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A technology for p-phenylenediamine and p-dichlorobenzene, which is applied in the field of preparation of p-phenylenediamine, can solve the problems of low atom utilization rate, seriousness, long reaction time, etc. The effect of mild reaction conditions
Active Publication Date: 2019-02-15
JIANGSU YANGNONG CHEM GROUP +2
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[0008] Among the above synthetic routes, route one is the main method of industrialization at present, with mature technology, high yield and good selectivity, but the raw material p-nitroaniline needs to be obtained by nitration of chlorobenzene and ammonolysis, the synthesis of raw materials is cumbersome, the utilization rate of atoms is low, and the nitration The process pollution is serious...
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Embodiment 1
[0022] In a 1L autoclave, add 117.72g p-dichlorobenzene (99.9%, 0.8mol), 437.14g ammonia water (35%, 9.0mol), 7.93g cuprous chloride (99.9%, 0.08mol), 28.32g Mannich base ligand L3 (0.08mol), after the feeding is completed, the temperature is raised to 130°C, the stirring speed is 600rpm, the heat preservation reaction is 6hr, and the pressure is 2.2Mpa. After the reaction, the ammonia is recovered by cooling down and releasing the pressure, and 77.15g of p-benzene Diamine, content 99.9%, yield 89.2%.
Embodiment 2
[0024] In 1L autoclave, add 58.86g p-dichlorobenzene (99.9%, 0.4mol), 355.56g ammonia water (45%, 8.0mol), 0.76g cuprous iodide (99.9%, 0.004mol), 4.20g Mannich base ligand L1 (0.008mol), after the feeding is completed, the temperature is raised to 150°C, the stirring speed is 600rpm, the heat preservation reaction is 10hr, and the pressure is 4.2MPa. After the reaction is completed, the temperature is lowered and the pressure is released to recover ammonia. Diamine, content 99.9%, yield 90.6%.
Embodiment 3
[0026] Add 88.30g p-dichlorobenzene (99.9%, 0.6mol), 353.80g ammonia water (40%, 7.2mol), 0.30g cuprous chloride (99.9%, 0.003mol), 3.93g Mannich base ligand in 1L autoclave L2 (0.009mol), after the feeding is completed, the temperature is raised to 150°C, the stirring speed is 600rpm, the heat preservation reaction is 24hr, and the pressure is 3.2MPa. After the reaction, the ammonia is recovered by cooling down and releasing the pressure. Diamine, content 99.9%, yield 86.5%.
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Abstract
The invention discloses a preparation method of p-phenylenediamine. The preparation method comprises the following steps: adding paradichlorobenzene, ammonia water, the concentration of which is 35-45%, a catalyst and a Mannich alkaline ligand into a high pressure kettle; heating the mixture to 130-150 DEG C; stirring the mixture at a rotating speed of 600 rpm, wherein the reaction pressure is 2.0-4.5 MPa, carrying out an insulating reaction for 6-24 hours; after the reaction, reducing the temperature and relieving the pressure to recover ammonia; and carrying out desolventization and negativepressure distillation on kettle materials to obtain p-phenylenediamine, wherein the molar ratio of paradichlorobenzene and ammonia water is 1: 10 to 1: 20; the molar ratio of the catalyst and paradichlorobenzene is 0.005: 1 to 0.1: 1; the molar ratio of the Mannich alkaline ligand and the catalyst is 1: 1 to 3: 1; the catalyst is one of cuprous iodide, cuprous chloride, cuprous bromide, cuprous oxide, copper sulfate, copper chloride, cupric acetate and copper trifluoroacetate; the Mannich ligand structure is as shown in a formula, in which R is t-Bu or Cl or CH3. The preparation method is mild in reaction condition, efficient, good in selectivity, high in yield and suitable for industrial production of p-phenylenediamine on a large scale.
Description
technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of p-phenylenediamine. Background technique [0002] p-Phenylenediamine, also known as Wuersi D, is one of the simplest aromatic diamines, with a white to lavender crystal appearance, a melting point of 140°C, a boiling point of 264°C, and a relative density of 1.21. Slightly soluble in cold water, soluble in hot water, easily soluble in alcohol, ether and chloroform. As a traditional chemical intermediate, it is widely used in dyestuff, rubber, national defense and other industries. Azo dyes can be produced in the dye industry, rubber antioxidants can be produced in the rubber industry, and para-aramid fibers can be produced in the national defense industry. In addition, p-phenylenediamine is also the main raw material of gasoline polymerization inhibitor and photographic developer. At present, in the field of rubber additives, the new rubber ...
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