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ARABJC 320 No. of Pages 9
17 February 2011
Arabian Journal of Chemistry (2011) xxx, xxx–xxx
ORIGINAL ARTICLE
KEYWORDS Abstract A simple and sensitive spectrophotometric method for the determination of formalde-
Formaldehyde; hyde FA in different samples using tryptamine TA in a sulfuric acid medium was developed. A trace
Tryptamine; amount of sodium nitrite was added to enhance the production of a red violet colored product
Spectrophotometery; exhibiting an absorbance maximum at 558 nm. Beer’s Law is obeyed for 0.80–23.00 lg mL 1 FA
Environmental samples (r = 0.999), the recoveries are within the range of 96.25–100.66%, with percent relative standard
deviations ranging from 1.02% to 2.73%. No interference was detected from commonly existing
contaminates in the liquid samples e.g. phenol, aminoacids, sugars and related compounds. The
method was applied successfully for the determination of formaldehyde in various environmental
samples, such as rain water, wood products, and total cigarette smoke.
11 ª 2011 King Saud University. Production and hosting by Elsevier B.V. All rights reserved.
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
2 N.G. Yasri et al.
37 Sensitive methods for formaldehyde determination include chased from Merck and 5% (w/v) chromotropic acid from Mal- 93
38 GC (Bianchi et al., 2007; Del Barrio et al., 2006; Reche linckrodt Chemical was freshly prepared in bidistilled water. 94
39 et al., 2001; Velikonj et al., 1995; Davydova et al., 1986), vol-
40 tammetry (Zhao et al., 2006), fluorometry (Zhang and Tian, 3. Method 95
41 2004; Li et al., 2007), LC and HPLC (Possanzini and Di Palo,
42 2003; Witthauer et al., 1999; Isakau et al., 2009; Fu Liu et al., 3.1. Spectrophotometric calibration curve 96
43 2005; Huber and Fresenius, 1981; Chen et al., 2008). However,
44 spectrophotometric based methods (Teixeira et al., 2004; Feng Proper volumes of the FA working standard solution were 97
45 et al., 2004; Gigante et al., 2004; Tian et al., 2004; Cui et al., transferred to the stoppered test tubes to cover the concentra- 98
46 2007; Jagadeesan and Gupta, 1979; Li et al., 2008; Gibson tion range of 0.80–23.00 lg mL 1. The FA solution was di- 99
47 et al., 2008; Mohamed et al., 2008; Guo et al., 2006; Pinheiro luted with water to 4.0 mL, the test tubes were replaced in 100
48 et al., 2004) are among the relatively low-cost, simple and sen- the water bath at a constant temperature of 25 C, followed 101
49 sitive methods and are very popular. These methods are based by the addition of 4.0 mL concentrated H2SO4, the tempera- 102
50 on the reaction of formaldehyde with reagents, such as Schiff’s ture was allowed to stabilize then 1.0 mL of the working TA 103
51 reagent (Gibson et al., 2008), p-phenylenediamine (Mohamed solution was added followed by 1.0 mL sodium nitrite solu- 104
52 et al., 2008), chromotropic acid (Gigante et al., 2004), brilliant tion. All test tubes were then capped and left in the water bath 105
53 cresyl blue (Guo et al., 2006) and fluoral P (Pinheiro et al., for 35 min to ensure complete color development. A calibra- 106
54 2004). tion graph was prepared by recording the absorbance of the 107
55 The present work reports a simple, sensitive and accurate resulting solutions at 558 nm against a similarly prepared re- 108
56 spectrophotometric method for the determination of formalde- agent blank. All measured solutions were prepared in 109
57 hyde in aqueous samples. The method is based on the forma- triplicates. 110
58 tion of a colored telomere from the reaction of formaldehyde
59 with indol-3-ethylamine (knows as tryptamine; TA), in a sulfu- 3.2. Formaldehyde determination in rain water 111
60 ric acid medium. The method was optimized for the determina-
61 tion of unknown levels of formaldehyde in samples of Some portions of countryside rain water (Aleppo City, Syria) 112
62 rainwater, wooden products, and total cigarette smoke. were collected at two different time periods; each portion 113
