Journal of the American Chemical Society
Communication
alternatives to the formerly reported amine-based systems. With
(c) Olah, G. A. Angew. Chem., Int. Ed. 2005, 44, 2636. (d) Liu, C.; Yang,
B.; Tyo, E.; Seifert, S.; DeBartolo, J.; von Issendorff, B.; Zapol, P.; Vajda,
S.; Curtiss, L. A. J. Am. Chem. Soc. 2015, 137, 8676−8679. (e) Wang, W.
H.; Himeda, Y.; Muckerman, J. T.; Manbeck, G. F.; Fujita, E. Chem. Rev.
a suitable choice of base (KOH) and catalyst (C-5), a TOF as
−
1
high as 5420 h was obtained. The biphasic system also enabled
effective recycling of the precious metal catalyst and the
hydroxide base as well as convenient utilization of the produced
formate salts in a DFFC. Our next efforts in this context will be
2015, 115, 12936−12973. (f) Li, Y.-N.; Ma, R.; He, L.-N.; Diao, Z.-F.
Catal. Sci. Technol. 2014, 4, 1498−1512. (g) Kar, S.; Sen, R.; Goeppert,
A.; Prakash, G. K. S. J. Am. Chem. Soc. 2018, 140, 1580−1583.
(h) Wesselbaum, S.; Moha, V.; Meuresch, M.; Brosinski, S.; Thenert, K.
M.; Kothe, J.; Stein, T. v.; Englert, U.; Holscher, M.; Klankermayer, J.;
Leitner, W. Chem. Sci. 2015, 6, 693−704. (i) Wesselbaum, S.; Vom
Stein, T.; Klankermayer, J.; Leitner, W. Angew. Chem., Int. Ed. 2012, 51,
directed toward developing amine-free integrated CO capture
2
and conversion to methanol systems.
ASSOCIATED CONTENT
Supporting Information
■
7
1
499−7502. (j) Huff, C. A.; Sanford, M. S. J. Am. Chem. Soc. 2011, 133,
*
S
8122−18125. (k) Rezayee, N. M.; Huff, C. A.; Sanford, M. S. J. Am.
Chem. Soc. 2015, 137, 1028−1031. (l) Kar, S.; Goeppert, A.;
Kothandaraman, J.; Prakash, G. K. S. ACS Catal. 2017, 7, 6347−
6351. (m) Guan, C.; Pan, Y.; Ang, E. P. L.; Hu, J.; Yao, C.; Huang, M.-
H.; Li, H.; Lai, Z.; Huang, K.-W. Green Chem. 2018, 20, 4201−4205.
Figures S1−S17 and Table S1 (PDF)
(
(
n) Huff, C. A.; Sanford, M. S. ACS Catal. 2013, 3, 2412−2416.
o) Filonenko, G. A.; van Putten, R.; Schulpen, E. N.; Hensen, E. J. M.;
AUTHOR INFORMATION
Pidko, E. A. ChemCatChem 2014, 6, 1526−1530. (p) Zhang, Y.;
MacIntosh, A. D.; Wong, J. L.; Bielinski, E. A.; Williard, P. G.; Mercado,
B. Q.; Hazari, N.; Bernskoetter, W. H. Chem. Sci. 2015, 6, 4291−4299.
(q) Olah, G. A.; Goeppert, A.; Prakash, G. K. S. Beyond Oil and Gas: The
ORCID
Methanol Economy, 2nd ed.; Wiley-VCH: Weinheim, Germany, 2009.
6) (a) Kothandaraman, J.; Goeppert, A.; Czaun, M.; Olah, G. A.;
Prakash, G. K. S. J. Am. Chem. Soc. 2016, 138, 778−781. (b) Scott, M.;
Blas Molinos, B.; Westhues, C.; Francio, G.; Leitner, W. ChemSusChem
017, 10, 1085−1093. (c) Kothandaraman, J.; Goeppert, A.; Czaun,
M.; Olah, G. A.; Surya Prakash, G. K. Green Chem. 2016, 18, 5831−
838.
