1. Organic Chemistry Carbon Based
Carbon forms bonds with many different elements.
Carbon wants to bond 4 times.
Bonding is the force that holds atoms in a molecule together.
Most of the test is based on Hydrocarbons, names and structures.
Carbon bonds 4 times with many different elements, talk about the impurities in crude and products.

2. Bonding Covalent Bonds Ionic Bonds Making or Breaking bonds.
Atoms in a molecule share electrons.
Ionic Bonds
One atom gives up an electron to the other.
Attracted by charges.
Making or Breaking bonds.
Each bond has a specific Bond energy.
Energy, usually heat, will break bonds.
Energy is giving off when bonds from.

3. What is Process Chemistry
Study of Hydrocarbons found in Crude oil
Classifications
Structure and Chemical symbols
Study of the Chemical and Physical changes taking place in a refinery.
Study of equipment used in separating and chemically changing crude products.

4. Mixture of Hydrocarbons and Impurities
Hydrogen - 14%
Sulfur - 1 to 3%
Nitrogen - less than 1%
Oxygen - less than 1%
Metals - less than 1%
Salts - less than 1%
BS&W
These are weight %

5. A Little History "Drake's Folly"
In 1859, at Titusville, Penn., Col. Edwin Drake drilled the first successful well through rock and produced crude oil.
Petroleum was prized mostly for its yield of kerosene until the turn of the century. Gasoline was burned off
By the 1920s, crude oil as an energy source - not just as a curiosity - came into its own
Kerosene was used mostly in lanterns, gasoline become valuable as the internal combustion engine gained ground.

6. Remarkably varied substance
It can be a straw-colored liquid or tar-black
Red, green and brown hues are not uncommon
Some flow about as well as cold peanut butter.

7. Basic Types of Crude oils
Paraffinic
Mostly Paraffin
Waxy
Naphthenic
Mostly cyclo-paraffins
Sweet
Little or no Sulfur
Sour
Lots of Sulfur

9. Hydrocarbons A group of Compounds in Organic Chemistry.
Referred to as “Oils” or Petroleum.
Compounds are mainly Hydrogen and Carbon
Can contain other elements such as Sulfur, Nitrogen, and Heavy Metals.
Closely related to vegetable oils, and alcohols.

10. Classifications of Hydrocarbons
Alkanes (Paraffin’s) - Single Bonds
Chains, Branched changes (Isomers), or rings (Cyclo-)
Alkenes (Olefin’s) - Contain at least one double bond
Alkynes – Triple bonds
Aromatics – Base is a Benzene ring
Naphthalenes – Cyclo-paraffins
Mention the endings ane = 1 bond
ene = 2 bonds
yne = 3 bonds
Put the endings in alphabetically order to remember the bonding.

11. Alkanes Ranging from C1 to C50+ Saturated Hydrocarbons
Straight or Branched Chains.
All Bonds are single bonds.
Ending in – “ane”
Chemical Symbols
CnH2n+2
Referred to as normal
nbutane or nC4.
Ranging from C1 to C50+
Saturated Hydrocarbons
Meaning it has its full amount of Hydrogen
No double bonds.
Paraffinic / Waxy
Stable compounds
Review and spend some time on the formula this will help them later on the test and in Jeopardy, use several examples. Write C4 and ask how many hydrogen, the switch it and say H12 so they can use the formula to go backwards.

12. Top Ten Paraffin's Methane CH4 Ethane C2H6 Propane C3H8 Butane C4H10
Pentane C5H12
Hexane C6H14
Heptane C7H16
Octane C8H18
Nonane C9H20
Decane C10H22

13. Isomer’s Included in the Alkanes and Alkenes. Branched Chains
Indicated by
iso-Hexane, or
i-Hexane
Same Chemical formula different molecular shape.
Different Properties.
The Larger the Chain, the more isomers it can have.
Isomers are paraffins and have the same chemically formula as a normal, these are referred to as iso-butane or iC4
The molecular structure change, changes all physical properties of the molecule.

