471-46-5

Usage

Uses

Used in Nitrocellulose Preparations:
Oxamide is used as a stabilizer for nitrocellulose preparations, providing enhanced stability and performance in various applications.
Used in APCP Rocket Motors:
In the aerospace industry, Oxamide is utilized as a high-performance burn rate suppressant in APCP (ammonium perchlorate composite propellant) rocket motors, contributing to improved combustion control and overall performance.
Used in Agriculture:
Oxamide, a diamide of oxalic acid, is a white crystalline and non-hygroscopic fertilizer containing about 32% nitrogen, most of which is water-insoluble at 25°C. It is made from cyanogen hydrolysis in an acid medium and releases nitrogen slowly, making it an ideal choice for use as a slow-release fertilizer. Oxamide is decomposed by soil micro-organisms in the soil, providing a sustained supply of nitrogen for plant growth.

Safety Profile

Poison by ingestion and intraperitoneal routes. An eye irritant. When heated to decomposition it emits toxic fumes of NOx. See also AMIDES.

Purification Methods

Crystallise oxamide from water, grind it and dry it in an oven at 150o. [Beilstein 2 IV 1860.]

InChI:InChI=1/C2H4N2O2/c3-1(5)2(4)6/h(H2,3,5)(H2,4,6)

Upstream product

• 106-57-0 Glycine anhydride 
• 13092-86-9 diketopiperazine 
• 7359-53-7 β'-Form des Oximinomalonsaeure-amid-p-toluidids 
• 556-33-2 glycine-glycine-glycine 
• 74-90-8 hydrogen cyanide 
• 91881-03-7 leucyl=>glycyl=>glycyl=>glycine 
• 556-50-3 glycylglycine 
• 75457-07-7 N,N'-bis-(2,2,2-trichloro-1-hydroxy-ethyl)-oxalamide 
• 1113-38-8 ammonium oxalate 
• 6009-70-7 ammonium oxalate monohydrate 
• 144-62-7 oxalic acid 
• 57-13-6 urea 
• 151-50-8 potassium cyanide 
• 460-19-5 ethanedinitrile 

Downstream Products

• 120-89-8 parabanic acid 
• 463-58-1 carbon oxide sulfide 
• 556-99-0 triuret 
• 460-19-5 ethanedinitrile 
• 471-47-6 oxamic acid 
• 57-13-6 urea 
• 642-04-6 2,3,5,6-tetraphenylpyrazine 
• 60-35-5 acetamide 
• 55-21-0 benzamide 
• 620-81-5 N,N'-Diphenyloxamid 
• 10543-64-3 phenyl-oxalamide 
• 3030-75-9 2',2'-diphenyl-ethanedioic acid dihydrazide 
• 15900-11-5 (5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-pyrazol-4-ylidene)-methane 
• 21022-40-2 N,N'-bis-(4-acetylamino-phenyl)-oxalamide 

Relevant academic research and scientific papers

Efficient dimerization of formic acid in aqueous solution induced by Ar-Arc plasma

Introduction of argon-arc plasma into an aqueous solution of formic acid resulted in the formation of oxalic acid. The reaction conditions for the dimerization were studied. The maximum yield of oxalic acid reached 47-50% when the reaction was carried out using sodium formate or calcium formate. Dimerization of acetic acid was also examined.

DECOMPOSITION PRODUCTS OF HALONITROACETIC ACID DERIVATIVES

The halonitro group O2NCHX of chloro- and bromonitroacetic acid derivatives underwent reduction to H2NCO upon boiling.The same derivatives decomposed to oxalic acid upon long storage.Likely chemical transformation pathways are discussed. Keywords: chloro- and bromonitroacetic acids, reduction, oxalic acid, amides.

Preparation method of oxamide

The invention provides a preparation method of oxamide. The preparation method comprises the following steps: an intermediate oxamide derivative is prepared from CO, O2 and amine compounds as raw materials by oxidation and carbonylation under the action of a catalyst 1, and then, oxamide is prepared through aminolysis of the oxamide derivative under the action of a catalyst 2. A novel method is used for coproducing oxamide and the oxamide derivative, and the problems that oxalate synthesis materials are poisonous, catalyst efficiency is low and the like in the original technology for synthesizing oxamide through aminolysis of oxalate are solved. Besides, the technologically synthesized oxamide derivative has good substrate applicability and can be applied to fields of medicine, pesticides,synthetic ligands, food additives and the like.

