CN101250149A - Method for preparing 4,4-di(3-dimaleoyl imino-4-(4-cyano phenoxy) triphenylmethane - Google Patents
Method for preparing 4,4-di(3-dimaleoyl imino-4-(4-cyano phenoxy) triphenylmethane Download PDFInfo
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- CN101250149A CN101250149A CNA2008100354763A CN200810035476A CN101250149A CN 101250149 A CN101250149 A CN 101250149A CN A2008100354763 A CNA2008100354763 A CN A2008100354763A CN 200810035476 A CN200810035476 A CN 200810035476A CN 101250149 A CN101250149 A CN 101250149A
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Abstract
The invention discloses a preparation method of 4, 4'-bismaleimide-4''-(4-cyano phenoxy) triphenylmethane, which comprises (1) reacting 4, 4''-diamino-4''-(4-cyano phenoxy) triphenylmethane and maleic anhydride at the mol ratio of 1.0:2.0-2.2 in organic solvent system for 0.5-2h at room temperature to obtain 4, 4'-dicarboxylic butane amide-4''-(4-cyano phenoxy) triphenylmethane solution, (2) in the presence of azeotropic dehydrating agent or anhydride-tertiary amine catalyst, processing cyclodehydration on the carboxylic butane amide group of 4, 4'-dicarboxylic butane amide-4''-(4-cyano phenoxy) triphenylmethane for 2-18h, cooling, filtering, washing, filtering and drying to obtain 4, 4'-bismaleimide-4''-(4-cyano phenoxy) triphenylmethane. The invention has simple process and high yield, which is suitable for industrial production.
Description
Technical field
The present invention relates to the preparation method of organic compound, particularly relate to 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane.
Background technology
4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane is a kind of bismaleimide compound; contain imide structure in its molecular structure; have good thermostability; also contain undersaturated double bond structure; have quite active chemical reactivity; can play addition reaction with containing compound bearing active hydrogen (as oxy-compound, aminocompound, carboxylic compound etc.) or polymkeric substance, the compound or the polymkeric substance that also can contain unsaturated groups such as two keys or triple bond with other carry out chemical reaction.Therefore, 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane can be used for preparing the Thermocurable polyimide material of high heat resistance, also can be as the heat-proof modifier of Resins, epoxy, and make the epoxy-bismaleimide resin system of high heat resistance.
Can expect in advance, by 4,4 '-dimaleoyl imino-4 "-the high heat resistance Thermocurable polyimide material for preparing of (4-cyano-benzene oxygen) tritane, epoxy-bismaleimide resin system can further make the carbon fiber reinforced advanced composite material, can be used for the structured material of aerospacecraft (as aircraft, rocket, satellite, guided missile etc.) etc.; Also can further make glass fiber reinforced composite materials, can be used for the insulating material of printed circuit board, electrical equipment and electrical etc. etc.; The interlayer dielectic, FPC that also can make high-temperature-resistant structure tackiness agent, high-temperaure coating, electronics microelectronic device is with tackiness agent etc.
But, 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane.So far do not see as yet patent or disclosed bibliographical information are arranged.
Summary of the invention
The purpose of this invention is to provide a kind of 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane, this method technology is simple, environmental friendliness, purity and yield height, is applicable to industrial production.
Chemical equation of the present invention is as follows:
Of the present invention a kind of 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane, comprise the steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and maleic anhydride be in organic solvent system; reacted under the room temperature 0.5～2 hour, and obtained 4,4 '-dicarboxyl crotonoyl amido-4 "-(4-cyano-benzene oxygen) tritane solution;
(2) under the effect of azeotropy dehydrant or acid anhydrides-tertiary amine catalyst, with 4,4 '-dicarboxyl crotonoyl amido-4 "-reaction of the carboxylic crotonoyl amido cyclodehydration of (4-cyano-benzene oxygen) tritane is after 2～18 hours; cooling, filtration, washing, filtration, drying; obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane.
Organic solvent described in the step (1) is strong polar non-proton organic solvent, is N, dinethylformamide, N,N-dimethylacetamide, N-N-methyl-2-2-pyrrolidone N-, a kind of or its mixture in the dimethyl sulfoxide (DMSO).
The envelope-bulk to weight ratio of described organic solvent of step (1) and maleic anhydride is 5 milliliters～100 milliliters: 1 gram.
