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Reaction Mechanisms in the Direct Carboxylation of Alcohols, Polyols, Cyclic Ethers, and Cyclic Amines to Afford Monomeric Compounds and Polymeric Materials

Chapter

Abstract

This chapter deals with the utilization of CO2 in the carboxylation of alcohols, diols, polyols, and epoxides to create a variety of compounds such as linear carbonates, cyclic monomeric carbonates, and polycarbonates. Homogeneous, heterogenized, and heterogeneous catalysts are described. The problem of “water elimination” is considered and routes for water-trapping discussed. DFT calculations used to support the reaction mechanism are presented with the identified transition states relevant to various mechanistic scenarios.

Keywords

Propene Carbonate Water Trap Cyclic Ether Glycerol Carbonate Oxidative Carbonylation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Delledonne D, Rivetti F, Romano U (2001) Developments in the production and application of dimethyl carbonate. Appl Catal A Gen 221(1–2):241–251Google Scholar
  2. 2.
    Shaikh AAG, Sivaram S (1996) Organic carbonates. Chem Rev 96:951–976, and references thereinGoogle Scholar
  3. 3.
    Tullo AH (2001) Fighting for position in polycarbonate. C&EN 79(15):15–16Google Scholar
  4. 4.
    Buysch HJ (1992) Carbonic acid esters. In: Ullmann’s encyclopedia of industrial chemistry, vol A5. VCH, Weinheim, pp 197–201Google Scholar
  5. 5.
    Aresta M, Dibenedetto A, He LN (2012) Analysis of demand for captured CO2 and products from CO2 conversion, a report exclusively for members of the carbon dioxide capture and conversion (CO2CC) program of the Catalyst Group Resources (TCGR)Google Scholar
  6. 6.
    Pacheco MA, Marshall CL (1997) Review of dimethyl carbonate (DMC) manufacture and its characteristics as a fuel additive. Energy Fuels 11(1):2–29Google Scholar
  7. 7.
    Aresta M, Dibenedetto A (2003) In: Aresta M (ed) Carbon dioxide: recovery and utilization. Kluwer, Dordrecht, pp 211–260Google Scholar
  8. 8.
    (2001) TEXACO studyGoogle Scholar
  9. 9.
    Société Nationale des Poudres et Explosifs (1973) Continuous manufacture of alkyl carbonates. FR 2163884, 1973 Fr. Patent, 7 ppGoogle Scholar
  10. 10.
    Damle SB (2000) Carbonic and carbonochloridic esters. In: Othmer K (ed) Encyclopedia of chemical technology, vol 5, 4th edn. Wiley, New York, NY, pp 77–97Google Scholar
  11. 11.
    Romano U, Tesei R, Massi MM, Rebora P (1980) Synthesis of dimethyl carbonate from methanol, carbon monoxide, and oxygen catalyzed by copper compounds. Ind Eng Chem Prod Res Dev 19(3):396–403Google Scholar
  12. 12.
    Romano U (1993) Dimethyl carbonate and its production technology. Chim Ind Milan 75(4):303–306Google Scholar
  13. 13.
    Perrotti E, Cipriani G (1974) Process for the preparation of esters of carbonic acid. US Patent 3846468Google Scholar
  14. 14.
    Romano U, Tesei R, Cipriani G, Micucci L (1980) Method for the preparation of esters of carbonic acid. US Patent 4218391Google Scholar
  15. 15.
    Matsuzaki T, Nakamura A (1997) Dimethyl carbonate synthesis and other oxidative reactions using alkyl nitrites. Catal Surv Jpn 1:77–88Google Scholar
  16. 16.
    Nishihira K, Tanaka S, Kodama K, Kaneko T (1992) Process for preparing diester of carbonic acid. Eur Pat Appl EP501507Google Scholar
  17. 17.
    Aresta M, Dibenedetto A, di Bitonto L (2014) Cerium-based binary and ternary oxides in the transesterification of dimethylcarbonate with phenol. ChemSusChem 7(4):1155–1161Google Scholar
  18. 18.
    Bhanage BM, Fujita S, Ikushima Y, Torii K, Arai M (2003) Synthesis of dimethyl carbonate and glycols from carbon dioxide, epoxides and methanol using heterogeneous Mg containing smectite catalysts: effect of reaction variables on activity and selectivity performance. Green Chem 5:71–75Google Scholar
  19. 19.
    Bhanage BM, Fujita S, Ikushima Y, Arai M (2001) Synthesis of dimethyl carbonate and glycols from carbon dioxide, epoxides, and methanol using heterogeneous basic metal oxide catalysts with high activity and selectivity. Appl Catal A Gen 219:259–266Google Scholar
  20. 20.
    Tomishige K, Sakaihori T, Ikeda Y, Fujimoto K (1999) A novel method of direct synthesis of dimethyl carbonate from methanol and carbon dioxide catalyzed by zirconia. Catal Lett 58:225–229Google Scholar
  21. 21.
    Aresta M, Dibenedetto A, Pastore C (2003) Synthesis and characterization of Nb(OR)4[OC(O)OR] (R = Me, Et, Allyl) and their reaction with the parent alcohol to afford organic carbonates. Inorg Chem 42(10):3256–3261, and references thereinGoogle Scholar
  22. 22.
    Choi J-C, Sakakura T, Sako T (1999) Reaction of dialkyltin methoxide with carbon dioxide relevant to the mechanism of catalytic carbonate synthesis. J Am Chem Soc 121:3793–3794Google Scholar
  23. 23.
    Ballivet-Tkatchenko D, Douteau O, Stutzmann S (2000) Reactivity of carbon dioxide with n-butyl(phenoxy)-, (alkoxy)-, and (oxo)stannanes: insight into dimethyl carbonate synthesis. Organomet 19:4563–4567Google Scholar
  24. 24.
    Sanderson RT (1976) Chemical bonds and bond energy. Academic, New York, NYGoogle Scholar
  25. 25.
    Aresta M, Dibenedetto A, Fracchiolla E, Giannoccaro P, Pastore C, Pàpai I, Schubert G (2005) Mechanism of formation of organic carbonates from aliphatic alcohols and carbon dioxide under mild conditions promoted by carbodiimides. DFT calculation and experimental study. J Org Chem 70(16):6177–6186Google Scholar
  26. 26.
