Process for producing aromatic diaether dianhydride monomer

A dianhydride monomer and aromatic technology, used in the synthesis of dianhydride monomers, can solve problems such as high sealing requirements, easy oxidation of phenol, and reduced conversion rate of phthalic anhydride

Inactive Publication Date: 2009-04-08
NANJING UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The phenol used in the tetracyanodiphenyl ether hydrolysis method is very easy to oxidize, and it is required to be absolutely anhydrous and oxygen-free during the feeding and reaction process, which requires extremely high sealing performance of the device. Nitrogen must be dehydrated first, which is not easy in industrial production. accomplish
Although this method avoids the deficiency of using methylamine, it still uses phthalic anhydride as the starting material. Because the temperature of the reaction is 150°C to 175°C, the hydrolysis of phthalic anhydride is accelerated at this temperature, which reduces the conversion rate of phthalic anhydride; in addition, nitration Preparation of nitroalkylphthalimides using large quantities of concentrated nitric and sulfuric acids

Method used

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  • Process for producing aromatic diaether dianhydride monomer
  • Process for producing aromatic diaether dianhydride monomer
  • Process for producing aromatic diaether dianhydride monomer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0086] Add 11.2 g KOH and 160 g absolute ethanol into a 500 ml three-neck flask, stir until dissolved; then add 38.4 g 4-nitrophthalimide, stir at 25°C for 4 hours; filter after the reaction, collect the mother liquor, and distill under reduced pressure Recover absolute ethanol; vacuum-dry the filter cake (potassium salt) at 80°C.

[0087] Add the potassium salt prepared above into a 500ml three-neck flask, then add 25.3g benzyl chloride and 100gDMF, raise the temperature to 130°C, and react at a constant temperature for 4h; Purify and dry under vacuum at 120°C for 2 hours to obtain 4-nitro-N-benzylphthalimide.

[0088]Alternatively, add 51.8gK to a 500ml three-necked flask 2 CO 3 , 57.9g of 4-nitrophthalimide, 75.9g of benzyl chloride and 200g of DMF, stirred and heated up to 140°C for 6 hours at a constant temperature; after the reaction was completed, the temperature was lowered to 50°C, solids were precipitated, filtered, and firstly used 2% Wash with dilute hydrochlori...

Embodiment 2

[0093] Add 10.5g KOH and 130g absolute ethanol into a 500ml three-neck flask, stir until dissolved; then add 36.0g 3-nitrophthalimide, stir at 35°C for 4 hours; filter after the reaction, collect the mother liquor, and distill under reduced pressure Recover absolute ethanol; vacuum-dry the filter cake (potassium salt) at 85°C.

[0094] Add the potassium salt prepared above into a 500ml three-neck flask, then add 23.7g of benzyl chloride and 90g of DMF, raise the temperature to 140°C, and react at a constant temperature for 6h; Purify and dry in vacuum at 120°C for 2 hours to obtain 3-nitro-N-benzylphthalimide.

[0095] Add 19.1g of biphenol into a 500ml three-necked flask, blow nitrogen, add 125ml of dimethyl sulfoxide, 18.7g of 50% NaOH aqueous solution, then add 75ml of toluene, reflux to remove water for 5 hours, and distill the toluene out after the water separation is completed . Cool to 55°C, add 29.3g of the above-prepared product 3-nitro-N-benzylphthalimide, 1.5g tet...

Embodiment 3

[0099] Add 13.5g KOH and 140g absolute ethanol into a 500ml three-neck flask, stir until dissolved; then add 46.3g 4-nitrophthalimide, stir at 30°C for 5h; filter after the reaction, collect the mother liquor, and distill under reduced pressure Recover absolute ethanol; filter cake (potassium salt) is vacuum-dried at 90°C.

[0100] Add the potassium salt prepared above into a 500ml three-neck flask, then add 32.8g of bromobutane and 90g of DMF, raise the temperature to 140°C, and react at a constant temperature for 6h; Purified with ethylene glycol methyl ether and dried in vacuum at 100°C for 2 hours to obtain 4-nitro-N-butylphthalimide.

[0101] Add 22.8g bisphenol A into a 500ml three-neck flask, blow nitrogen, add 100ml dimethyl sulfoxide, 16g 50% NaOH aqueous solution, then add 50ml toluene, reflux to remove water for 6 hours, and distill the toluene out after the water separation is completed. Cool to 70°C and add 45.3g of the product 4-nitro-N-butylphthalimide prepared...

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Abstract

The invention relates to a method for synthesizing a dianhydride monomer, in particular to a method for synthesizing an aromatic HQEDA monomer. The method adopts a 3(4) substituted phthalimide to prepare HQEDA and provides novel middle steps for preparing the HQEDA. The method comprises the following steps: preparing a 3 (4) substituted-N-alkyl (aryl) phthalimide from the 3(4) substituted phthalimide through Gabriel reaction principle or by adding a salifying agent and halocarbon into an apolar aprotic solvent to react; and using the prepared 3 (4) substituted-N-alkyl (aryl) phthalimide to prepare bis imide and the bis ether anhydride. The method has the advantages that raw materials are easily available, preparation method is simple and easy to operate, and the purity and yield of the prepared 3 (4) substituted-N-alkyl (aryl) phthalimide are obviously higher than that of the prior method.

Description

technical field [0001] The invention relates to a method for synthesizing dianhydride monomers, in particular to a method for synthesizing aromatic diether dianhydride monomers. Background technique [0002] Diether dianhydride is one of the important monomers for the synthesis of ether anhydride polyimide resins. It is used to prepare high-temperature-resistant terminals, high-strength mechanical parts, connectors, and special parts such as corrosion-resistant, flame-retardant, and radiation-resistant. Intermediates of polyetherimide. It is also an excellent modifier for resins. By introducing an ether bond (-O-) into the dianhydride monomer, the originally insoluble PI was dissolved in tetrahydrofuran (THF), N-methylpyrrolidone (NMP), dimethylsulfoxide (DMSO), N,N' - Commonly used organic solvents such as dimethylformamide (DMF) and N, N'-dimethylacetamide (DMAc), and make it have a lower glass transition temperature and improve processing performance. [0003] There ar...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/89
Inventor 黄培黄丽萍
Owner NANJING UNIV OF TECH
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