Propiolactone
Encyclopedia
β-Propiolactone is an organic compound
of the lactone
family, with a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, highly soluble in water and miscible with ethanol
, acetone
, diethyl ether
and chloroform
. The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone
.
β-Propiolactone is "reasonably expected to be a human carcinogen" (IARC
, 1999). It was once widely used in the manufacture of acrylic acid
and its esters
, but its use has been mostly phased out in favor of safer and less expensive alternatives. β-Propiolactone is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes. The principal current use of propiolactone is an intermediate in the synthesis of other chemical compounds.
β-Propiolactone will slowly react with water and hydrolyse
to produce 3-hydroxypropionic acid (hydracryclic acid).
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...
of the lactone
Lactone
In chemistry, a lactone is a cyclic ester which can be seen as the condensation product of an alcohol group -OH and a carboxylic acid group -COOH in the same molecule...
family, with a four-membered ring. It is a clear, colorless liquid with a slightly sweet odor, highly soluble in water and miscible with 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...
, acetone
Acetone
Acetone is the organic compound with the formula 2CO, a colorless, mobile, flammable liquid, the simplest example of the ketones.Acetone is miscible with water and serves as an important solvent in its own right, typically as the solvent of choice for cleaning purposes in the laboratory...
, 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...
and chloroform
Chloroform
Chloroform is an organic compound with formula CHCl3. It is one of the four chloromethanes. The colorless, sweet-smelling, dense liquid is a trihalomethane, and is considered somewhat hazardous...
. The word propiolactone usually refers to this compound, although it may also refer to α-propiolactone
Alpha-Propiolactone
α-Propiolactone, or 2-methyl-α-lactone, is a chemical compound of the lactone family, with a three-membered ring. It is a stable product which can be obtained from the 2-bromo-propionate anion. It is an intermediate in the decomposition of 2-chloropropionic acid in the gas phase....
.
β-Propiolactone is "reasonably expected to be a human carcinogen" (IARC
International Agency for Research on Cancer
The International Agency for Research on Cancer is an intergovernmental agency forming part of the World Health Organisation of the United Nations....
, 1999). It was once widely used in the manufacture of acrylic acid
Acrylic acid
Acrylic acid is an organic compound with the formula CH2=CHCO2H. It is the simplest unsaturated carboxylic acid, consisting of a vinyl group connected directly to a carboxylic acid terminus. This colorless liquid has a characteristic acrid or tart smell. It is miscible with water, alcohols,...
and its esters
Acrylate
The acrylate ion is the ion of acrylic acid.Acrylates are the salts and esters of acrylic acid. They are also known as propenoates ....
, but its use has been mostly phased out in favor of safer and less expensive alternatives. β-Propiolactone is a disinfectant and has been used to sterilize blood plasma, vaccines, tissue grafts, surgical instruments, and enzymes. The principal current use of propiolactone is an intermediate in the synthesis of other chemical compounds.
β-Propiolactone will slowly react with water and hydrolyse
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...
to produce 3-hydroxypropionic acid (hydracryclic acid).
See also
- 3-Oxetanone3-Oxetanone3-Oxetanone, also called oxetan-3-one or 1,3-epoxy-2-propanone, is a chemical compound with formula C3H4O2. It is theketone of oxetane, and an isomer of β-propiolactone.3-Oxetanone is a liquid at room temperature, that boils at 140 °C...
, an isomer of β-propiolactone - Malonic anhydrideMalonic anhydrideMalonic anhydride or oxetane-2,4-dione is an organic compound with chemical formula C3H2O3 or CH22O. It can be viewed as the anhydride of malonic acid, or a double ketone of oxetane....
(2,4-Oxetanone) - α-PropiolactoneAlpha-Propiolactoneα-Propiolactone, or 2-methyl-α-lactone, is a chemical compound of the lactone family, with a three-membered ring. It is a stable product which can be obtained from the 2-bromo-propionate anion. It is an intermediate in the decomposition of 2-chloropropionic acid in the gas phase....