Application of Design of Experiment (DOE) to the Simultaneous GC FID/MS Analysis of Monocarboxylic Acids and Glycerides in Biofuels

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1 Application of Design of Experiment (DOE) to the Simultaneous GC FID/MS Analysis of Monocarboxylic Acids and Glycerides in Biofuels G. Baglayeva Jana Šťávová, B. Diepp, E. Hellrung, W. Seames, and A. Kubátová Chemistry Department

2 Biofuels Alternative, sustainable source of energy obtained from biomass or plant oils OCOR 1 CHOCOR 2 OCOR 3 Triacylglyceride Cannot be used as liquid fuels: Not stabile Highly viscous Form carbon deposits in parts of engines upon combustion TAG 2

3 Products of vegetable oil cracking OCOR 1 CHOCOR 2 OCOR 3 T, C (catalyst) Hydrocarbons (alkanes, cycloalkanes, aromatics) Undesirable by products in biofuels Triacylglyceride TAG OH OH OH CHOCOR 2 + CHOH + CHOH problem during storage injector deposits filter and fueling systems clogging OCOR 3 OCOR 3 OH Diacylglyceride Monoacylglyceride glycerol DAG MAG corrosive highly viscous cause engines & fuel tanks damage Monocarboxylic acids (MCA) 3

4 The degree of purity and the type and amounts of contaminants present in biofuel need to be known prior to its use! 4

5 Standard methods for quantitative determination of contaminants in biofuels ASTM D 664 Acid number by potentiometric titration ASTM D 6584 MAGs, DAGs, TAGs and glycerol by gas chromatography No detailed characterization of individual species Biofuel production process Product safety / storage control 5

6 Research objectives To develop a method for simultaneous analysis detailed identification quantification of monocarboxylic acids (C 4 C 18 ), monoglycerides (C 16, C 18 ), diacylglycerides (C 16, C 18 ), triacylglycerides (C 7 22 ) and glycerol 6

7 Instrumentation Agilent 7890 GC-FID/5975 MS Gas Chromatograph Programmed Temperature Vaporization (PTV) injector A 15 m long high temperature non polar column The Flame Ionization Detector (FID) for quantification / PDF (accessed on 2/8/2008). The Mass Spectrometry (MS) detector for identification 7

8 Challenge Wide molecular weight range of analytes ( amu) Possible loss of the compounds: 1. Incomplete vaporization 2. Incomplete transfer Injection parameters: 1. Inlet temperature program (PTV) 2. Splitless time (Splitless) 3. GC oven temperature program (Column) 8

9 Optimization of injection conditions Traditional method One Variable At a Time: Design of experiments: Time and reagent consuming Only main factors can be evaluated interactions are not considered Several variables at a time Minimum number runs Factors + interactions 9

10 Central composite design Cube points (factorial points) 1 and +1 coded levels Axial points 1.68 and coded levels Coded values Splitless time, min o Center point all parameters at 0 coded value 10

11 Central composite design randomized run order eliminate effects of unknown Replicates, batch to batch variability 8 factorial runs 6 axial runs x 2blocks 6 replicates of central point 40 runs Repeatability of experimental resolution Run order PTV hold up time at initial 40 C, min Uncoded levels Splitless time, min Oven hold up time at initial 35 C, min

12 Significance of parameters Factor or interaction was considered to be influential if P value 0.05 Source Main factors Target compounds MCA TAG C 4 C 5 C 6 C 7 C 8 C 9 C 10 C 15 C 16 C 17 C 18 C 10 C 16 C 18 PTV Splitless Column Interactions PTV Splitless PTV Column Splitless Column "PTV" stands for injection hold up time at initial 35 C, min; "Splitless" stands for splitless time, 12 min; Column stands for oven temperature hold up time at initial 35 C, min

13 (A) Peak area 3.E+08 3.E+08 2.E+08 2.E+08 1.E+08 5.E+07 Effects of main parameters MCA_C05 MCA_C08 MCA_C09 MCA_C10 PTV hold up time at initial 40 C, min shown for monocarboxylic acids only (B) Peak area 4.E+06 MCA_C15 MCA_C16 3.E+06 MCA_C17 MCA_C18 2.E+06 1.E+06 PTV hold up time at initial 40 C, min 0.E (C) 4.E+08 MCA_C07 MCA_C08 (D) 4.E+06 MCA_C15 MCA_C16 3.E+08 MCA_C09 MCA_C10 3.E+06 MCA_C17 MCA_C18 Peak area 2.E+08 1.E+08 Peak area 2.E+06 1.E+06 0.E+00 Splittless time, min E+00 Splittless time, min

14 Effect of interactions Response surface methodology MCA C 5 MCA C 7 MCAs C 8 C 18 TAG C 8 C 22 To predict the best combination of factors which provides maximum response (taking into account effects of individual parameters) To choose the most favorable injection conditions Optimum ranges Selected conditions Injection hold up time at initial (40 C) temperature, min Splitless time, min Oven hold up time at initial (35 C) temperature, min

15 Additional parameters evaluated Derivatization conditions using MSTFA (N Methyl N (trimethylsilyl)trifluoroacetamide) GC oven temperature program MS acquisition parameters Inter day repeatability Intra day repeatability Method validation Limits of detection 15

16 Standard mixture TIC Abundance MCA C 4 18 TAG MAG C 16, C 18 DAG C 16, C 18 TAG C 16, C 18 FID 0 Time--> Abundance Time-->

17 Abundance Time--> Partially cracked soybean oil FID MCA C11, TMS MCA C12, TMS MAG C16, TMS TAG C56 MCA C14, TMS IS 2 DAG C16, TMS DAG C16+18, TMS DAG C18, TMS IS1 MCA C4, TMS MCA C5, TMS RS 3 MCA C6, TMS MCA C7, TMS MCA C8, TMS MCA C10, TMS RS 6 TAG C50 (C16+C16+C18) TAG C54 TAG C52 RS 4 RS1 RS2 MCA C16, TMS MCA C18, TMS RS Target analytes Average % [w/w] SD Total monocarboxylic acids (MCA) Glycerol, TMS ether ND NA Total monoacylglycerides, TMS ethers (MAG) Total diacylglycerides, TMS ethers (DAG) Total triacylglycerides (TAG) Total

18 Conclusions A method was applied to partially cracked soybean oil samples Parameters evaluated: Injection, derivatization, GC oven temperature program and MS parameters A method was developed 18

19 Acknowledgments Dr. Wayne Seames, Professor of Chemical Engineering, University of North Dakota Danese Stahl, Research Chemist, UND Chemistry Dept. The North Dakota EPSCoR Program The North Dakota Sustainable Energy Research Initiative (SUNRISE) The North Dakota Soybean Council The North Dakota State Board of Agricultural Research and Education The U.S. Department of Energy The U.S. Federal Aviation Administration UND Chemistry Department 19

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