    Isaacs NS, O’Sullivan B, Verhaelen C (1999) High pressure routes to dimethyl carbonate from supercritical carbon dioxide. Tetrahedron 55:11949–11956Google Scholar
  27. 27.
    Sakakura T, Saito Y, Okano M, Choi J-C, Sako T (1998) Selective conversion of carbon dioxide to dimethyl carbonate by molecular catalysis. J Org Chem 63:7095–7096Google Scholar
  28. 28.
    Aresta M, Dibenedetto A, Pastore C, Pàpai I, Schubert G (2006) Reaction mechanism of the direct carboxylation of methanol to dimethylcarbonate: experimental and theoretical studies. Top Catal 40(1–4):71–81Google Scholar
  29. 29.
    Ballivet-Tkatchenko D, Jerphagnon T, Ligabue R, Plasseraud L, Poinsot D (2003) The role of distannoxanes in the synthesis of dimethyl carbonate from carbon dioxide. Appl Catal A Gen 255:93–99Google Scholar
  30. 30.
    Ballivet-Tkatchenko D, Chambrey S, Keiski R, Ligabue R, Plasseraud L, Richard P, Turunen H (2006) Direct synthesis of dimethyl carbonate with supercritical carbon dioxide: characterization of a key organotin oxide intermediate. Catal Today 115:80–87Google Scholar
  31. 31.
    Kohno K, Choi J-C, Ohshima Y, Yili A, Yasuda H, Sakakura T (2008) Reaction of dibutyltin oxide with methanol under CO2 pressure relevant to catalytic dimethyl carbonate synthesis. J Organomet Chem 693:1389–1392Google Scholar
  32. 32.
    Dibenedetto A, Angelini A (2014) Synthesis of organic carbonates. Adv Inorg Chem 66:25–81Google Scholar
  33. 33.
    Ballivet-Tkatchenko D, Chermette H, Plasseraud L, Walter O (2006) Insertion reaction of carbon dioxide into Sn–OR bond. Synthesis, structure and DFT calculations of di- and tetranuclear isopropylcarbonato tin(IV) complexes. Dalton Trans 43:5167–5175Google Scholar
  34. 34.
    Aresta M, Dibenedetto A, Angelini A (2014) Catalysis for the valorization of exhaust carbon: from CO2 to chemicals, materials, and fuels. Technological use of CO2. Chem Rev 114(3):1709–1742Google Scholar
  35. 35.
    Kizlink J, Pastucha I (1995) Preparation of dimethyl carbonate from methanol and carbon dioxide in the presence of Sn(IV) and Ti(IV) alkoxides and metal acetates. Collect Czech Chem Commun 60:687–692Google Scholar
  36. 36.
    Kohno K, Choi J-C, Ohshima Y, Yasuda H, Sakakura T (2008) Synthesis of dimethyl carbonate from carbon dioxide catalyzed by titanium alkoxides with polyether-type ligand. ChemSusChem 1:186–188Google Scholar
  37. 37.
    Dibenedetto A, Pastore C, Aresta M (2006) Direct carboxylation of alcohols to organic carbonates: comparison of the Group 5 element alkoxides catalytic activity. Catal Today 115:88–94Google Scholar
  38. 38.
    Kato M, Ito T (1985) Facile carbon dioxide uptake by zinc(II)-tetraazacycloalkane complexes. 1. Syntheses, characterizations, and chemical properties of (monoalkyl carbonato) (tetraaza-cycloalkane)zinc(II) complexes. Inorg Chem 24:504–505Google Scholar
  39. 39.
    Aresta M, Dibenedetto A, Nocito F, Pastore C (2008) Comparison of the behaviour of supported homogeneous catalysts in the synthesis of dimethylcarbonate from methanol and carbon dioxide: polystyrene-grafted tin-metallorganic species versus silesquioxanes linked Nb-methoxo species. Inorg Chim Acta 361:3215–3220Google Scholar
  40. 40.
    Sakakura T, Saito Y, Choi J-C, Sako T (2000) Synthesis of dimethyl carbonate from carbon dioxide: catalysis and mechanism. Polyhedron 19:573–576Google Scholar
  41. 41.
    Aresta M, Dibenedetto A, Angelini A (2013) From carbon dioxide to valuable products under homogeneous catalysis. In: Reedijk J, Poeppelmeier KBT (eds) Comprehensive inorganic chemistry II. Elsevier, Amsterdam, pp 563–586Google Scholar
  42. 42.
    Zhong SH, Kong LL, Li HS, Xiao XF (2002) Preparation of Ti2(OMe)4/SiO2 catalyst and its reactivity for DMC synthesis from CO2 and CH3OH. Ranliao Huaxue Xuebao 30(5):454–458Google Scholar
  43. 43.
    Aresta M, Dibenedetto A, Nocito F, Angelini A, Gabriele B (2010) Synthesis and characterization of a novel polystyrene-tethered niobium methoxo species. Its application in the CO2-based carboxylation of methanol to afford dimethyl carbonate. Appl Catal A Gen 387:113–118Google Scholar
  44. 44.
    Fan B, Zhang J, Li R, Fan W (2008) In situ preparation of functional heterogeneous organotin catalyst tethered on SBA-15. Catal Lett 121:297–302Google Scholar
  45. 45.
    Aresta M, Dibenedetto A, Pastore C, Angelini A, Aresta B, Pápai I (2010) Influence of Al2O3 on the performance of CeO2 used as catalyst in the direct carboxylation of methanol to dimethylcarbonate and the elucidation of the reaction mechanism. J Catal 269:44–52Google Scholar
  46. 46.
    Tomishige K, Yoshida Y, Arai Y, Kado S, Kunimori K (2006) Direct synthesis of organic carbonates from the reaction of CO2 with methanol and ethanol over CeO2 catalysts. Catal Today 115:95–101Google Scholar
  47. 47.
    Tomishige K, Ikeda Y, Sakaihori T, Fujimoto K (2000) Catalytic properties and structure of zirconia catalysts for direct synthesis of dimethyl carbonate from methanol and carbon dioxide. J Catal 192:355–362Google Scholar
  48. 48.
