AP Biology 2006-2007 Lipids Oils Fats. AP Biology Lipids: Fats & Oils.
‘Palm Oil: Going Beyond Basic Oleochemicals’mpoc.org.my/upload/P6_DrYeongPOTSRomania.pdf ·...
Transcript of ‘Palm Oil: Going Beyond Basic Oleochemicals’mpoc.org.my/upload/P6_DrYeongPOTSRomania.pdf ·...
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‘Palm Oil: Going Beyond Basic Oleochemicals’
Venue: Bucharest, Rumania
Date: 18th September, 2012
By:S.K. Yeong, Hazimah A.H. and Y.M. Choo
MALAYSIAN PALM OIL BOARD
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What are OLEOCHEMICALS?
Chemicals derived from natural oils/fats - could be of animal, marine or vegetable oil sources
Derived from breaking the oils/fats into corresponding constituents, i.e. fatty acids, glycerol, fatty esters, etc.
Normal process involves hydrolysis or transesterification
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SUNFLOWER
RAPESEED
SOYBEAN
PALM
3
50.2 mil tonnes
41.7 mil tonnes
12.9 mil tonnes
23.5 mil tonnesGlobal production oils and fats in 2011.Source: Oil World Annual, Oil World Weekly and Malaysian Oil Palm Statistics 2011.
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Palm Oil
Malaysia 2011:Production of CPO = 18.9 mil tonnes
Production of CPKO = 2.14 mil tonnes80 - 85% for food applications
15 - 20% for non-food applications
MesocarpKernel
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CH2
HC
CH2 OCOR3
OCOR2
OCOR1
3 H2O
CH2
HC
CH2 OH
OH
OH R1COOH
R2COOH
R3COOH
Triglyceride Water Glycerol Fatty acids
R1, R2 and R3 vary in chain length and degree of unsaturation
Palm Oil Chemistry
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Composition of Oleochemicals Depends on Starting Raw Materials
R, R’, R’’ Palm oil Palm stearin
Tallow Coconut oil
Palm kernel oil
C6 0.2 0.3C8 8.0 4.4C10 7.0 3.7C12 0.23 0.3 48.2 48.3C14 1.09 1.3 2.5 18.0 15.6C16 44.02 55.0 26.6 8.5 7.8C18 4.54 5.1 21.8C16:1 0.12 2.3 2.0C18:1 39.15 29.5 42.8 5.7 15.1C18:2 10.12 7.4 2.3 2.1 2.7C18:3 0.37 -OTHERS 0.38 0.7 4.0 0.26
48.8%48.6%
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Basic OleochemicalsBasic:
• Fatty acids• Fatty methyl esters• Fatty alcohols• Fatty amines• Glycerine
Derivatives: basic oleochemicalssubjected to further reactions
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Production of Oleochemicals
Hydrolysis TransesterificationH
ydro
gena
tion
Am
inat
ion
Hydrogenation
Am
ination
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Oleochemicals Industry in Malaysia• Started with one plant in 1980 • Currently in operation 17 plants - total
production capacities 2.6 million tonnes. • Major feedstock - processed PO, PS and PKO
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Malaysian Oleochemicals:Export Volume and Value
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0.00
2.00
4.00
6.00
8.00
10.00
12.00
0.00
0.50
1.00
1.50
2.00
2.50
2004 2005 2006 2007 2008 2009 2010 2011
Value, RM BilVolume, Mil Mt
Volume, mil tonne Value, bil RM
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Export Volume of Basic Oleochemicals
0100200300400500600700800900
1000
2007 2008 2009 2010 2011
Volu
me,
x10
3to
nne
Fatty acidFatty alcoholMethyl esterGlycerine
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Major Export Destinations
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EU
China
Japan
U.S.A.
India
R.O.W.
European Union,22.59%
China, 14.49%
Japan,9.76%U.S.A.,
8.52%
India,5.51%
Rest of World,39.11%
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Beyond Basic
ConsumerProducts
Formulation (Semi Finished)
Derivatives (Intermediate Chemicals)
Basic Oleochemicals
Refined Oil
Palm Fruit
Value
High
Low
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Application of Oleochemicals
• Surfactant• Washing and cleaning products• Personal care products
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Surfactant
Surface active agent, a chemical that stabilisesmixtures of oil and water by reducing the surface tension at the interface between the oil and water molecules
Function - detergent, wetting agents, emulsifiers, conditioning agents, solubilisers.
