AMIDATION CINNAMIC ACID BY DIETHYLAMINE WITH BORIC ACID AS CATALYST USING ULTRASONIC IRRADIATION
Abstract
Amides have important biological activities in medicine and agriculture. Amides can be synthesized in various ways, one of which is the direct reaction of carboxylic acid compounds and amines using boric acid as a catalyst. The purpose of this study was to synthesize N, N-diethyl cinnamamide compounds through direct amidation of cinnamic acid by diethylamine. The catalyst used was 5% mol of boric acid. The reaction process took place in a sonicator bath at 50oC within 40 minutes. The characterization of the compound was carried out by ATR-FTIR and 1H-NMR Spectrometry. The product of the synthesis was a 20,47% yellowish-white solid with a yield of a sapodilla fruit aroma. Identification using ATR-FTIR spectrometry showed several functional groups characteristic for Cinnamamide derivative, namely the C=O amide, C=C, C-N, aliphatic CH groups, monosubstituted benzene which were conjugated by a double bond. Characterization using 1H-NMR showed several chemical shifts for the compound N,N-diethyl cinnamamide. Based on these reason, it could be concluded that the compounds N, N-diethyl cinnamamide can be synthesized with good yields in a short time.
Keywords: amidation, boric acid, cinnamic acid, irradiation ultrasound, and N,N-diethyl cinnamamide.
Senyawa amida memiliki aktivitas biologi yang penting dalam bidang pengobatan dan juga pertanian. Amida dapat disintesis dengan berbagai cara, salah satunya adalah dengan reaksi langsung senyawa asam karboksilat dan amina menggunakan katalis asam borat. Tujuan dari penelitian ini adalah untuk mensintesis senyawa N,N-dietil sinamamida melalui amidasi langsung asam sinnamat oleh dietilamina. Katalis yang digunakan adalah asam borat 5% mol. Proses reaksi berlangsung dalam sonikator pada suhu 50oC dalam waktu 40 menit. Karakterisasi senyawa dilakukan dengan spektrometri ATR-FTIR dan 1H-NMR. Hasil sintesis berupa padatan putih kekuningan sebanyak 20,47% dengan aroma buah sawo. Identifikasi menggunakan spektrometri ATR menunjukkan beberapa gugus fungsi yang karakteristik untuk turunan sinamamida yaitu gugus C=O amida, C=C, C-N, CH alifatik, benzena monosubstitusi yang terkonjugasi oleh ikatan rangkap. Karakterisasi dengan 1H-NMR menunjukkan beberapa pergeseran kimia untuk senyawa N,N-dietil sinamamida. Berdasarkan hal-hal tersebut dapat disimpulkan bahwa hasil amidasi asam sinamat oleh dietilamina adalah N,N-dietil sinamamida dengan rendemen yang baik dalam waktu yang singkat.
Kata kunci: amidasi, asam borat, asam sinnamat, iradiasi ultrasonik dan N,N-dietil sinnamamida.
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