Process method of co-production of oxamide and carbamic acid ester through ammonia ester exchange method

The invention discloses a process method of co-production of oxamide and carbamic acid ester through an ammonia ester exchange method. According to the process method, urea and oxalic acid diethyl serve as raw materials, and two products, namely the oxamide and the carbamic acid ester, can be obtained at the same time through a series of ammonia ester exchange reactions. By means of the process, the problems that products are singular, and by-products affect the reaction process in an original technology for synthesizing oxamide through oxalic acid diethyl ammonolysis and a technology for synthesizing carbamic acid ester through urea alcoholysis are solved; besides, due to the fact that urea is obtained through CO and NH synthesis, NH is replaced with urea, and the process method has active significance in converting CO into high added-value chemicals and efficiently utilizing CO.

Chemical evolution of simple amino acids to asparagine under discharge onto the primitive hydrosphere: Simulation experiments using contact glow discharge

Asparagine is an important amino acid for abiotic polypeptide synthesis. In simulation experiments, it was obtained in 3.0% yield (based on the amount of consumed alanine) from alanine (100 mM) and formamide (200 mM) by contact glow discharge (Harada discharge) onto aqueous solutions. The present results suggest that asparagine could be abiotically synthesized from simple amino acids under possible primitive earth conditions.

Transformation of thioamide compounds to corresponding amides using 12-Tungstosilicic acid

12-Tungstosilicic acid (H4SiW12O40) is applied for the conversion of a series of thioamides to their corresponding oxo analogues in excellent yields in acetonitrile. In the case of thioketones, no reaction is observed under these conditions. The reusability of the catalyst also is investigated.

Acidified, wet, silica-supported tetrabutylammonium periodate: A convenient and mild reagent for conversion of thioamides to their corresponding amides under solvent-free conditions

A series of thioamides are transformed to their corresponding oxo analogues in good to excellent yields with acidified, wet, silica-supported tetrabutylammonium periodate under solvent-free conditions.

A mild and convenient method for conversion of thioamides to their corresponding amides using acidified wet silica-supported permanganate under solvent-free conditions

A mild and efficient method for conversion of thioamides to their corresponding amides is reported. A series of thioamides are transformed to their corresponding carbonyl compounds in good to excellent yields by acidified wet silica-supported permanganate under solid phase conditions.

Facile desulfurization of thioamides and thioureas with tetrabutylammonium periodate under mild conditions

Thioamides and thioureas were reacted with tetrabutylammonium periodate at room temperature to afford the corresponding amides and ureas, respectively, under aprotic conditions. Springer-Verlag 2005.

Selective oxidative carbonylation of amines to oxamides and ureas catalyzed by palladium complexes

A new process for converting secondary amines into N,N,N′,N′- tetraalkyloxamides under CO pressure, catalyzed by homogeneous palladium complexes in the presence of 1,4-dichloro-2-butene (DCB) as an oxidant, has been developed. The mechanism of the oxidative double-carbonylation process, consisting of the oxidation of Pd(0) to Pd(11) with DCB through a β-chloride elimination of the η3-(chloromethyl) allylpalladiuni(11) intermediate, the formation of mono- and bis(carbamoyl)palladium species, and a reductive elimination of the two carbamoyl ligands, is proposed based on studies of the behavior of carbamoylpalladium complexes. When primary amines are employed with DCB as the oxidant, N,N′-dialkyloxamide is catalytically produced, whereas urea is exclusively produced when iodine is used as the oxidant. The reaction of an N-monopropylcarbamoylpalladium complex with propylamine under CO gave N,N′-dipropylurea, whereas a treatment with diethylamine yielded unsymmetrical N,N-diethyl-N′-propylurea, implying the intermediate formation of propyl isocyanate that is converted into the urea upon a reaction with the added amine. A kinetic study on the reaction of chloro-N- propylcarbamoylpalladium with triethylamine suggested a process proceeding through a base-promoted dcprolonalion of the N-monoalkylcarbamoyl ligand to form propyl isocyanate.