The Cyclohexanol Cycle And Nylon Synthesis
The Cyclohexanol Cycle and Nylon Synthesis
Samantha Stuckey
CHE 233L Section 302
Department of Chemistry, DePaul University, 1110 W. Belden Avenue, Chicago, IL 60614 smstuckey@comcast.net May 8th, 2013
Abstract
The first three labs of this organic chemistry experiment involved carrying out the first three parts of the Cyclohexanol Cycle. The cyclohexanol was first converted to cyclohexene and water by simple distillation (product: 6.5395g, 79.75% recovery). The cyclohexene then underwent a bromination reaction by addition of concentrated HBr and a 30% H2O2 solution, followed by an extraction of the aqueous phase. This produced trans-1,2-dibromocyclohexane (product: 12.8886g, 67.34% recovery). The trans-1,2-dibromocyclohexane was reduced by zinc metal to cyclohexene. The reaction was conducted in water, first allowing the reaction to reflux and then isolating the cyclohexene by distillation (product: 4.2144g, 95.89%).
Introduction
This experiment carries out a series of steps to carry out the Cyclohexanol Cycle. The Cyclohexanol Cycle is a multistep process that involves reacting and recycling the same product. Cyclohexanol is the starting material and ultimately is the ending material as well. The final step involves converting the cyclohexanol to nylon 6,6 (Dintzner 262). The experiment in its entirety was carried out following the major principles of green chemistry. Green chemistry is the philosophy of doing chemistry in such a way that reduces or eliminates the use and production of hazardous substances (Dintzner 262). In the dehydration of cyclohexanol, Montmorillonite K10 clay was used as an acid catalyst, which promoted dehydration. Cyclohexanol was refluxed in the presence of the catalyst. During distillation the cyclohexene product distilled from the reaction mixture along with water, and was dried with MgSO4. In the bromination of cyclohexene, Br2 was generated in situ from HBr and H2O2. The formation of the Br2 was apparent by a color change of
Samantha Stuckey
CHE 233L Section 302
Department of Chemistry, DePaul University, 1110 W. Belden Avenue, Chicago, IL 60614 smstuckey@comcast.net May 8th, 2013
Abstract
The first three labs of this organic chemistry experiment involved carrying out the first three parts of the Cyclohexanol Cycle. The cyclohexanol was first converted to cyclohexene and water by simple distillation (product: 6.5395g, 79.75% recovery). The cyclohexene then underwent a bromination reaction by addition of concentrated HBr and a 30% H2O2 solution, followed by an extraction of the aqueous phase. This produced trans-1,2-dibromocyclohexane (product: 12.8886g, 67.34% recovery). The trans-1,2-dibromocyclohexane was reduced by zinc metal to cyclohexene. The reaction was conducted in water, first allowing the reaction to reflux and then isolating the cyclohexene by distillation (product: 4.2144g, 95.89%).
Introduction
This experiment carries out a series of steps to carry out the Cyclohexanol Cycle. The Cyclohexanol Cycle is a multistep process that involves reacting and recycling the same product. Cyclohexanol is the starting material and ultimately is the ending material as well. The final step involves converting the cyclohexanol to nylon 6,6 (Dintzner 262). The experiment in its entirety was carried out following the major principles of green chemistry. Green chemistry is the philosophy of doing chemistry in such a way that reduces or eliminates the use and production of hazardous substances (Dintzner 262). In the dehydration of cyclohexanol, Montmorillonite K10 clay was used as an acid catalyst, which promoted dehydration. Cyclohexanol was refluxed in the presence of the catalyst. During distillation the cyclohexene product distilled from the reaction mixture along with water, and was dried with MgSO4. In the bromination of cyclohexene, Br2 was generated in situ from HBr and H2O2. The formation of the Br2 was apparent by a color change of