2. Refining Crude Oil Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

3. How is crude oil processed? Crude oil is petroleum in its natural liquid form. Before crude oil can be used commercially, it is heated, separated, and refined. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

4. How is crude oil processed? The process of refining crude oil is called fractional distillation. The crude oil is heated so that it vaporizes and rises through the distillation column. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

5. Refining Crude Oil At the refinery, crude oil is turned into fuels and dozens of useful products.

6. Petrochemical Products Americans consume petroleum products at a rate of three and a half gallons of oil and more than 250 cubic feet of natural gas a day per person!!

7. Petrochemical Products Most people are surprised to see how many products incorporate petroleum. InkGolf BagsCold Cream CrayonsFertilizersNylon Rope DeodorantPursesGlue ShoesFloor WaxLipstick AntifreezeUmbrellasCaulking Drinking CupsTiresDyes………….

8. Hydrocarbons There are two things that make hydrocarbons exciting to chemists: 1. Hydrocarbons contain a lot of energy!

9. Hydrocarbons The other reason for all the excitement about hydrocarbons is: 2. Hydrocarbons can take on many forms!

10. Types of Hydrocarbons 1. Alkanes or Paraffins Saturated hydrocarbons with only single C-C bonds. 2. Alkenes and Alkynes Unsaturated hydrocarbons double and triple bonds between carbon atoms. 3. Napthenes or Cycloalkanes 4. Aromatics

11. Alkanes or Paraffins General formula: C n H 2n+2 (n is a whole number, usually from 1 to 20) Straight or branched-chain molecules

12. Why are alkanes important? Alkanes with from 5 to 12 carbon atoms per molecule are found in gasoline.

13. Alkenes This is a group of unsaturated hydrocarbons that have at least one double bond. The general formula is: C n H 2n Isobutene Alkenes can be gases or liquids.

14. Why are alkenes important? The simplest alkene is ethene, C 2 H 4 (or ethylene). The controlled cracking of ethane gives ethylene, one of the most important raw materials in the plastics industry. High temperatures + H 2

15. Why are alkenes important? Multiple bonds make alkenes highly reactive. Ethylene molecules can be joined to form polyethylene, a plastic used to make bulletproof vests and helmets.

16. Why are alkenes important? Polyethylene is probably the polymer you see most in daily life. Polyethylene is the most popular plastic in the world.plastic Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

17. Why are alkenes important? The non-stick coating on this frying pan was produced accidentally by the polymerization of CF 2 =CF 2 to form -(CF 2 – CF 2 ) n - Teflon.

18. Why are alkenes important? Polymer Monomer Uses Polyvinyl H H bottles, chloride, PVC C = C credit cards H Cl -(CH 2 – CHCl) n -

19. Alkynes Alkynes are unsaturated hydrocarbons that have at least one triple bond. The general formula is C n H 2n-2 Alkynes can be gases or liquids.

20. Why are alkynes important? Acetylene The energy in the triple bond is used to power welding torches.

21. How do we get acetylene? Alkynes are highly reactive and are not found in abundance in crude oil. Acetylene is produced from methane. 4 CH 4(g) + 3 O 2(g) 2 C 2 H 2(g) + 6 H 2 O (g)

22. Napthenes or Cycloalkanes General formula: C n H 2n Saturated carbon rings Liquids at room temperature

23. Why are cycloalkanes important? Their principal use is as fuels. Fuel oil and gasoline are for the most part mixtures of alkanes and cycloalkanes.

24. Aromatic Hydrocarbons abbreviated as or The smallest aromatic is benzene. C n H n Benzene is an unsaturated ring of six carbon atoms and a liquid at room temperature.

25. Why are aromatic hydrocarbons important? Benzene is used as a solvent and as the starting point for making thousands of different compounds including: cough syrups, perfumes, artificial sweeteners, mothballs, and Styrofoam. Diet

26. Styrofoam Polymer Monomer Uses Polystyrene Foamed items and insulation CH = CH 2 -(CH – CH) n -

27. How is crude oil processed? When crude oil is heated, the hydrocarbons are separated by differences in their boiling points. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

28. How is crude oil processed? The distillation process of crude oil does not directly produce enough gasoline to meet our many demands.

29. What ’ s in a barrel of crude oil? Contents of a Typical Barrel of Crude Oil Residual Oil 39% Distillate Fuels 24% Kerosene 12% Gasoline 25% Motor fuel - Alkanes and Cycloalkanes (5 to 12 carbon atoms) Fuel for jet engines and tractors Alkanes (10 to 18 carbons) and Aromatics Diesel fuel and heating oil Alkanes (12 or more carbon atoms) Lubricating oil, motor oil and grease Alkanes, Cycloalkanes, and Aromatics (20 to 70 carbon atoms)

30. How do we get more gasoline? Refineries use thermal and catalytic cracking processes to produce more gasoline and compounds that can be used to make plastics. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

31. Cracking? In the cracking process, the hydrocarbons are mixed with a catalyst and heated to 400 to 500 o C. The heavy gas oil molecules are broken into smaller molecules which are suitable for gasoline. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

32. Cracking? Cracking also converts straight- chain alkanes into more desirable branched-chain alkanes, which burn more smoothly and are more effective fuels.

33. What ‘ s next? The products of fractional distillation and cracking are delivered to various markets such as gas stations, airports and chemical plants. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

34. What happens at the chemical plants? At chemical plants, the hydrocarbons can be further processed to make hundreds of useful products. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

35. Think of all the products made from crude oil. Petrochemical products have changed our lives!

36. From Crude To Refined

37. From Crude to Refined In this activity, you demonstrated the separation of four components found in cherry cola based on their different boiling points.

38. From Crude to Refined The four fractions (products) given off during the fractional distillation of cherry cola were: carbon dioxide gas odor of cherry cola esters water mixture of sugar and coloring

39. From Crude to Refined By graphing the relationship of time and temperature, you were able to identify the boiling point of water to be near 100 o C.

40. From Crude to Refined Crude oil is petroleum in its natural liquid form. Before crude oil can be used commercially it is heated, separated, and refined. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

41. From Crude to Refined The process of refining crude oil is called… fractional distillation. The crude oil is heated so that it vaporizes and rises through the distillation column. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

42. From Crude to Refined When crude oil is heated, the hydrocarbons are separated by differences in their.... boiling points. Hydrocarbon BP( o C) Gases 1-4 C 0 - 40 Naptha (solvents) 5-9 C 60-100 Gasoline 5-12 C 40-205 Kerosene 10-18 C 175-325 Diesel Fuel 12-20 C 250-350 Motor Oil 20-50 C 300-370 Residue 70 + C 600 + Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

43. From Crude to Refined lowest boiling points The molecules with the lowest boiling points vaporize first and condense… near the top of the distillation column. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

44. From Crude to Refined The molecules with higher boiling points are located … near the bottom. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.

45. From Crude to Refined In addition to making the oil-based products, refineries must also treat the wastes involved in the processes to minimize air and water pollution. Picture courtesy of HowStuffWorks Copyright © 1998-2004 HowStuffWorks, Inc. All rights reserved.