Hydrophillic head (charged molecules dissolves in water) and hydrophobic tail (long hydrocarbon chain derived from palm)
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C12-C14 fatty acids for foams/lathers (from palm kernel oil)
C16-C18 fatty acids for cleaning purposes (from palm oil)
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Soap
Soap – is still the major application in the non-food sector3 major methods of production Saponification of oils/fats Neutralization of fatty acids Saponification of methyl
ester
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Soap from Oils and Fats (Saponification)
Mixture of fresh PO/PKO are boiled with excess alkaliOils/fats converted to soap and soap lye. Brine is added for better separation The soap is dried, to produce soap. The soap lye is processed to USP grade glycerin
RCH2COO-CH2
RCH2COO-CHRCH2COO-CH2
3NaOH
3 RCH2COO- Na+
+ CH2OHCHOHCH2OH
Soap +USP glycerin
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Soap from Fatty Acids(Splitting)
In 80’s, oleochemicalsindustry developed in Malaysia Fresh PO or PKO are split to fatty acids and sweet waterThe fatty acids are either distilled, stripped or fractionated.The sweet water is processed to USP grade glycerin
RCH2COO-CH2
RCH2COO-CHRCH2COO-CH2
Steam3 RCH2COOH+ CH2OHCHOHCH2OH
Fatty acidsUSP glycerin
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Soap from Fatty Acids(Neutralisation)
Distilled, broad cut or fractionated fatty acids are neutralized to form soap.
RCH2COOH
NaOH
RCH2COO- Na+
Soap
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SoapQuality of soap noodles produced in Malaysia PO 80, 75, 70, 60 PKO 20, 25, 30, 40 H2O 9-12.5% TFM 79-83% FFA 1.3 - 7.0% GLY 0.4 - 0.6% Sesq. Present Titer 38-52oC
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Soap Pilot Plant
1. AMALGAMATOR2. ROLL MILL3. PLODDER4. PNEUMATIC PRESS MOULD
1 2 3
4
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Specialty Soap
Specialty soaps - contain special additives for specific functionality (1- 5%)Process similar to toilet soapsCategories of additives: emollients, humectant,
moisturisers, occlusive agents, dermabrasive agents, medicaments, anti-irritants, etc.
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Transparent SoapRecently transparent soaps are very popular Palm-based fatty acid was used to replace tallowProcess - neutralization of fatty acidsCan be used for decoration and skin careUse as gifts
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Ingredient Function
Fatty acids Surfactant
NaOH NeutralizerGlycerol HumectantSugar Humectant
Alcohol Solvent
EDTA Sequestering agent or chelating agent
Water Filler
Typical Formulation of Transparent Bar Soap
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Process of Making Transparent Bar Soap at Lab Scale
1
2
3
Neutralization of fatty acids
Soap
Sugar, glycerol, alcohol, EDTA, water
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Colour
Perfume
4
76
5
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Mould
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Performance Evaluation of Transparent Bar Soap
Detergency test
Foaming test
Transparency value
Hardness
Ocular and dermal irritation test
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Advantages of Palm-based Transparent Bar Soap
Contains natural ingredientLow pH – closer to pH of skin
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Fatty Alcohols
Most important market for fatty alcohols are mid-cut (C12-14) and long chain (C16-18)
Derivatized - fatty alcohol ethoxylate(FAE), fatty alcohol ether sulphate (FAES), fatty alcohol sulphate (FAS).
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Major application
surfactants for household detergents
For example dishwashing liquid, shampoo, shower bath, etc.
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Methyl Ester Sulphonate (MES)
MES is an anionic surfactant derived from oleochemicals. Therefore it is derived from renewable sources.
It is used as active compound in cleaning products.
Its can be used to replace linear alkyl benzene sulphonate (LAS), the most commonly used petrochemical based surfactant in detergent products.
