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    besides nylon, what other product is formed from the reaction of adipoyl chloride and 1,6-diaminohexane?


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    8.25: Condensation Polymers

    Formation of a condensation polymer produces \(H_2O\), \(HCl\), or some other simple molecule, which escapes as a gas. A familiar example of a condensation polymer is nylon, which is obtained from …

    8.25: Condensation Polymers

    Last updated Apr 3, 2022

    8.24: Addition Polymers

    8.26: Cross-Linking picture_as_pdf Readability Cite this page Donate

    Ed Vitz, John W. Moore, Justin Shorb, Xavier Prat-Resina, Tim Wendorff, & Adam Hahn

    ChemPRIME at Chemical Education Digital Library (ChemEd DL)

    When addition polymers are formed, no by-products result. Formation of a condensation polymer, on the other hand, produces H2O, HCl, or some other simple molecule which escapes as a gas. A familiar example of a condensation polymer is , which is obtained from the reaction of two monomers

    These two molecules can link up with each other because each contains a reactive functional group, either an amine or a carboxylic acid which reacts to form an amide linkage. They combine as follows:

    Below is a video of the reaction to form nylon. This reaction is slightly modified from the one described above, as adipoyl chloride, not adipic acid, is used as a reactant. Thus HCl, not H2O is produced. This also means that the chain terminates in an acid chloride, rather than the carboxylic acid shown above. Note that an amide linkage is still formed.

    A solution of adipoyl chloride in cyclohexane is poured on top of an aqueous solution of 1,6-diaminohexane in a beaker. Nylon (6,6) polyamide is formed at the interface of the two immiscible liquids and is carefully drawn from the solution and placed on a glass rod. The rod is then spun, and the Nylon (6,6) polyamide is spun onto the rod.

    Well-known condensation polymers other than nylon are Dacron, Bakelite, melamine, and Mylar. Nylon makes extremely strong threads and fibers because its long-chain molecules have stronger intermolecular forces than the London forces of polyethylene. Each N—H group in a nylon chain can hydrogen bond to the O of a C=O group in a neighboring chain, as shown below. Therefore the chains cannot slide past one another easily.

    Figure 8.25.1 8.25.1

    : The three nylon molecules are held together by hydrogen bonding. The N-H group of one chain hydrogen bonds to the C=O group of another chain. This makes nylon quite strong and difficult to pull apart.

    If you pull on both ends of a nylon thread, for example, it will only stretch slightly. After that it will strongly resist breaking because a large number of hydrogen bonds are holding overlapping chains together. The same is not true of a polyethylene thread in which only London forces attract overlapping chains together, and this is one reason that polyethylene is not used to make thread.

    Source : chem.libretexts.org

    Solved Besides nylon, what other product is formed from the

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    Polymers: Demonstartion 3

    Demonstration 3

    The Formation of the Wonder Polymer

    The Condensation Polymerization Reaction Used in the Creation of Nylon 6-10

    Objective: The objective of this demonstration is to show the formation of a condensation polymer.Review of Scientific Principles:

    The word "nylon" is used to represent synthetic polyamides. The various nylons are described by a numbering system that indicates the number of carbon atoms in the monomer chains. Nylons from diamines and dicarboxylic acids are designated by two numbers, the first representing the diamine and the second the dicarboxylic acid. Thus nylon 6-10 is formed by the reaction of hexamethylenediamine and sebacic acid. In this demonstration the acid chloride, sebacyl (or Sebacoyl) chloride, is used instead of sebacic acid. The equation is:

    Many diamines and diacids (or diacid chlorides) can be reacted to make other condensation products that are described by the generic name "nylon." One such product is an important commercial polyamide, nylon 6-6, which can be prepared by substituting adipoyl chloride for Sebacoyl chloride in the procedure described here. The equation is:

    Time: About 20-30 minutes of class time.Materials and Supplies:

    50 ml 0.50 M hexamethylenediamine (1,6-diaminohexane), H2N(CH2)6NH2, in 0.5 M sodium hydroxide, NaOH (To prepare: dissolve 3.0 g of H2N(CH2)6NH2 plus 1.0 g NaOH in 50 ml distilled water. Hexamethylenediamine can be dispensed by placing the reagent bottle in hot water until sufficient solid has melted and can be decanted. The melting point is 39-40oC.)

    50 ml 0.2 M Sebacoyl chloride, ClCO(CH2)8COCl, in hexane (To prepare: dissolve 1.5 ml to 2.0 ml Sebacoyl chloride in 50 ml hexane.) gloves, plastic or rubber (ones that will not dissolve in hexane)

    250 ml beaker or crystallizing dish


    2 stirring rods or a small windlass

    food-coloring dye (optional)

    phenolphthalein (optional)

    General Safety Guidelines:

    Hexamethylenediamine is irritating to the skin, eyes, and respiratory system.

    Sodium hydroxide is extremely caustic and can cause severe burns. Contact with the skin and eyes must be prevented.

    Sebacoyl chloride is corrosive and irritating to the skin, eyes, and respiratory system.

    Hexane is extremely flammable. Hexane vapor can irritate the respiratory tract and, in high concentrations, be narcotic.


    Wearing gloves, place the hexamethylenediamine solution in a 250-ml beaker or crystallizing dish.

    Slowly pour the Sebacoyl chloride solution as a second layer on top of the diamine solution, taking care to minimize agitation at the interface.

    With forceps, grasp the polymer film that forms at the interface of the two solutions and pull it carefully from the center of the beaker.

    Wind the polymer thread on a stirring rod or a small windlass.

    Wash the polymer thoroughly with water or ethanol before handling.

    Food coloring dyes or phenolphthalein can be added to the lower (aqueous) phase to enhance the visibility of the liquid interface. The upper phase can also be colored with dyes such as azobenzene, but observation of the polymer film at the interface is somewhat obscured. Some of the dye will be taken up with the polymer, but can be removed by washing with water.

    Video Clip


    Any remaining reactants should be mixed thoroughly to produce nylon. The solid nylon should be washed before being discarded in a solid waste container.

    Any remaining liquid should be discarded in a solvent waste container or should be neutralized with either sodium bisulfate (if basic) or sodium carbonate (if acidic) and flushed down the drain with water.

    Next Topic: Crunch and Munch Lab

    Polymers Table of Contents

    MAST Home Page

    Source : matse1.matse.illinois.edu

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