Purpose: To provide a general understanding of the field of modern industrial organic chemistry and relate it to the content of previous organic chemistry courses.
Text: No required text. The formal lecture presentations should be supplemented by background reading from a number of sources including the reference texts on reserve in the library:
Chenier, Philip W. Survey of Industrial Chemistry Call no.: TP145 C44 1986 Main Stacks (B2958882)
Riegel, Emil Raymond. Riegel’s Handbook of Industrial Chemistry Call no.: TP145 R54 1983 Main Stacks (B2958866)
*Wittcoff, Harold. Industrial Organic Chemicals in Perspectives Call no.: TP247 W58 V. 1-2 Sedgewick Library (B2959435)
Szmant, H.H. "Organic Building Blocks of the Chemical Industry", Wiley & Sons, 1989..
Detailed Course Outline
1. Introduction to course. Discussion of general background to topic.
Part I: Bulk Organic Chemicals
2. Industrial Organic Chemicals. Primary raw materials from petroleum and natural gas; petroleum refining reactions; cracking and reforming processes–reaction mechanisms.
3. Chemicals from Ethylene. Polymerization via free radical and acid catalysts; Ziegler process in the formation of polyethylene; addition reactions and review of mechanisms. Vinyl chloride, vinyl acetate, polystyrene etc.
4. Chemicals from Propylene. Polymerization to polypropylene; addition reactions; conversion to acrolein and acrylonitrile; cumene hydroperoxide; phenol and acetone.
5. Chemicals from the C4 Stream. Butadiene; polymerization; Diels-Alder reaction; 1,4-additions; adiponitrile and hexamethylenediamine for nylon production.
6. Chemicals from Benzene, Toluene and Xylene (BTX Process). Review of electrophilic substitution reactions; phenol-formaldehyde resins; reduction of benzene to cyclohexane; oxidation to adipic acid (nylon 6,6 and nylon 6), caprolactam from cyclohexanone oxime; Beckmann rearrangement; reactions of toluene, benzyl chloride, benzoic acid, benzaldehyde; xylene to phthalic anhydride (plasticizers).
7. Chemicals from Acetylene. Addition reactions; Reppe chemistry; trichloromethylene (degreasing), perchloroethylene (drycleaning).
8. Synthesis Gas, Ammonia (Haber Process), Carbon Monoxide.
9. Sources of Chemicals Other than Petroleum and Natural Gas. Coal, coal-tar chemicals, Fischer-Tropsch reaction, fats and oils, fatty acids and alcohols, carbohydrates, starch and cellulose, natural gums.
10. Polymers. Polymer nomenclature — classification of polymers in terms of physical/mechanical properties; relationship between properties and chemical structures; characteristics of desirable monomers.
11. Polymers. Jargon, molecular weights; how polymers are made; review earlier brief discussion on free radical and acid-catalyzed polymerization; Ziegler-Natta process, copolymerization, living polymers, block polymers, stereoregular polymers syndiotactic, isotactic, atactic).
12. Plastics. Hard tough plastics, high density polyethylene, polypropylene, polystyrene, nylon, polyvinyl chloride, phenol-formaldehyde resins, soft weak plastics, low density polyethylene.
13. Elastomers (Rubbers). Discussion on polyisoprenes; natural rubber, styrene-butadiene (SBR) rubber; "synthetic" natural rubber.
14. Catalysts. Discussion of the role of catalysts in industrial chemical processes; zeolites in petroleum refining; Ziegler-Natta catalysts in polymerization.
15. Surface Active Agents, Detergents. Mechanism of detergency; cationic and anionic surfactants; non-ionic surfactants; household detergents.
Part II: Specialty Chemicals
16. Fermentation. General discussion on the use of microorganisms (yeasts, bacteria and fungi) in production of commercial products. Specific examples chosen from the pharmaceutical industry (steroids, antibiotics etc). Use of plant cell cultures for production of plant-derived medicinal drugs. Isolation of enzymes and use of enzymes as "reagents" in organic synthesis.
17. Pharmaceuticals. Discussion on various aspects of the pharmaceutical industry–its difference from that of the petroleum and heavy chemicals industry, properties of a drug, cardiovascular drugs, drugs affecting the nervous system (barbiturates, psychotropic drugs, stimulants), antibacterial agents (sulfonamides, penicillins, cephalosporins, tetracyclines, macrolides), steroid drugs (oral contraceptives, sex hormones, adrenocortical hormones, anabolic agents, anti-inflammatory agents), analgesics (aspirin, acetaminophen), anti-histamines.
18. Dyes. Mechanism of colour formation, dyestuffs, photoactive agents, etc.