Homogeneous Reduction of Carbon Dioxide with Hydrogen

Review
Part of the following topical collections:
  1. Chemical Transformations of Carbon Dioxide

Abstract

Carbon dioxide (CO2), a key greenhouse gas produced from both anthropogenic and natural sources, has been recently considered to be an important C1 building-block for the synthesis of many industrial fuels and chemicals. Catalytic hydrogenation of CO2 using a homogeneous system is regarded as an efficient process for CO2 valorization. This approach leads to the direct products including formic acid (HCOOH), carbon monoxide (CO), methanol (MeOH), and methane (CH4). The hydrogenation of CO2 to CO followed by alkene carbonylation provides value-added compounds, which also avoids the tedious separation and transportation of toxic CO. Moreover, the reduction of CO2 with H2 in the presence of amines is of significance to attain fine chemicals through catalytic formylation and methylation reactions. The synthesis of higher alcohols and dialkoxymethane from CO2 and H2 has been demonstrated recently, which opens access to new molecular structures using CO2 as an important C1 source.

Keywords

Homogeneous catalysis Carbon dioxide Hydrogen Formic acid Methanol Methylation 

References

  1. 1.
    Doney SC, Fabry VJ, Feely RA, Kleypas JA (2009) Ann Rev Mar Sci 1:169–192CrossRefGoogle Scholar
  2. 2.
    Aresta M, Dibenedetto A (2007) Dalton Trans 28:2975–2992CrossRefGoogle Scholar
  3. 3.
    Alberico E, Nielsen M (2015) Chem Commun 51:6714–6725CrossRefGoogle Scholar
  4. 4.
    Kuhl KP, Cave ER, Abram DN, Jaramillo TF (2012) Energy Environ Sci 5:7050–7059CrossRefGoogle Scholar
  5. 5.
    Lu Q, Rosen J, Zhou Y, Hutchings GS, Kimmel YC, Chen JG, Jiao F (2014) Nat Commun 5:3242–3247Google Scholar
  6. 6.
    Porosoff MD, Yan BH, Chen JGG (2016) Energy Environ Sci 9:62–73CrossRefGoogle Scholar
  7. 7.
    Wang W, Wang S, Ma X, Gong J (2011) Chem Soc Rev 40:3703–3727CrossRefGoogle Scholar
  8. 8.
    Wang W-H, Himeda Y, Muckerman JT, Manbeck GF, Fujita E (2015) Chem Rev 115:12936–12973CrossRefGoogle Scholar
  9. 9.
    Appel AM, Bercaw JE, Bocarsly AB, Dobbek H, DuBois DL, Dupuis M, Ferry JG, Fujita E, Hille R, Kenis PJA, Kerfeld CA, Morris RH, Peden CHF, Portis AR, Ragsdale SW, Rauchfuss TB, Reek JNH, Seefeldt LC, Thauer RK, Waldrop GL (2013) Chem Rev 113:6621–6658CrossRefGoogle Scholar
  10. 10.
    Aresta M, Dibenedetto A, Angelini A (2014) Chem Rev 114:1709–1742CrossRefGoogle Scholar
  11. 11.
    Jessop PG, Ikariya T, Noyori R (1995) Chem Rev 95:259–272CrossRefGoogle Scholar
  12. 12.
    Arakawa H, Aresta M, Armor JN, Barteau MA, Beckman EJ, Bell AT, Bercaw JE, Creutz C, Dinjus E, Dixon DA, Domen K, DuBois DL, Eckert J, Fujita E, Gibson DH, Goddard WA, Goodman DW, Keller J, Kubas GJ, Kung HH, Lyons JE, Manzer LE, Marks TJ, Morokuma K, Nicholas KM, Periana R, Que L, Rostrup-Nielson J, Sachtler WMH, Schmidt LD, Sen A, Somorjai GA, Stair PC, Stults BR, Tumas W (2001) Chem Rev 101:953–996CrossRefGoogle Scholar
