"What does alcohol distillation have in common with the nylon rope trick?"
Hands on experimentation with two common organic compounds: alcohol and nylon.
This project has the following learning goals:

Become familiar and obtain experience working with two common organic compounds.

Utilize the technique of distillation to separate alcohol from an alcohol-water mixture.

Form nylon from its reactant chemicals.
This project consists of two main investigations:
1. Separate a mixture of methanol and water using distillation techniques.
2. Form nylon from its reactant chemicals and then experiment with the material.
Investigation 1:
Alcohol, a familiar organic compound, is produced via the process of fermentation, in which the sugar molecules are converted to alcohol. Distillation is a technique used for separating out and purifying the alcohol which is produced. Distillation can also be used to separate any two liquids which have different boiling points.
In this experiment, the students will set up a distillation apparatus and separate methanol CH
3
OH (alcohol) from water. Distillation takes advantage of the different boiling points of the two liquids. Methanol's boiling point is
65 o C whereas the boiling point of pure water is 100 o C. When the two liquids (mixed together in solution) are heated, the methanol will vaporize first. The vapors, called the distillate, are "caught" in a receiving flask, and as the temperature rapidly drops, condense back into liquid.
Investigation 2:
Nylon, first produced in 1935, is one of the most commonly used polymers.
Nylon fibers are used in fabrics, the strings of musical instruments, rope and many other products. Solid nylon is used for mechanical parts such as machine screws, gears and other low- to medium-stress components previously cast in metal.

In this experiment, students will produce nylon from two chemicals, hexamethylenediamine and sebacoyl chloride.
After the chemicals are combined in a beaker, the nylon forms at the interphase where they meet. The students use forceps to pull the strings of nylon out as they are being produced. Just a small amount of reactants produces a large amount of nylon, giving rise to the "nylon rope trick" as a seemingly inexhaustible amount of nylon is continually removed from the beaker.
Methanol, distillation, boiling points, apparatus, vaporization, distillate, interphase, nylon rope, polymer
This project aims to develop students' skills in the following areas:

Measuring volume of reactants and products

Measuring temperature
 Setting up lab apparatus and use of specialized equipment and glassware
 Separating materials (distillation)

Combining materials (nylon production)
This project draws on and applies knowledge of organic compounds gained throughout the organic chemistry I course.
In particular, students will make use of the following knowledge areas:

Alcohol; Lesson 3 Oxygenates part I – properties of alcohol, including solubility and boiling point

Nylon; Lesson 5 Amines, Amides and Nitriles – components and bond formation of the nylon polymer
Students will learn how to perform the following procedures:
 Set up distillation apparatus, complete with coolant (water) tubing and heating element.

Perform a successful alcohol distillation and recover between 90 - 100% of the original alcohol volume.

Combine reactants to produce nylon from its component reactants.

Perform the "nylon rope trick" i.e. pull as much product from the reactant interphase as possible.
At the completion of the project, the students will submit a written report of their results which should include photos and/or videos of the experimental procedure.
The students will be divided into pairs or small groups to complete all parts of the project and collaborate at the end to produce the final written and digital reports and presentations.

A collaborative and written presentation will be given at the end of the learning module which will include

Data table


Discussion based on the questions presented in the lab materials

Digital media i.e. a video of the experimental procedure and photos
Sample of the nylon produced in the second investigation along with a demonstration of its properties and how this sample compares to commercially produced nylon
For the first investigation, students will be required to

Perform background research on alcohol and its properties i.e. solubility in water and boiling points as well as the science behind distillation and the equipment used.

Assemble the apparatus correctly and safely.

Perform two separate trials of separating out a sample of methanol in solution with water, and seeing how much of the original sample they are able to reclaim.

Perform a second distillation on the distillate recovered after the experiment if the volume exceeds the original amount of alcohol (more than 20 mL).
For the second investigation, students will be required to

Perform background research on the properties of nylon and its applications.

Experiment with the nylon sample produced and test its properties and possible uses.
Written and digital reports for both investigations will be presented by the students to the class at the end of the course, along with a demonstration of the properties of the nylon sample they produced.
The project includes a number of stages. The project is intended to be performed through the duration of the course. The table below summarizes the stages and timetable.
Stage
Number
Stage Name Summary
1 Research
2 Alcohol
Distillation:
Trial 1
Timetable
Research on alcohol and its properties i.e. solubility in water and boiling point, as well as become familiar with the equipment used in distillation. Research on the properties of nylon and its uses.
Weeks 1 to 2
Set up distillation apparatus and run one trial of the experiment.
Weeks 2 to 3
3
4
Alcohol
Distillation:
Trial 2
The Nylon
Set up distillation apparatus and run a second trial of the experiment.
Weeks 3 to 4
Produce nylon in the lab by combining reactants. Wash and weigh the product
Weeks 4 to 5

