Chemistry 101 Last Name ___________ First Name First Name (Partner) Lab Time ___________ ___________ __________

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Last Name ___________ (Partner this lab) Lab Day ___________ (M,T,W,R,F)

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PREPARATION OF NYLON

Revised 3/24/2006

Nylon is one of many man-made materials called plastics. Chemically, plastics are composed of chain-like molecules of high molecular weight, called polymers, which usually have been built up from simpler chemicals called monomers. A different monomer or combination of monomers is used to manufacture each different type or family of polymers. There are many polymers around us that you have heard of or seen. Examples are Teflon, nylon, Dacron, polyethylene, polyester, Orlon, epoxy, vinyl, and boat resin. Certainly, polymers have made a great impact on our society. They are rapidly replacing many metals for making objects and man made polymeric textiles are replacing natural fibers for making cloth. Of course, in the process of creating these materials, a problem has arisen in the disposal of them.

Chemical Structure of Polymers Basically a polymer is made up of many repeating molecular units formed by sequential addition of many monomer molecules to each other. Many monomer molecules of A, say one thousand to one million, link themselves together to form a new gigantic polymeric molecule:

Many A monomer molecules

etc

A

A

A

A

A

etc

polymer molecule

An example of this type of polymer is the well-known polyethylene, as shown on the next page. In this case the monomer is ethylene. Countless numbers of these molecules link themselves together into a long chain polymeric molecule by breaking the double covalent bond and creating new single covalent bonds between the monomers.

1

A and B. many A + many B monomers etc A B A B A B etc polymer molecule An example of this type of polymer is nylon. Polypropylene is produced by reacting propylene monomer under similar conditions. Another type of polymer uses two different monomer molecules.Preparation of Nylon H many C H H C H etc H C H H C H H C H H C H etc ethylene monomer polyethylene polymer This reaction is promoted by heat. as shown below: H many C H C etc H C H C H C H C etc CH3 H polypropylene monomer CH3 H CH3 H polypropylene polymer Note that CH3's and H's alternate from carbon to carbon in this polymer. O Cl C (CH2)4 O C Cl H N H (CH2)6 N H H Cl O C (CH2)4 O C Cl loss of HCl loss of HCl O etc C (CH2)4 O C N H amide Nylon (CH2)6 N H amide O C (CH2)4 O C etc 2 . pressure and a chemical catalyst. Again this polymer may have one thousand to one million units linked together. to produce a polymer of alternating A and B.

3 . but chemically is known as a polyamide because of the type of linkage which occurs in regular intervals: O C H N an amide linkage This type of linkage is extremely important in nature because of its presence in protein or polypeptides. There are 20 different possibilities for R. many different possible proteins can exist. With the 20 different possibilities for the R group. and it is easy to begin to appreciate how important these types of polymeric substances are in nature. The new substance is given the trade name nylon. Proteins are gigantic polymeric substances made from monomer units of amino acids. Thus. HCl is lost and a covalent bond is formed in its place. An enzyme is a protein that has the specific role of acting as a biological catalyst. one can imagine the countless numbers of ways amino acids can be fastened together with the amide linkage. O H N H CH R C OH General structure for amino acid These amino acids can be linked together by means of a chemical catalyst. A generalized structure of an amino acid monomer is shown below. called an enzyme.Preparation of Nylon Note the following shorthand used in the structures above: H (CH2)4 is shorthand for C H H C H H C H H C H H (CH2)6 is shorthand for C H H C H H C H H C H H C H H C H In this reaction.

Preparation of Nylon Experimantal Introduction In this experiment. Both solutions can be found in the Working Hood in the lab opposite the Waste Hood. and two layers will form. Solution B 5% solution of adipoyl chloride (B) in cyclohexane. which have been provided in the hoods. You can then draw it out to form a long strand of nylon. the nylon will form. Imagine how many molecules have been linked together in this long strand! It is a fantastic number. to which has already been added 10 drops of 20% sodium hydroxide. At the point of contact (interface) between the layers. NOTE CAREFULLY: You must wear gloves while carrying out this experiment!!! Dispose of all liquids in the waste containers. you will use adipoyl chloride (B) dissolved in cyclohexane and add this carefully to hexamethylenediamine (A) dissolved in water. Dispose of the nylon polymer in the designated waste jar. The molecular weight of the polymer may approach one million! The reaction scheme for the formation of nylon from A and B is shown again below: O Cl C (CH2)4 O C Cl H N H B loss of HCl A loss of HCl (CH2)6 N H H Cl O C (CH2)4 O C Cl B O etc C (CH2)4 O C N H amide Nylon (CH2)6 N H amide O C (CH2)4 O C etc Solution A 5% solution of hexamethylenediamine (A) in water. 4 . These liquids will not mix.

Lay the rope on the paper towel to dry. Have your instructor approve your polymer and initial below. Squeeze your polymer dry with paper towel and discard in the appropriate waste container.Preparation of Nylon Experimental Procedure Pour 10 mL of solution A into a 50 mL beaker. producing a rope. Two layers will form (see drawing below) and there will be an immediate formation of a polymer film at the liquid-liquid interface. To this solution carefully pour 10 mL of solution B down the wall of the slightly tilted beaker. Decant the liquid into the waste container. You can break the strand by pulling it at a faster rate. Using a copper wire hook (a six-inch piece of wire bent at one end) gently free the walls of the beaker from polymer strings. Place the beaker on a piece of paper towel. which can be drawn out for many feet. (Decanting is separating a liquid from solid by carefully pouring the liquid into a separate container. vigorously stir the remainder of the two-phase system to form additional polymer.) Place the polymer remaining in the beaker on the paper towel to dry. ____________ Initials 5 . and slowly raise the wire so that polyamide forms continuously. With your piece of wire. Then hook the mass at the center.

which would be produced from the following monomers: F many C F F C F Teflon H many C H C H polystyrene H many C Cl H C H polyvinyl chloride 2. 6 .Preparation of Nylon Questions 1. On the basis of the examples given. suggest the structures of the polymers. Give the structure formed by linking 3 amino acids together. Remember that water (H2O) must be removed when forming the polymer.