Raw Materials and Processes in Oleochemistry - abiosus

1 Markus DierkerRaw Materials and Processes in OleochemistryMarkus DierkerMarkus DierkerContents Raw Materials Basic Oleochemical Transformations Oleochemical Products SummaryMarkus DierkerWorld Production of Oils and Fats 2002 (mil mt) (approx. 80%)animal(approx. 20 % declining)Raw MaterialsMarkus DierkerRegions of Production / Share of World Production 2002 (%)18122040 Raw MaterialsMarkus DierkerRaw MaterialsWorld Consumption of Oils and Fats (mil mt) %14 %5 %World Consumption of Mineral Oil in 2004: approx. mil mtMarkus DierkerRaw MaterialsNatural Generation of TriglyceridesEnergyCO2H2 OTriglyceridesWaxesNutrientsProteinsCarb o-hydratesO2 OOOOOO linear, FA witheven numbered C-chains renewable resources biodegradable balanced life cycle analysisMarkus DierkerMaterial8 10121416182022coconut oil874817910palm kernel oil455015718palm oil24256rape oil a238751rape oil b49023sunflower c (old)693sunflower d (new)

2 4931soy oil891lard131 652 Carbon ChainDistribution of Fatty Acids in Triglycerides012327121515411011515716020 942861484542853613466C18 Raw MaterialsMaterial8 10121416182022coconut oil874817910palm kernel oil455015718palm oil24256rape oil (old)238751rape oil (new)49023sunflower (old)693sunflower (new)4931soy oil891lard131 652 Carbon ChainOOOOOO glycerine backbonefatty acidsMarkus Dierker no statistic distribution of fatty acids in triglyceridesexample cocoa butter:PSO: 36%SOS: 25%PPO: 15%PPS: 1%Distribution of Fatty Acids in TriglyceridesRaw MaterialsOOOOOO glycerine backbonefatty acidsP = palmitic acidS = stearic acidO = oleic acidMarkus Dierker++[cat]OOROHROHROORO+[cat]OHORORH 2O+HOBasic Oleochemical TransformationsEsterification / Ester CleavageTransesterificationHydrogenation HOO[cat]

3 H2 HOOM arkus DierkerProduction Flow SchemeRaw Materialsoils&fatsfattyalcoholsglycerine OleochemicalsSpecialtiesfattyacidsfatty acidmethylestersulpho fatty acid estersguerbet alcoholsalkyl chloridesfatty alcohol ethoxylatesfatty alcohol sulfatestechnical estersalkyl polyglycosidestriacetinpartial glyceridesconjugated fatty acidsalkyl epoxyestersdimer acidsfatty acids ethoxylatesazelaic/pelargonic acidsfatty acid estersMarkus DierkerROO+OHOHOHROOROO[cat] TOOOOOO3+ROHC hemical Conversion of TriglyceridesOleochemicals Splittingwaterfatty acidsalcoholfatty acid estersTG + glycerine+Markus DierkerOHOOHOOHOHOHG lycerine / DerivativesOleochemicalsGlycerine purification by distillation or ion exchange pharma-grade glycerine (86%, > 99%) cosmetics, pharma, nutrition, graphic & printing.

4 Glycerides esterification / transesterification special mono-, di-, tri-glycerides GMO (glycerine monooleate) triacetin (triacetyl glycerine)Markus DierkerProduction Flow SchemeRaw Materialsoils&fatsfattyalcoholsglycerine OleochemicalsSpecialtiesfattyacidsfatty acidmethylestersulpho fatty acid esterstriacetinpartial glyceridesconjugated fatty acidsalkyl epoxyestersdimer acidsfatty acids ethoxylatesazelaic/pelargonic acidsfatty acid estersguerbet alcoholsalkyl chloridesfatty alcohol ethoxylatesfatty alcohol sulfatestechnical estersalkyl polyglycosidesMarkus DierkerFatty AcidsOleochemicalsDistilled FA C6-18 broad cutsFractionated FAC8-18fine cuts.

5 Purity > 98%StearinesC16/C18 saturatedOleinesC18monounsaturatedPolyun saturated FAC18polyunsaturatedfractionated FAdistilled FA0204060801008 1012141618200204060801008 10121416 18200204060801008 101214161820polyunsaturated FA soaps, detergents, emulsifiers, other oleochemicals, ..Markus DierkerFatty Acids - Main TechnologiesOleochemicals Splitting Distillation Fractionation Crystallisation (Hydrophilisation) Hydrogenation (partial or full) EsterificationMarkus DierkerFatty Acids Oleic AcidOleochemicals Production crystallisation (hydrophilisation) saturated acids as by-products Properties compromise of low melting point and oxidative stability melting point: 5 8 C, esters even lower relative good stability compared to rape seed fatty acid due to low amount of polyunsaturated acids same behavior in oleic acid derivativestallowC16/18 fatty acidstechn.