    Ma J, Sun N, Zhang X, Zhao N, Xiao F, Wie W (2009) A short review of catalysis for CO2 conversion. Catal Today 148:221–231Google Scholar
  49. 49.
    Ikeda Y, Asadullah M, Fujimoto K, Tomishige K (2001) Structure of the active sites on H3PO4/ZrO2 catalysts for dimethyl carbonate synthesis from methanol and carbon dioxide. J Phys Chem B 105:10653–10658Google Scholar
  50. 50.
    Ikeda Y, Sakaihori T, Tomishige K, Fujimoto K (2000) Promoting effect of phosphoric acid on zirconia catalysts in selective synthesis of dimethyl carbonate from methanol and carbon dioxide. Catal Lett 66:59–62Google Scholar
  51. 51.
    Tomishige K, Furusawa Y, Ikeda Y, Asadullah M, Fujimoto K (2001) CeO2–ZrO2 solid solution catalyst for selective synthesis of dimethyl carbonate from methanol and carbon dioxide. Catal Lett 76:71–74Google Scholar
  52. 52.
    Allaoui LA, Acuissi A (2006) Effect of the Brønsted acidity on the behavior of CO2 methanol reaction. J Mol Catal A Chem 259:281–285Google Scholar
  53. 53.
    La KW, Song IK (2006) Direct synthesis of dimethyl carbonate from CH3OH and CO2 by H3PW12O40/CexTi1-xO2 catalyst. React Kinet Catal Lett 89:303–309Google Scholar
  54. 54.
    La KW, Jung JC, Kima H, Baeck SH, Song IK (2007) Effect of acid–base properties of H3PW12O40/CexTi1−xO2 catalysts on the direct synthesis of dimethyl carbonate from methanol and carbon dioxide: a TPD study of H3PW12O40/CexTi1−xO2 catalysts. J Mol Catal A Chem 269:41–45Google Scholar
  55. 55.
    Tkatchenko DB, Dibenedetto A (2010) Synthesis of linear and cyclic carbonates. In: Aresta M (ed) CO2 as chemical feedstock. Wiley-VCH, Weinheim, p 178Google Scholar
  56. 56.
    Jiang C, Guo Y, Wang C, Hu C, Wu Y, Wang E (2003) Synthesis of dimethyl carbonate from methanol and carbon dioxide in the presence of polyoxometalates under mild conditions. Appl Catal A Gen 256:203–212Google Scholar
  57. 57.
    Jung KT, Bell AT (2001) An in situ infrared study of dimethyl carbonate synthesis from carbon dioxide and methanol over zirconia. J Catal 204:339–347Google Scholar
  58. 58.
    Aresta M, Dibenedetto A, Pastore C, Cuocci C, Aresta B, Cometa S, De Giglio E (2008) Cerium(IV)oxide modification by inclusion of a hetero-atom: a strategy for producing efficient and robust nano-catalysts for methanol carboxylation. Catal Today 137:125–131Google Scholar
  59. 59.
    Finocchio E, Daturi M, Binet C, Lavalley JC, Blanchard G (1999) Thermal evolution of the adsorbed methoxy species on CexZr1-xO2 solid solution samples: a FT-IR study. Catal Today 52:53–63Google Scholar
  60. 60.
    Dibenedetto A, Aresta M, Angelini A, Ethiraj J, Aresta BM (2012) Synthesis, characterization, and use of NbV/CeIV-mixed oxides in the direct carboxylation of ethanol by using pervaporation membranes for water removal. Chem-A Eur J 18(33):10324–10334Google Scholar
  61. 61.
    Sakakura T, Saito Y, Choi J-C, Masuda T, Sako T, Oriyama T (1999) Metal-catalyzed carbonate synthesis from carbon dioxide and acetals. J Org Chem 64:4506–4508Google Scholar
  62. 62.
    Aresta M, Dibenedetto A, Di Leo C, Tommasi I, Amidio E (2003) The first synthesis of a cyclic carbonate from a ketal in sc-CO2. J Supercrit Fluids 25:177–180Google Scholar
  63. 63.
    Honda M, Kuno S, Sonehara S, Fujimoto K, Suzuki K, Nakagawa Y, Tomishige K (2011) Tandem carboxylation-hydration reaction system from methanol, CO2 and benzonitrile to dimethyl carbonate and benzamide catalyzed by CeO2. ChemCatChem 3(2):365–370Google Scholar
  64. 64.
    Tomishige K, Kunimori K (2002) Catalytic and direct synthesis of dimethyl carbonate starting from carbon dioxide using CeO2-ZrO2 solid solution heterogeneous catalyst: effect of H2O removal from the reaction system. Appl Catal A Gen 237:103–109Google Scholar
  65. 65.
    Carafa M, Quaranta E (2009) Synthesis of organic carbamates without using phosgene: carbonylation of amines with carbonic acid diesters. Mini-Rev Org Chem 6(3):168–183Google Scholar
  66. 66.
    Honda M, Kuno S, Begum N, Fujimoto K-I, Suzuki K, Nakagawa Y, Tomishige K (2010) Catalytic synthesis of dialkyl carbonate from low pressure CO2 and alcohols combined with acetonitrile hydration catalyzed by CeO2. App Catal A Gen 384(1–2):165–170Google Scholar
  67. 67.
    Honda M, Suzuki A, Noorjahan B, Fujimoto K-I, Suzuki K, Tomishige K (2009) Low pressure CO2 to dimethyl carbonate by the reaction with methanol promoted by acetonitrile hydration. Chem Commun 30:4596–4598Google Scholar
  68. 68.
    Eta V, Arbvela PM, Leino AR, Kordàs TD, Salmi T, Murzoin DY, Perikkolas J (2010) Synthesis of dimethyl carbonate from methanol and carbon dioxide: circumventing thermodynamic limitations. Ind Eng Chem Res 49:9609–9617Google Scholar
  69. 69.
    Eta V, Mäki-Arvela P, Wärnå J, Salmi T, Mikkola J-P, Murzin DY (2011) Kinetics of dimethyl carbonate synthesis from methanol and carbon dioxide over ZrO2–MgO catalyst in the presence of butylene oxide as additive. Appl Catal A Gen 404:39–46Google Scholar
  70. 70.
