Production of glycerol carbonate from glycerol with aid of ionic liquid as catalyst

Chemical Engineering Journal

Volumn 297, Issue , 2016, Pages 128-138

  Ishak, Zati Ismah ^a   Sairi, Nor Asrina ^a   Alias, Yatimah ^a   Aroua, Mohamed Kheireddine Taieb ^a   Yusoff, Rozita ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Catalysis; Glycerol; Glycerol carbonate; Ionic liquids; Transesterification

Indexed keywords

CARBONATION; CATALYSIS; CATALYSTS; GLYCEROL; IONIC LIQUIDS; LIQUIDS; TRANSESTERIFICATION;

1-ETHYL-3-METHYLIMIDAZOLIUM ACETATES; CATALYTIC PERFORMANCE; GLYCEROL CARBONATE; GLYCEROL CONVERSIONS; IMIDAZOLIUM-BASED IONIC LIQUID; REACTION TEMPERATURE; TRANSESTERIFICATION REACTION; VALUE ADDED PRODUCTS;

CATALYST SELECTIVITY;

EID: 84962916514     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2016.03.104     Document Type: Article

References (54)

1. Quispe C.A.G., Coronado C.J.R., Carvalho J.A. Glycerol: production, consumption, prices, characterization and new trends in combustion. Renew. Sustain. Energy Rev. 2013, 27:475-493. 10.1016/j.rser.2013.06.017.
2. Anitha M., Kamarudin S.K., Kofli N.T. The potential of glycerol as a value-added commodity. Chem. Eng. J. 2016, 10.1016/j.cej.2016.03.012.
3. J.W. Yoo, Z. Mouloungui, A. Gaset, Method for producing an epoxide, in particular of glycidol, and installation for implementation, US6316641 B1, 2001, http://www.google.com/patents/US6316641.
4. Ang G.T., Tan K.T., Lee K.T. Recent development and economic analysis of glycerol-free processes via supercritical fluid transesterification for biodiesel production. Renew. Sustain. Energy Rev. 2014, 31:61-70. 10.1016/j.rser.2013.11.004.
5. Huang S.Y., Wang F.L., Wei W., Sun Y.H. Study on synthesis of glycerol carbonate from carbon dioxide and glycerol over base catalysts. Xiandai Huagong/Mod. Chem. Ind. 2008, 28:35-37.
6. 2(phen)/KI. Appl. Catal. A Gen. 2010, 386:188-193. 10.1016/j.apcata.2010.07.059.
7. Huntsman Corporation, Jeffsol® Glycerine Carbonate, http://www.huntsman.com/portal/page/portal/performance:products/Media%20Library/global/files/jeffsol_glycerine_carbonate.pdf.
8. Ochoa- Gómez J.R., Gómez-Jiménez-Aberasturi O., Ramírez-López C., Belsue M. A brief review on industrial alternatives for the manufacturing of glycerol carbonate, a green chemical. Org. Process Res. Dev. 2012, 16:389-399.
9. Sonnati M.O., Amigoni S., Darmanin T., Choulet O. Glycerol carbonate as a versatile building block for tomorrow: synthesis, reactivity, properties and applications. Green Chem. 2013, 15:283-306. 10.1039/c2gc36525a.
10. 2 fixation-activation agent. Chem. Eng. J. 2011, 175:505-511. 10.1016/j.cej.2011.09.081.
11. Li J., Wang T. Coupling reaction and azeotropic distillation for the synthesis of glycerol carbonate from glycerol and dimethyl carbonate. Chem. Eng. Process. 2010, 49:530-535.
12. Munshi M.K., Gade S.M., Mane M.V., Mishra D., Pal S., Vanka K. Chemical in glycerol carbonate synthesis. J. Mol. Catal. A, Chem. 2014, 391:144-149. 10.1016/j.molcata.2014.04.016.
13. J. Liu, S. Chen, C. Xia, Basic ionic liquids as efficient catalysts for the synthesis of glycerol carbonate from glycerol and ethylene carbonate, 2-3.
14. Tundo P., Selva M., Ambientali S. The chemistry of dimethyl carbonate. Acc. Chem. Res. 2002, 35:706-716.
15. Ochoa-Gómez J.R., Gómez-Jiménez-Aberasturi O., Ramírez-López C., Maestro-Madurga B. Synthesis of glycerol 1,2-carbonate by transesterification of glycerol with dimethyl carbonate using triethylamine as a facile separable homogeneous catalyst. Green Chem. 2012, 14:3368. 10.1039/c2gc35992h.
16. Gade S.M., Munshi M.K., Chherawalla B.M., Rane V.H., Kelkar A.A. Synthesis of glycidol from glycerol and dimethyl carbonate using ionic liquid as a catalyst. Catal. Commun. 2012, 27:184-188.
17. Chiappe C., Rajamani S. Synthesis of glycerol carbonate from glycerol and dimethyl carbonate in basic ionic liquids. Pure Appl. Chem. 2012, 84:755-762.
