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Nothing but Nylon lab report...

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Nothing but Nylon HIBA RADAD CHEM-2123-003

Abstract: The purpose of this experiment is to manufacture nylon via a polymerization reaction. In this experiment, 10 mL of a 1,6-hexanediamine/NaOH aqueous solution is prepared with 25 mL of a 0.2 M solution of decanedioyl chloride in hexane to make nylon. The nylon rope length is collected at 7.79 m, and the % yield of nylon rope was collected at 87.81%.

Introduction: All nylons share one special trait - they are large molecules that are formed by connecting many small molecules together. The type of small organic molecule used to make the polymer, the functional group (s) used to bond the molecules together, and the actual way in which the reaction takes place are all key aspects of making a useful polymer. Nylon is one of the most important commercially produced fibers. If you slept in a tent or used a toothbrush, that means you used nylon fibers. But nylon can be more than just a fiber. It is also used in gears and self-lubricating bearings. Nylon clay compounds are used to make auto parts under the hood. The two main types of nylon are nylon 6,6 and nylon 6. These two nylons have nearly identical properties. Both were invented in the late 1930s. Nylon 6,6 was discovered first. Nylon is made by joining two different organic molecules (“monomers”) together - “polymerization”. One monomer contains two amino groups - one on each end of the molecule - and the other contains two carboxylic acids, one also at each end. An amino group of a monomer binds to one carboxylic acid group than the other, creating an amide bond and leaving a functional group at each end that can interact further. When these functional groups interact,

they make a larger molecule that again contains two non-interacting functional groups, one at each end. In this experiment, 10 mL of a 1,6-hexanediamine/NaOH aqueous solution (0.5 M 1,6-hexanediamine/0.5 M NaOH) was putted in a 150-mL) beaker, 25 mL of a 0.2 M solution of decanedioyl chloride in hexane was poured down the side of the beaker to form a second layer on top of the aqueous layer. Nylon was formed through a polymerization reaction. Diameter of beaker used for wrapping the nylon was collected at 0.0551 m, and the circumference of the beaker (c = πd) was collected 0.173 m. While The number of nylon turns around the beaker was about 45 turns. The length of nylon rope was collected at 7.79 m, and the weight of nylon rope was collected at 1.235 g. The weight of limiting reagent in reaction mixture was collected at 0.581 g. while moles of limiting reagent in reaction mixture and moles of second reagent in reaction mixture that should be consumed was collected at 0.005 moles. The weight of second reagent in reaction mixture that should be consumed was collected at 1.19 g. The first mixter was 10 mL of a 1,6-hexanediamine/NaOH, and the second mixter was 25 mL of a 0.2 M solution of decanedioyl chloride in hexane. After all the calculations the theoretical yield of nylon was collected at 1.41 g, and actual yield of nylon was at 1.235 g. This indicates % yield of nylon rope was collected at 87.81%.

Materials and Methods: 25 mL of a 0.2 M solution of decanedioyl chloride, 10 mL of a 1,6-hexanediamine/NaOH, beaker.

Experimental Procedure:

1.

10 mL of a 1,6-hexanediamine/NaOH aqueous solution (0.5 M 1,6-hexanediamine/0.5 M

NaOH) was putted in a 150-mL) beaker. 2.

Slowly with care, 25 mL of a 0.2 M solution of decanedioyl chloride in hexane was

poured down the side of the beaker to form a second layer on top of the aqueous layer. 3.

The aqueous diamine layer was disturbed as little as possible.

4.

The reaction mixture was reached into with tweezers and the film of nylon that has

formed at the interface of the layers was grasped. 5.

Slowly and steadily to avoid breaking the nylon, the film was pulled out of the beaker

and the nylon was wrapped around the outside of a second, large beaker. 6.

The beaker was rotated slowly and steadily, nylon rope was pulled out of the reaction

mixture and it was wrapped around the beaker. 7.

The number of turns of nylon was counted that was able to make around the beaker

before the limiting reagent in the reaction mixture is exhausted. 8.

The nylon rope was washed thoroughly with water before handling it.

9.

It was dried it, weighed it, and the length was computed by multiplying the circumference

of the beaker times the number of turns that was achieved. 10.

The length was reported to the T A to be entered in the contest.

11.

All waste was discarded in the appropriately labeled containers.

12.

No organic materials from this experiment went down the drain in the sink! After it was

poured all the waste containers, glassware containing only residual amounts (clinging to the sides of the glassware) was washed in the sink.

Results and calculations: Diameter of beaker used for wrapping the nylon: _____0.0551_____m circumference of the beaker (c = πd): ___________0.173___________ m number of turns of nylon around the beaker: _________45_________ turns length of nylon rope: _____7.79_____m weight of nylon rope: _____1.235_____g limiting reagent in reaction mixture: _________1,6-hexanediamine/NaOH ___________ moles of limiting reagent in reaction mixture _______________0.005_______________moles weight of limiting reagent in reaction mixture _____________0.581_______________g moles of second reagent in reaction mixture that should be consumed: _______0.005______ moles weight of second reagent in reaction mixture that should be consumed: ________1.19_______ g theoretical yield of nylon: _________________1.41________________ g actual yield of nylon: ________________1.235_________________g % yield of nylon rope: _______________87.81_________________%

Discussions:

