Determination of Carbonyl Compounds in Vehicle Cabin Compartments
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1 Determination of arbonyl ompounds in Vehicle abin ompartments Liu Lvye, Yuan Bin, Xu Qun, Jin Yan, Liang Lina, and Jeffrey Rohrer Thermo Fisher Scientific, Shanghai, People s Republic of hina; Thermo Fisher Scientific, Sunnyvale, A, USA Application Note 056 Key Words DNP Derivatives, Aldehyde and Ketone ompounds Analysis, Environmental Analysis, Air Quality, Air Monitoring, PL Goal To develop an efficient high-performance liquid chromatography (PL) method for the sensitive determination of,4-dinitrophenylhydrazine (DNP)-derivatized carbonyl compounds in vehicle cabin air samples. The target analytes those specified in alifornia Air Resources Board (ARB) Method No. 004, International rganization for Standardization (IS) :0, U.S. Environmental Protection Agency (EPA) ompendium Method T-A, and the hinese J/T are formaldehyde, acetaldehyde, acetone, acrolein, propionaldehyde, crotonaldehyde, methyl ethyl ketone, methacrolein, hexanaldehyde, butyraldehyde, benzaldehyde, valeraldehyde, and m-tolualdehyde. Introduction Many carbonyl compounds are known to cause adverse effects on human health and thus have been listed by the U.S. EPA in the ealth Effects Notebook for azardous Air Pollutants. For example, acetaldehyde and formaldehyde are considered probable human carcinogens; inhalation of acrolein may result in upper respiratory tract irritation and congestion; and exposure to high levels of propionaldehyde increases the risk of liver damage and may cause people to choke, pass out, or suffocate. People are subject to toxic exposure during the manufacture of these carbonyl compounds, which are widely used in large quantities in vehicle manufacturing. arbonyl compounds can also be hazardous to human health through the direct or indirect release of harmful toxins into vehicle passenger cabin compartments. People in modern society now spend more time in vehicles due to lengthy commutes, long-distance travel, and frequent traffic jams. Therefore, it is important to establish effective methods for the determination of carbonyl compounds found in the air inside vehicle cabins. Because the carbonyl compounds of interest are volatile, it is preferable to derivatize them into a nonvolatile, stable form. This reduces the possibility of analyte loss and allows a sample to be analyzed later rather than immediately. The main techniques for the determination of carbonyl compounds are spectrophotometry, gas chromatography (G), and PL. In the spectrophotometric method, hydroxylamine hydrochloride solutions have been used to extract carbonyl compounds from samples via the formation of less-volatile oxime derivatives. The total oxime derivatives were detected at a wavelength of nm and the conjugated diene carbonyl oximes were detected at 7 nm. This method show limited selectivity and sensitivity.,3 ompared to the spectrophotometric method, G and PL techniques are more frequently used and some standard methods have been created. 4- For example, EPA Methods and contain PL/UV and G/electron-capture detection (ED) methods using DNP and o-(,3,4,5,6-pentafluorobenzyl)-hydroxylamine (PFBA) as derivatization reagents, respectively, to determine the carbonyl compounds in drinking water. As a derivatization reagent, DNP has been extensively used with carbonyl compounds due to its high reactivity, selectivity, and stability. It is used for G with ED and mass spectrometry (MS), 3 PL with UV, 6-0,4,5 fluorescence, 6 and MS. 7,8 Reaction with DNP yields a chromophore with an absorption maximum of 360 nm. This provides highly sensitive and selective detection of carbonyl compounds that is particularly suitable for PL with UV detection.
