CN111320571A - Novel method for preparing 4-dimethylaminopyridine - Google Patents
Novel method for preparing 4-dimethylaminopyridine Download PDFInfo
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Abstract
The invention discloses a new method for preparing 4-dimethylaminopyridine, which comprises the steps of putting an acrylic acid raw material into a reaction kettle, putting a concentrated hydrochloric acid raw material into the reaction kettle, putting hydroquinone into the reaction kettle, heating and stirring the mixture, and stirring the mixture at the temperature of between 80 and 100 ℃ for reaction for 2 to 4 hours; slowly adding 4-cyanopyridine raw material at the temperature of 80-100 ℃, wherein the feeding time is 1-2 hours, continuously reacting for 1-2 hours after the feeding is finished, and carrying out reduced pressure distillation to recover excessive hydrochloric acid. In the present invention, acrylic acid is sufficiently activated to undergo a sufficient radical protecting reaction with 4-cyanopyridine. Meanwhile, hydroquinone is added as a polymerization inhibitor of acrylic acid, so that other side reactions are not generated at high temperature.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a novel method for preparing 4-dimethylaminopyridine.
Background
4-dimethylamino pyridine is a white crystal powder with molecular formula C, which is a novel high-efficiency catalyst widely used in chemical synthesis7H10N2. The molecular structure is as follows:
4-Dimethylaminopyridine (DMAP) with CAS registry number 1122-58-3.
4-dimethylamino pyridine is a novel high-efficiency catalyst widely used for chemical synthesis in recent years, the resonance of dimethylamino group for supplying electrons on the structure and a mother ring (pyridine ring) can strongly activate nitrogen atoms on the ring for nucleophilic substitution, and the acylation (phosphorylation, sulfonylation and carbon acylation) reaction of alcohol and amine with high steric hindrance and low reactivity is remarkably catalyzed, and the activity of the catalyst is about 10 of pyridine4-6And (4) doubling. The catalyst has high catalytic capability in various reactions such as acylation, alkylation, etherification, esterification and ester exchange in organic synthesis, pharmaceutical synthesis, pesticides, medicines, dyes, perfumes, polymer chemistry and analytical chemistry, has extremely obvious effect on improving yield, and can also be used as a phase transfer catalyst for interface reaction. Its advantages are: the catalyst is small in dosage, and generally only needs 0.01-5% of the mole number of a reaction substrate, and acid generated by the reaction can be neutralized by organic base or inorganic base; the reaction condition is mild, the reaction can be carried out at room temperature, and the energy is saved; the solvent has wide selection range and can be carried out in polar and non-polar organic solvents; the reaction time is short, pyridine is used for reacting for a long time, and DMAP is used for completing the reaction within minutes, so that the labor productivity is greatly improved; the yield is high, for example, when pyridine is used for hardly reacting hydroxyl compounds with large steric hindrance, the yield of DMAP can reach 80-90%, so that the reaction yield and the product quality can be improved, and the process can be simplified; less side reaction, less smell and less three wastes; DMAP has become one of the most commonly used catalysts for organic synthesizers due to its superior catalytic properties, known as a "super catalyst".
Many methods for synthesizing DMAP have been reported, including the 4-pyridone method, the 4-chloropyridine method, the 4-hydroxypyridine method, the 4-pyridinesulfonic acid method, and the 4-trimethylsilylpyridine method. However, the DMAP synthesis method in industry mainly uses pyridine and SOCl2The intermediate product N- (4-pyridyl) pyridine chloride hydrochloride (namely bipyridyl salt) is prepared by reaction as a raw material, and then the intermediate product N- (4-pyridyl) pyridine chloride hydrochloride and DMF are refluxed to prepare DMAP. The method has the advantages of cheap and easily obtained raw materials, simple and convenient operation and short process flow, but the conversion rate of the raw material pyridine is low, and is generally below 40%. Meanwhile, the dosage of thionyl chloride is large, the discharge amount of three wastes is large, the treatment is difficult, and the pollution to the environment is very serious. Is provided withThe reports that DMAP is prepared by taking 4-cyanopyridine as a raw material and dimethylamine aqueous solution as an amination reagent under the activation of 2-vinylpyridine have relatively mild reaction conditions and greatly improved reaction yield. However, the 2-vinylpyridine used in the method is high in price, and the recycling effect is not ideal, so that the industrial application is hindered.
Disclosure of Invention
The invention mainly solves the defects in the prior art and provides a novel method for preparing 4-dimethylaminopyridine.
