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Cognis College

Fatty acids


F32 Fatty acids

1. Occurrence of the fatty acids 2. Chemical structure 3. Properties of the fatty acids 4. Reference numbers of the fatty acids 5. Extraction of the fatty acids 6. Technical variations and specialties 7. Application areas 8. Market data 9. Trade Names at Cognis 10. 21 3 4 7 8 9 13 17 18 20 Keywords

F32 Fatty acids 3 .

1 c R Structure of the fatty acids The percentage of fatty acids in the oils and fats is different from resource to resource.4 F32 Fatty acids Chapter 1 Occurrence of the fatty acids Fatty acids are a component of the natural oils and fats. 2 8 4 7 5 48 50 17 15 4 2 9 7 30 42 2 4 6 8 10 18 65 56 38 90 93 91 7 2 1 50 3 C-chain distribution in natural oils and fats . Coconuts or palm kernels deliver mainly C12 / C14. They are esterified with glycerine and form triglycerides. The most important fatty acids in oleochemicals are found in the following natural oils and fats: C-chain distribution and quantity C8 C10 C12 C14 C16 C18 C20 C22 coconut palm kernel tallow palm oil rape rich poor sunflower soya Fig.. tallow or palm oil mainly C16 / C18. glycerine part H2 fatty acid part o c c c o o o c o R H c o R H2 Fig. for example.

F32 Fatty acids 5 Chapter 2 Chemical structure Fatty acids belong to the chemical group of the carboxylic acids. Saturated fatty acids contain only single bonds (C-C) in their hydrocarbon chain. the carboxylic acids are called fatty acids. C12 H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H O C O H carbon chain Fig. 3 O R C O H O C O H O C O H Structure of the carboxylic acids The chemical name "carboxylic acid" is derived from the basic hydrocarbon to which the addition "acid" is connected to. This is due to the elongation process that takes place in plants. The carboxylic group is responsible for the acidic effect of these substances. A difference is made between saturated and unsaturated fatty acids. 4 Structure of the lauric acid acid group From the number of 4 carbon atoms in the hydrocarbon chain on. The following table shows a carboxylic acid that is very important in oleochemicals: lauric acid. carboxylic acids carboxylic group: consists carbonyl of group: hydroxyl Fig. . because it is able to set free a hydrogen ion (H +) when solved in water. The carboxylic acids are characterized by a carboxylic (or carboxo) group (COOH) that is attached to a hydrocarbon chain (abbreviated R). Fatty acids from natural oils or fats are always even-chained and have got an even number of carbon atoms.

The dodecanoic acid for example was first found in the fruits of the laurel tree (Latin: Laurus nobilis) and was thus called lauric acid. saturated stearic acid (octadecanoic acid) C17 H35 COOH H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H O C O H C 18 fatty acid. The most important fatty acids are the following: Saturated fatty acids C6 C8 C 10 C 12 C 14 C 16 C 18 Hexanoic acid Octanoic acid Decanoic acid Dodecanoic acid Tetradecanoic acid Hexadecanoic acid Octadecanoic acid Caproic acid Caprylic acid Caprinic acid Lauric acid Myristic acid Palmitic acid Stearic acid . These names were introduced most often with the discovery of the fatty acids. If more than one double bond exists. In the oleochemical terminology still the trivial names are most often used. triple etc.) unsaturated fatty acids. Here are examples of the C18 fatty acids (fatty acids with 18 carbon atoms): C 18 fatty acid. they are called multiple (double. double unsaturated linoleic acid (octadecadienoic acid) C17 H31 COOH H H C H H C H H C H H C H H C H H C H C H C H H C H C H C H H C H H C H H C H H C H H C H H C H O C O H C 18 fatty acid. 5 C 18-fatty acids Apart from the chemical names there exist so-called trivial names of the fatty acids as well.6 F32 Fatty acids Unsaturated fatty acids contain at least one double bond in their hydrocarbon chain (C=C). single unsaturated oleic acid (octadecenoic acid) C17 H33 COOH H H C H H C H H C H H C H H C H H C H H C H H C H H C H C H C H H C H H C H H C H H C H H C H H C H O C O H C 18 fatty acid. triple unsaturated linolenic acid (octadecatrienoic acid) H H C H H C H H C H C H C H H C H C H C H C17 H29 COOH H C H C H C H H C H H C H H C H H C H H C H H C H O C O H Fig.

