Acrolein

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Acrolein

Acrolein (systematic name: 2-propenal) is the simplest unsaturated

Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
aldehyde

Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
. It is produced widely but is most often immediately reacted with other products due to its instability and toxicity. It has a piercing, disagreeable, acrid smell similar to that of burning fat.

ral million tonnes of acrolein are produced each year.

When glycerol

Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
is heated to 280 °C, it decomposes into acrolein. Acrolein may also be produced on lab scale by the reaction of potassium bisulfate on glycerol (glycerine).

lein tends to polymerize when left at room temperature, leaving a gummy yellowish residue with a putrid odor.

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Synthesis

Acrolein is prepared industrially by oxidation of propene. Efforts are underway to use propane

Propane

Propane is a three-carbon alkane, normally a gas, but compressible to a transportable liquid. It is derived from other petroleum products during oil or natural gas processing....
as feedstock for the synthesis, however, this is more difficult. Several million tonnes of acrolein are produced each year.

When glycerol

Glycerol

Uses

Acrolein is used in the preparation of polyester resin

Polyester resin

Polyester resins are Unsaturated bond resins formed by the reaction of dibasic acid Organic chemistry acids and polyhydric alcohols. Among other uses, it is the basic component of sheet moulding compound and bulk moulding compound....
, polyurethane

Polyurethane

A polyurethane, commonly abbreviated PU, is any polymer consisting of a chain of organic chemistry units joined by carbamate links. Polyurethane polymers are formed by reacting a monomer containing at least two isocyanate functional groups with another monomer containing at least two alcohol groups in the presence of a catalyst....
, propylene glycol

Propylene glycol

Propylene glycol, known also by the systematic name propane-1,2-diol, is an organic compound , usually a faintly sweet, and colorless clear viscous liquid that is hygroscopic and miscible with water, acetone, and chloroform....
, acrylic acid

Acrylic acid

Acrylic acid or prop-2-enoic acid is a chemical compound and it is the simplest unsaturated compound carboxylic acid with a vinyl group at the alpha carbon position and a carboxylic acid terminus....
, acrylonitrile

Acrylonitrile

Acrylonitrile is the chemical compound with the formula CH2CHCN. This pungent-smelling colorless liquid often appears yellow due to impurities....
, and glycerol

Glycerol

Glycerol is a chemical compound also commonly called glycerin or glycerine. It is a colorless, odorless, Viscosity liquid that is widely used in pharmaceutical formulations....
. Acrolein tends to polymerize when left at room temperature, leaving a gummy yellowish residue with a putrid odor. It is also thought to be an intermediate in the Skraup synthesis

Skraup reaction

The Skraup synthesis is a chemical reaction used to synthesize quinolines. It is named after the Czech chemist Zdenko Hans Skraup . In the archetypal Skraup, aniline is heated with sulphuric acid, glycerol, and an redox, like nitrobenzene to yield quinoline....
of quinolines, but is rarely used as such due to its instability. Acrolein is sometimes used as a fixative in preparation of biological specimens for electron microscopy. It is also used as a contact herbicide to control submersed and floating weeds, as well as algae, in irrigation canals.

Health risks

Acrolein is a severe pulmonary irritant

Pulmonary agent

A pulmonary agent is a chemical weapon agent designed to impede a victim's ability to Respiratory system. They operate by causing a build-up of fluids in the lungs which then leads to...
and lachrymatory agent

Lachrymatory agent

A lachrymatory agent or lachrymator is a chemical compound that stimulates the corneal nerves in the eyes to cause tears, pain, and even temporary blindness....
. It was used as a chemical weapon during World War I

World War I

World War I, or the First World War , was a global military conflict which involved the Great powers, organized into two opposing military alliances: the Allies of World War I and the Central Powers....
. It is, however, not outlawed by the Chemical Weapons Convention

Chemical Weapons Convention

The Chemical Weapons Convention is an arms control agreement which outlaws the production, stockpiling and use of chemical warfares. Its full name is the Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and on their Destruction....
. Skin exposure to acrolein causes serious damage. Acrolein concentrations of 2 ppm are immediately harmful. Acrolein is not a suspected human

Human

A human being, also human or man, is a member of a species of bipedalism primates in the family Hominidae . Mitochondrial DNA evidence indicates that modern humans originated in east Africa about 200,000 years ago....
carcinogen

Carcinogen

The term carcinogen refers to any substance, radionuclide or radiation that is an agent directly involved in the promotion of cancer or in the increase of its propagation....
; no studies have been conducted on the carcinogenic effects of acrolein on humans, but studies on rats have shown an increase in cancerous tumors from ingestion, but not from inhalation. In October 2006, researchers found connections between acrolein in the smoke from tobacco cigarettes

Tobacco smoking

Tobacco smoking is the inhalation of smoke from burned dried or cured leaves of the tobacco plant, most often in the form of a cigarette. People may smoke casually for pleasure, habitually to satisfy an addiction to the nicotine present in tobacco and to the act of smoking, or in response to social pressure....
and the risk of lung cancer

Lung cancer

Lung cancer is a disease of uncontrolled cell growth in tissue of the lung. This growth may lead to metastasis, which is the invasion of adjacent tissue and infiltration beyond the lungs....
. Furthermore, acrolein is a toxic metabolite of cyclophosphamide

Cyclophosphamide

Cyclophosphamide , also known as cytophosphane, is a nitrogen mustard alkylating antineoplastic agent, from the oxazophorines group. It is used to treat various types of cancer and some autoimmune disorders....
, a cytotoxic chemotherapy

Chemotherapy

Chemotherapy, in its most general sense, refers to treatment of disease by chemicals that kill cells, specifically those of micro-organisms or cancer....
agent, and results in hemorrhagic cystitis

Hemorrhagic cystitis

Hemorrhagic cystitis or Haemorrhagic cystitis is diffuse inflammation of the bladder leading to dysuria, hematuria, and hemorrhage. This is seen most often in female cancer patients as a complication of therapy, however it is can also be seen in children as a result of viral infection....
.

EPA method 603 is designed to measure acrolein in industrial and municipal wastewater

Wastewater

Wastewater is any water that has been adversely affected in quality by anthropogenic influence. It comprises liquid waste discharged by domestic residences, commercial properties, industry, and/or agriculture and can encompass a wide range of potential contaminants and concentrations....
streams.

Acrolein test

Acrolein test is a test for the presence of glycerin or fat

Fat

Fats consist of a wide group of compounds that are generally soluble in organic solvents and largely insoluble in water. Chemistry, fats are generally ester of glycerol and fatty acids....
s. A sample is heated with potassium bisulfate, and acrolein is released if the test is positive. When a fat is heated strongly in the presence of a dehydrating agent such as KHSO₄, the glycerol portion of the molecule is dehydrated to form the unsaturated aldehyde

Aldehyde