    Leino E, Mäki-Arvela P, Eränen K, Tenho M, Murzin DY, Salmi T, Mikkola JP (2011) Enhanced yields of diethyl carbonate via one-pot synthesis from ethanol, carbon dioxide and butylene oxide over cerium (IV) oxide. Chem Eng J 176–177:124–133Google Scholar
  71. 71.
    Leino E, Mäki-Arvela P, Eta V, Kumar N, Demoisson F, Samikannu A, Leino AR, Shchukarev A, Murzin DY, Mikkola J-P (2013) The influence of various synthesis methods on the catalytic activity of cerium oxide in one-pot synthesis of diethyl carbonate starting from CO2, ethanol and butylene oxide. Catal Today 210:47–54Google Scholar
  72. 72.
    Wagner A, Haas W (1994) Process for producing dialkyl carbonate. WO Patent 022805Google Scholar
  73. 73.
    Cheong M, Kim S-C, Park JB (1997) Dimethyl carbonate synthesis via carbon dioxide activation in the presence of iodide catalysts. New J Chem 21:1143–1145Google Scholar
  74. 74.
    Aresta M, Dibenedetto A, Angelini A, Pàpai I (2014) Reaction mechanisms in the direct carboxylation of alcohols for the synthesis of acyclic carbonates. Top Catal 58(1):2–14Google Scholar
  75. 75.
    Aresta M, Dibenedetto A, Stufano P, Aresta BM, Maggi S, Papai I, Rokob TA, Gabriele B (2010) The solid state structure and reactivity of NbCl5 · (N, N-dicyclohexylurea) in solution: evidence for co-ordinated urea dehydration to the relevant carbodiimide. Dalton Trans 39:6985–6992Google Scholar
  76. 76.
    Aresta M, Dibenedetto A, Devita C, Bourova OA, Chupakhin ON (2004) New catalysts for the conversion of urea into carbamates and carbonates with C1 and C2 alcohols. Stud Surf Catal 153:213–220Google Scholar
  77. 77.
    Zhao W, Peng W, Wang D, Zhao N, Li J, Xiao F, Wei W, Sun Y (2009) Zinc oxide as the precursor of homogenous catalyst for synthesis of dialkyl carbonate from urea and alcohols. Catal Commun 10:655–658Google Scholar
  78. 78.
    Wang H, Wang M, Zhao W, Wei W, Sun Y (2010) Reaction of zinc oxide with urea and its role in urea methanolysis. React Kinet Mech Catal 99:381–389Google Scholar
  79. 79.
    Dubois JL (2011) Amination of organic substrates method for the co-production of non-cyclic carbonates and amino acids. EP Patent 2137133B1Google Scholar
  80. 80.
    Wang M, Zhao N, Wei W, Sun Y (2005) Synthesis of dimethyl carbonate from urea and methanol over ZnO. Ind Eng Chem Res 44(19):7596–7599Google Scholar
  81. 81.
    Zhao W, Wang F, Peng W, Zhao N, Li J, Xiao F, Wei W, Sun Y (2008) Synthesis of dimethyl carbonate from methyl carbamate and methanol with zinc compounds as catalysts. Ind Eng Chem Res 47:5913–5917Google Scholar
  82. 82.
    Gaoa Y, Penga W, Zhaoa N, Wei W, Sun Y (2011) A DFT study on the reaction mechanism for dimethyl carbonate synthesis from methyl carbamate and methanol. J Mol Catal A Chem 35:29–40Google Scholar
  83. 83.
    Dibenedetto A, Angelini A, Fasciano S, Papai I, Curulla F, Aresta M (2014) The reaction mechanism in the ethanolysis of urea with transition metal based catalysts: DFT calculations and experiments. J CO2 Util 8:27–33Google Scholar
  84. 84.
    Wang M, Wang H, Zhao N, Wei W, Sun Y (2007) High-yield synthesis of dimethyl carbonate from urea and methanol using a catalytic distillation process. Ind Eng Chem Res 46(9):2683–2687Google Scholar
  85. 85.
    Saleh RY, Michaelson RC, Suciu EN, Kuhlmann B (1994) Dialkyl isocyanato tin alcoholate catalysts and dimers thereof. US Patent 5,561,094Google Scholar
  86. 86.
    Ryu JY (2000) Catalyst for making dialkyl carbonates. US Patent 6010976 AGoogle Scholar
  87. 87.
    Lin H, Yang B, Sun J, Wang X, Wang D (2004) Kinetics studies for the synthesis of dimethyl carbonate from urea and methanol. Chem Eng J 103:21–27Google Scholar
  88. 88.
    Wang M, Wang H, Zhao N, Wei W, Sun Y (2006) Synthesis of dimethyl carbonate from urea and methanol over solid base catalysts. Catal Commun 7:6–10Google Scholar
  89. 89.
    Guo L, Zhao X, An H, Wang Y (2012) Catalysis by lead oxide for diethyl carbonate synthesis from ethyl carbamate and ethanol. Chin J Catal 33:595–600Google Scholar
  90. 90.
    Fan M-M, Wang H, Zhang P-B, Ni BQ (2012) Synthesis, characterization and catalysis performance of ionic liquid 1-butyl-3-methylimidazolium chlorozincate. Chin J Inorg Chem 28:1333–1337Google Scholar
  91. 91.
    Wang H, Lu B, Wang X, Zhang J, Cai QI (2009) Highly selective synthesis of dimethyl carbonate from urea and methanol catalyzed by ionic liquids. Fuel Proc Technol 90:1198–1201Google Scholar
  92. 92.
    Joe W, Lee HJ, Hong UG, Anh YS, Song CJ, Kwon BJ, Song IK (2012) Urea methanolysis to dimethyl carbonate over ZnO–CeO2–MO (MO: La2O3, Y2O3, Co2O3, Ga2O3, and ZrO2) catalysts. J Ind Eng Chem 18:1730–1735Google Scholar
  93. 93.
    Joe W, Lee HJ, Hong UG, Anh YS, Song CJ, Kwon BJ, Song IK (2012) Synthesis of dimethyl carbonate from urea and methanol over ZnO(X)–CeO2(1 − X) catalysts prepared by a sol–gel method. J Ind Eng Chem 18:1018–1022Google Scholar
  94. 94.
