CN106188092B - The imido preparation method of N-2,6- diisopropyl aniline lists - Google Patents
The imido preparation method of N-2,6- diisopropyl aniline lists Download PDFInfo
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- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
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Abstract
The invention discloses a kind of 2,6 imido preparation methods of diisopropyl aniline list of N, including：（a）3,4,9,10 tetracarboxylic acid anhydrides, zinc acetate, water, 2,6 diisopropyl anilines are dissolved in imidazoles, is uniformly mixed, is reacted in microwave synthesizer, obtain reaction solution；（b）Reaction solution is cooled to room temperature, dichloromethane solution dissolving is added, filters insoluble matter, by filtrate liquid separation, organic phase hydrochloric acid, water, saturated nacl aqueous solution is taken to wash successively, silica gel post separation obtains target compound.The present invention is for the first time with specific material rate, reaction environment and reaction condition, high yield has synthesized fragrant amine-modified list imide compound-N 2,6 diisopropyl aniline list acid imides, realize that the reaction time is short, reaction temperature is low, the high three of products collection efficiency and excellent purpose simultaneously, and the separating-purifying of present invention compound obtained by the reaction is convenient, and preparation process is simple, and operation is easy, it, will be with boundless application prospect in dye industry suitable for industrialized production.
Description
Technical field
The present invention relates to the preparation process field of dyestuff, specifically a kind of N-2,6- diisopropyl aniline lists acyl Asia
The preparation method of amine.
Background technology
Single imide compound has the characteristics that excellent photo and thermal stability, high quantum production rate, is widely used in unimolecule
Fluorescent technique（T. D. M. Bell, A. Stefan, V. Lemaur, S. Bernhardt, K. Müllen, J.
Cornil, D. Beljonne, J. Hofkens, M. V. der Quweraer, F. C. D. Schryver.
Photochem.Photobiol. Sci., 2007, 6, 406-415.）, solar cell（M. Sekita, Á. J. Jim
énez, M. L. Marcos, E. Caballero, M. S. Rodríguez-Morgade, D. M. Guldi, T.
Torres. Chem. Eur. J., 2015, 21, 19028-19040；R. T. Cheriya, J. Joy, A. P.
Alex, A. Shaji, M. Hariharan. J. Phys. Chem. C, 2012, 116, 12489-12498.）And it is glimmering
Light probe molecule（L. Huang, S. W. Tam-Chang. Chem. Commun., 2011, 47, 2291-2293.）Deng
Field.And single imide compound is imide analog compounds of the synthesis near infrared absorption and fluorescence, such as
The necessary intermediate of terrylenebisimides, quaterrylenebisimides and pentarylenebisimides etc.
Molecule（T. Weil, T. Vosch, J. Hofkens, K. Peneva, K. Müllen. Angew. Chem. Int.
Ed., 2010, 49, 9068-9093；L. Chen, C. Li, K. Müllen. J. Mater. Chem. C., 2014,
2, 1938-1956.）.The product of single imide compound has been sold in German BASF dyestuff company at present, but I
State's list imide compound research is seldom.
Currently, the synthesis of external list imide compound mainly uses high-temperature high-pressure reaction kettle one-step synthesis or multistep to close
At.One-step synthesis method is typically to put into raw material by certain rate of charge, and in high-temperature high-pressure reaction kettle, reaction obtains high temperature for a long time
Target product.Multistep synthesis refers to that part material is carried out pre-reaction, is then placed in high-temperature high-pressure reaction kettle again, when high temperature is long
Between reaction obtain target product.The reaction temperature of one-step synthesis is up to 190 DEG C in both reactions, and the reaction time is small up to 23
When, yield is only between 20-51%（R. T. Cheriya, J. Joy, A. P. Alex, A. Shaji, M.
Hariharan.J. Phys. Chem. C., 2012, 116, 12489-12498；C. Li, H. Yan, G. F.
Zhang, W. L. Gong, T. Chen, R. Hu, M. P. Aldred,M. Q. Zhu.Chem. An Asian J.,
2014, 9, 104-109；H. Wei, N. Jiang, N. Zhao, Y. Zhang, B. Gao. Chinese J.
Chem., 2014, 32, 356-360.）.Compared with one-step synthesis, the yield of multistep synthesis it is opposite will more high point, but it is anti-
Total time is answered to need 25 hours, reaction temperature is up to 230 DEG C, and multistep is needed to purify product, purification step very complicated.
As it can be seen that there are reaction temperatures and pressure requirements that higher, reaction lasts for the synthetic method of single imide compound in the prior art
Many defects such as too long, yield is relatively low, production danger coefficient height, high energy consumption, complex steps complexity.Therefore, it further grinds
The preparation method for studying carefully more preferably single imide compound has important application value and social effect.
