Synthesis of cyclic carbonates from CO2 and diols via electrogenerated cyanomethyl anion

Greenhouse Gases: Science and Technology

Volumn 2, Issue 1, 2012, Pages 59-65

  Wang, Huan ^a   Wu, La Xia ^a   Zhao, Jian Qing ^a   Li, Rui Na ^a   Zhang, Ai Jian ^b   Kajiura, Hisashi ^b   Li, Yong Ming ^b   Lu, Jia Xing ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b Sony (China) Ltd   (China)

Author keywords

carbon dioxide; cyclic carbonate; diols; electrogenerated cyanomethyl anion; electrosynthesis

Indexed keywords

CARBONATES; CATHODES; ELECTROLYTES; IONS;

CYCLIC CARBONATES; DIOLS; ELECTROGENERATED CYANOMETHYL ANIONS; ELECTROSYNTHESIS; REACTION CONDITIONS; SUPPORTING ELECTROLYTE; SYNTHESIS OF CYCLIC CARBONATES;

CARBON DIOXIDE;

EID: 84859784583     PISSN: None     EISSN: 21523878     Source Type: Journal    
DOI: 10.1002/ghg.42     Document Type: Article

References (38)

1. Sakakura T, and, Kohno K,. The synthesis of organic carbonates from carbon dioxide. Chem Commun 45: 1312-1330 (2009).
2. Dai WL, Luo SL, Yin SF, and, Au CT,. The direct transformation of carbon dioxide to organic carbonates over heterogeneous catalysts. Appl Catal A-Gen 366: 2-12 (2009).
3. Tomishige K, Yasuda H, Yoshida Y, Nurunnabi M, Li BT, and, Kunimori K,. Novel route to propylene carbonate: Selective synthesis from propylene glycol and carbon dioxide. Catal Lett 95: 45-49 (2004).
4. Tomishige K, Yasuda H, Yoshida Y, Nurunnabi M, Li BT, and, Kunimori K,. Catalytic performance and properties of ceria based catalysts for cyclic carbonate synthesis from glycol and carbon dioxide. Green Chem 6: 206-214 (2004).
5. 2SnO as a catalyst. J Mol Catal A-Chem 304: 1-7 (2009).
6. Zhao XQ, Sun N, Wang SF, Li F, and, Wang YJ,. Synthesis of propylene carbonate from carbon dioxide and 1,2-propylene glycol over zinc acetate catalyst. Ind Eng Chem Res 47: 1365-1369 (2008). (Pubitemid 351488401)
7. Huang SY, Ma J, Li JP, Zhao N, Wei W, and, Sun YH,. Efficient propylene carbonate synthesis from propylene glycol and carbon dioxide via organic bases. Catal Commun 9: 276-280 (2008). (Pubitemid 350137915)
8. Du Y, He LN, and, Kong DL,. Magnesium-catalyzed synthesis of organic carbonate from 1,2-diol/alcohol and carbon dioxide. Catal Commun 9: 1754-1758 (2008).
9. Huang SY, Liu SG, Li JP, Zhao N, Wei W, and, Sun YH,. Modified zinc oxide for the direct synthesis of propylene carbonate from propylene glycol and carbon dioxide. Catal Lett 118: 290-294 (2007). (Pubitemid 47501736)
10. Huang SY, Liu SG, Li JP, Zhao N, Wei W, and, Sun YH,. Effective synthesis of propylene carbonate from propylene glycol and carbon dioxide by alkali carbonates. Catal Lett 112: 187-191 (2006). (Pubitemid 44916599)
11. Aresta M, Dibenedetto A, Nocito F, and, Pastore C,. 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 A-Chem 257: 149-153 (2006). (Pubitemid 44332316)
12. 2 under supercritical conditions. J Mol Catal A-Chem 241: 233-237 (2005).
13. Wang H, Zhang K, Liu YZ, Lin MY, and, Lu, JX,. Electrochemical carboxylation of cinnamate esters in MeCN. Tetrahedron 64: 314-318 (2008). (Pubitemid 350166439)
14. 4. Electrochem Commun 9: 2235-2239 (2007). (Pubitemid 47268863)
15. Chowdhury MA, Senboku H, and, Tokuda M,. Electrochemical carboxylation of bicyclo[n.1.0]alkylidene derivatives. Tetrahedron 60: 475-481 (2004). (Pubitemid 38010256)
16. Zhang K, Wang H, Zhao SF, Niu DF, and, Lu JX,. Asymmetric electrochemical carboxylation of prochiral acetophenone: An efficient route to optically active atrolactic acid via selective fixation of carbon dioxide. J Electroanal Chem 630: 35-41 (2009).
17. Bandeira MCE, and, Maia G,. Electrocarboxylation of 2-methylhalogen-9,10- anthraquinones. Electrochim Acta 53: 4512-4519 (2008).
