Selective Extraction And Analysis of Chemical Migrants from Packaging Material using a Supercritical Fluids (SFE) Guy Wilson E&L 2015
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1 Selective Extraction And Analysis of Chemical Migrants from Packaging Material using a Supercritical Fluids (SFE) Guy Wilson E&L Waters Corporation 1
2 Regulatory aspects The pharmaceutical drug companies have to prove that nothing harmful gets transferred from the packaging into drug product. Or that whatever does leach into sample is below the thresholds established by the guidelines. For food industry only certain chemicals must be checked/monitored e.g. bisphenols A, B and E, phthalates. But other have to be determined as well. Under the Federal Food, Drug, and Cosmetic Act, cosmetic products and ingredients do not require FDA approval before they go on the market. The exception is color additives. FDA periodically buys cosmetics and analyzes them, especially if aware of a potential problem. The information obtained can be used to alert consumers, support regulatory actions, or issue guidance for industry. FDA does not have the resources to sample and analyze all cosmetics on the market Waters Corporation 2
3 Typical extractables & leachables Chemical additives, plasticizers, antioxidants and contaminants present in individual polymers Monomers and oligomers from incomplete polymerization reactions Volatile compounds from the secondary packaging such as inks and adhesives Residual compounds from the surfaces of the molding equipment, antistatics etc 2015 Waters Corporation 3
4 Sample Preparation Major Source of Laboratory Costs Sample preparation is the most often cited area of improvement to save time and operating costs Most sample preparation involves being in an organic phase Liquid/Liquid, PPT, Soxhlet, Distillation, Evaporation and Reconstitution Many matrices will respond best to organic phases (gels, blisters, ointments, synthesis solvents, etc.) image from dyapharma.com image from sefetec.net image from tasnee.com 2015 Waters Corporation 4
5 Comparison study of 4 different extractions techniques Compare 4 different extraction techniques of 4 common packaging materials : o Liquid extraction Water o Microwave Hexane, Isopropanol o Soxhlet Hexane, Isopropanol Compare extraction profiles of the same packaging materials by using UPC² (SFC) o Supercritical Fluid Extraction (SFE) Isopropanol 2015 Waters Corporation 5
6 Samples High Density Polyethylene bottle (HDPE) Low Density Polyethylene container (LDPE) Ethylene Vinyl Acetate plasma bag (EVA) Polyvinyl Chloride blister pack (PVC) Analytes : o Irgafos 168, 5-chloro-2-hydroxy-4-methylbenzophenone (5-Cl-2-OH-4- methyl BP), 4-hydroxy-2-octyloxybenzophenone (4-OH-2-octyloxy BP), Irganox 245, Lowinox 44B25, Naugard 445, Diphenyl phthalate, Tinuvin 328, Uvitex OB 2015 Waters Corporation 6
7 Extractions conditions Microwave extraction 2g sample 1 cm² pieces Teflon Vessel Water extraction 2g sample 1 cm² pieces 20 ml Headspace Vial Soxhlet 3 g of PVC 5 g of HDPE, LDPE, and EVA 1 cm² pieces Whatman 33 mm x 94mm cellulose extraction thimble 10 ml Hexane + stirrer and heating element 10 ml IPA + stirrer 20 ml Water 175 ml Hexane 175 ml IPA 3 hours 50 C 3 hours 50 C 72 hours 50 C 8 hours 8 hours Dry 15mL Hexane Dry 15mL IPA 2015 Waters Corporation 7
8 Supercritical Fluid Extraction (SFE) 2015 Waters Corporation 8