The invention is realized by the following technical scheme for achieving the aim:
the invention discloses a novel method for preparing 4-dimethylaminopyridine, which comprises the following steps:
(1) adding an acrylic acid raw material, a concentrated hydrochloric acid raw material and hydroquinone into a reaction kettle, heating and stirring, and stirring and reacting at the temperature of 80-100 ℃ for 2-4 hours;
(2) slowly adding 4-cyanopyridine raw material at the temperature of 80-100 ℃, wherein the feeding time is 1-2 hours, continuously reacting for 1-2 hours after the feeding is finished, and recovering excessive hydrochloric acid by reduced pressure distillation;
(3) slowly dripping the obtained reaction solution into 40 percent dimethylamine aqueous solution under the condition of keeping the temperature at 80-100 ℃, controlling the reaction temperature to reflux at 50 ℃, controlling the dripping time to be 1-2 hours, and then keeping the temperature for 1-2 hours for reaction;
(4) slowly dripping liquid alkali raw materials at the temperature of 50-70 ℃, simultaneously carrying out reduced pressure distillation to recover excessive dimethylamine, wherein the dripping time is 1-2 hours, after the dripping is finished, heating, and controlling a reaction system to continuously react for 1-2 hours at the temperature of 80-100 ℃ to finish the reaction;
(5) after the reaction is finished, transferring the reaction solution into an extraction kettle while the reaction solution is hot, and adding toluene or xylene for extraction, wherein the extraction temperature is 80-100 ℃;
(6) adding the organic phase obtained by extraction into active carbon for decoloring and filtering, and cooling to separate out white crystals, namely the product 4-dimethylaminopyridine;
(7) adding hydrochloric acid into the raffinate phase obtained by extraction to adjust the pH value to 5-7, adding the next batch of raw material 4-cyanopyridine at the temperature of 90-100 ℃ for extraction and recovery, directly putting the organic phase after extraction into the next batch of reaction kettle, and beginning the next batch of reaction after supplementing part of raw materials.
As a further improvement, the liquid caustic soda raw material is sodium hydroxide.
As a further improvement, the molar ratio of the raw materials in the method is 4-cyanopyridine: acrylic acid: hydrogen chloride (hydrochloric acid): hydroquinone: dimethylamine: sodium hydroxide ═ 1.0: 1.1-1.3: 2.2-3.3: 0.0055-0.0065: 2.0-4.0: 4.0-6.0.
As a further improvement, the recovery rate of acrylic acid in the method of the invention is more than 93%, the yield of 4-dimethylaminopyridine calculated by 4-cyanopyridine is more than 97%, and the content of 4-dimethylaminopyridine is more than 99.0%.
The invention has the following beneficial effects:
1. according to the reaction mechanism and the reaction kinetics principle, the acrylic acid raw material and the cheap hydrochloric acid raw material are firstly reacted, so that the reaction probability of the acrylic acid is reduced after the hydrochloric acid is directly salified with the 4-cyanopyridine. In the present invention, acrylic acid is sufficiently activated to undergo a sufficient radical protecting reaction with 4-cyanopyridine. Meanwhile, hydroquinone is added as a polymerization inhibitor of acrylic acid, so that other side reactions are not generated at high temperature.
2. After acrylic acid is fully activated, the 4-cyanopyridine raw material is slowly added into the reaction system, so that the 4-cyanopyridine raw material can be further ensured to be fully reacted with the acrylic acid, and the product selectivity and the product yield are improved. The excessive hydrochloric acid is beneficial to the combination of the hydrochloric acid and the waste water, and after the reaction is finished, the excessive hydrochloric acid is recovered, so that the water content in the system can be reduced, and the total amount of salts in the three wastes can be reduced.
3. The present invention further comprises slowly dropping the reaction solution into the dimethylamine aqueous solution to carry out the substitution reaction while keeping the temperature of the reaction solution at a high temperature. The high temperature state ensures the fluidity and low viscosity of the reaction liquid, thereby being beneficial to mass transfer and reaction, and the high excess proportion of dimethylamine further ensures the complete proceeding of the substitution reaction.
4. After the substitution reaction is finished, adding liquid alkali and recovering dimethylamine, so that the consumption of the raw material dimethylamine can be reduced, the cost is reduced, and the system can be rapidly heated, thereby completing the hydrolysis reaction.
5. The invention adopts a hot extraction mode to directly extract and take out a high-purity product, decolors and crystallizes the product while the product is hot to obtain a high-purity product DMAP, thereby greatly saving energy. In the raffinate phase obtained after the thermal extraction, the method directly adds acid for neutralization, and adopts the next batch of raw material 4-cyanopyridine for thermal extraction, thereby not only recovering the acrylic acid in the raffinate phase, but also recovering part of unreacted raw materials, greatly reducing COD in the wastewater, reducing the treatment difficulty, greatly improving the recovery rate of the acrylic acid in the process, improving the yield of the product and reducing the comprehensive cost.
