Oxamide is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula (CONH₂)₂. This white crystalline solid

Solid

Solid is one of the three classical states of matter . It is characterized by structural rigidity and resistance to changes of shape or volume. Unlike a liquid, a solid object does not flow to take on the shape of its container, nor does it expand to fill the entire volume available to it like a...

 is soluble in ethanol

Ethanol

Ethanol, also called ethyl alcohol, pure alcohol, grain alcohol, or drinking alcohol, is a volatile, flammable, colorless liquid. It is a psychoactive drug and one of the oldest recreational drugs. Best known as the type of alcohol found in alcoholic beverages, it is also used in thermometers, as a...

, slightly soluble in water

Water

Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...

 and insoluble in diethyl ether

Diethyl ether

Diethyl ether, also known as ethyl ether, simply ether, or ethoxyethane, is an organic compound in the ether class with the formula . It is a colorless, highly volatile flammable liquid with a characteristic odor...

. Oxamide is the diamide

Amide

In chemistry, an amide is an organic compound that contains the functional group consisting of a carbonyl group linked to a nitrogen atom . The term refers both to a class of compounds and a functional group within those compounds. The term amide also refers to deprotonated form of ammonia or an...

 derived from oxalic acid

Oxalic acid

Oxalic acid is an organic compound with the formula H2C2O4. This colourless solid is a dicarboxylic acid. In terms of acid strength, it is about 3,000 times stronger than acetic acid. Oxalic acid is a reducing agent and its conjugate base, known as oxalate , is a chelating agent for metal cations...

.

Production and applications

Oxamide is produced from hydrogen cyanide, which is oxidized to cyanogen, which is then hydrolyzed.

The main application is as substitute urea

Urea

Urea or carbamide is an organic compound with the chemical formula CO2. The molecule has two —NH2 groups joined by a carbonyl functional group....

 in fertilizers. Oxamide hydrolyzes (releases ammonia) very slowly, which is sometimes preferred vs the quick release by urea.

It is used as a stabilizer for nitrocellulose preparations. It also finds use in APCP rocket motors as a high performance burn rate suppressant. The use of oxamide in concentrations of 1-3 wt% has shown to slow the linear burn rate while having minimal impact on propellant specific impulse

Specific impulse

Specific impulse is a way to describe the efficiency of rocket and jet engines. It represents the derivative of the impulse with respect to amount of propellant used, i.e., the thrust divided by the amount of propellant used per unit time. If the "amount" of propellant is given in terms of mass ,...

.

Reactions

Upon heating above 350 °C, it decomposes to cyanogen

Cyanogen

Cyanogen is the chemical compound with the formula 2. It is a colorless, toxic gas with a pungent odor.The molecule is a pseudohalogen. Cyanogen molecules consist of two CN groups — analogous to diatomic halogen molecules, such as Cl2, but far less oxidizing...

 and water

Water

Water is a chemical substance with the chemical formula H2O. A water molecule contains one oxygen and two hydrogen atoms connected by covalent bonds. Water is a liquid at ambient conditions, but it often co-exists on Earth with its solid state, ice, and gaseous state . Water also exists in a...

. Oxamide forms self-assembled monolayers consisting of a hydrogen bonded network.