2 ARB Method 004 reports an PL/UV method for the determination of 3 carbonyl compounds (structures shown in Figure ) generated from automotive source samples. 9 In this method, DNP-impregnated cartridges are used for sampling. After conversion to the DNP derivatives, the carbonyl compounds are analyzed by PL with UV detection. 3 3 Methyl Ethyl Ketone 3 ( ) 3 exanaldehyde 3 Butyraldehyde 3 3 Acetone Figure. Structures of carbonyl compounds specified in ARB Method 004. Equipment Two Thermo Scientific Dionex UltiMate 3000 RSL systems were used in this study.* System included: 3 rotonaldehyde Acrolein m-tolualdehyde LPG-3400RS Quaternary Pump with SRD-3400 Integrated Solvent and Degasser Rack WPS-3000TRS Wellplate Sampler, Thermostatted, with 00 µl sample loop T-3000RS Thermostatted olumn ompartment DAD-3000RS Diode Array Detector with 3 µl flow cell System included: PG-3400RS Binary Pump with Solvent Selector Valves and SRD-3400 Integrated Solvent and Degasser Rack WPS-3000TRS Wellplate Sampler, Thermostatted, with 5 µl sample loop T-3000RS Thermostatted olumn ompartment DAD-3000RS Diode Array Detector with.5 µl flow cell Thermo Scientific Dionex hromeleon hromatography Data System software 6.80 SR9 or higher *All work can be performed using any UltiMate 3000 system with a compatible sample loop and flow cell. Benzaldehyde 3 Propionaldehyde 3 Formaldehyde 3 Valeraldehyde Methacrolein 3 Acetaldehyde 3 Reagents and Standards Deionized (DI) water, 8. MΩ-cm resistivity Methanol ( 3 ), PL Grade 99.9% (Fisher Scientific P/N A ) Acetonitrile ( 3 N), PL Grade 99.9% (Fisher Scientific P/N A ) Tetrahydrofuran (TF), PL Grade 99.8% (Fisher Scientific P/N A ) Aldehyde/Ketone-DNP Stock Standard-3, 3 omponents in Acetonitrile for ARB Method 004, 3 µg/ml of each component (erilliant P/N ERA-03K) onsumables Thermo Scientific Target Nylon Syringe Filters, 0.45 μm, 30 mm (Fisher Scientific P/N F500-) Working Standard Solutions for alibration Prepare six working standard solutions for the calibration with 0.03, 0.06, 0.5, 0.30, 0.60, and.50 µg/ml concentrations by adding the proper amount of aldehyde/ ketone-dnp stock standard-3 and diluting with an acetonitrile solution. Sample Preparation The preparation for vehicle passenger cabin air samples (including pretreatment, sampling, and elution) was performed by a third-party inspection institution located in Shanghai, hina and based on the standard methods enacted by the hinese government. 0,9 Pretreatment The new vehicles selected for testing came off the production line within 8 ± 5 days and contained no additional interior decoration. For pretreatment the vehicles were moved to an environmental chamber, the doors and windows of the vehicles were opened, and the sampling system was configured. The height of the sampling point was similar to that of a driver s mouth. After at least 8 h, the temperature (5 ), pressure ( atm), humidity (50%), and air velocity (0. m/s) in the environmental chamber were recorded. The car doors were then closed and the same measurements were again recorded after 6 h.
3 Sampling A schematic diagram of the sampling system is shown in Figure. ollect the cabin air in a sampling tube impregnated with leanert DNP-Silica (Bonna-Agela Techologies, hina) for 30 min using an Airhek 000 Air Sampling Pump (SK Inc., USA) at a flow rate of 400 ml/min. The derivatization reactions for carbonyl compounds using DNP are shown in Figure 3. The permissible flow rate error between beginning and end is <5%, calibrated using a D-Lite Flowmeter (SK Inc., USA). After collection, seal the sampling tube with aluminum foil, store at 4 or lower, and deliver to the lab for analysis. Vehicle Sampling Point Device for Deozonization Figure. Sampling system for cabin air tests. Sampling Tube Impregnated with DNP onstant Flow Sampling Pump Elution Elute the sampling tube with 5 ml acetonitrile. After elution, bring the eluate to a volume of 5 ml with acetonitrile and filter through a nylon syringe filter. hromatographic onditions System olumn: Thermo Scientific Acclaim 0, 8, 3 µm Analytical, mm (P/N 05933) Mobile Phase: A. DI water; B. 3 N/TF (60:40, v/v) Gradient: B. 0 8 min, 55%; 0 min, 70%; min, 55% Flow Rate:.0 ml/min Inj. Volume: 0 µl Temperature: 30 Detection: UV, 360 nm System olumn: Thermo Scientific Syncronis 8,.7 µm,. 00 mm (P/N ) A. DI water; B. 3 N/TF (60:40, v/v) Mobile Phase: Gradient: B. 0.5 min, 55%; 9 min, 70%; 9. 0 min, 55% Flow Rate: 0.35 ml/min Inj. Volume:.0 µl Temperature: 35 Detection: UV, 360 nm 3 N N R R = + N - N N + = N - N N + 0 R R arbonyl ompound DNP DNP-Derivatized arbonyl ompound Figure 3. Derivatization reaction of carbonyl compounds using DNP.
