CN116041242A - Synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane - Google Patents

Synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane Download PDF

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CN116041242A
CN116041242A CN202310038822.8A CN202310038822A CN116041242A CN 116041242 A CN116041242 A CN 116041242A CN 202310038822 A CN202310038822 A CN 202310038822A CN 116041242 A CN116041242 A CN 116041242A
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aminophenyl
amino
bis
trimethylindan
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胡锦平
吴建华
冯二龙
张培锋
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Changzhou Sunchem New Material Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
    • C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
    • C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
    • C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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Abstract

The invention discloses a synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane, which comprises the steps of reacting 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane with maleic anhydride to obtain a mixture of an intermediate I and an intermediate II; the mixture is dehydrated and closed in the presence of an alkaline catalyst and acetic anhydride to obtain a reaction solution; and (3) eliminating impurities by adopting an alkaline reagent and crystallizing by adopting toluene to obtain the N, N' -bis (maleimide group) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan. According to the method, the alkaline reagent is adopted to remove impurities after the dehydration ring-closure reaction, so that the product purity of more than 99% can be obtained, and the ethyl acetate is adopted as a reaction solvent, so that the method is easy to recycle and reuse, the wastewater treatment difficulty is greatly reduced, and the production cost is effectively reduced.

Description

Synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan.
Background
Bismaleimide (BMI) is another type of resin system derived from a polyimide resin system, is a difunctional compound taking maleimide as an active end group, has excellent heat resistance, weather resistance, electrical insulation, wave permeability, radiation resistance, flame retardance, good mechanical property and dimensional stability, has fluidity, moldability and molding manufacturability similar to those of epoxy resin, and overcomes the defect of relatively low heat resistance of the epoxy resin, so that the bismaleimide resin has been rapidly developed and widely used in recent years. As one of high-performance polymers having high strength, high modulus and relatively low density, BMI is widely used in the industrial fields of aviation, aerospace, machinery, electronics, transportation, etc., resin matrix of advanced composite materials, high-temperature resistant insulating materials, adhesives, etc.
N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindene-mane is a novel bismaleimide monomer, a brown solid, of the formula: c (C) 26 H 22 O 4 N 2 Relative molecular weight: 426.47 because it is a two-component isomer mixture, it has the characteristics of low melting point, strong moldability and easy processing and forming, and because it contains 6 secondary tertiary carbons in its structure, compared with other structural bismaleimide resin monomers, it has better solubility in general solvents, higher reactivity with aromatic amine, and the prepared material has excellent toughness, moisture resistance and stability.
No literature report on the synthesis of N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane has been found.
Disclosure of Invention
The invention aims to solve the problems and provide a method for synthesizing N, N' -bis (maleimide group) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane with high purity.
The technical scheme for realizing the aim of the invention is as follows: a method for synthesizing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane comprises the following steps:
(1) reacting 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan with maleic anhydride in ethyl acetate to obtain a mixture of intermediate I and intermediate II;
(2) the mixture of the intermediate I and the intermediate II obtained in the step (1) is subjected to dehydration ring-closure reaction in ethyl acetate in the presence of an alkaline catalyst and acetic anhydride to obtain a reaction solution containing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan;
(3) and (3) carrying out impurity elimination treatment on the reaction liquid obtained in the step (2) by adopting an alkaline reagent, and then crystallizing by adopting toluene to obtain the N, N' -bis (maleimide group) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan.
The reaction temperature in the step (1) is 5-50 ℃.
