Page 608 - Carrahers_Polymer_Chemistry,_Eighth_Edition

Synthesis of Reactants and Intermediates for Polymers 571

17.5 SUMMARY

1. Feedstocks for the synthesis of monomers of basic polymeric materials must be readily avail-
able and inexpensive because they are utilized in polymer synthesis in large quantities, allow-
ing the polymeric materials to be inexpensive. Basic feedstocks are petrochemical and are
coal based.
2. Monomer synthesis is both an art and science developed by major and ongoing research
efforts, allowing the inexpensive and safe availability of the starting materials upon which
the polymer industry is based. Commercial monomer synthesis is based on both the availabil-
ity of inexpensive materials and on a “interconnectiveness” between products and synthetic
byproducts that are essential to the synthesis of other essential materials.

3. The precise conditions of synthesis are continually being refined. They are based on “high”
science.
4. There is an increased emphasis on green chemistry in the production of monomers.

GLOSSARY

Cannizzaro reaction: An internal oxidation–reduction reaction of aldehydes.
Carbamide: Urea.
Carcinogenic: Cancer causing.
Chemurgic Compound; compound made from a plant source.
Friedel-Crafts condensation: Condensation that takes place in the presence of a Lewis acid
such as aluminum chloride.
Grignard reagent: RMgX.
Raney nickel: A porous nickel catalyst produced from a nickel–aluminum alloy.

EXERCISES
1. Why are there so many methods for the preparation of adipic acid?
2. Write equations for the industrial synthesis of the following:
a. Adipic acid b. Hexamethylenediamine c. Sebacic acid
d. Terephthalic acid e. Maleic anhydride f. ε-Caprolactam
g. Ethylene glycol h. Glycerol i. Pentaerythritol
j. TDI k. Hexamethylenetetramine l. Phenol
m. Urea n. Melamine o. Bisphenol A
p. Epichlorohydrin q. Methyltrichlorosilane r. Styrene
s. Vinyl chloride t. Vinyl acetate u. Acrylonitrile
v. Vinyl ethyl ether w. Methyl methacrylate
3. Name a reactant or monomer produced by the following:
a. Grignard reaction b. Friedel–Crafts reaction
c. Beckman rearrangement d. A chemurgic process
e. A crossed Cannizzaro reaction
4. Why are catalysts so important in the synthesis of monomers?
5. Name three monomers that are derived from methane.
6. Why is it important to be able to make many different monomers from the same starting
feedstock?
7. What is one basic feedstock for the synthesis of bisphenol A?
8. Why are most of the major monomer producers oil companies?
9. In the synthesis of peroxides as initiators why is added care wise?
10. Why is it important to save at least some of our petroleum for future generations?
11. Name three monomers whose synthesis illustrates green chemistry.

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