My watch list
my.chemeurope.com  
Login  

Acrolein



Acrolein
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
 
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

In organic chemistry, acrolein or 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.

Additional recommended knowledge

Contents

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 action 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.[4] [5] In October 2006, researchers found connections between acrolein in tobacco cigarettes and certain cooking oils and the risk of lung cancer.[6]

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.

References

  1. ^ External MSDS
  2. ^ http://www.chinatech.com/acrolein.htm
  3. ^ http://membership.acs.org/c/ccs/pubs/CLIPS/JCE20030025.pdf
  4. ^ http://www.epa.gov/ttn/atw/hlthef/acrolein.html
  5. ^ http://www.healthday.com/view.cfm?id=535235
  6. ^ 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 of the United States of America 103 (42): 15404-15409. National Academy of Sciences. doi:10.1073/pnas.0607031103. PMID 17030796. Retrieved on 2007-08-28.
  7. ^ http://www.answers.com/topic/acrolein-test
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Acrolein". A list of authors is available in Wikipedia.
Your browser is not current. Microsoft Internet Explorer 6.0 does not support some functions on Chemie.DE