In the step (1), the 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane is a mixture of two isomers of 5-amino-1- (4-aminophenyl) -1, 3-trimethylindane and 6-amino-1- (4-aminophenyl) -1, 3-trimethylindane, and the molar ratio thereof is 1:0.6-1:1.5.
In the step (1), the molar ratio of the 5 (6) -amino-1- (4' -aminophenyl) -1, 3-trimethylindane to the maleic anhydride is 1:2 to 1:5, preferably 1:2.5 to 1:3.
In the mixture of the intermediate I and the intermediate II obtained in the step (1), the mol ratio of the intermediate I to the intermediate II is 1:0.6-1:1.5.
The structural formula of the intermediate I is as follows:
Figure SMS_1
。
the structural formula of the intermediate II is as follows:
Figure SMS_2
。
the dehydration ring-closure reaction temperature in the step (2) is 30-50 ℃.
In the step (2), the molar ratio of the mixture of the intermediate I and the intermediate II to the acetic anhydride is 1:3-1:8.
In the step (2), the basic catalyst is triethylamine, pyridine, N-diisopropylethylamine or DMAP; the molar ratio of the mixture of the intermediate I and the intermediate II to the basic catalyst is 1:0.2-1:3, preferably 1:0.7-1:2.6.
In the step (3), the reaction temperature for removing impurities is 70-75 ℃.
In the step (3), the alkaline reagent is triethylamine, pyridine, N-diisopropylethylamine or DMAP; the molar ratio of the mixture of the intermediate I and the intermediate II to the alkaline agent is 1:0.5-1:4, preferably 1:1-1:2.5.
In the step (3), the structure of the impurity is as follows:
Figure SMS_3
、/>
Figure SMS_4
、/>
Figure SMS_5
、/>
Figure SMS_6
。
the N, N ' -bis (maleimide group) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane obtained in the step (3) is a mixture of two isomers of N, N ' -bis (maleimide group) -5-amino-1- (4-aminophenyl) -1, 3-trimethylindane and N, N ' -bis (maleimide group) -6-amino-1- (4-aminophenyl) -1, 3-trimethylindane in a molar ratio of 1:0.6 to 1:1.5.
Wherein: the structural formula of N, N' -bis (maleimido) -5-amino-1- (4-aminophenyl) -1, 3-trimethylindan (CAS number 123811-63-2) is as follows:
Figure SMS_7
。
the structural formula of N, N' -bis (maleimido) -6-amino-1- (4-aminophenyl) -1, 3-trimethylindan (CAS number 958832-00-3) is as follows:
Figure SMS_8
。/>
the invention has the positive effects that:
(1) The method of the invention adopts alkaline reagent to eliminate impurities after dehydration ring-closure reaction, thereby obtaining the purity of the product of more than 99 percent.
(2) The method adopts ethyl acetate as a reaction solvent, is easy to recycle, greatly reduces the wastewater treatment difficulty and effectively reduces the production cost.
Drawings
FIG. 1 is a liquid chromatogram of a mixture of intermediate I and intermediate II obtained in step (1) of example 1.
FIG. 2 is a mass spectrum of a mixture of intermediate I and intermediate II obtained in step (1) of example 1.
Fig. 3 is a mass spectrum of the impurity obtained in step (2) of example 1.
FIG. 4 is a liquid chromatogram of the target product obtained in example 1.
FIG. 5 is a mass spectrum of the target product obtained in example 1.
Detailed Description
Example 1
The synthesis method of N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane of this example has the steps of:
(1) 200g of ethyl acetate and 110.5g of maleic anhydride (1.13 mol) were added to a 500mL three-necked flask, and dissolved by stirring to obtain a maleic anhydride ethyl acetate solution.
400g of ethyl acetate and 100g of 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan (0.38 mol, equimolar isomer) are added into a 1L three-necked flask under stirring, the temperature is reduced to 0 to 5 ℃, the maleic anhydride ethyl acetate solution is added dropwise, the temperature is controlled to 3 to 15 ℃ in the dropwise adding process, the mixture is stirred and reacted for 30 minutes at the temperature of 18+/-2 ℃ at first, and then the mixture is heated to 43+/-2 ℃ and stirred and reacted for 30 minutes.
After the reaction is finished, slowly cooling to 33+/-2 ℃ (about 1.5 hours when cooling is carried out), precipitating a large amount of granular solid, continuously stirring for 1 hour, crystallizing completely, finally cooling to 22+/-2 ℃, stirring for 2 hours, filtering, rinsing the filter cake with 100g of ethyl acetate, and drying by blowing at 40-45 ℃ until the weight is constant, thus obtaining 160.8g of a mixture of the yellow-green granular intermediate I and the intermediate II, wherein the purity is 99.6%, and the yield is 92.6%.
The liquid chromatogram of the mixture is shown in figure 1, and the mass chromatogram is shown in figure 2.
(2) 700g of ethyl acetate and 83.9g of acetic anhydride (0.82 mol) are sequentially added into a 2L three-necked flask, 100g (0.22 mol) of the mixture of the intermediate I and the intermediate II obtained in the step (1) is slowly added under stirring, the mixture is stirred at 20-25 ℃ for 30min, then 56.0g of triethylamine (0.55 mol) is dropwise added under stirring, the temperature is controlled at 22-33 ℃ during the dropwise adding process, the mixture is stirred at 35-40 ℃ for 8h, and the sampling HPLC is controlled: the peak area of the target product and the peak area of the impurity are more than or equal to 98 percent, and the mass spectrum of the impurity is shown in figure 3.