4 4 Results and Discussion Separation of DNP-Derivatized arbonyl ompounds Using Different olumns The PL methods for carbonyl compounds in ARB Method 0049 and J/T use 8 stationary phases. In ARB Method 004, two systems are required because the DNP derivatives of methyl ethyl ketone and butyraldehyde do not completely resolve and sometimes coelute on the primary system when using octadecylsilyl-silica gel columns. Resolution requires a complementary step on the secondary system using other equivalent columns to focus solely on the separation of the two peaks. In the work shown here, two reversed-phase columns the Acclaim 0 8 and the Syncronis 8 columns were evaluated for the separation of the DNP-derivatized carbonyl compounds. As shown in Figure 4, the separation problem of the DNP derivatives of acetone (Peak 3) and acrolein (Peak 4) found in J/T was resolved using either one of these two columns, as was the problem of coelution of DNP-derivatized methyl ethyl ketone (Peak 7) and butyraldehyde (Peak 8) found in ARB Method 004. Moreover, method robustness was improved due to the use of easy-to-prepare mobile phases and easily executed mobile phase gradients. Table lists the calculated peak resolutions (Rs) between the DNP derivatives discussed above, showing that satisfactory results can be achieved using either of the two evaluated columns. Likewise, using J/T on conventional 8 columns with acetonitrile/water mobile phases, it is difficult to differentiate DNP derivatives of acetone and acrolein because of their similar size and hydrophobicity. It is possible to optimize chromatographic conditions with a flow rate of. ml/min, a column temperature of 3, and a mobile phase composition of acetonitrile/water/ TF = 34/5.8/3.. 0 owever, the mobile phase must be controlled to the tenth of a percent to achieve baseline resolution of the DNP derivatives of acetone and acrolein, thus demonstrating that the method is not rugged with respect to mobile phase composition. Table. Peak resolution of critical compound pairs on the evaluated columns. Analyte Pair Acclaim 0 8 olumn Rs Syncronis 8 olumn Acetone/Acrolein Methyl Ethyl Ketone/ Butyraldehyde A A olumn: Acclaim 0 8, 3 µm ( mm) Mobile Phase: A. DI water B. 3 N/TF (60:40, v/v) Gradient: B. 0 8 min, 55%; 0 min, 70%; min, 55% Flow Rate:.0 ml/min Inj. Volume: 0 µl Temperature: 30 B olumn: Syncronis 8,.7 µm (. 00 mm) Mobile Phase: A. DI water B. 3 N/TF (60:40, v/v) Gradient: B. 0.5 min, 55%; 9 min, 70%; 9. 0 min, 55%. Flow Rate: 0.35 ml/min Inj. Volume:.0 µl Temperature: B Peaks:. Formaldehyde. Acetaldehyde 3. Acetone 4. Acrolein 5. Propionaldehyde 6. rotonaldehyde 7. Methyl Ethyl Ketone 8. Butyraldehyde 9. Methacrolein 0. Benzaldehyde. Valeraldehyde. m-tolualdehyde 3. exanaldehyde Figure 4. DNP-derivatized carbonyl compound standards.
