Chemical structures of azo-dye

Fig. 3.45. Chemical structure of azo dye Reactive yellow 84. Reprinted with permission from M. Koch et al. [120],...

The efficacy of the various methods used for the extraction of azo dyes from toy products has been determined and the results compared. The investigations were motivated by the possible toxic side-effect of the dyes. The chemical structures of azo dyes included in the study are shown in Fig. 3.59. 

Figure 11.5 Chemical structure of azo dyes 6 and 7 and mesogens Ml and M2, and relaxation time for the thermal cis-to-trans isomerization of the formers in different media at 298 K.

The color index (Cl) number, developed by the society of dyers and colorists, is used for dye classification. Once the chemical structure of a dye is known, a fivedigit Cl number is assigned to it. The first word is the dye classification and the second word is the hue or shade of the dye. For example, Cl Acid Yellow 36 (Cl 13065) is a yellow dye of the acid type. Additionally, a dye mixture may consist of several dyes for example, Navy 106 is composed of three reactive azo dyes remazol black B (Reactive Black 5), Remazol Red RB (Reactive Red 198), and Remazol Golden Yellow 3. 

Fig. 3.38.The IUPAC names of Sudan azo dyes are as follows Sudan 1 = 1— [(2,4-dimethylphenyl)azo]-2-naphtalenol Sudan II = l-(phenylazo)-2-naphtol Sudan III = l-(4-phenylazophenylazo)-2-naphtol Sudan IV = o-tolyazo-o-tolyazo-beta-naphtol and Disperse Orange 13 = 4-[4-(phenylazo)-l-naphtylazo]-phenol. Azo dyes were separated in an ODS column (250 x 2.1 mm i.d. particle size 5 /xm) at 35°C. The isocratic mobile phase consisted of 0.1 per cent formic acid in methanol-0.1 per cent formic acid in water (97 3, v/v). The flow rate was 200 /xl/min. MS conditions were nebulizing and desolvation gas were nitrogen at the flow rates of 50 and 5551/h, respectively electrospray voltage, 3.0 kV cone voltage 25 V source temperature, 110°C desolvation temperature, 110°C. Azo dyes were extracted from the samples by homogenizing 1 g of sample with 10 ml of acetone, then the suspension was centrifuged and an aliquot of 3 ml of supernatant was mixed with 1 ml of deionized water, filtered and used for analysis. LC-ESI-MS/Ms SRM traces of standards and spiked samples are listed in Fig. 3.39. It was found that the detection and quantitation limits depended on both the chemical structure of the dye and the character of the accompanying matrix. LOD and LOQ values in chilli tomato sauce...

Liquid chromatographic techniques have been frequently employed for the separation and identification of the toxic decomposition products of synthetic dyes. Thus, the amount of aromatic amines formed from azo dyes in toys has been determined. The chemical structures of the dyes included in the investigation are listed in Fig. 3.60. The dyes were... 

Combined analytical techniques, such as ion chromatography, GC-MS and FTIR, were employed for the investigation of the photocatalytic decomposition of triazine-containing azo dyes in the presence of Ti02 suspensions. The chemical structures of the dyes are shown in Fig. 3.66. 

The most important property of azo dyes is their maximum absorption wavelength (Amax) because it determines the color of azo dyes. Theoretically speaking, A.n,ax of azo dyes is dependent on the electronic structure of azo dye molecules. Quantum chemical calculation has been applied to estimate A ax of some azo dyes. For planar dye molecules, PPP method of quantum chemistry can be used for A.max estimation. But PPP method is not suitable for the estimation of the A,n,ax of azo dyes with non-planar molecules. For azo dyes with non-planar molecules, the application of more sophisticated quantum chemical algorithms has been investigated. Although the calculation of the A,n,ax of some other dye by ZINDO/S algorithm has certain degree of success, the application of... 

Santos V, Morao A, Pacheco Ml, Cirfaco L, Lopes A (2008) Electrochemical degradation of azo dyes on BDD effect of chemical structure and operating conditions on the combustion efficiency. J Environ Eng Manage 18(3) 193-204... 

Normal-phase TLC has been employed for the control of the synthesis of some new reactive azo dyes containing the tetramethylpiperidine fragment. The chemical structure of the basic molecule and the substituents of the new derivatives are shown in Fig. 3.16. The new derivatives were characterized by their RF values determined in different mobile phases. Compositions of mobile phases were n-propanol-ammonia (1 1, v/v) for dye 1.2 (Rp = 0.84) n-propanol-ammonia (2 1, v/v) for dyes 1.3 (RF = 0.50) and 1.4 (RF = 0.80) and n-heptane-diethyl ether (1 1, v/v) for dyes 1.5 (RF = 0.80) and 1.6 (RF = 0.76). The results indicated that together with other physicochemical methods such as IR and H NMR, normal-phase TLC is a valuable tool for the purity control and identification of new synthetic dyes [96],... 

