Soy Beans. Sunflower Kernels. Rape Seeds

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1 Vegetable Lecithin production & Industrial Scale Modification W. van Nieuwenhuyzen Lecipro Consulting AOCS Lecithin SC Montreal, April 27-28,201328,2013 1

2 Topics 1. Lecithin Production 2. Phospholipid Properties 3. Plant Scale Modification 4. Specifications 2

3 Production of Vegetable Lecithin Oil seeds are the primary source Lecithin occurs in oil seeds at % Crushing opens the cell walls Lecithin recovery % Beyond 280 million T oil seeds are crushed Most oil-soluble phospholipids follow the oil and must be removed 3

4 Different oil seed sources for vegetable lecithins Soy Beans Sunflower Kernels Rape Seeds 4

5 Basic Soybean Composition 5

6 (Phospho)Lipid Molecular structures Fats = Triglycerides R1, R2, R3: fatty acids chain length C8 <-> C22 chain : saturated,mono-poly unsat. R1 R2 R3 Emulsifier basis : Mono-Diglyceride Diglyceride OH Monoglyceride CH 2 OH CH 2 OH Lecithin Standard O CH 2 O P O X OH CH 2 O P O O X Hydrolysed lecithin 6

7 Processing of Vegetable Lecithins Seed Cleaning Non Degummed oil Water / Acid Degumming Oil Dehulling Hulls Drying EXPELLING Cooling Extraction Protein Meal Storage Desolventizing Standardization Lecithin 7

8 Importance for good lecithin Expelling = pressing of sunflower or rapeseed oil (not for soya oil) Good seed treatment & dehulling benefit: colour, degumming Standard PL composition and Quality standards Convenience in use 8

9 Enzymatic activity during seed crushing Critical process zone Pass Temperature range from 40 to 70 C quickly: Inactivate enzymes (PL-D) to avoid Non Hydratable Phospholipid (NHP) formation Refinability of crude oil Low NHP, FFA, oxidized fatty acid chains Lecithin quality - PL composition Yields Higher oil loss and lower lecithin yield with poorer refinability Lecithin yields in water- degumming Crude Soya oil 1000 ppm P 100 ppm P: 2.5% yield Crude RP /SF oil 800ppm 300 ppm P: 1.5% yield 9

10 Removal of Lecithin: Degumming in Lecithin production 1-2 % water is added to crude oil at 70 C, hydrating phospholipids gums or sludge Aqueous gums precipitate and can be centrifuged Thin film vacuum drying reduces water from 40 % to <1 % Drying time is 1-2 minutes at C > cooling to 50 C 10

11 Rheology of lecithin gums during drying Free after W. van Nieuwenhuyzen, JAOCS,, 53, , 427, 1976 Viscosity of lecithin gums during drying Viscosity Pa. a.s % Moisture 11

12 Lecithin processing conditions Lecithin as it is brown colour Lecithin with lighter colour Bleaching with Hydrogen peroxide, POV max 10 One step single bleached lecithin US definition, not valid in Europe Two steps double bleached lecithin non-food, technical grade in Europe Clear Transparent lecithin non-degummed oil filtration 12

13 Requirements for Clear Transparent Lecithin Low HI - impurity level for regulative and technological reasons Stable thin liquid lecithin oil systems need absence of turbid dry substances Low metal content, optimal taste and color Clear transparency occurs at HI << 0.03 % (< 300 ppm) 13

14 Intensive Filtration of Non-degummed Oil Pressed oil with 3-7 % d.s.: filter of decanter centrifuge Filtration without filter aid feasible Miscella filtration is possible but Ex-proof Extracted oils with 0,2-0,4% d.s. more efficient with special filter equipment with use of pre-coat & filter aid Soy need 0,1% body-coat Filter aids: Dicalite, Celite 545, JRS EFC Lecithin AI 60% is high viscous and cannot filtered deeply on plant scale. 14

15 Crude Oil filtration (chart borrowed from Mahle AMA Filter) 15

16 Topics 1. Lecithin Production 2. Phospholipid Properties 3. Plant Scale Modification 4. Specifications 16

17 Phospholipids in vegetable lecithins 100% 80% 60% 40% 20% Other PA PI PE PC 0% lecithin lecithin lecithin Soy Sun Rape 17

