Glycerol ethers synthesis from glycerol etherification with tert-butyl alcohol in reactive distillation

Computers and Chemical Engineering

Volumn 35, Issue 10, 2011, Pages 2034-2043

  Kiatkittipong, Worapon ^a   Intaracharoen, Parinya ^a   Laosiripojana, Navadol ^b   Chaisuk, Choowong ^a   Praserthdam, Piyasan ^c   Assabumrungrat, Suttichai ^c  

^a SILPAKORN UNIVERSITY   (Thailand)

^b KING MONGKUT'S UNIVERSITY OF TECHNOLOGY THONBURI   (Thailand)

^c CHULALONGKORN UNIVERSITY   (Thailand)

Author keywords

Equilibrium conversion; Etherification; Group contribution; Kinetic; Reactive distillation; Tert butyl ether of glycerol

Indexed keywords

EQUILIBRIUM CONVERSION; ETHERIFICATION; GROUP CONTRIBUTION; REACTIVE DISTILLATIONS; TERT-BUTYL ETHERS;

AUTOCLAVES; CATALYST ACTIVITY; CHEMICAL REACTORS; COMPUTER SIMULATION; DISTILLATION; GLYCEROL; KINETICS; ORGANIC COMPOUNDS; REACTION RATES; SYNTHESIS (CHEMICAL); THERMOANALYSIS;

ETHERS;

EID: 79960556164     PISSN: 00981354     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.compchemeng.2011.01.016     Document Type: Article

References (48)