7) (a) Liu, Q.; Wu, L.; Gu
Notes
The authors declare no competing financial interest.
(
̀
2
ACKNOWLEDGMENTS
■
5
(
Support of our work by the Loker Hydrocarbon Research
Institute, USC, is gratefully acknowledged. S.K. thanks the
Carolyn C. Franklin and Morris S. Smith Foundations for
providing endowed Graduate Fellowships.
̈
lak, S.; Rockstroh, N.; Jackstell, R.; Beller,
M. Angew. Chem., Int. Ed. 2014, 53, 7085−7088. (b) Ziebart, C.;
Federsel, C.; Anbarasan, P.; Jackstell, R.; Baumann, W.; Spannenberg,
A.; Beller, M. J. Am. Chem. Soc. 2012, 134, 20701−20704.
(c) Kothandaraman, J.; Czaun, M.; Goeppert, A.; Haiges, R.; Jones,
J.-P.; May, R. B.; Prakash, G. K. S.; Olah, G. A. ChemSusChem 2015, 8,
442−1451. (d) Boddien, A.; Gartner, F.; Federsel, C.; Sponholz, P.;
Mellmann, D.; Jackstell, R.; Junge, H.; Beller, M. Angew. Chem., Int. Ed.
chez-de-Armas, R.;
Ahlquist, M. S. G. ACS Catal. 2016, 6, 2923−2929. (f) Bertini, F.;
Mellone, I.; Ienco, A.; Peruzzini, M.; Gonsalvi, L. ACS Catal. 2015, 5,
REFERENCES
■
1
̈
(
1) (a) Goeppert, A.; Czaun, M.; Prakash, G. K. S.; Olah, G. A. Energy
Environ. Sci. 2012, 5, 7833−7853. (b) Sanz-Per
R.; Didas, S. A.; Jones, C. W. Chem. Rev. 2016, 116, 11840−11876.
c) House, K. Z.; Baclig, A. C.; Ranjan, M.; van Nierop, E. A.; Wilcox, J.;
Herzog, H. J. Proc. Natl. Acad. Sci. U. S. A. 2011, 108, 20428−20433.
d) Macdowell, N.; Florin, N.; Buchard, A.; Hallett, J.; Galindo, A.;
Jackson, G.; Adjiman, C. S.; Williams, C. K.; Fennell, P.; Shah, N. Energy
Environ. Sci. 2010, 3, 1645−1669. (e) Yu, C.-h.; Huang, C.-h.; Tan, C.-s.
Aerosol Air Qual. Res. 2012, 12, 745−769. (f) Sinha, A.; Darunte, L. A.;
Jones, C. W.; Realff, M. J.; Kawajiri, Y. Ind. Eng. Chem. Res. 2017, 56,
50−764. (g) Darunte, L. A.; Oetomo, A. D.; Walton, K. S.; Sholl, D. S.;
Jones, C. W. ACS Sustainable Chem. Eng. 2016, 4, 5761−5768.
2) (a) Mahmoudkhani, M.; Keith, D. W. Int. J. Greenhouse Gas
́
ez, E. S.; Murdock, C.
2
011, 50, 6411−6414. (e) Marcos, R.; Xue, L.; San
́
(
1
254−1265. (g) Sordakis, K.; Dalebrook, A. F.; Laurenczy, G.
(
ChemCatChem 2015, 7, 2332−2339. (h) Horvat
Szabolcsi, R.; Katho,
́
h, H.; Papp, G.;
́
́
A.; Joo,
́
F. ChemSusChem 2015, 8, 3036−3038.
(i) Dai, Z.; Luo, Q.; Cong, H.; Zhang, J.; Peng, T. New J. Chem. 2017,
4
1, 3055−3060. (j) Langer, R.; Diskin-Posner, Y.; Leitus, G.; Shimon,
L. J. W.; Ben-David, Y.; Milstein, D. Angew. Chem., Int. Ed. 2011, 50,
948−9952.
