CN102633706A - Synthesis method of N-phenyl-maleimide - Google Patents
Synthesis method of N-phenyl-maleimide Download PDFInfo
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- CN102633706A CN102633706A CN2011100837135A CN201110083713A CN102633706A CN 102633706 A CN102633706 A CN 102633706A CN 2011100837135 A CN2011100837135 A CN 2011100837135A CN 201110083713 A CN201110083713 A CN 201110083713A CN 102633706 A CN102633706 A CN 102633706A
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Abstract
The invention discloses a synthesis method of N-phenyl-maleimide, which comprises three steps of: 1. carrying out acylation on maleic anhydride and phenylamine in solvent to obtain N-phenyl-maleamic acid; 2. dehydrating the N-phenyl-maleamic acid in the solvent with hydroquinone and molecular sieve attached with phosphoric acid to obtain a crude product; and 3. adding activated clay and apply acid agent into the solvent of the crude product to obtain the product by refining. After the technology is adopted, the synthesis method is environment-friendly, simple in technology and low in cost.
Description
Technical field
The present invention relates to the compound method of N-phenylmaleimide, specifically is a kind of compound method that adopts acidylate to obtain N-phenylmaleimide.
Background technology
N-phenylmaleimide is the good a kind of heat-resisting organic monomer of development in recent years, and it is embedded in the polymer, can strengthen the inward turning resistance between the polymer, is mainly used in ABS, among the PVC etc.
At present N-phenylmaleimide produce main employing acidylate, but have complicated steps, shortcoming that product purity is low.
Summary of the invention
The invention provides a kind of compound method of N-phenylmaleimide, specifically is the compound method of a kind of dehydration catalyst and the N-phenylmaleimide that process for purification equipment is simple, process is simple, product purity is high.
In order to solve above technical problem, the compound method of a kind of N-phenylmaleimide of the present invention, mainly by cis-butenedioic anhydride and aniline in solvent, 20 ~ 50 ℃ of reactions 2 ~ 5 hours down, obtain the acid of N-phenyl maleimide; It is characterized in that: in the good system of above-mentioned reaction, add Resorcinol, with the molecular sieve of phosphoric acid, be warming up to 120 ~ 150 ℃, be dehydrated into ring, after 6 ~ 10 hours, be cooled to-5 ~ 0 ℃, suction filtration obtains the bullion N-phenylmaleimide; Bullion in refining solvent, is added carclazyte, acid-binding agent, and rising temperature for dissolving is extremely transparent, filtration, crystallisation by cooling, and drying obtains the product N-phenylmaleimide.
Further, the mol ratio of said cis-butenedioic anhydride and aniline is 1:1 ~ 1.4, and the weight ratio of cis-butenedioic anhydride and solvent is 1:6 ~ 10.
Further, the weight ratio of said Resorcinol and cis-butenedioic anhydride is 1:50 ~ 100, is 1:5 ~ 10 with the molecular sieve of phosphoric acid and the weight ratio of cis-butenedioic anhydride.
Further, the preparation method of said molecular sieve with phosphoric acid is: the 5A molecular sieve is immersed in the industrial phosphoric acid 24 hours, fully absorb phosphoric acid after, take out, in 120 ~ 150 ℃ dry 6 ~ 10 hours down.
Further, the weight ratio of said atlapulgite and bullion N-phenylmaleimide is 1:30 ~ 40, and the weight ratio of acid-binding agent and bullion N-phenylmaleimide is 1 ~ 20 ~ 25, and the weight ratio of bullion N-phenylmaleimide and solvent is: 1 ~ 3 ~ 5.
Further, said solvent comprises toluene, YLENE.
Further, said refining solvent comprises YLENE, hexanaphthene, 50% methanol solution.
Further, said acid-binding agent comprises sodium hydrogencarbonate, Sodium phosphate, dibasic.
The invention has the advantages that: this product and original acidylate compared with techniques, general procedure is all very similar, and difference is dehydration, process for purification.Adopt aforesaid method, process is simple, product purity is high.
Embodiment
Embodiment 1:
The 100Kg cis-butenedioic anhydride is dissolved in the 700Kg YLENE, be stirred to basic dissolving after, drip 100Kg aniline, the control rate of addition guarantees that temperature of reaction is no more than 35 ℃, after dropwising, continues to stir 1 hour, obtains the acidylate product.
Above-mentioned reaction system is transferred in another still, and the molecular sieve that adding 1.5Kg Resorcinol, 20Kg handle well through phosphoric acid dip is warming up to backflow, dehydration to anhydrous appearance.Be cooled to 60 ~ 70 ℃, while hot the molecular sieve suction filtration fallen, be cooled to about 0 ℃, keep 0 ℃ 2 ~ 3 hours, suction filtration obtains bullion.
Bullion, YLENE are dropped in the reaction kettle, and heating up is stirred to dissolving, adds carclazyte, sodium hydrogencarbonate, and bullion, YLENE, carclazyte, sodium hydrogencarbonate weight ratio drop into according to 1:5:0.05:0.05, after carclazyte, sodium hydrogencarbonate drop into; Stir after 1 hour, suction filtration, smart again filter is cooled to 0 ℃ with mother liquor; Keep more than 2 hours, suction filtration, after soaking with hexanaphthene, suction filtration again; Drying obtains product, and output is 158Kg, product purity 99.12%.
Example 2:
The 100Kg cis-butenedioic anhydride is dissolved in the 700Kg YLENE, be stirred to basic dissolving after, drip 100Kg aniline, the control rate of addition guarantees that temperature of reaction is no more than 35 ℃, after dropwising, continues to stir 1 hour, obtains the acidylate product.