In this experiment, 10 mL of a 1,6-hexanediamine/NaOH aqueous solution (0.5 M 1,6-hexanediamine/0.5 M NaOH) was putted in a 150-mL) beaker, 25 mL of a 0.2 M solution of decanedioyl chloride in hexane was poured down the side of the beaker to form a second layer on top of the aqueous layer. Nylon was formed through a polymerization reaction. Diameter of beaker used for wrapping the nylon was collected at 0.0551 m, and the circumference of the beaker (c = πd) was collected 0.173 m. While The number of nylon turns around the beaker was about 45 turns. The length of nylon rope was collected at 7.79 m, and the weight of nylon rope was collected at 1.235 g. The weight of limiting reagent in reaction mixture was collected at 0.581 g. while moles of limiting reagent in reaction mixture and moles of second reagent in reaction mixture that should be consumed was collected at 0.005 moles. The weight of second reagent in reaction mixture that should be consumed was collected at 1.19 g. The first mixter was 10 mL of a 1,6-hexanediamine/NaOH, and the second mixter was 25 mL of a 0.2 M solution of decanedioyl chloride in hexane. After all the calculations the theoretical yield of nylon was collected at 1.41 g, and actual yield of nylon was at 1.235 g. This indicates % yield of nylon rope was collected at 87.81%.

Conclusion: Based on the observed and calculated data the nylon rope length was collected at 7.79 m, and the % yield of nylon rope was collected at 87.81%. The purpose of this experiment was to manufacture nylon via a polymerization reaction. In this experiment, 10 mL of a 1,6hexanediamine/NaOH aqueous solution was prepared with 25 mL of a 0.2 M solution of decanedioyl chloride in hexane to make nylon.

References:

file:///Users/hibaradad/Downloads/Expriment%201-1.pdf

Material Safety Data Sheet Understanding hazards associated with chemicals is an integral component of safe and responsible laboratory practice. Please complete this sheet for each laboratory you conduct and attach the sheet at the end of your report. Attach multiple sheets if using more than six chemicals. MSDS Information

1,6hexanediamine/NaO H

Liquid

10 mL

0.2 M solution of decanedioyl chloride

Liquid

25 mL

Health:3 Flammability:1 Physical Hazard:1 Personal Protection:1 Health:3 Flammability:2 Physical Hazard:1 Personal Protection:0

1. Describe a safety hazard associated with this lab and what you did to prevent it from being a problem. 1. Fire or explosions Most of the organic chemicals used in the laboratory are volatile, creating fumes that can travel long distances and may ignite if they reach a flame or spark. To avoid such conditions, secure the store for volatile chemicals in stopper bottles. 2. Thermal and chemical burns: Almost all organic and inorganic chemicals are flammable or corrosive to the skin and eyes. While handling it, it's important to be careful with chemicals to prevent spills and stains.

In case of contact with eyes or skin, rinse the contaminated body area with tap water near you immediately. Use an apron, eye glasses, hand gloves, or appropriate personal protective equipment (PPE). Make sure to keep a fire extinguisher on hand and make sure everyone in the lab knows their exact location to prevent the spread of fires. Use appropriate Personal Protective Equipment (PPE), Flame Retardant (FR) lab coat, etc. 3. The skin absorption of chemicals Some chemicals are not very corrosive, but exposure to them can cause allergic reactions or other problems if absorbed into the skin. Use an apron, eye glasses, hand gloves, or appropriate personal protective equipment (PPE). Never touch your face or eyes until your hands have been cleaned with soap or detergents. 4. Inhalation of toxic fumes Many organic solvents are highly toxic if inhaled for a long time and certain chemicals are inhaled, it causes severe irritation to the membranes of the eyes, nose, throat, and lungs. To reduce this risk, handle these chemicals in a ventilation hood. 5. Wounds to the skin Wounds to the skin are the most common type of laboratory accident. To prevent this accident, a person must work carefully, using lubricants while opening or closing the cork or seal, while handling glass corrosion applies gentle pressure as the rotation of the glass pane. 2. What is the purpose of the NaOH used in the reaction to make nylon from a diacyl chloride? While the reaction continues, HCl is generated from the coupling of the amino groups with the acyl chloride molecules.

H2N- (CH2) 6-NH2 + ClOC-CH2-CH2- COCl -----------> H2N- (CH2) 6-NH-CO-CH2-CH2COCl + HCl With a high concentration of hydrochloric acid, the unreacted amine will act as a base and denature the formed hydrochloric acid. The resulting ammonium salt is no longer nucleophilic and will not participate in the acetylation reaction. Then, to prevent this from happening, a sodium hydroxide solution is added to quench the acid that is forming, while keeping the amine in a nucleophilic form. 3. Why do the methylene chloride and hexane solutions form two layers? (Are hexane and methylene chloride immiscible? Try it!) Hexane and methylene chloride are miscible. They are not bilayer. Like melting like. Since both are organic compounds, they can be mixed freely with each. 4. Why can’t you calculate the yield of nylon in moles (the usual unit used for % yield)? 5. For industrial nylon manufacturing, would you use the di-acid or the di-acyl chloride? Why? The yield of nylon in moles cannot be counted as it will not have sufficient time to fully dry the product. So, it is not a basic method for synthesis. Another difficulty is that the length of the polymer chain can be variable, so the molecular weight of the monomer is used....