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| Acrolein | |
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| IUPAC name | Acrylaldehyde |
| Other names | Acraldehyde Acrylic Aldehyde Allyl Aldehyde Ethylene Aldehyde |
| Identifiers | |
| CAS number | 107-02-8 |
| SMILES |
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| InChI |
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| Properties | |
| Molecular formula | C3H4O |
| Molar mass | 56.06 g mol−1 |
| 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 | JT Baker MSDS |
| 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 references |
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Acrolein (systematic 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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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 potassium bisulfate on glycerol (glycerine).3
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. Acrolein is sometimes used as a fixative in preparation of biological specimens for electron microscopy.4
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 not a suspected human carcinogen; 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. 5 In October 2006, researchers found connections between acrolein in the smoke from tobacco cigarettes and the risk of lung cancer.6
EPA method 603 is designed to measure acrolein in industrial and municipal wastewater streams. 7
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.8 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
- ^ Homer Adkins and W. H. Hartung (1941). "Acrolein". Org. Synth.; Coll. Vol. 1: 15.
- ^ M J Dykstra, L E Reuss (2003) Biological Electron Microscopy: Theory, Techniques, and Troubleshooting. Springer, ISBN 0306477491, 9780306477492
- ^ http://www.healthday.com/view.cfm?id=535235
- ^ Feng, Z; Hu W, Hu Y, Tang M (October 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. http://www.pnas.org/cgi/reprint/0607031103v1.
- ^ Appendix A To Part 136 Methods For Organic Chemical Analysis of Municipal and Industrial Wastewater, Method 603—Acrolein And Acrylonitrile>
- ^ acrolein test: Definition and Much More from Answers.com
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Wikipedia content modification information:
- This page was last modified on 23 December 2008, at 23:40.
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