Application note. Enabling purifications of fatty acids with Contichrom
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1 Application note Enabling purifications of fatty acids with Contichrom ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
2 Overview Fatty acids have broad application area, including pharmaceuticals, nutraceuticals, food supplements, chemical intermediates Often high purities are required for the applications To obtain a high purity fatty acid in large amounts, Contichrom with MCSGP is the only available production technology as it combines high throughput with high resolution ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
3 Case Study: Contichrom for ω-3 fatty acid purification ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
4 Introduction: Fat, Oil Oil (liquid at room temperature), fat (solid at room temperature): Fatty acid: Eicosapentaenoic acid (EPA): C20:5 Example of an unsaturated fat triglyceride. Left part: glycerol, right part from top to bottom: palmitic acid, oleic acid, alpha-linolenic acid, Source: Wikipedia Docosahexaenoic acid (DHA): C22:6 The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, EPA acid is a polyunsaturated n 3 (omega-3) fatty acid ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
5 Purification of ω-3 fatty acids ω-3 fatty acids for pharmaceutical applications are made from fish oil Products: Omacor /Lovaza (1.3 bio US$ sales) Used as prescription medicine as a supplement to diet for the treatment of elevated levels of triglycerides (cardiovascular diseases) API of Omacor: 45% EPA-EE, 35% DHA-EE Several companies develop biosimilar APIs Several companies develop high purity EPA-EE as 2 nd generation product ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
6 Fatty acids for nutraceuticals Sequential purification of fatty acid stream: 1st MCSGP step: large volume, DHA with nutraceutical purity, EPArich side stream 2nd MCSGP step: smaller volume, EPA with pharma purity analytics of feed material: DHA-EE MCSGP1 EPA-EE S1 P1 (DHA food grade 80% purity) W1 (EPA < 90% purity ) MCSGP2 W1 W2 P2 S2 (EPA pharma grade > 95% purity) ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
7 Fatty acids for nutraceuticals Simultaneous purification of EPA/DHA in single equipment by multi-fraction MCSGP Sequential purification of fatty acid stream: 1st MCSGP step: large volume, DHA with nutraceutical purity, EPA-rich side stream 2nd MCSGP step: smaller volume, EPA with pharma purity ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
8 Case Study: MCSGP process design: 1 st step Perform analytical RP-HPLC batch chromatography Feed purity 74%, target purity >97% (generic fish oil feed purchased from TCI Europe N.V.) Main impurity Docosahexaeonic acid ethyl ester (DHA- EE) EPA-EE DHA-EE ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
9 UVnorm[mAU/mAU]*12, Conc [mg/ml] Case Study: MCSGP process design: 2 nd step Batch chromatography for the purification of EPA-EE, recording the elution fraction product purity by analytical HPLC Results: UV-signal and fraction analyses: % % 10.0 conc EPA-EE UV 90% 8.0 Purity EPA-EE EPA-EE spec 85% 80% Purity HPLC [%] % B % Time [min] on Daisogel ODS-RPS ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
10 UVnorm[mAU/mAU]*12, Conc [mg/ml] Case Study: MCSGP process design: 3 rd step Define sections of pure product extraction (red) and product-containing impurity recycling (blue + green) based on prior analytical purity measurements using the Contichrom Software Wizard 15.8min 17.3min 19.3 min % conc EPA-EE UV Purity EPA-EE EPA-EE spec 95% 90% 85% 80% 75% Purity HPLC [%] B % Time [min] waste recycle product recycle waste ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
11 Case Study: MCSGP process design: 4 th step Use Contichrom MCSGP wizard to convert batch method into MCSGP method by simple click on the Write Method button (yellow arrow) ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
12 Case Study: details of one MCSGP cycle run Zoom of 1 cycle (only UV1 and tasks of column 2 shown) W/P uptake feed P/S uptake Removal of W W/P rec product elution P/S rec Cleaning and reequilibration Pressure at pump 1 ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
13 Case Study: anatomy of multiple MCSGP cycles Results from MCSGP: Internal UV profiles of both UV detectors shown for 5 cycles shown ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
14 Case Study: multiple MCSGP cycles overlay Online evaluation of MCSGP experiment: Cycle overlay can be used to determine if run has reached cyclic steady state and shows a consistent pattern Example: Overlay of 5 cycles: Exact matching of product profiles in (blue) window. Cyclic steady state: Product of constant quality and concentration is withdrawn Product consistency shown product elution ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
15 concentration (normalized) Example: MCSGP for -3 fatty acid ethyl ester production (EPA-EE) Result chromatograms Feed Product W-fraction S-fraction Impurity FA-EE EPA-EE (> 97% pure) DHA-EE Overlay of analytical reversed phase chromatograms of feed and fractions from MCSGP Feed: Ratio EPA/DHA= 4: Time [min] ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
16 MCSGP for -3 fatty acid ethyl ester production (EPA-EE) Process for production of > 97% purity EPA-EE developed based on reverse phase chromatography with Ethanol as solvent Conceptual design study for 100t/a production with renowned engineering company completed Resin & solvent cost reduction of 80% with respect to batch chromatography MCSGP (20 m resin) Batch (15 m resin) Purity [%] >97% >97% Yield [%] 90% 36% + 250% Improvement by MCSGP Productivity (Throughput) [(g product)/(l resin)/(hr operation time)] Solvent Consumption [L solvent/g product] % % ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
17 Purification of EPA: Scale-Up modelling Contichrom (2 col MCSGP) lab-scale (for feasibility) Pilot-scale (500 kg/year) Productionscale (45 t/year) i.d. 4.5cmx15cm columns, 50mL/min pumps, 60kg/year i.d. 12.5cmx15cm columns, 25L/hr pumps 500 kg/year solvent: 58m 3 /month i.d. 120cmx15cm columns, 2 500L/hr pumps 45 t/year solvent: 5 250m 3 /month Detailed assumptions of scenario: (Feed purity 60%) Batch chromatography: Load: 1 g/l Yield: assume 100% Run time per batch 1hr Productivity (PR): 2 [(g purified product) / (L stationary phase) / (hr operating time)] Solvent consumption (SC): 7 [(liter solvent)/(g purified product)] Ref: MCSGP: Assumption: MCSGP productivity 10x batch productivity, -80% solvent consumption MCSGP: PR=20 [g/l/hr], SC=1.4 [L/g] Batch i.d. 55cmx25cm column, 600L/hr pumps 500 kg/year solvent: 290m 3 /month i.d. 500cmx15cm column, L/hr pumps 45 t/year solvent: m 3 /month Column size not feasible in batch ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
18 Conclusions from cost modelling of EPA purification Batch chromatography not feasible on production scale MCSGP production scale: 45 t/y could be feasible Pilot-scale MCSGP could provide clinical material and initial market supply (500kg/y) ChromaCon AG // Purification of fatty acids with Contichrom // // ver. May
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