Acrolein
From Wikipedia, the free encyclopedia
| Acrolein | |
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| IUPAC name | Acrylaldehyde |
| Other names | Acraldehyde Acrylic Aldehyde Allyl Aldehyde Ethylene Aldehyde |
| Identifiers | |
| CAS number | [107-02-8] |
| SMILES | C(=O)C=C |
| Properties | |
| Molecular formula | C3H4O |
| Molar mass | 56.06 g/mol |
| Appearance | Colorless to yellow liquid. Irritating odor. |
| Melting point |
-88 °C (-126 °F) |
| Boiling point |
53 °C (127 °F) |
| Solubility in water | Appreciable (> 10%) |
| Hazards | |
| MSDS | External MSDS[1] |
| Main hazards | Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor. |
| NFPA 704 |
 3
4
3
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| Flash point | -26°C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
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[edit] 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.[2] Several million tonnes of acrolein are produced each year.
When glycerol is heated to 280 °C, it decomposes into acrolein.[3] Acrolein may also be produced on lab scale by the reaction of approximately 1 part sodium bisulfate on 3 parts glycerine by weight.
[edit] 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.
[edit] 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.[4] [5] In October 2006, researchers found connections between acrolein in the smoke from tobacco cigarettes and the risk of lung cancer.[6]
[edit] 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.[7] 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.
[edit] References
- ^ External MSDS
- ^ 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; Hu W, Hu Y, Tang M (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 103 (42): 15404-15409. doi:. PMID 17030796.
- ^ acrolein test: Definition and Much More from Answers.com
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