In the step (2) 4,4 '-dicarboxyl crotonoyl amido-4 "-the carboxylic crotonoyl amido cyclodehydration reaction of (4-cyano-benzene oxygen) tritane has two kinds of methods:
(1) azeotropic dehydration: 4,4 '-dicarboxyl crotonoyl amido-4 "-add azeotropy dehydrant in (4-cyano-benzene oxygen) tritane solution; stir; heat temperature raising, azeotropic dehydration cyclization be after 2～18 hours concentration of reaction solution; reclaim organic solvent with recycle; cooling, filtration, washing, filtration, drying, obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane;
(2) acid anhydrides evaporation: 4,4 '-dicarboxyl crotonoyl amido-4 "-add acid anhydrides, tertiary amine catalyst in (4-cyano-benzene oxygen) tritane solution; high-speed stirring; in 50 ℃～100 ℃ reactions after 2～18 hours down; cooling, filtration, acetone immersion, filtration, washing, filtration, drying; obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane.
The described azeotropy dehydrant of method (1) is a kind of or its blend in benzene,toluene,xylene, ethylbenzene, diethylbenzene, chlorobenzene, the dichlorobenzene.
The envelope-bulk to weight ratio of described azeotropy dehydrant of method (1) and maleic anhydride is 1 milliliter～50 milliliters: 1 gram.
The described acid anhydrides of method (2) is the lower aliphatic acid anhydrides, is a kind of or its mixture in diacetyl oxide, propionic anhydride, butyryl oxide, the valeric anhydride, and the ratio of lower aliphatic acid anhydrides and the mole number of maleic anhydride is 1.0～6.0: 1.0.
The described tertiary amine catalyst of method (2) is Trimethylamine 99, triethylamine, pyridine, picoline, tripropyl amine, Tributylamine, triamylamine, N, accelerine, N, N-dimethyl-p-toluidine, N, N-dimethyl Ortho Toluidine, N, a kind of or its mixture in the N-dimethyl meta-aminotoluene.
The described tertiary amine catalyst of method (2) is 0.01～0.10: 1.00 with the ratio of the mole number of maleic anhydride.
Beneficial effect of the present invention:
(1) the present invention is preparation 4,4 '-dimaleoyl imino-4 "-commercial run of (4-cyano-benzene oxygen) tritane, and product yield and purity are all higher;
(2) operating procedure of the present invention is simple, and the conversion unit less investment can be finished preparation process in same reactor;
(3) reaction process is to carry out under normal pressure, does not need high-tension apparatus;
(4) do not produce corrosives in reactant and the reaction process yet;
(5) after reaction is finished, reclaimed organic solvent, reusable edible.This has not only reduced cost, and has reduced environmental pollution;
(6) 4,4 '-diamino-4 "-reaction raw materials convenient sources such as (4-cyano-benzene oxygen) tritane and maleic anhydride, cost is lower, is convenient to further apply.
Description of drawings
Fig. 1 is 4,4 '-dimaleoyl imino-4 "-molecular structure of (4-cyano-benzene oxygen) tritane.
Embodiment
Below in conjunction with specific embodiment, further set forth the present invention.Should be understood that these embodiment only to be used to the present invention is described and be not used in and limit the scope of the invention.Should be understood that in addition those skilled in the art can make various changes or modifications the present invention after the content of having read the present invention's instruction, these equivalent form of values fall within the application's appended claims institute restricted portion equally.
Embodiment 1
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 1200 milliliters of N; the N-N,N-DIMETHYLACETAMIDE adds in the reactor, stirs under the room temperature, fully after the dissolving; add the maleic anhydride solid; make temperature of reaction maintain room temperature state, adds maleic anhydride solid 19.6 grams (0.2 mole) altogether in batches, stirs; after being homogeneous phase solution, continues stirring reaction 0.5 hour.Subsequently, add 250 milliliters of toluene, stir, heat temperature raising is kept reaction after 18 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N,N-dimethylacetamide drip washing filter cake 2～3 times, filters, and drying obtains 54.1 and restrains 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 98.2%.
Embodiment 2
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 2000 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor; stir under the room temperature; after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state; add maleic anhydride solid 21.6 grams (0.22 mole) altogether; stir, be homogeneous phase solution after, continued stirring reaction 1.5 hours.Subsequently, add 0.44 mole of acetic anhydride and 0.022 mole of triethylamine, high-speed stirring, heat temperature raising, after reacting 18 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, drying obtains 52.1 grams 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 94.6%.
