Skrzynska J.-S. Girardon P. Fongarland M. Capron R. Ducoulombier N. Mimura S. Paul F. Dumeignil Green Chem. 2011 13 1960 1979
18. Y. Nakagawa K. Tomishige Catal. Sci. Technol. 2011 1 179 190
19. J. D. Beltramini and C.-H. Zhou, Catalytic Conversion of Glycerol to Valuable Commodity Chemicals, in Thermochemical Conversion of Biomass to Liquid Fuels and Chemicals, ed., M. Crocker, RSC Energy and Environment Series, London, 2011, ch. 17, pp. 435-467
20. L. Chen S. Ren X. P. Ye Fuel Process. Technol. 2014 120 40 47
21. D. Roy B. Subramaniam R. V. Chaudhari ACS Catal. 2011 1 548 551
22. G.-Y. Yang Y.-H. Ke H.-F. Ren C.-L. Liu R.-Z. Yang W.-S. Dong Chem. Eng. J. 2016 283 759 767
23. M. Dusselier P. Van Wouwe A. Dewaele E. Makshina B. F. Sels Energy Environ. Sci. 2013 6 1415 1442
24. P. Mäki-Arvela I. L. Simakova T. Salmi D. Y. Murzin Chem. Rev. 2014 114 1909 1971
25. R. Datta M. Henry J. Chem. Technol. Biotechnol. 2006 81 1119 1129
26. L. S. Sharninghausen J. Campos M. G. Manas R. H. Crabtree Nat. Commun. 2014 5 5084
27. Z. Lu I. Demianets R. Hamze N. J. Terrile T. J. Williams ACS Catal. 2016 6 2014 2017
28. Y. Li M. Nielsen B. Li P. H. Dixneuf H. Junge M. Beller Green Chem. 2015 17 193 198
29. L. S. Sharninghausen B. Q. Mercado R. H. Crabtree N. Hazari Chem. Commun. 2015 51 16201 16204
30. H. Habe T. Fukuoka D. Kitamoto K. Sakaki Appl. Microbiol. Biotechnol. 2009 84 445 452
31. M. Pagliaro, M. Rossi and R. S. o. Chemistry, The Future of Glycerol: New Uses of a Versatile Raw Material, Royal Society of Chemistry, 2008
32. H. Zhang X. Lin S. Chin M. W. Grinstaff J. Am. Chem. Soc. 2015 137 12660 12666
33. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, 1998
34. P. T. Anastas T. C. Williamson D. Hjeresen J. J. Breen Environ. Sci. Technol. 1999 33 116A 119A
35. P. T. Anastas, L. G. Heine and T. C. Williamson, in Green Chemical Syntheses and Processes, American Chemical Society, 2000, ch. 1, vol. 767, pp. 1-16
36. H. L. Chum and M. M. Baizer, The electrochemistry of biomass and derived materials, American Chemical Society, 1985
37. Z. Li M. Garedew C. H. Lam J. E. Jackson D. J. Miller C. M. Saffron Green Chem. 2012 14 2540 2549
38. Z. Li S. Kelkar L. Raycraft M. Garedew J. E. Jackson D. J. Miller C. M. Saffron Green Chem. 2014 16 844 852
39. S. K. Green J. Lee H. J. Kim G. A. Tompsett W. B. Kim G. W. Huber Green Chem. 2013 15 1869 1879
40. J. J. Roylance K.-S. Choi Green Chem. 2016 18 2956 2960
41. Y. Qiu L. Xin D. J. Chadderdon J. Qi C. Liang W. Li Green Chem. 2014 16 1305 1315
42. J. J. Roylance T. W. Kim K.-S. Choi ACS Catal. 2016 6 1840 1847
43. K. J. Carroll T. Burger L. Langenegger S. Chavez S. T. Hunt Y. Román-Leshkov F. R. Brushett ChemSusChem 2016 9 1904
44. S. Lee H. J. Kim E. J. Lim Y. Kim Y. Noh G. W. Huber W. B. Kim Green Chem. 2016 18 2877 2887
45. G. Yildiz F. Kadirgan J. Electrochem. Soc. 1994 141 725 730
46. Y. Kwon Y. Birdja I. Spanos P. Rodriguez M. T. M. Koper ACS Catal. 2012 2 759 764
47. S. Lux P. Stehring M. Siebenhofer Sep. Sci. Technol. 2010 45 1921 1927
48. All reactions are performed in alkaline and neutral media, and thus all products are expected to be present in a deprotonated form such as lactate and glycerate. However, the nomenclature of their neutral forms such as lactic acid and glyceric acid will be used interchangeably for the sake of discussion
49. A. J. Bloomfield S. W. Sheehan S. L. Collom R. H. Crabtree P. T. Anastas New J. Chem. 2014 38 1540 1545
50. A. J. Bloomfield S. W. Sheehan S. L. Collom P. T. Anastas ACS Sustainable Chem. Eng. 2015 3 1234 1240
51. M. Ferreira M. F. Pinto O. S. G. P. Soares M. F. R. Pereira J. J. M. Órfão J. L. Figueiredo I. C. Neves A. M. Fonseca P. Parpot Electrochim. Acta 2012 60 278 286
52. C. H. Lam C. B. Lowe Z. Li K. N. Longe J. T. Rayburn M. A. Caldwell C. E. Houdek J. B. Maguire C. M. Saffron D. J. Miller J. E. Jackson Green Chem. 2015 17 601 609
53. H. Kishida F. Jin Z. Zhou T. Moriya H. Enomoto Chem. Lett. 2005 34 1560 1561
54. S. Kitano M. Yamauchi S. Hata R. Watanabe M. Sadakiyo Green Chem. 2016 18 3700
55. R. Ciriminna G. Palmisano C. D. Pina M. Rossi M. Pagliaro Tetrahedron Lett. 2006 47 6993 6995
56. H. A. Gasteiger N. Marković P. N. Ross E. J. Cairns J. Electrochem. Soc. 1994 141 1795 1803
57. L. Bhattacharyya and J. S. Rohrer, Applications of Ion Chromatography for Pharmaceutical and Biological Products, John Wiley & Sons, Inc., 2012, pp. 455-456, 10.1002/9781118147009.app2
58. A. Rahimi A. Ulbrich J. J. Coon S. S. Stahl Nature 2014 515 249 252
59. S. Khaitan D. A. Dzombak G. V. Lowry Environ. Eng. Sci. 2008 26 431 440
60. I. Doye J. Duchesne Appl. Geochem. 2003 18 1197 1213
61. R. C. Sahu R. K. Patel B. C. Ray J. Hazard. Mater. 2010 179 28 34
62. C. H. Lam C. B. Lowe Z. Li K. N. Longe J. T. Rayburn M. A. Caldwell C. E. Houdek J. B. Maguire C. M. Saffron D. J. Miller J. E. Jackson Green Chem. 2015 17 601 609
63. A. Cyr F. Chiltz P. Jeanson A. Martel L. Brossard J. Lessard H. Menard Can. J. Chem. 2000 78 307 315
64. W. Li J. Liu D. Y. Zhao Nat. Rev. Mater. 2016 1 17
65. G. Wang L. Zhang J. Zhang Chem. Soc. Rev. 2012 41 797 828
66. H. Vogt J. Appl. Electrochem. 1993 23 1323 1325
67. G. G. Botte Electrochem. Soc. Interface 2014 23 49 55
68. Alpha Hydroxy Acids, http://www.cosmeticsinfo.org/alpha-hydroxy-acids (accessed 19th June, 2016)