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Improved method for preparing pyrrolopyrrole-1,4-diketone derivative

A technology for materials and target substances, applied in the field of preparation of pyrrolopyrrole-1,4-dione derivatives, can solve the problems of inability to separate tert-amyl alcohol from water, complicated treatment process, increased production cost and the like

Active Publication Date: 2015-05-27
辽宁鸿港化工有限公司 +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

As a result, the separation and recovery of tert-amyl alcohol from this mixture is very complicated.
Because alcohol and water are azeotropic, tert-amyl alcohol cannot be separated from water by simple distillation or complex distillation
And if the liquid mixture is not treated, on the one hand, the production cost will be doubled, and on the other hand, the liquid mixture cannot be discharged directly

Method used

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  • Improved method for preparing pyrrolopyrrole-1,4-diketone derivative
  • Improved method for preparing pyrrolopyrrole-1,4-diketone derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Under nitrogen protection, put tert-amyl alcohol (690g) and sodium tert-amyloxide (230g) in a 2000ml four-neck flask, slowly heat to 110°C, add 4-phenylbenzonitrile (196g, 1.094mol) under stirring, After stirring evenly, di-tert-amyl succinate (183 g, 0.708 mol) was added dropwise, during which the temperature of the reactant was kept at 110-114°C. After the addition was complete, the reaction was kept for 6 hours. Transfer the reactant to a rotary vacuum dryer while it is hot, start the vacuum system to make the vacuum in the dryer reach 1-2mmHg, and then turn on the heating system of the dryer to let the tert-amyl alcohol in the reactant escape and condense The system condenses it to recover tert-amyl alcohol, and a total of tert-amyl alcohol (730g, containing the tert-amyl alcohol generated by the reaction) can be obtained.

[0023] After drying, transfer the dried reactant to a hydrolysis reactor, add methanol / water (2660ml, volume ratio 1:1), raise the temperature ...

Embodiment 2

[0026] Under nitrogen protection, put tert-amyl alcohol (690g) and sodium tert-amyloxide (230g) in a 2000ml four-necked flask, slowly heat to 110°C, add 4-chlorobenzonitrile (151g, 1.098mol) under stirring, and stir After uniformity, di-tert-amyl succinate (183g, 0.708mol) was added dropwise, during which the temperature of the reactant was kept at 110-114°C. After the addition was complete, the reaction was kept for 6h. Transfer the reactant to a rotary vacuum dryer while it is hot, start the vacuum system to make the vacuum in the dryer reach 1-2mmHg, and then turn on the heating system of the dryer to let the tert-amyl alcohol in the reactant escape and condense The system condenses it to recover tert-amyl alcohol, and a total of tert-amyl alcohol (720g, containing the tert-amyl alcohol generated by the reaction) can be obtained.

[0027]After drying, transfer the dried reactant to a hydrolysis reactor, add methanol / water (2660ml, volume ratio 1:1), heat up to 80°C, stir fo...

Embodiment 3

[0030] Under the protection of nitrogen, put tert-amyl alcohol (690g) and sodium tert-amyloxide (230g) into a 2000ml four-neck flask, heat slowly to 110°C, and add 4-tert-butylbenzonitrile (174.2g, 1.094mol) under stirring After stirring evenly, di-tert-amyl succinate (183g, 0.708mol) was added dropwise, during which the temperature of the reactant was kept at 110-114°C. After the addition was complete, the reaction was kept for 6h. Transfer the reactant to a rotary vacuum dryer while it is hot, start the vacuum system to make the vacuum in the dryer reach 1-2mmHg, and then turn on the heating system of the dryer to let the tert-amyl alcohol in the reactant escape and condense This was condensed by the system to recover tert-amyl alcohol, and a total of tert-amyl alcohol was obtained (725 g).

[0031] After drying, transfer the dried reactant to a hydrolysis reactor, add methanol / water (2660ml, volume ratio 1:1), heat up to 80°C, stir for 1h, adjust the pH to neutral with conc...

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Abstract

The invention relates to a method for preparing a pyrrolopyrrole-1,4-diketone derivative (the pyrrolopyrrole-1,4-diketone derivative can be used for preparing organic pigments). The method includes the main step: a target object is obtained through the reaction of succinic acid dialkyl ester and a nitrile compound at a temperature of 60 DEG C-140 DEG C in a sodium tert-pentoxide or potassium / tert-amyl alcohol medium. The method is characterized in that firstly, the adopted succinic acid dialkyl ester is succinic acid di-tert amyl ester; and secondly, after the reaction of succinic acid ditertiary amyl ester and the nitrile compound is stopped, the obtained mixture is heated and dried at the vacuum degree of 1-2 mmHg, the escaped tert-amyl alcohol is recovered at the same time, after heating and drying, the mixture heated and dried is transferred to a hydrolyzing reactor and diluted by carbinol / water, the generated sodium hydroxide is neutralized through inorganic acid, and the target object is obtained through liquid / solid separation. According to the invention, the steps for tert-amyl alcohol recovery are simplified, further, the cost in preparing the pyrrolopyrrole-1,4-diketone derivative is reduced.

Description

technical field [0001] The invention relates to a preparation method of pyrrolopyrrole-1,4-dione derivatives. Background technique [0002] Pyrrolopyrrole-1,4-dione and its derivatives can be used as organic pigments. For example, a class of DPP pigments listed by Ciba in 1986 is based on them (H.M.Smith, High Performance Pigment, 2002 , P159). [0003] Ciba Company disclosed a method for preparing pyrrolopyrrole-1,4-dione and its derivatives in EP 0094911 (or US. Pat. No. 4,579,949), wherein the more typical method is: in tert-amyl alcohol In sodium (potassium) / tert-amyl alcohol medium, pyrrolopyrrole-1,4-dione derivatives are obtained by condensation ring-closing reaction of dialkyl succinate and aromatic nitrile, aromatic heteronitrile or their substitutes. [0004] However, to separate the target substance from the reaction medium, complex post-processing is required. The typical post-treatment process is: dilute the above reactant with methanol / water, at this time, t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04C09B57/00
Inventor 沈永嘉张伟张毅吉张志刚施健美
Owner 辽宁鸿港化工有限公司
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