Castor oil contains 87 % of the ricinoleic acid that has the chemical name 12-OxyOctadecenic acid.F32 Fatty acids 7 C 20 C 22 C 24 Eicosanoic acid Docosanoic acid Tetracosanoic acid Arachidic acid Behenic acid Lignoceroic acid Unsaturated fatty acids (number of double bonds /.) C 18 / 1 C 18 / 2 C 18 / 3 C 20 / 1 C 20 / 4 C 22 / 1 C 22 / 5 Octadecenic acid Octadecadienoic acid Octadecatrienoic acid Eicosenoic acid Eicosatetraenoic acid Docosenoic acid Docosapentanoic acid Oleic acid Linoleic acid Linolenic acid Gadoniloic acid Arachidic acid Erucic acid Clupanodonic acid The ricinoleic acid is in a special position. It is a single unsaturated fatty acid that attaches a hydroxyl group (OH) to a C-atom. Ricinoleic acid H H C H H C H H C H H C H H C H H C H H O C H H C H H C H C H C H H C H H C H H C H H C H H C H H C H O C O H C17 H32 OH COOH Fig. 6 Structure of the ricinoleic acid To this additional hydroxyl group one can add for example ethylene oxide to get an emulsifier such as Eumulgin RO40. .

8 length C6 C8 C10 C12 C14 C16 C18 C18/1 C22/1 C18/2 C18/3 Mp/°C 4 17 31 43 54 63 71 16 34 -5 -11 Bp/°C/mbar 101/1013 239/1013 270/1013 225/133 250/133 272/133 291/133 229/20 225/13 230/21 232/23 Boiling points of the fatty acids The viscosity of the fatty acids rises as well with the increasing chain length and falls with the increasing number of double bonds.).g. 7 length C6 C8 C10 C12 C14 C16 C18 C18/1 C22/1 C18/2 C18/3 Titer/°C -3. Their melting point rises with the increasing chain length.3 43. By the raising of number of double bonds the boiling point decreases again. The solubility gets worse with the increasing chain length. gasoline etc. the short chain fatty acids have an advantage over the long chain. but a higher temperature can compensate this. For some boiling points (Bp) one has to lower the pressure and get degrees of centigrade in vacuum. Fatty acids are soluble in organic solvents (e.7 -5. Water and fatty acids are only hardly soluble at room temperature. In the oleo chemistry the solidification point (called Titer with fatty acids) is indicated which is usually a little lower than the melting point.0 -11 mp/°C 4 17 31 43 54 63 71 16 34 -5 -11 Solidification points of the fatty acids Even the boiling points increase with the rising chain length.4 62.6 13. . the unsaturated fatty acids have got a lower melting point (mp) than the saturated ones.5 54. Therefore the figures /mbar are added.4 34. Otherwise the acids are cracked before they can reach the boiling points.4 16 31. Not every acid can be measured at usual atmospherically pressure (1013 mbar). fatty acids capronic acid caprylic acid capric acid lauric acid myristic acid palmitic acid stearic acid oleic acid erucic acid linoleic acid linolenic acid Fig.8 F32 Fatty acids Chapter 3 Properties of the fatty acids Pure fatty acids are colorless substances.9 69. alcohol. fatty acid capronic acid caprylic acid Capric acid lauric acid myristic acid palmitic acid stearic acid oleic acid erucic acid linoleic acid linolenic acid Fig.