6. In the reaction, due to the comprehensive utilization of the process, the recovery rate of acrylic acid in the process is more than 93%, the yield of 4-dimethylaminopyridine calculated by 4-cyanopyridine is more than 97%, and the content of 4-dimethylaminopyridine is more than 99.0%.
Detailed Description
The technical solution of the present invention will be further described in detail with reference to specific examples, but the scope of the present invention is not limited to the examples.
Example 1
(1) 1.1mol of acrylic acid raw material, 2.2mol of concentrated hydrochloric acid raw material (hydrogen chloride mol number is 2.2mol), 0.0055mol of polymerization inhibitor hydroquinone are added into the reaction kettle, and the mixture is heated and stirred. The reaction was stirred at a temperature of 80 ℃ for 4 hours.
(2) Slowly adding 1.0mol of 4-cyanopyridine raw material at the temperature of 80 ℃, wherein the adding time is 2 hours, and continuing the reaction for 2 hours after the adding is finished. And (5) distilling under reduced pressure to recover excessive hydrochloric acid.
(3) The obtained reaction solution was slowly dropped into a 40% dimethylamine aqueous solution (molar number of dimethylamine: 2.0mol) while keeping the temperature at 80 ℃, the reaction temperature was controlled to 50 ℃ for reflux, the dropping time was controlled to 1 hour, and then the reaction was carried out by keeping the temperature for 1 hour.
(4) At a temperature of 50 ℃, slowly dripping liquid alkali raw materials (the mass concentration is 30 percent, the mole number of sodium hydroxide is 4.0mol), simultaneously decompressing, distilling and recovering excessive dimethylamine, and the dripping time is 2 hours. After the dropwise addition, the temperature is raised, and the reaction system is controlled to continue to react at 80 ℃ for 2 hours, so that the reaction is finished.
(5) After the reaction is finished, the reaction solution is transferred into an extraction kettle while the reaction solution is hot. Toluene was added for extraction. The extraction temperature was 80 ℃.
(6) Adding the organic phase obtained by extraction into active carbon for decolorization and filtration, and cooling to separate out white crystals, namely the product 4-dimethylaminopyridine.
(7) Adding hydrochloric acid into the raffinate phase obtained by extraction to adjust the pH value to 5, adding 1.0mol of the next batch of raw material 4-cyanopyridine at the temperature of 90 ℃ for extraction and recovery, directly putting the organic phase after extraction into the next batch of reaction kettle, and starting the next batch of reaction.
The white solid product 4-dimethylamino pyridine can be obtained through the reaction. The recovery rate of acrylic acid in the process is calculated to be 93%, the yield of 4-dimethylamino pyridine calculated by 4-cyanopyridine is 97%, and the content of 4-dimethylamino pyridine is 99.2%.
Example 2
(1) 1.3mol of acrylic acid raw material, 3.3mol of concentrated hydrochloric acid raw material (the mole number of hydrogen chloride is 3.3mol), 0.0065mol of polymerization inhibitor hydroquinone are added into a reaction kettle, and the mixture is heated and stirred. The reaction was stirred at a temperature of 100 ℃ for 2 hours.
(2) Slowly adding 1.0mol of 4-cyanopyridine raw material at the temperature of 100 ℃, wherein the adding time is 1 hour, and continuing the reaction for 1 hour after the adding is finished. And (5) distilling under reduced pressure to recover excessive hydrochloric acid.
(3) The obtained reaction solution was slowly dropped into a 40% dimethylamine aqueous solution (mole number of dimethylamine: 4.0mol) while keeping the temperature at 100 ℃, the reaction temperature was controlled at 50 ℃ for reflux, the dropping time was controlled at 2 hours, and then the reaction was carried out by keeping the temperature for 2 hours.
(4) At a temperature of 70 ℃, slowly dropping liquid alkali raw materials (mass concentration is 50 percent, and the mole number of sodium hydroxide is 6.0mol), simultaneously decompressing, distilling and recovering excessive dimethylamine, wherein the dropping time is 1 hour. After the dropwise addition, the temperature is raised, and the reaction system is controlled to continue to react at 100 ℃ for 1 hour, so that the reaction is finished.
(5) After the reaction is finished, the reaction solution is transferred into an extraction kettle while the reaction solution is hot. Adding dimethylbenzene for extraction. The extraction temperature was 100 ℃.
(6) Adding the organic phase obtained by extraction into active carbon for decolorization and filtration, and cooling to separate out white crystals, namely the product 4-dimethylaminopyridine.