  13. 13.
    Leitner W (1995) Angew Chem Int Ed 34:2207–2221CrossRefGoogle Scholar
  14. 14.
    Inoue Y, Izumida H, Sasaki Y, Hashimoto H (1976) Chem Lett 5:863–864CrossRefGoogle Scholar
  15. 15.
    Himeda Y (2007) Eur J Inorg Chem 2007:3927–3941CrossRefGoogle Scholar
  16. 16.
    Jessop PG, Ikariya T, Noyori R (1994) Nature 368:231–233CrossRefGoogle Scholar
  17. 17.
    Tai C-C, Pitts J, Linehan JC, Main AD, Munshi P, Jessop PG (2002) Inorg Chem 41:1606–1614CrossRefGoogle Scholar
  18. 18.
    Vogt M, Gargir M, Iron MA, Diskin-Posner Y, Ben-David Y, Milstein D (2012) Chem Eur J 18:9194–9197CrossRefGoogle Scholar
  19. 19.
    Huff CA, Sanford MS (2013) ACS Catal 3:2412–2416CrossRefGoogle Scholar
  20. 20.
    Filonenko GA, van Putten R, Schulpen EN, Hensen EJM, Pidko EA (2014) ChemCatChem 6:1526–1530CrossRefGoogle Scholar
  21. 21.
    Filonenko GA, Cosimi E, Lefort L, Conley MP, Copéret C, Lutz M, Hensen EJM, Pidko EA (2014) ACS Catal 4:2667–2671CrossRefGoogle Scholar
  22. 22.
    Filonenko GA, Smykowski D, Szyja BM, Li G, Szczygieł J, Hensen EJM, Pidko EA (2015) ACS Catal 5:1145–1154CrossRefGoogle Scholar
  23. 23.
    Kothandaraman J, Goeppert A, Czaun M, Olah GA, Surya GK (2016) Prakash. Green Chem 18:5831–5838CrossRefGoogle Scholar
  24. 24.
    Graf E, Leitner W (1992) J Chem Soc Chem Commun 8:623–624CrossRefGoogle Scholar
  25. 25.
    Angermund K, Baumann W, Dinjus E, Fornika R, Görls H, Kessler M, Krüger C, Leitner W, Lutz F (1997) Chem Eur J 3:755–764CrossRefGoogle Scholar
  26. 26.
    Ezhova NN, Kolesnichenko NV, Bulygin AV, Slivinskii EV, Han S (2002) Russ Chem Bull 51:2165–2169CrossRefGoogle Scholar
  27. 27.
    Li Y-N, He L-N, Liu A-H, Lang X-D, Yang Z-Z, Yu B, Luan C-R (2013) Green Chem 15:2825–2829CrossRefGoogle Scholar
  28. 28.
    Bays JT, Priyadarshani N, Jeletic MS, Hulley EB, Miller DL, Linehan JC, Shaw WJ (2014) ACS Catal 4:3663–3670CrossRefGoogle Scholar
  29. 29.
    Burgemeister T, Kastner F, Leitner W (1993) Angew Chem Int Ed 32:739–741CrossRefGoogle Scholar
  30. 30.
    Fernández-Alvarez FJ, Iglesias M, Oro LA, Polo V (2013) ChemCatChem 5:3481–3494CrossRefGoogle Scholar
  31. 31.
    Tanaka R, Yamashita M, Nozaki K (2009) J Am Chem Soc 131:14168–14169CrossRefGoogle Scholar
  32. 32.
    Tanaka R, Yamashita M, Chung LW, Morokuma K, Nozaki K (2011) Organometallics 30:6742–6750CrossRefGoogle Scholar
  33. 33.
    Federsel C, Jackstell R, Beller M (2010) Angew Chem Int Ed 49:6254–6257CrossRefGoogle Scholar
  34. 34.
    Liu C, Xie J-H, Tian G-L, Li W, Zhou Q-L (2015) Chem Sci 6:2928–2931CrossRefGoogle Scholar
  35. 35.
    Gassner F, Leitner W (1993) J Chem Soc Chem Commun 19:1465–1466CrossRefGoogle Scholar