Since no 100 % clean fatty acid from natural oils and fats exists and since many products contain a mixture of fatty acids depending on the raw material (e. Fig. The acid value (DGF C-V 2) indicates the amount of free fatty acids. The iodine value indicates the amount of unsaturated components. 2) is measured after DGF C-VI 10 with the help of the gas chromatography or other chromatographically methods (such as HPLC). the more double bonds.g.5 to 2 % with technical fatty acids. The higher the iodine value. This C-chain spectrum (see Fig. coconut oil fatty acid) it is important to indicate the distribution of the C-chains in percent. 10 Overview of titration numbers . hydrocarbons etc. ACID VALUE: AV ESTER VALUE: EV SV .AV = EV The content of unsaponifiable material (e. It indicates the amount of mg KOH that are necessary to saponify 1 g of the substance. -> inner esters Definition: EN indicates how many mg KOH are necessary for the saponification of the esters in 1g of fat / oil. SAPONIFICATION VALUE: SV -> free fatty acids -> fatty acids bound to glycerine Definition: SV indicates how many mg KOH are necessary for the saponification of 1g fat / oil.F32 Fatty acids 9 Chapter 4 Reference numbers of the fatty acids The reference numbers of the fatty acids are part of the quality specification. -> free fatty acids Definition: AV indicates how many mg KOH are necessary to neutralize the free fatty acids in 1g of fat / oil.) is another indicator for the quality and is about 0. Most often the measuring of the bromide value is carried out after Kaufmann (DGF C-V 11 d). entry of sample separator tube Fig. The saponification value (DGF C-V 3) is a measure for the free and bound fatty acids in the test substance. As a physical parameter the solidification point (also called Titer) is important. measured in mg KOH.g. sterines. They are measured after the instructions of the ”Deutschen Gesellschaft für Fettchemie” (DGF) (German Society for Oleo chemistry) and they allow a clear characterization of the products. It indicates the temperature in °C at which a liquid fatty acid reaches its maximum solidification (DGF C-IV 3 c). vitamins. 9 recorder detector Schematic drawing of a gas chromatograph Apart from the C-chain distribution a couple of other chemical and physical parameters are measured that serve the purity control of technical fatty acids. that are necessary to neutralize 1g of the test substance.

Here only one general note: The clearer the starting material the higher the quality of our products: Each reaction or subsequent treatment goes hand in hand with a thermo or mechanical strain.IR range Fig. TINTOMETRY: Comparison with coloured glasses LOVIBOND dye value GARDNER dye value 2.UV range . Partly these raw materials have to be pre-cleaned in order to remove carbohydrates. . The chemical base for this process is the dissolving of the ester bond by the addition of water. either by the comparison with color glasses after Lovibond 5 1/4” (DGF CIV 4 b) or after Gardner (DGF C-IV 4 c) or by the comparison with color solutions after Hazen (also called APHA dye value) (DIN 53409). PHOTOMETRY: Measuring of the absorption degree Principle: reflection / absorption in . (DGF D-III 3). Glycerine and fatty acids are the result. These fatty acids (raffination fatty acids or soap stock fatty acids) get into the technical further treatment. 1. also the color measuring is used. phosphatides and other impurities. In order to check the quality of the technical fatty acids. In this way components that cause a change of color can be indicated. the cloud point is indicated instead. Chapter 5 Extraction of the fatty acids Cognis extracts fatty acids from natural oils and fats. sterines. 11 Overview of dye values All these parameters are dealt with in detail in the course K11 ("Physical and chemical data for Oleochemicals") and the accompanying brochure. Especially with the treatment of oils and fats for purposes of nutrition the cleaning (raffination) is carried out thoroughly. at which a cooled and solidifying fatty acid becomes perceptibly cloudy.10 F32 Fatty acids With low melting fatty acids that do not have a solidification point that is easy to indicate. COLOMETRY: Comparison with coloured solutions Hazen dye value APHA dye value 3. proteines. In this process also the so-called free fatty acids (not bound to glycerine) are removed. That means the temperature in °C. The main part of the fatty acids for the oleo chemistry is extracted by the hydrolytic fat splitting.visible light .