Embodiment 3
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 800 milliliters of N; dinethylformamide adds in the reactor, stirs under the room temperature, fully after the dissolving; add the maleic anhydride solid; make temperature of reaction maintain room temperature state, adds maleic anhydride solid 21.6 grams (0.22 mole) altogether in batches, stirs; after being homogeneous phase solution, continues stirring reaction 2 hours.Subsequently, add 100 milliliters of dimethylbenzene, stir, heat temperature raising is kept reaction after 13 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and uses cold N, and dinethylformamide drip washing filter cake 2～3 times filters, and drying obtains 53.9 grams 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 97.8%.
Embodiment 4
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 1200 milliliters of dimethyl sulfoxide (DMSO) add in the reactor; stir under the room temperature; after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state; add maleic anhydride solid 19.6 grams (0.2 mole) altogether; stir, be homogeneous phase solution after, continued stirring reaction 2 hours.Subsequently, add 600 milliliters of toluene, stir, heat temperature raising is kept reaction after 15 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold dimethyl sulfoxide (DMSO) drip washing filter cake 2～3 times, filters, and drying obtains 52.7 and restrains 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 95.7%.
Embodiment 5
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane, 1200 milliliters of N-N-methyl-2-2-pyrrolidone N-s and 300 milliliters of N; the N-N,N-DIMETHYLACETAMIDE adds in the reactor, stirs under the room temperature, fully after the dissolving; add the maleic anhydride solid; make temperature of reaction maintain room temperature state, adds maleic anhydride solid 21.6 grams (0.22 mole) altogether in batches, stirs; after being homogeneous phase solution, continues stirring reaction 1.5 hours.Subsequently, add 200 milliliters of toluene and 200 milliliters of orthodichlorobenzenes, stir, heat temperature raising is kept reaction after 15 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N,N-dimethylacetamide drip washing filter cake 2～3 times, filters, and drying obtains 53.0 and restrains 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 96.2%.
Embodiment 6
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 900 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor; stir under the room temperature; after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state; add maleic anhydride solid 19.6 grams (0.2 mole) altogether; stir, be homogeneous phase solution after, continued stirring reaction 1 hour.Subsequently, add 1.2 mole of acetic anhydride and 0.02 mole of pyridine, high-speed stirring, heat temperature raising, after reacting 15 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, drying obtains 54.2 grams 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 98.2%.
Embodiment 7
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 850 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor; stir under the room temperature; after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state; add maleic anhydride solid 19.6 grams (0.2 mole) altogether; stir, be homogeneous phase solution after, continued stirring reaction 2 hours.Subsequently, add 120 milliliters of toluene, stir, heat temperature raising is kept reaction after 2 hours until reflux water-dividing, and concentration of reaction solution reclaims organic solvent, with Recycling.Stop heating, cooling reaction system filters, and with cold N-N-methyl-2-2-pyrrolidone N-drip washing filter cake 2～3 times, filters, and 120 ℃ of vacuum-drying 25 hours obtains 49.9 and restrains 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 90.5%.
Embodiment 8
With 39.1 gram (0.1 moles) 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and 2000 milliliters of N-N-methyl-2-2-pyrrolidone N-s add in the reactor; stir under the room temperature; after the dissolving, add the maleic anhydride solid fully in batches, make temperature of reaction maintain room temperature state; add maleic anhydride solid 21.6 grams (0.22 mole) altogether; stir, be homogeneous phase solution after, continued stirring reaction 1.5 hours.Subsequently, add 0.88 mole of acetic anhydride and 0.0022 mole of triethylamine, high-speed stirring, heat temperature raising, after reacting 2 hours under 50 ℃～100 ℃, cooling reaction system, filter, filter cake soaks with acetone, filters, and washes 2～3 times, filter, 120 ℃ of vacuum-drying 25 hours obtains 46.1 grams 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane solid product.According to 4,4 '-diamino-4 "-charging capacity, 4 of (4-cyano-benzene oxygen) tritane; 4 '-dimaleoyl imino-4 "-theoretical yield (55.1 gram) and the actual output of (4-cyano-benzene oxygen) tritane, calculate 4,4 '-dimaleoyl imino-4 "-yield of (4-cyano-benzene oxygen) tritane is 83.7%.
