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    Synthesis of Nylon 6,10

    Background and Application.

    Polymers are large molecules made up by joining together many smallmolecules. The small molecules that go into making a polymer are called monomers.

    When just two monomers join together the product is called a dimer. When three,link together, a trimer. What would a molecule be called that is made up of 4

    molecues? 5 ? 6? Oligomers are medium sized molecules usually made from 8 toabout 20 molecules.

    Polymers can be made up from between about 20 and 10,000 monomers ormore. Polymers make up a large bulk of the commercially important organicchemicals.

    When a polymer is made up entirely of one monomer, it is called a homopolymer.One example is polyethylene which is made up of many ethylene units joined

    together. Polyethylene is the most common polymer used in the world. All plasticsproducts marked with a 2 inside a triangle are made of polyethylene.

     As you have seen previously, a condensation reaction is a reaction where two (ormore) molecules join together to form one larger molecule and a small moleculetypically water being produced as a side product. In today’s reaction the small sideproduct molecule is not water but HCl. Hence, this reaction should be done in thehood, and the product rinsed in sodium bicarbonate water to neutralize the acid

    before handling.

    In this reaction 1,6-hexanediamine or 1,6-diaminohexane (also commonly calledhexamethylene diamine) is reacted with sebacoyl chloride (also called decadioyl

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      Chlorinated hydrocarbons tend to be toxic. Keep methylene chloride away fromskin.

    REACTION

    PROCEDURE

    Work with a partner. Obtain two 50 mL beakers. Be sure these are veryl W h ith d t th t if L b l b k

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      Work with partner on next step. One person will hook the nylon whichforms at the interface with a copper hook and pull slowly straight up as high as

    possible. The second person uses a wooden stick and grabs a portion of nylonstring and pulls as high as they can go. Repeat until no more nylon forms.

     Another alternative to this method is for the first person to pull the nylonand wrap it on a 100 mL graduated cylinder. Then the cylinder is rotated and thenylon strand is coiled around the cylinder.

    Dunk formed nylon into sodium bicarbonate solution to neutralize anyhydrochloric acid. Dry on paper towel. Feel free to take home or tape in labnotebook.

    CLEANUP

    Dispose of residual liquid from “M” beaker into halogenated organic liquidwaste container. Dispose of residual liquid from “W” beaker into Aqueous liquidwaste container. Replace copper hook on back bench. Wipe work area downwith wet sponge. Wash hands.

    Revised November 18, 2013 S. L. Weaver 

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    Identification and uses for plastics and recycled plastics

    PlasticIdentificationCode 

    Name ofplastic

     

    Structure of Monomer and Polymer Description 

    Some uses for virgin plastic 

    Some uses for plastic made fromrecycled waste plastic

     

    polyethyleneterephthalatePET

     

    HO

    H2C CH2

    OH

    C

    O

    OHC

    O

    HO

    H3C O C

    H2

    C

    H2

    O C

    O

    C

    O

    n  

    Clear tough plastic, may beused as a fiber.

     

    Soft drink and mineral water bottles,filling for sleeping bags and pillows,textile fibers.

     

    Soft drink bottles, (multi-layer) detergentbottles, clear film for packaging, carpetfibers, fleecy jackets.

     

    high densitypolyethylene

    HDPE  H2C CH2

    H3C

    C

    H2

    H2C

    CH3

    n  

     Very common plastic, usuallywhite or colored.

     

    Crinkly shopping bags, freezer bags, milkand cream bottles, bottles for shampoo

    and cleaners, milk crates. 

    Compost bins, detergent bottles, crates,mobile rubbish bins, agricultural pipes,

    pallets, curbside recycling crates. 

    unplasticisedpolyvinyl chlorideUPVC  HC   CH2

    H3C

    CH

    H2C

    CH3

    nClCl

     

    Hard rigid plastic, may beclear. 

    Clear cordial and juice bottles, blisterpacks, plumbing pipes and fittings. 

    Detergent bottles, tiles, plumbing pipefittings. 

    plasticisedpolyvinylchloridePPVC 

    HC   CH2

    H3C

    CH

    H2C

    CH3

    nClCl  

    Flexible, clear, elastic plastic. 

    Garden hose, shoe soles, blood bags andtubing. 

    Hose inner core, industrial flooring. 

    low densitypolyethyleneLDPE  H2C CH2

    H3C

    C

    H2

    H2C

    CH3

    n  

    Soft, flexible plastic. 

    Lids of ice-cream containers, garbagebags, garbage bins, black plastic sheet. 

    Film for builders, industry, packaging andplant nurseries, bags. 

    polypropylene PP 

    HC   CH2

    H3C

    CH

    H2C

    CH3

    nH3CCH3  

    Hard, but flexible plastic -many uses. 

    Ice-cream containers, potato crisp bags,drinking straws, hinged lunch boxes. 

    Compost bins, curbside recycling crates,worm factories. 

    polystyrene PS  H

    C   CH2

    H2C

    CH

    H2C

    CH3

    n

    H2C

     

    Rigid, brittle plastic. May beclear, glassy.

     

     Yoghurt containers, plastic cutlery,imitation crystal “glassware”.

     

    Clothes pegs, coat hangers, o fficeaccessories, spools, rulers, video/CD boxes.

     

    EPS, expandedPolystyrene

     

    Foamed, lightweight, energyabsorbing, thermal insulation

     

    Hot drink cups, takeaway foodcontainers, meat trays, packaging.

     

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    other 

    Includes all other plastics, including acrylicand nylon.