CN101462997A - Preparation of N-phenyl maleimide - Google Patents
Preparation of N-phenyl maleimide Download PDFInfo
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- CN101462997A CN101462997A CNA2008102049341A CN200810204934A CN101462997A CN 101462997 A CN101462997 A CN 101462997A CN A2008102049341 A CNA2008102049341 A CN A2008102049341A CN 200810204934 A CN200810204934 A CN 200810204934A CN 101462997 A CN101462997 A CN 101462997A
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- aniline
- mixed
- solvent
- benzene
- phenylmaleimide
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- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 title claims description 24
- 238000002360 preparation method Methods 0.000 title claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 51
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 40
- 239000002904 solvent Substances 0.000 claims abstract description 24
- 238000000034 method Methods 0.000 claims abstract description 21
- 230000018044 dehydration Effects 0.000 claims abstract description 13
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- 239000000243 solution Substances 0.000 claims description 10
- 238000010992 reflux Methods 0.000 claims description 9
- 239000000047 product Substances 0.000 claims description 8
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 235000017550 sodium carbonate Nutrition 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 238000004140 cleaning Methods 0.000 claims description 4
- 229940045641 monobasic sodium phosphate Drugs 0.000 claims description 4
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 claims description 4
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 claims description 4
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 7
- 230000035484 reaction time Effects 0.000 abstract description 3
- 239000007810 chemical reaction solvent Substances 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000002699 waste material Substances 0.000 abstract description 2
- MKRBAPNEJMFMHU-UHFFFAOYSA-N 1-benzylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1CC1=CC=CC=C1 MKRBAPNEJMFMHU-UHFFFAOYSA-N 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 238000006358 imidation reaction Methods 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 238000012805 post-processing Methods 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 12
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005265 energy consumption Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 230000003373 anti-fouling effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Pyrrole Compounds (AREA)
Abstract
The invention discloses a method for preparing N-benzyl maleimide which adopts maleic anhydride and aniline as raw materials to take imidation reaction in benzene reaction solvent in the presence of an inhibitor and a mixed dehydration catalyst to obtain the target product of the invention. The purity of the N-benzyl maleimide prepared by the one-step method of the invention reaches more than 98.5 percent, and the yield is 90-92 percent. Compared with the prior art, the method has the advantages of less reaction time, short period and safe and convenient operation. A post-processing method of directly drying out the solvent and recycling the solvent is adopted, so that the yield is improved, three wastes are reduced, the operational environment is improved and the quality of products is stable. The method is applied to the large-scale industrial production.
Description
Technical field
The present invention relates to a kind of preparation method of N-phenylmaleimide.
Background technology
N-phenylmaleimide is a kind of important organism, can be widely used in antifouling paint and heat resistant plastice.As a kind of heat-proof modifier, N-phenylmaleimide also can partly substitute engineering plastics, adds in the ABS resin to make the excess of export heat-resisting ABS resin, makes the ABS resin heat resisting temperature reach 125～130 ℃.Its structural formula is as follows:
In the prior art, the preparation N-phenylmaleimide mainly carries out the synthetic method with maleic anhydride and aniline, and its reaction process is:
Shandong chemical industry 2000 29 volumes third phase 13-14 page or leaf " preparation research of N-phenylmaleimide " has reported that two step method prepares the method for N-phenylmaleimide, under 55-65 ℃ condition, maleic anhydride and aniline are reacted, through separating, obtain the acid of intermediate N phenyl maleimide, second step, acid of intermediate N phenyl maleimide and aceticanhydride, sodium-acetate reacts, obtain the finished product through dehydration, yield is 82.32%.This method adopts aceticanhydride as dewatering agent, and consumption is big, and aftertreatment produces a large amount of waste water, and expenses of environmental protection increases; The reaction process complex operation, yield is lower, and cost is higher, and industrial prospect is undesirable.
The method that 2003 15 volumes of modern plastics processed and applied, 04 phase 13-16 page or leaf " research of synthetic N-phenylmaleimide " report prepares N-phenylmaleimide is: adopt maleic anhydride and aniline in the presence of toluene and dimethyl formamide (DMF) solvent and stopper, prepare the acid of intermediate N phenyl maleimide, purify without separating, directly adding catalyzer tosic acid and copper sulfate in the acid of intermediate N phenyl maleimide dewaters, alkali cleaning, aftertreatment obtains product, yield 85%.In about 6 hours of this method reaction times, dewatering time needed more than 4 hours, and preparation cycle is long, and energy consumption is big, causes the cost height, is unfavorable for suitability for industrialized production.