was about 100 mL volume. The first collection was in the first 114
63 2. Material and methods autumn rainfall in the second week of September 2009 and the 115
second sample was collected from the same place after about 116
64 2.1. Apparatus one month. The collected rain water samples were immediately 117
filtered through a 0.45 lm membrane filter from which a vol- 118
65 A Jasco V-630 spectrophotometer with 1.0 cm quartz cell was ume of 100 mL was heated, with continuous stirring, in a water 119
66 used for spectrophotometric measurements. An HPLC system bath at 80 C for 10 min (Mohamed et al., 2008), in these con- 120
67 (Merck-Hitachi) equipped with a diode array detector L-2455, ditions, the volatile acetaldehyde was expelled, and at the same 121
68 quaternary pump L-2200 and column temperature regulator time they have a little effect on FA (recoveries of FA P97%), 122
69 L-2350 was used. The analytical column used was a RP8 HI- which begin to drift with water vapor at P90 C (Mohamed 123
70 BAR (250 · 4.6 mm ID 10 lm) from Merck. The chromato- et al., 2008). The solution was left for a few minutes to cool 124
71 graphic system was eluted by (45:55 v/v) acetonitrile:water after which bidistilled water was added to the volume to re- 125
72 solution as a mobile phase, with 20 lL injection volume at a place any evaporation. 126
73 flow rate of 1.0 mL min 1, and a detector set at 345 nm wave- In order to determine the low levels of FA a preconcentra- 127
74 length. A digital Orion Research Model 601 analyzer provided tion procedure was performed by subjecting the resulting solu- 128
75 with an Ingold U455 electrode was used for pH measurements. tion to a crystallization process with bisulfite. This was 129
proceeded as follows: 5 g sodium bisulfite was added to 130
76 2.2. Reagents and chemicals 100 mL of the rain water, then the mixture was kept in an 131
ice bath for one hour (ensuring a complete FA and bisulfite 132
77 Reagent-grade chemicals used were of the highest purity avail- reaction), after which an accurate volume of 50 mL ethanol 133
78 able from their sources. A stock FA solution of 1000 lg mL 1 (95%) was added without stirring (the aqueous: ethanol ratio 134
79 was prepared by diluting a volume of 2.5 mL (37%) formalde- was 2:1 (v/v)). The mixture was then refrigerated (at 4 C) 135
80 hyde solution FA (SCP, super chemical produces) to 1000 mL for 30 min which lead to the formation of crystals from bisul- 136
81 with bidistilled water and standardized using the sulfite method fite addition compound. The crystals were then filtered using 137
82 (Annual Book of American Society for Testing and (ASTM) 0.45 lm membrane filter, and the filtrate was discarded. The 138
83 Standards, 1979). FA working standard solutions of 100 and crystals were kept at room temperature for solvent evapora- 139
84 10 lg mL 1 were prepared daily from the stock standard solu- tion, followed by the dissolution of the dry crystals with suit- 140
85 tion by appropriate dilution. Tryptamine reagent TA able volume of 0.05 mol L 1 sulfuric acid, making the final 141
86 5 · 10 2 mol L 1 was prepared by dissolving 0.817 g (98% pur- FA concentration within the standard linear range of the sug- 142
87 ity, Merck chemicals) tryptamine in 1% H2SO4 and then com- gested method. A 3 mL volume of the resulting solution was 143
88 pleting the volume to 100 mL using the same solvent. Sodium used in the proposed method for FA determination. 144
89 nitrite solution 2 · 10 3 mol L 1 was prepared by dissolving A separate FA preconcentration study with bisulfite crys- 145
90 0.139 g of 99% sodium nitrite (BDH England), in bidistilled tals was performed to ensure higher recovery for trace FA le- 146
91 water and diluting to 1000 mL in a volumetric flask. Sulfuric vel. The study included ethanol to water ratio, bisulfite 147
92 acid (98%), 2,4-dinitrophenylhydrazine (DNPH) were pur- quantity, and FA concentration. 148
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
Spectrophotometric determination of formaldehyde based on the telomerization reaction of tryptamine 3
