Abdul Razak, Che Nyonya

Basri, Mahiran

Salleh, Abu Bakar

Universiti Putra Malaysia Institutional Repository

Chemical SciencesEnzymatic Synthesis of Surfactant-like CompoundsAbu Bakar 5alleh, Mahiran 6asri, Che Nyonya A. RazakFaculty Science and Environmental StudiesUniversiti Putra Malaysia43400 UPM, Serdang, SelangorMalaysiaE-mail olCorrespondingAuthor:abubakar@ibs.upm.edu.myKey words: esterification, screening, lipases.IntroductionFatty esteramines, or esterquats, arebiodegradable raw materials for cati-onic surfactants (Puchta et al.• 1991)and are commonly incorporated intohousehold and toiletry products as wellas corrosion inhibitors. They can besynthesized from fatty acids and alka-nolamines via a rapid but energy inten-sive chemical process (Antonio et al.,1991), or, a milder, hence energy-saving, enzyme-based pathway (Idris etal .• 1995). The latter approach, beingmore selective, also results in less by-products, so reducing the off-coloursand odours, which frequently requireextensive downstream refining proce-dures. Therefore, the aim of this projectwas to develop and optimize such aprocess with lipase as the biocatalystfor the substrate pair comprising oleicacid and triethanolamine.Materials and MethodsReactions were set up with equimolaramounts of the substrates oleic acidand triethanolamine in hexane (2 ml),40 mg of enzymes were added and thereactions then allowed to proceed un-der various predetermined conditions.After a certain period, the reactionswere terminated with the addition ofacetone:ethanol (1: 1) and the mono-,di- and tri-esteramines making up theproduct mixture were separated viacolumn chromatography. The productswere then detected and analysed withthin layer (chloroform:methanol, 90: 10,v/v) as well as gas chromatography.To determine the percentage of conver-sion of the substrate oleic acid, autoti-tration with 0.05M NaOH to the end-point of pH 12 was also carried out.Results and DiscussionScreening of a range of native andimmobilized enzymes revealed theimmobilized lipase preparation Lipo-zyme IM60 to be the best biocatalystwith the reaction running optimally at50°C at a shaking speed of 350 rpm.The optimal substrate ratio was foundto be 3: I (oleic acid: triethanolamine)while the maximum substrate conver-sion was achieved after 10 h. Underthese optimal conditions, a 75% con-version of the substarte oleic acid wasobtained which surpassed that of 50-60% previously reported (Idris et al.,1995). Finally, the optimized reactionwas successfully graduiated 20 times tolaboratory scale with a working volumeof 50 m!. The model batch reactorconsisted of a round bottom flask im-mersed in a thermostated water bathand equipped with an overhead stirrer.ConclusionsThe surfactant compounds oleic es-teramines were successfully obtainedvia lipase biocatalysis. Under optimalconditions, 75% of substrate conver-sion was achieved with the productseasily separated and identified usingcolumn, thin layer and gas chromatog-raphy.Benefits from the studyNone reported.Literature cited in the textAntonio, T., Jaoquim, B. and Jessus, P.1991. PCT Int. Appl, WO 9101,295.Idris, Z .• Basri, M .• Ahmad, S., Wan Yunus,W.M.Z., Ampon, K., Razak, CN.A. andSalleh, A.B. 1995. Lipase CatalsyedSynthesis of Fatty Esteramines,Proceeding: The 6,h Asian ChemicalCongress. Manila. The Phillipines, 22-24'h May. 1995.Puchta, R., Krings. P. and Sandkuhler, P.1991. Cesio World Conference onDetergents.Project Publications inRefereed JournalsNone.Project Publications inConference ProceedingsIdris, Z., Basri, M.• Ahmad, S., Wan Yunus,W.M.Z., Ampon, K., Razak, C.A.N. andSalleh, A.B. 1995. Lipase CatalsyedSynthesis of Fatty Esteramines,Proceeding: The 6'h Asian ChemicalCongress. Manila. The Phillipines, 22-24'h May, 1995.Salleh, A.B., Balakrishnan, P., Yusof,W.Y.W., Basri, M. and Razak, CAN.1997. Production ofOleochemicalSurfacatnts, Seminar PenyelidikanFakulti. FSAS, UPM. 17 Dec 1997.Graduate ResearchZainab Idris. 1996. Enzymology [M Se].Universiti Putra Malaysia.239

Enzymatic synthesis of surfactant-like compounds

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Enzymatic synthesis of surfactant-like compounds

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