Sulphonated azo dyes were separated and quantitated in various food products by ion-pair liquid chromatography with DAD and electrospray MS detection. The chemical structure of sulphonated azo dyes included in the investigation are shown in Fig. 3.36. Dyes were separated in an ODS column (125 X 2.0 mm i.d. particle size 5 pm) using gradient elution. An aqueous solution of 3 mM triethylamine (pH adjusted to 6.2 with acetic acid) and methanol... 

A separation method using RP-HPLC and electrospray-tandem mass spectrometry was developed for the simultaneous determination of Sudan-azo dyes in hot chilli products. The chemical structures of the azo dyes included in the investigation are listed in... 

Fig. 3.38. Chemical structures of the azo dyes investigated and of the internal standard Disperse orange 13. Reprinted with permission from F. Calbiani el al. [115].

The carcinogenic aromatic amines released from azo dyes in leather were investigated by using microwave-assisted extraction (MAE) or supercritical fluid extraction (SFE) followed by RP-HPLC. The chemical structures of dyes and aromatic amines are listed in Fig. 3.69. The flow schemes for SFE and MAE are shown in Figs 3.70. and 3.71. 

RP-HPLC found application in the monitoring of the alkali hydrolysis kinetics of alkali-clearable azo disperse dyes containing a fluorosulphonyl group. The chemical structures of dyes included in the experiments are shown in Fig. 3.85. Samples for RP-HPLC analysis were neutralized to pH 4.0 - 4.5 with diluted HC1 mixed with five volumes of ACN and injected without any other sample preparation step. Separation was carried out in an ODS column at ambient temperature. The isocratic mobile phase consisted of ACN-water (80 20, v/v) and dyes were detected at their absorption maxima. HPLC measurements indicated that dyes are easily hydrolysed under relatively mild alkaline conditions, and the hydrolysis follows a pseudo first-order kinetics [148],... 

Metabolites formed during the decolourization of the azo dye Reactive red 22 by Pseudomonas luteola were separated and identified by HPLC-DAD and HPLC-MS. The chemical structures of Reactive red 22 (3-amino-4-methoxyphcnyl-/fhydroxyl-sulphonc sulphonic acid ester) and its decomposition products are shown in Fig. 3.92. RP-HPLC measurements were carried out in an ODS column using an isocratic elution of 50 per cent methanol, 0.4 per cent Na2HP04 and 49.6 per cent water. The flow rate was 0.5 ml/min, and intermediates were detected at 254 nm. The analytes of interest were collected and submitted to MS. RP-HPLC profiles of metabolites after various incubation periods are shown in Fig. 3.93. It was concluded from the chromatographic data that the decomposition process involves the breakdown of the azo bond resulting in two aromatic amines [154],... 

RP-HPLC has also found application in the study of the microbial decolourization of reactive azo dyes in a sequential anaerobic-aerobic system. The chemical structures of... 

CZE was also employed for the analysis of sulphonated azo dyes in river samples. The chemical structures of dyes are shown in Fig. 3.150. Separations were performed in a fused-silica capillary (total length 57 cm effective length, 50 cm 75 pm i.d.). Activation of the capillary was carried out by washing it with 1.0 M NaOH for 15 min, followed by water (5 min) and the running buffer (5 min). The buffer was prepared from 10 mM... 

Fig. 5 Chemical structures of indigoid (indigotine) and azo (amaranth, allura red, black PN, and tartrazine) dyes.

Reactive Dyes. These dyes form a covalent bond with the fiber, usually cotton, although they are used to a small extent on wool and nylon. This class of dyes, first introduced commercially in 1956 by ICI, made it possible to achieve extremely high washfastness properties by relatively simple dyeing methods. A marked advantage of reactive dyes over direct dyes is that their chemical structures are much simpler, their absorption spectra show narrower absorption bands, and the dyeings are brighter. The principal chemical classes of reactive dyes are azo (including metallized azo), triphendioxazine, phthalocyanine, formazan, and anthraquinone (see Section 3.1). 

A brief survey is given here of the chemical structure of some food dyes that have been approved for food coloration. From the chemical viewpoint several of the most frequently used synthetic food dyes belong to the azo series. 

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