5 Reproducibility, Linearity, and Detection Limits Method precision was estimated by making five consecutive injections of a calibration standard with a concentration of 0.5 µg/ml for each compound. The retention time and peak area reproducibilities using each of the two columns show good precision and are summarized in Table. alibration linearity of the DNP derivatives of carbonyl compounds was investigated by making three consecutive injections of a mixed standard prepared at six different concentrations (i.e., 8 total injections). The external standard method was used to establish the calibration curve and quantify these DNP derivatives of carbonyl compounds in the cabin air samples. Excellent linearity was observed from 0.03 to.5 µg/ml when plotting the concentration versus the peak area, and the coefficients of determination were for all (Table 3). 5 Table. Reproducibility for peak retention time and area on the evaluated columns (n = 5). Analyte Acclaim 0 8 olumn Syncronis 8 olumn (DNP Derivative) Retention Time RSD Peak Area RSD Retention Time RSD Peak Area RSD Formaldehyde Acetaldehyde Acetone Acrolein Propionaldehyde rotonaldehyde Methyl Ethyl Ketone Butyraldehyde Methacrolein Benzaldehyde Valeraldehyde m-tolualdehyde exanaldehyde Table 3. Method linearity data. Analyte (DNP Derivative) Acclaim 0 8 olumn Syncronis 8 olumn Regression Equation r Regression Equation r Formaldehyde A = 6.083c A =.455c Acetaldehyde A = c A = c Acetone A = 3.475c A = c Acrolein A = 4.679c A = c Propionaldehyde A = 3.50c A = 0.78c rotonaldehyde A =.9575c A = 0.65c Methyl Ethyl Ketone A =.760c A = 0.575c Butyraldehyde A = c A = 0.650c Methacrolein A =.889c A = 0.6c Benzaldehyde A =.9963c A = c Valeraldehyde A =.458c A = c m-tolualdehyde A =.688c A = c exanaldehyde A =.06c A = 0.435c
6 6 Figure 5 shows a carbonyl compound calibration standard with a concentration of 0.03 µg/ml for each DNP derivative separated on the Syncronis 8 column. The calculated signal-to-noise (S/N) ratios are summarized in Table 4. The method detection limit (MDL) of each DNP derivative was measured using UV detection and calculated using S/N = 3; all MDLs were 5 µg/l, showing good method sensitivity olumn: Syncronis 8,.7 µm (. 00 mm) Mobile Phase: A. DI water B. 3 N/TF (60:40, v/v) Gradient: B. 0.5 min, 55%; 9 min, 70%; 9. 0 min, 55% Flow Rate: 0.35 ml/min Inj. Volume:.0 µl Temperature: 35 Peaks:. Formaldehyde. Acetaldehyde 3. Acetone 4. Acrolein 5. Propionaldehyde 6. rotonaldehyde 7. Methyl Ethyl Ketone 8. Butyraldehyde 9. Methacrolein 0. Benzaldehyde. Valeraldehyde. m-tolualdehyde 3. exanaldehyde Sample Analysis Figures 6 and 7 show two DNP-derivatized cabin air samples, each analyzed on one of the two evaluated columns. Formaldehyde and acetone were found in both samples, whereas methyl ethyl ketone was found only in abin Air Sample, demonstrating the presence of aldehyde and ketone compounds in cabin air. The detected concentration of formaldehyde in abin Air Sample was 38 µg/m 3, higher than the level permitted in the Standardization Administration of hina (SA) GB/T (00 µg/m 3 ), 9 thereby disqualifying the vehicle that produced abin Air Sample. Recoveries for the three detected DNP derivatives of carbonyl compound standards in the sample were nearly 00% using the Acclaim 0 8 column, demonstrating good accuracy of the PL method. The analysis results summarized in Table 5 validate that successful sample analysis is possible using either of the two evaluated columns. 