    Wang D, Zhang X, Gao Y, Xiao F, Wei W, Sun Y (2010) Zn/Fe mixed oxide: heterogeneous catalyst for the synthesis of dimethyl carbonate from methyl carbamate and methanol. Catal Commun 11:430–433Google Scholar
  95. 95.
    Wang D, Zhang X, Zhao W, Peng W, Zhao N, Xiao F, Wei W, Sun Y (2010) Synthesis of dimethyl carbonate from methyl carbamate and methanol catalyzed by mixed oxides from hydrotalcite-like compounds. J Phys Chem Sol 71:427–430Google Scholar
  96. 96.
    Ryu JY, Gelbein AP (2001) Process and catalyst for making dialkyl carbonates. US Patent 6392078 B1Google Scholar
  97. 97.
    Huang S, Ma J, Li J, Zhao N, Wei W, Sun Y (2008) Efficient propylene carbonate synthesis from propylene glycol and carbon dioxide via organic bases. Catal Commun 9:276–280Google Scholar
  98. 98.
    Wu LX, Wang H, Tu Z-Y, Ding B-B, Xiao Y, Lu J-X (2012) Synthesis of cyclic carbonates from CO2 and diols via electrogenerated N-heterocyclic carbenes. Int J Electrochem Sci 7:11540–11549Google Scholar
  99. 99.
    Aresta M, Dibenedetto A, Nocito F, Pastore C (2006) A study on the carboxylation of glycerol to glycerol carbonate with carbon dioxide: the role of the catalyst, solvent and reaction conditions. J Mol Catal 257:149–153Google Scholar
  100. 100.
    Honda M, Tamura M, Nakao K, Suzuki K, Nakagawa Y, Tomishige K (2014) Direct cyclic carbonate synthesis from CO2 and diol over carboxylation/hydration cascade catalyst CeO2 with 2-cyano-pyridine. ACS Catal 4:1893–1896Google Scholar
  101. 101.
    Carrera G, Visak Z, Bogel-Lukasik R, Nunes Da Ponte M (2011) Thermodynamic studies for the synthesis of 1,2-glycerol carbonate from CO2 and glycerol. ICCDU XI, Dijon-FR, September 2011, Book of Abstracts, OC62, p 81Google Scholar
  102. 102.
    Vieville C, Yoo JW, Palet S, Mouloungui Z (1998) Synthesis of glycerol carbonate by direct carbonatation of glycerol in supercritical CO2 in the presence of zeolites and ion exchange resins. Catal Lett 56:245–247Google Scholar
  103. 103.
    Aresta M, Dibenedetto A, Nocito F, Ferragina C (2009) Valorization of bio-glycerol: new catalytic materials for the synthesis of glycerol carbonate via glycerolysis of urea. J Catal 268:106–114Google Scholar
  104. 104.
    Aresta M, Dibenedetto A, Nocito F, Dubois JL (2010) Synthesis process of polyol carbonate from polyols, conducted in using a solvent selective for polyols carbonates. WO Patent WO2010040786 A3Google Scholar
  105. 105.
    Dibenedetto A, Nocito F, Angelini A, Papai I, Aresta M, Mancuso R (2013) Catalytic synthesis of hydroxymethyl-2-oxazolidinones from glycerol or glycerol carbonate and urea. ChemSusChem 6(2):345–352Google Scholar
  106. 106.
    Dibenedetto A, Angelini A, Aresta M, Ethiraj J, Fragale C, Nocito F (2011) Converting wastes into added value products: from glycerol to glycerol carbonate, glycidol and epichlorohydrin using environmentally friendly synthetic routes. Tetrahedron 67:1308–1313Google Scholar
  107. 107.
    Aresta M, Dibenedetto A (2002) Carbon dioxide as building block for the synthesis of organic carbonates: behavior of homogeneous and heterogeneous catalysts in the oxidative carboxylation of olefins. J Mol Catal 182–183:399–409Google Scholar
  108. 108.
    Aresta M, Quaranta E, Ciccarese A (1987) Direct synthesis of 1,3-benzodioxol-2-one from styrene, dioxygen and carbon dioxide promoted by Rh(I). J Mol Catal 41:355–359Google Scholar
  109. 109.
    Aresta M, Dibendetto A, Gianfrate L, Pastore C (2003) Nb(V) compounds as epoxides carboxylation catalysts: the role of the solvent. J Mol Catal A Gen 204–205:245–252Google Scholar
  110. 110.
    Aresta M, Dibendetto A, Gianfrate L, Pastore C (2003) Enantioselective synthesis of organic carbonates promoted by Nb(IV) and Nb(V) catalysts. Appl Catal A Gen 255:5–11Google Scholar
  111. 111.
    Aresta M, Fragale C, Quaranta E, Tommasi I (1992) Carbon dioxide as modulator of the oxidative properties of dioxygen in the presence of transition metal systems. J Chem Soc Chem Commun 4:315–317Google Scholar
  112. 112.
    Dibenedetto A, Aresta M, Nocito F, Pastore C, Venezia AM, Chirykalova E, Kononenko VI, Shevchenko VG, Chupova IA (2006) Synthesis of cyclic carbonates from epoxides: use of reticular oxygen of Al2O3 or Al2O3-supported CeOx for the selective epoxidation of propene. Catal Today 115:117–123Google Scholar
  113. 113.
    Dibenedetto A, Aresta M, Distaso M, Pastore C, Venezia AM, Liu C-J, Zhang M (2008) High throughput experiment approach to the oxidation of propene-to-propene oxide with transition-metal oxides as O-donors. Catal Today 137:44–51Google Scholar
  114. 114.
    Aresta M, Tommasi I, Quaranta E, Fragale C, Mascetti J, Tranquille M, Galan F, Fouassier M (1996) Mechanism of formation of peroxocarbonates Rh(OOC(O)O)(Cl)P3 and their reactivity as oxygen transfer agents mimicking monooxygenases. The first evidence of CO2 insertion into the O-O bond of Rh(η2-O2) complexes. Inorg Chem 35:4254–4260Google Scholar
  115. 115.