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CH3-(CH2)n-CH-COOCH3
SO3- Na +
(dissolves in water with the head group negatively charged = anionic surfactant)
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Sulphonation
Digestion
Bleaching
Neutralisation
Drying
METHYL ESTER
SATURATED METHYL ESTER(IODINE VALUE < 0.5)
Methyl Ester Sulphonate (MES)
Hydrogenation
MES Process
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>85
<0.1
GuaranteedParameters
Colour (Klett)
3.7- 6.0<6Disalt (%)0.7 – 1.2<2.5Volatile (%)
0.3 – 0.4<0.4Methanol(%)
88.7 – 90.3Active (%)
30 - 94<100
0.02 – 0.1H2O2 (%)
MPOB
PROPERTIES OF MES
FROM PALM STEARIN
Methyl Ester Sulphonates (MES) Saturated methyl ester as feedstock
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0102030405060708090
C12 C14 C16 C18 LAS AS
54ppm 270ppm
0102030405060708090
4 9 12 16 20 24 28
LAS MES 37
0102030405060708090
C12 C14 C16 C18 LAS AS
C12 C14 C16 C18 LAS AS
Performance of MESGood washing performance in hard water and without phosphate
Good hard water tolerance
Good synergy with soap as additive
Good solubility
Soft and no skin irritaion
Good biodegradability
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MES produced by MPOB has been
successfully formulated into powder and
liquid detergent
Formulations is usually kept as a trade secret by individual producer
Application of MES
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Fatty Amines
Derivatives of Fatty acids and Fatty alcohol.Traditionally derived from reaction of fatty acids or fatty alcohols and ammonia or ureaClassified as Primary, Secondary, Tertiary amines and Quaternary Ammonium Compounds.
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Examples of Fatty Amines(chemical structures)
hydrocarbon feedstock = R ammonia
PRIMARY AMINES
Secondary amines Tertiary amines
CCCCCCCCCCCCCCCC
H
H H
H
H
H
H
H
H
H
H
H
H
H
H
H H
H H
H
H
H
H
H
H
H
H
H
H
H
H
NH2
H
H
R CH2 N
CH3
CH3
R CH2 N
CH3
H
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Examples of Fatty Amines(Quaternary Ammonium Compounds or Quats)
• Yellow : hydrocarbon source• Cyan: hydrophilic positive amine• Cyan: hydrophilic negative counter ion• Preferred chemical structure:
Esterquats-more environmentally acceptable
R CH2 N
CH3
R
CH3+
Cl-
Traditional dialkyl quats
HO CH2 CH2
NCH2
CH2
CH2 O
CH2 O
C
O
CH2
C
O
CH2
R
RH3C
+
CH3 SO4-
Quaternary triethanolamine ester or esterquats
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Main Application of Fatty Amines
Primary and secondary amines are used as precursor for tertiary aminesLargest application of fatty amines were in textile industries though some may go into specialized industries such as floatation ores, bactericides and additives in plasticAwareness in environmental issues have changed the fatty amines industries significantly especially in household fabric care / softener
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Why we Need to Use Fabric Softener in First Place?
1.Softening and long lasting fragrance on cotton fabric: e.gtowel.
2.Prevent accumalation of static charges on silk materials
3.Prevent excessive wrinkle on fabric after laundry
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To reduce accumalation of cationic material that will retard the balance of ecosystem in the
environment
Current Trend: Easily Biodegradable
X
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Fabric Softener from Palm Oil
N
O
HO
H3C +
CH3SO4-
O
O
O
Positively charged hydrophilic headHydrophobic tail
Stearyl
Palmityl
Palm Oil Fruits Palm Oil
Quaternary triethanolamine ester or esterquats
Fabric Softener
Fatty acid methyl ester or fatty acids
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Cosmetic and Personal Care
Cosmetic and personal care are substances or preparation intended to placedon the external part of human body with the aim to cleaning them, perfumingthem, changing their appearance and protecting them or keeping them in goodcondition.
