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Bis(2-phthalimide)amine and preparation method thereof

A technology of phthalimide and phthalic anhydride, which is applied in the field of diamine and its preparation, can solve the problems of inapplicability to mass production, low product purity, complicated post-treatment, etc., and achieve low cost and high product purity. High, easy post-processing effect

Inactive Publication Date: 2019-11-29
SHAANXI UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, it is necessary to further study phthalimide compounds; and in the prior art, the synthetic method of phthalimide compounds generally uses triethylamine as catalyst or ethyl alcohol Acid anhydride is used as a solvent, first undergoes a low-temperature ring-opening reaction and then a high-temperature ring-closing reaction, which has low yield, high cost, long time-consuming, complicated post-processing, low product purity, and is not suitable for mass production

Method used

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  • Bis(2-phthalimide)amine and preparation method thereof
  • Bis(2-phthalimide)amine and preparation method thereof
  • Bis(2-phthalimide)amine and preparation method thereof

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preparation example Construction

[0028] The preparation method of the bis(2-phthalimide) amine is obtained through an electrophilic substitution-elimination reaction between phthalic anhydride and diethylenetriamine, wherein glacial acetic acid is used as a solvent, which can act as a proton Catalysis and low cost, using toluene as a water-carrying agent, so that the water generated in the reaction can be quickly separated through ring closure, so that the reaction moves forward and the yield of the product is improved.

[0029] The principle of electrophilic substitution-elimination is as follows,

[0030]

[0031] The preparation method of two (2-phthalimide) amines of the present invention specifically comprises the following steps,

[0032] Step 1, place a three-necked flask equipped with a stirrer in an oil bath, add 2.43-3.86g of diethylenetriamine, 9.27-12.95g of phthalic anhydride, and 40-60ml of glacial acetic acid into the three-necked flask, and then heat from room temperature to 90-100°C, at w...

Embodiment 1

[0039] The preparation method of two (2-phthalimide) amines of the present invention specifically comprises the following steps,

[0040] Step 1, place a three-necked flask equipped with a stirrer in an oil bath, add 2.78g of diethylenetriamine, 9.27g of phthalic anhydride, and 40ml of glacial acetic acid into the three-necked flask, and then heat it from room temperature to 90°C. carry out the ring-opening reaction;

[0041] Step 2, take 20ml of toluene and put it into the dropping funnel to prepare for dropping;

[0042] Step 3, in the case of constant heating, add toluene dropwise while stirring, and the drop can be completed within 30 minutes. The specific rate does not affect the progress of the reaction, and the temperature is raised to 115°C. The higher the temperature, the more conducive to ring closure, and continue the reaction for 4 hours;

[0043] Step 4, after the reaction, cool to room temperature, the mixed system obtained at this time is yellow, and the mixed ...

Embodiment 2

[0049] The preparation method of two (2-phthalimide) amines of the present invention specifically comprises the following steps,

[0050] Step 1, add 2.60g of diethylenetriamine, 10.08g of phthalic anhydride, and 50ml of glacial acetic acid into a three-necked flask, then heat from room temperature to 97°C;

[0051] Step 2, take 22ml of toluene and put it into the dropping funnel and prepare to add it dropwise;

[0052] Step 3, under the condition of constant heating, add toluene dropwise while stirring, and finish dropping after 30 minutes, then raise the temperature to 118°C, the higher the temperature, the better the ring closure, and continue the reaction for 2 hours;

[0053] Step 4, after the reaction, cool to room temperature, the mixed system obtained at this time is yellow, and the mixed system is rotary evaporated at 65°C until no liquid flows out, that is, the solvent glacial acetic acid is removed, and a dark yellow viscous mixed system is obtained ;

[0054] Ste...

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Abstract

The invention provides bis(2-phthalimide)amine and a preparation method thereof. The method includes: step 1, heating a mixed system composed of diethylenetriamine, phthalic anhydride and glacial acetic acid to 90-100DEG C to obtain a mixed system A; step 2, heating the mixed system A to 115-130DEG C, then carrying out reaction for 1-4h, adding toluene continuously in the heating process to obtaina mixed system B; and step 3, sequentially removing glacial acetic acid and impurities from the mixed system B to obtain a product, and washing and drying the product in order to obtain bis(2-phthalimide)amine. Part of positive charges carried by carbonyl on phthalic anhydride interact with lone electron pairs on N atoms of diethylenetriamine primary amine to form a transition complex, and then amic acid can be formed, and finally the temperature is raised, acid in amic acid molecules and another H atom in the primary amine are subjected to high-temperature removal of one water molecule so asto form a final imide structure, and the yield and purity of the product are high.

Description

technical field [0001] The invention belongs to the technical field of imide compounds, in particular to bis(2-phthalimide)amine and a preparation method thereof. Background technique [0002] The imide compound is a class of organic compounds widely used in biology, synthetic chemistry, medicine, and polymer chemistry. The imide compound has a unique molecular structure, and the N atom of the hybrid orbital has a lone pair Electrons, with good coordination ability, often exhibit good anticancer, antibacterial and antiviral activities. Due to its weak fluorescent activity, imide can react quantitatively with physiologically active thiol cysteine ​​and glutathione to generate strongly fluorescent substances, which can be used for disease monitoring and clinical diagnosis and treatment; Amine compounds can also be used to synthesize some important biological natural products such as panmycin, pig bilirubin, etc., and can be used as monomers for synthesizing polyamide polymers...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48
CPCC07D209/48
Inventor 郭睿徐康张晓飞闫育蒙马丽娟
Owner SHAANXI UNIV OF SCI & TECH
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