Because these alkaline catalysts form soaps during the splitting process that are solved in the produced split fatty acid. 12 Hydrolytic fat splitting In this process water is added continually to the oils and fats at a temperature of up to 260 °C and a pressure up to 60 bars. CaO) the reaction speed can be risen. MgO. oils/fats water let-down vessel steam autoclave split fatty acid glycerine water Fig.F32 Fatty acids 11 triglyceride H H C O O C O H C O C O H C H O C R 3 + water glycerine + H fatty acid O R 1 H O H H C O H R 1 C O O H R 2 H O H H C O H R 2 C O O H H O H H C H O H R 3 C O H Fig. In the reaction vessels two phases are found during the splitting process: An aqueous phase that consists of water and glycerine and a fatty phase that consists of fat and fatty acids. Another method to extract fatty acids from natural oils and fats is the saponification of these raw materials. triglyceride H H C O O C O H C O C O H C H O C R3 K O H H C H O H R3 R 2 + KOH glycerine H + potassium soap O 1 R 1 K O H H C O H R C O O K K O H H C O H R 2 C O C O K O K Fig. At the pressure less splitting at a temperature of 100 °C acid catalysts (aromatic sulfonic acids in combination with sulfuric acid) are applied to rise the speed of the reaction. Potash lye (KOH) is added to the oils and fats and the result is glycerine and potash salts of the fatty acids (so-called potassium soap). 14 Saponification of the oils and fats with potash lye . it is necessary to acidify thereafter in order to replace the soaps. 13 Process of the hydrolytic fat splitting By the addition of alkaline catalysts (ZnO. The split fatty acids and the glycerine water are removed continually.

from hardened palm oil fatty acid about 2 % of myristic acid (C 14). C 14. 42 % palmitic acid (C 16) and 50 % stearic acid (C 18). In order to separate the natural fatty acid mixes in the fatty acids (called fractions or cuts) different methods are applied: a) Fractionated distillation The fractionated distillation is based on the different boiling points of the fatty acids.and capric acid results and lauric acid in the second column. The raw fatty acids produced this way still contain residues and unsplitted fatty acid glycerides (mono. The differences in boiling temperature between the fatty acids with the same chain length are too little to get clean fractions without this modification. This is why the split fatty acids are distilled for cleaning purposes. from palm oil: A mixture from stearic acid. the unsaturated components have at first be changed to saturated ones (see chapter 6: Technical variations). In order to keep the unsaturated parts. 15 Extraction of fatty acids from potassium soaps This method is only applied with castor oil today. Cognis developed the so-called transwetting method that is explained in the following: b) Fractionated crystallization The method of the fractionated crystallization is based on the different melting points of the fatty acids and on the fact that melted fatty acids form crystals when they cool down and slowly get solid again.g. even-numbered fatty acids. If it is intended to split up a fatty acid mixture with the same chain length but with different degrees of saturation (e. because the OH-group of the ricinoleic acid would be destroyed during the splitting process with water (hydrolytic fat splitting).g. hydrochloric + potassium acid soap O H Cl R C O K K Cl R potassium chloride + fatty acid O C O H Fig.and diglycerides). Thus one gets the so-called distillate fatty acid. The differences are 15 . It is a fatty acid mix that corresponds in its composition to the fatty acid that is esterified in the starting raw oil or -fat. Significantly different are the melting points between the saturated fatty acids (palmitic and stearic acid) and the unsaturated ones (oleic acid) in the tallow fatty . With a fractionated distillation of a fatty acid mix from coconut oil in the first distillation column a mix of caprylic. By the fractionated distillation one gets e.12 F32 Fatty acids Thereafter hydrochloric acid is acidified: Fatty acids and potassium chloride are the result. In a further distillation with higher temperatures one gets the higherboiling fatty acids. so an extraction of single fatty acid chains is possible up to a purity of 99 %.and palmitic acid). oleic acid and linoleic acid with myristic.30 °C with successive.

