Synthetic Chemistry And Technology Of C.I. Reactive Blue 220 And Its Reactive Intermediate

3-(Sulfatoethyl sulfonyl)aniline and 2-amino-4-(sulfatoethyl sulfonyl)-6-sulfo-phenol are very important intermediates of Reactive dyes. Former has been produced for many years, but followed with the improvement of technique, a series of new problems appeared, such as: byproducts are difficult to be separated during hydroxyethylation of sulfinic acid, and which leads to lower yield and higher costs. Based on reaction mechanism studied, an optimized production process was given.The addition mechanism of sodium 3-nitrobenzenesulfinate(SF) and ethylene oxide to prepare 3-(β-hydroxy-ethylsulfonyl)nitrobenzene(H) has been studied. The structures of main byproducts 1,2-bis(3-nitrophenylsulfonyl)ethane(DS) and 2,2'-(3"-nitrobenzene sulfonyl) ethyl ether(E) has been characterized. The forming mechanism of byproducts was shown as following:Due to the strong electron-withdrawing of nitro-group, compound H eliminate H2O to form corresponding vinyl sulfone(V) firstly, then V react with SF and H to generate DS and E respectively. The kinetic constants of the hydrolyzation and reversible reactions of E and V has been determined and the apparent activation energies were calculated by Arrhenius equation. The results of calculation showed that the apparent activation energy of hydrolysis of E is the most one, which means higher temperature is favorable to decomposition of E. According to the mechanism, the recycle and separation technique of byproduct has been presented and optimized.Sulfochlorination of 2-chloro-nitrobenzene, reduction of 4-chloro-3-nitro-benzene sulfonyl chloride and hydroxyethylation of sodium 4-chloride-3-nitrobenzene sulfinate (CSF) was improved. The yield of sulfochlorination was increased 15% by present of PCI3. The yield of sulfite reduction was improved 10% by surfactant as a dispersant and the process is more smooth and steady. The total yield of 2-amino-4-(sulfatoethyl sulfonyl)-6-sulfo-phenol was improved from 26% to 41%.During the hydroxyethylation of sodium 4-chloride-3-nitrobenzene sulfinate (CSF), there are three kinds of side reactions existed.1. Hydroxyethylation on the oxygen atom of sulfinic acid to form 2-hydroxyethyl 4-chloro-3-nitrobenzenesulfinate. Which proved that there is a tautomeric equilibrium existing in the sulfinic acid and the tautomeric equilibrium depends on the structure of sulfinic acid and surroundings. 2. The phenyl ring was attacked by nucleophilic agent and eliminated chloro atom.3. The product 2-nitro-4-(P-hydroxyethyl sulfonyl)chlorobenzene(CH) react with sulfinic acid to form bisulfonyl ethane derivative bi-(4-chloro-3-nitro-phenyl) sulfone.The synthetic and structural chemistry of formazane reactive dyes were studied. Formazane reactive blue 220 was prepared by 2-carboxyl-5-sulfo-bi-phenyl hydrazone and diazocompound from 2-amino-4-(sulfatoethyl sulfonyl)-6-sulfo-phenol in the presence of cupric ion. It is formed four-chelating Formazan at first, then converse to correspounding three-chelating Formazane after acidified. The structures were proved by Q-TOF Mass, and HPLC spectra. Compared with the structure of four coordination bond, the structure of three coordination bond has a narrower half peak width and the brighten shade. The relationship of structure and colour was discussed by comparingλmax of different formazane dyes. The dyeing performance of R.B.220 was evaluated by dyeing parameters and there commercialization was discussed.