Talk:Acrolein

Reference issue

Reference 2 seems to be down. —Preceding unsigned comment added by 18.4.1.146 (talk) 14:11, 4 June 2010 (UTC)

IUPAC name; Acrylaldehyde or 2-propenal?

Is the IUPAC name for Acrolein: Acrylaldehyde or 2-propenal? —Preceding unsigned comment added by 121.216.22.226 (talk) 11:14, 18 April 2008 (UTC)

Acrolein has a code of 4-3-3?

List of NFPA 704 ratings shows acrolein as having a code of 4-3-3, but this page shows a triangle of 3-2-2. Which is correct? --Ben Applegate 07:57, 24 August 2006 (UTC)

Definately 4-3-3 it is extremely toxic and if ppm of 2 can kill that is extremely toxic. --Susan Walton 03:38, 13 January 2007 (UTC)

Cooking oil

The article stated that acrolein in certain cooking oils had been linked to lung cancer. The reference cited in support of this statement spoke only to cigarette smoke, not cooking oil. Until someone comes up with a supporting reference, the statement regarding cooking oil has been removed. --Barefootmatt (talk) 17:40, 8 April 2008 (UTC)

Glycerol decompostition

I am not a chemist but the article states that "glycerol is heated to 280 °C, it decomposes into acrolein" which should be supported by the article with the reference number 2. After reading the article I believe it is rather a matter of synthesis with other chemicals not simply heating glycerol. It appears that this is a oversimplification which could probably be easily checked by a chemist. --Rene Maurin 23:30, 25 January 2007 (CET)

What I found:

Dehydration of glycerol may form a number of products, but the principal is acrolein. The reaction is the basis of several quantitative tests for glycerol. Acrolein and aldehyde condensation products are formed when glycerol vapors are passed over alumina at 360° C. Finely divided copper at 330° C. causes glycerol to decompose to acrolein, ally1 alcohol, ethyl alcohol, hydrogen and small amounts of carbon monoxide. Other catalysts will cause breakdowns of glycerol to the above products in different proportions. Glycerol is also fermented to acrolein by B. amaracrylis, the organism which produces bitterness in wine.

Glycerol in aqueous solution is decomposed by alkali at high temperatures' and pressure. At 550° F. (288° C.) there is about 4% destruction of glycerol in a 7 minute period for each percent of sodium hydroxide in the solution. Loss of glycerol in the presence of sodium carbonate is only about one tenth as great as with sodium hydroxide. Decomposition is proportional to time and double for each 25° F. increase in temperature. Substitution of nitrogen for air in the system reduces the loss of glycerol(l22).

source Ssscienccce (talk) 08:47, 16 June 2012 (UTC)

Nice broad source - I wish others used such around here instead of journal articles. The pdf is probably illegal to post it here though. And the information in your source might be dated with regards to current practices. I will update the acrolein with the modern Ullmann info.--Smokefoot (talk) 14:32, 16 June 2012 (UTC)

Monitoring difficulties, OSHA PEL...

I was about to add:

• The high reactivity of acrolein makes it a difficult chemical to monitor in air. In 2009 the EPA started monitoring acrolein levels outside 40 schools in 16 states. Discrepancies in the data and the results of a laboratory study raised significant questions about the consistency and reliability of the results. There were differences between monitors located at the same school, time between sample canister preparation and analysis of the sample influenced results, and the analysis of samples containing a known level of acrolein varied significantly between the participating labs.
  

but on reflection, it might be better if a more comprehensive overview was given. Seems that the problems in monitoring acrolein in air may be the reason why no epidemiological studies have been done (as claimed here). Acrylonitrile monitoring faces similar problems, with data for both chemicals collected by the California EPA in 2009 invalidated. (see here). Source for the above found here.
Second-hand smoke may be a minor source of acrolein exposure (compared to cooking and other indoor sources), if the results of this Canadian study are anything to go by: acrolein levels were not significantly different between houses with and without smokers (in contrast to benzene, acetaldehyde, PM2.5 and NO2 levels).
Carcinogenity has not been determined, maybe due to a lack of studies. There is a correlation between high indoor acrolein levels due to wok cooking and the high lung cancer incidence in Chinese non-smoking women, but several other chemicals in the cooking fumes could be likely suspects as well. Not sure what the current consensus is...

Regarding the OSHA PEL values: perhaps the SCOEL recommendations would be more useful? As far as I understand it, a decision by the U.S. Circuit Court of Appeals in the 1990s forced the OSHA to return to PEL values of 1971, few of them have been updated since then, and I'm unsure whether OSHA is (still) considered an authoritative source for PELs, RELs, TWAs and such, seems that some industries have adopted more stringent norms from other organisations. I came across this criticism by OSHA of it's own PEL values, but preceded by a notice saying "This is an OSHA Archive Document, and no longer represents OSHA Policy", and this page on the CDC website gives 1989 OSHA comments on acrolein, preceded by the remark "This rule was remanded by the U.S. Circuit Court of Appeals and the limits are not currently in force.". Anyway, the SCOEL recommendations are: 8 hour TWA 0.02 ppm (0.05 mg/m3) and STEL (15 mins) 0.05 ppm (0.12 mg/m3). Ssscienccce (talk) 00:45, 10 January 2014 (UTC)

e-Cigarettes?

Can this be produced from the vaporization of propylene glycol or glycerin in the fluid used by some e-cigs? Should this be added to the article?

Obviously inadequate article if it is a man made chemical and "Uses" section includes nothing on cooking oil and cigarettes. — Preceding unsigned comment added by 71.181.111.226 (talk) 19:58, 30 June 2014 (UTC)

Acrolein is a byproduct of burning cooking oil and smoking cigarettes; it is generated as the heat modifies organic compounds. It is not added intentionally, as that would be counterproductive to their purposes (acrolein is not pleasant to taste or smell). I5-X600K (talk) 18:19, 24 March 2021 (UTC)

structure

the three structures are not equivalent - the upper left is missing s hydrogen on the second carbon atom 2606:A000:4020:9300:5916:479:A94D:BB95 (talk) 01:10, 30 July 2015 (UTC)

In File:Propenal.svg (which I just replaced) some of the hydrogen atoms are implicit - in this style of representation hydrogen atoms on carbon are only shown at the terminal ends. This can be confusing so I replaced it with File:Acrolein-2D.png which I think is more clear. -- Ed (Edgar181) 22:48, 26 September 2016 (UTC)

The structures are also not those of the lowest energy conformer. The lowest energy conformer is the s-trans conformer. The s-cis conformer is the one shown. Cfn137 (talk) 22:05, 26 September 2016 (UTC)

There is no reason to assume that three dimensional structures are intended to represent the lowest energy conformation. The lowest energy conformer can vary depending on conditions (solid, solution, gas, for example) anyway, so there really isn't just one to focus on. -- Ed (Edgar181) 22:48, 26 September 2016 (UTC)

References

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A possible indicator of Multiple Sclerosis and Alzheimer's

Hopefully this won't be deleted from the talk page (I'm not arguing with anyone): acrolein was found to be a possible indicator of multiple sclerosis and Alzheimer's. Artem S. Tashkinov (talk) 13:29, 19 December 2018 (UTC)

References