because the fatty acid crystals are now wetted by the water and not. The liquid oleic acid is distributed in the water as small droplets (emulsion). The saturated components have a higher melting point and thus crystallize first when the melted substance cools down. by the liquid fatty acids.g.g. By centrifugation (quick spinning) the two phases are separated. The paraffine oxidation is only of significance in the Eastern European countries and in China. A wetting agent is a substance that causes an adherence of water (wetting) at the surface of a solid material (e. The fatty acids extracted this way may also have branched chains and can be of an uneven number.g.g. fatty alcohol sulfate). Synthetic fatty acids In petrochemicals fatty acids can also be produced by the oxidation of paraffines (alkanes). as before. oleic acid) stearic acid oleic acid 2. stearic acid) are finely distributed in liquid fatty acid (e. of a crystal). The parts of the two-phase-mixture can be separated easier than by pressing if a wetting agent solved in water is added to the mix. The synthetic fatty acids form only a small part of the production of even-chained. Fatty acid crystals (e. . The liquid components could thus run off through the clothes. a solvent process is used instead of water with a wetting agent.g. 16 Transwetting with the fractionated crystallization Within Cognis Corp. E. The water together with the wetting agent keeps the liquid fatty acids away from the direct surroundings of the solid fatty acid crystals. Addition of water + wetting agent (e.F32 Fatty acids 13 acid. The result is a mixture of emulsion (water/liquid fatty acid crystals) and a suspension (water/solid fatty acids) that can easily be separated by centrifugation (fast spinning). fatty alcohol sulfates can be used as wetting agents. The stearic acid crystals are no longer wetted by the oleic acid. Thereafter only the water has to be removed. but by water (suspension). This process is called rewetting. 1. In a certain temperature range two phases are found: A liquid one (mainly unsaturated fatty acids) and a solid one in form of crystals (mainly saturated fatty acids). Pressing in former times carried out the separation of these phases: The two-phasemixture was wrapped in cloth and a pressure was exerted by hydraulic presses. Fig. Cognis developed this rewetting procedure. oleic acid water stearic acid 3. even-numbered fatty acids.

. This liquid product is made from beef tallow. Nowadays the stearines are also extracted from hardened palm oil-. type coconut/palm kernel) or they are sold as single fatty acids with different degrees of cleanness by the name of "fractionated fatty acids" (e. caproic acid above 99%). By the hardening (hydrogenation) the C-chain spectrum of fatty acid mixes changes that make them easier to split up.. fatty acids can either completely or only partly are hardened. distribution of the c-chains soya oil fatty acids C16 C18 C18/1 C18/2 C18/3 C20 8 4 28 53 6 1 partial hydrogenation complete hydrogenation Fig. more color stable and less sensitive to oxidation..g.e.. but also from vegetable oils as palm kernel oil. 18 8 46 40 5 -- 1 8 91 -- -- -- 1 Even the properties of the fatty acids change with the hardening. Fig.g. this is transformed into a single bond..and rape oil fatty acids. Hardened fatty acids are of a lighter color. C H . ”Oleine” is the technical term for the oleic acid (C 18/1). fish oil. they Change of the c-chain distribution by fat hardening . 17 Fat hardening (hydrogenation) Depending on the desired degree of saturation. the addition of hydrogen can be dosed. By the name ”stearine” a mix of palmitic acid (C 16) and stearic acid (C 18) is meant. C H . i. + H H H H C H H C H H C H C H C H .. palm oil and linseed oil (partly hardened). In former times this solid fatty acid mixture was made mainly from beef tallow. In this way. This procedure is called fat hardening or hydrogenation.. One example of the technical variations of fatty acids is the transformation of unsaturated components into saturated ones.14 F32 Fatty acids Chapter 6 Technical variations and specialties The fatty acids extracted in this way are either sold as "distilled fatty acids" according to the basic oils or fats (e.. H H C H C H C H C H C H . By the attachment of hydrogen to a double bond.