(7) Adding hydrochloric acid into the raffinate phase obtained by extraction to adjust the pH value to 7, adding 1.0mol of the next batch of raw material 4-cyanopyridine at the temperature of 100 ℃ for extraction and recovery, directly putting the organic phase after extraction into the next batch of reaction kettle, and starting the next batch of reaction.
The white solid product 4-dimethylamino pyridine can be obtained through the reaction. The recovery rate of acrylic acid in the process is calculated to be 94%, the yield of 4-dimethylamino pyridine calculated by 4-cyanopyridine is 98%, and the content of 4-dimethylamino pyridine is 99.5%.
Example 3
(1) 1.2mol of acrylic acid raw material, 2.5mol of concentrated hydrochloric acid raw material (hydrogen chloride mol number is 2.5mol), 0.006mol of polymerization inhibitor hydroquinone are added into a reaction kettle, and the mixture is heated and stirred. The reaction was stirred at a temperature of 90 ℃ for 3 hours.
(2) At the temperature of 90 ℃, 1.0mol of 4-cyanopyridine raw material is slowly added for 1.5 hours, and after the addition is finished, the reaction is continued for 1.5 hours. And (5) distilling under reduced pressure to recover excessive hydrochloric acid.
(3) The obtained reaction solution was slowly dropped into a 40% dimethylamine aqueous solution (molar amount of dimethylamine: 3.0mol) while keeping the temperature at 90 ℃ and the reaction temperature was controlled to 50 ℃ for reflux, and the dropping time was controlled to 1.5 hours, after which the reaction was carried out with keeping the temperature for 1.5 hours.
(4) At a temperature of 60 ℃, slowly dropwise adding a liquid alkali raw material (the mass concentration is 40 percent, and the mole number of sodium hydroxide is 5.0mol), simultaneously carrying out reduced pressure distillation to recover excessive dimethylamine, wherein the dropwise adding time is 1.5 hours. After the dropwise addition, the temperature was raised, and the reaction was terminated after the reaction system was controlled to continue the reaction at 90 ℃ for 1.5 hours.
(5) After the reaction is finished, the reaction solution is transferred into an extraction kettle while the reaction solution is hot. Toluene was added for extraction. The extraction temperature was 90 ℃.
(6) Adding the organic phase obtained by extraction into active carbon for decolorization and filtration, and cooling to separate out white crystals, namely the product 4-dimethylaminopyridine.
(7) Adding hydrochloric acid into the raffinate phase obtained by extraction to adjust the pH value to 6, adding 1.0mol of the next batch of raw material 4-cyanopyridine at the temperature of 95 ℃ for extraction and recovery, directly putting the organic phase after extraction into the next batch of reaction kettle, and starting the next batch of reaction.
The white solid product 4-dimethylamino pyridine can be obtained through the reaction. The recovery rate of acrylic acid in the process is calculated to be 95%, the yield of 4-dimethylamino pyridine calculated by 4-cyanopyridine is 98.6%, and the content of 4-dimethylamino pyridine is 99.6%.
Comparative example 4
31.5g (0.303mol) of 4-cyanopyridine, 25mL of water, 44g (37mL) of concentrated hydrochloric acid, and 21g (0.200mol) of 2-vinylpyridine were successively charged into a stirred tank reactor, and mixed at 60 ℃ for 6 hours. After cooling to 30 ℃, 36.5mLw (dimethylamine) ═ 32% dimethylamine aqueous solution was added dropwise, and the mixture was stirred vigorously at 30 ℃ for 2 hours. Adding 200ml (NaOH) 40% liquid alkali, heating and boiling under reflux for 2 h. After the solution was cooled, an oil layer was separated, dried over anhydrous sodium sulfate, and distilled under reduced pressure, and the first collected fraction was 15.0g of 2-vinylpyridine (recovery rate: 71.4%). And (3) continuing reduced pressure distillation, cooling the collected fraction to obtain a light yellow solid, recrystallizing with ethyl acetate, and decoloring with activated carbon to obtain a white crystal DMAP27.3g, wherein the yield is 74.0%, and the test content is 99.0%.