8) Han, S.-J.; Yoo, M.; Kim, D.-W.; Wee, J.-H. Energy Fuels 2011, 25,
825−3834.
9) (a) Zeng, L.; Tang, Z. K.; Zhao, T. S. Appl. Energy 2014, 115, 405−
7
9
(
3
(
(
Control 2009, 3, 376−384. (b) Yoo, M.; Han, S.-J.; Wee, J.-H. J. Environ.
Manage. 2013, 114, 512−519. (c) Kianpour, M.; Sobati, M. A.;
Shahhosseini, S. Chem. Eng. Res. Des. 2012, 90, 2041−2050. (d) Ram
Reddy, M. K.; Xu, Z. P.; Lu, G. Q.; Diniz da Costa, J. C. Ind. Eng. Chem.
Res. 2006, 45, 7504−7509.
4
10. (b) An, L.; Chen, R. J. Power Sources 2016, 320, 127−139.
(
c) Jiang, J.; Wieckowski, A. Electrochem. Commun. 2012, 18, 41−43.
(
d) Li, Y.; Feng, Y.; Sun, X.; He, Y. Angew. Chem., Int. Ed. 2017, 56,
5
(
2
734−5737.
10) (a) Huang, C.; Xu, T.; Zhang, Y.; Xue, Y.; Chen, G. J. Membr. Sci.
007, 288, 1−12. (b) Jaime-Ferrer, J. S.; Couallier, E.; Viers, P.;
Durand, G.; Rakib, M. J. Membr. Sci. 2008, 325, 528−536.
11) (a) Crook, J.; Mousavi, A. Environ. Forensics 2016, 17, 211−217.
b) Garcia-Herrero, I.; Margallo, M.; Onandía, R.; Aldaco, R.; Irabien,
(
2
1
(
3) (a) Stolaroff, J. K.; Keith, D. W.; Lowry, G. V. Environ. Sci. Technol.
008, 42, 2728−2735. (b) Lackner, K. S. Eur. Phys. J.: Spec. Top. 2009,
76, 93−106.
4) (a) Cuellar-Franca, R. M.; Azapagic, A. J. CO2 Util. 2015, 9, 82−
́
(
1
02. (b) Mac Dowell, N.; Fennell, P. S.; Shah, N.; Maitland, G. C. Nat.
(
Clim. Change 2017, 7, 243. (c) von der Assen, N.; Jung, J.; Bardow, A.
Energy Environ. Sci. 2013, 6, 2721−2734. (d) Olah, G. A.; Goeppert, A.;
Prakash, G. K. S. J. Org. Chem. 2009, 74, 487. (e) Goeppert, A.; Olah, G.
A.; Prakash, G. K. S. Toward a Sustainable Carbon Cycle: The
Methanol Economy. Green Chemistry; Elsevier: 2018; Chapter 3.26, pp
19−962. (f) Olah, G. A.; Prakash, G. K. S.; Goeppert, A. J. Am. Chem.
Soc. 2011, 133, 12881−12898.
5) (a) Reller, C.; Poge, M.; Lißner, A.; Mertens, F. O. R. L. Environ.
A. Sustainable Production and Consumption 2017, 12, 44−58. (c) Seko,
M. Ind. Eng. Chem. Prod. Res. Dev. 1976, 15, 286−292.
(12) The hydrogenation of sodium carbonate to formate salt in our
system is surprising, and we are currently investigating the possible
reaction pathways.
9
(
̈
Sci. Technol. 2014, 48, 14799−14804. (b) Kar, S.; Kothandaraman, J.;
Goeppert, A.; Prakash, G. K. S. J. CO2 Util. 2018, 23, 212−218.
D
J. Am. Chem. Soc. XXXX, XXX, XXX−XXX