6
Rope Trick and experiment with its properties and uses.
Presentation Prepare report (both written and digital) on the two lab investigations of alcohol distillation and the production of nylon, as well as a demonstration of its properties and uses.
Weeks 5 to 6
For a demonstration of using simple distillation to separate methanol and water go here: http://www.youtube.com/watch?v=5b2tJYpFC7Q&feature=related (English) http://www.youtube.com/watch?v=uvxR9rOViB0 (Spanish)
Equipment:

Universal stands

Clamps


Ring clamps

Round bottom (distilling) flask
Bent glass tube
 50 mL graduated cylinder
 Condenser

Thermometer with adapter

Heating element

Rubber tubing x 2

Boiling chips
Apparatus:
Assemble all materials to form the following apparatus:
NOTE: The rubber tubing attached to the "Water out" nodule on the condenser must be hooked up to a supply of running water, such as the faucet of a lab sink. This provides the necessary coolant so the glassware does not crack during the course of the experiment. The free end of the "Water out" tubing should be placed in a sink or bucket to drain.

Set-up of the Apparatus:
1.
Attach a regular clamp and the ring clamp to the universal stand , and then attach the round-bottom flask
(distilling flask) to the clamp.
2.
Insert the adapter and thermometer into the round bottom flask.

3.
Attach the condenser.
4.
Place a second universal stand at the other end of the condenser tube, and attach a second clamp. The condenser tube should now be firmly supported on both ends.
5.
Attach two pieces of rubber tubing to the open nodules on the condenser. The free end of the tubing attached to the farther nodule should be hooked up to a faucet to bring water in. The free end of the tubing attached to the nearer nodule should be placed in a sink or bucket to drain.

6.
Turn on the water and run it through the apparatus to ensure that all tubing has been hooked up properly.
7.
Place a graduated cylinder or collecting flask underneath the free end of the condenser in order to collect the vapors/distillate. Place the heating element on the ring clamp, in position underneath the roundbottom (distilling) flask.

8.
Place several boiling chips in the round-bottom flask.
Procedure:
1.
Measure 20 mL of methanol with the graduated cylinder.
2.
Add 20 mL distilled water
3.
Transfer the methanol-water mixture into the distillation chamber. WARNING: Make sure boiling chips are already present before heating!
4.
Turn on the heating element and observe and record the initial temperature readings.

5. Observe the slowly increasing temperatures. When the temperature reaches 60-70 o C, the methanol begins to vaporize and vapor can be seen traveling along the condenser, cooling down and dripping into the collecting chamber.
6. Record the volume of methanol collected.
7. Keep track of the temperature. Assume that as long as the temperature is below 100 o C, only methanol is being collected. When the temperature reaches approximately 95 o C, turn off the heating element and wait for the temperature to decrease.
WARNING: Do not turn off the water until the contents of the distilling chamber have stopped boiling and the temperature has gone below 60 o C. Do not attempt to dismantle the apparatus or handle any of the glassware until everything has cooled down to room temperature.
8. Repeat the experiment. Afterward, average your results and record all data in the table below.
Results:
Initial
Temperature
Trial 1
Trial 2
Average
Second distillation of alcohol (Trial 1)
Second distillation of alcohol (Trial 2)
Temperature when vaporization begins o C
Temperature when vaporization of the methanol ends o C
Starting amount of methanol
(mL)
Starting amount of water in the solution (mL)
Discussion questions:
1.
Did you recover 20 mL of methanol from the distillation? Why or why not?
2.
At what temperature did you see vapors begin to rise from the distillation chamber?
Amount of distillate (mL)