18. Lu P., Wang H., Hu K. Synthesis of glycerol carbonate from glycerol and dimethyl carbonate over the extruded CaO-based catalyst. Chem. Eng. J. 2013, 228:147-154. 10.1016/j.cej.2013.04.109.
19. Jiabo L., Wang T. On the deactivation of alkali solid catalysts for the synthesis of glycerol carbonate from glycerol and dimethyl carbonate. React. Kinet. Mech. Catal. 2011, 102:113-126.
20. Climent M.J., Corma A., De Frutos P., Iborra S., Noy M., Velty A., et al. Chemicals from biomass: synthesis of glycerol carbonate by transesterification and carbonylation with urea with hydrotalcite catalysts. The role of acid-base pairs. J. Catal. 2010, 269:140-149. 10.1016/j.jcat.2009.11.001.
21. Malyaadri M., Jagadeeswaraiah K., Sai Prasad P.S., Lingaiah N. Synthesis of glycerol carbonate by transesterification of glycerol with dimethyl carbonate over Mg/Al/Zr catalysts. Appl. Catal. A Gen. 2011, 401:153-157.
22. Teng W.K., Ngoh G.C., Yusoff R., Aroua M.K. Microwave-assisted transesterification of industrial grade crude glycerol for the production of glycerol carbonate. Chem. Eng. J. 2016, 284:469-477. 10.1016/j.cej.2015.08.108.
23. Welton T. Room-temperature ionic liquids. Solvents for synthesis and catalysis. Chem Rev. 1999, 99:2071-2084.
24. Takagaki A., Iwatani K., Nishimura S., Ebitani K. Synthesis of glycerol carbonate from glycerol and dialkyl carbonates using hydrotalcite as a reusable heterogeneous base catalyst. Green Chem. 2010, 12:578-581. 10.1039/B925404H.
25. Kumar A., Iwatani K., Nishimura S., Takagaki A., Ebitani K. Promotion effect of coexistent hydromagnesite in a highly active solid base hydrotalcite catalyst for transesterifications of glycols into cyclic carbonates. Catal. Tod. 2012, 185:241-246. 10.1016/j.cattod.2011.08.016.
26. Munshi M.K., Biradar P.S., Gade S.M., Rane V.H., Kelkar A.A. Efficient synthesis of glycerol carbonate/glycidol using 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU) based ionic liquids as catalyst. RSC Adv. 2014, 4:17124-17128. 10.1039/c3ra47433j.
27. Yi Y., Shen Y., Sun J., Wang B., Xu F., Sun R. Basic ionic liquids promoted the synthesis of glycerol 1,2-carbonate from glycerol. Chin. J. Catal. 2014, 35:757-762. 10.1016/S1872-2067(14)60036-X.
28. Zhang L., Fu X., Gao G. Anion-cation cooperative catalysis by ionic liquids. ChemCatChem 2011, 3:1359-1365. 10.1002/cctc.201100016.
29. Teng W.K., Ngoh G.C., Yusoff R., Aroua M.K. A review on the performance of glycerol carbonate production via catalytic transesterification: effects of influencing parameters. Energy Convers. Manag. 2014, 88:484-497. 10.1016/j.enconman.2014.08.036.
30. Seoud P., Silva O.E., Possidonio V., Casarano S., Arêas R., Gimenes E.P.G. Microwave-assisted derivatization of cellulose, 2-The surprising effect of the structure of ionic liquids on the dissolution and acylation of the biopolymer. Macromol. Chem. Phys. 2011, 212:2541-2550.
31. Wu K., Sasaki Y., Kazushi T., Seo K., Sakurai T. Interactions between spiropyrans and room-temperature ionic liquids: photochromism and solvatochromism. J. Phys. Chem. B 2008, 112:7530-7536.
32. Gutowski D.A.J., Holbrey K.E., Rogers J.D., Dixon R.D. Prediction of the formation and stabilities of energetic salts and ionic liquids based on ab initio electronic structure calculations. J. Phys. Chem. B 2005, 109:23196.
33. Ohno W.O.H., Yoshizawa M. Development of new class of ion conductive polymers based on ionic liquids. Electrochim. Acta 2004, 50:255-261.
34. Fukaya Y., Hayashi K., Wada M., Ohno H. Cellulose dissolution with polar ionic liquids under mild conditions: required factors for anions. Green Chem. 2008, 10:44. 10.1039/b713289a.
35. Macfarlane D.R., Pringle J.M., Johansson K.M., Forsyth A. Lewis base ionic liquids. Chem. Commun. 2006, 1905-1917. 10.1039/b516961p.
