Acrolein
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Overview
In organic chemistry, the compound CH2=CH-CHO, more often called acrolein than the IUPAC name 2-propenal, is the simplest unsaturated aldehyde. 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.
Synthesis
Acrolein is prepared industrially by oxidation of propene. Efforts are underway to use propane as feedstock for the synthesis, however, this is more difficult.[1] Several million tonnes of acrolein are produced each year.
When glycerol is heated to 280 °C, it decomposes into acrolein.[2] Acrolein may also be produced on lab scale by the reaction of approximately 1 part sodium bisulfate on 3 parts glycerine by weight.
Uses
Acrolein is used in the preparation of polyester resin, polyurethane, propylene glycol, acrylic acid, acrylonitrile, and glycerol. 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 of quinolines, but is rarely used as such due to its instability.
Health risks
Acrolein is a severe pulmonary irritant and lacrimating agent. It has been used as a chemical weapon during World War I. It is, however, not outlawed by the Chemical Weapons Convention. Acrolein is also a metabolite of the chemotherapy drug cyclophosphamide, and is associated with hemorrhagic cystitis. Skin exposure to acrolein causes serious damage. Acrolein concentrations of 2 ppm are immediately harmful. Acrolein is a suspected human carcinogen.[3] [4] In October 2006, researchers found connections between acrolein in the smoke from tobacco cigarettes and the risk of lung cancer.[5]
Acrolein test
Acrolein test is a test for the presence of glycerin or fats. A sample is heated with potassium bisulfate, and acrolein is released if the test is positive.[6] 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, acrolein (CH2=CH-CHO), which has the peculiar odor of burnt grease.
References
- ↑ New Catalyst for the Production of Acrolein Acid
- ↑ http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20030025.pdf
- ↑ http://www.epa.gov/ttn/atw/hlthef/acrolein.html
- ↑ http://www.healthday.com/view.cfm?id=535235
- ↑ Feng, Z (Oct 2006). "Acrolein is a major cigarette-related lung cancer agent: Preferential binding at p53 mutational hotspots and inhibition of DNA repair". Proceedings of the National Academy of Sciences of the United States of America. National Academy of Sciences. 103 (42): 15404–15409. doi:10.1073/pnas.0607031103. PMID 17030796. Retrieved 2007-08-28. Unknown parameter
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