0.8
0.7
0.6
0.5
A 0.4
0.3
0.2
0.1
0.0
0 0.5 1 1.5 2 2.5 3 3.5 4 4.5 5 5.5
Volume of H 2SO4, mL
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
4 N.G. Yasri et al.
202 4.2. Effect of sodium nitrite concentration and other oxidants reaction time and a maximum was reached after 6 h. Alterna- 224
203 material tively, the presence of 2 · 10 4 mol L 1 NaNO2 enhanced the 225
reaction rate with a nearly stable colored product formation 226
204 It has been noticed during preliminary testing experiments that after 35 min that remained for 6 h. 227
205 the addition of trace amount of oxidants, e.g. H2O2 and Fe3+ It has been known that NaNO2 in acidic solution gives ni- 228
206 [as Fe2(SO4)3], increases the reaction speed with no effect on trous acid which decomposed with the evolution of nitrogen 229
207 the total absorbance value. Adding a trace amount of sodium oxides, but at these reaction conditions of temperature and or- 230
208 nitrite to the sulfuric acid media containing FA and TA, how- der of material addition (FA, H2SO4, TA, and then NaNO2), 231
209 ever, caused an increase in both, the absorbance (Fig. 2) and in the absorption and the reaction speed were surprisingly in- 232
210 the reaction speed. creased, even at a temperature reaching 25 C. 233
211 The effect of NaNO2 concentration was studied within the It is suggested that the presence of NaNO2 could enhance 234
212 range of 0.5 · 10 5–1.4 · 10 3 mol L 1. The results (Fig. 3) the formation of a hydrated semi oxidized species of formalde- 235
213 show that the absorbance increased rapidly with increasing hyde that have more efficiency to condense with indole and its 236
214 NaNO2 concentration with a maximum at 2 · 10 4 mol L 1. derivatives. 237
215 Further increases in the NaNO2 concentration to a value more
216 than 9 · 10 4 mol L 1, may lead to a decrease in the absorp- 4.3. Constitution of the colored product 238
217 tion value. Thereafter, a concentration of 2 · 10 4 mol L 1
218 of NaNO2 was adopted for further experiments. The nature of the binary colored product (FA-TA) was deter- 239
219 Taking into consideration the color development period, mined by performing two studies, the first using continuous 240
220 the absorbance of the color was monitored for 8 h both in variation method (Likussar and Boltz, 1971). In this method, 241
221 the absence and in the presence of NaNO2. In the absence of a series of solutions were prepared, with that the concentration 242
222 sodium nitrite, the result (Fig. 4) shows that the colored prod- of FA plus TA were held constant at 1.0 · 10 3 mol L 1. A 243
223 uct formation increased gradually during the first 3 h of the graph was prepared by plotting absorbance against the ratio 244
[FA]/[FA] + [TA]. The result of applying this method, 245
(Fig. 5), indicated that the (TA:FA) ratio is 2:1. 246
1.1
The second study used a molar ratio method (Meyer and 247
1.0 Ayres, 1957), this was performed by increasing the TA concen- 248
0.9 tration within the range of (1.3 · 10 3–2.1 · 10 4) mol L 1, for 249
the formation of the colored product with constant FA con- 250
0.8
A centration of 2.7 · 10 4 mol L 1. 251
0.7
0.6
0.5 0.4
0.4
0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 0.3
Concentration of NaNO 2 mol.L-1, ×10-4
A 0.2
Figure 3 The effect of sodium nitrite concentration on the
absorbance values at 558 nm. Experimental conditions: HCHO
2.7 · 10 4 mol L 1; TA 5 · 10 3 mol L 1; 4 mL H2SO4 (98%); at 0.1
25 C and wait for 30 min; 10 mL final testing mixture.
0.0
0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1
[FA]/[FA] + [TA]
1.2
Figure 5 Continuous variation method for FA-TA colored
1 production at 558 nm. Experimental conditions: 2 · 10 4 mol L 1
0.8
NaNO2; 4 mL H2SO4 (98%); at 25 C and wait for 30 min; 10 mL
final testing mixture.
