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Organic Chemistry

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. Covalent Bonds Atoms in a molecule share electrons. Ionic Bonds One atom gives up an electron to the other.

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Organic Chemistry

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  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.

  2. Covalent 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. Bonding

  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 Carbon - 84% Hydrogen - 14% Sulfur - 1 to 3% Nitrogen - less than 1% Oxygen - less than 1% Metals - less than 1% Salts - less than 1% BS&W

  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

  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

  8. 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.

  9. 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

  10. 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 Alkanes

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

  12. 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. Isomer’s

  13. Cyclo-paraffin’s 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. Naphthenes

  14. Straight or Branched Chains 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 Alkenes

  15. 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 Alkynes

  16. Base is benzene ring 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 Aromatics

  17. Sulfides 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 Impurities

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

  19. 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. Compounds in Crude

  20. 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.

  21. 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.

  22. Boiling Ranges

  23. What is IBP Initial boiling point What is FBP Final boiling point Boiling Points

  24. Distillation • Physically separating compounds from a mixture based on boiling points. • Each compound in the mixture has a different boiling point.

  25. 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.

  26. 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

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

  28. 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

  29. 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 300-700 degrees. • Higher heat energy

  30. 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

  31. 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

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

  33. 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 Hydrotreating

  34. DEA Plant 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 Removing Impurities

  35. 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

  36. 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

  37. Coking • Thermal cracking. • 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.

  38. 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

  39. 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.

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