DYE synthesis .pptx

METHYL ORANGE
ORANGE DYE
FAST RED B
MORDENT YELLOW
CONGO RED
METANIL YELLOW
CRYSODINE
ROSINDULINE
BASIC YELLOW 11
BASIC YELLOW 21
PRUSSIAN BLUE
ETC.. PROPERTIES AND APPLICATION

1. ch.1: Structures and synthesis By primal hirpara

2. Methyl orange

3. Orange dyes

4. Fast red B

5. MORDENT YELLOW

6. Congo Red It is an diazo dye, containing two azo groups. It is a direct dye for cotton. It is used as an indicator also( Blue in acidic solution and red in alkaline solution) Congo red is used as an indicator in acid-base titration. Congo red paper is used for testing acidity of the solution. Structure: NH 2 SO 3 Na N N N N NH 2 SO 3 Na Congo Red(Disodium salt)

7. Synthesis of Congo Red Congo red is synthesised by coupling between tetrazotised benzidine and two molecules of naphthionic acid. Step I : preparation of tetrazotised benzidine H 2 N N H 2 NaNO 2 , HCl o 0 -5 C 2 N Cl C l N 2 tetrazotised benzidine

8. Step II : Coupling of tetrazotised benzidine with naphthionic acid NH 2 SO 3 Na N N N N NH 2 SO 3 Na tetrazotised benzidine + ClN 2 N 2 Cl + H SO 3 Na H H NH 2 SO 3 Na -2HCl Coupling Congo Red Na O H HCl NH 2 SO 3 Na N N N N NH 2 SO 3 Na Congo Red(disodium salt)

9. Metanil yellow Metanilic acid is diazotized and coupled with diphenylamine gives  metanil yellow . Since Diphenyl amine is insoluble in water, coupling reaction has to be carried out by emulsifying diphenylamine in water before coupling .   Metanil Yellow  is used for dyeing silk and cotton fibers.

10. Chrysodine dye

11. Rosinduline The dye, Rosinduline 2 G (Colour Index No. 830, or Schultz’ Farbstofftabellen No. 674, synthesized by Hepp in 1890). It is the sodium salt of a monosulfonic acid of the compound shown in the formula (called Rosindon ). Rosindulin is a dark red solid that is sparingly soluble in water. The free acid can be precipitated one of the benzene rings; it is unknown in which. The dye has an intense scarlet red color The dye is easily soluble and stable both in the oxidized and reduced state even in very strongly alkaline solution and so differs, advantageously, from all dyes of a comparably negative potential range The dye can be reduced by colloidal palladium and hydrogen; the leucodye is easily soluble and very stable, Molecular Formula: C 28 H 18 N 3 NaO 6 S 2 Molecular Weight: 579.59 CAS No.: 25641-18-3 In  microscopy  , biological preparations are stained with Azocarmin G.  Histologically  , Azocarmine G (  Az  ) and  Aniline Blue (  An  ) are used as  Azan stains  to distinguish between cells and the surrounding matrix.

12. Rosinduline

13. Basic Yellow 11

14. Properties: Name: C.I.Basic  Yellow  11,C.I.48055 Molecular Structure:  Methine class Molecular Formula: C 21 H 25 ClN 2 O 2 Molecular Weight:  372.89 CAS Registry Number: 4208-80-4 Manufacturing Methods : 2-(1,3,3-Trimethylindolin-2-yl)acetaldehyde   and  2,4-Dimethoxybenzenamine  condensation.

15. Applications:  brilliant yellow. Talk of  green  light yellow powder. In cold water micro dissolve, is soluble in hot water, soluble in ethanol (solution for yellow). Used for the acrylic fabric dyeing, also used in vinegar fiber and PVC fiber color.

16. Basic Orange 21

17. Properties: Molecular Structure:  Multi- methine class Name: C.I.Basic   Orange  21 , Molecular Formula: C 22 H 23 ClN 2 Molecular Weight:  350.88 Manufacturing Methods :   2-( 1,3,3-Trimethylindolin-2-yl)acetaldehyde   and 2-Methyl-2H-indazole   in 90 ℃ in the condensation, and then dumped into the water, and translated into chloride. Properties : bright   yellow  orange. Soluble in water and ethanol are yellow, slightly soluble in cold water, soluble in hot water. Dye acrylic fiber as a bright yellow orange, tungsten filament in light slant  red  light. In 120 ℃ dyeing color when unchanged. In the dying encounter copper, iron ion colored light changes greatly. Applications: This product used for acrylic, two vinegar fiber, modified polyester dyeing and printing.

18. Basic information iupac name : 4- [[4-[(6-anilino-1-hydroxy-3-sulfonaphthalen-2-yl) diazenyl ]-5-methoxy-2-methylphenyl] diazenyl ]-5-hydroxynaphthalene-2,7-disulfonic acid ;Direct Blue 81;Direct blue 81 (C.I. 34215);Blue 81;C.I.34215;C.I.Direct Blue 81 M F: C46H27N7Na4O14S4 M W: 1121.96 Sirius Supra Blue Molecular Weight 793.8 g/ mol

19. Safranin B Solid safranin Safranin in aqueous solution

20. Basic Information: Safranines  are the azonium   compounds  of  symmetrical  2,8-dimethyl-3,7-diaminophenazine. They are obtained by the joint  oxidation  of one  molecule  of a  para -diamine with two molecules of a  primary amine ; by the condensation of  para -aminoazo compounds with primary amines, and by the action of  para -nitrosodialkylanilines with secondary  bases  such as diphenylmetaphenylenediamine . They are  crystalline  solids showing a characteristic green metallic  lustre ; they are readily soluble in water and  dye  blue or violet. They are strong bases and form stable monacid   salts . Their  alcoholic  solution shows a yellow-red  fluorescence . Phenosafranine is not very stable in the free state; its  chloride  forms green plates. It can be readily diazotized, and the diazonium salt when boiled with alcohol yields aposafranine or benzene induline , C 18 H 12 N 3 .