Summary of the invention
The technical problem that the present invention solves provides a kind of preparation method of N-phenylmaleimide, and lower to overcome in the prior art yield, cost is higher, and preparation cycle is long, the shortcoming that energy consumption is big.
Technical conceive of the present invention is such: with maleic anhydride, aniline is raw material, in benzene class reaction solvent, carries out imidization reaction under the existence of stopper and mixed dehydration catalyzer, promptly obtains target product of the present invention.
Technical scheme of the present invention:
With stopper, the mixed dehydration catalyzer adds in the benzene kind solvent, be heated to backflow, 0.5-1.0 in hour, drip the mixed solution that 1. contains maleic anhydride, benzene kind solvent, DMF simultaneously, 2. aniline reflux dewatering 0.5-2.5 hour, is collected the target product N-phenylmaleimide then from reaction product.
According to the present invention, the mol ratio of said reaction raw materials aniline and maleic anhydride is 1:1.10-1.30, mol/mol, said stopper is 2, a kind of in 6-ditertbutylparacresol, Resorcinol, the pyrocatechol, the mass ratio of raw material aniline and stopper is 1:0.002-0.005, g/g.
The said mixed dehydration catalyzer of the present invention is a kind of the carrying out by mass ratio 1.0-5.0:1.0 in the vitriol oil and sodium pyrosulfate, SODIUM PHOSPHATE, MONOBASIC, the tosic acid, the g/g mixing obtains, the mass ratio of aniline and mixed dehydration catalyzer is 1:0.06-0.15, g/g.
The said benzene kind solvent of the present invention is one or more mixed preparing in the benzene,toluene,xylene, because the toxicity of benzene is big, benzene kind solvent selects one or more mixing in toluene, the dimethylbenzene to use, the quality of raw material aniline and the volume ratio of benzene kind solvent are 1:4-5, g/ml, the volume ratio of the quality of maleic anhydride and benzene kind solvent, DMF is 1:1.5-2.0:0.1-0.2, g/ml/ml.
The present invention collects target product and comprises the steps: that the organic phase of reaction product adds sodium carbonate solution under 50-60 ℃ condition from reaction product, remove benzene kind solvent after the alkali cleaning under reduced pressure, obtains yellow solid and is N-phenylmaleimide.
It is that the 8-15wt% sodium carbonate solution carries out alkali cleaning to the organic phase of reaction solution that the present invention adopts the quality percentage composition, and the mass ratio of raw material aniline and yellow soda ash is 1:0.15-0.18, g/g.
The used raw material of the present invention is the chemical of commercially available specification except that indicating.
Reaction formula of the present invention is as follows:
The N-phenylmaleimide purity that obtains with the preparation method of single stage method of the present invention reaches more than 98.5%, and productive rate is 90-92%.
The present invention compared with prior art, the reaction times reduces, the cycle shortens, simple and safe operation, adopt direct solvent evaporated, the post-treating method that solvent recuperation is utilized has improved output, has reduced the three wastes, operating environment improves, and constant product quality is suitable for large-scale industrial production.
Embodiment
The invention will be further described below by embodiment, but embodiment does not limit protection scope of the present invention.
Embodiment 1
In the reactor that has heating, thermometer, dropping funnel, reflux water-dividing prolong, add 100ml dimethylbenzene respectively, the 0.2g 2,6 ditertiary butyl p cresol, (mass ratio of the vitriol oil and sodium pyrosulfate is 1.0:1.0 to mixed dehydration catalyzer 4g, g/g).Stirring down, heat temperature raising extremely refluxes, 140 ℃ of temperature splashed into the mixed solution that 1. contains 58.8g (0.6mol) maleic anhydride-100ml dimethylbenzene-10ml DMF simultaneously by dropping funnel in 0.5 hour, 2. 46.5g (0.5mol) aniline, continue back flow reaction 1 hour, and divided water outlet 9ml.Reaction solution is cooled to 60 ℃, slowly adds 15wt% sodium carbonate solution 55ml, stirs 5 minutes, leaves standstill, tell organic phase, remove solvent under reduced pressure, reclaim solvent 174ml, obtain yellow solid product N-phenylmaleimide 77.9g, yield 90%, purity: 98.7% (HPLC).Fusing point: 88.6-90.1 ℃.