6 Stearic aicdoleic acidMarkus DierkerFatty Acids - SpecialtiesOleochemicalsPelargonic Acid esters plasticizers, lubricants, corrosion inhibitorsAzelaic Acid esters, plasticizer, soaps, polyamides, nylon, adhesives, coatingsHOOHOOOOHOHO+O3 Markus DierkerConjugated Fatty AcidsOleochemicalsUKD Fatty Acids mixture of many isomers alkyd resinsTonalin two isomers: c9,t11- / t10,c12- CLA functional foodsROO+isomers+Markus DierkerMonomer / Dimer AcidsSpecialtiesIsostearic AcidsEmersol hydrogenation, fractionation isostearic acid cosmetics, lubricants, plastic auxilliariesDimer AcidsEmpol purification polyamides, polyesters, lubricants, corrosion inhibitorsmonomer acidC18dimer acidC36+OHOOOHOHOOHO T[cat]

7 +Markus DierkerProduction Flow SchemeRaw Materialsoils&fatsfattyalcoholsglycerine OleochemicalsSpecialtiesfattyacidsfatty acidmethylestersulpho fatty acid esterstriacetinpartial glyceridesconjugated fatty acidsalkyl epoxyestersdimer acidsfatty acids ethoxylatesazelaic/pelargonic acidsfatty acid estersguerbet alcoholsalkyl chloridesfatty alcohol ethoxylatesfatty alcohol sulfatestechnical estersalkyl polyglycosidesMarkus DierkerFatty Acid Methyl Esters fatty alcohols intermediate to production of special esters solvents, lubricants Biodiesel (rape seed oil methyl ester)OleochemicalsMarkus DierkerROO[cat]+H2- ROHHOF atty AlcoholsOleochemicals production by continuous hydrogenation of esters over 1 mil mt produced from renewable raw Materials main raw material for saturated alcohols: coconut and palm kernel oil competing Processes using petrochemical sources Ethylene: Ziegler, Alfol-Process Olefins.

8 Hydroformylation/Reduction share of natural sources is risingMarkus DierkerFatty AlcoholsOleochemicals main intermediate to other oleochemicalscarboxylic esterssulfosuccinatesfatty alcohol sulfatesfatty alcohol ethoxylatesfatty alcohol ether sulfatesfatty alcohol phosphatesalkyl polyglucosidesalkylhalogenidesacrylatesm ethacrylatesfatty aminesfatty alcohols main application as detergentsMarkus DierkerFatty AlcoholsSaturated AlcoholsLorol , Hydrenol , Stenol C 6-10 plasticizer rangesolubiliser, defoaming agents, ..C12-14detergent rangefoam stabilisers, lubricant additives, ..C12-18consistency giving factors,C16-22 melting point regulators,lubricants for cosmetics and pharma.

9 OleochemicalsUnsaturated AlcoholsHD-Ocenols C16-18solvents, defoamers, plasticizer, emulsifier, oil component in cosmeticsROO[cat]+H2- ROHHOM arkus DierkerFatty Alcohols SpecialtiesOleochemicalsDiolsSpeziol C8 / C10 / C12 / C18cosmeticsagro chemicalspharmaceuticalsplasticizerBranc hed AlcoholsSpeziol C16-18 satur. / chemicalsMarkus DierkerGuerbet AlcoholsSpecialtiesGuerbet AlcoholsRilanit C16 / C20plasticizersspray lubrication (metalworking)solubilizer for water-miscible MWFmold release agentsoil components in cosmetic applicationdispersing agentsHO T, pOHOO aldol H2O- [H]+ [H][cat]Markus DierkerFAEON arrow Range Ethoxylates (NRO)End-Capped EthoxylatesFatty Alcohol EO/PO AdductsOOHmOOnOOnHFatty Alcohol Ethoxylates (FAEO)

10 Nonionic surfactant, low foaming good emulsifiers for W/O and O/W emulsions intermediate to oleochemical productsSurfactantsOOnOH+OOOH nnethoxylationMarkus DierkerFatty Alcohol Sulfates (FAS)SurfactantsFatty Alcohol Ether Sulfates (FAES) anionic surfactants very good skin compatibability very good foaming power basic surfactants in cosmetic detergents and cleaners insensitive to water hardness very good water-solubility anionic surfactants good foaming power fire extinguisher foams detergents for home care and cosmetic application insensitive to water hardnessOSOOONaOHsulfationOOHnsulfationO OnOSOOONaMarkus DierkerOHOOHOHHOHOOH+OOHOHHOOOOHOHOHHOOA lkyl Polyglucosides (APG)