Standardisation of Vegetable Oils through a Selective Hydrogenation Process.
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1 Standardisation of Vegetable Oils through a Selective Hydrogenation Process. N.Ravasio, F. Zaccheria, R.Psaro, P. Bondioli CNR ISTM and SSOG, Milano, Italy ISTM
2 Transesterification with MeOH Biodiesel Hydrolysis + esterification Transesterification Lubricants Hydraulic fluids Epoxidation Ring opening Polyols Polyurethanes Cross metathesis Self methatesis Polymers oleochemicals
3 Cross -Metathesis Oil C18:3 C18:0 TON Triolein HOSO Canola Soya Linseed J.Patel et al. Chem. Commun. 2005,
4 Polyols derived from vegetable oils POLYURETHANES US 2002/ A1 to Cognis: at least 85% oleic acid high oleic, low stearic (85-95%, %)
5 Structure-oxidative stability-cold properties relationship COOH v ox C18:3 COOH 12 9 COOH 15 6 vox mp ( C) mp Z mp E C18: C18: (7) (10) (13) (16) 40 58
6 Biodiesel quality EN Better Poly-Un Mono-Un Saturated Cold flow Cetane CN > 51 Stability IV < 120 G. Knothe, Energy Fuels, 2008, 22, 1358.
7 Oils with high Iodine Value Poor oxidative stability EN14214 IV 120 Selective hydrogenation Improve oxidative stability Worsen Keep cold cold properties
8 After hydrogenation Starting material C18:0 C18:3 C18:0 C18:3 C18:0 C18:3 C18:0 C18:3 C18:0 C18:3 C18:0 C18:3 IV = 202 IV = 104 IV = 117 Linseed Camelina Grapeseed Safflower Pumpkin Hempseed IV = 95 F.Zaccheria, N.Ravasio, P.Bondioli, Eur.J.Lip.Sci.Techn. 114 (2012) 24-30
9 Oils with high linolenic acid content Linseed Oil Methyl Esters t (min) C18:3 C18:0 C16:0 CN * IV Pp ( C) Initial Composition After Hydrogenation Camelina Oil Methyl esters t (min) C18:3 C18:0 C16:0 CN IV Pp ( C) Initial composition After hydrogenation *calculated conditions: T= 160 C, P = 4 atm H 2, Cu/SiO 2 N.Ravasio et al. Green Chemistry, 11 (2009)
10 Hydrogenated Lineseed methylesters Cu catalyst Ni catalyst Cu catalyst Ni catalyst Oxidative stability (Rancimat) from < 1h h h
11 Hempseed Oil Methyl Esters Oils with high linoleic acid content t (min) C18:3 C18:0 C16:0 CN* IV Pp ( C) Initial Composition 17, , After Hydrogenation Tobaccoseed Oil Methyl Esters t (min) C18:3 C18:0 C16:0 CN* IV Pp ( C) Initial composition 0 79,2 11,6 2, After Hydrogenation Grapeseed Oil Methyl Esters t (min) C18:3 C18:0 C16:0 CN* IV Pp ( C) Initial Composition After hydrogenation
12 t (min) C18:0 trans (% mol) Flaxseed oil methyl esters posit. (% mol) IV Pour p. ( C) Plukenetia volubilis oil methyl esters Safflower oil methyl esters Grapeseed oil methyl esters Pumpkin oil methyl esters
13 C18:0 C18:3 C18:0 C18:3 C18:0 C18:3 C18:0 C18: Soybean ME Rapeseed ME Soybean Oil Rapeseed Oil
14 Hydrogenation of rapeseed oil methylesters in the presence of different Cu catalysts at 180 C Entry Catalyst P t C18:3 C18:0 Trans Pour Point [atm] [h] [%mol] [%mol] [%mol] [%mol] [%mol] a [ C] Initial Composition Cu/Si Cu/Si Cu/SiTi Cu/SiAl Cu/Al Cu/Si IW CuO/Si Ni/Si a = % trans(9)/%
15 Physical properties of minerals and vegetable oils Viscosity (cst) Viscosity index 40 C 100 C 100 neutral oil Rapeseed oil Soybean oil HOSO Rapeseed oil hydrogenated with Cu Rapeseed oil hydrogenated with Cu After AOM test N.Ravasio et al. App. Catal. A: General, 233 (2002) p.1-6
16 Deacidification of acidic oils over SiO2ZrO2 Oil Starting acidity Final acidity 1% oleic acid in rapeseed % oleic acid in rapeseed Tobaccoseed Raw fish oil % oleic acid in rapeseed % oleic acid in rapeseed % oleic acid in rapeseed % oleic acid in rapeseed h, 180 C, MeOH/oil = 10/1 R. Psaro, N.Ravasio, F.Zaccheria, PCT/EP2008/ (2008); WO A1
17 Oil Start FFA Final Ac Olive oil fatty acids Rice bran oil PFAD PFAD Tall Oil F.Zaccheria, N.Ravasio et al. ChemSusChem, 2, 2009,
18 Tall Oil Methylesters P (atm) (%) conj (%) (%) C18:0 (%) trans (%) Pos. (%) IV PP ( C) Initial composition Cu/SiO Cu/Al2O Ni/SiO2 (Nysosel )
19 Conradson Carbon Residue After Hydrogenation Tall oil Standard P. Bondioli, N.Ravasio, F.Zaccheria, PCT/IT2006/ (2006); WO2006/ A1
20 Catalyst 98 Final FFA Conv% SiO 2 -Al 2 O 3 1% Cu/SiO 2 -Al 2 O 3 1% SiO 2 -Al 2 O 3 13% Cu/SiO 2 -Al 2 O 3 13% SiO 2 -ZrO 2 5% Cu/SiO 2 -ZrO 2 5% N2, 1h, 180 C. MeOH/oil=10/1
21 Me-esters & FFA % IV One Pot esterification + hydrogenation of Tall Oil Starting Cu/SiAl 1% Cu/SiAl 13% Cu/SiZr 5% TOFA 120 N.Ravasio et al, Topics in Catalysis, accepted
22 Conclusions Cu catalysts are effective in improving the oxidative stability of a wide range of vegetable oils When using an acidic support polyfunctional catalysts can be obtained one pot-one step processes can be set up
23 Sara Gioia Matteo Guidotti Federica Santoro Simona Brini Nasrin Shaik Carine Chan Thaw Federica Zaccheria Nicola Scotti
24 Acknowledgements Progetto VeLiCa COST Action CM0903 (UBIOCHEM) 1st Workshop, Córdoba (Spain), 13-15th May, 2010 GRACE Davison
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