Acetamide
Overview
 
Acetamide is an 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 CH3CONH2. It is the simplest amide
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 acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

. It finds some use as a plasticizer
Plasticizer
Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...

 and as an industrial solvent. The related compound N,N-dimethylacetamide
Dimethylacetamide
Dimethylacetamide is the organic compound with the formula CH3CN2. This colorless, water miscible, high boiling liquid is commonly used as a polar solvent in organic chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.The chemical reactions...

 (DMA) is more widely used, but it is not prepared from acetamide.
Acetamide can be produced in the laboratory by dehydrating
Dehydration reaction
In chemistry and the biological sciences, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions...

 ammonium acetate
Ammonium acetate
Ammonium acetate is a chemical compound with the formula CH3COONH4 . It is a white solid, which can be derived from the reaction of ammonia and acetic acid...

:
CH3COONH4 → CH3C(O)NH2 + H2O


In industry, it is typically obtained by hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 of acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...

, a byproduct of the production of acrylonitrile
Acrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...

:
CH3CN + H2O → CH3C(O)NH2

Acetamide has been detected near the center of the Milky Way
Milky Way
The Milky Way is the galaxy that contains the Solar System. This name derives from its appearance as a dim un-resolved "milky" glowing band arching across the night sky...

 galaxy.
Discussions
Encyclopedia
Acetamide is an 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 CH3CONH2. It is the simplest amide
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 acetic acid
Acetic acid
Acetic acid is an organic compound with the chemical formula CH3CO2H . It is a colourless liquid that when undiluted is also called glacial acetic acid. Acetic acid is the main component of vinegar , and has a distinctive sour taste and pungent smell...

. It finds some use as a plasticizer
Plasticizer
Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...

 and as an industrial solvent. The related compound N,N-dimethylacetamide
Dimethylacetamide
Dimethylacetamide is the organic compound with the formula CH3CN2. This colorless, water miscible, high boiling liquid is commonly used as a polar solvent in organic chemistry. DMAc is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.The chemical reactions...

 (DMA) is more widely used, but it is not prepared from acetamide.

Production and use

Acetamide can be produced in the laboratory by dehydrating
Dehydration reaction
In chemistry and the biological sciences, a dehydration reaction is usually defined as a chemical reaction that involves the loss of water from the reacting molecule. Dehydration reactions are a subset of elimination reactions...

 ammonium acetate
Ammonium acetate
Ammonium acetate is a chemical compound with the formula CH3COONH4 . It is a white solid, which can be derived from the reaction of ammonia and acetic acid...

:
CH3COONH4 → CH3C(O)NH2 + H2O


In industry, it is typically obtained by hydrolysis
Hydrolysis
Hydrolysis is a chemical reaction during which molecules of water are split into hydrogen cations and hydroxide anions in the process of a chemical mechanism. It is the type of reaction that is used to break down certain polymers, especially those made by condensation polymerization...

 of acetonitrile
Acetonitrile
Acetonitrile is the chemical compound with formula . This colourless liquid is the simplest organic nitrile. It is produced mainly as a byproduct of acrylonitrile manufacture...

, a byproduct of the production of acrylonitrile
Acrylonitrile
Acrylonitrile is the chemical compound with the formula C3H3N. This pungent-smelling colorless liquid often appears yellow due to impurities. It is an important monomer for the manufacture of useful plastics. In terms of its molecular structure, it consists of a vinyl group linked to a nitrile...

:
CH3CN + H2O → CH3C(O)NH2

Occurrence

Acetamide has been detected near the center of the Milky Way
Milky Way
The Milky Way is the galaxy that contains the Solar System. This name derives from its appearance as a dim un-resolved "milky" glowing band arching across the night sky...

 galaxy. This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth
Earth
Earth is the third planet from the Sun, and the densest and fifth-largest of the eight planets in the Solar System. It is also the largest of the Solar System's four terrestrial planets...

) can form in space.

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.

Safety

In the U.S., the California Environmental Protection Agency
California Environmental Protection Agency
The California Environmental Protection Agency is a state cabinet-level agency within the government of California. Cal/EPA is composed of six departments, boards and offices responsible for environmental research, regulating and administering the state's environmental protection programs, and...

 added acetamide to the list of compounds known to cause cancer or reproductive toxicity, for the purposes of Proposition 65.
The source of this article is wikipedia, the free encyclopedia.  The text of this article is licensed under the GFDL.
 
x
OK