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°C

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.

ynthesis

Acrolein is prepared industrially by oxidation of propene. Efforts are underway to use propane 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 of potassium 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, 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.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 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. [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 of lung 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 with potassium 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 unsaturated aldehyde, acrolein (CH₂=CH-CHO), which has the peculiar odor of burnt grease.

References