PL EN


Preferences help
enabled [disable] Abstract
Number of results
2013 | 15 | 3 | 42-47
Article title

Esterification of fatty acids with C8-C9 alcohols over selected sulfonic heterogeneous catalysts

Content
Title variants
Languages of publication
EN
Abstracts
EN
A study on the synthesis of esters of fatty acids of natural origin (oleic acid from rapeseed oil) and branched synthetic isostearic acid with commercially available alcohols C8-C9 i.e. 2-ethylhexanol (2-EH) and 3,5,5-trimethylhexanol (TMH) in the presence of selected heterogeneous catalysts containing active sulfonic groups has been made. The catalysts were obtained using ready available amorphous silicas with different textural characteristics. The influence of catalyst porosity on the catalytic properties in the esterification of fatty acids has been investigated. The effect of the synthesis temperature has also been studied. The results were compared with the results of esterification with the use of acidic ion exchange resins. It was shown that catalysts obtained on the basis of amorphous silicas are good and reusable catalysts for the esterification of fatty acids with higher alcohols
Publisher
Year
Volume
15
Issue
3
Pages
42-47
Physical description
Dates
published
1 - 09 - 2013
online
20 - 09 - 2013
References
  • 1. Hoydonckx, H.E., De Vos, D.E., Charan, S.A. & Jacobs, P.A. (2004) Esterification and transesterification of renewable chemicals. Topics in Catal. 27, 83-96. DOI: 10.1023/B:TOCA.0000013543.96438.1a.[Crossref]
  • 2. Sanchez, N., Martinez, M., Aracil, J. & Corma, A. (1992) Synthesis of oleyl oleate as a jojoba oil analog. J. Am. Oil Chem. Soc. 69, 1150-1153. DOI: 10.1007/BF02541053.[Crossref]
  • 3. Meffert, A. (1984) Technical uses of fatty acid esters. J. Am. Oil Chem. Soc. 61, 255-258.
  • 4. Mantri, K., Komura, K. & Sugi, Y. (2005) ZrOCl2·8H2O Catalysts for the esterification of long chain aliphatic carboxylic acids and alcohols. Green Chem. 7, 677-682. DOI: 10.1039/ B504369G.[Crossref]
  • 5. Laudami, C.G., Habulin, C.M., Primo, M., Knez, C.Z. & Porta, G.D. (2006) Optimisation of n-octyl oleate enzymatic synthesis over Rhizomucor miehei lipase. Bioprocess Biosyst. Eng. 29, 119-127. DOI: 10.1007/s00449-006-0061-4.[Crossref]
  • 6. Rocha, J.S.M., Gil, M.H. & Garcia, F.A.B. (1999) Optimisation of the enzymatic synthesis of n-octyl oleate with immobilised lipase in the absence of solvents. J. Chem. Tech. Biotechnol. 74, 607-612, DOI: 10.1002/(SICI)1097-4660.[Crossref]
  • 7. Kale, V., Subbarao, R., Lakshminarayana, G. & Bhagwant Rao, M. (1991). Studies on kinetics and preparation of C36 dimer acid esters. J. Am. Oil Chem. Soc. 68, 583-584. DOI: 10.1007/BF02660156.[Crossref]
  • 8. Kai, Y. & Pryde, E.H. (1982) Production of branched- -chain fatty acids from sterculia oil. J. Am. Oil Chem. Soc. 59, 300-305. DOI: 10.1007/BF02662231.[Crossref]
  • 9. Erdem-Senatalar, A., Erencek, E., Töter, M. & Erciyes, A.T. (1994) Effects of Lewis acid catalysts on the esterification kinetics of castor oil with oleic acid. J Am. Oil Chem. Soc. 71, 1035-1037. DOI: 10.1007/BF02542275.[Crossref]
  • 10. Lacaze-Dufaure, C. & Mouloungui, Z. (2000) Catalysed or uncatalysed esterification reaction of oleic acid with 2-ethylhexanol. Appl. Catal. A 204, 223-227. DOI: 10.1016/ S0926-860X(00)00533-0.[Crossref]
  • 11. Vieville, C., Mouloungui, Z. & Gaset, A. (1993) Esterification of oleic acid by methanol c.atalysed by p-toluenesulfonic acid and the cation-exchange resins K2411 and K1481 in supercritical carbon dioxide Ind. Eng. Chem. Res. 32, 2065-2068. DOI: 10.1021/ie00021a031.[Crossref]
