- Acrolein
Chembox new
Name = Acrolein
ImageFileL1 = Acrolein-2D-skeletal-plus-H.png
ImageSizeL1 = 100px
ImageFileR1 = Acrolein-3D-balls.png
ImageSizeR1 = 120px
ImageFile2 = Acrolein-3D-vdW.png
ImageSize2 = 120px
ImageName = Acrolein
IUPACName = Acrylaldehyde
OtherNames = Acraldehyde
Acrylic Aldehyde
Allyl Aldehyde
Ethylene Aldehyde
Section1 = Chembox Identifiers
SMILES = C(=O)C=C
InChI = 1/C3H4O/c1-2-3-4/h2-3H,1H2
CASNo = 107-02-8
ChemSpiderID=7559
Section2 = Chembox Properties
C=3|H=4|O=1
Appearance = Colorless to yellow liquid.
Irritating odor.
Solubility = Appreciable (> 10%)
MeltingPt = -88 °C (-126 °F)
BoilingPt = 53 °C (127 °F)
Section7 = Chembox Hazards
ExternalMSDS = [http://www.jtbaker.com/msds/englishhtml/a1538.htm JT Baker MSDS]
MainHazards = Highly poisonous. Causes severe irritation to exposed membranes. Extremely flammable liquid and vapor.
NFPA-H = 4
NFPA-R = 3
NFPA-F = 3
FlashPt = -26°CAcrolein (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.ynthesis
Acrolein is prepared industrially by oxidation of
propene . Efforts are underway to usepropane as feedstock for the synthesis, however, this is more difficult. [ [http://www.chinatech.com/acrolein.htm New Catalyst for the Production of Acrolein Acid ] ] Several million tonnes of acrolein are produced each year.When
glycerol is heated to 280 °C, it decomposes into acrolein. [http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20030025.pdf http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20030025.pdf] ] Acrolein may also be produced on lab scale by the reaction ofpotassium bisulfate on glycerol (glycerine). [OrgSynth | author = Homer Adkins and W. H. Hartung | title = Acrolein | collvol = 1 | collvolpages = 15 | year = 1941 | prep = cv1p0015]Uses
Acrolein is used in the preparation of
polyester resin ,polyurethane ,propylene glycol ,acrylic acid ,acrylonitrile , andglycerol .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 forelectron microscopy .M J Dykstra, L E Reuss (2003) Biological Electron Microscopy: Theory, Techniques, and Troubleshooting. Springer, ISBN 0306477491, 9780306477492]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 theChemical Weapons Convention .Acrolein is also a metabolite of thechemotherapy drugcyclophosphamide , and is associated withhemorrhagic cystitis .Skin exposure to acrolein causes serious damage. Acrolein concentrations of 2 ppm are immediately harmful.Acrolein is not a suspectedhuman 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. [http://www.healthday.com/view.cfm?id=535235 http://www.healthday.com/view.cfm?id=535235] ] In October 2006, researchers found connections between acrolein in the smoke from tobacco cigarettes and the risk oflung cancer .cite journal | last =Feng | first =Z | coauthors =Hu W, Hu Y, Tang M | title =Acrolein is a major cigarette-related lung cancer agent: Preferential binding at p53 mutational hotspots and inhibition of DNA repair | journal =Proceedings of the National Academy of Sciences | volume =103 | issue =42 | pages =15404–15409 |date =Oct 2006 | url =http://www.pnas.org/cgi/reprint/0607031103v1 | pmid =17030796 | doi=10.1073/pnas.0607031103]Acrolein test
Acrolein test is a test for the presence of
glycerin or fats. A sample is heated withpotassium bisulfate , and acrolein is released if the test is positive. [ [http://www.answers.com/topic/acrolein-test acrolein test: Definition and Much More from Answers.com ] ] 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 unsaturatedaldehyde , acrolein (CH2=CH-CHO), which has the peculiar odor of burnt grease.References
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