14. Naphthenes Cyclo-paraffin’s May have one ring or several combined.
Different Chemical Formula from straight chained paraffin.
CnC2n
Ringed Saturated hydrocarbons
May have one ring or several combined.
Different properties than straight chains or isomers of the same Carbon content.

15. Alkenes Straight or Branched Chains Unsaturated Hydrocarbons
Double bonded hydrocarbons.
Ending in –ene
Referred to Olefins
Chemical symbols
CnH2n. For 1 double bond
Diolefins
2 double bonds
Unsaturated Hydrocarbons
Are lacking some hydrogen due to double bonds.
Formed in refinery in cracking without the presence of hydrogen.
Break down readily in treating reactors

16. Alkynes Triple bonded hydrocarbons Ending in –yne Chemical symbols
CnH2n-2 For 1 triple bond.
Unsaturated hydrocarbons
Lacking hydrogen due to triple bonds
Triple bond is slightly stronger than double bond
Formed in the same way as Alkenes
Break down readily in treating reactors

17. Aromatics Base is benzene ring Can have sub groups Common names PNA’s
Cyclo-alkene
Can have sub groups
Methyl, Ethyl
Common names
Benzene
Toluene
Xylene
PNA’s
Polynuclear aromatics
Two or more benzene rings
Environmentally un-friendly

18. Impurities Sulfides Mercaptans (Thiols) Phenols Pyroles
R-S-R
Mercaptans (Thiols)
R-SH
Ethyl mercaptan added to Natural gas
Skunk odor.
Phenols
Alcohol like molecules
Pyroles
Nitrogen compounds found in crude.
Bottom Sediment and Water.
BS&W
Discuss mainly Sulfides and mecaptans, the chemical structure is on the test. RSH and RSR should be emphasized.

19. From Crude to your car. Separating the good from the ugly.
Distillation
Removing impurities
Catalytic processes
Blending
Refined Products

20. Compounds in Crude Each Compound has different physical properties.
These properties are used in the separation or distillation process.
Mainly based on boiling point
Crude oil is separated into other mixtures.
LPG
Gasoline
Jet Fuel
Diesel
Gas oils
Resid and/or coke.

21. Viscosity Measurement of thickness of a liquid.
How easily it pours or flows
The heavier the material the higher the viscosity (usually)
Test method for diesel, jet, and lube oils.

22. Vapor Pressure and Flash point
Referred to as RVP (Reid Vapor Pressure)
Equilibrium of liquid and vapor in a closed atmosphere.
The lighter the material the higher the vapor pressure. More volatile.
Flash point – temperature which compound will ignite.
Volatility.
Flash point, Volatility are test questions as well, need to emphasize how they relate to light and heavy hydrocarbons.

23. Hydrocarbon
BP °F
Product Range
Methane - C
-258
Natural Gas
Octane-C8
258
Gasoline
Ethane – C2
-127
Nonane-C9
304
Gasoline/
Distillate
Propane – C3
-43
LPG
Decane-C10
345
iso-Butane – C4 11
Undecane-C11
385
n-Butane – C4 31
LPG/ Gasoline
Dodecane-C12
421
Pentane – C5
96.8
Tridecane-C13
456
Hexane – C6
155
Octadecane-C18
601
Benzene – C6
176
Eicosane-C20
651
Distillate/
Gas oil
Cyclohexane – C6
177
Gas Oils-C20+ °F
Heptane-C7
209

24. Boiling Ranges Note percentage overlaps: 40% of Huk is Jet
1st Frac ovhd 20-25% jet in it that is sent out as HUK, maybe some jet give away. Depends on tank farm needs and product value.
10% roughly of hot drum material is LUK – To much cold reflux to hot reflux ratio? Future slide shows correlation between hot drum outlet TI and cold drum FBP.
Only a 5% or less overlap between 2nd ovhd and jet, good separation. 1st stage overhead has 20-25% overlap with jet fuel, reducing ovhd 95% point can increase jet production.
Jet flash of 140 = 296 F IBP ± 4
Jet Freeze –56 = 600 F FBP
2nd Stage overhead is 60% LUK material, activity on R4?
Notice that NO LUK material is being sent over from first stage fractionation. All LUK product in second stage is being produce by R4 reactor. The 1st stage bottoms material does should not contribute to the top ΔP, all is jet fuel.
1st Stage frac bottoms is as expected roughly 50% jet fuel.
RCO has 5-8% jet in it, keeping reboiler at max. temperature and tower pressure at a minimum aids in removing the jet material.