3.
At what temperature did the distillate begin to collect in the receiving flask?
4.
At what temperature did the alcohol distillation end?
5.
Did you perform a second distillation of the alcohol obtained in either Trial 1 or Trial 2? If so, what were your results?
6.
What do you think would have happened if the experiment continued after the temperature reached
100 o C?
Skills
Research different aspects of the project
Superior performance 5 pts.
Apparatus assembly Apparatus assembly precisely and accurately done. Setup yields excellent results i.e. distillate recovery.
High Performance 4 pts.
Includes all details of the project, including distillation, and alcohol and its solubility and boiling point.
Includes most details of the project, including distillation, and alcohol and its solubility and boiling point.
Basic Performance 3 pts.
Includes details of distillation, and some information about alcohol.
Apparatus assembly done correctly. Setup yields good results i.e. distillate recovery.
Apparatus assembly done mostly correctly. Set-up yields adequate results i.e. some distillate recovery.
Low Performance 0 –
2.9 pts.
Includes few details of distillation and information about alcohol.
Apparatus assembly done poorly. Set-up does not yield adequate results i.e. distillate recovery.
Experimental procedures
Lab reports and presentations, including video
All equipment handled very well and safety procedures followed properly. All temperature and volume measurements precise and accurate.
Lab reports well written with clear and comprehensive results, conclusions and presentations well thought-out.
All equipment handled quite well and safety procedures followed properly. All temperature and volume measurements accurate.
Lab reports written correctly with clear results, conclusions and presentations easily understandable.
All equipment handled mostly well and safety procedures followed.
Temperature and volume measurements with few errors.
Experimental equipment handled improperly.
Temperature and volume measurements inaccurate.
Lab reports written adequately with a few errors in results, conclusions and presentations mostly easy to follow.
Lab reports made with errors in results, conclusions and presentations.
Investigation 2: The Nylon Rope Trick
In this experiment, two chemicals, hexamethylenediamine and sebacoyl chloride, are the reactants used to produce nylon. After the chemicals are combined, the nylon forms at the interphase and the students use forceps to pull the strings of nylon out as they are being produced.
For a demonstration of making nylon go here: http://www.youtube.com/watch?v=c7ihpZhCj6k (English)

http://www.youtube.com/watch?v=WP96LhGuoYQ (Spanish)
Materials:

Sebacoyl chloride solution consisting of 6g of compound dissolved in 70 mL heptane

1,6-diaminohexane solution consisting of 3g of compound dissolved in 70 mL water

Metal tweezers or forceps

Graduated cylinders
 Glass beakers
 Glass stirring rod

Balance scale

Ruler or meter stick
WARNING: Use laboratory gloves and goggles at all times. In case of chemical spills, rinse the area with water and alert your lab instructor immediately.
Procedure:
1.
Measure 5 mL of sebacoyl chloride solution into a beaker.
2.
Measure 5 mL of 1,6-diaminohexane solution into a second beaker.
3.
Tilt the beaker containing the 1,6-diaminohexane solution at an angle and slowly pour the sebacoyl chloride solution down the side of the beaker so that it forms the top layer .
4.
Observe as a thin layer of nylon forms at the interphase between the two chemical layers.
5.
Dip tweezers into the interface of the liquids and pull them up to form a strand of nylon.

6.
Continue to pull the tweezers away from the beaker to lengthen the strand.
7.
Wrap the loose end of the nylon rope around a glass stirring rod using forceps. Do not handle the nylon with your bare hands!
8.
Twist the glass stirring rod to wind the nylon rope around it.

9.
Keep twisting the rod, pulling up more nylon in the process.

10.
Continue until the nylon rope begins to thin out and eventually disappears.
Data:
11.
Rinse the nylon rope with water, ethanol or methanol to remove the acid from the nylon.
12.
Time permitting, repeat the experiment with the same or smaller amounts of reactants. Did your results match those you received the first time? Why or why not?
Amount of
Chemical Reactant
1 (mL)
Amount of
Chemical Reactant
2 (mL)
Amount of Final
Product (Nylon)
Recovered (g and
Properties
Observed (list) i.e. solubility in water, elasticity,

cm) malleability etc.
Discussion questions:
1.
What is the amount of the first chemical reactant used?
2.
What is the amount of the second chemical reactant used?
3.
What is the amount of final product recovered?
4.
Is this number greater or lower than expected, based on the amount of reactants used? Explain.
5.
Why do you think this experiment is called the "Nylon Rope Trick"?
6.
Why is it necessary to wash the nylon after it has been formed? What materials are used to wash it?
7.
What are some of the properties you observed in your final sample?
Skills
Research different aspects of the project
Experimental procedures
Lab reports and presentations, including video
Superior performance 5 pts.
High Performance 4 pts.
Basic Performance 3 pts.
Low Performance 0 –
2.9 pts.
Includes all details of the project, including nylon, its history and its possible applications.
Includes most details of the project, including nylon, its history and its applications.
All chemical reactants handled very well and mixed properly. Excellent technique for product removal. A substantial amount of final product recovered and properly washed.
All chemical reactants handled quite well and mixed properly. Good technique for product removal. A substantial amount of final product recovered and properly washed.
Includes details of nylon, and some of its applications.
All chemical reactants handled mostly well and mixed adequately.
Fair technique for product removal with some final product recovered and properly washed.
Includes few details on nylon and its applications.
Chemical reactants handled improperly.
Poor technique for product removal with little or none of final product recovered and properly washed.
Lab reports well written with clear and comprehensive results, conclusions and presentations well thought-out.
Innovative possible uses for nylon suggested.
Lab reports written correctly with clear results, conclusions and presentations easily understandable.
Lab reports written adequately with a few errors in results, conclusions and presentations mostly easy to follow.
Lab reports made with errors in results, conclusions and presentations.