Octadecatrien acid H H C H H C H H C H H C H H C H C H C H C H C H C H C H H C H H C H H C H H C H H C H H C H O C O H 13 Fig. 20 melting point: 44. 19 11 9 9.13 .Octadecatrien acid Conjugation of linolenic acid This shift of the double bonds is achieved with the help of special alkaline catalysts at temperatures of about 200 to 300 °C and an appropriate pressure at the step of saponification and following deacetylation.15 . that is why they are used e. The conjugated fatty acids react faster and get easier linked with each other. i. which then are hardened to the right consistency.g. For margarine. Natural unsaturated fatty acids have often got a cis-configuration. In the single unsaturated C 18-fatty acid the oleic acid (chemical name: cis-octradecenic acid) has got a melting point of 16. whereas the iodine value falls. Cis-trans-isomerization . but in which the number and kind of atoms remain the same are called isomerizations (Greek: isos: same. meros: part). With the help of catalysts (e. the two hydrocarbon atoms at the double bond are on the opposite of each other. With the advanced hardening the solidification point (Titer) rises.12. H H C H H C H H C H C H C H H C H C H C H H C H C H C H H C H H C H H C H H C H H C H H C H O C O H 15 12 9 9.3 °C.3°C H C H H C H H C H H C H O C O H C17 H35 COOH H H C H H C H H C H H C H H C H H C H H C H H C H H C C H H C H H C H H C H H C H H C H H C H H C H O C O H elaidic acid trans-configuration Fig. oleic acid H H C H H C H H C H H C H H C H H C H H C H Cis-configuration H C H H C H C H C H H C H H C H melting point: 16.5°C By this cis-trans-isomerization the fatty acid changes its physical properties. as an example.5 °C. Aside from the conjugation another type of isomerization can be carried out with fatty acids. often-liquid vegetable oils are used. Reactions in which only the arrangement of the single atoms is changed.11. whereas the elaidic acid (chemical name: trans-octadecenic acid) has got a melting point of 44.F32 Fatty acids 15 are easier to store. Multiple unsaturated fatty acids can also be modified in another way: by conjugation.e. After this technical operation the double bonds that were in a long distance from each other are now accumulated and only separated by a single bond. selenium) the unsaturated fatty acids are transformed into the trans-configuration i.e. in the production of polyurethane foams. two hydrogen atoms at the double bond show in the same direction.g.

They result from the fusion of two single fatty acids and have thus the double number of carbon atoms. They have three times as many carbon atoms as the basic fatty acids and three carboxylic groups. 22 Dimerization of oleic acid At the dimerisation that is carried out with special catalysts at temperatures between 180° and 300 °C. saturated.16 F32 Fatty acids Another type of isomerisation is the production of iso-stearic acids. Dimer fatty acids are dicarbonic acids. which leads to a branching of the hydrocarbon chain.e. fatty acids that have two carboxylic groups (see chapter 2). apart from the dimer fatty acids and the iso-stearic acids also trimer fatty acids result. high molecular weight Dimer fatty acid Trimer fatty acid Applications: lubricants. After this the double bond is transferred into a single bond with the help of hydrogen. Other specialities that can be made of fatty acids are the azelaic acid (chem. stearic acid H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H H C H O C O H C17 H35 COOH H H C H H C H H C H H C H H C H H C H H C H H C H H C C C H H C H C H H H H H C H H C H H C H H C H O C O H iso-stearic acid H H Fig. dimer acid ethoxylates. name: nonanoylic acid (C 9): . cosmetics. oxidation stable liquid. i. tall oil fatty acids/oleic acid Monomer fatty acid Isostearic acid liquid. 260°C Fig. 21 Isomerization of stearic acid The iso-stearic acids are a by-product of the dimerization of oleic acid. The carbon chain of the dimer fatty acids can have a branched or a ring-shaped structure. cooling lubricant Parameters: pure clay. In this process oleic acid (C 18/1) is treated with catalysts and high temperatures.