1. Abella L.C., Gaspillo P.A.D., Maeda M., Goto S. Kinetic study on the dehydration of tert-butyl alcohol catalyzed by ion exchange resins. International Journal of Chemical Kinetics 1999, 31:854-859.
2. Aiouache F., Goto S. Kinetic study on 2-methyl-1-butanol dehydration catalysed by ion exchange resin. Journal of Chemical Engineering of Japan 2002, 35:436-442.
3. Aiouache F., Goto S. Sorption effect on kinetics of etherification of tert-amyl alcohol and ethanol. Chemical Engineering Science 2003, 58:2065-2077.
4. Arellano-Garcia H., Carmona I., Wozny G. A new operation mode for reactive batch distillation in middle-vessel columns: Start-up and operation. Computers & Chemical Engineering 2008, 32:161-169.
5. Aspen Plus Version Aspen Technology, Inc. 2006, Cambridge, Massachusetts, USA.
6. Assabumrungrat S., Kiatkittipong W., Sevitoon N., Praserthdam P., Goto S. Kinetics of liquid phase synthesis of ethyl tert-butyl ether from tert-butyl alcohol and ethanol catalyzed by β-zeolite supported on monolith. International Journal of Chemical Kinetics 2002, 34:292-299.
7. Assabumrungrat S., Wongwattanasate D., Pavarajarn V., Praserthdam P., Arpornwichanop A., Goto S. Production of ethyl tert-butyl ether from tert-butyl alcohol and ethanol catalyzed by β-zeolite in reactive distillation. Korean Journal of Chemical Engineering 2004, 21:1139-1146.
8. Benson S.W. Thermochemical Kinetics 1976, John Wiley and Sons, New York. 2nd ed.
9. Benson S.W., Buss J.H. Additivity rules for the estimation of molecular properties thermodynamic properties. The Journal of Chemical Physics 1958, 29:546-572.
10. Bhatia S., Mohamed A.R., Ahmad A.L., Chin S.Y. Production of isopropyl palmitate in a catalytic distillation column: Comparison between experimental and simulation studies. Computers & Chemical Engineering 2007, 31:1187-1198.
11. Carlos Cárdenas-Guerra J., López-Arenas T., Lobo-Oehmichen R., Pérez-Cisneros E.S. A reactive distillation process for deep hydrodesulfurization of diesel: Multiplicity and operation aspects. Computers & Chemical Engineering 2010, 34:196-209.
12. Constantinou L., Gani R. New group contribution method for estimating properties of pure compounds. AIChE Journal 1994, 40:1697-1710.
13. David, L., & Calef, B. (1940). Fuel for compression ignition engines. United States patent US 2221839. Philadelphia: The Atlantic Refinning Company.
14. Dhale A.D., Myrant L.K., Chopade S.P., Jackson J.E., Miller D.J. Propylene glycol and ethylene glycol recovery from aqueous solution via reactive distillation. Chemical Engineering Science 2004, 59:2881-2890.
15. Gani R., Jepsen T.S., Pérez-Cisneros E.S. A generalized reactive separation unit model modelling and simulation aspects. Computers & Chemical Engineering 1998, 22(Suppl.):S363-S370.
16. Gelosa D., Ramaioli M., Valente G., Morbidelli M. Chromatographic reactors: Esterification of glycerol with acetic acid using acidic polymeric resins. Industrial & Engineering Chemistry Research 2003, 42:6536-6544.
17. Georgiadis M.C., Schenk M., Pistikopoulos E.N., Gani R. The interactions of design control and operability in reactive distillation systems. Computers & Chemical Engineering 2002, 26:735-746.
18. Gonzalez J.C., Fair J.R. Preparation of tertiary amyl alcohol in a reactive distillation column 1. Reaction kinetics, chemical equilibrium, and mass-transfer issues. Industrial & Engineering Chemistry Research 1997, 36:3833-3844.
19. Honkela M.L., Ouni T., Krause A.O.I. Thermodynamics and kinetics of the dehydration of tert-butyl alcohol. Industrial & Engineering Chemistry Research 2004, 43:4060-4065.
20. Joback K.G., Reid R.C. Estimation of pure-component properties from group contributions. Chemical Engineering Communications 1987, 57:233-243.
21. Johnson D.T., Taconi K.A. The glycerin glut: Options for the value-added conversion of crude glycerol resulting from biodiesel production. Environmental Progress 2007, 26:338-348.
22. Kang J.W., Abildskov J., Gani R., Cobas J. Estimation of mixture properties from first- and second-order group contributions with the UNIFAC model. Industrial & Engineering Chemistry Research 2002, 41:3260-3273.
23. Karinen R.S., Krause A.O.I. New biocomponents from glycerol. Applied Catalysis A: General 2006, 306:128-133.
24. Kiatkittipong W., Assabumrungrat S., Praserthdam P., Goto S. A pervaporation membrane reactor for liquid phase synthesis of ethyl tert-butyl ether from tert-butyl alcohol and ethanol. Journal of Chemical Engineering of Japan 2002, 35:547-556.
25. Kiatkittipong W., Thipsunet P., Goto S., Chaisuk C., Praserthdam, Assabumrungrat S. Simultaneous enhancement of ethanol supplement in gasoline and its quality improvement. Fuel Processing Technology 2008, 89:1365-1370.
26. Kiatkittipong W., Yoothongkham K., Chaisuk C., Praserthdam P., Goto S., Assabumrungrat S. Self-etherification process for cleaner fuel production. Catalysis Letters 2009, 128(1-2):154-163.
27. Kiatkittipong W., Suwanmanee S., Laosiripojana N., Praserthdam P., Assabumrungrat S. Cleaner gasoline production by using glycerol as fuel extender. Fuel Processing Technology 2010, 91:456-460.
28. Klepacova K., Mravec D., Bajus M. tert-Butylation of glycerol catalysed by ion-exchange resins. Applied Catalysis A: General 2005, 294:141-147.
29. Klepacova K., Mravec D., Bajus M. Etherification of glycerol with tert-butyl alcohol catalysed by ion-exchange resins. Chemical Papers 2006, 60:224-230.
30. Klepacova K., Mravec D., Kaszonyi A., Bajus M. Etherification of glycerol and ethylene glycol by isobutylene. Applied Catalysis A: General 2007, 328:1-13.
31. Klincewicz K.M., Reid R.C. Estimation of critical properties with group contribution methods. AIChE Journal 1984, 30:137-142.
32. Koukkari P., Pajarre R. Calculation of constrained equilibria by Gibbs energy minimization. Calphad 2006, 30:18-26.
33. Marrero J., Gani R. Group-contribution based estimation of pure component properties. Fluid Phase Equilibria 2001, 183-184:183-208.
34. Melero J.A., Vicente G., Morales G., Paniagua M., Moreno J.M., Roldán R., et al. Acid-catalyzed etherification of bio-glycerol and isobutylene over sulfonic mesostructured silicas. Applied Catalysis A: General 2008, 346:44-51.
35. Morgan, W. D. (2008). Methods for producing triol ethers by reactive distillation. United States patent US 20080228011. Houston, TX: Endicott Biofuels II, LLC.
36. Olah, G. A. (1996). Cleaner burning and cetane enhancing diesel fuel supplements. United States patent US 5520710. Beverly Hills, Calif: George A. Olah.
37. Ozbay N., Oktar N., Dogu G., Dogu T. Conversion of biodiesel by-product glycerol to fuel ethers over different solid acid catalysts. International Journal of Chemical Reactor Engineering 2010, 8:A18.
38. Pairojpiriyakul T., Kiatkittipong W., Arpornwichanop A., Soottitantawat A., Wiyaratn W., Laosiripojana N., et al. Effect of operation modes on hydrogen production from glycerol at energy self-sufficient conditions: Thermodynamic analysis. International Journal of Hydrogen Energy 2010, 35:10257-10270.
39. Pereira C.S.M., Pinho S.P., Silva V.M.T.M., Rodrigues A.E. Thermodynamic equilibrium and reaction kinetics for the esterification of lactic acid with ethanol catalyzed by acid ion-exchange resin. Industrial & Engineering Chemistry Research 2008, 47:1453-1463.
40. Poling B.E., Prausnitz J.M., O'Connell J.P. Properties of gases and liquids 2001, McGraw-Hill. 5th ed.
41. Popken T., Gotze L., Gmehling J. Reaction kinetics and chemical equilibrium of homogeneously and heterogeneously catalyzed acetic acid esterification with methanol and methyl acetate hydrolysis. Industrial & Engineering Chemistry Research 2000, 39:2601-2611.
42. Quitain A., Itoh H., Goto S. Reactive distillation for synthesizing ethyl tert-butyl ether from bioethanol. Journal of Chemical Engineering of Japan 1999, 32:280-287.
43. Ramzan N., Faheem M., Gani R., Witt W. Multiple steady states detection in a packed-bed reactive distillation column using bifurcation analysis. Computers & Chemical Engineering 2010, 34:460-466.
44. Rihko L.K., Krause A.O.I. Etherification of FCC light gasoline with methanol. Industrial & Engineering Chemistry Research 1996, 35:2500-2507.
45. Steinigeweg S., Gmehling J. Esterification of a fatty acid by reactive distillation. Industrial & Engineering Chemistry Research 2003, 42:3612-3619.
46. Vadapalli A., Seader J.D. A generalized framework for computing bifurcation diagrams using process simulation programs. Computers & Chemical Engineering 2001, 25:445-464.
47. Yin X., Yang B., Goto S. Kinetics of liquid-phase synthesis of ethyl tert-butyl ether from tert-butyl alcohol and ethanol catalyzed by ion exchange resin and heteropoly acid. International Journal of Chemical Kinetics 1995, 27:1065-1074.
48. Zhou C.-H.C., Beltramini J.N., Fan Y.-X., Lu G.Q.M. Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chemical Society Reviews 2008, 37:527-549.