Fundamentals of Oils & Fats by Albert J. Dijkstra, PhD
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1 Fundamentals of ils & Fats by Albert J. Dijkstra, PhD Ignace Debruyne, PhD Fundamentals of Edible il Processing and Refining Saturday, May 3, 2014
2 Topics to be discussed Composition of oils and fats Triglycerides, fatty acids, phosphatides, tocopherols, tocotrienols, phytosterols, coloring compounds Properties of oils and fats Physical, melting point Chemical, oxidation Sources of oils and fats Processing of oils and fats: Refining/modifying Degumming, neutralization, bleaching, deodorization Hydrogenation, interesterification, fractionation 2
3 Composition of oils and fats Saponifiable fraction: around 98% : reacts with alkali under formation of soaps (alkali salts of FA) Unsaponifiable fraction: around 2% : Triglycerides: esters of glycerol with 3 fatty acids (FA) Mono- and diglycerides (partial glycerides) Free fatty acids (FFA) Waxes: esters of fatty acids with fatty alcohols Phospholipids (phosphatides, sphingomyelins) HC Glycolipids Sterol esters CH 2 Tocopherols Free (non-esterified) sterols Hydrocarbons, carotenoïds, squalene, chlorophyll Vitamins Polyphenols: in olive oil xidation products 3 CH 2 C C C R 1 R 2 R 3
4 Nutritional aspects Source of energy (9 kcal/g or 37 kj/g) Source of essential fatty acids (ω-3, ω-6) Fat soluble vitamins (A, D, E) Functional minor components: tocopherols, sterols oryzanol (rice bran oil) polyphenols (olive oil) Sensorial and rheological appreciation Just imagine a salad without dressing or mayonnaise, fried food without frying taste, chocolate with no bite
5 Quality aspects Gourmet oils are appreciated for their characteristic taste, smell and colour live oil, walnut oil, pumpkin seed oil, etc Refined oils should have: Bland taste: deodorization Low acidity: neutralization Low color: bleaching and thermal breakdown of coloring compounds during deodorization Transparency: filtration Low cloud point: winterization / dewaxing
6 Structure of fatty acids Linoleic acid (C18:2) 9 C H For nearly all naturally occurring fatty acids holds: Straight chains with Even number of carbon atoms Unsaturation has cis-configuration Methylene interruption in polyunsaturated fatty acids Elongation at carboxyl end so position of double bond does not shift with respect to methyl end (ω-6 remains ω-6)
7 Allylic and bis-allylic methylene Allylic CH 2 positions HC-(CH 2 ) x -CH 2 -CH=CH-CH 2 -CH=CH-CH 2 -(CH 2 ) y -CH 3 bis allylic CH 2 position
8 Nomenclature Special fatty acids CH 3 -CH 2 -CH=CH-CH 2 -CH=CH-CH 2 -CH=CH-(CH 2 ) 7 -CH Systematic name 9,12,15-octadecatrienoic acid Trivial name α-linolenic acid First shorthand C18:3 9c,12c,15c or c9,c12,c15-18:3 Second shorthand C18:3 ω3 or C18:3 n-3 γ-linolenic acid: C18:3 ω6 ccurs in black current seed and evening primrose Precursor of arachidonic acid C20:4 ω6 Stearidonic acid:c18:4 ω3 Precursor of EPA (C20:5 ω3) Now available through SDA soy (biotech product), echium oil
9 Nomenclature of fatty acids Systematic name Trivial name Notation ctanoic Caprylic (PK, CN) 8:0 Decanoic Capric (PK, CN) 10:0 Dodecanoic Lauric (PK, CN) 12:0 Tetradecanoic Myristic (PK, CN) 14:0 Hexadecanoic Palmitic (P, PK, CN) 16:0 ctadecanoic Stearic (P, PK, CN) 18:0 9-cis-octadecenoic acid leic (P, PK, CN) 18:1ω9 9-trans-octadecenoic acid Elaidic (hydrogenation) 18:1ω9 9c-12c-octadecadienoic Linoleic (P, PK, CN) 18:2ω6 6c-9c-12c-octadecatrienoic γ-llinolenic 18:3ω6 5c-8c-11c-14c-eicosatetraenoic Arachidonic (meat) 20:4ω6 9c-12c-15c-octadecatrienoic α-linolenic (soy, rape) 18:3ω3 6c-9c-12c-15c-octadecatetraenoic Stearidonic (soy) 18:4ω3 5c-8c-11c-14c-17c-eicosapentaenoic EPA (fish oil) 20:5ω3 4c-7c-10c-13c-16c-19c-docosahexaenoic DHA (fish oil) 22:6ω3
10 Fatty acid composition of various oils oil 8:0 10:0 12:0 14:0 16:0 18:0 18:1 18:2 18:3 22:1 coconut oil palm kernel oil palm oil palm superolein palm stearin cocoa butter olive oil soybean oil rapeseed oil canola oil sunflower seed oil linseed oil N.B. Totals 100% because minor fatty acids have not been listed 10
11 Fatty acid distribution in the triglycerides Vegetable oils (mostly 1,3-random, 2-random) C16:0 and C18:0 mainly on 1,3-positions Lauric acid has some preference for 2-position Linoleic acid has preference for 2-position leic acid fills in vacancies For cocoa butter this is mainly the 2-position Animal fats (1-position differs from 3 position) Palmitic acid has preference for 2-position Stearic acid has some preference for 1-position Unsaturated acids on outer, especially 3-position
12 Examples of fatty acid distributions il pos 12:0 14:0 16:0 16:1 18:0 18:1 18:2 18:3 Palm oil 1, Palm kernel 1, Coconut oil Soya bean 1, Lard
13 Sources of oils and fats Animal oils and fats Lard (porc); tallow (beef and mutton) Butter (oil) Fish oil Vegetable oils and fats Fruit oils: olive oil, palm oil Seed oils: soybean, rapeseed/canola, sunflower seed, cottonseed, palmitic and coconut (lauric oils), Specialty oils and fats, incl. gourmet oils Technical applications: e.g. castor oil, jatropha oil Confectionery fats: cocoa, shea, illipe butter Niche products: nut oils, grape seed oil, avocado oil.. Novel oils: algae 13 oils, microbial oils (in future?)