Comparative example 5
200g of 4-cyanopyridine, 107g of acrylic acid and 170g of water are sequentially added into a stirred tank reactor and stirred uniformly. 260g of concentrated hydrochloric acid was further added dropwise thereto, and the mixture was kept at 55 ℃ for 4 hours. After cooling to room temperature, 420g of dimethylamine in water (33% by weight) were added in one portion and the mixture was incubated at 40 ℃ for 1.5 hours. After the heat preservation is finished, liquid caustic soda with the weight concentration of 30% is dripped until the pH value is 12, and the heat preservation is carried out for 1.5 hours under the reflux condition. And after the system is cooled, removing the water layer by suction filtration, washing with solid phase water, and drying to obtain a finished product of the 4-dimethylaminopyridine. The content of the product is 96.5 percent by detection, and the yield is 70 percent. Adjusting the pH value of the water layer after suction filtration to 5 by adopting hydrochloric acid, adding toluene for extraction, and testing the recovery rate of acrylic acid to be 31 percent after desolventizing.
Comparative example 6
200g of 4-cyanopyridine and 107g of acrylic acid are sequentially added into a stirring tank type reactor, hydrogen chloride gas is introduced into the reaction tank through a vent pipe under the stirring of 55 ℃, the vent pipe is blocked within half an hour, the reaction cannot be continued, and the reaction is stopped.
Finally, it should also be noted that the above list is only a specific implementation example of the present invention. It is obvious that the invention is not limited to the above embodiment examples, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (4)
1. A novel method for preparing 4-dimethylaminopyridine is characterized by comprising the following steps:
1) adding acrylic acid raw material, concentrated hydrochloric acid raw material and hydroquinone into a reaction kettle, heating and stirring, and stirring and reacting at the temperature of 80-100 ℃ for 2-4 hours;
2) slowly adding a 4-cyanopyridine raw material at the temperature of 80-100 ℃, wherein the feeding time is 1-2 hours, continuously reacting for 1-2 hours after the feeding is finished, and recovering excessive hydrochloric acid by reduced pressure distillation;
3) slowly dripping the obtained reaction solution into 40 percent dimethylamine aqueous solution under the condition of keeping the temperature at 80-100 ℃, controlling the reaction temperature to reflux at 50 ℃, controlling the dripping time to be 1-2 hours, and then keeping the temperature for 1-2 hours for reaction;
4) slowly dripping liquid alkali raw materials at the temperature of 50-70 ℃, simultaneously carrying out reduced pressure distillation to recover excessive dimethylamine, wherein the dripping time is 1-2 hours, after the dripping is finished, heating, and controlling a reaction system to continuously react for 1-2 hours at the temperature of 80-100 ℃ to finish the reaction;
5) after the reaction is finished, transferring the reaction solution into an extraction kettle while the reaction solution is hot, and adding toluene or xylene for extraction, wherein the extraction temperature is 80-100 ℃;
6) adding the organic phase obtained by extraction into active carbon for decolorization and filtration, and cooling to separate out white crystals, namely the product 4-dimethylaminopyridine;
7) adding hydrochloric acid into the raffinate phase obtained by extraction to adjust the pH value to 5-7, adding the next batch of raw material 4-cyanopyridine at the temperature of 90-100 ℃ for extraction and recovery, directly putting the extracted organic phase into the next batch of reaction kettle, and beginning the next batch of reaction after supplementing part of raw materials.
2. The process of claim 1, wherein the liquid caustic is sodium hydroxide.
3. The novel process for the preparation of 4-dimethylaminopyridine according to claim 2, wherein the molar ratio of the starting materials is 4-cyanopyridine: acrylic acid: hydrochloric acid: hydroquinone: dimethylamine: sodium hydroxide ═ 1.0: 1.1-1.3: 2.2-3.3: 0.0055-0.0065: 2.0-4.0: 4.0-6.0.
4. The process of claim 1, 2 or 3 wherein the recovery of acrylic acid in the process is greater than 93%, the yield of 4-dimethylaminopyridine based on 4-cyanopyridine is greater than 97%, and the content of 4-dimethylaminopyridine is greater than 99.0%.
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| CN114478369A (en) * | 2022-01-11 | 2022-05-13 | 浙江工业大学 | Method for continuously preparing 4-dimethylaminopyridine by using microchannel reactor |
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| CN109608332A (en) * | 2019-01-18 | 2019-04-12 | 西安优耐特容器制造有限公司 | The method for being catalyzed continuous 14 ester of acrylic acid synthesizing using microwave-microreactor |
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| CN103787963A (en) * | 2013-12-20 | 2014-05-14 | 安徽国星生物化学有限公司 | Efficient preparation of 4-dimethylaminopyridine |
| CN109608332A (en) * | 2019-01-18 | 2019-04-12 | 西安优耐特容器制造有限公司 | The method for being catalyzed continuous 14 ester of acrylic acid synthesizing using microwave-microreactor |
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| CN114478369A (en) * | 2022-01-11 | 2022-05-13 | 浙江工业大学 | Method for continuously preparing 4-dimethylaminopyridine by using microchannel reactor |
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