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Preparation method of N-(3-hydroxypropyl)phthalimide and catalyst for method

A technology of catalyst and phthalimide, which is applied in the field of preparation of fine chemicals, can solve the problems of high cost and high catalyst toxicity, and achieve the effects of high yield, low catalyst cost and reduced production cost

Pending Publication Date: 2020-05-08
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are only a few additions of amines and enols against the Markov law, and the catalyst used is an expensive metal ruthenium complex, and the catalyst toxicity is relatively high.

Method used

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  • Preparation method of N-(3-hydroxypropyl)phthalimide and catalyst for method
  • Preparation method of N-(3-hydroxypropyl)phthalimide and catalyst for method
  • Preparation method of N-(3-hydroxypropyl)phthalimide and catalyst for method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of catalyst:

[0043] Under nitrogen atmosphere, add 216.0g (1mol) FeBr 2 Dissolve 280.0g (5mol) Fe powder in 108.1g (1.5mol) tetrahydrofuran and react for 3 hours, and remove the solvent by distillation under reduced pressure to obtain off-white 342.5g (0.95mol) FeBr 2 (THF) 2 Precipitation; further solid 497.5 (0.95mol) HN (CH 2 CH 2 PCy 2 ) 2 Dissolve in 100mL CH 3 Add dropwise to 342.5 (0.95mol) FeBr after CN 2 (THF) 2, refluxed for 4 hours, and further reacted at room temperature for 5 hours; the obtained solution was frozen with liquid nitrogen, passed through carbon monoxide, reacted at room temperature, and the reaction was stopped when the color of the solution changed to dark purple, and the solvent was distilled off under reduced pressure to obtain Purple solid; further recrystallized in dichloromethane as a solvent to obtain pure iron-based chelate catalyst 1, 667.4 g (0.94 mol).

[0044] Elemental Analysis: C 49.05%Fe 7.92%P 8.71%Br 22....

Embodiment 2

[0048] Preparation of catalyst:

[0049] Except using HN (CH 2 CH 2 PiPr 2 ) 2 instead of HN (CH 2 CH 2 PCy 2 ) 2 Other than that, the preparation process was the same as that of Example 1, and finally, 510.57 g (0.93 mol) of iron-based chelate catalyst 2 was obtained.

[0050] Elemental analysis: C 37.16% Fe 10.20% P 11.30% Br 29.14% O 2.91% H6.74% N2.55%.

[0051] 54.9g (0.1mol) iron-based chelate catalyst 2, the mass fraction of 15% NaBH (CH 3 COO) 3 422.1 g of aqueous solution and 1.5 L of toluene were mixed and stirred for 20 min to form a red homogeneous solution. Then 1471.3 g (10 mol) of phthalimide, 2323.2 g (40 mol) of allyl alcohol, and a mass fraction of 20% K 3 CO 3 885.0g of the aqueous solution was added to a 10L reactor, stirred for 5min and mixed evenly, and then replaced with nitrogen for 3 times, then the oil bath was heated to 80 ° C and normal pressure for 24 hours, after the reaction was completed, it was returned to room temperature, and the ...

Embodiment 3

[0054] 71.0 g (0.1 mol) of iron-based chelate catalyst 1 prepared in Example 1, with a mass fraction of 15% NaBH (CH 3 COO) 3 422.1 g of aqueous solution and 2 L of cyclohexane were mixed and stirred for 20 min to form a red homogeneous solution. Then 1471.3 g (10 mol) of phthalimide, 2904.0 g (50 mol) of allyl alcohol, and a mass fraction of 20% K 3 CO 3 885.0g of the aqueous solution was added to a 10L reactor, stirred for 5min and mixed evenly, and then replaced with nitrogen for 3 times, then the oil bath was heated to 80 ° C and normal pressure for 24 hours, after the reaction was completed, it was returned to room temperature, and the organic matter was extracted with dichloromethane. phase, the dichloromethane was distilled off under reduced pressure, and 1854.82 g of the product was obtained after drying, with a conversion rate of 99.0% and a selectivity of 98.0%.

[0055] Elemental analysis: C 64.42% H 5.32% N 6.91% O 23.35%.

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PUM

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Abstract

The invention relates to a method for preparing N-(3-hydroxypropyl)phthalimide and a catalyst used in the method, the method comprises making phthalimide and allyl alcohol react in a solvent in the presence of an iron-based catalyst, a sodium salt and a potassium salt in an inert atmosphere to obtain N-(3-hydroxypropyl)phthalimide. According to the method, phthalimide and allyl alcohol are used asraw materials, the cheap iron chelate catalyst Fe-PNP is used for replacing an expensive ruthenium catalyst, the product is directly obtained through a reverse Markov addition one-step method, and the method is simple in process, low in cost and high in yield and conversion rate.

Description

technical field [0001] The invention belongs to the technical field of preparation of fine chemicals, and in particular relates to a preparation method of N-(3-hydroxypropyl)phthalimide and a catalyst used in the method. Background technique [0002] N-(3-hydroxypropyl)phthalimide is an important pharmaceutical and pesticide intermediate, and can also be used for the modification of polyester. The hydroxypropyl segment connected to N helps to improve the rigidity of polyester. At present, the methods for producing N-(3-hydroxypropyl)phthalimide include phthalic anhydride, 3-aminopropanol amination and reaction of phthalimide potassium salt with 3-chloro-1-propanol. The purity requirements of the reagents required by the method are relatively high, and the analytical purity is usually required to be above 99%. [0003] Allyl alcohol is an intermediate commonly used in the production of glycerin, pharmaceuticals, pesticides, fragrances and cosmetics, and can be obtained by ac...

Claims

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Application Information

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IPC IPC(8): C07D209/48B01J31/24B01J31/20C07C213/02C07C215/08
CPCB01J31/20B01J31/2409B01J2231/32C07C213/02C07D209/48C07C215/08
Inventor 刘喆袁帅黎源董龙跃
Owner WANHUA CHEM GRP CO LTD
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