    Aresta M, Quaranta E, Tommasi I, Mascetti J, Tranquille M, Borowiak M (1998) Formation of peroxocarbonates from L3Rh(O2)Cl and L2Ni(CO2): a unique reaction mechanism with carbon dioxide insertion into the O-O bond. Stud Surf Sci Catal 114:677–680Google Scholar
  116. 116.
    Aresta M, Dibenedetto A, Tommasi I (2000) Direct synthesis of organic carbonates by oxidative carboxylation of olefins catalyzed by metal oxides: developing green chemistry based on carbon dioxide. Appl Organomet Chem 14:799–802Google Scholar
  117. 117.
    Dibenedetto A, Aresta M. Unpublished resultsGoogle Scholar
  118. 118.
    Darensbourg DJ, Chung WC (2013) Relative basicities of cyclic ethers and esters. Chemistry of importance to ring-opening co- and terpolymerization reactions. Polyhedron 58:139–143Google Scholar
  119. 119.
    Tanaka Y (1967) Contribution of ring strain and basicity to reactivity of cyclic ethers in cationic copolymerization. J Macromol Sci A Chem 1(6):1059–1068Google Scholar
  120. 120.
    Dudev T, Lim C (1998) Ring strain energies from ab initio calculations. J Am Chem Soc 120:4450–4458Google Scholar
  121. 121.
    Dill JB, Grenberg A, Liebman JF (1979) Substituent effects on strain energies. J Am Chem Soc 101:6814–6818Google Scholar
  122. 122.
    Gordy W, Stanford SC (1941) Spectroscopic evidence for hydrogen bonds: comparison of proton‐attracting properties of liquids, III. J Chem Phys 9:204–214Google Scholar
  123. 123.
    Gordy W (1941) Spectroscopic evidence for hydrogen bonds: comparison of proton‐attracting properties of liquids, IV. J Chem Phys 9:215–223Google Scholar
  124. 124.
    Coates GW, Moore DR (2004) Discrete metal-based catalysts for the copolymerization of CO2 and epoxides: discovery, reactivity, optimization, and mechanism. Angew Chem Int Ed 43:6618–6639Google Scholar
  125. 125.
    Darensbourg DJ (2007) Making plastics from carbon dioxide: salen metal complexes as catalysts for the production of polycarbonates from epoxides and CO2. Chem Rev 107:2388–2410Google Scholar
  126. 126.
    Darensbourg DJ, Mackiewicz RM, Phelps AL, Billodeaux DR (2004) Copolymerization of CO2 and epoxides catalyzed by metal salen complexes. Acc Chem Res 37:836–844Google Scholar
  127. 127.
    Limura N, Takagi M, Iwane H, Ookago J (1995) Production of propylene carbonate. Japanese Patent 07,267,944Google Scholar
  128. 128.
    Inoue K, Oobuko H, Kokai Tokkyo Koho (1995) Production of alkylene carbonate. Japanese Patent 07,206,846Google Scholar
  129. 129.
    Inoue K, Oobkubo H, Kokai Tokkyo Koho (1995) Production of alkylene carbonate. Japanese Patent 07,206,847Google Scholar
  130. 130.
    Inoue K, Oobkubo H (1995) Production of alkylene carbonate. Japanese Patent 07,206,848Google Scholar
  131. 131.
    Inaba M, Hasegawa K, Nagaoka H, Kokai Tokkyo Koho (1997) Production of alkylene carbonate. Japanese Patent 09,067,365Google Scholar
  132. 132.
    Ichikawa S, Iwane H, Kokai Tokkyo Koho (1997) Production of alkylene carbonate. Japanese Patent 09,235,252Google Scholar
  133. 133.
    Tojo M, Fukuoka S (1991) Production of alkylene carbonate. Japanese Patent 03,120,270 to Asahi Chem IndGoogle Scholar
  134. 134.
    Bobyleva LI, Kryukov SI, Bobylev BN, Liakumovich AG, Surovstev A, Karpov OP, Akhmedyanova RA, Koneva SA (1992) Method for production of cyclic carbonates. Yaroslavskij Polit. Institut SU Patent 1,781,218Google Scholar
  135. 135.
    Mais FJ, Buysch HJ, Mendoza-Frohn C, Klausener A (1993) Method for the preparation of alkylene carbonates. EU Patent 543,249 to BayerGoogle Scholar
  136. 136.
    Kuran W, Listos T (1994) Initiation and propagation reactions in the copolymerization of epoxide with carbon dioxide by catalysts based on diethylzinc and polyhydric phenol. Macromol Chem Phys 195:977–984Google Scholar
  137. 137.
    Sakai T, Kihara N, Endo T (1995) Polymer reaction of epoxide and carbon dioxide. Incorporation of carbon dioxide into epoxide polymers. Macromolecules 28:4701–4706Google Scholar
  138. 138.
    Sakai T, Tsutsumi Y, Ema T (2008) Highly active and robust organic–inorganic hybrid catalyst for the synthesis of cyclic carbonates from carbon dioxide and epoxides. Green Chem 10:337–341Google Scholar
  139. 139.
    Darensbourg DJ, Holtcamp MW (1996) Catalysts for the reactions of epoxides and carbon dioxide. Coord Chem Rev 153:155–174Google Scholar
  140. 140.
    Inoe K, Oobkubo H (1995) Kokai Tokkyo Koho. Japanese Patent 07,206,847Google Scholar
  141. 141.
    Marquis ET, Sanderson JR (1994) Texaco Chemical Co. US Patent 5,283,365Google Scholar
  142. 142.
    Sone M, Sako T, Kamisawa C (1999) Kokai Tokkyo Koho. Japanese Patent 11,335,372Google Scholar
  143. 143.
    Song J, Zhang Z, Han B, Hu S, Li W, Xie Y (2008) Synthesis of cyclic carbonates from epoxides and CO2 catalyzed by potassium halide in the presence of β-cyclodextrin. Green Chem 10:1337–1341Google Scholar
  144. 144.
    Langanke J, Greiner L, Leitner W (2013) Substrate dependent synergistic and antagonistic effect of ammonium halide and polyoxometalate catalysts in the synthesis of cyclic carbonates from oleochemical epoxides and CO2. Green Chem 15:1173–1182Google Scholar
  145. 145.