9 What Is Supercritical Fluid Extraction Supercritical Fluid Extraction is the process of separating one or multiple components (the extractant) from another (the matrix) using supercritical fluids as the extracting solvent. Extraction is usually from a solid matrix SFE can be used as : a sample preparation step for analytical purposes or on a larger scale to either strip unwanted material from a product (e.g. decaffeination) or collect a desired product (e.g. essential oils). Carbon dioxide (CO 2 ) is the most used supercritical fluid, sometimes modified by cosolvents such as ethanol or methanol. > 31 C and 74 bar (1073 psi) It is based on the principle that solubility in a supercritical fluid increase dramatically with increasing density, and different solutes have different solubility at the same condition Waters Corporation 9
10 Why A Supercritical Fluid? Why do Supercritical fluids make good mobile phases for chromatography? Diffusivity describes the rate at which one substance can move through another Viscosity is resistance to flow High diffusivity, and low viscosity combine in SFC to give fast, efficient chromatography 2015 Waters Corporation 10
11 Supercritical Fluid Applications Chromatography (SFC) Analysis & Purification Chiral Separation Normal Phase SF Particle Design (RESS & SAS) Polymerization Cristallization Impregnation Supercritical CO2 Extraction (SFE) Bioactive compounds Nutraceuticals Spices and aromatic Decaffeination Decontamination or cleaning Valuable molecules from waste Reaction Hydrogenation Hydroformylation Carboxylation 2015 Waters Corporation 11
12 Why A Supercritical Fluid? 2015 Waters Corporation 12
13 Extractability Based on Polarity Nonpolars Alkanes Neat CO 2 Ethers Esters Alcohols Amides Increasing Polarity Acids Amines Highly polar organics SFE Inorganic ions CO 2 + modifier CO 2 + modifier + ternary additives CO 2 + modifier + ternary additives + water Liquid based extraction methods Small molecules Peptides Large proteins Increasing Molecular Weight One of the largest advantages of SFE: Selectivity 2015 Waters Corporation 13
14 Advantages of SFE: Increased selectivity and specificity Fine tune the extraction with changes in co-solvents (Method Dev) Decreased cost per sample Minimal procurement or disposal cost of CO 2 in comparison to organic solvents Improves extraction efficiency and reduces extraction time vs. other sample preparation techniques Minimize exposure to organic solvents Lack of residual organic solvents Is environmentally friendly Accelerate the extraction process Extract analytes faster than comparative techniques Eliminate cumbersome traditional solid/liquid extraction (ie. Sohxlet or solvent soak) Ability to handle thermally labile compounds Operates at lower temperatures than PSE, MAE and soxhlet 2015 Waters Corporation 14
15 Instrumentation An extraction technique complementary/alternative to Soxhlet or liquid/liquid extraction CO 2 in combination with an organic solvent, most commonly alcohols, is used as the extraction solvent 2015 Waters Corporation 15
16 Extraction Modes Extractions are done in dynamic, static, or combination modes. In a dynamic extraction the supercritical fluid continuously flows through the sample in the extraction vessel and out the restrictor to the trapping vessel. In static mode the supercritical fluid is held in the extraction vessel for some period of time before being released through the restrictor to the trapping vessel. In combination mode, a static extraction is performed for some period of time, followed by a dynamic extraction Waters Corporation 16
