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Synthesis and Recrystallization of Adipic Acid

Page history last edited by PBworks 16 years ago

“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/Cole2)

Webpage discussion of procedure at 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

Not much really. 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.

A complete mechanism for the reaction

I added the demonstration experiment - making nylon from sebacoyl (cheaper than adipoyl) chloride and hexanediamine. The students found this 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 ideas.

 

●Use cyclohexene with various oxidizing reagents such as KMnO4 and such.

 

Student Comments 2008: Adipic Acid Synthesis

 

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