18. Scialdone O, Sabatino MA, Belfiore C, Galia A, Paternostro MP, and, Filardo G,. An unexpected ring carboxylation in the electrocarboxylation of aromatic ketones. Electrochim Acta 51: 3500-3505 (2006).
19. Niu DF, Xiao LP, Zhang AJ, Zhang GR, Tan QY, and, Lu JX,. Electrocatalytic carboxylation of aliphatic halides at silver cathode in acetonitrile. Tetrahedron 64: 10517-10520 (2008).
20. Yamauchi Y, Hara S, and, Senboku H,. Synthesis of 2-aryl-3,3,3- trifluoropropanoic acids using electrochemical carboxylation of (1-bromo-2,2,2-trifluoroethyl) arenes and its application to the synthesis of β, β, β-trifluorinated non-steroidal anti-inflammatory drugs. Tetrahedron 66: 473-479 (2010).
21. Scialdone O, Galia A, Filardo G, Isse AA, and, Gennaro A,. Electrocatalytic carboxylation of chloroacetonitrile at a silver cathode for the synthesis of cyanoacetic acid. Electrochim Acta 54: 634-642 (2008).
22. 2 and amines: improved synthesis of carbamates. Appl Organomet Chem 21: 941-944 (2007). (Pubitemid 350149464)
23. 4: Synthesis of carbamates. J Org Chem 72: 200-203 (2007). (Pubitemid 46068221)
24. 4): synthesis of organic carbonates under mild conditions. Green Chem 10: 202-206 (2008). (Pubitemid 351199054)
25. 2 system towards alcohols. Eur J Org Chem 1689-1693 (2001).
26. Casadei MA, Cesa S, Feroci M, and, Inesi A,. Facile stereoselective conversion of 1,2-diols into alkane-1,2-diyl carbonates. New J Chem 23: 433-436 (1999). (Pubitemid 29378817)
27. Yang HZ, Gu YL, Deng YQ, and, Shi F,. Electrochemical activation of carbon dioxide in ionic liquids: synthesis of cyclic carbonates under mild reaction conditions. Chem Commun 36: 274-275 (2002). (Pubitemid 34146485)
28. Tascedda P, Weidmann M, Dinjus E, and, Dunach E,. Nickel-catalyzed electrochemical carboxylation of epoxides: mechanistic aspects. Appl Organomet Chem 15: 141-144 (2001).
29. Casadei MA, Cesa S, and, Rossi L, Electrogenerated- base-promoted synthesis of organic carbonates from alcohols and carbon dioxide. Eur J Org Chem 2000: 2445-2448 (2000).
30. 2. Synthesis of 5-Methylene-1,3-oxazolidin-2-ones. J Org Chem 70: 7795-7798 (2005). (Pubitemid 41318549)
31. Feroci M, Casadei MA, Orsini M, Palombi L, and, Inesi A,. Cyanomethyl anion/carbon dioxide system: an electrogenerated carboxylating reagent. Synthesis of carbamates under mild and safe conditions. J Org Chem 68: 1548-1551 (2003). (Pubitemid 36232520)
32. Feroci M, Gennaro A, Inesi A, Orsini M, and, Palombi L,. Synthesis of chiral oxazolidin-2-ones by 1,2-amino alcohols, carbon dioxide and electrogenerated acetonitrile anion. Tetrahedron Lett 43: 5863-5865 (2002). (Pubitemid 34876397)
33. Feroci M, Lessard J, Orsini M, and, Inesi A,. Electrogenerated cyanomethyl anion in organic synthesis: a simple diastereoselective synthesis of cis-3-alkyl-1- -benzyl-4-ethoxycarbonyl-β-lactams. Tetrahedron Lett 46: 8517-8519 (2005). (Pubitemid 41568612)
34. Feroci M, Synthesis of β-lactams by 4-exo-tet cyclization process induced by electrogenerated cyanomethyl anion. Part 2: Stereochemical implications. Adv Synth Catal 349: 2177-2181 (2007).
35. Feroci M, Orsini M, Palombi L, Rossi L, and, Inesi A,. An electrochemical alternative strategy to the synthesis of β-lactams via NC4 bond formation. Electrochim Acta 50: 2029-2036 (2005). (Pubitemid 40231855)
36. Rossi L, Feroci M, and, Inesi A,. The electrogenerated cyanomethyl anion in organic synthesis. Mini-Rev Org Chem 2: 79-90 (2005).
37. Niu DF, Luo YW, Zhang L, Xiao L P, and, Lu JX,. Electrosynthesis of dimethyl carbonate from carbon dioxide and methanol under mild conditions. Chin J Org Chem 28: 832-836 (2008).
38. Feroci M, Chiarotto I, Rossi L, and, Inesi A,. Activation of elemental sulfur by electrogenerated cyanomethyl anion: synthesis of substituted 2-amino -thiophenes by the Gewald reaction. Adv Synth Catal 350: 2740-2746 (2008).