Invention content
It is an object of the invention to provide a kind of N-2, the imido preparation method of 6- diisopropyl aniline lists, to solve
In the prior art the synthetic method of single imide compound there are reaction temperatures and pressure requirements that higher, reaction lasts is too long,
Yield is relatively low, produces the problem of many defects such as danger coefficient height, high energy consumption, complex steps complexity.
The purpose of the present invention is what is be achieved through the following technical solutions：A kind of N-2,6- diisopropyl anilines list acid imide
Preparation method, include the following steps：
（a）3,4,9,10- tetracarboxylic acid anhydrides, zinc acetate, water, 2,6-DIPA are dissolved in imidazoles, mixing is equal
It is even, 20-60min is reacted at 160-180 DEG C, in setting power as 80 watts of microwave synthesizer, obtains reaction solution；Described 3,4,9,
10- tetracarboxylic acid anhydrides, zinc acetate, 2,6- diisopropyl anilines molar ratio be：1:1-4:5-10；The 3,4,9,10- tetra-
Formic anhydride, water, imidazoles mass volume ratio be 1g: 2-4 mL : 5.1-10.2g；
（b）The reaction solution is cooled to room temperature, dichloromethane solution dissolving is added, filters insoluble matter, by filtrate liquid separation,
Organic phase hydrochloric acid, water, saturated nacl aqueous solution is taken to wash successively, silica gel post separation obtains N-2,6- diisopropyl aniline lists
Acid imide.
Step in preparation method provided by the invention（a）Described in 3,4,9,10- tetracarboxylic acid anhydrides and 2,6- diisopropyls
The molar ratio of aniline is preferably 1: 7-8.
Step in preparation method provided by the invention（a）Described in 3,4,9,10- tetracarboxylic acid anhydrides and 2,6- diisopropyls
The molar ratio of aniline is more preferably 1: 7.
3,4,9,10- tetracarboxylic acid anhydrides in preparation method provided by the invention, water, imidazoles mass volume ratio be preferably 1g
: 3mL : 10.2g。
Step described in preparation method provided by the invention（a）In preferred reaction temperature be 170 DEG C, react 30min.
Most preferably, 3,4,9,10- tetracarboxylic acid anhydrides, zinc acetate, 2,6- described in preparation method provided by the invention
The molar ratio of diisopropyl aniline is：1:3:7；The 3,4,9,10- tetracarboxylic acid anhydrides, water, imidazoles mass volume ratio be 1g
: 3 mL :10.2g。
Step described in preparation method provided by the invention（b）Described in the eluant, eluent of silica gel post separation be volume ratio be 2:
1 dichloromethane and the mixture of petroleum ether.
Step described in preparation method provided by the invention（b）Middle addition dichloromethane solution dissolving, wherein the dichloro
The volume by volume concentration of dichloromethane is 50%, described 3, the quality volume of 4,9,10- tetracarboxylic acid anhydrides and the dichloromethane solution
Than for 1g:400mL.
Step described in preparation method provided by the invention（b）It is middle to be washed successively with hydrochloric acid, water, saturated nacl aqueous solution
The specific steps are by the 1.0mol/L hydrochloric acid solutions of 3,4,9,10- tetracarboxylic acid anhydrides 300mL described in 1g, with the distillation of 300mL
Water is washed successively with the saturated nacl aqueous solution of 300mL；It washed 2 times with the hydrochloric acid solution, be washed with distilled water 1 time, with full
It is washed 1 time with sodium chloride solution.
It is as follows using the imido chemical equation of preparation N-2,6- diisopropyl aniline lists provided by the invention：
。
The present invention with 3,4,9,10- tetracarboxylic acid anhydrides and 2,6-DIPA for main reaction raw materials, specific
Under material rate, reaction environment and microwave condition, high yield has synthesized fragrant amine-modified list imide compound --- N-2,
6- diisopropyl aniline list acid imides, this overcomes and is reacted in high-temperature high-pressure reaction kettle compared with existing preparation method
The shortcomings that temperature is high, the time is long and low yield, can make the reaction time of the prior art be reduced to 20-60 points from 23-25 hours
Clock improves about 46 times of efficiency, and reaction yield has been increased to highest 64% from the yield of the highest 51% of report, and reaction temperature is from 190-
