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Preparation method of 2,6-diaminotoluene

A technology for diaminotoluene and dichlorotoluene, which is applied in the field of catalytic ammoniation to prepare 2,6-diaminotoluene, can solve the problems of difficult industrialization, complex and harsh reaction conditions, and difficult to obtain raw materials, and achieves short chemical paths and reduced The effect of hidden safety hazards and obvious cost advantages

Active Publication Date: 2016-11-09
山东川成医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0015] The problem with the above route is that raw materials such as 2,6-dibromotoluene and triphenylaminosilane used in the reaction are not easy to obtain, and the reaction conditions are complex and harsh, making industrialization difficult

Method used

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  • Preparation method of 2,6-diaminotoluene
  • Preparation method of 2,6-diaminotoluene
  • Preparation method of 2,6-diaminotoluene

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Experimental program
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Embodiment 1

[0039] The preparation of embodiment 1 palladium ligand catalyst

[0040] A) In a two-necked flask equipped with magnetic stirring, add 250mL of distilled water, and pass through argon for 30 minutes;

[0041] B) Continue to maintain the argon flow, and add PdCl in sequence 2 (10mmol, 1.77g, 1 equiv) and KCl (20mmol, 1.42g, 2equiv), then seal the mouth of the flask with a rubber stopper, and stir the mixture in the bottle for 1 hour;

[0042] C) Inject excess cinnamyl chloride (Ph-allyl)Cl (30mmol, 4.58g, 3equiv) into the reaction flask through a rubber stopper, and the resulting system continued to react for 18 hours;

[0043] D) The reacted mixture was extracted 3 times with chloroform, the organic phases were combined, anhydrous MgSO 4 Drying, filtration, and desolventization under reduced pressure to obtain the corresponding dimer;

[0044] E) Put the ligand N-[2-bis(1-adamantyl)phosphophenyl]morpholine (2.2mmol, 1.02g) and 15mL dry tetrahydrofuran (THF) into a single-n...

Embodiment 2

[0046] The preparation of embodiment 2 palladium ligand catalyst

[0047] A) In a two-necked flask equipped with magnetic stirring, add 250mL of distilled water, and pass through argon for 30 minutes;

[0048] B) Continue to maintain the argon flow, and add PdCl in sequence 2 (10mmol, 1.77g, 1 equiv) and KCl (2.84g, 4 equiv), then seal the flask mouth with a rubber stopper, and stir the mixture in the bottle for 1 hour;

[0049] C) Inject excess cinnamyl chloride (Ph-allyl)Cl (4.58g, 3equiv) into the reaction flask through a rubber stopper, and the resulting system continued to react for 24 hours;

[0050] D) The reacted mixture was extracted 3 times with chloroform, the organic phases were combined, anhydrous MgSO 4 Drying, filtration, and desolventization under reduced pressure to obtain the corresponding dimer;

[0051] E) Put the ligand N-[2-bis(1-adamantyl)phosphophenyl]morpholine (2.2mmol, 1.02g) and 15mL dry tetrahydrofuran (THF) into a single-necked flask equipped w...

Embodiment 3

[0054] In a 1500mL reaction flask, add 500g of absolute ethanol, 100g of 2,6-dichlorotoluene, 300g of ammonia water and 6g of palladium complex catalyst, heat and start stirring under normal pressure, raise the temperature to 100°C, and keep it warm for 10 hours . After the reaction was completed, the catalyst was filtered off, the ethanol was evaporated, and 200 g of distilled water was added, the system was cooled to room temperature, filtered, and dried to obtain 57.4 g of 2,6-diaminotoluene.

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Abstract

The invention relates to the synthetic field of fine organic intermediates, specifically to a method for preparing 2,6-diaminotoluene by catalytic ammoniation. The method comprises the following steps: using anhydrous ethanol as a solvent, using 2,6-dichlorotoluene as a starting material, using ammonia water as an aminating agent, and heating and stirring the materials at normal pressure under the action of a palladium complex catalyst so as to prepare 2,6-diaminotoluene. By the synthetic method, high-temperature and high-pressure conditions in traditional technologies are avoided; economic cost is reduced, raw materials are simple and easy available, and reaction process is simple; and environmental protection is also considered, and raw materials harmful to the environment are avoided from being used in quantity.

Description

technical field [0001] The invention relates to the field of synthesis of fine organic intermediates, in particular to a method for preparing 2,6-diaminotoluene by catalytic amination. Background technique Background technique [0002] 2,6-Diaminotoluene is an important organic intermediate and product, which is widely used in many fields. It is often used in the synthesis of polyurethane soft foam plastics, coatings, rubber and adhesives. In addition, 2,6-diaminotoluene is also an important dye intermediate, which can be used in the synthesis of hair dyes. [0003] Currently reported 2, the preparation method of 6-diaminotoluene mainly contains the following: [0004] (1) Take 2-chloro-6-nitrotoluene as raw material [0005] The application document with the patent publication number CN104725242A reports that 2,6-diaminotoluene is obtained by using 2-chloro-6-nitrotoluene as a raw material through reduction and catalytic amination. [0006] [0007] The raw mater...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/10C07C211/51B01J31/24
CPCB01J31/2447B01J2531/0238B01J2531/824C07C209/10C07C211/51
Inventor 刘怀振郭明马居良
Owner 山东川成医药有限公司
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