25. Boiling Points What is IBP What is FBP Initial boiling point
Final boiling point
IBP is on the test,

26. Distillation
Physically separating compounds from a mixture based on boiling points.
Each compound in the mixture has a different boiling point.
Distillation is on the test relating to separation based on boiling points.

27. Fractionation Simple distillation fine tuned.
The taller the tower and more trays adds in separation.
Debutanizer
Removes Butane and lighter
Dehexanizer/Splitter
Removes Hexane and lighter.

28. Natural Gas Natural Gas Contains mainly Methane and Ethane
Referred to as
C1 Methane
C2 Ethane
Found with crude oil but removed at the sight.
Low heat energy

29. LPG Liquefied Petroleum Gas. In crude oil
Propane (C3)
Butane (C4)
In crude oil
Produced from refinery processes
Sold as product
Butane can be used in gasoline blending.
Low heat energy

30. Gasoline Gasoline Contains
Pentane (C5)
Hexane (C6)
Heptane (C7)
Octane (C8)
Nonane (C9)
Gasoline boil in the range of 55 to 400 degrees Fahrenheit.
More heat energy than LPG

31. Jet Fuel and Diesel Jet fuel and Diesel are group as Distillates
Jet fuel boil in the range of 200 to 550 degrees
Heat energy higher than gasoline
Diesel, at about degrees.
Higher heat energy

32. Gas oils and Resid. Heavy oils - C14 and larger Can be used as
Bunker Fuel
Feed Stocks to Cracking units and Coker.
Asphault
Gas oils boil in the range of 600 –1100 degrees.
Greatest heat energy

33. Hydrogen Plant Main producer of Hydrogen for the Hydrocracker.
High Purity Hydrogen.
By-products are CO and CO2
CO2 Sold as product
Steam Reforming Process

34. Hydrotreating Catalytically removes impurities.
Mostly Sulfur and Nitrogen.
Consumes Hydrogen
Produces H2S and NH3
Fuel specifications and environmental concerns.
Makes corrosive salts.

35. Hydrotreating All ranges of products are treated.
NHDS (Naphtha Unit)
Treats Gasoline
DHDS (Diesel Unit)
Treats Diesel
Hydrocracker
Treats Gas oils.
ISOM Unit will also treat gasoline.
Caustic washing will remove light mercaptans and H2S

36. Removing Impurities DEA Plant Sour Water. DEA absorbs H2S Chemically.
Releases it in Regenerators.
H2S is combusted with H2 and air
Elemental Sulfur is removed.
Sour Water.
Water absorbs the Ammonia and H2S
Sour water is stripped Removing the H2S and NH3 gases.
Vapor Recovery

37. Cracking Making usable products from less valuable heavy oils.
Breaking Large molecules in to smaller ones.
Heavy gas oils and Resid are not worth as much as jet and gasoline.
Hydrotreating

38. Hydrocracking Cracking in Controlled Environment.
Catalyst is used to make Reaction Conditions less severe.
Temperature controls rate of reaction.
Broken Bonds are saturated with Hydrogen.
Produces Paraffinic products

39. Coking Thermal cracking. With out the presence of Hydrogen
Heating oil under pressure to cracking temperature.
Quickly reducing pressure in the drums causing hydrocarbons to crack into smaller chains and carbon to solidify
With out the presence of Hydrogen
Produces unsaturated olefins.

40. Reforming
Reformulates paraffinic material into higher octane molecules.
Aromatics
Isomers
Naphthenes
Breaking the Hydrogen - carbon bond.
Produces Hydrogen as a by-product.
Major Refinery Hydrogen Producer

41. Isomerization Similar to Reforming.
Benzene Saturation – Bensat Reactor.
No Aromatic formation – using isomers for increase in octane of product.
Re-arrange molecular shape.
Straight Chains to Branched Chains.
Increases Octane and RVP.