21. Basic Information: Molecular Structure: S ymmetrical 2,8-dimethyl-3,7-diaminophenazine   Name: Safranin Molecular Formula: C20H19ClN4 Molecular Weight: 350.85 CAS Registry Number:477-73-6 Solubility in Water: Soluble

22. Prussian blue

23. Introduction Prussian blue is a dark blue pigment with the idealized chemical formula Fe 7 (CN) 18 . This complex compound the formula can also be written as Fe 4 [Fe(CN) 6 ] 3 · xH 2 O. Another name for the color is Berlin blue or, in painting, Parisian or Paris blue. Turnbull's blue is the same substance, but is made from different reagents, and its slightly different color stems from different impurities. Prussian blue was the first modern synthetic pigment. It is employed as a very fine  colloidal dispersion , as the compound itself is not soluble in water. It is famously complex, [ Owing to the presence of variable amounts of other ions and the sensitive dependence of its appearance on the size of the colloidal particles formed when it is made. The pigment is used in  paints , and it is the traditional "blue" in  blueprints

24. Because it is easily made, cheap, nontoxic, and intensely colored, Prussian blue has attracted many applications. It was adopted as a pigment very soon after its invention and was almost immediately widely used in oil, watercolor, and dyeing. The dominant uses are for pigments: about 12,000 tonnes of Prussian blue are produced annually for use in black and bluish inks. A variety of other pigments also contain the material. Engineer's blue and the pigment formed on cyanotypes—giving them their common name blueprints. Certain crayons were once colored with Prussian blue (later relabeled midnight blue). It is also a popular pigment in paints. Similarly, Prussian blue is the basis for laundry bluing.

25. Properties Prussian blue is a microcrystalline blue powder. It is insoluble, but the crystallites tend to form a colloid. Such colloids can pass through fine filters. Despite being o ne of the oldest known synthetic compounds, the composition of Prussian blue remained uncertain for many years. Its precise identification was complicated by three factors: Prussian blue is extremely insoluble, but also tends to form colloids. Traditional syntheses tend to afford impure compositions. Even pure Prussian blue is structurally complex, defying routine crystallographic analysis.

26. Crystal structure The chemical formula of insoluble Prussian blue is Fe7(CN)18 · xH2O, where x = 14–16. The structure was determined by using IR spectroscopy, Mössbauer spectroscopy, X-ray crystallography, and neutron crystallography. Since X-ray diffraction cannot distinguish carbon from nitrogen, the location of these lighter elements is deduced by spectroscopic means, as well as by observing the distances from the iron atom centers. PB has a cubic lattice structure. Soluble PB crystals contain interstitial K+ ions; insoluble PB has interstitial water, instead. In ideal insoluble PB crystals, the cubic framework is built from Fe(II)–C–N–Fe(III) sequences, with Fe(II)–carbon distances of 1.92 Å and Fe(III)–nitrogen distances of 2.03 Å . One-fourth of the sites of Fe(CN)6 subunits are vacant (empty), leaving three such groups. The empty nitrogen sites are filled with water molecules, instead, which are coordinated to Fe(III).

27. The Fe(II) centers, which are low spin, are surrounded by six carbon ligands in an octahedral configuration. The Fe(III) centers, which are high spin, are octahedrally surrounded on average by 4.5 nitrogen atoms and 1.5 oxygen atoms (the oxygen from the six coordinated water molecules). Additional eight (interstitial) water molecules are present in the unit cell, either as isolated molecules or hydrogen bonded to the coordinated water. The composition is notoriously variable due to the presence of lattice defects, allowing it to be hydrated to various degrees as water molecules are incorporated into the structure to occupy cation vacancies. The variability of Prussian blue's composition is attributable to its low solubility, which leads to its rapid precipitation without the time to achieve full equilibrium between solid and liquid

28. Color Prussian blue is strongly colored and tends towards black and dark blue when mixed into oil paints. The exact hue depends on the method of preparation, which dictates the particle size. The intense blue color of Prussian blue is associated with the energy of the transfer of electrons from Fe(II) to Fe(III). Many such mixed-valence compounds absorb certain wavelengths of visible light resulting from intervalence charge transfer. In this case, orange-red light around 680 nanometers in wavelength is absorbed, and the reflected light appears blue as a result. Like most high chroma pigments, Prussian blue cannot be accurately displayed on a computer display. PB is electrochromic —changing from blue to colorless upon reduction. This change is caused by reduction of the Fe(III) to Fe(II) eliminating the intervalence charge transfer that causes Prussian blue's color.

29. Synthesis Necessary materials Laboratory tools: 1 beaker, 2 test tubes, 1 crucible, 1 asbestos sieve with tripod, 1 filter, 1 filtrating installation Chemical substances: K4[Fe(CN)6] crystals, FeCl3 solution (or any other Fe(III) solution) Method of working Prepare 200 ml of FeCl3 in the beaker. FeCl3 has a reddish-yellow colour and looks like this:

30. Then prepare two K4[Fe(CN)6] solution by dissolving 10 mg of potassium Ferro cyanide into 20 ml water in each test tube. Put enough FeCl3 for the precipitate to appear in both test tubes. The change of color is immediate: The chemical equation on which the reaction is based is: 4 FeCl3 + 3 K4[Fe(CN)6] -> Fe4[Fe(CN)6] + 12 KCl

31. Prepare the filtering installation and then put the solution from the second test tube on the beaker.

32. As you see, Prussian blue is perfectly insoluble in water, the only thing that is filtered being the FeCl3 solution that was used a bit too much:

33. Thank you