THE SYNTHESIS OF SCHIFF BASE COMPOUND FROM VANILLIN AND 1,3 PROPANEDIAMINE USING THE MICROWAVE ASSISTED ORGANIC SYNTHESIS (MAOS) METHOD

• Main Author: Naufal, Ahmad
• Format: Final Project
• Language: Indonesia
• Subjects: Kimia
• Online Access: https://digilib.itb.ac.id/gdl/view/80705
• Institution: Institut Teknologi Bandung

Schiff bases are a group of compounds similar to aldehydes and ketones where an imine or azomethine group replaces the carbonyl group. Schiff bases have a general structure, namely R2C=NR' (R' ? H). Schiff base can be obtained through a condensation reaction between the carbonyl group and primary amine. The Schiff base compound N,N? bis(vanillidene)-1,3-propanediamine is one of the interesting Schiff bases because it uses raw materials of natural origin, namely vanillin. In previous research, this compound was synthesized using traditional methods such as reflux, which took 6-8 hours. To obtain this compound with a fast reaction time, the Microwave Assisted Organic Synthesis (MAOS) method is used. The p-vanillin compound was reacted with the 1,3-propanediamine compound with a mole ratio of 2:1 with ethanol solvent using the MAOS method (120 W) at 70 °C for 60 minutes. The reaction mixture was then separated using the preparative TLC method to obtain two pure product spots with a total yield of 54.28%. The two products were then characterized using IR and NMR methods. Both products provide C=N stretching vibration IR absorption peaks at 1641 and 1640 cm?1, respectively. Product 2 gives a C=C stretching vibration typical of aromatic compounds at 1595 cm?1. The results of 1H-NMR measurements for product 2 gives a typical HC=N proton signal at 8.21 ppm, a CH2-O proton signal at a chemical shift of 3.95 ppm, and a typical proton signal for aromatic compounds at a chemical shift of 6.91; 7.13; and 7.23 ppm.