Synthesis of Organonitrogen Compounds from Eugenol through The Ritter Reaction and The Toxicity Test on Artemia salina Leach.

9th Annual Basic Science International Conference 2019

自然科学（总论）

Rahman, Mohammad Farid^1 ; Pratama, Ardhya Ayu^1

Chemistry Department, Faculty of Mathematics and Natural Sciences, Brawijaya University, Malang, Indonesia^1

关键词: Artemia salina;    Carbocations;    Isoquinolines;    Organic synthesis;    Reflux temperature;    Ritter reactions;    Strong acids;    Toxicity test;   

Others  :  https://iopscience.iop.org/article/10.1088/1757-899X/546/4/042036/pdf
DOI  :  10.1088/1757-899X/546/4/042036

学科分类：自然科学（综合）

来源: IOP

【 摘 要 】

Eugenol or 4-allyl-2-methoxyphenol is the main component in clove oil which can be used as a starting material in organic synthesis. One of the example is synthesis of organonitrogen compound through the Ritter reaction. Eugenol as a carbocation precursor is reacted with acetonitrile, in the presence of a strong acid catalyst H2SO4, to form organonitrogen compounds. The number of moles in the reaction of eugenol:acetonitrile:H2SO4 is 0.1:0.5:0.1 moles. The reaction was carried out at several conditions namely at ice temperature (0°C) for 4-hours reaction time, at room temperature (27°C) for 4 hours reaction time, and at reflux temperature (90°C) for 4, 8 and 16 hours reaction times. The products were characterized using UV-Vis, IR, and GC-MS. The 4-hours (0°C) and 4-hours (27°C) reactions did not produce any organonitrogen compounds. Meanwhile the 4-hours (90°C) reaction produces organonitrogen compounds, eugenyl acetamide. The 8-and 16-hours reflux temperature (90°C) reactions are also gives organonitrogen compounds, namely eugenyl acetamide (8% yield in 8-hours reaction time and 13% yield in 16-hours reaction time) and isoquinoline (7% yield in 8-hours reaction time and 11% yield in 16-hours reaction time), in which the yield was increased as the reaction time increased. The toxicity level of the crude obtained from the 16-hours reflux temperature (90°C) reaction time was tested using the Brain Shrimp Lethality Test method to Artemia salina. The result shows that LC50 value is 16 ppm (higher than that of eugenol) and is classified as having a strong toxicity activity.