Above-mentioned reaction system is transferred in another still, and the molecular sieve that adding 1.5Kg Resorcinol, 20Kg handle well through phosphoric acid dip is warming up to backflow, dehydration to anhydrous appearance.Be cooled to 60 ~ 70 ℃, while hot the molecular sieve suction filtration fallen, be cooled to about 0 ℃, keep 0 ℃ 2 ~ 3 hours, suction filtration obtains bullion.
Bullion, hexanaphthene are dropped in the reaction kettle, and heating up is stirred to dissolving, adds carclazyte, Sodium phosphate, dibasic, and bullion, YLENE, carclazyte, sodium hydrogencarbonate weight ratio drop into according to 1:7:0.05:0.05; After carclazyte, sodium hydrogencarbonate drop into, stir after 1 hour suction filtration, smart again filter; Mother liquor is cooled to 0 ℃, keeps more than 2 hours suction filtration, drying; Obtain product, output is 156Kg, product purity 99.18%.
Claims (8)
1. the compound method of a N-phenylmaleimide, mainly by cis-butenedioic anhydride and aniline in solvent, 20 ~ 50 ℃ of reactions 2 ~ 5 hours down, obtain the acid of N-phenyl maleimide; It is characterized in that: in the good system of above-mentioned reaction, add Resorcinol, with the molecular sieve of phosphoric acid, be warming up to 120 ~ 150 ℃, be dehydrated into ring, after 6 ~ 10 hours, be cooled to-5 ~ 0 ℃, suction filtration obtains the bullion N-phenylmaleimide; Bullion in refining solvent, is added carclazyte, acid-binding agent, be dissolved to transparently, filter, crystallisation by cooling, drying obtains the product N-phenylmaleimide.
2. the compound method of a kind of N-phenylmaleimide according to claim 1, it is characterized in that: the mol ratio of said cis-butenedioic anhydride and aniline is 1:1 ~ 1.4, the weight ratio of cis-butenedioic anhydride and solvent is 1:6 ~ 10.
3. the compound method of a kind of N-phenylmaleimide according to claim 1, it is characterized in that: the weight ratio of said Resorcinol and cis-butenedioic anhydride is 1:50 ~ 100, is 1:5 ~ 10 with the molecular sieve of phosphoric acid and the weight ratio of cis-butenedioic anhydride.
4. according to the compound method of claim 1 or 3 described a kind of N-phenylmaleimides; It is characterized in that: the preparation method of said molecular sieve with phosphoric acid is: the 5A molecular sieve is immersed in the industrial phosphoric acid 24 hours; After fully absorbing phosphoric acid; Take out, drying is 6 ~ 10 hours under 120 ~ 150 ℃.
5. the compound method of a kind of N-phenylmaleimide according to claim 1; It is characterized in that: the weight ratio of said atlapulgite and bullion N-phenylmaleimide is 1:30 ~ 40; The weight ratio of acid-binding agent and bullion N-phenylmaleimide is 1 ~ 20 ~ 25, and the weight ratio of bullion N-phenylmaleimide and solvent is: 1 ~ 3 ~ 5.
6. the compound method of a kind of N-phenylmaleimide according to claim 1, it is characterized in that: said solvent comprises toluene, YLENE.
7. the compound method of a kind of N-phenylmaleimide according to claim 1 is characterized in that: said refining solvent comprises YLENE, hexanaphthene, 50% methanol solution.
8. the compound method of a kind of N-phenylmaleimide according to claim 1, it is characterized in that: said acid-binding agent comprises sodium hydrogencarbonate, Sodium phosphate, dibasic.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100837135A CN102633706A (en) | 2011-04-02 | 2011-04-02 | Synthesis method of N-phenyl-maleimide |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011100837135A CN102633706A (en) | 2011-04-02 | 2011-04-02 | Synthesis method of N-phenyl-maleimide |
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| CN102633706A true CN102633706A (en) | 2012-08-15 |
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| CN2011100837135A Pending CN102633706A (en) | 2011-04-02 | 2011-04-02 | Synthesis method of N-phenyl-maleimide |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557657A (en) * | 2013-10-09 | 2015-04-29 | 中国石油化工股份有限公司 | One-step synthesis method of N-phenylmaleimide |
| CN106588743A (en) * | 2016-11-28 | 2017-04-26 | 蔚林新材料科技股份有限公司 | Method of preparing N-cyclohexylmaleimide with phosphoric acid and active white clay as composite catalyst and application thereof |
| CN115286558A (en) * | 2022-01-18 | 2022-11-04 | 聊城大学 | Maleimidocyclohexane compound and preparation method thereof |
-
2011
- 2011-04-02 CN CN2011100837135A patent/CN102633706A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104557657A (en) * | 2013-10-09 | 2015-04-29 | 中国石油化工股份有限公司 | One-step synthesis method of N-phenylmaleimide |
| CN106588743A (en) * | 2016-11-28 | 2017-04-26 | 蔚林新材料科技股份有限公司 | Method of preparing N-cyclohexylmaleimide with phosphoric acid and active white clay as composite catalyst and application thereof |
| CN106588743B (en) * | 2016-11-28 | 2019-09-27 | 蔚林新材料科技股份有限公司 | The method and its application of N- N-cyclohexylmaleimide are prepared using phosphoric acid and atlapulgite as composite catalyst |
| CN115286558A (en) * | 2022-01-18 | 2022-11-04 | 聊城大学 | Maleimidocyclohexane compound and preparation method thereof |
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Application publication date: 20120815 |