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Application Book Volume 4 Biodiesel Quality Control Application Book Volume 4 Biodiesel Quality Control Contents

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Application Book Volume 4 Biodiesel Quality Control Application Book Volume 4 Biodiesel Quality Control Contents SEG-A-081 Quality Control According to DIN EN 14103, 14105, 14110 Application Book Volume 4 Biodiesel Quality Control Application Book Volume 4 Biodiesel Quality Control Contents I. Determination of methanol in biodiesel 5 II. Fatty acid methyl esters (FAME) Determination of total ester content and linolenic acid methyl ester contents 9 III. Determination of glycerol and glycerides 14 Part 1: Introduction and sample preparation 15 Part 2: Instrument configuration 17 Part 3: Optimization of the gas chromatographic method 20 Part 4: Signal identification 22 Part 5: Evaluation and quantification 25 Application Book Volume 4 Biodiesel Quality Control Publisher: Shimadzu Europa GmbH Albert-Hahn-Str. 6-10 · 47269 Duisburg, Germany Telephone: +49 (0) 203 7687-0 Telefax: +49 (0) 203 766625 Email: [email protected] Internet: www.shimadzu.eu Editorial Office: Uta Steeger · Phone: +49-203-7687-410 Ralf Weber, Angela Bähren Design and Production: m/e brand communication GmbH GWA , Düsseldorf © Copyright: Shimadzu Europa GmbH, Duisburg. Reprint, in whole or in part, is subject to the permission of the editorial office. Windows is a Trademark of Microsoft Corporation. 5 I. METHANOL Biodiesel quality control according to DIN EN 14110 Determination of methanol in biodiesel A 1 1 H2C – O – CO – R H2C – O – H H3CO – CO – R P A PB 2 CH3OH 2 HC – O – CO – R HC – O – H H3CO – CO – R B 3 3 H2C – O – CO – R H2C – O – H H3CO – CO – R Triglyceride Glycerine FAME (Biodiesel) Figure 1: Equilibrium reaction of the transesterification of plant oils A B (triglycerides) to fatty acid methyl esters (biodiesel) iodiesel production has Figure 2: Equilibrium between the liquid- and gas-phase during headspace increased considerably in sample preparation. Although component A is present at a lower concentration B Europe in recent years. in the liquid phase, the concentration ratio in the gas-phase may shift, depend- In 1996, production was nearly ing on the vapor pressure of the individual components. Correspondingly, the 0.5 million tonnes. Today, the chromatograms resulting from headspace injection usually produce different production capacity is much signal ratios when compared with those resulting from liquid sample injection. higher. This development has also been supported by the automo- bile industry. In fact, several mil- The DIN EN 14214 standard ages (% m/m). DIN EN 14110 lion passenger cars and commer- specifies all legal limits for possi- describes the required method for cial vehicles have been approved ble by-products. For safety-relat- methanol determination. by their manufacturers to run on ed reasons and in order to com- System with headspace biodiesel fuel or higher biodiesel ply with requirements of the GC with headspace autosampler for high precision blends with mineral diesel. Com- automobile industry, the legal injection results pliance with the European Bio- limit for methanol residue has diesel standard DIN EN 14214 been defined as 0.2 mass percent- Biodiesel can consist of up to 100 Requirements of DIN EN 14110 ensures a continuously high qual- different fatty acid methyl esters, exceeded ity level. depending on the plant oils used during production. For the deter- The production of biodiesel is mination of methanol in such a based on transesterification of complex matrix, gas chromatog- plant oils or animal fats to fatty raphy in combination with acid methyl esters (FAME, Fig- headspace injection is the recom- ure 1). At a temperature of mended method. This enables approximately 60 °C, the plant separation of low-boiling point oil, consisting mainly of glycerin methanol from the high-boiling esters, is esterified using point fatty acid methyl esters methanol and a catalyst (alkali already during the sample prepa- hydroxide or alkali alcoholate). ration step. In order to quantitatively shift the equilibrium reaction towards The biodiesel samples are heated the biodiesel or FAME side, in a gas-tight 20 mL vial. Metha- methanol is added in excess. nol is a low-boiling point com- pound and is enriched in the After the reaction is finished, gas-phase while the high-boiling the excess methanol together point compounds remain in the with several by-products must liquid phase (Figure 2). After a be removed. Figure 4: GC-2014 and HT200H specific time, equilibrium is 6 Biodiesel quality control according to DIN EN 14110 I. METHANOL reached and a constant volume can be sampled from the gas- 4.0 5.0 3 uV (x 100,000) Y = aX + b phase (headspace) of the vial and a = 4,601507e-002 b = 0.0 injected into the GC system. 