Peter Kite
Junaid Muhammad
November 19, 2001
Chemistry in the News
Website Links
The article is at:
http://www.usatoday.com/news/nation/2001/08/06/trainderail.htm
For 2-Ethylhexyl Acrylate:
http://193.51.164.11/htdocs/Monographs/Vol60/M60-14.htm
http://www.itcilo.it/english/actrav/telearn/osh/ic/103117.htm
http://www.osha-slc.gov/dts/sltc/methods/partial/pv2026/2026.html
For Acetic Anhydride:
http://www.itcilo.it/english/actrav/telearn/osh/ic/108247.htm
http://www.jtbaker.com/msds/a0338.htm
http://www.osha-slc.gov/SLTC/healthguidelines/aceticanhydride/recognition.html
http://www.wellesley.edu/Chemistry/Flick/molecules/aceticanh.html
Questions
1) What substance forms acetic acid when mixed with water? (Section 20.4)
Ans: Acetic Anhydride
O O
║ ║
CH3COCCH3
2) What would be the product of a Friedel-Crafts acylation with acetic anhydride and o-Fluoroanisole? (Section 20.5)
Ans: 3-Fluoro-4-methoxyacetophenone
3) How do you synthesize 2-ethylhexyl acrylate? (Section 19.14)
Ans: This is achieved through acid-catalyzed esterification of acrylic acid and 2-ethylhexanol
4) During the acid-catalyzed esterification, does the oxygen in 2-ethylhexyl acrylate come from the carboxylic acid or the alcohol? (Section 19.14)
Ans: The C-O bond of alcohol is preserved during esterification. The oxygen that is lost as a water molecule comes from the carboxylic acid.
Editorial Comments
This article says very little about these harmful chemicals that were spilled, 2-ethylhexyl acrylate and acetic anhydride. The only significant information provided is that these chemicals are used in making plastics and act as irritants to the skin, eyes and lungs. What the article did not say was that 2-ethylhexyl acrylate is extremely toxic.
· According to http://www.osha-slc.gov/dts/sltc/methods/partial/pv2026/2026.html, when concentrated, this chemical can cause “dizziness, tiredness, headache, nausea, difficulty in breathing and convulsions.”
· In the liquid form, 2-ethylhexyl acrylate can cause severe burning of the eyes, irritation and burns.
· This chemical is used mainly in resins for latex paints and paper coating from the information on, http://193.51.164.11/htdocs/Monographs/Vol60/M60-14.htm.
· Other information on the safety and cleanup of this chemical is found at http://www.itcilo.it/english/actrav/telearn/osh/ic/103117.htm.
· 2-ethylhexyl acrylate is combustible and forms explosive vapor/air mixture at 82° C and above. It must be kept away from open flames and in a highly ventilated area. This article may not have stated all of the health risks for fear of public panic, but the evacuation of the surrounding neighborhood was clearly necessary.
· Acetic anhydride is also a flammable material that can form explosive vapor/air mixtures at just 49° C.
· This chemical must be kept away from flames, sparks, smoking and it must be highly ventilated according to http://www.itcilo.it/english/actrav/telearn/osh/ic/108247.htm.
· Irritation of the nose, throat and coughing occurs from the exposure to vapors. High concentrations cause severe damage to the lungs.
· Redness, pain and blurred vision can result from air concentrations of just 0.36 mg/m3 and lead to permanent eye damage (http://www.jtbaker.com/msds/a0338.htm).
· Spills of acetic anhydride are very dangerous. In the event of spills, an area of a half-mile in all directions should be isolated. Cleanup procedures are described at http://www.osha-lc.gov/SLTC/healthguidelines/aceticanhydride/recognition.html.
· Firefighters should wear a complete set of protective clothing and including a breathing apparatus.
· The structure of Acetic Anhydride and all relevant information can be found at http://www.wellesley.edu/Chemistry/Flick/molecules/aceticanh.html
It is clear from this article that these chemicals do not get sufficient descriptions and reports of relevant dangers. Knowing some organic chemistry helps us to better understand the significance of a chemical spill of acetic anhydride and 2-ethylhexyl acrylate. These chemicals are very serious and require professional care. Knowing the risks and effects of these chemicals heightens our concerns and awareness of these types of spills and gives us a greater appreciation for the situation.
Group Dynamics
Our group of two met once a week in the computer lab for about two hours. We searched several major online newspapers including The New York Times, and Washington Post. We did not encounter many problems within the group because there are only two people. Decisions were easy to make with only two and we worked together to complete the project efficiently. We believe this project helped us learn new chemistry websites and we were surprised at how much information could be found regarding specific chemicals. We found information on the application, handling and storage, physical and chemical properties, and first aid measures of our chemicals quite readily. The process of finding this info was eased with a group of people.