18 Fatty acid division in lecithins 100% 80% 60% 40% 20% 0% lecithin lecithin lecithin Soy Sun Rape others C18:3 C18:2 C18:1 C18:0 C16:0 18

19 Exchange of vegetable lecithins Soy lecithin Traditionally available in top quality standards Sunflower lecithin Need intensive oil filtration during processing (low TI) Nutty pleasant taste Rapeseed lecithin Need intensive oil filtration during processing (low TI) Colour and taste critical Exchange of type Evaluate functionality and recipe 19

20 Topics 1. Lecithin Production 2. Phospholipid Properties 3. Plant Scale Modification 4. Specifications 20

21 Lecithin Modification processes Enzymatic Hydrolysis Acetylation Hydroxylation Fractionation De-oiling Spray drying 21

22 OBJECTIVE : Why Modification? different hydrophilic - lipophilic character HLB range 2-12 reduced Calcium sensitivity PRODUCT RANGE : deoiled lecithin powder / granules - 2% oil fractions - PC enriched / isolated - PE enriched enzymatic hydrolysed hydroxylated * acetylated* clear standard lecithins - 35% oil speciality mixes * No E-number in Europe 22

23 Fractionation techniques for phospholipid separation Alcohol fractionation Chromatographic isolation 23

24 Reasons for Fractionation Deoiled lecithins in powder and granule form with bland taste Specific surface-active active properties, stabilizing emulsions Phosphatidylcholine (PC) forms liposomal bilayers with encapsulation capacity PC has specific nutritional and pharmaceutical properties 24

25 Lecithin fractionation process Crude Lecithin Alcohol Fractionation Alcohol soluble fraction PC- 35 Chromatographic separation PC-80 Isolate Alcohol insoluble fraction PI -F Alcohol soluble fraction PE -F Spray-drying on carrier Mixing on carrier PC-80 fraction on maltodextrin PC-80 fraction on oil 25

26 PC/PE ratio in lecithin fractions PC PE PI PC/PE ratio Standard Lecithin Alcohol soluble PC Alcohol insoluble PI-F PC-80 Isolate Egg Lecithin PC = phosphatidylcholine PE = phosphatidylethanolamine 26

27 Fractionation Plant up scaling issues Viscosity of alcohol-lecithin lecithin mixture: Ratio Ethanol: Lecithin = 3-4:1 Temperature control Stability and shelf life of fractions Management of co-products (80%) essential for economic success. Continuous counter current extraction process 27

28 Fractionation techniques for oil removal Acetone extraction Critical Carbon dioxide extraction Membrane technology 28

29 De-oiling of Lecithin Crude lecithin Acetone Extraction Belt drying Sieving Packaging Deoiled lecithin Powder / Granules 29

30 Composition of soy lecithin 100% % Oil 60% 40% 20% Complex Carbohydrates Glycolipids Phospholipids 0% Standard Lecithin Oil free Lecithin 30

31 Lecithin hydrolysis with enzyme Phospholipase A 2 R 2 O C CH 2 O O CH O C R 1 + H 2 O C HO CH 2 O C CH O R 1 + O HO C R 2 O O CH 2 O P O X CH 2 O P O X O - O - phospholipid + water lysophospholipid + fatty acid Degree of hydrolysis : %, depending on requirement increasing hydrophilicity 31

32 Types of phospholipase Phospholipase A 1 Phospholipase A P X 3 4 Phospholipase C Phospholipase D 32

33 Hydrolysis 33

34 Hydrolysis of Sunflower lecithin EP [2001] Unilever 0.83 ml Lecitase 10L per kg lecithin Degree of Hydr rolysis % Hydrolysis time in H DH-PE DH-PC DH-PI 34

35 Benefits for hydrolysis Formation hydrophilic Lyso-PLs Transformation inactive PE - functional LPE Improvement of Calcium Resistance Effective processing aid Oil Degumming LPL s positive interactions: Starch anti-staling bread Proteins emulsion stability Heat stable W/O emulsions 35