17 SFE conditions Microwave extraction Water extraction Soxhlet Supercritical Fluid Extraction 2g sample 2g sample 3 g of PVC 5 g of HDPE, LDPE, and EVA 2 g of PVC 3 g of HDPE, LDPE, and EVA 1 cm² pieces 10 ml Hexane 10 ml IPA 20 ml Water 175 ml Hexane 175 ml IPA CO 2 :IPA 98:2 4.9 ml/min CO ml/min IPA CO 2 :IPA 80:20 4 ml/min CO ml/min IPA 3 hours 50 C 3 hours 50 C 72 hours 50 C 8 hours Dry 15mL Hexane 8 hours Dry 15mL IPA 2 X 50 C & 300 Bars 30 min Dynamic 20 min Static 10 min Dynamic Dry 10 ml IPA for PVC, 9 ml IPA for HDPE, LDPE, and EVA 2015 Waters Corporation 17
18 What About The Analysis? 2015 Waters Corporation 18
19 Supercritical Fluid Chromatography 2015 Waters Corporation 19
20 Broad Applicability Courtesy of A. Grand-Guillaume Perrenoud, D. Guillarme, Pr J-L. Veuthey, University of Geneva 2015 Waters Corporation 20
21 The ACQUITY UPC2 Splitter PDA detector Column Manager Make-up Pump Mass Spec Auxiliary Inject valve Back Pressure Regulator (Dynamic and Static) Inject valve mixer Thermo-electric heat exchanger Waste Modifier 2015 Waters Corporation CO2 Supply CO2 Pump Modifier Pump 21
22 UPC2: Compatibility with all MS Technologies For ultimate CC-MS performance, ACQUITY UPC2 System coupled with: ACQUITY QDa - Single quadrupole detector for robust and routine performance Xevo TQ-S - Ultimate sensitivity Xevo G2-S Qtof and Synapt G2-S - Qualitative and quantitative results from a single platform 2015 Waters Corporation 22
23 Workflow Benefit of ACQUITY UPC 2 for the Analysis of Polymer Extracts Polar Solvent Extraction Non-Polar Solvent Extraction Inject direct on LC Inject direct on GC Back-extract with a nonpolar solvent for GC injection Evaporate and reconstitute in a more polar solvent for LC injection Polar or Non-Polar Extraction Inject direct On UPC Waters Corporation 23
24 Chromatographic separations AU UPC 2 BHT 5-Cl-2-OH-4-methyl BP Tinuvin P Tinuvin 328 Irgafos OH-4-octyloxy BP Irganox 1076 Diphenylphthalate Uvitex OB Naugard 445 Irganox 1330 Irganox 1010 Irganox 245 Lowinox 44B25 4 min separation by UPC 2 vs. 9.5 min by UPLC Minutes AU UPLC Tinuvin P 5-Cl-2-OH-4-methyl BP Diphenyl phthalate BHT Irganox 245 Lowinox 44B25 4-OH-2-octyloxy BP Uvitex OB Naugard 445 Tinuvin 328 Irganox 1076 Irganox 1330 Irganox 1010 Irgafos Minutes Waters Corporation 24
25 UPC 2 results - Microwave and Water extraction profiles for LDPE Column Name: 2-EPSampleName: LDPEhex mw Date Acquired: 9/6/2012 3:47:25 PMEDT Instrument Method Id: 1953 Injection Id: AU Hexane Column Name: 2-EPSampleName: LDPEIPA mw Date Acquired: 9/6/2012 5:50:59 PMEDT Instrument Method Id: 1953 Injection Id: AU IPA Column Name: 2-EPSampleName: LDPEwater Date Acquired: 9/6/2012 7:42:54 PM EDT Instrument Method Id: 1953 Injection Id: AU Water Minutes 2015 Waters Corporation 25