    Zhou H, Wang YM, Zhang WZ, Qu JP, Lu XB (2011) N-Heterocyclic carbene functionalized MCM-41 as an efficient catalyst for chemical fixation of carbon dioxide. Green Chem 13:644–650Google Scholar
  146. 146.
    Decortes A, Castilla AM, Kleij AW (2010) Salen-complex-mediated formation of cyclic carbonates by cycloaddition of CO2 to epoxides. Angew Chem Int Ed 49:9822–9837Google Scholar
  147. 147.
    North M, Pasquale R, Young C (2010) Synthesis of cyclic carbonates from epoxides and CO2. Green Chem 12:1514–1539Google Scholar
  148. 148.
    Shen Y-M, Duan W-L, Shi M (2003) Chemical fixation of carbon dioxide catalyzed by binaphthyldiamino Zn, Cu, and Co salen-type complexes. J Org Chem 68:1559–1562Google Scholar
  149. 149.
    Lu X-B, Feng X-J, He R (2002) Catalytic formation of ethylene carbonate from supercritical carbon dioxide/ethylene oxide mixture with tetradentate Schiff-base complexes as catalyst. Appl Catal A 234:25–34Google Scholar
  150. 150.
    Paddock RL, Nguyen ST (2001) Chemical CO2 fixation: Cr(III) salen complexes as highly efficient catalysts for the coupling of CO2 and epoxides. J Am Chem Soc 123:11498–11499Google Scholar
  151. 151.
    Jing H, Edulji SK, Gibbs JM, Stern CL, Zhou H, Nguyen ST (2004) (Salen)tin complexes: syntheses, characterization, crystal structures, and catalytic activity in the formation of propylene carbonate from CO2 and propylene oxide. Inorg Chem 43(14):4315–4327Google Scholar
  152. 152.
    Kozak JA, Wu J, Su X, Simeon F, Hatton TA, Jamison TF (2013) Bromine catalysed conversion of CO2 and epoxides to cyclic carbonates under continuous flow conditions. J Am Chem Soc 135:18497–18501Google Scholar
  153. 153.
    Li Y, Zhao XQ, Wang Y (2005) Synthesis of dimethyl carbonate from methanol, propylene oxide and carbon dioxide over KOH/4A molecular sieve catalyst. Appl Catal A 279:205–208Google Scholar
  154. 154.
    Zhang X, Wei W, Sun Y (2005) International conference on carbon dioxide utilization. ICCDU VIII, OsloGoogle Scholar
  155. 155.
    Yano T, Matsui H, Koike T, Ishiguro H, Fujihara H, Yoshihara M, Maeshima T (1997) Magnesium oxide-catalysed reaction of carbon dioxide with anepoxide with retention of stereochemistry. Chem Commun 12:1129–1130Google Scholar
  156. 156.
    Yamaguchi K, Ebitani K, Yoshida T, Yoshida H, Kaneda KJ (1999) Mg–Al mixed oxides as highly active acid–base catalysts for cycloaddition of carbon dioxide to epoxides. Am Chem Soc 121:4526–4527Google Scholar
  157. 157.
    Aresta M, Dibendetto A (2001) 221st ACS national meeting, San Diego, Abstract 220Google Scholar
  158. 158.
    Shibata I, Mitani I, Imakuni A, Baba A (2011) Highly efficient synthesis of cyclic carbonates from epoxides catalyzed by indium tribromide system. Tetrahedron Lett 52:721–723Google Scholar
  159. 159.
    Machac JR Jr, Marquis ET, Woodrum SA (2000) US Patent 654,438Google Scholar
  160. 160.
    Kuruppathparambil RR, Tharun J, Dongwoo K, Kathalikkattil AC, Park DW (2014) Microwave-assisted one pot-synthesis of amino acid ionic liquids in water: simple catalysts for styrene carbonate synthesis under atmospheric pressure of CO2. Catal Sci Technol 4:963–970Google Scholar
  161. 161.
    Riduan SN, Zhang Y (2010) Recent developments in carbon dioxide utilization under mild conditions. Dalton Trans 39:3347–3357Google Scholar
  162. 162.
    Song J, Zhang B, Jiang T, Yang G, Han B (2011) Synthesis of cyclic carbonates and dimethyl carbonate using CO2 as a building block catalyzed by MOF-5/KI and MOF-5/KI/K2CO3. Front Chem Chin 6:21–30Google Scholar
  163. 163.
    Ulusoy M, Kilic A, Durgun Z, Tasci B, Cetinkaya J (2011) Silicon containing new salicylaldimine Pd(II) and Co(II) metal complexes as efficient catalysts in transformation of carbon dioxide (CO2) to cyclic carbonates. J Organomet Chem 696:1372–1379Google Scholar
  164. 164.
    Liang S, Liu H, Jiang T, Song J, Yang G, Han B (2011) Highly efficient synthesis of cyclic carbonates from CO2 and epoxides over cellulose/KI. Chem Commun 47:2131–2133Google Scholar
  165. 165.
    Buchard A, Kember MR, Sandeman KG, Williams CK (2011) A bimetallic iron(III) catalyst for CO2/epoxide coupling. Chem Commun 47:212–214Google Scholar
  166. 166.
    Dengler JE, Lehenmeier MW, Klaus S, Anderson CE, Herdtweck E, Riege B (2011) A one-component iron catalyst for cyclic propylene carbonate synthesis. Eur J Inorg Chem 3:336–343Google Scholar
  167. 167.
    Kilic A, Ulusoy M, Durgun M, Tasci Z, Yilmaz I, Cetinkaya B (2010) Hetero- and homo-leptic Ru(II) catalyzed synthesis of cyclic carbonates from CO2; synthesis, spectroscopic characterization and electrochemical properties. Appl Organomet Chem 24:446–453Google Scholar
  168. 168.
    Ulusoy M, Sahin O, Kilic A, Buyukgungor O (2011) Multinuclear Cu(II) Schiff base complex as efficient catalyst for the chemical coupling of CO2 and epoxides: synthesis, X-ray structural characterization and catalytic activity. Catal Lett 141:717–725Google Scholar
  169. 169.
