ACROLEIN in .NET

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Colorless or yellow mobile liquid with pungent and irritating odor 160 ppb (370 g/m3) (Reference 33) C3H4O
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H H C=C C=O H
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56.06 g 0.843 at 20 C, 0.862 at 0 C 52.5 C 88 C 29.3 36.5 kPa at 20 C 206 270 g/L in water at 20 C, soluble in ethanol and diethyl ether 0.446 19.6 Pa m3/mol at 20 C 7.8 180 dimensionless at 25 C 1.1 1.02 0.219 2.43 1 ppm = 2.3 mg/m3 at 25 C
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ed as 2,4-dinitrophenhylhydrazones in bone grease using thin-layer chromatography (TLC) and ultraviolet (UV) spectra. Among the monocarbonyl compounds identi ed, 4.2 g/g of acrolein was found in bone grease (38). Later, more sensitive tests with higher-resolution gas chromatography and HPLC were beginning to be used to isolate and identify various 2,4dinitrophenylhydrazones. Acrolein contents (mg/kg) in yeast-raised and cake doughnuts fried at 182 C were determined using HPLC. Identity of the acrolein derived hydrazone was con rmed by GC/MS (23). Acrolein formed in fumes from heated cooking oils was trapped in the glass ber lter incorporated with the Sp-Pak DNPH-silica cartridge containing 1,4-DNPH. After the sample was extracted with acetonitrile, acrolein was analyzed as a hydrazone derivative using HPLC with a ultraviolet/visual (UV/VIS) detector (27). When the analytical results of low-molecular-weight aldehydes including acrolein were examined using the 2,4-DNPH/HPLC method from 14 different laboratories, this technique was usually comparable among the different laboratories within 2 times the coef cient of variation ( 6 15%) (39). Even though many derivatives, in addition to hydrazones, have been developed for analysis of low-molecular-weight carbonyl compounds, 2,4-DNPH remains the most widely used derivatizing agent for carbonyl compounds. Above all, the recent rapid advancement of liquid chromatography/tandem mass spectrometry (LCMS/MS) may promote the use of this method. In fact, the analysis of the aminobutyric acid (GABA) analogue succinic semialdehyde in urine and cerebrospinal uid was recently performed using 2,4-DNPH derivatization and liquid chromatography/mass spectrometry (LC/MS) (40).
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ANALYSIS OF ACROLEIN IN FOODS AND BEVERAGES (a)
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O HC R1 C - R1 HC - R2 , -Unsaturated aldehyde R1: H R2: H Acrolein
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m-Hydroxy aniline
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R1: H 7-Hydroxyquinoline R2: H
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HN - NH2 NO2 R1 R1 HN - N = C R NO2 2
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NO2 2,4-Dinitrophenylhydrazine
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O=C R2 Carbonylcompounds R1: H R2: CH=CH2 Acrolein NO2 2,4-Dinitrophenylhydrazone
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H N + CH2 = CHCHO O Morpholine Acrolein
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CH2 - CH2CHO N
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O 3-Morpholinopropanal
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H O + R 2-Alkenal Acrolein: R = H H2N HN CH3 N-methylhydrazine N R N CH3 Pyrazoline derivative N-Methylpyrazoline: R = H
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O- Na+ R - CHO + NaSO3 Sodium bisulfite R C OS OH H O
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Figure 2.2.1 Mechanisms of reactions used to prepare acrolein derivatives. (a) Reaction of , -unsaturated aldehydes with m-hydroxy aniline to form 7-hydroxyquinolines. (b) Reaction of carbonyl compounds with 2,4-DNPH to form 2,4-dinitrophenylhydrazones. (c) Reaction of acrolein with morpholine to form 3-morpholinopropanal. (d) Reaction of 2-alkenals with N-methylhydrazine to form pyrazoline derivatives. (e) Addition of sodium bisul te to aldehydes to form 1-hydroxy-1-sulfonic acid derivatives. (f) Reaction of aldehydes with PFBHA to form oxime derivatives. (g) Reaction of 2-alkenal with PFPH to form PFPH adducts.
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F F F F F CH2O NH2 +R CHO F F R: CH2 = CH F Oxime derivatives CH2O F F
ACROLEIN
R N C H
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PFBHA
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F F F F PFPH F O NHNH2 + R 2-Alkenal Acrolein: R = H F F R: H F PFPH-Adduct Acrolein Adduct N N H F F
Continued
As mentioned earlier, many methods for trace acrolein analysis have been developed and used successfully for analysis in foods. A unique derivative 3morpholinopropanal (C), produced from acrolein and morpholine, was applied to analyze acrolein in the headspace of heated cooking oils and beef fat (25). After the pyrazoline derivative of acrolein with N-methylhydrazine (NMH) was prepared (D) for trace analysis of acrolein in 1990 (41), many analyses of acrolein in photo-irradiated or heated lipid samples were conducted using this method. This derivatizing agent, NMH was originally used to measure malonaldehyde as a pyrazole derivative (42, 43). It was found that NMH reacted with saturated monocarbonyl compounds, 2-alkenals (e.g., acrolein), and dicarbonyl compounds (e.g., malonaldehyde) to form hydrazones, pyrazolines, and pyrazoles, respectively. Consequently, acrolein was analyzed in various samples: fatty acids and cod liver oil oxidized with Fenton s reagent (44, 45); UV irradiated fatty acids (41), cod liver oil (46), and triolein (47); heated lard, corn oil, sun ower oil, and cotton seed oil (48); kitchen air (49); and cigarette smoke (50, 51). The detection limit of acrolein as N-methylpyrazoline was 5.9 pg (49). Acrolein in raw spirits samples was analyzed by the isotachophoretic method after it was derivatized to 1-hydroxy-1-sulfonic acid derivative with sodium bisul te (E) (32). A limit of detection at 0.03 g/mL 100% ethanol was achieved by this method. Acrolein in spirits and alcoholic beverages was also determined as O-(2,3,4,5,6-penta uorobenzyl)hydroxylamine (PFBHA) derivative (F). The resulting oxime was extracted using polydimethylsiloxane (PDMS) ber by direct immersion into solution or from headspace. The analyte