Claims (7)
1.4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane, comprise the steps:
(1) mol ratio be 1.0: 2.0～2.2 4,4 '-diamino-4 "-(4-cyano-benzene oxygen) tritane and maleic anhydride be in organic solvent system; reacted under the room temperature 0.5～2 hour, and obtained 4,4 '-dicarboxyl crotonoyl amido-4 "-(4-cyano-benzene oxygen) tritane solution;
(2) under the effect of azeotropy dehydrant or acid anhydrides-tertiary amine catalyst, with 4,4 '-dicarboxyl crotonoyl amido-4 "-reaction of the carboxylic crotonoyl amido cyclodehydration of (4-cyano-benzene oxygen) tritane is after 2～18 hours; cooling, filtration, washing, filtration, drying; obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane.
2. according to claim 14,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane; it is characterized in that: the organic solvent described in the step (1) is strong polar non-proton organic solvent; be N; dinethylformamide, N,N-dimethylacetamide; the N-N-methyl-2-2-pyrrolidone N-, a kind of or its mixture in the dimethyl sulfoxide (DMSO).
3. according to claim 1 and 24,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane, it is characterized in that: the envelope-bulk to weight ratio of described organic solvent of step (1) and maleic anhydride is 5 milliliters～100 milliliters: 1 gram.
4. according to claim 14,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane; it is characterized in that: in the step (2) 4,4 '-dicarboxyl crotonoyl amido-4 "-the carboxylic crotonoyl amido cyclodehydration reaction of (4-cyano-benzene oxygen) tritane has two kinds of methods:
(1) azeotropic dehydration: 4,4 '-dicarboxyl crotonoyl amido-4 "-add azeotropy dehydrant in (4-cyano-benzene oxygen) tritane solution; stir; heat temperature raising, azeotropic dehydration cyclization be after 2～18 hours concentration of reaction solution; reclaim organic solvent with recycle; cooling, filtration, washing, filtration, drying, obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane;
(2) acid anhydrides evaporation: 4,4 '-dicarboxyl crotonoyl amido-4 "-add acid anhydrides, tertiary amine catalyst in (4-cyano-benzene oxygen) tritane solution; high-speed stirring; in 50 ℃～100 ℃ reactions after 2～18 hours down; cooling, filtration, acetone immersion, filtration, washing, filtration, drying; obtain 4,4 '-dimaleoyl imino-4 "-(4-cyano-benzene oxygen) tritane.
5. according to claim 1 or 4 described 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane; it is characterized in that: the described azeotropy dehydrant of method (1) is a kind of or its blend in benzene,toluene,xylene, ethylbenzene, diethylbenzene, chlorobenzene, the dichlorobenzene, and the envelope-bulk to weight ratio of azeotropy dehydrant and maleic anhydride is 1 milliliter～50 milliliters: 1 gram.
6. according to claim 1 or 4 described 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane; it is characterized in that: the described acid anhydrides of method (2) is the lower aliphatic acid anhydrides; be a kind of or its mixture in diacetyl oxide, propionic anhydride, butyryl oxide, the valeric anhydride, and the ratio of lower aliphatic acid anhydrides and the mole number of maleic anhydride is 1.0～6.0: 1.0.
7. according to claim 1 or 4 described 4,4 '-dimaleoyl imino-4 "-preparation method of (4-cyano-benzene oxygen) tritane; it is characterized in that: the described tertiary amine catalyst of method (2) is Trimethylamine 99, triethylamine, pyridine, picoline, tripropyl amine, Tributylamine, triamylamine, N; accelerine, N; N-dimethyl-p-toluidine, N; N-dimethyl Ortho Toluidine, N; a kind of or its mixture in the N-dimethyl meta-aminotoluene, and the ratio of tertiary amine catalyst and the mole number of maleic anhydride is 0.01～0.10: 1.00.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329195A (en) * | 2011-07-07 | 2012-01-25 | 辽宁石油化工大学 | Improvement on method for synthesizing tert-butylcalix[4]arene |
| TWI406859B (en) * | 2008-12-25 | 2013-09-01 | Ind Tech Res Inst | Pentaphenyldiamine-containing bismaleimide compound and producing method thereof |
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2008
- 2008-04-02 CN CNA2008100354763A patent/CN101250149A/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI406859B (en) * | 2008-12-25 | 2013-09-01 | Ind Tech Res Inst | Pentaphenyldiamine-containing bismaleimide compound and producing method thereof |
| CN102329195A (en) * | 2011-07-07 | 2012-01-25 | 辽宁石油化工大学 | Improvement on method for synthesizing tert-butylcalix[4]arene |
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