230 DEG C are reduced to 160-170 DEG C.
The equivalent of raw material 3,4,9,10- tetracarboxylic acid anhydrides and zinc acetate, 2,6- bis- are different in preparation method provided by the invention
The equivalent of propyl aniline, the volume of water, the quality of imidazoles, reaction temperature and time there is important shadow to the yield of reaction
It rings, especially 3, the ingredient proportion of 4,9,10- tetracarboxylic acid anhydrides and 2,6-DIPA is most important.Therefore, of the invention
Innovative point be that for the first time with specific material rate, reaction environment and reaction condition, high yield has synthesized N-2,6- diisopropyls
Base aniline list acid imide, while the purpose that the reaction time is short, reaction temperature is low, products collection efficiency is high is realized, and the present invention
The separating-purifying of compound obtained by the reaction is convenient, and preparation process is simple, and operation is easy, and safety is good, is suitable for industrialized production,
It will be with boundless application prospect in dye industry.
Description of the drawings
Fig. 1 is the imido hydrogen nuclear magnetic resonance spectrogram of N-2,6- diisopropyl aniline lists prepared by the embodiment of the present invention 1.
Fig. 2 is the imido nuclear magnetic resonance of carbon spectrogram of N-2,6- diisopropyl aniline lists prepared by the embodiment of the present invention 1.
Specific implementation mode
Following example is for present invention be described in more detail, but the invention is not limited in any way.
Embodiment 1
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 17.85mmol
2,6-DIPA mixed dissolution in the imidazoles of 10.2g, be uniformly mixed, at a temperature of 170 DEG C, set power as
30min is reacted in 80 watts of microwave synthesizer, obtains reaction solution；Reaction solution is cooled to room temperature, the dichloromethane that 400mL is added is molten
Liquid（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L of 300mL successively
Hydrochloric acid solution washs 2 times, is washed 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, will be molten after washing
Liquid crosses silicagel column, and it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- bis- is different
Propyl aniline list acid imide.The yield for detecting its target compound is 64.1%.
Obtained compound N -2,6-DIPA list acid imide after testing, obtains proton nuclear magnetic resonance1HNMR
Data be： 1H NMR (600 MHz, CDCl3): δ1.18 (d, 12H, J = 6.6 Hz, -CH3), 2.78 (m,
2H, -CH), 7.35 (d, 2H, J = 7.8 Hz, Ar-H), 7.48 (t, 1H, J = 7.8 Hz, Ar-H),
7.62 (t, 2H, J = 7.8 Hz, Ar-H), 7.89 (d, 2H, J = 7.8 Hz, Ar-H), 8.41 (m, 4H,
Ar-H), 8.63 (d, 2H, J= 7.8 Hz, Ar-H).Its spectrogram is shown in Fig. 1；
Nuclear magnetic resonance of carbon13C NMR datas are：13C NMR (150 MHz, CDCl3): δ23.00 (-CH3), 28.17
(-CH), 119.11, 119.99, 122.74, 122.98, 125.98, 126.92, 128.15, 128.40,
129.49, 129.87, 130.11, 130.90, 133.25, 136.42, 144.73, 162.96.Its spectrogram is shown in Fig. 2.
Embodiment 2
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 2.55mmol, the water of 2mL, 20.4mmol
2,6-DIPA mixed dissolution is uniformly mixed in the imidazoles of 5.1g, at a temperature of 160 DEG C, sets power as 80
Watt microwave synthesizer in react 60min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.
Embodiment 3
By 1g（2.55 mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 10.2 mmol, the water of 4mL, 17.85
The 2,6-DIPA mixed dissolution of mmol is uniformly mixed in the imidazoles of 10.2g, at a temperature of 180 DEG C, setting work(
20min is reacted in the microwave synthesizer that rate is 80 watts, obtains reaction solution；Reaction solution is cooled to room temperature, the dichloromethane of 400mL is added
Alkane solution（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use 300mL's successively
1.0mol/L hydrochloric acid solutions wash 2 times, wash 1 time, will wash with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions
Solution after washing crosses silicagel column, and it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-
2,6- diisopropyl aniline list acid imides.
Embodiment 4
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 12.75mmol
2,6-DIPA mixed dissolution in the imidazoles of 10.2g, be uniformly mixed, at a temperature of 170 DEG C, set power as
30min is reacted in 80 watts of microwave synthesizer, obtains reaction solution；Reaction solution is cooled to room temperature, the dichloromethane that 400mL is added is molten
Liquid（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L of 300mL successively
Hydrochloric acid solution washs 2 times, is washed 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, will be molten after washing
Liquid crosses silicagel column, and it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- bis- is different
Propyl aniline list acid imide.The yield for detecting its target compound is 41.2%.