  36. 36.
    Horváth H, Laurenczy G, Kathó Á (2004) J Organomet Chem 689:1036–1045CrossRefGoogle Scholar
  37. 37.
    Kathó Á, Opre Z, Laurenczy G, Joó F (2003) J Mol Catal A: Chem 204–205:143–148CrossRefGoogle Scholar
  38. 38.
    Joó F, Laurenczy G, Karády P, Elek J, Nádasdi L, Roulet R (2000) Appl Organomet Chem 14:857–859CrossRefGoogle Scholar
  39. 39.
    Joo F, Joo F, Nadasdi L, Elek J, Laurenczy G, Nadasdi L (1999) Chem Commun 11:971–972CrossRefGoogle Scholar
  40. 40.
    Laurenczy G, Joó F, Nádasdi L (2000) Inorg Chem 39:5083–5088CrossRefGoogle Scholar
  41. 41.
    Elek J, Nádasdi L, Papp G, Laurenczy G, Joó F (2003) Appl Catal A 255:59–67CrossRefGoogle Scholar
  42. 42.
    Jószai I, Joó F (2004) J Mol Catal A: Chem 224:87–91CrossRefGoogle Scholar
  43. 43.
    Federsel C, Jackstell R, Boddien A, Laurenczy G, Beller M (2010) ChemSusChem 3:1048–1050CrossRefGoogle Scholar
  44. 44.
    Boddien A, Gärtner F, Federsel C, Sponholz P, Mellmann D, Jackstell R, Junge H, Beller M (2011) Angew Chem Int Ed 50:6411–6414CrossRefGoogle Scholar
  45. 45.
    Himeda Y, Onozawa-Komatsuzaki N, Sugihara H, Arakawa H, Kasuga K (2004) Organometallics 23:1480–1483CrossRefGoogle Scholar
  46. 46.
    Himeda Y, Miyazawa S, Hirose T (2011) ChemSusChem 4:487–493CrossRefGoogle Scholar
  47. 47.
    Himeda Y, Onozawa-Komatsuzaki N, Sugihara H, Kasuga K (2007) Organometallics 26:702–712CrossRefGoogle Scholar
  48. 48.
    Wang W-H, Hull JF, Muckerman JT, Fujita E, Himeda Y (2012) Energy Environ Sci 5:7923–7926CrossRefGoogle Scholar
  49. 49.
    Suna Y, Ertem MZ, Wang W-H, Kambayashi H, Manaka Y, Muckerman JT, Fujita E, Himeda Y (2014) Organometallics 33:6519–6530CrossRefGoogle Scholar
  50. 50.
    Hull JF, Himeda Y, Wang W-H, Hashiguchi B, Periana R, Szalda DJ, Muckerman JT, Fujita E (2012) Nat Chem 4:383–388CrossRefGoogle Scholar
  51. 51.
    Wang W-H, Muckerman JT, Fujita E, Himeda Y (2013) ACS Catal 3:856–860CrossRefGoogle Scholar
  52. 52.
    Azua A, Sanz S, Peris E (2011) Chem Eur J 17:3963–3967CrossRefGoogle Scholar
  53. 53.
    Jantke D, Pardatscher L, Drees M, Cokoja M, Herrmann WA, Kühn FE (2016) ChemSusChem 9:2849–2854CrossRefGoogle Scholar
  54. 54.
    Munshi P, Main AD, Linehan JC, Tai C-C, Jessop PG (2002) J Am Chem Soc 124:7963–7971CrossRefGoogle Scholar
  55. 55.
    Muller K, Sun Y, Heimermann A, Menges F, Niedner-Schatteburg G, van Wüllen C, Thiel WR (2013) Chem Eur J 19:7825–7834CrossRefGoogle Scholar
  56. 56.
    Muller K, Sun Y, Thiel WR (2013) ChemCatChem 5:1340–1343CrossRefGoogle Scholar
  57. 57.
    Lau CP, Chen YZ (1995) J Mol Catal A: Chem 101:33–36CrossRefGoogle Scholar
  58. 58.
    Erlandsson M, Landaeta VR, Gonsalvi L, Peruzzini M, Phillips AD, Dyson PJ, Laurenczy G (2008) Eur J Inorg Chem 2008:620–627CrossRefGoogle Scholar
  59. 59.