Embodiment 2
In the reactor that has heating, thermometer, dropping funnel, reflux water-dividing prolong, add 100ml toluene respectively, the 0.2g pyrocatechol, (mass ratio of the vitriol oil and SODIUM PHOSPHATE, MONOBASIC is 5.0:1.0 to mixed dehydration catalyzer 3g, g/g).Stirring down, heat temperature raising extremely refluxes, 110 ℃ of temperature splashed into the mixed solution that 1. contains 56.35g (0.575mol) maleic anhydride-100ml toluene-8ml DMF simultaneously by dropping funnel in 0.5 hour, 2. 46.5g (0.5mol) aniline, continue back flow reaction 2 hours, and divided water outlet 9ml.Reaction solution is cooled to 60 ℃, slowly adds 10wt% sodium carbonate solution 75ml, stirs 5 minutes, leaves standstill, tell organic phase, remove solvent under reduced pressure, reclaim solvent 162ml, obtain yellow solid product N-phenylmaleimide 79.2g, yield 91.5%, purity is 99.0% (HPLC).Fusing point: 89.2-90.1 ℃.
Embodiment 3
In the reactor that has heating, thermometer, dropping funnel, reflux water-dividing prolong, add 100ml toluene respectively, the 0.2g Resorcinol, (mass ratio of the vitriol oil and p-methyl benzenesulfonic acid is 1.5:1.0 to mixed dehydration catalyzer 5g, g/g).Stirring down, heat temperature raising extremely refluxes, temperature is 110 ℃, refluxes down to splash into the mixed solution that 1. contains 53.9g (0.55mol) maleic anhydride-100ml dimethylbenzene-7.5ml DMF by dropping funnel simultaneously in 1.0 hours, 2. 46.5g (0.5mol) aniline, continue back flow reaction 2.5 hours, and divided water outlet 9ml.Reaction solution is cooled to 50 ℃, slowly adds 8wt% sodium carbonate solution 100ml, stirs 5 minutes, leaves standstill, tell organic phase, remove solvent under reduced pressure, reclaim solvent 158ml, obtain yellow solid product N-phenylmaleimide 79.5g, yield 92%, purity: 98.9% (HPLC).Fusing point: 88.7-90.3 ℃.
Claims (10)
1. the preparation method of a N-phenylmaleimide, it is characterized in that comprising the steps: with stopper, the mixed dehydration catalyzer adds in the benzene kind solvent, be heated to backflow, 0.5-1.0 in hour, drip the mixed solution that 1. contains maleic anhydride, benzene kind solvent, DMF, 2. aniline simultaneously, reflux dewatering 0.5-2.5 hour, from reaction product, collect the target product N-phenylmaleimide then.
2. method according to claim 1 is characterized in that, said stopper is a kind of in 2,6 ditertiary butyl p cresol, Resorcinol, the pyrocatechol.
3. method according to claim 1 is characterized in that, said mixed dehydration catalyzer is a kind of mixed preparing in the vitriol oil and sodium pyrosulfate, SODIUM PHOSPHATE, MONOBASIC, the tosic acid.
4. method according to claim 1 is characterized in that, said benzene kind solvent is one or more mixed preparing in the benzene,toluene,xylene.
5. method according to claim 1, the mol ratio that it is characterized in that aniline and maleic anhydride is 1:1.10-1.30, mol/mol.
6. method according to claim 1, the mass ratio that it is characterized in that aniline and stopper is 1:0.002-0.005, g/g.
7. method according to claim 1, the mass ratio that it is characterized in that aniline and mixed dehydration catalyzer is 1:0.06-0.15, g/g, the mixed dehydration catalyzer is by a kind of mass ratio 1.0-5.0:1.0 that presses in the vitriol oil and p-methyl benzenesulfonic acid, sodium pyrosulfate, the SODIUM PHOSPHATE, MONOBASIC, g/g mixed preparing.
8. method according to claim 1 is characterized in that the quality of aniline and the volume ratio of benzene kind solvent are 1:4-5, g/ml, and the volume ratio of the quality of maleic anhydride and benzene kind solvent, DMF is 1:1.5-2.0:0.1-0.2, g/ml/ml.
9. method according to claim 1, it is characterized in that from reaction product, collecting target product and comprise the steps: that the organic phase of reaction product adds sodium carbonate solution under 50-60 ℃ condition, remove benzene kind solvent after the alkali cleaning under reduced pressure, obtain yellow solid and be N-phenylmaleimide.