26 Soxhlet and Microwave IPA extractions Soxhlet Microwave Column Name: 2-EP SampleName: PET IPA sox Date A cquired: 9/6/2012 7:01:40 PM EDT Instrument Method Id: 1953 Injection Id: Column Name: 2-EP SampleName: PET IPA mw Date Acquired: 9/6/2012 6:14:33 PM EDT Instrument Method Id: 1953 Injection Id: 2129 PVC PVC Column Name: 2-EP SampleName: EV A IPA sox Date Acquired: 9/6/2012 6:49:54 PM EDT Instrument Method Id: 1953 Injection Id: 2162 Column Name: 2-EP SampleName: EVA IPA mw Date Acquired: 9/6/2012 6:02:46 PM EDT Instrument Method Id: 1953 Injection Id: EVA EVA Column Name: 2-EP SampleName: LDPE IPA sox Date Acquired: 9/6/2012 6:38:07 PM EDT Instrument Method Id: 1953 Injection Id: 2151 Column Name: 2-EP SampleName: LDPE IPA mw Date Acquired: 9/6/2012 5:50:59 PM EDT Instrument Method Id: 1953 Injection Id: LDPE LDPE Column Name: 2-EP SampleName: HDPE IPA sox Date Acquired: 9/6/2012 6:26:20 PM EDT Instrument Method Id: 1953 Injection Id: 2140 Column Name: 2-EP SampleName: HDPE IPA mw Date Acquired: 9/6/2012 5:39:12 PM EDT Instrument Method Id: 1953 Injection Id: 2096 HDPE HDPE Minutes Minutes 2015 Waters Corporation 26
27 SFE extracts Low IPA High IPA Column Name: 2-EP SampleName: PET low IPA SFE Date Acquired: 9/6/2012 9:05:18 PM EDT Instrument Method Id: 1953 Injection Id: PVC Column Name: 2-EP SampleName: PET high IPA SFE Date Acquired: 9/6/2012 9:52:24 PM EDT Instrument Method Id: 1953 Injection Id: PVC Column Name: 2-EP SampleName: EVA low IPA SFE Date Acquired: 9/6/2012 8:53:32 PM EDT Instrument Method Id: 1953 Injection Id: EVA Column Name: 2-EP SampleName: EV A high IPA SFE Date A cquired: 9/6/2012 9:40:39 PM EDT Instrument Method Id: 1953 Injection Id: EVA Column Name: 2-EP SampleName: LDPE low IPA SFE Date Acquired: 9/6/2012 8:41:45 PM EDT Instrument Method Id: 1953 Injection Id: LDPE Column Name: 2-EP SampleName: LDPE high IPA SFE Date Acquired: 9/6/2012 9:28:52 PM EDT Instrument Method Id: 1953 Injection Id: LDPE Column Name: 2-EP SampleName: HDPE low IPA SFE Date Acquired: 9/6/2012 8:29:57 PM EDT Instrument Method Id: 1953 Injection Id: HDPE Minutes Column Name: 2-EP SampleName: HDPE high IPA SFE Date Acquired: 9/6/2012 9:17:05 PM EDT Instrument Method Id: 1953 Injection Id: 2299 HDPE Minutes 2015 Waters Corporation 27
28 LDPE, all IPA extracts AU Column Name: 2-EP SampleName: LDPE high IPA SFE Date Acquired: 9/6/2012 9:28:52 PM EDT Instrument Method Id: 1953 Injection Id: High IPA SFE AU Column Name: 2-EP SampleName: LDPE low IPA SFE Date Acquired: 9/6/2012 8:41:45 PM EDT Instrument Method Id: 1953 Injection Id: Low IPA SFE Column Name: 2-EP SampleName: LDPE IPA sox Date Acquired: 9/6/2012 6:38:07 PM EDT Instrument Method Id: 1953 Injection Id: 2151 AU Soxhlet Column Name: 2-EP SampleName: LDPE IPA mw Date Acquired: 9/6/2012 5:50:59 PM EDT Instrument Method Id: 1953 Injection Id: AU Microwave Minutes 2015 Waters Corporation 28
29 UV chromatogram of LDPE SFE extract analysed by UPC I r g a f o s I r g a n o x I r g a n o x Minutes 2015 Waters Corporation 29
30 Confirmation of identity using MS In te ns ity 3.5x x x x x x x10 5 Peak in LDPE extract Intensity Combined - SQ 1: MS Scan 1: ES+, Centroid, CV=Tune 2.0x x x x x x x x x x m/z x x Minutes Peak from Irganox 1076 std 2.2x x x x10 7 Combined - SQ 1: MS Scan 1: ES+, Centroid, CV=Tune In te n s ity 6.0x x10 6 Intensity 1.4x x x x x x x x m/z Minutes 2015 Waters Corporation 30
31 Conclusion All extraction techniques provided similar extractables profiles, but SFE consumes much less solvent and is quicker than Soxhlet extraction. The MV-10 SFE System has automated method development and extractions on 10 samples to simplify the process. UPC 2 gives a fast, high resolution separation and has wide sample diluent compatibility Waters Corporation 31
32 Thank You! 2015 Waters Corporation 32
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