    Schmeier TJ, Dobereiner GE, Crabtree RH, Hazari N (2011) J Am Chem Soc 133:9274–9277CrossRefGoogle Scholar
  60. 60.
    Evans GO, Newell CJ (1978) Inorg Chim Acta 31:L387–L389CrossRefGoogle Scholar
  61. 61.
    Tai C-C, Chang T, Roller B, Jessop PG (2003) Inorg Chem 42:7340–7341CrossRefGoogle Scholar
  62. 62.
    Federsel C, Boddien A, Jackstell R, Jennerjahn R, Dyson PJ, Scopelliti R, Laurenczy G, Beller M (2010) Angew Chem Int Ed 49:9777–9780CrossRefGoogle Scholar
  63. 63.
    Ziebart C, Federsel C, Anbarasan P, Jackstell R, Baumann W, Spannenberg A, Beller M (2012) J Am Chem Soc 134:20701–20704CrossRefGoogle Scholar
  64. 64.
    Federsel C, Ziebart C, Jackstell R, Baumann W, Beller M (2012) Chem Eur J 18:72–75CrossRefGoogle Scholar
  65. 65.
    Langer R, Diskin-Posner Y, Leitus G, Shimon LJW, Ben-David Y, Milstein D (2011) Angew Chem Int Ed 50:9948–9952CrossRefGoogle Scholar
  66. 66.
    Zhang Y, MacIntosh AD, Wong JL, Bielinski EA, Williard PG, Mercado BQ, Hazari N, Bernskoetter WH (2015) Chem Sci 6:4291–4299CrossRefGoogle Scholar
  67. 67.
    Fong H, Peters JC (2015) Inorg Chem 54:5124–5135CrossRefGoogle Scholar
  68. 68.
    Rivada-Wheelaghan O, Dauth A, Leitus G, Diskin-Posner Y, Milstein D (2015) Inorg Chem 54:4526–4538CrossRefGoogle Scholar
  69. 69.
    Zhu F, Zhu-Ge L, Yang G, Zhou S (2015) ChemSusChem 8:609–612CrossRefGoogle Scholar
  70. 70.
    Bertini F, Mellone I, Ienco A, Peruzzini M, Gonsalvi L (2015) ACS Catal 5:1254–1265CrossRefGoogle Scholar
  71. 71.
    Bertini F, Gorgas N, Stöger B, Peruzzini M, Veiros LF, Kirchner K, Gonsalvi L (2016) ACS Catal 6:2889–2893CrossRefGoogle Scholar
  72. 72.
    Jeletic MS, Mock MT, Appel AM, Linehan JC (2013) J Am Chem Soc 135:11533–11536CrossRefGoogle Scholar
  73. 73.
    Jeletic MS, Helm ML, Hulley EB, Mock MT, Appel AM, Linehan JC (2014) ACS Catal 4:3755–3762CrossRefGoogle Scholar
  74. 74.
    Kumar N, Camaioni DM, Dupuis M, Raugei S, Appel AM (2014) Dalton Trans 43:11803–11806CrossRefGoogle Scholar
  75. 75.
    Watari R, Kayaki Y, Hirano S-I, Matsumoto N, Ikariya T (2015) Adv Synth Catal 357:1369–1373CrossRefGoogle Scholar
  76. 76.
    Zall CM, Linehan JC, Appel AM (2015) ACS Catal 5:5301–5305CrossRefGoogle Scholar
  77. 77.
    Zall CM, Linehan JC, Appel AM (2016) J Am Chem Soc 138:9968–9977CrossRefGoogle Scholar
  78. 78.
    Badiei YM, Wang W-H, Hull JF, Szalda DJ, Muckerman JT, Himeda Y, Fujita E (2013) Inorg Chem 52:12576–12586CrossRefGoogle Scholar
  79. 79.
    Tlili A, Blondiaux E, Frogneux X, Cantat T (2015) Green Chem 17:157–168CrossRefGoogle Scholar
  80. 80.
    Haynes P, Slaugh LH, Kohnle JF (1970) Tetrahedron Lett 11:365–368CrossRefGoogle Scholar
  81. 81.
    Schreiner S, Yu JY, Vaska L (1988) Inorg Chim Acta 147:139–141CrossRefGoogle Scholar
  82. 82.
    Schreiner S, Yu JY, Vaska L (1988) J Chem Soc Chem Commun 9:602–603CrossRefGoogle Scholar
  83. 83.
