Week 8: Synthesis and Recrystallization of Adipic Acid

1) Source(s)
Experiment 5, Doxsee, K. M., & Hutchison, J. E. (2004). Green organic chemistry : Strategies, tools, and laboratory experiments Southbank, Vic., Australia ; United States:
Thomson-Brooks/ColeWebpage discussion of procedure à Greener Education Materials for Chemists: Green Chemistry in the Organic Teaching Laboratory: An Environmentally Benign Synthesis of Adipic Acid.
Sato, Aoki, and Noyori. A “Green” Route to Adipic Acid: Direct Oxidation of Cyclohexenes with 30 Percent Hydrogen Peroxide. Science, 281, 09/11/1998 pp.1646-1647

2) Changes to published procedure
We kept the proportions the same as the lab manual. The first time the group ran through it, it did not work well because they were using old cyclohexene. With fresh cyclohexene and H2O2 it worked great!
We added 13 mL of the 30% H2O2 rather than 11.98 grams.
The reaction was done under reflux in a boiling water bath for one hour.
I added the demonstration experiment – making nylon from sebacoyl (cheaper than adipoyl)more01.jpg chloride and hexanediamine. The students found that somewhat amusing.
3) Positive
+Green chemistry experiments are always an opportunity to promote green chemistry which should be a deliberate emphasis in SOC.
+Uses techniques already well understood by students. In other words, its easy to do at this point in the semester.
4) Neutral
±Not much new as far as technique here.
±For some reason the most inexpensive commercial hydrogen peroxide is the %35 not %30.
5) Negative
-Melting point is a mundane way to characterize a product. How else can we characterize the product?
6) Inquiry & Extension ideas.
●Other hexenes to oxidize. The “Science” article has some suggestions.
●Use cyclohexene with various oxidizing reagents such as KMnO4 and such.
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  1. […] but that did not seem to interfere with the oxidation step. We had done this experiment in during Spring 2008. Adipic acid can be characterized by IR and melting point. It does not exit the GC very well and […]

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