  • 12. Corma, A., Garcia, H., Iborra, S. & Primo, J. (1989). Modified faujasite zeolites as catalysts in organic reactions: Esterification of carboxylic acids in the presence of HY zeolites. J. Catal. 120, 78-87. DOI: 10.1016/0021-9517(89)90252-2.[Crossref]
  • 13. Marquez-Alvarez, C., Sastre, E. & Perez-Pariente, J. (2004). Esterification and transesterification of renewable chemicals. Topics in Catal. 27, 105-117. DOI: 10.1023/B:TOCA.0000013545.81809.bd.[Crossref]
  • 14. Van Rhijn, W., DeVos, D.E., Sels, B.F., Bossaert, W.D. & Jacobs, P.A. (1998). Sulfonic acid functionalised ordered mesoporous materials as catalysts for condensation and esterification reactions. Chem. Commun. 3, 317-318. DOI: 10.1039/A707462J.[Crossref]
  • 15. Bossaert, W.D., DeVos, D.E., Van Rhijn, W., Bullen, J., Grobet, P.J. & Jacobs, P.A. (1999) Mesoporous sulfonic acids as selective heterogeneous catalysts for the synthesis of monoglycerides. J. Catal. 182, 156-164. DOI: 10.1006/jcat.1998.2353.[Crossref]
  • 16. Diaz, L., Mohino, F., Perez-Pariente, J. & Sastre, E. (2001). Synthesis, characterization and catalytic activity of MCM-41-type mesoporous silicas functionalized with sulfonic acid. Appl. Catal. A 205, 19-30. DOI: 10.1016/S0926-860X(00)00808-5.[Crossref]
  • 17. Diaz, L., Mohino, F., Perez-Pariente, J. & Sastre, E. (2003). Synthesis of MCM-41 materials functionalised with dialkylsilane groups and their catalytic activity in the esterification of glycerol with fatty acids. Appl. Catal. A 242, 161-169. DOI: 10.1016/S0926-860X(02)00501-X.[Crossref]
  • 18. Perez-Pariente, J., Diaz, L., Mohino, F. & Sastre, E. (2003). Selective synthesis of fatty monoglycerides by using functionalised mesoporous catalysts. Appl. Catal. A 254, 173-188. DOI: 10.1016/S0926-860X(03)00481-2.[Crossref]
  • 19. Diaz, L., Mohino, F., Blasco, T., Sastre, E., Perez-Pariente, J. (2005) Influence of the alkyl chain length of HSO3-R-MCM-41 on the esterification of glycerol with fatty acids. Micropor. Mesopor. Mat. 80, 33-42. DOI: 10.1016/j.micromeso.2004.11.011.[Crossref]
  • 20. Hermida, L., Abdullah, A.Z. & Mohamed, A.H. (2010). Post synthetically functionalized SBA-15 with organosulfonic acid and sulfated zirconia for esterification of glycerol to monoglyceride. J. Appl. Sci. 10, 3199-3206. DOI: 10.3923/ jas.2010.3199.3206.[Crossref]
  • 21. Mrowiec-Białoń, J., Maresz, K., Malinowski, J.L. & Jastrzebski, A.B. (2008). Organosulfonic acid functionalised silica mesostructured cellular foams - efficient acidic catalysts for reaction of esterification. Chem. Proc. Eng. 29, 701-711.
  • 22. Bugrayev, A., Al-Haq, N., Okopie, R.A., Qazi, A., Suggate, M., Sullivan, A.C. & Wilson, J.R.H. (2008). Covalently linked ethylmercaptophenyl sulfonic acid and ethylmercaptobenzyl sulfonic acid silica materials-Synthesis and catalytic activity. J. Mol. Catal. A 280, 96-101. DOI: 10.1016/j.molcata.2007.10.026.[WoS][Crossref]
  • 23. Karimi, B. & Khalkhali, M. (2007). Silica functionalized sulfonic acid as a recyclable interphase catalyst for chemoselective thioacetalization of carbonyl compounds in water. J. Mol. Catal. A 271, 75-79. DOI: 10.1016/j.molcata.2007.02.018.[WoS][Crossref]
  • 24. Gupta, R., Paul, S. & Gupta, R. (2007). Covalently anchored sulfonic acid onto silica as efficient and recoverable interphase catalyst for the synthesis of 3.4-dihydropyrimidinones/ thiones. J. Mol. Catal. A 266, 50-54. DOI: 10.1016/j. molcata.2006.10.039.[WoS][Crossref]
Document Type
Publication order reference
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_pjct-2013-0042
Identifiers
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.