IMMOBILIZATION OF HUMIC ACID ONTO CHITOSAN USING TOSYLATION METHOD WITH 1,4-BUTANEDIOL AS A SPACER ARM

https://doi.org/10.22146/ijc.21369

Uripto Trisno Santoso(1*), Radna Nurmasari(2), Dewi Umaningrum(3), Sri Juari Santosa(4), Bambang Rusdiarso(5), Dwi Siswanta(6)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lambung Mangkurat, Jl. A. Yani Km 36 Banjarbaru, Kalimantan Selatan 70714
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lambung Mangkurat, Jl. A. Yani Km 36 Banjarbaru, Kalimantan Selatan 70714
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Lambung Mangkurat, Jl. A. Yani Km 36 Banjarbaru, Kalimantan Selatan 70714
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(6) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281
(*) Corresponding Author

Abstract


Immobilization of humic acid (HA) onto chitosan using tosylation method with 1,4-butanediol as a spacer arm has been evaluated. Chitosan was phthaloylated selectively using phthalic anhydride in dimethylformamide as solvent with addition of 5% water (v/v) as cosolvent prior to be tosylated. N-phthaloyl-chitosan and HA were tosylated using tosyl chloride in excess and triethylamine as catalyst at temperature < 10 °C for 12 h. The 6-O-tosyl-N-phthaloyl-chitosan was reacted with 1,4-butanediol in order to obtain a spacer arm attached chitosan. The 6-O-butanol-N-phthaloyl-chitosan was activated by reacting with tosyl chloride. For evaluation on immobilization of HA on chitosan with and without spacer arm, 6-O-tosylbutane-N-phthaloyl-chitosan was reacted with HA and the 6-O-tosyl-N-phthaloyl-chitosan was reacted with HA. The HA immobilized onto chitosan was characterized by XRD and FTIR spectrophotometric method. The result showed that HA can be immobilized covalently onto chitosan after attaching 1,4-butanediol as spacer arm onto 6-O-tosyl-N-phthaloyl-chitosan and activating the product with tosyl chloride, but HA cannot be reacted directly onto 6-O-tosyl-N-phthaloyl-chitosan.

Keywords


immobilization; humic acid; chitosan; tosylation; spacer arm

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DOI: https://doi.org/10.22146/ijc.21369

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