by hardening (transition from the double bond into a single bond by the attachment of hydrogen) a 12-oxy-octadecene acid becomes a 12-oxy-octadecane acid. _ H O H H H C H C H Fig.g.F32 Fatty acids 17 O H O C H C H H C H H C H H C H H C H H C H H C H O C O H Fig 23 Structure of the azelaic acid and the pelargonic acid (chem. also called 12-oxy-stearic acid or hardened ricinoleic acid. Also the ricinoleic acid (chem. from the 12-oxy-octadecenic acid an octadecadienoic acid is made that belongs to the conjugated fatty acids..e.. peanut.... 25 H C H C H .. Chapter 7 Application areas The distilled fatty acids based on coconut oil. Dehydration In this way. C H . E. name: nonanic acid C 9) H H C H H C H H C H H C H H C H H C H H C H H C H O C O H Fig. C H C . palm kernel oil. i.. H H O C H H C H H C H C H C H . . Another technical variation is the dehydration. name: 12-oxy-octadecene acid) offers possibilities for modification because of its hydroxyl group (OH) at the 12th carbon atom (see page 6). 24 Structure of the pelargonic acid The production of these ozone acids is carried out by the effect of oxygen (O) on the double bonds of the oleic acid (C 18/1): The hydrocarbon chain of the oleic acid is split up and two C 9-fatty acids result.. a separation of water. palm oil and tallow fatty acid and the multiple unsaturated fatty acids based on cotton.

g.g. From stearines (mixture of palmitic acid C 16 and stearic acid C 18) e. after refinement processes as soap for shaving foams. C 12 fatty acids are used e. after further treatment as emulsifiers and starters at the production of PVC and as surfactants in detergents and cleaners. By the processing to yield alkyd resin they are used in the varnish and color industry. hair dyeing products. as a special cleaning agent and as raw material for detergents and cleaners. in fusion adhesives.g. The conjugated fatty acids are often used as raw material for the production of polyurethane foam.and nutrition industry. C 18 fatty acids are applied to inhibit the depositing of solid components e. basic material for the production of fabric vitamins in animal feed and as lubricating agent. . From oleines (technical oleic acid C 18/1) e. humectants and separating agents in the nutrition industry.g. From fatty acids furthermore fatty amines and amides are produced as PVC-lubricating agents. defoaming soaps in detergents and polishing pastes. soft soaps. in fertilizers. for the surface treatment of tin foils and as a lubricating agent in the metal industry. Erucic acid . flotation auxiliaries for the mining industry and textile auxiliaries are made. auxiliaries for the plastics.g.after esterification .g. By the reaction with lithium-.after neutralization with potash lye or caustic soda . sealing materials and printing inks.10 fatty acids are used as aromatic agents. soya bean and rape seed oil can . With the fractionated fatty acids the application areas can be determined by the chain length: C 6 . vulcanizing catalysts for the rubber industry. fatty acid ethoxylates and partial esters and then they function as emulsifiers or low foaming cleaners. C 16 fatty acids can be applied . Dimer and trimer fatty acids play an important role in the production of polyamides.or calcium oxides one gets metal soaps that are applied as lubricating fats and cold forming agents in the metal and plastics industry. soft soaps.18 F32 Fatty acids sunflower. defoaming agents for the paper. C 22 fatty acids may also be used in the paper industry. They can be refined to yield fatty acid alkanol amides. candles. pesticides. aluminum. lubricating grease. as skin oils in the cosmetic industry. essences. C 14 fatty acids are used e.g. detergent ingredients and deinking agents for the paper industry are made. They are applied e. pharmaceuticals.and rubber industry. cosmetics. in an amidated form as PVC-lubricant or in the production of candles. used (like C 22 saturated) after an amidation in the plastics industry as lubricant in the PVC-production. colors and varnishes or also as chlorides in the paper industry.C 22/1 fatty acid is used for toiletry soaps.