14 Production vegetable oil (MT) Seven oil seeds 2008/ / / /12 total Soybean ther Nine plant oils Total Palm oil Soybean oil Rapeseed/canola oil Sunflower seed oil Lauric oils ther (CS,GN,)
15 Sole product, co-product, or by-product Sole product and major source of income (by-products are not important or even useless) Palm oil, olive oil, sunflower seed oil, rapeseed oil, castor oil, jatropha oil, wild fats, nut oils Microbial oils? Co-product (important by-product) Soybean oil is the co-product of soybean meal Palm kernel oil is co-product of palm oil By-product in true sense, i.e. raw material is harvested or farmed/grown for other reasons Animal fats, fish oil Cotton seed oil, corn germ and grape seed oil
16 Chemical structure of phosphatides A2 A1 C R 1 H 2 C D CH R 2 C H2 C P X C X = choline (phosphatidyl choline or PC) H H 2 C H H 2 C choline H 2 C CH 3 N CH 3 CH 3 H 2 C NH 2 ethanolamine H H X = ethanolamine (phosphatidyl ethanolamine, PE) X = inositol (phosphatidyl inositol or PI) X = hydrogen (phosphatidic acid or PA) H H H inositol, link in 1-position 16
17 Chemical structure of tocopherols H R 2 6 R 1 R CH 3 CH 3 CH 3 CH 3 4' 8' CH 3 Trivial name R 1 R 2 R 3 α-tocopherol CH 3 CH 3 CH 3 β-tocopherol CH 3 H CH 3 γ-tocopherol H CH 3 CH 3 δ-tocopherol H H CH 3 17
18 Chemical structure of tocotrienols R 1 H CH 3 CH 3 CH 3 R 2 R 3 CH 3 CH 3 Tocopherols occur in vegetable oils (α-tocopherol is vitamin E); soybean oil (900 ppm), corn germ oil (1100 ppm), sesame seed oil (2900 ppm) Tocotrienols occur mainly in palm oil (530 ppm), rice bran oil (580 ppm) and wheat bran (650 ppm) 18
19 ccurrence of tocols (ppm) il tocopherol tocotrienol α β γ δ α β Palm Rapeseed Soybean oil Sunflower oil Walnut oil Wheatgerm oil
20 Chemical structure of plant sterols H 19 CH CH 3 18 CH 3 17 CH 3 CH 3 24 CH 3 26 Shown is β-sitosterol ther plant sterols (campesterol, stigmasterol, brassicasterol, Δ 5 -avena-sterol, etc) differ with respect to side chains, number and position of double bonds The free hydroxyl group can be esterified with a fatty acid or ferulic acid, or form an ether with glucose
21 Free and esterified phytosterols Red palm olein (crude) Palm oil (crude) Coconut (crude) live oil (cold pressed) Palm oil (refined) Walnut (refined) soybean (crude) live oil (cold pressed) Peanut (refined) Soya (refined) Cotton (refined) Cotton (crude) Sunflower (refined) Frituur (sunflower) Corn oil (crude) Corn (refined) Rapeseed (crude) Rapeseed (refined) sterol content (mg/100g) esterified free 21
22 Chemical structure of (poly)phenols H H H H H 3 C H H H H gallic acid protocatechuic acid ferulic acid H H H H H H H H H hydroxytyrosol caffeic acid coumaric acid Source: fruits, berry seed oil β-carotene Nutritional role: radical scavenger; antioxidant Application: adjuvant in bakery ingredients; additive to oils 22
23 Chemical structure of coloring compounds H 2 C CH CH 3 H 3 C N N H 3 C Mg N N CH 3 H 3 C CH 3 CH 3 CH 3 H 3 C CH 3 CH 3 ß-carotene CH 3 CH 3 H 3 C CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 chlorophyll b 23
24 Melting points of fatty acids The melting point increases with the number of carbon atoms in the chain It decreases with the number of double bonds Fatty acids with trans double bonds have a higher melting point than their cis-isomers In polyunsaturated fatty acids, conjugated double bonds lead to a higher melting point than the common, methylene interrupted double bond systems
25 Melting points of triglycerides Substituting a fatty acid in a triglyceride by a higher melting one raises its melting point Triglyceride melting points also depend on positional isomerism Triglycerides exhibit polymorphism and different polymorphs exhibit different melting points
26 Solubility of lipids ils and fats are miscible with alkanes, ethers and ketones n-hexane is common extraction solvent They dissolve in hot isopropanol but not in cold Isopropanol extraction process cools the miscella ils and fats are insoluble in water Soaps are water-soluble Washing oil with water to remove soaps Phosphatides are not soluble in acetone Lecithin de-oiling by extracting the oil with acetone