Embodiment 5
By 1g（2.55mol）The 2 of 3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 10.2mol, the water of 3mL, 25.5mol,
6- diisopropyl anilines mixed dissolution is uniformly mixed in the imidazoles of 5.1g, at a temperature of 170 DEG C, sets power as 80 watts
Microwave synthesizer in react 40min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.
Embodiment 6
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 15.3mmol
2,6-DIPA mixed dissolution is uniformly mixed in the imidazoles of 10.2g, at a temperature of 170 DEG C, sets power as 80
Watt microwave synthesizer in react 30min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.The yield for detecting its target compound is 46.4%.
Embodiment 7
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 20.4mmol
2,6-DIPA mixed dissolution is uniformly mixed in the imidazoles of 10.2g, at a temperature of 170 DEG C, sets power as 80
Watt microwave synthesizer in react 30min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.The yield for detecting its target compound is 56.3%.
Embodiment 8
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 25.5mmol
2,6-DIPA mixed dissolution is uniformly mixed in the imidazoles of 10.2g, at a temperature of 170 DEG C, sets power as 80
Watt microwave synthesizer in react 30min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.The yield for detecting its target compound is 53.1%.
Comparative example 1
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 2.55mmol
2,6-DIPA mixed dissolution is uniformly mixed in the imidazoles of 10.2g, at a temperature of 170 DEG C, sets power as 80
Watt microwave synthesizer in react 30min, obtain reaction solution；Reaction solution is cooled to room temperature, the dichloromethane solution of 400mL is added
（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L salt of 300mL successively
Acid solution wash 2 times washs 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, by the solution after washing
Silicagel column is crossed, it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- diisopropyls
Base aniline list acid imide.The yield for detecting its target compound is 18.0%.
Comparative example 2
By 1g（2.55mmol）3,4,9,10- tetracarboxylic acid anhydrides, the zinc acetate of 7.65mmol, the water of 3mL, 1.275mmol
2,6-DIPA mixed dissolution in the imidazoles of 10.2g, be uniformly mixed, at a temperature of 170 DEG C, set power as
30min is reacted in 80 watts of microwave synthesizer, obtains reaction solution；Reaction solution is cooled to room temperature, the dichloromethane that 400mL is added is molten
Liquid（VDichloromethane:VWater=1:1）Dissolving, filters insoluble matter, filtrate is carried out liquid separation, and organic phase is taken to use the 1.0mol/L of 300mL successively
Hydrochloric acid solution washs 2 times, is washed 1 time with the water washing 1 time of 300mL, with 300mL saturated nacl aqueous solutions, will be molten after washing
Liquid crosses silicagel column, and it is 2 that the eluant, eluent for crossing silicagel column, which is volume ratio,:1 dichloromethane and petroleum ether, separation, obtains N-2,6- bis- is different
Propyl aniline list acid imide.The yield for detecting its target compound is 13.0%.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by the embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications,
Equivalent substitute mode is should be, is included within the scope of the present invention.
Claims (3)
1. a kind of N- (2,6- diisopropyl phenyl) -- 3, the 4- imido preparation methods of dicarboxylic acids list, which is characterized in that packet
Include following steps：
（a）3,4,9,10- tetracarboxylic acid anhydrides, zinc acetate, water and 2,6-DIPA are dissolved in imidazoles, are uniformly mixed,
30min is reacted at 170 DEG C, in setting power as 80 watts of microwave synthesizer, obtains reaction solution；The 3,4,9,10- tetramethyls
Acid anhydrides, zinc acetate, 2,6- diisopropyl anilines molar ratio be：1:3:7-8；The 3,4,9,10- tetracarboxylic acid anhydrides, water, miaow
The mass volume ratio of azoles is 1g: 3mL : 10.2g ；
（b）The reaction solution is cooled to room temperature, dichloromethane solution dissolving is added, filters insoluble matter, filtrate liquid separation has taken
Machine is mutually washed with hydrochloric acid, water, saturated nacl aqueous solution successively, silica gel post separation, obtains N- (2,6- diisopropyl phenyl) -- and 3,
4- dicarboxylic acids list acid imides.
2. N- (2,6- diisopropyl phenyls) according to claim 1 -- the imido preparation side of 3,4- dicarboxylic acids lists
Method, which is characterized in that step（a）Described in 3,4,9,10- tetracarboxylic acid anhydrides and the molar ratio of 2,6- diisopropyl anilines be：1:
7。
3. N- (2,6- diisopropyl phenyls) according to claim 1 -- the imido preparation side of 3,4- dicarboxylic acids lists
Method, which is characterized in that the step（b）Described in the eluant, eluent of silica gel post separation be volume ratio be 2:1 dichloromethane and stone
The mixture of oily ether.
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