Pigment Yellow 74 synthesis
- Product Name:Pigment Yellow 74
- CAS Number:6358-31-2
- Molecular formula:C18H18N4O6
- Molecular Weight:386.36
Yield:-
Reaction Conditions:
Stage #1:2-methoxy-4-nitrophenylamine with hydrogenchloride;C19H23N7O8S3;sodium nitrite in water at 10; for 1 h;
Stage #2:2'-methoxyacetoacetanilide with sodium hydroxide;sodium acetate;acetic acid in water; pH=6 at 25 - 90; for 2.5 h;
Steps:
1 [Synthesis of Pigment]; (Example 1)
To a mixed solution of 700 g of water and 315 g of 35% hydrochloric acid (3.02 mol) were added 181.4 g of 4-nitro-2-methoxyaniline (1.08 mol) and 68.8 g of base A (0.12 mol) and stirred to allow for dispersion. After cooling this dispersion by adding about 600 g of ice, thereto was added a solution of 87 g of sodium nitrite (1.26 mol) dissolved in 100 g of water. The mixture was stirred for one hour while keeping the temperature of 10°C or less, and excess nitrous acid was eliminated with sulfamic acid followed by filtration to give a diazotization liquid. On the other hand, a coupling agent liquid was prepared as follows. After dissolving 100 g of sodium acetate (0.74 mol) in 8900 g of water, thereto was added 256.7 g of acetoacetyl-o-anisidide (1.24 mol) to allow for dispersion. Next, thereto was added and dissolved 185 g of 30% caustic alkali of sodium (1.39 mol). To thus resulting solution, 110 g of 80% acetic acid (1.47 mol) was added dropwise to adjust the pH of 6. Accordingly, a coupling agent liquid was obtained through adjusting the temperature of 25°C.To this coupling agent liquid was added dropwise the diazotization liquid described above over 120 minutes to complete the coupling reaction. Next, the temperature was elevated to 90°C, and the mixture was subjected to a heat treatment for 30 min. Thereafter, by-product salts and the like were removed by filtration and washing with water. Then the product was dried in a drying oven at 80°C. This dried pigment was subjected to grinding, and the yield of thus resulting yellow pigment composition was 497.0 g (1.17 mol), with the mean particle size of the pigment of 0.08 m.
References:
Sanyo Color Works, Ltd. EP1424370, 2004, A1 Location in patent:Page 8
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