    Jessop PG, Hsiao Y, Ikariya T, Noyori R (1994) J Am Chem Soc 116:8851–8852CrossRefGoogle Scholar
  84. 84.
    Jessop PG, Hsiao Y, Ikariya T, Noyori R (1996) J Am Chem Soc 118:344–355CrossRefGoogle Scholar
  85. 85.
    Krocher O, Koppel RA, Baiker A (1997) Chem Commun 5:453–454CrossRefGoogle Scholar
  86. 86.
    Schmid L, Canonica A, Baiker A (2003) Appl Catal A 255:23–33CrossRefGoogle Scholar
  87. 87.
    Schmid L, Schneider M, Engel D, Baiker A (2003) Catal Lett 88:105–113CrossRefGoogle Scholar
  88. 88.
    Zhang L, Han Z, Zhao X, Wang Z, Ding K (2015) Angew Chem Int Ed 54:6186–6189CrossRefGoogle Scholar
  89. 89.
    Minato M, Zhou D-Y, Sumiura K-I, Hirabayashi R, Yamaguchi Y, Ito T (2001) Chem Commun 24:2654–2655CrossRefGoogle Scholar
  90. 90.
    Tsai JC, Nicholas KM (1992) J Am Chem Soc 114:5117–5124CrossRefGoogle Scholar
  91. 91.
    Hayashi H, Ogo S, Fukuzumi S (2004) Chem Commun 23:2714–2715CrossRefGoogle Scholar
  92. 92.
    Zhao G, Joó F (2011) Catal Commun 14:74–76CrossRefGoogle Scholar
  93. 93.
    Moret S, Dyson PJ, Laurenczy G (2014) Nat Commun 5:4017–4023CrossRefGoogle Scholar
  94. 94.
    Lu S-M, Wang Z, Li J, Xiao J, Li C (2016) Green Chem 18:4553–4558CrossRefGoogle Scholar
  95. 95.
    Rohmann K, Kothe J, Haenel MW, Englert U, Hölscher M, Leitner W (2016) Angew Chem Int Ed 55:8966–8969CrossRefGoogle Scholar
  96. 96.
    Tominaga K-I, Sasaki Y (2000) Catal Commun 1:1–3CrossRefGoogle Scholar
  97. 97.
    Jääskeläinen S, Haukka M (2003) Appl Catal A 247:95–100CrossRefGoogle Scholar
  98. 98.
    Kontkanen M-L, Oresmaa L, Moreno MA, Jänis J, Laurila E, Haukka M (2009) Appl Catal A 365:130–134CrossRefGoogle Scholar
  99. 99.
    Liu Q, Wu L, Fleischer I, Selent D, Franke R, Jackstell R, Beller M (2014) Chem Eur J 20:6888–6894CrossRefGoogle Scholar
  100. 100.
    Srivastava VK, Eilbracht P (2009) Catal Commun 10:1791–1795CrossRefGoogle Scholar
  101. 101.
    Ostapowicz TG, Schmitz M, Krystof M, Klankermayer J, Leitner W (2013) Angew Chem Int Ed 52:12119–12123CrossRefGoogle Scholar
  102. 102.
    Wu L, Liu Q, Fleischer I, Jackstell R, Beller M (2014) Nat Commun 5:3091–3096Google Scholar
  103. 103.
    Balaraman E, Gunanathan C, Zhang J, Shimon LJW, Milstein D (2011) Nat Chem 3:609–614CrossRefGoogle Scholar
  104. 104.
    Balaraman E, Ben-David Y, Milstein D (2011) Angew Chem Int Ed 50:11702–11705CrossRefGoogle Scholar
  105. 105.
    Yang X (2012) ACS Catal 2:964–970CrossRefGoogle Scholar
  106. 106.
    Han Z, Rong L, Wu J, Zhang L, Wang Z, Ding K (2012) Angew Chem Int Ed 51:13041–13045CrossRefGoogle Scholar
  107. 107.
    Mellmann D, Sponholz P, Junge H, Beller M (2016) Chem Soc Rev 45:3954–3988CrossRefGoogle Scholar
  108. 108.
    Miller AJM, Heinekey DM, Mayer JM, Goldberg KI (2013) Angew Chem Int Ed 52:3981–3984CrossRefGoogle Scholar
  109. 109.