36 Hydrolysis Plant up scaling issues Addition of PL-A to viscous Lecithin (gums) Stirring in (semi-) batch process Constant reaction / residence time in continuous hydrolysis process Material rheology change Ideal: 3-4 stirred vessels, but expensive Plug flow reactor with good Length / Diameter ratio Plant control of degree of hydrolysis Relationship hydrolysis emulsifying properties 36

37 Acetylation of Lecithin R 1 R 1 R 2 O O CH 2 O P O CH 2 CH 2 N + H 3 + CH3 C O. CH 3 C O O R 2 H N H O C + O CH 3 CH 3 C OH PE + Acetic anhydrid Acetyl PE + Acetic acid Increased Hydrophilicity HLB 6 still weak O/W Emulsifier R = Fatty acid 37

38 Acetylated Lecithin Acetylating of PE with Acetic anhydride Product has no E number in Europe because nobody has requested for registration In N-America use as food grade lecithin in e.g. baked good and pan release agent In animal feed milk replacers use as O/W emulsifier 38

39 Hydroxylation of Lecithin PL + Hydrogen peroxide Hydroxy-PL + Water strong hydrophilic O/W Emulsifier HLB 9-10 Easily dispersible in Water (white emulsion) R = Fatty acid 39

40 Hydroxylated lecithin Hydroxylation of double bonds in fatty acid chains with Hydrogen peroxide at low ph Excellent water dispersible lecithin due to enhanced hydrophilic properties No European E number In N-America use in baked goods, O/W emulsions and instant wetting products 40

41 Spray dried lecithin powders Spray drying of liquid lecithin homogenized in whey protein solution convenient lecithin powder on carrier (50%) Casein level determines encapsulation and free fat content Spray cooling of liquid lecithin on wheat flour, soy protein, dairy protein Lecithin content 20-30% Handling / Dosing Convenience 41

42 Topics 1. Lecithin Production 2. Phospholipid Properties 3. Plant Scale Modification 4. Specifications 42

43 Legal Lecithin Specifications FAO/WHO Codex FCC USA EU E322 Acetone Insoluble % >60 >50 >60 [56*] Hexane / Toluene Insoluble % <0.3 <0.3 <0.3 Moisture % <2.0 <1.5 <2.0 Acid Value mg KOH/g <36 <36 <35 [45*] Peroxide Value meg/kg <10 <100 <10 * for enzymatic hydrolysed lecithin 43

44 Typical Chemical Analyses Standard liquid lecithins Sunflower Lecithin Soya Lecithin Rape seed Lecithin Acetone Insoluble Acid Value Moisture Hexane Insoluble Gardner Color POV Viscosity Pa.s

45 Analytical tests lecithins Lecithin contains phospholipids, by-lipids, complex sugars and embedded crude oil Phospholipids are the powerful portion Phospholipids insoluble in Acetone All components soluble in Toluene / Hexane The legal requirement for Lecithin E 322 are: Acetone Insoluble AI min. 60 % (Active matter) Toluene Insoluble TI max. 0,3 % (impurities) 45

46 Summing up Phospholipid composition of standard lecithin is important Source can be : soy, rapeseed, sunflower Often used modifications are enzymatic hydrolysis, fractionation and deoiling. Modifications aim for specific emulsifying properties Emulsion tests: first screening of desired properties Methods of analysis are important for legal, commercial and technological reasons. 46

47 Recommended Literature A Wendel, Lecithin, Chapter in Kirk-Othmer Encyclopedia of Chemical Technology, Vol 15, , 210, Wiley & Sons (1995) Lecithin, AOCS- INFORM, Vol 7, Nr 11, (1996) B. Szuhaj, Lecithin, Chapter 13, Baileys Oils & Fats, Vol 3, , Wiley (2001) S.D. Doig, R.M.M. Diks, Toolbox for modification of the lecithin head group, Eur.J.Lipid Sci.Technol.105, part 1: , 367, part 2: (2003) W. van Nieuwenhuyzen & M Tomas -Update of vegetable lecithin technologies, EJLST 110, (2008) Phospholipid Technology and Applications, Ed. F.D. Gunstone, The Oily Press (2008) WvN: Lecithin and Other Phospholipids, Chapter 10 in Surfactants from Renewable Resources, Ed. M. Kjellin, I. Johansson Wiley (2010) 47

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