8 mill.713 1.3 mill tons. mt.375 million tons.26 2000 2003 Fatty acid capacities by continents. The utilisation was very low at 4. On these markets a growth is expected.48 million tons in the year 2000. while the need of the textile-. rubberand tire industry is regarded as declining.375 WE Asia America 1. The prognoses for the year 2003 are 6.3 mill.and paper auxiliary markets stagnate. World Fatty Acid Capacities.375 0 effective Capa = 4.682 million tons and North America with 1. In 2000 Asia held the top position with 2.480 6. leather. All in all an annual growth rate of 2 to 3 % is expected. 2000/2003.480 6. Demand ca. ‘000 mt Prognoses are also made for the application areas of the fatty acids. The production of alkyd resins and candles and the application in the color-.085 1. Nowadays most of the fatty acids are used in the production of fatty alcohols.162 4000 3000 2000 1000 World 5.713 million tons. followed by Western Europe with 1. softeners and fragrances.732 3. Chapter 8 Market data Worldwide the capacity for fatty acid was 5. soaps and cosmetics (30-40%). 2000 / 2003.481 1.´000 mt 2000 Capacity 2003 Capacity 7000 6000 5000 5. The application of fatty acids in lubricants is going to increase.F32 Fatty acids 19 In the production of polyamides the azelaic acids are also used. mt Fig.682 2.085 million tons. 3. amides. The azelaic and pelargonic acids can furthermore be processed to yield alkyd resins. The effective capacity is the economic usable value. esters and metal soaps (35-40%) and of detergents. .

Cognis. Akzo and the Acidchem. . Furthermore there are the Hindustan Lever and the company Oleon at the fatty acid market.20 F32 Fatty acids The worldwide biggest four fatty acid producers are Uniqema.

based on tallow are Edenor Edenor Ti types. Conjugated Fatty Acids are Edenor UKD types. Distilled Fatty Acids. Empol 1040 Trimer. Trimer and Polybasic Acids are Empol. i. Also they produce special Fatty Acids. FTi . Cognis Corp. Fractionated Fatty Acids are Edenor types plus the abbreviation of the fraction and the C-chain distribution in percent. Polyunsaturated Fatty acids named are Edenor plus abbreviations. which are explained in chapter 6. This product group is divided into following groups: • • • • • • • Distilled Fatty Acids. The Trade Names for the Dimer. based on coconut or palm kernel oil are Edenor K. Edenor KPK types. uses other Trade Names for Fatty Acids. Oleins are Edenor TiO5 . i. LCU.F32 Fatty acids 21 Chapter 9 Trade Names at Cognis The product name for Fatty Acid at the European and Asian Market is Edenor. Azelaic Acids are Emerox types and the Perlagonic acid is the Emery 1202 type. . Edenor C12 98-100.e.e. Stearines are Edenor ST types or Edenor FHTi types. PK1805 and NSb types. Their product names are divided into following groups: • • • • • • Stearic Acids & Isostearic Acid Oleic & Polyunsaturated Acids Coconut Fatty Acids Tallow Fatty Acids Fractionated Fatty Acids Food Grade Fatty Acids For this product groups they use the Trade Names Emersol and Emery.

Oleine.22 F32 Fatty acids Chapter 10 Keywords The keyword list might be helpful for learning. • • • • • • • • • • • • • • • • • • • • • • • • Sources in nature Ester Triglyceride ”Laurics” Carboxo group Trivial names of fatty acids Peculiarity of the ricinoleic acid ”Physical and chemical data” Chain distribution Saponification value Iodine value Ester value Titration Titer Unsaponified matter Color measurements Fat splitting Saponification of oils and fats Fractionated Distillation/Crystallisation Fat hardening ”Conjugated Double bonds” ”Isomeric structures” Stearine. With adding one sentence or explanation to each word. one will get a good summary of the present topics. Paraffine ”Dehydration” ..