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10.5 Polymerization Reactions—Monomers And Extension 12. (a) (b) Animal hides decompose quickly unless they are cured to remove the water from the skin. The hide is first soaked in water to remove water-soluble substances, and hair is removed by soaking in a mixture of lime and water, followed by an enzyme mixture. The hair and any remaining tissue are removed by machine and the hide is washed and treated with tannic acid. The tannic acid displaces water from the spaces between the protein fibres of the hide, allowing the fibres to cement together to form a strong, water-resistant leather. 13. (a) First molecule: one cis and two trans Second molecule: two cis and two trans (b) Transfats increase the level of low-density lipoprotein (LDL) or “bad” cholesterol in the bloodstream, which contributes to clogging of the arteries. As arteries clog, the risk of stroke and heart attack increases. 10.5 POLYMERIZATION REACTIONS—MONOMERS AND POLYMERS Web Activity: Web Quest—Teflon: Healthy or Hazardous? (Page 448) [Students’ presentations may cover some of the following material.] Production of Teflon To produce polytetrafluoroethylene (PTFE or Teflon®), the manufacturer first needs a steady supply of tetrafluoroethylene (TFE). To produce the required TFE, three main ingredients, fluorspar, hydrofluoric acid, and chloroform are combined in a reaction chamber and heated to between 590 ˚C and 900 ˚C. The gas produced is cooled and then distilled to remove impurities. A possible sequence of reactions is: CaF2(s) + H2SO4(aq) o CaSO4(s) + 2 HF(aq) CH4(g) + 3 Cl2(g) o CHCl3(g) + 3 HCl(g) CHCl3(g) + 2 HF(g) o CHClF2(g) + 2 HCl(g) 2 CHClF2(g) o CF2CF2(g) + 2 HCl(g) 374 Unit 5 Solutions Manual Copyright © 2007 Thomson Nelson One method of producing PTFE from the TFE is by suspension polymerization. In this process, a reaction chamber is filled with purified water and a reaction agent or initiator, which will set off the reaction of the PTFE. Liquid TFE is then piped into the reaction chamber. When it contacts the initiator, it starts the polymerization process. While this is occurring, the reaction chamber is mechanically shaken and the chamber is cooled by the flow of cold water or coolant through the walls of the chamber. When enough TFE has reacted (by mass), the water is drained from the container and the PTFE is removed. It is then dried, fed into a mill, and pulverized into a powder. Once in powder form, manufacturers typically agglomerate the PTFE into pellets, which have a consistent size and shape. In this form, the PTFE can be more easily moulded into parts by means of a variety of techniques. The dispersion polymerization method of producing PTFE agitates the chamber lightly instead of shaking it vigorously. This allows the PTFE to form into tiny beads. Added chemicals cause the beads to settle and change into a milky substance, which is called a PTFE dispersion. As a liquid, the PTFE is much easier to manipulate for use in fabric finishes and for coating metals. To coat cookware with PTFE, the item must be made of aluminium or an aluminium alloy and the surface must be prepared to receive the PTFE. First, the item is washed with detergent and then rinsed with water. The item is then etched with a solution of hydrochloric acid to roughen the surface, is rinsed with distilled water and nitric acid, and is then washed again and rinsed again with distilled water. At this point the item is coated with a primer (a trade secret) that helps the PTFE bond to it. A number of layers of PTFE are then applied, and cured onto the cookware. After the cookware has been put through a cooling process, it is ready for final assembly and packaging. The summary for the addition reaction of TFE to produce PTFE is shown on page 447 of Chapter 10. Concerns About Teflon DuPont has spent considerable effort defending both its Teflon brand name and the processes involved in its manufacture. One common misconception is that Teflon itself is dangerous, although there seems to be no scientific basis for that idea. However, there is growing evidence that chemicals involved in the manufacture of Teflon® and released during the decomposition of Teflon are dangerous. One such chemical is perfluorooctanoic acid (PFOA or C-8). PFOA is used in the manufacturing of Teflon, and testing by the FDA has shown that under normal usage Teflon coatings do not contain or emit measurable amounts of PFOA. PFOA is a concern because it is highly resistant to breaking down and accumulates in the food chain. Traces of the PFOA family of chemicals can be found in the blood of virtually everyone in North America, and as of yet there are no studies that definitively answer how this has happened. DuPont has been fined by the