What Is Oxamide?
Oxamide is an organic compound in the form of a white crystalline powder.
Its IUPAC name is ethanediamide. It is also known as oxalic diamide, diaminoglyoxal, oxalamide, oxamimidic acid, oxalic acid diamide, oxalic acid diamide Oxalic acid diamide, 2-Amino-2-oxoethanimidic acid.
Uses of Oxamide
1. Replacement of Urea Fertilizer
Oxamide is used as a slow-acting fertilizer that gradually imparts fertilizer into the soil after application. It is an excellent fertilizer because it is insoluble in water and does not absorb moisture, so there is little runoff to groundwater. It is also hydrolyzed over time by microorganisms in the soil, gradually releasing ammonia.
The decomposition rate of Oxamide and the release rate of ammonia can be adjusted according to particle size, making it easy to use and effective for labor-saving crop cultivation. Oxamide’s decomposition mechanism in the soil involves the release of a single molecule of ammonia to produce oxamic acid, which is then further decomposed into oxalic acid and ammonia.
The final decomposition products of oxalic acid are water, oxygen, and carbon dioxide. Since the decomposition products do not contain harmful byproducts such as sulfuric acid or chlorine, there is no adverse effect on the soil microbial environment, soil components, or crop growth. Oxamide itself is stable in air and is only hydrolyzed under alkaline conditions above pH 10 or acidic conditions below pH 1.
2. Other
Oxamide is also used as a stabilizer in nitrocellulose synthesis. It is also useful as a high-performance burn rate inhibitor in a fuel called ammonium perchlorate complex propellant (APCP). Oxamide at concentrations of 1-3 wt% can retard linear burn rate with minimal effect on propellant-specific impulse.
In addition, N, N’-substituted oxamides are used as auxiliary ligands in the Ullmann-Goldberg reaction. The Ullmann-Goldberg reaction is a coupling reaction of aryl halides and anilines in the presence of a copper catalyst. Among aryl halides, aryl iodide is known to be highly reactive. Aryl halides with electron-withdrawing groups also facilitate the coupling.
Properties of Oxamide
Oxamide has the chemical formula C2H4N2O2 and a molecular weight of 88.07. It is registered under CAS No. 471-46-5.
Oxamide is a solid with a density of 1.667 g/ml (20°C) that dicyanically decomposes with water at 350°C (melting point). It forms needle-like crystals and is partially sublimable. It is soluble in ethanol, almost insoluble in water, and insoluble in diethyl ether.
Other Information on Oxamide
1. How Oxamide Is Produced
Oxamide is obtained by the action of ammonia on diethyl oxalate. It can also be synthesized by partial hydrolysis of dicyanogen or by heating ammonium oxalate, the ammonium salt of oxalic acid.
2. Handling and Storage Precautions
Handling Precautions
Oxamide is designated as a dangerous substance when handled in contact with oxamide. Take care not to come in contact with it when handling or storing.
When handling, be sure to wear protective clothing, protective glasses, and protective gloves, and use them in a draft chamber. Wash hands after use.
In Case of Fire
Decomposition by combustion may produce carbon monoxide (CO), carbon dioxide (CO2), and nitrogen oxides (NOx). Use a powder fire extinguisher, foam, water spray, or carbon dioxide (CO2) to extinguish the fire. There are no prohibited fire extinguishing media.
In Case of Skin Contact
Oxamide is a skin irritant. If it gets on the skin, wash thoroughly with soap and plenty of water. If skin irritation or rash occurs, seek medical advice and attention. Wash contaminated clothing if it is to be used again.
In the Case of Eye Contact
Oxamide is a strong eye irritant. In the event of eye contact, rinse the eye carefully with water for several minutes. If eye irritation persists, seek medical attention.
Storage
Keep the container tightly closed in a cool, dark place. Store away from incompatible hazardous materials.