Examination and Exercise of Green Chemistry through the Cyclohexanol Cycle
Jesse Paner
CHE 233L Section 301
Department of Chemistry, DePaul University, 1110 W. Belden Avenue, Chicago, IL 60614 panerjesse@yahoo.com May 1st, 2017
Abstract Green chemistry emphasizes the utilization of chemicals to their highest efficiency and reducing the production of harmful waste. This type of chemistry was initially conceived in order to reduce the damaging impact that chemical products have on the environment. Through a series of experiments known as the cyclohexanol cycle, green chemistry was observed. The first experiment of the cycle was the dehydration of cyclohexanol; this was performed by refluxing cyclohexanol in the presence of Montmorillonite K10 an environmentally innocuous acid catalyst. This experiment produced an 11.31% yield of cyclohexene, which was later used as the starting material for …show more content…
Debromination of trans-1, 2 –dibromocyclohexane
Both the solvent and the byproduct of this reaction are easily recyclable substances.5 This correlates to another major principle of green chemistry: the use of renewable raw materials. Rather than forming unusable waste products, both substances can potentially be used as reagents in future experiment or they can be easily converted into other practical substances.
Results
Clay-catalyzed dehydration of cyclohexanol
The product collected from the first experiment was a colorless low viscosity liquid. The theoretical yield of this experiment was calculated to be 100 mmol (g). The actual yield of product collected was 11.31 mmol (g) which gave an 11.31% yield. The ¹H NMR spectrum of the cyclohexene product (see Appendix A) displayed two resonance signals at (in ppm): δ = 3.57 (d, 5H), 7.04 (s, 1H).
Table 1. Data collected from 1H NMR of dehydrated cyclohexene
Product: Cyclohexene
Theoretical Yield (mmol) 100
Actual Yield (mmol) 11.31
Percent Yield (%) 11.31 %
1H NMR Spectroscopy
Proton(s) δ (ppm)
A 3.57
B
Jesse Paner
CHE 233L Section 301
Department of Chemistry, DePaul University, 1110 W. Belden Avenue, Chicago, IL 60614 panerjesse@yahoo.com May 1st, 2017
Abstract Green chemistry emphasizes the utilization of chemicals to their highest efficiency and reducing the production of harmful waste. This type of chemistry was initially conceived in order to reduce the damaging impact that chemical products have on the environment. Through a series of experiments known as the cyclohexanol cycle, green chemistry was observed. The first experiment of the cycle was the dehydration of cyclohexanol; this was performed by refluxing cyclohexanol in the presence of Montmorillonite K10 an environmentally innocuous acid catalyst. This experiment produced an 11.31% yield of cyclohexene, which was later used as the starting material for …show more content…
Debromination of trans-1, 2 –dibromocyclohexane
Both the solvent and the byproduct of this reaction are easily recyclable substances.5 This correlates to another major principle of green chemistry: the use of renewable raw materials. Rather than forming unusable waste products, both substances can potentially be used as reagents in future experiment or they can be easily converted into other practical substances.
Results
Clay-catalyzed dehydration of cyclohexanol
The product collected from the first experiment was a colorless low viscosity liquid. The theoretical yield of this experiment was calculated to be 100 mmol (g). The actual yield of product collected was 11.31 mmol (g) which gave an 11.31% yield. The ¹H NMR spectrum of the cyclohexene product (see Appendix A) displayed two resonance signals at (in ppm): δ = 3.57 (d, 5H), 7.04 (s, 1H).
Table 1. Data collected from 1H NMR of dehydrated cyclohexene
Product: Cyclohexene
Theoretical Yield (mmol) 100
Actual Yield (mmol) 11.31
Percent Yield (%) 11.31 %
1H NMR Spectroscopy
Proton(s) δ (ppm)
A 3.57
B