Chapter 1 fats and oils

• Oleochemistry


  The study of vegetable oils, animal oils and fats, and oleochemicals derived from these fats and oils
• Oleochemicals


  Chemicals derived from fats and oils
• Lipids


  A family of compounds that includes Triglycerides (fats & oils), Phospholipids, Sterols (cholesterol), Sphingosine
• Fats


  Lipids that are solid at room temperature
• Oils


  Lipids that are liquid at room temperature
• Sphingosine


  An 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids, a class of cell membrane lipids that include sphingomyelin, an important phospholipid
• Classification of lipids


  • Simple lipids
  • Complex lipids
• Simple lipids


  Lipids composed of fatty acids and alcohols, with no other substance
• Complex lipids


  Lipids that contain three or more chemical components
• Examples of complex lipids

  • Phospholipids
  • Glycolipids
  • Sphingolipids
  • Nucleolipids
• Structural moieties of lipids

  • Glyceryl esters (esters of glycerol and fatty acids)
  • Cholesteryl esters (esters of cholesterol and fatty acids)
  • Waxes (esters of long-chain alcohols and fatty acids)
  • Ceramides (amides of fatty acids with long-chain di- or trihydroxy bases)
• Sources of oils and fats

  • Animal fats (Tallow, Lard, Poultry)
  • Tropical oils (Palm kernel oil, Coconut oil, Palm oil)
  • Soft oils (Soya oil, Sunflower oil, Rape oil, Canola oil, Corn oil)
• Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides.
• Lard is a semi-solid white fat product obtained by rendering the fatty tissue of a pig.
• Malaysian Export of Oleochemical, 2016
• Global trends in oils and fats

  • Individual consumption continues to increase
  • A move away from animal fats to vegetable oils
  • Replacement of previously established fats and oils with different source oils
  • Introduction of new vegetable oils
  • The rise and fall of some individual source oils
  • Source oil changes that reflect the results of medical studies
  • Introduction of genetically modified oil seed varieties
• Polyols


  Hydroxyl-functionalized oligomers having a molecular weight in the range of 300–9000 g mole−1 and functionality in the range of 1–8 equivalent per mole
• Ricinoleic acid from castor oil
• Palm oil, being a triglyceride, does not possess any free hydroxyl groups in its original form. Therefore, the hydroxyl groups are introduced into the triglycerides via a chemical process (manipulations of double bonds and carbonyl groups).
• Main components of fats and oils

  • Triglycerides (97-98%)
  • Nonglycerides (2%)
• Minor components of fats and oils

  • Phospholipids
  • Tocopherols & tocotrienols
  • Sequalene
  • Sterols
  • Pigments
  • Pesticides
  • Trace metals
• Typical composition in fatty acids of the rapeseed oil
• Average Fatty Acid Composition of Some Common Fats and Oils (%)
• Monoglyceride


  1. monopalmitin, 1-monoacylglycerol
• Diglyceride


  1,3-diacylglyceride, 1-oleoyl-3-palmitin, 1,3-diacylglycerol
• Triglyceride


  1. palmitoyl-2-oleoyl-3-stearin, triacylglycerol
• Examples of homotriglycerides


  • Stearin (derived from stearic acid)
  • Palmitin (derived from palmitic acid)
  • Olein (derived from oleic acid)
• Example of a triglyceride derived from one molecule each of palmitic acid, oleic acid, and stearic acid, the three most abundant fatty acids in the biological world.
• Physical properties of oils and fats

  Pure fats and oils are colorless, odorless, and tasteless. The characteristic colors, odors, and flavors are imparted by foreign substances that are lipid soluble and have been absorbed by these lipids.
• Physical properties of oils and fats

  • Viscosity
  • Density
  • Surface and interface Tension
• Chemical properties of oils and fats

  • Undergoes various chemical reactions
  • Hydrolysis
  • Esterification
  • Ester Exchange
• Triglycerides


  Molecules composed of three fatty acids arranged on a glycerol molecule, with variations in chain length and degree of saturation of the fatty acids
• Triglycerides


  • Triglyceride derived from one molecule each of palmitic acid, oleic acid, and stearic acid, the three most abundant fatty acids in the biological world
• Pure fats and oils

  • Colorless, odorless, and tasteless
  • Characteristic colors, odors, and flavors are imparted by foreign substances that are lipid soluble and have been absorbed by these lipids
• Butter


  • Yellow color due to the presence of the pigment carotene
  • Taste comes from two compounds—diacetyl and 3-hydroxy-2-butanone—produced by bacteria in the ripening cream from which the butter is made
• Physical properties of oils and fats

  • Viscosity
  • Density
  • Surface and interface Tension
• Chemical properties of oils and fats

  • Undergoes various chemical reactions
  • Hydrolysis
  • Esterification
  • Ester Exchange Reaction
• Hydrolysis


  1. Hydrolysis of the triglycerides in the oils and fats will produce free fatty acid and glycerol

  2. Reaction can be catalyzed by Chemical catalyst

  3. Enzymes

  4. Fungi (release lipase)
• Esterification


  Fatty acids are converted to esters by reaction with an excess of alcohol using an acid catalyst or a lipase
• Ester Exchange Reaction


  1. The fatty acid or alcohol groups present in an ester can be exchanged in a number of ways: by reaction with an excess of other fatty acids (acidolysis), alcohols (alcoholysis), or other esters (interesterification)

  2. Generally, the starting point will be a triacylglycerol, and these reactions provide routes by which the composition and properties of oils and fats can be modified