Sains Malaysiana 39(5)(2010): 811–816

 

Selective Glycerol Esterification Over Organomontmorillonite Catalysts

(Pengesteran Gliserol Terpilih Menggunakan Pemangkin Organomontmorilonit)

 

Tri Yogo Wibowo

Pusat Teknologi Agroindustri

Badan Pengkajian dan Penerapan Teknologi

Jl. MH. Thamrin 8 Jakarta Pusat 10340 – Indonesia

 

Ridzuan Zakaria & Ahmad Zuhairi Abdullah*

Pusat Pengajian Kejuruteraan Kimia

Kampus Kejuruteraan, Universiti Sains Malaysia

14300 Nibong Tebal, Pulau Pinang, Malaysia

 

Received: 14 April 2000 / Accepted: 27 July 2009

 

ABSTRACT

 

Organomontmorillonites were synthesized by grafting cationic surfactants i.e quaternary ammonium compounds into the interlayer space and were characterized using XRD, FTIR and N2 adsorption/ desorption analysis. The organomontmorillonites were applied as catalyst for the esterification of glycerol (GL) with lauric acid (LA). The catalyst which had symmetrical onium salts (tetrabuthylammoniumbromide, TBAB) gave higher activity than that of unsymmetrical onium salts (cetyltrimethylammoniumbromide, CTAB). Over the TBAB-montmorillonite catalyst, glycerol monolaurate was obtained with a selectivity of about 80%, a lauric acid conversion of about 71% and a glycerol monolaurate yield of about 57%.

 

Keywords: Esterification; lauric acid; monoglyceride; montmorillonite; reaction

 

ABSTRAK

 

Organomontmorilonit telah disintesis melalui percantuman surfaktan kation iaitu sebatian ammonia kuartener kepada ruang lapisan-antara dan dicirikan menggunakan analisis XRD, FTIR dan jerapan/penyahjerapan N2. Organomontmorilonit ini telah digunakan sebagai mangkin bagi pengesteran gliserol (GL) dengan asid laurik (LA). Pemangkin yang mempunyai garam onium simetri (tetrabutilammoniumbromida, TBAB) memberikan aktiviti yang lebih tinggi berbanding pemangkin yang mempunyai garam onium tak simetri (setiltrimetilammoniumbromida, CTAB). Melalui pemangkin TBAB-montmorillonite, gliserol monolaurat telah diperolehi dengan pemilihan sebanyak 80%, penukaran asid laurik sekitar 71% dan hasilan gliserol monolaurat sekitar 57%.

 

 

Kata kunci: Asid laurik; monogliserida; montmorilonit; pengesteran; tindak balas

 

REFERENCES

 

Abro S., Pouilloux Y. & Barrault J. 1997. Selective synthesis of monoglycerides from glycerol and oleic acid in the presence of solid catalysts. Stud. Surf. Sci. Catal. 108: 539-546.

Barrer R.M. 1989. Shape-selective sorbents based on clay minerals: a review. Clays and Clay Minerals 37: 385-395.

Bossaert W.D., De Vos D.E., Van Rhijn W.M., 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.

Choy J.H., Kwak S.Y., Han Y.S. & Kim B.W. 1997. New organo-montmorillonite complexes with hydrophobic and hydrophilic functions. Mater. Lett. 33: 143-147.

Cornelis A., Laszlo P. & Pennetreau P. 1983. Some organic syntheses with clay-supported reagents. Clay Minerals 18: 437-445.

Faridi A.V. & Guggenheim S. 1997. Crystal structure of tetramethylammonium-exchanged vermiculite. Clays and Clay Minerals 45: 859.

Guner F.S., Sirkecioglu A., Ydmaz S., Erciyes A.T. & Erdem-Senatalar A. 1996. Esterification of oleic acid with glycerol in the presence of sulfated iron oxide catalyst. Journal of American Chemists’ Society 73(3): 347-351.

Heykants E., Verrelst W.H., Parton R.F. & Jacobs P.A. 1997. Shape-selective zeolite catalysed synthesis of monoglycerides by esterification of fatty acids with glycerol. Stud. Surf. Sci. Catal. 105: 1277-1284.

Lauridsen J.B. 1976. Food emulsifiers: surface activity, edibility, manufacture, composition, and application. J. Am. Oil Chem. Soc. 53: 400-407.

Lin, C.L. & Pinnavaia, T.J. 1991. Organo clay assemblies for triphase catalysis. Chem. Mater. 3: 213-215.

Li, Y. & Ishida, H. 2003. Concentration-dependent conformation of alkyl tail in the nanoconfined space: hexadecylamine in the silicate galleries. Langmuir 19: 2479.

Machado M. da S., PŽrez-Pariente J., Sastre E., Cardoso D. & de Guere–u A.M. 2000. Selective synthesis of glycerol monolaurate with zeolitic molecular sieves. Appl. Catal. A 203: 321-328.

Montanari, F. & Tundo, P. 1981. Polymer-supported phase-transfer catalysts. crown ethers and cryptands bonded by a long alkyl chain to a polystyrene matrix. J. Org. Chem. 46: 2125-2130.

Varma, R.S. & Naicker, K.P. 1998. Surfactant pillared clays in phase transfer catalysis: a new route to alkyl azides from alkyl bromides and sodium azide. Tetrahedron Lett. 39: 2915-2918.

Xi Y., Ding Z., He H. & Frost R.L. 2005. Infrared spectroscopy of organoclays synthesized with the surfactant octadecyltrimethylammonium bromide. Spectrochimica Acta Part A 61: 515-525.

Yadav G.D. & Naik S.S. 2000. Clay-supported liquid-liquid-solid phase transfer catalysis: synthesis of benzoic anhydride. Organic Process Research and Development 4: 141-146.

 

*Corresponding author; e-mail: chzuhairi@eng.usm.my

 

 

 

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