    Savourey S, Lefèvre G, Berthet J-C, Thuéry P, Genre C, Cantat T (2014) Angew Chem Int Ed 53:10466–10470CrossRefGoogle Scholar
  110. 110.
    Neary MC, Parkin G (2015) Chem Sci 6:1859–1865CrossRefGoogle Scholar
  111. 111.
    Sordakis K, Tsurusaki A, Iguchi M, Kawanami H, Himeda Y, Laurenczy G (2016) Chem Eur J 22:15605–15608CrossRefGoogle Scholar
  112. 112.
    Tominaga K-I, Sasaki Y, Watanabe T, Saito M (1995) Bull Chem Soc Jpn 68:2837–2842CrossRefGoogle Scholar
  113. 113.
    K. Tominaga, Y. Sasaki, M. Kawai, T. Watanabe, M. Saito, Chem. Commun. 1993, 629-631Google Scholar
  114. 114.
    Tominaga K, Sasaki Y, Saito M, Hagihara K, Watanabe T (1994) J Mol Catal 89:51–56CrossRefGoogle Scholar
  115. 115.
    Tominaga KI, Sasaki Y, Hagihara K, Watanabe T, Saito M (1994) Chem Lett 8:1391–1394CrossRefGoogle Scholar
  116. 116.
    Li Y-N, Ma R, He L-N, Diao Z-F (2014) Catal Sci Technol 4:1498–1512CrossRefGoogle Scholar
  117. 117.
    Choudhury J (2012) ChemCatChem 4:609–611CrossRefGoogle Scholar
  118. 118.
    Huff CA, Sanford MS (2011) J Am Chem Soc 133:18122–18125CrossRefGoogle Scholar
  119. 119.
    Kothandaraman J, Goeppert A, Czaun M, Olah GA, Prakash GKS (2013) J Am Chem Soc 138:778–781CrossRefGoogle Scholar
  120. 120.
    Khusnutdinova JR, Garg JA, Milstein D (2015) ACS Catal 5:2416–2422CrossRefGoogle Scholar
  121. 121.
    Wesselbaum S, vom Stein T, Klankermayer J, Leitner W (2012) Angew Chem Int Ed 51:7499–7502CrossRefGoogle Scholar
  122. 122.
    Wesselbaum S, Moha V, Meuresch M, Brosinski S, Thenert KM, Kothe J, vom Stein T, Englert U, Holscher M, Klankermayer J, Leitner W (2015) Chem Sci 6:693–704CrossRefGoogle Scholar
  123. 123.
    Qian Q, Cui M, He Z, Wu C, Zhu Q, Zhang Z, Ma J, Yang G, Zhang J, Han B (2015) Chem Sci 6:5685–5689CrossRefGoogle Scholar
  124. 124.
    Thenert K, Beydoun K, Wiesenthal J, Leitner W, Klankermayer J (2016) Angew Chem Int Ed 55:12266–12269CrossRefGoogle Scholar
  125. 125.
    Beydoun K, vom Stein T, Klankermayer J, Leitner W (2013) Angew Chem Int Ed 52:9554–9557CrossRefGoogle Scholar
  126. 126.
    Li Y, Sorribes I, Yan T, Junge K, Beller M (2013) Angew Chem Int Ed 52:12156–12160CrossRefGoogle Scholar
  127. 127.
    Beydoun K, Ghattas G, Thenert K, Klankermayer J, Leitner W (2014) Angew Chem Int Ed 53:11010–11014CrossRefGoogle Scholar
  128. 128.
    Li Y, Yan T, Junge K, Beller M (2014) Angew Chem Int Ed 53:10476–10480CrossRefGoogle Scholar

Copyright information

© Springer International Publishing Switzerland 2017

Authors and Affiliations

  1. 1.State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghaiPeople’s Republic of China
  2. 2.Leibniz-Institut für Katalyse e.V. an der Universität RostockRostockGermany
  3. 3.Department of Chemical EngineeringUniversity of Engineering and Technology LahoreLahorePakistan

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