36. Zhou S., Liu L., Wang B., Xu F., Sun R. Biodiesel preparation from transesterification of glycerol trioleate catalyzed by basic ionic liquids. Chin. Chem. Lett. 2012, 23:379-382.
37. Fukaya O., Sugimoto Y., Hiroyuki A. Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formats. Biomacromolecules 2006, 7:3295-3297.
38. Crowhurst L., Mawdsley P.R., Perez-Arlandis J.M., Salter P.A., Welton T. Solvent-solute interactions in ionic liquids. Phys. Chem. Chem. Phys. 2003, 5:2790. 10.1039/b303095d.
39. Sun N., Rahman M., Qin Y., Maxim M.L., Rodríguez H., Rogers R.D. Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem. 2009, 11:646-655.
40. Swatloski R.P., Spear S.K., Holbrey J.D., Rogers R.D. Dissolution of cellulose with ionic liquids. J. Am. Chem. Soc. 2002, 124:4974-4975. doi:ja025790m [pii].
41. Xu A., Zhang Y., Lu W., Yao K., Xu H. Effect of alkyl chain length in anion on dissolution of cellulose in 1-butyl-3-methylimidazolium carboxylate ionic liquids. J. Mol. Liq. 2014, 197:211-214. 10.1016/j.molliq.2014.05.018.
42. Yadav G.D., Chandan P.A. A green process for glycerol valorization to glycerol carbonate over heterogeneous hydrotalcite catalyst. Catal. Tod. 2014, 237:47-53. 10.1016/j.cattod.2014.01.043.
43. Rokicki G., Rakoczy P., Parzuchowski P., Sobiecki M. Hyperbranched aliphatic polyethers obtained from environmentally benign monomer: glycerol carbonate. Green Chem. 2005, 7:529-539.
44. Li K.-X., Chen L., Yan Z.-C., Wang H.-L. Application of pyridinium ionic liquid as a recyclable catalyst for acid-catalyzed transesterification of Jatropha oil. Catal. Lett. 2010, 139:151-156.
45. Sik J., Stefanus F., Simanjuntaka H., Young J., Im K., Deuk S., et al. Ionic-liquid-catalyzed decarboxylation of glycerol carbonate to glycidol. J. Catal. 2013, 297:248-255. 10.1016/j.jcat.2012.10.015.
46. Mäki-Arvela P., Anugwom I., Virtanen P., Sjöholm R., Mikkola J.P. Dissolution of lignocellulosic materials and its constituents using ionic liquids-a review. Ind. Crops Prod. 2010, 32:175-201. 10.1016/j.indcrop.2010.04.005.
47. Salari H., Harifi-Mood A.R., Elahifard M.R., Gholami M.R. Solvatochromic probes absorbance behavior in mixtures of 2-hydroxy ethylammonium formate with methanol, ethylene glycol and glycerol. J. Solution Chem. 2010, 39:1509-1519. 10.1007/s10953-010-9596-8.
48. Indran V.P., Syuhada Zuhaimi N.A., Deraman M.A., Maniam G.P., Yusoff M.M., Yun Hin T.-Y., et al. An accelerated route of glycerol carbonate formation from glycerol using waste boiler ash as catalyst. RSC Adv. 2014, 4:25257-25267. 10.1039/C4RA02910K.
49. Hazimah A.H., Ooi T.L., Salmiah A. Recovery of glycerol and diglycerol from glycerol pitch. J. Oil Palm Res. 2003, 15:1-5.
50. Calvino-Casilda V., Mul G., Fernández J.F., Rubio-Marcos F., Bañares M.A. Monitoring the catalytic synthesis of glycerol carbonate by real-time attenuated total reflection FTIR spectroscopy. Appl. Catal. A Gen. 2011, 409-410:106-112. 10.1016/j.apcata.2011.09.036.
51. Ochoa-Gómez J.R., Gómez-Jiménez-Aberasturi O., Maestro-Madurga B., Pesquera-Rodríguez A., Ramírez-López C., Lorenzo-Ibarreta L., et al. Synthesis of glycerol carbonate from glycerol and dimethyl carbonate by transesterification: catalyst screening and reaction optimization. Appl. Catal. A Gen. 2009, 366:315-324. 10.1016/j.apcata.2009.07.020.
52. Fischer J., Ritter H. Oligomeric epoxide-amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: solubility in presence of cyclodextrin and curing properties. Beilstein J. Org. Chem. 2013, 9:2803-2811.
53. Zhou Y., Ouyang F., Song Z.-B., Yang Z., Tao D.-J. Facile one-pot synthesis of glycidol from glycerol and dimethyl carbonate catalyzed by tetraethylammonium amino acid ionic liquids. Catal. Commun. 2015, 66:25-29. 10.1016/j.catcom.2015.03.011.
54. Grey R.A., Pa W.C. Preparation of cyclic carbonates using alkylammonium and tertiary amine catalysts 1999.