Esterification of palmitic acid with epichlorohydrin on anion exchange resin catalyst

• Authors: Emil Muresan , Spiridon Oprea , Theodor Malutan , Mihai Vata
• Languages of publication: EN

Abstracts

EN

The esterification reaction of palmitic acid with epichlorohydrin catalyzed by an anionic macroporous resin was studied. Purolite A-500 resin proved to be a very effective catalyst in the synthesis of 3-chloro-2-hydroxypropyl palmitate. The effects of certain parameters such as speed of agitation, catalyst particle size, catalyst loading, temperature, initial molar ratio between reactants on the rate of reaction were studied. It was found that the overall rate is intrinsically kinetically controlled. The structure of synthesized ester was confirmed by FTIR and 1H NMR analyses. [...]

Keywords

EN

Palmitic acid; epichlorohydrin; esterification; kinetics; ion exchange resins

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2007
• Volume: 5
• Issue: 3
• Pages: 715-726

Dates

published

1 - 9 - 2007

online

1 - 9 - 2007

Contributors

author

Emil Muresan

• Departament of Organical and Biochemical Engineering, The Faculty of Chemical Engineering at the “Gh. Asachi” Technical University of Iassy, D. Mangeron street, 71A, Iasi, 700050, Romania

author

Spiridon Oprea

• Departament of Organical and Biochemical Engineering, The Faculty of Chemical Engineering at the “Gh. Asachi” Technical University of Iassy, D. Mangeron street, 71A, Iasi, 700050, Romania

author

Theodor Malutan

• Departament of Natural and Synthetic Polymers, The Faculty of Chemical Engineering at the “Gh. Asachi” Technical University of Iassy, D. Mangeron street, 71A, Iasi, 700050, Romania

author

Mihai Vata

• Departament of Natural and Synthetic Polymers, The Faculty of Chemical Engineering at the “Gh. Asachi” Technical University of Iassy, D. Mangeron street, 71A, Iasi, 700050, Romania