27 Reactions during storage and processing Hydrolysis Chemical: catalyzed by alkali and acid; rate depends on temperature, extent, and time Enzymatic: in presence of lipases (e.g. In palm oil, rice bran oil) xidation Isomerisation of double bonds Cis/trans isomerisation CH 2 CH 2 CH 2 CH 2 27
28 Reactions (2) Conjugation C H 2 C H CH 2 H 2 C CH 2 The reaction rates of both reactions Increase with an increase in temperature Are affected by catalysts (alkali, bleaching earth) Linolenic acid is more reactive than linoleic acid Two bis-allylic methylene groups versus only one Linoleic acid is much more reactive than oleic acid ne bis-allylic methylene group versus none 28
29 Reactions (3) Dimerization and polymerization Promoted by high temperature (deep fat frying) xidation and ring opening of tocopherols Dehydration of sterols forming steradienes Condensation of sterols forming di-steryl ethers 29
30 Edible oil processing flow sheet Seed Preparation Cleaning / Drying Cracking Dehulling Flaking Extraction Mechanical Extraction Solvent Extraction il Degumming Meal Hydrogenation Neutralising ( Post - refining ) Interesterification Fractionation Modification Bleaching Winterising Deodorising Refining Edible il Margarine Salad / Frying oil Shortening 30
31 CRUDE IL WATER DEGUMMING or ENZYMATIC PLC DEGUMMING SFT DEGUMMING ACID DEGUMMING ACID REFINING or ACID REFINING PLUS ENZYMATIC PLA R LAT DEGUMMING ALKALI REFINING DRY DEGUMMING BLEACHING BLEACHING DEDRISING FULLY REFINED IL PHYSICAL REFINING
32 Chemical vs. physical refining Chemical refining Advantages Can process poor quality oil Disadvantages Lower yield for high acidity oils Effluent problems with soapstock splitting Physical refining Advantages Better oil yield Close to zero effluent Eliminates one process step Disadvantages Gum disposal in stand-alone refineries
33 Physical refining requirements Wet degumming of vegetable oils Dry degumming of low phosphatide oils (palm oil, lauric oils, animal fats) with simultaneous bleaching Palm oil has high carotene content and low phosphatide Therefore, dry degumming is preferred option Treatment with degumming acid followed by bleaching earth This permits physical refining Two-step process: dry degumming followed by steam refining Yield advantage over chemical refining No soapstock treatment or effluent disposal problems
34 Refining steps Degumming and alkali refining Review of degumming and refining technologies Process automation and remote condition monitoring for centrifuges and plant Bleaching Basics and practical optimization Adsorbent solutions for oil and fat processing Highly activated bleaching clays for oil purification Latest developments in filtration Staggered Trisyl Silica Tri-clear process Hydrogenation Catalysts for hydrogenation of oils and fats
35 Refining/modification steps Interesterification Chemical and Lipozyme TL IM Enzymatic Interesterification How Enzyme Solutions Improved Process Yield and Final Product Qualities Vacuum stripping ptimizing continuous deodorization Deodorizer design and optimization Various Mechanism of oxidation Waste water treatment Recent developments
36 Purpose of modification processes Change in physical properties From oil to solid fat by hydrogenation Lowering of melting point by interesterification Lowering cloud point by fractionation Increase shelf life Lowering iodine value by hydrogenation Avoid ß-polymorph formation by interesterification Facilitate interchangeability (cost reduction) Partial hydrogenated soybean oil versus palm oil
37 THANK YU Ignace Debruyne & Associates Consultancy
CHEMISTRY OF OILS AND FATS. Albert J. Dijkstra
CHEMISTRY F ILS AND FATS Albert J. Dijkstra Production vegetable oil (m tonnes) Seven oil seeds 2008/09 2009/10 2010/11 2011/12 total 396.7 444.1 455.7 441.4 Soya bean 211.6 260.2 263.6 238.7 ther 185.1
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