10. according to claim 1 or 9 described methods, the mass ratio that it is characterized in that aniline and yellow soda ash is 1:0.15-0.18, g/g.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2008102049341A CN101462997A (en) | 2008-12-30 | 2008-12-30 | Preparation of N-phenyl maleimide |
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| CNA2008102049341A CN101462997A (en) | 2008-12-30 | 2008-12-30 | Preparation of N-phenyl maleimide |
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Cited By (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102382028A (en) * | 2011-08-26 | 2012-03-21 | 浙江工业大学 | Maleimide compound, its preparation and application |
| CN102399180A (en) * | 2011-12-02 | 2012-04-04 | 武汉工程大学 | Acidic ionic liquid catalyzed method for synthesizing N-phenylmaleimide |
| CN102850253A (en) * | 2012-08-15 | 2013-01-02 | 华烁科技股份有限公司 | Method for refining and molding N-phenylmaleimide |
| CN102909074A (en) * | 2012-10-24 | 2013-02-06 | 武汉新概念化工有限公司 | Immobilized type non-toxic catalyst and method for synthesizing N-phenylmaleimide and N-substitutional phenylmaleimide |
| CN103113279A (en) * | 2013-02-06 | 2013-05-22 | 浙江工业大学 | Maleimide type compound, as well as preparation and application thereof |
| CN103373949A (en) * | 2012-04-17 | 2013-10-30 | 日农科技股份有限公司 | The preparation method of N-phenylmaleimide |
| CN103664732A (en) * | 2013-12-26 | 2014-03-26 | 上海华谊（集团）公司 | Synthetic method of N-phenylmaleimide |
| 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 |
| CN104892484A (en) * | 2015-06-12 | 2015-09-09 | 云南大为恒远化工有限公司 | Synthesis method for N-phenylmaleimide |
| CN105503690A (en) * | 2014-09-23 | 2016-04-20 | 中国石油化工股份有限公司 | High-concentration N-phenylmaleimide reaction liquid post-treatment process |
| CN105503691A (en) * | 2014-09-23 | 2016-04-20 | 中国石油化工股份有限公司 | N-phenylmaleimide yield improving method |
| CN105859724A (en) * | 2016-04-29 | 2016-08-17 | 绍兴文理学院 | 3-(6-bromo-4-oxy-4H-chromone)-1-phenyl-5-p-chlorphenyl-1,6a-dihydro pyrroline[3,4-c] pyrazole-4,6(3aH,5H)-diketone and preparation method and application thereof |
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| CN105906633A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-phenyl maleimide derivative with chromone structure, and preparation method and application thereof |
| CN105906632A (en) * | 2016-04-29 | 2016-08-31 | 绍兴文理学院 | Pyrazole-type N-p-methylphenyl maleimide derivative with chromone structure, and preparation method and application thereof |
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- 2008-12-30 CN CNA2008102049341A patent/CN101462997A/en active Pending
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| CN102382028B (en) * | 2011-08-26 | 2014-11-12 | 浙江工业大学 | Maleimide compound, its preparation and application |
| CN102382028A (en) * | 2011-08-26 | 2012-03-21 | 浙江工业大学 | Maleimide compound, its preparation and application |
| CN102399180A (en) * | 2011-12-02 | 2012-04-04 | 武汉工程大学 | Acidic ionic liquid catalyzed method for synthesizing N-phenylmaleimide |
| CN103373949A (en) * | 2012-04-17 | 2013-10-30 | 日农科技股份有限公司 | The preparation method of N-phenylmaleimide |
| CN102850253A (en) * | 2012-08-15 | 2013-01-02 | 华烁科技股份有限公司 | Method for refining and molding N-phenylmaleimide |
| CN102850253B (en) * | 2012-08-15 | 2015-03-25 | 华烁科技股份有限公司 | Method for refining and molding N-phenylmaleimide |
| CN102909074A (en) * | 2012-10-24 | 2013-02-06 | 武汉新概念化工有限公司 | Immobilized type non-toxic catalyst and method for synthesizing N-phenylmaleimide and N-substitutional phenylmaleimide |
| CN102909074B (en) * | 2012-10-24 | 2014-04-16 | 武汉新概念化工有限公司 | Immobilized type non-toxic catalyst and method for synthesizing N-phenylmaleimide and N-substitutional phenylmaleimide |
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