SINTESIS 2-METOKSI-6-(p-FENILDIAZENILSULFONAT)-4- (FENILIMINO) FENOL DARI VANILIN SEBAGAI KEMOSENSOR SENYAWA AMINA

KRISFIAN TATA A P, Drs. Bambang Purwono, M.Sc., Ph.D.;Dra. Tutik Dwi Wahyuningsih, M.Si., Ph.D.

2018 | Skripsi | S1 KIMIA

Sintesis senyawa azo-imina, 2-metoksi-6-(p-fenildiazenilsulfonat)-4- (fenilimino) fenol (2) dari bahan dasar vanilin dan uji aktivitasnya sebagai kemosensor senyawa basa amina telah dilakukan. Sintesis senyawa 4-hidroksi-3-metoksi-5-(p-fenildiazenilsulfonat) benzaldehida (1) dilakukan melalui reaksi diazotasi antara p-anilin sulfonat dan vanilin dengan penggunaan basa K2CO3. Selanjutnya senyawa (1) direaksikan dengan anilin melalui reaksi Schiff-base imine untuk menghasilkan senyawa 2- metoksi-6-(p-fenildiazenilsulfonat)-4-(fenilimino) fenol (2). Kemurnian senyawa hasil sintesis dianalisis dengan KLT dan dilakukan uji titik lebur. Senyawa (1) dilakukan elusidasi struktur dengan instrumen FT-IR, sementara senyawa (2) dengan FT-IR dan LC-MS. Senyawa (2) dilakukan uji kemampuannya sebagai kemosensor terhadap beberapa senyawa amina, yaitu; NH3, butilamina, dietilamina dan trietilamina, serta uji kebusukan daging ayam. Kemampuan dari senyawa (2) sebagai kemosensor dianalisis dengan spektrofotometer UV-Vis. Rendemen yang diperoleh dari sintesis senyawa (1) dan (2) berturut-turut 31% dan 71%. Aktivitas senyawa (2) sebagai kemosensor dapat digunakan untuk mendeteksi senyawa amina. Senyawa amina; NH3, butilamina, dietilamina dan trietilamina memiliki limit deteksi terhadap senyawa (2) masing-masing; 256,76 ; 119,005 ; 6,2740 ; 36,640 ppm. Senyawa (2) juga mampu merespon kesegaran daging ayam.

Synthesis compound of azo-imine, 2-methoxy-6-(p-phenyl diazenilsulfonate)-4-(phenylimino)phenol (2) from vanilin and its activity test as amine base compound chemosensor has been done. Synthesis of compound 4-hydroxy-3-methoxy-5-(p-phenyl diazenylsulfonate)benzaldehyde (1) was done through diazotation reaction from p-aniline sulfonate, and vanillin by the use of base K2CO3. The compound of (1) was then reacted with aniline through Schiff-base imine reaction to produce compound of 2-methoxy-6-(p-phenyldiazenylsulfonate)-4-(phenylimino) phenol (2). Purity of compound (1) and (2) which has been shynthesized were analyzed with TLC and melting point test. Compound (1) was elucidated by FT-IR, while compound (2) by FT-IR and LC-MS. Compound (2) was tested its capability as chemosensor toward some amine compound; NH3, buthylamine, diethylamine, and triethylamine, also spoilage test for chicken meat. The capability of compound (2) as chemosensor was analyzed by UV-Vis spectrophotometer. Synthesise of compound (1) and (2) gave 31% and 71% yield, respectively. The activity of commpound (2) as chemosensor can be used to detect amine compound. Amine compounds ; NH3, butylamine, diethylamine and triethylamine have the detection limit toward compound (2) ; 256.76 ; 119.005 ; 6.2740 ; and 36.640 ppm, respetively. Compound (2) was also capable to give respond toward chicken meat freshness.

Kata Kunci : kemosensor, p-anilin sulfonat, Schiff base, solvatokromik.