3.5 4.0 R^2 = 0.9999938 2-Propanol R = 0.9999969 Calibration with minimum 3.0 3.0 complexity 2.5 Since the biodiesel matrix can 2.0 influence the equilibrium Concentration Ratio 2.0 2 between the methanol concentra- 1.0 tions in the liquid- and gas-phase, 1.5 calibration standards must be 0.0 prepared in methanol-free Methanol 0.0 2.5 5.0 7.5 10.0 1.0 biodiesel. The DIN EN 14110 Area Ratio biodiesel standard recommends preparation of a calibration curve 0.5 containing 0.01, 0.1 and 0.5 % Figure 5: Calibration curve of methanol in biodiesel in accordance with DIN EN (m/m) methanol in FAME. An 0.0 14110 using internal standard calibration internal standard should always be used when applying manual 0.0 2.5 5.0 7.5 Sample 1 2 3 headspace injection. When using a headspace autosampler, an Minutes Average concentration % (m/m) 0.009 0.100 0.500 internal standard will not be Reproducibility standard 0.00005 0.00100 0.00485 necessary but is, however, recom- deviation % (m/m) mended to increase the reliability Figure 3: Chromatogram of 0.01 % Reproducibility % RSD 0.54 0.99 0.97 of the results. The additional (m/m) methanol in biodiesel. 2-pro- work is kept within reasonable panol was added as internal standard. Table 1: Biodiesel sample spiked with three different methanol concentrations. limits: to each standard and Table 1 shows the reproducibility over 6 measurements of the same sample each biodiesel sample, 5 µL of using the same method on the same instrument. 2-propanol is added (Figure 3). a given time. The autosampler prepares several samples simulta- All measurements are carried out neously to ensure the highest At a methanol concentration of content were spiked with variable on a Shimadzu GC-2014AFsc possible sample throughput and 0.01 % (m/m) a signal-to-noise amounts of methanol. system in combination with the to prevent hold-up at the gas ratio of higher than 2000 :1 was HT200H headspace autosampler chromatograph. A gas volume of obtained. Thus, the technique Samples with the lowest concen- (Figure 4). Both instruments are 500 µL is sampled from the offers many options for improve- trations showed the highest dif- easy to operate and designed for headspace of each vial and inject- ments via application of larger ference of two out of six meas- daily routine analysis. ed into the GC-2014AFsc system split ratios or faster chromato- urement values 0.00012 % (m/m). with a split ratio of 1:10. graphic separation. DIN EN 14110 allows for For the calibration, 5 g of the 0.00151 % (m/m), a ten-fold respective standard solution as Additional parameters are recom- Results exceeding the higher deviation. well as 5 µL of 2-propanol are mended according to DIN EN standard requirements added to a 20 mL headspace 14110: The combination of the HT200H crimp vial. Corresponding to 5 g Temperature split injector: The calibration curve in Figure 5 and GC-2014AFsc offers an effi- of biodiesel sample, 5 µL of 150 °C demonstrates that the combina- cient as well as accurate automa- 2-propanol is added as internal Column oven (isothermal): tion of the HT200H autosampler tion solution for the routine anal- standard. The HT200H can han- 50 °C and the GC-2014 results in high ysis for methanol determination dle up to 40 sample vials per tray. Flame ionization detector: linearity over the concentration in biodiesel. Smaller scale bio- 150 °C range recommended in DIN EN diesel producers will profit from Automated sample Carrier gas (helium) linear 14110. Reproducibility of the this robust analytical system with preparation velocity: 35 cm/s measurement values for biodiesel its excellent price/performance Separation column used for samples is higher than the ratio. Sample preparation is fully auto- the measurements: requirements according to DIN mated, whereby each sample is Restek, Stabilwax-DA 30 m, EN 14110 (Table 1). Biodiesel shaken and heated to 60 °C for 0.32 mm, df 1.0 µm samples with very low methanol 7 9 II. FAME Biodiesel quality control according to DIN EN 14103 Fatty acid methyl esters (FAME) Figure 1: Structural formula for linolenic acid methyl ester Determination of total ester content and linolenic (methyl cis,cis,cis-9,12,15-octadecatrienoate) n the last years, biofuels have linolenic acid methyl ester is also fatty acid methyl esters in the become well established as determined. While this compound range from C4:0 up to C24:1. I an independent source of is a welcome essential acid in sal- energy in the industrial countries. ad oils, it is an interfering reactive The chromatogram in Figure 3 The percentage of biofuels in the compound in biodiesel that might shows the complete separation energy mix is expected to in- influence long-term stability of except for C4:0 and the oleic acid crease considerably within the biodiesel. methyl ester C18:1 cis/trans iso- next 10 years in order to reduce mers. The chromatogram time dependency on fossil fuels and to Instrumentation and can be reduced drastically since maintain energy prices at long- measurement a complete separation of all fatty term affordable levels.
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