50 olumn: Acclaim 0 8, 3 µm ( mm) Mobile Phase: A. DI water B. 3 N/TF (60:40, v/v) Gradient: B. 0 8 min, 55%; 0 min, 70%; min, 55% Flow Rate:.0 ml/min Inj. Volume: 0 µl Temperature: 30 Samples: A. DNP-derivatized abin Air Sample B. A spiked with DNP-derivatized carbonyl compound mixed standard (0.5 µg/ml each) Peaks:. Formaldehyde. Acetone 3. Methyl Ethyl Ketone Figure 5. DNP-derivatized carbonyl compound standards (0.03 µg/ml each). Table 4. S/N of DNP derivatives (concentrations of 0.03 µg/ml each) obtained using a Syncronis 8 column. Peak Name (DNP Derivative) S/N Formaldehyde 4.3 Acetaldehyde.0 Acetone 7.4 Acrolein 7.6 Propionaldehyde 3.5 rotonaldehyde.4 Methyl Ethyl Ketone 8. Methacrolein.9 Butyraldehyde 9.6 Benzaldehyde 8. Valeraldehyde 7. m-tolualdehyde 7.3 exaldehyde B A Figure 6. DNP-derivatized abin Air Sample (A) and the same sample spiked with a DNP-derivatized carbonyl compound mixed standard (B). 3 3
7 Table 5. Sample analysis results. 7 Analyte abin Air Sample Using Acclaim 0 8 olumn Detected (µg/m 3 ) Added (µg/ml) Found (µg/ml) Recovery (%) abin Air Sample Using Syncronis 8 olumn Detected (µg/m 3 ) Permitted in GB/T (µg/m 3 ) Formaldehyde Acetone Methyl Ethyl Ketone olumn: Syncronis 8,.7 µm (. 00 mm) Mobile Phase: A. DI water B. 3 N/TF (60:40, v/v) Gradient: B. 0.5 min, 55%; 9 min, 70%; 9. 0 min, 55% Flow Rate: 0.35 ml/min Inj. Volume:.0 µl Temperature: 35 Peaks:. Formaldehyde. Acetone Figure 7. DNP-derivatized abin Air Sample. onclusion The work shown here describes efficient PL methods combined with UV detection for the determination of DNP-derivatized carbonyl compounds in cabin air samples. All 3 carbonyl compounds listed in ARB Method 004, IS , U.S. EPA ompendium Method T-A, and the hinese J/T are well separated on the Acclaim 0 8 and Syncronis 8 columns, and the separation takes <0 min using the Syncronis 8 column. References. ealth Effects Notebook for azardous Air Pollutants; Technology Transfer Network Air Toxics Web Site; U.S. Environmental Protection Agency: incinnati,, html (accessed April 8, 03).. Przybylski, R.; ougen, F. W. Simple Method for Estimation of Volatile arbonyl ompounds in Edible ils and Fried Potato hips. J. Am. il hem. Soc. 989, 66, Kaminski, E.; Przybylski, R.; Wasowicz, E. Spectrophotometric Determination of Volatile arbonyl ompounds as a Rapid Method for Detecting Grain Spoilage During Storage. J. ereal Sci. 985, 3 (), Method 556: Determination of arbonyl ompounds in Drinking Water by Pentafluorobenzylhydroxylamine Derivatization and apillary Gas hromatography with Electron apture Detection; U.S. Environmental Protection Agency, National Exposure Research Laboratory, ffice of Research and Development: incinnati,, Method 554: Determination of arbonyl ompounds in Drinking Water by Dinitrophenylhydrazine Derivatization and igh Performance Liquid hromatography; U.S. Environmental Protection Agency, National Exposure Research Laboratory, ffice of Research and Development: incinnati,, Method 835A: Determination of arbonyl ompounds by igh Performance Liquid hromatography (PL); U.S. Environmental Protection Agency, National Exposure Research Laboratory, ffice of Research and Development: incinnati,, ompendium Method T-A: Determination of Formaldehyde in Ambient Air Using Adsorbent artridge Followed by igh Performance Liquid hromatography (PL) [Active Sampling Methodology]; U.S. Environmental Protection Agency, enter for Environmental Research Information, ffice of Research and Development: incinnati,, Method T-5: Method for the Determination of Aldehydes and Ketones in Ambient Air Using igh Performance Liquid hromatography (PL); U.S. Environmental Protection Agency, National Exposure Research Laboratory, ffice of Research and Development: incinnati,, 984.
