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Encyclopedia > Acrolein
Acrolein
General
Systematic name Acrylaldehyde
Other names Acraldehyde
Acrylic Aldehyde
Allyl Aldehyde
Ethylene Aldehyde
Molecular formula C3H4O
SMILES C(=O)C=C
Molar mass 56.06 g/mol
Appearance Colorless to yellow liquid.
Irritating odor.
CAS number 107-02-8
Properties
Vapor density (air=1) 1.94
Solubility in water Appreciable (> 10%)
Melting point -88 °C (-126 °F)
Boiling point 53 °C (127 °F)
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. Image File history File links Size of this preview: 800 × 597 pixelsFull resolution (993 × 741 pixel, file size: 8 KB, MIME type: image/png) Estructura química de la Acroleína Description: Skeletal formula of acrolein (2-propenal, C3H8O). ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... This article or section does not cite any references or sources. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... In physics, density is mass m per unit volume V. For the common case of a homogeneous substance, it is expressed as: where, in SI units: ρ (rho) is the density of the substance, measured in kg·m-3 m is the mass of the substance, measured in kg V is... It has been suggested that this article or section be merged with Solution. ... This article describes water from a scientific and technical perspective. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... Italic text This article is about the boiling point of liquids. ... An example MSDS in a US format provides guidance for handling a hazardous substance and information on its composition and properties. ... The examples and perspective in this article or section may not represent a worldwide view. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Image File history File links NFPA_704. ... The flash point of a flammable liquid is the lowest temperature at which it can form an ignitable mixture with air. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... Organic chemistry is a specific discipline within chemistry which involves the scientific study of the structure, properties, composition, reactions, and preparation (by synthesis or by other means) of chemical compounds consisting of primarily carbon and hydrogen, which may contain any number of other elements, including nitrogen, oxygen, halogens as well... In chemistry, saturation has four different meanings: In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of that substance will appear as a precipitate. ... An aldehyde. ...

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. Propylene, also known as propene, is a colorless flammable gas with chemical formula C3H6 having a garlic odor. ... Propane is a three-carbon alkane, normally a gas, but compressible to a liquid that is transportable. ...


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. Glycerol is a chemical compound with the formula HOCH2CH(OH)CH2OH. This colorless, odorless, viscous liquid is widely used in pharmaceutical formulations. ... Sodium bisulfate, also sodium hydrogen sulfate, has formula NaHSO4. ...


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. Polyester Resin - Unsaturated Polyester Resin. ... A polyurethane is any polymer consisting of a chain of organic units joined by urethane links. ... Propylene glycol, also known as 1,2-propanediol, is an organic compound (a diol alcohol), usually a tasteless, odorless, and colorless clear oily liquid that is hygroscopic and miscible with water, acetone, and chloroform. ... Acrylic acid or prop-2-enoic acid is a chemical compound with the formula C3H4O2 and structure (which is sometimes abbreviated as CH2=CHCOOH). ... Acrylonitrile (CH2=CH-C≡N), is a pungent smelling, extremely flammable organic liquid. ... Glycerol is a chemical compound with the formula HOCH2CH(OH)CH2OH. This colorless, odorless, viscous liquid is widely used in pharmaceutical formulations. ... The Skraup synthesis is a chemical reaction used to synthesize quinolines. ...


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. [1] “The Great War ” redirects here. ... Chemical Weapons Convention Opened for signature January 13, 1993 in Paris Entered into force April 29, 1997 Conditions for entry into force Ratification by 50 states and the convening of a Preparatory Commission Parties 181 (as of Oct. ... Chemotherapy is the use of chemical substances to treat disease. ... Cyclophosphamide (the generic name for Cytoxan, Neosar) is a nitrogen mustard alkylating agent, used to treat various types of cancer and some autoimmune disorders. ... Hemorrhagic cystitis is diffuse inflammation of the bladder leading to hemorrhage. ... Parts-per notation is a measure of concentration that is used where low levels of concentration are significant. ... Trinomial name Homo sapiens sapiens Linnaeus, 1758 Humans, or human beings, are bipedal primates belonging to the mammalian species Homo sapiens (Latin: wise man or knowing man) in the family Hominidae (the great apes). ... The hazard symbol for carcinogenic chemicals in the Globally Harmonized System. ... The cigarette is the most common method of smoking tobacco. ... It has been suggested that this article or section be merged with vegetable oil. ... Lung cancer is the malignant transformation and expansion of lung tissue, and is the most lethal of all cancers worldwide, responsible for 1. ...


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.[6] 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. Glycerin, also well known as glycerine and glycerol, and less commonly as 1,2,3-propanetriol, 1,2,3-trihydroxypropane, glyceritol, and glycyl alcohol is a colorless, odorless, hygroscopic, and sweet-tasting viscous liquid. ... Potassium hydrogen sulfate, also potassium bisulfate, has formula KHSO4. ... An aldehyde. ...


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. ^ http://www.answers.com/topic/acrolein-test

External links


This article forms part of the series
Chemical warfare
Blood agents: Cyanogen chloride (CK) – Hydrogen cyanide (AC)
Blister agents: Lewisite (L) – Sulfur mustard gas (HD, H, HT, HL, HQ) – Nitrogen mustard gas (HN1, HN2, HN3)
Nerve agents: G-Agents: Tabun (GA) – Sarin (GB) – Soman (GD) – Cyclosarin (GF) – GV | V-Agents: VE – VG – VM – VX | Novichok agents
Pulmonary agents: Chlorine – Chloropicrin (PS) – Phosgene (CG) – Diphosgene (DP)
Incapacitating agents: Agent 15 (BZ) – KOLOKOL-1
Riot control agents: Pepper spray (OC) – CS gas – CN gas (mace) – CR gas
v • d • e

  Results from FactBites:
 
Acrolein - Wikipedia, the free encyclopedia (221 words)
In organic chemistry, acrolein or propenal is the simplest unsaturated aldehyde.
Acrolein is such a severe pulmonary irritant and lacrimating agent that it has been used as a chemical weapon during World War I.
Acrolein is also a metabolite of the chemotherapy drug cyclophosphamide, and is associated with hemorrhagic cystitis.
ATSDR - ToxFAQs™: Acrolein (804 words)
Acrolein is a colorless or yellow liquid with a disagreeable odor.
Acrolein is used as a pesticide to control algae, weeds, bacteria, and mollusks.
Acrolein may be found in soil, water, or air.
  More results at FactBites »


 

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