A 0.6
0.4
0.2
NH 2 NH2 NH 2
0
0 1 2 3 4 5 6 7 8 9 CH 2 CH2 CH 2
CH 2 CH 2 CH 2
Time, hour O +
+ C H CH2
2
Figure 4 The absorbance variation at 558 nm during 8 h time in N H H - H2O N N
the absence and in 2.7 · 10 4 mol L 1 HCHO: the present of H H H
2 · 10 4 mol L 1 NaNO2. Experimental conditions:
5 · 10 3 mol L 1 TA; 4 mL H2SO4 (98%); at 25 C; 10 mL final Scheme 2 Possible telomerisation reaction of formaldehyde with
testing mixture. tryptamine.
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
Spectrophotometric determination of formaldehyde based on the telomerization reaction of tryptamine 5
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
6 N.G. Yasri et al.
Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
Spectrophotometric determination of formaldehyde based on the telomerization reaction of tryptamine 7
356 0.5:2, 0.75:2, 1:2, 1.25:2, 1.5:2, and 2:2 gives recoveries of FA in the two rain water samples analyzed indicate high levels 387
357 50.2%, 94.5%, 95.3%, 94.7%, 30.7%, and 0.0%, respectively, of FA pollutant, which demand more attention and control of 388
358 with that, the excess of ethanol to a ratio more than 1:2 caused the pollutant’s emission in the region. 389
359 re-dissolution of the crystal.
360 Similar treatment of a solution containing trace formalde- 6. Conclusion 390
361 hyde levels of 0.08, 0.05, and 0.03 lg mL 1 gives (recov-
362 ery ± RSD)% of (95.25 ± 2.9)%, (94.80 ± 3.1)%, and A spectrophotometric method has been developed for the 391
363 (94.07 ± 3.7%) respectively. determination of low level formaldehyde. The developed meth- 392
od depends on the formation of a red violet colored product 393
364 5. Application from the telomerisation of FA with TA in the presence of con- 394
centrated sulfuric acid and trace NaNO2 amounts. The method 395
365 The analytical results of FA with the suggested method in rain is shown to be selective, sensitive, simple and easy to perform. 396
366 water were compared with the result obtained by HPLC mea- The colored product that has been formed is stable at a tem- 397
367 surement (Tsai et al., 2003), and are in good agreement. The perature less than or equal to 25 C, and does not interfere 398
368 HPLC measurement depended on the derivatization of FA with substances normally present as pollutants. The method 399
369 with 0.1% of 2,4-dinitrophenylhydrazine reagent (DNPH). validation proved the accuracy and precision for the routine 400
370 While the analytical results for the other samples of wood application of low level formaldehyde determination. 401
371 products, and TSS samples were compared with the standard
372 chromotropic acid method adopted by NIOSH (Institute for 7. Uncited reference 402
373 Occupational Safety and Health, 1994). The obtained analyti-
374 cal results, Table 5, gave quantitative recoveries in the range of Dean (1998). Q7 403
375 96.0–100.0%. The test of significance shows that Student’s t-
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ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005
ARABJC 320 No. of Pages 9
17 February 2011
8 N.G. Yasri et al.
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Please cite this article in press as: Yasri, N.G. et al., Spectrophotometric determination of formaldehyde based on the telomer-
ization reaction of tryptamine. Arabian Journal of Chemistry (2011), doi:10.1016/j.arabjc.2011.02.005