(3) After the reaction is finished, the temperature is reduced to 5 to 15 ℃, 580g of Na with 15 weight percent is added dropwise 2 CO 3 The temperature of the aqueous solution is controlled to be less than 25 ℃ in the dropping process, stirring is continued for 1h after the dropping, standing and layering are carried out, the upper organic layer is washed by 100g of purified water and then is transferred to a 2L three-mouth bottle, 50g of triethylamine (0.50 mol) is added under stirring, and the temperature is raised to 70-75 ℃ for reaction for 6h.
After the reaction is finished, cooling to 20-25 ℃, adding 150g of purified water, stirring for 30min, standing for layering, vacuum concentrating an upper organic layer to dryness at 45-90 ℃, dropwise adding 580g of toluene into the concentrated solution under stirring, controlling the temperature to 90-100 ℃ in the dropwise adding process, slowly cooling to 66-70 ℃ after dropwise adding, stirring for 1.5h at the temperature, precipitating a large amount of solids, continuously cooling to 5-10 ℃, filtering, leaching a filter cake with 100g of ice toluene, distilling to recover toluene, and vacuum drying wet products at 80-85 ℃ for 14h to obtain 80.1g of brown target products with the purity of 99.2% and the yield of 86.9% based on the mixture of the intermediate I and the intermediate II in the step (2).
The liquid chromatogram of the target product is shown in fig. 4, and the mass spectrum is shown in fig. 5.
Example 2
The synthesis method of N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane of this example has the steps of:
(1) 200g of ethyl acetate and 110.5g of maleic anhydride (1.13 mol) were added to a 500mL three-necked flask, and dissolved by stirring to obtain a maleic anhydride ethyl acetate solution.
550g of ethyl acetate and 120g of 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan (0.45 mol) are added into a 2L three-mouth bottle under stirring, the temperature is reduced to 0-5 ℃, the maleic anhydride ethyl acetate solution is added dropwise, the temperature is controlled to 2-13 ℃ in the dropwise process, the mixture is stirred and reacted for 30min at 20+/-2 ℃ at first, and then the mixture is heated to 45+/-2 ℃ and stirred and reacted for 35min.
After the reaction is finished, slowly cooling to 33+/-2 ℃ (about 1h when cooling is performed), precipitating a large amount of granular solid, continuously stirring for 1h, completely crystallizing, finally cooling to 21+/-2 ℃, stirring for 2h, filtering, rinsing the filter cake with 90g of ethyl acetate, and drying by blowing at 40-45 ℃ until the weight is constant, thereby obtaining 196.7g of a mixture of the yellow-green granular intermediate I and the intermediate II, wherein the purity is 99.1%, and the yield is 94.4%.
(2) 1050g of ethyl acetate and 172.2g of acetic anhydride (1.69 mol) are sequentially added into a 3L three-necked flask, 150g (0.32 mol) of the mixture of the intermediate I and the intermediate II obtained in the step (1) is slowly added under stirring, the mixture is stirred at 20-25 ℃ for 30min, 26.3g of triethylamine (0.26 mol) is dropwise added under stirring, the temperature is controlled at 21-28 ℃ during the dropwise adding process, the mixture is stirred at 35-40 ℃ for 9h, and the sampling HPLC is used for central control: the peak area of the target product plus the peak area of the impurity is more than or equal to 98 percent.
(3) After the reaction is finished, the temperature is reduced to 5 to 9 ℃, 1190g of 15wt percent of Na is added dropwise 2 CO 3 The temperature of the aqueous solution is controlled to be less than 25 ℃ in the dropping process, stirring is continued for 1h after dropping, standing is carried out, layering is carried out, the upper organic layer is washed by 150g of purified water and then is transferred to a 3L three-mouth bottle, 45g of triethylamine (0.45 mol) is added under stirring, and stirring and heating are carried out until the temperature reaches 70-75 ℃ for reaction for 5h.
After the reaction is finished, cooling to 20-25 ℃, adding 220g of purified water, stirring for 30min, standing for layering, vacuum concentrating an upper organic layer to dryness at 45-90 ℃, dropwise adding 850g of toluene into the concentrated solution under stirring, controlling the temperature to 92-102 ℃ in the dropwise adding process, slowly cooling to 63-66 ℃ after dropwise adding, stirring for 2h at the temperature, precipitating a large amount of solid, continuously cooling to 3-8 ℃, filtering, leaching a filter cake with 150g of ice toluene, distilling to recover toluene, and vacuum drying a wet product at 80-85 ℃ for 16h to obtain 122.1g of a brown target product with the purity of 99.4% and the yield of 88.3% (calculated as a mixture of the intermediate I and the intermediate II in the step (2)).