Environmental Protection Agency (EPA) in the United States for failing to disclose how toxic PFOA is, but DuPont has admitted no liability after settling the issue. As of February 2006, the EPA’s Science Advisory Board has voted to approve a recommendation that PFOA be considered a likely carcinogen. DuPont also claims that evaluation of human health and toxicology studies shows that PFOA does not pose a health or cancer risk to humans, and that there are no significant risks in exposure to PFOA from using Teflon. As regards overheating Teflon during the cooking process, there are conflicting opinions. DuPont claims that the maximum recommended temperature for Teflon cookware is 500 ˚F (260 ˚C), and that temperatures above that are not obtained in normal cooking processes. DuPont also claims that significant breakdown of Teflon occurs only at temperatures of 660 ˚F (349 ˚C), which is well above the smoke point for fats or butter. DuPont suggests that only leaving Copyright © 2007 Thomson Nelson Unit 5 Solutions Manual 375 cookware dry and unattended while under intense heat would cause any issue, and no matter what kind of cookware it is, that should never be done. As well, other groups, such as the American Heart Association and the National Stroke Association, claim that cooking with Teflon is still a safer and healthier alternative as you can use less fat (with lower health risks of stroke and heart disease) and improve the natural taste of foods. Beyond any health risks, it is suggested that since most kitchen fires are caused by grease and oil igniting, using non-stick cookware lessens the risk of a fire in the kitchen. Groups concerned about Teflon argue that there is a significant risk of overheating the cookware and producing toxic gases in the home. Polymer fume fever (or Teflon flu) is an acknowledged issue with overheating the coating. Symptoms include headache, chills, cough, fever, and shortness of breath, which often are similar to symptoms of the common flu virus. There are also documented cases of birds being killed when a non-stick pan is overheated in a kitchen. Birds and small animals seem to be especially sensitive to the gases produced, and even DuPont has issued a warning about this issue. Pros and Cons of Various Types of Cookware There are many pros and cons for each type of cookware. Sample answers are listed here. Ɣ Teflon Pro: cookware is now relatively inexpensive, very easy to clean, light, and allows less oil to be used in frying and cooking. Ɣ Teflon Con: can produce toxic gases when heated improperly, can be scratched over time, wears out in a few years of use, and may not have good heat retention (depending on the mass). Ɣ Steel Pro: heavier cookware has a more even heat once brought to temperature, is much longer lasting that most cookware, and has low upkeep. Ɣ Steel Con: generally quite expensive, containers are heavy, needs non-stick spray or oil to keep food from sticking, and not as good at conducting heat. Ɣ Other types of cookware that could be discussed include: glass, aluminium, steel clad, copper, ceramic, and cast iron. [Students are also expected to take a position on whether Teflon or one of its alternatives is the better option for cookware.] Practice (Page 448) (Butenes in #1 and #7 should have the location numbers between prefix and ending.) 1. (a) polymer of but-1-ene (b) polymer of vinyl fluoride (c) polymer of 1-chloro-1,2,2-trifluoroethene 376 Unit 5 Solutions Manual Copyright © 2007 Thomson Nelson (d) The presence of highly electronegative Cl and F atoms makes the polymer more polar and thus not very soluble in nonpolar organic solvents. The absence of C-H bonds and the presence of strong C-F and C-Cl bonds makes this polymer unreactive and therefore resistant to heating. The lack of bulky side chains and uniform structure makes this polymer rigid. 2. 3. (a) but-2-ene (b) 1-chloro-1,2-difluoropropene 4. The monomer must have a double or triple bond to form an addition polymer. 5. 6. (a) Typical properties of plastic are that it is flexible, light in weight, electrically nonconductive, and able to be molded into different shapes. Plastics will also soften when heated. (b) Within long polymer molecules you would expect to find intramolecular covalent bonds. Between polymer molecules there would be intermolecular forces, such as London and dipole–dipole forces. (c) Intramolecular bonding: the prevalence of single, rather than multiple, carbon–carbon bonds makes plastics strong and chemically unreactive. Intermolecular bonding: the intermolecular attractions hold the molecules together but are weaker so that the molecules can move to produce both flexibility and the ability to be molded into different shapes.
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