References

• [1] M. Nurbas, Z.H. Asadov, A.D. Aga-Zade, S. Kabasakal, G. Ahmadova and M.B. Zenouzi: “Surfactants based on higher carboxylic acids and epoxy compounds”, Iran. Polym. J., Vol. 14, (2005), pp. 317–322.
• [2] R. Janis, A. Klasek and J. Bobalova: “Chromium (III) acetate hydroxide - an efficient catalyst for preparation of 1-monoacylglycerols by the glycidol - fatty acid reaction”, J. Food Lipids, Vol. 13, (2006), pp. 199–209. http://dx.doi.org/10.1111/j.1745-4522.2006.00045.x[Crossref]
• [3] M. Yamada: “Functional esters derived from fats and oils”, J. Oil Palm. Res., Special issue, (2006), pp. 50–57.
• [4] V. Usachov and E.N. Shved: “Acidolysis of epichlorohydrin by acetic acid in the presence of tetraethylammonium bromide”, Mendeleev Commun., Vol. 12, (2002), pp. 113–114. http://dx.doi.org/10.1070/MC2002v012n03ABEH001586[Crossref]
• [5] M. Kucharski and E. Chmiel-Szukiewicz: “Reactions of trithiocyanuric acid with oxiranes.III.Reactions with epichlorohydrin”, J. Appl. Polym. Sci., Vol. 10, (2002), pp. 1154–1160. http://dx.doi.org/10.1002/app.10648[Crossref]
• [6] A. Bukowska, A.K. Guskov, M.G. Makarov, E. Rokaszewski and V.F. Svets: “Kinetics of addition of acetic acid to epichlorohydrin in the presence of DMF or DMSO”, J. Chem. Technol. Biot., Vol. 63, (1995), pp. 379–383. http://dx.doi.org/10.1002/jctb.280630412[Crossref]
• [7] A. Bukowska, A.K. Guskov, M.G. Makarov, E. Rokaszewski and V.F. Svets: “Kinetics of addition of acetic acid to epichlorohydrin in the presence of alkali metal acetates”, J. Chem. Technol. Biot., Vol. 63, (1995), pp. 374–378. http://dx.doi.org/10.1002/jctb.280630411[Crossref]
• [8] A. Bukowska and W. Bukowski: “Kinetics of acetic acid addition to epichlorohydrin in the presence of chromium acetate and chromic anhydride”, J. Chem. Technol. Biot., Vol. 67, (1996), pp. 176–182. http://dx.doi.org/10.1002/(SICI)1097-4660(199610)67:2<176::AID-JCTB549>3.0.CO;2-V[Crossref]
• [9] A. Bukowska and W. Bukowski: “A highly regioselective catalyst of epichlorohydrin acidolysis”, J. Chem. Technol. Biot., Vol. 73, (1998), pp. 341–344. http://dx.doi.org/10.1002/(SICI)1097-4660(199812)73:4<341::AID-JCTB960>3.0.CO;2-6[Crossref]
• [10] A. Bukowska and W. Bukowski: “Kinetics of addition of acrylic and metacrylic acids to epichlorohydrin in the presence of chromium (III) ethanoate”, J. Chem. Technol. Biot., Vol. 74, (1999), pp. 675–678. http://dx.doi.org/10.1002/(SICI)1097-4660(199907)74:7<675::AID-JCTB104>3.0.CO;2-O[Crossref]
• [11] W. Bukowski: “The solvents effects in the reactions of carboxylic acids with oxiranes. 1. Kinetics of the reaction of acetic acid with epichlorohydrin in butan-1-ol”, Int. J. Chem. Kinet., Vol. 32, (2000), pp. 378–387. http://dx.doi.org/10.1002/(SICI)1097-4601(2000)32:6<378::AID-KIN4>3.0.CO;2-3[Crossref]
• [12] A. Bukowska and W. Bukowski: “The effect of reaction product on the rate of addition of acetic acid to epichlorohydrin in the presence of chromium (III) acetate”, J. Chem. Technol. Biot., Vol. 76, (2001), pp. 966–970. http://dx.doi.org/10.1002/jctb.469[Crossref]
• [13] A. Bukowska, W. Bukowski and J. Noworol: “A study on the addition of some carboxylic acids to epichlorohydrin in the presence of salen chromium (III) complexes”, J. Mol. Catal. A: Chemical, Vol. 203, (2003), pp. 95–99. http://dx.doi.org/10.1016/S1381-1169(03)00405-9[Crossref]
• [14] A. Bukowska and W. Bukowski: “Kinetic study of addition of some carboxylic acids to 1,2-epoxy-3-phenoxypropane”, Org. Process Res. Dev., Vol. 3, (1999), pp. 432–436. http://dx.doi.org/10.1021/op9900479[Crossref]
• [15] W. Bukowski: “The effect of diglyme on the kinetics of chromium (III) ethanoate-catalysed reactions of carboxylic acids with epichlorohydrin”, Org. Process Res. Dev., Vol. 6, (2002), pp. 10–14. http://dx.doi.org/10.1021/op010057l[Crossref]
• [16] R.A. Kozlovskii, M.G. Makarov, V.F. Shvets and N.A. Maksimova: “Kinetics of the acetic acid oxyethylation catalysed by chromium acetate”, Kinet. Catal, Vol. 41, (2000), pp. 737–742. http://dx.doi.org/10.1023/A:1026652515224[Crossref]
• [17] G.D. Yadav and M.S.M.M. Rahuman: “Activities of clays and ion exchange resins in the synthesis of phthalate esters”, Clean Technol. Environ Policy, Vol. 6, (2004), pp. 114–119. http://dx.doi.org/10.1007/s10098-003-0217-8[Crossref]
• [18] G.D. Yadav and M.B. Thathagar: “Esterification of maleic acid with ethanol over cation-exchange resin catalysts”, React. Funct. Polym., Vol. 52, (2002), pp.99–110. http://dx.doi.org/10.1016/S1381-5148(02)00086-X[Crossref]
• [19] G.D. Yadav and M.S.M.M. Rahuman: “Synthesis of fragrance and flavour grade esters: activities of different ion exchange resins and kinetic studies”, Clean. Technol. Environ. Policy, Vol. 5, (2003), pp. 128–135. http://dx.doi.org/10.1007/s10098-003-0196-9[Crossref]
• [20] G.D. Yadav and P.K. Goel: “Selective synthesis of perfumery grade cyclohexyl esters from cyclohexene and carboxylic acids over ion exchange resins: an example of 100% economy”, Green. Chem., Vol. 2, (2000), pp. 71–77. http://dx.doi.org/10.1039/a908035j[Crossref]
• [21] G.D. Yadav and M.S. Krishnan: “An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol”, Org. Process Res. Dev., Vol. 2, (1998), pp. 86–95. http://dx.doi.org/10.1021/op970047d[Crossref]
• [22] P.S. Belov, N.S. Baraj and C.D. Korenev: “Study of the reaction of carboxylic acid with epichlorohydrin in the presence of the anion exchanger AV-17 as a catalyst”, Izvestia VUZ-ov, Khimia i Khim. Technol., Vol. 26, (1983), pp. 668–672.
• [23] V.A. Podgornova, N.F. Orehova, B.F. Ustavshchikov, V.D. Koryolova, V.B. Kargman and N.B. Galitskaya: “Use of anion exchange resin for synthesis of hydroxyalkyl esters of unsaturated acids”, Osnov Org.Sintez Neftekhim., Vol. 2, (1975), pp. 89–92.
• [24] E. Dumitriu, S. Oprea, M. Dima and S. Avramescu: “Catalysis by polymers. III. Synthesis of 3-chloro-2-hydroxypropyl acrylate on exchange resins”, Rev. Chim. (Bucharest), Vol. 32, (1981), pp. 225–229.
• [25] R. Jay: “Direct titration of epoxy compounds and azirides”, Anal. Chem., Vol. 36, (1964), pp. 667–668. http://dx.doi.org/10.1021/ac60209a037[Crossref]
• [26] A. Chakrabarti and M.M. Sharma: “Cationic exchange resins as catalyst”, React. Polym, Vol. 20, (1993), pp. 1–45. http://dx.doi.org/10.1016/0923-1137(93)90064-M[Crossref]

Identifiers

DOI

10.2478/s11532-007-0033-9