Claims (8)

1. A method for synthesizing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane comprises the following steps:
(1) reacting 5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan with maleic anhydride in ethyl acetate to obtain a mixture of intermediate I and intermediate II;
(2) the mixture of the intermediate I and the intermediate II obtained in the step (1) is subjected to dehydration ring-closure reaction in ethyl acetate in the presence of an alkaline catalyst and acetic anhydride to obtain a reaction solution containing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan;
(3) and (3) carrying out impurity elimination treatment on the reaction liquid obtained in the step (2) by adopting an alkaline reagent, and then crystallizing by adopting toluene to obtain the N, N' -bis (maleimide group) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan.
2. The method for synthesizing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 1, wherein: in the step (3), the reaction temperature for removing impurities is 70-75 ℃.
3. The method for synthesizing N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 1 or 2, wherein: in the step (3), the alkaline reagent is triethylamine, pyridine, N-diisopropylethylamine or DMAP; the mol ratio of the mixture of the intermediate I and the intermediate II to the alkaline reagent is 1:0.5-1:4.
4. A method of synthesizing N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 3, wherein: the reaction temperature in the step (1) is 5-50 ℃.
5. A method of synthesizing N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 3, wherein: in the step (1), the molar ratio of the 5 (6) -amino-1- (4' -aminophenyl) -1, 3-trimethylindane to the maleic anhydride is 1:2-1:5.
6. A method of synthesizing N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 3, wherein: the dehydration ring-closure reaction temperature in the step (2) is 30-50 ℃.
7. A method of synthesizing N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 3, wherein: in the step (2), the molar ratio of the mixture of the intermediate I and the intermediate II to the acetic anhydride is 1:3-1:8.
8. A method of synthesizing N, N' -bis (maleimido) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindan according to claim 3, wherein: in the step (2), the basic catalyst is triethylamine, pyridine, N-diisopropylethylamine or DMAP; the mol ratio of the mixture of the intermediate I and the intermediate II to the basic catalyst is 1:0.2-1:3.
CN202310038822.8A 2023-01-12 2023-01-12 Synthesis method of N, N' -bis (maleimide) -5 (6) -amino-1- (4-aminophenyl) -1, 3-trimethylindane Pending CN116041242A (en)

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