Reaction kinetics of glycerol acetal formation via transacetalization with 1,1-diethoxyethane

Chemical Engineering Journal

Volumn 222, Issue , 2013, Pages 374-381

  Hong, Xi ^a   McGiveron, Omar ^a   Kolah, Aspi K ^a   Orjuela, Alvaro ^b   Peereboom, Lars ^a   Lira, Carl T ^a   Miller, Dennis J ^a  

^a Michigan State University   (United States)

^b UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

1,1 Diethoxyethane; Acetals; Glycerol; Kinetics; Transacetalization

Indexed keywords

1,1-DIETHOXYETHANE; ACETALS; CATIONIC EXCHANGE RESINS; REACTANT CONVERSION; REACTION CONDITIONS; REVERSE REACTIONS; SECOND ORDER KINETICS; TRANSACETALIZATION;

ACTIVATION ENERGY; BYPRODUCTS; ENZYME KINETICS; EQUILIBRIUM CONSTANTS; KINETICS; RATE CONSTANTS;

GLYCEROL;

EID: 84875304266     PISSN: 13858947     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cej.2013.02.023     Document Type: Article

References (30)

1. Tang S., Boehme H., Lam H., Zhang Z. Pichia pastoris fermentation for phytase production using crude glycerol from biodiesel production as the sole carbon source. Biochem. Eng. J. 2009, 43:157-162.
2. Fernando S., Adhikari S., Kota K., Bandi Z. Glycerol based automotive fuels from future biorefineries. Fuel 2007, 86:2806-2809.
3. da Silva C.X.A., Gonçalves V.L.C., Mota C.J.A. Water-tolerant zeolite catalyst for the acetalisation of glycerol. Green Chem. 2009, 11:38-41.
4. Zhou C.H., Beltramini N.J., Fan Y.X., Lu G.Q. Chemoselective catalytic conversion of glycerol as a biorenewable source to valuable commodity chemicals. Chem. Soc. Rev. 2008, 37:527-549.
5. H. Noureddini, Process for producing biodiesel fuel with reduced viscosity and a cloud point below thirty-two (32) degrees Fahrenheit, US Patent 6015440, 2001.
6. G.A. Olah, Cleaner burning and cetane enhancing diesel fuel supplements, US Patent 5520710, 1995.
7. B. Delfort, I. Durand, A. Jaecker, T. Lacome, X. Motagne, F. Paille, Diesel fuel compounds containing glycerol acetals, US Patent 6890364, 2005.
8. B. Delfort, I. Durand, A. Jaecker, T. Lacome, X. Motagne, F. Paille, Diesel fuel compounds contain glycerol acetal carbonates, US Patent 7097674, 2006.
9. J. Delgado Puche, Procedure to obtain biodiesel fuel with improved properties at low temperature, US Patent Application 20030167681, 2003.
10. Silva P., Goncalves V., Mota C. Glycerol acetals as anti-freezing additives for biodiesel. Bioresource Technol. 2010, 101:6225-6229.
11. Melero J.A., Van Grieken R., Morales G., Paniagua M. Acidic mesoporous silica for the acetylation of glycerol: synthesis of bioadditives to petrol fuel. Energy Fuels 2007, 21:1782-1791.
12. Garcia E., Laca M., Perez E., Garrido A., Peinado J. New class of acetal derived from glycerin as a biodiesel fuel component. Energy Fuels 2008, 22:4274-4280.
13. Hill H.S., Hibbert H. Studies on reactions relating to carbohydrates and polysaccharides. VI. Relative ease of formation of five- and six-membered heterocyclic carbon-oxygen configurations. J. Am. Chem. Soc. 1923, 45:3117-3124.
14. Aksnes G., Albriktsen P., Juvvik P. Studies of cyclic acetal and ketal isomers of glycerol. Acta. Chem. Scand. 1965, 19:920-930.
15. B. Bruchmann, K. Haberle, H. Gruner, M. Hirn, Preparation of cyclic acetals or ketals, US Patent 5917059, 1999.
16. Camara J.S., Marques J.C., Alves A., Silva Ferreira A.C. Heterocyclic acetals in Madeira wines. Anal. Bioanal. Chem. 2003, 375:1221-1224.
17. Silva Ferreira A.C., Barbe J.C., Bertrand A. Heterocyclic acetals from glycerol and acetaldehyde in port wines: evolution with aging. J. Agric. Food Chem. 2002, 50:2560-2564.
18. Deutsch J., Martin A., Lieske H. Investigations on heterogeneously catalysed condensations of glycerol to cyclic acetals. J. Catal. 2007, 245:428-435.
19. Agirre I., Garcia I., Requies J., Barrio V., Guemez M., Cambra J., Arias P. Glycerol acetals, kinetic study of the reaction between glycerol and formaldehyde. Biomass Bioenergy 2011, 35:3636-3642.
20. X. Hong, A. Kolah, O. McGiveron, C. Lira, D. Miller, An Improved Approach to Make Cyclic Acetals from Glycerol, in: Proc. AIChE Annual Meeting, 2009, Nov 8-13, Nashville, Tennessee, USA.
21. Piantadosi C., Anderson C.E., Brecht E.A., Yarbro C.L. The preparation of cyclic acetals by transacetalation. J. Am. Chem. Soc. 1958, 80:6613-6617.
22. Hasabnis A., Mahajani S. Transacetalization of glycerol with methylal by reactive distillation. Ind. Eng. Chem. Res. 2012, 51:13021-13036.
23. Du J., Peng Y., Ding Y. Synthesis and characterization of polymer networks based on two kinds of macromonomer. Colloid Polym. Sci. 2003, 281:90-95.
24. Cintrat J.C., Leat-Crest V., Parrain J.L., Le Grognec E., Beaudet I., Quintard J.P. Preparation of chiral 2-stannyloxazolidines and first considerations on the transacetalization reaction mechanism. Eur. J. Org. Chem. 2004, 20:4251-4267.
25. D.J. Miller, L. Peereboom, A. Kolah, N. Asthana, C.T. Lira, Process for production of a composition useful as a fuel, US Patent 7321052, 2008.
26. Freedman B., Buttfield R.O., Pryde E.H. Transesterification of soybean oil. J. Am. Oil Chem. Soc. 1986, 63:1375-1380.
27. Solomons G.T.W. Fundamentals of Organic Chemistry 1994, J Wiley & Sons, New York. fourth ed.
28. Dakka J., Goris H. Clean process for propanal oxidation to lactic acid. Catal. Today 2006, 117:265-270.
29. Shostakovsky M., Zhebrovsky V., Medelyanovskaya M. Reactions between vinyl compounds and multifunctional compounds, communication 1. Reactions of alkyl vinyl ethers with glycerol. Russ. Chem. Bull. 1954, 3:137-141.
30. Smith J.M. Chemical Engineering Kinetics 1981, McGraw-Hill, New York. third ed.