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COSMETICS
COSMETICS AND
PERSONAL CARE
PERSONALCARE
WHITE COSMETICSLOTIONCREAM
COLOURED COSMETICSFOUNDATIONLIPSTICKHAIR DYESBLUSHEREYE SHADOW
HAIR• SHAMPOO• CONDITIONER
SKIN• SHOWER GEL• SHOWER CREAM• SHOWER FOAM• SOAPFACE• FACIAL CLEANSER• TONER• MOISTURISER
ORAL• TOOTH PASTE• MOUTH WASH
HYGIENE• DEODORANT• OTHERS
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Emulsifier• Emulsifier - a type of surfactant used to
keep emulsion (immiscible fluids) well dispersed.
Hydrophillic head(water loving)
Lypophillic tail (oil loving)
OilO/W EmulsionW/O Emulsion
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Oil WaterEmulsifier
Importance of Emulsifier
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Oleochemicals in CPC productsFunction Class Examples
Emollients Fatty acidsFatty alcoholsEstersTriglycerides
Stearic acidCetyl/Stearyl/Cetearyl alcoholsIPM, IPPPK glycerides, MCT
Humectant Polyol GlycerinSurfactants/emulsifying agents
SoapsEsters
EthersAnionic surfactants
Stearates, Myristates (Na, TEA)Glyceryl stearates, SorbitanStearatesCeteareth-2, 12, Steareth-2, 21SLS, SLES
Thickener Fatty alcohols Cetyl/ Stearyl/Cetearyl alcohols
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Active Ingredients in Cosmetic Products
Active ingredients Example
Sunscreen 3,4-Benzophenon, zinc oxide, titanium dioxide
Whitening agent Arbutin, Kojic acid
Anti wrinkle Vitamin A (carotenoids) and E (tocopherol and tocotrienol)
Anti inflammatory Tea tree oil
Moisturising agent Plant extract eg. cucumber extract
Anti acne Tea tree oil
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Colour cosmetic, for example compact powder, liquid foundation, lipstick, etc.
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Leave on or wash off products with vitamin E. Example, lotion, cream, shampoo, conditioner, etc.
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Glycerol
Glycerol is a polyol obtained from either hydrolysis or transesterification – co-product of the fatty acid, fatty alcohol and biodiesel industries
CH2OHCHOHCH2OH – mwt 92
Non toxic, widely used in food, cosmetic and pharmaceutical industries
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Glycerol …. Traditional Applications
Many grades – pharmacopia > 99.5%
medical & food uses
Solvent/drugs carrier – cough mixture, antibiotics
In food products as texture improver, eg. ice
cream
Transparency effect in soap
Antifreeze – when add to water lowers melting point of water
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Hygroscopic – useful as humectant in cosmetics, toothpaste, tobacco to prevent moisture loss on storage
Combine with other polyols to produce polyurethane
Convert to monoglyceride – as emulsifier for margarine, bakery products
Glycerol + HNO3 nitroglycerinean explosive
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Recent Applications
Epichorohydrin - building blocks for elastromer, resin, etc.
Propylene glycol - as humectant in cosmetic, toothpastes, food, tobacco products, carrier for fragrance.
Polyglycerol - converted to polyglycerolesters mainly used as emulsifiers cosmetics and food.
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Crude glycerol Crude polyglycerol
Polyglycerol from Crude Glycerine
A potential outlet for biodiesel glycerine
Purified polyglycerol
Glycerol Derivatives
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Polyol and PolyurethanePolyol are compounds with multiple hydroxyl functional groups
H-O-R-O-HReacted with isocyanates to make polyurethaneTwo possible chemical process– Alkoxylation – polyether polyol– Esterification – polyester polyol
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Natural PolyolDerived from vegetable oils by several different
techniques.
Types of vegetables oil:
Castor oil, Soya bean oil, Canola oil, Peanut oil and Palm oil
Castor oil has been used since 1937 - the only
natural occurring polyol
Other are produced via chemical modifications
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Polyol
Polyol pilot plant
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Formation of Polyurethane
ISOCYANATE POLYOL
POLYURETHANE
GLYCEROL,DERIVATIVE OFTRIGLYCERIDES OR GLYCEROL
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High Pressured PU Machine
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Palm-based PU for Automotive Components• PU products formulated
palm-based polyolmade from palm oil
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Rigid PU
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Ornamental products – Islamic motives
Ornamental products – contemporary motives
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