    Clegg W, Harrington RW, North M, Pasquale R (2010) Cyclic carbonate synthesis catalysed by bimetallic aluminium-salen complexes. Chem Eur J 16:6828–6843Google Scholar
  170. 170.
    Castro-Osma JA, Alonso-Moreno C, Lara-Sánchez A, Martínez J, North M, Otero A (2014) Synthesis of cyclic carbonates catalysed by aluminium heteroscorpionate complexes. Catal Sci Technol 4:1674–1684Google Scholar
  171. 171.
    Eghbali N, Li C-J (2007) Conversion of carbon dioxide and olefins into cyclic carbonates in water. Green Chem 9:213–215Google Scholar
  172. 172.
    Kawanami H, Ikushima Y (2000) Chemical fixation of carbon dioxide to styrene carbonate under supercritical conditions with DMF in the absence of any additional catalysts. Chem Commun 21:2089–2090Google Scholar
  173. 173.
    Dupont J, De Souza RF, Suarez PAZ (2002) Ionic liquid (molten salt) phase organometallic catalysis. Chem Rev 102:3667–3692Google Scholar
  174. 174.
    Kawanami H, Sasaki A, Matsui K, Ikushima Y (2003) A rapid and effective synthesis of propylene. Chem Commun 7:896–897Google Scholar
  175. 175.
    Sugimoto H, Inoue SJ (2004) Copolymerization of carbon dioxide and epoxide. Polym Sci A Polym Chem 42:5561–5573Google Scholar
  176. 176.
    Sugimoto H, Ohtsuka H, Inoue S (2004) Alternating copolymerization of carbon dioxide and epoxide. Aluminum Schiff base complex – quartenary ammonium salt systems as novel initiators. Stud Surf Sci Catal 153:243–246Google Scholar
  177. 177.
    Super M, Berluche E, Costello C, Beckman E (1997) Copolymerization of 1,2-epoxycyclohexane and carbon dioxide using carbon dioxide as both reactant and solvent. Macromolecules 30:368–372Google Scholar
  178. 178.
    Inoue S (1987) In: Aresta M, Forti G (eds) Carbon dioxide as a source of carbon: chemical and biochemical uses, NATO-ASI Series C. Reidel Publishers, Dordrecht, p 331Google Scholar
  179. 179.
    Rokicki A, Kuran W (1981) The application of carbon dioxide as a direct material for polymer synthesis in polymerization and polycondensation. J Macromol Sci Rev Macromol Chem C21:135–136Google Scholar
  180. 180.
    Wu GP, Wei S-H, Ren WM, Lu X-B, Xu T-Q, Darensbourg DJ (2011) Perfectly alternating copolymerization of CO2 and epichlorohydrin using cobalt(III)-based catalyst systems. J Am Chem Soc 133(38):15191–15199Google Scholar
  181. 181.
    Darensbourg DJ, Andreatta JR, Moncada AI (2010) Polymers from carbon dioxide: polyucarbonates, polythiocarbonates and polyurethanes. In: Aresta M (ed) CO2 as chemical feedstock. Wiley-VCH, Weinheim, p 213Google Scholar
  182. 182.
    Li H, Niu Y (2011) Alternating copolymerization of CO2 with propylene oxide and terpolymerization with aliphatic epoxides by bifunctional cobalt salen complex. Polym J 43:121–125Google Scholar
  183. 183.
    Gosh A, Ramidi P, Pulla S, Sullivan SZ, Collom SL, Gartia Y, Munshi P, Biris AS, Noll BC, Berry BC (2010) Cycloaddition of CO2 to epoxides using a highly active Co(III) complex of tetraamidomacrocyclic ligand. Catal Lett 137:1–7Google Scholar
  184. 184.
    Kim BE, Varghese JK, Han YG, Lee BY (2010) Cobalt(III) complexes of various salen-type ligand bearing four quaternary ammonium salts and their reactivity for CO2/epoxide copolymerization. Bull Korean Chem Soc 31:829–834Google Scholar
  185. 185.
    Lee K, Ha JJY, Cao C, Park DW, Ha C-S, Kim I (2009) Effect of complexing agents of double metal cyanide catalyst on the copolymerizations of cyclohexene oxide and carbon dioxide. Catal Today 148:389–397Google Scholar
  186. 186.
    Darensbourg DJ (2014) Personal adventures in the synthesis of co-polymers from carbon dioxide and cyclic ethers. Adv Inorg Chem 66:1–23Google Scholar
  187. 187.
    (2012) After major downturn, global demand for polycarbonate growing again, Says IHS chemical report. IHS Online Pressroom, Englewood, CO, February 13, 2012. http://press.ihs.com/press-release/commodities-pricing-cost/after-major-downturn-global-demand-polycarbonate-growing-agai
  188. 188.
    Chemeurope.com (2011) Survey of polycarbonate market in China. Market Studies, Berlin. http://www.chemeurope.com/en/studies/13725/survey-of-polycarbonate-market-in-china.html
  189. 189.
    Demonstration plant for polycarbonates (PPC, PEC) polyols, Novomer, USA; Five commercial plants for BPA with 65 to 260 kt/y capacity, Asahi Kasei Corp., Japan; Polyols production and PPC with a capacity of 10 kt/y, Jinioong-Cas Chemail Co., China; Pilot plant for polyethercarbonates, Bayer Material Science; BASF: PPCGoogle Scholar
  190. 190.
    Soga K, Hosoda S, Nakamura K, Ikeda S (1976) A new synthetic route to 2-oxazolidones. J Chem Soc Chem Comm 16:617Google Scholar
  191. 191.
    Inoue S (1976) High polymers from carbon dioxide. Chemtech 6(9):588–594Google Scholar
  192. 192.
    Ihata O, Kayaki Y, Ikaryia T (2004) Synthesis of thermoresponsive polyurethane from 2-methylaziridine and supercritical carbon dioxide. Angew Chem Int Ed 43:717–719Google Scholar

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© Springer-Verlag Berlin Heidelberg 2016

Authors and Affiliations

  1. 1.Chemical and Biomolecular Engineering DepartmentNUSSingaporeSingapore
  2. 2.CIRCCPisaItaly
  3. 3.Department of Chemistry and CIRCCUniversity of BariBariItaly

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