8 9. alifornia Non-Methane rganic Gas Test Procedures; Method No. 004: Determination of Aldehyde and Ketone ompounds in Automotive Source Samples by igh Performance Liquid hromatography; alifornia Environmental Protection Agency, Air Resources Board: El Monte, A, 0; pp F- F-9. [nline] lev%0iii_clean%0complete_-.pdf (accessed April 7, 03). 0. J/T : Determination of Volatile rganic ompounds and arbonyl ompounds in abin of Vehicles; Ministry of Environmental Protection of the People s Republic of hina, Environmental Protection Industry Standards of the People s Republic of hina: Beijing, IS :0: Indoor Air Part 3: Determination of Formaldehyde and ther arbonyl ompounds in Indoor Air and Test hamber Air Active Sampling Method; International rganization for Standardization (IS): Geneva, Switzerland, 0.. oshika, Y.; Takata, Y. Gas hromatographic Separation of arbonyl ompounds as Their,4-Dinitrophenylhydrazones Using Glass apillary olumns. J. hromatogr., A 976, 0 () Dong, J. Z.; Moldoveanu, S.. Gas hromatography Mass Spectrometry of arbonyl ompounds in igarette Mainstream Smoke after Derivatization with,4-dinitrophenylhydrazine. J. hromatogr., A 004, 07, Dionex (now part of Thermo Scientific) Application Note 97: Determination of arbonyl ompounds by Reversed-Phase igh-performance Liquid hromatography. Sunnyvale, A, 00. [nline] LPN0578.pdf (accessed April 9, 03). 5. de arvalho, A. B.; Kato, M.; Rezende, M. M.; de P. Pereira, P. A.; de Andrade, J. B. Determination of arbonyl ompounds in the Atmosphere of harcoal Plants by PL and UV Detection. J. Sep. Sci. 008, 3, Possanzini, M.; Palo, V. D. Determination of Formaldehyde and Acetaldehyde in Air by PL with Fluorescence Detection. hromatographia 997, 46 (5-6), Zurek, G.; Karst, U.,4-Dinitro-3,5,6- Trideuterophenylhydrazones for the Quantitation of Aldehydes and Ketones in Air Samples by Liquid hromatography Mass Spectrometry. J. hromatogr., A 000, 869, hi, Y.; Feng, Y.; Wen, S.; Lü,.; Yu, Z.; Zhang, W.; Sheng, G.; Fu, J. Determination of arbonyl ompounds in the Atmosphere by DNP Derivatization and L-ESI-MS/MS Detection. Talanta 007, 7, GB/T : Guideline for Air Quality Assessment of Passenger ar; Standardization Administration of hina (SA), General Administration of Quality Supervision, Inspection and Quarantine of the People s Republic of hina: Beijing, Kim, S. D.; Kim,..; Park, J. S.; Lee, J. J. A Study on the Peak Separation of Acetone and Acrolein Based on igh-performance Liquid hromatography (PL) Method. Bull. Korean hem. Soc. 009, 30, Application Note Thermo Fisher Scientific Inc. All rights reserved. erilliant is a registered trademark of erilliant orporation. All other trademarks are the property of Thermo Fisher Scientific Inc. and its subsidiaries. This information is presented as an example of the capabilities of Thermo Fisher Scientific Inc. products. It is not intended to encourage use of these products in any manners that might infringe the intellectual property rights of others. Specifications, terms and pricing are subject to change. Not all products are available in all countries. Please consult your local sales representative for details. Australia Austria Belgium Brazil hina Denmark France Germany India Italy Japan Korea Netherlands Singapore Sweden Switzerland Taiwan UK/Ireland USA and anada AN705_E 07/6S
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