CN108727203B - Method for continuously producing N-alkyl m-aminophenol by fixed bed - Google Patents
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Abstract
The invention discloses a method for continuously producing N-alkyl m-aminophenol by a fixed bed, belonging to the technical field of chemical synthesis. The invention utilizes the catalyst and adopts a fixed bed to continuously produce the N-alkyl m-aminophenol. The catalyst has high reaction activity, mild temperature requirement, short reaction time and almost no side reaction, and the method of continuous production by using the fixed bed has the advantages of high production capacity, low equipment investment, stable product quality and the like. The invention also has the advantages of small environmental pollution, relatively safe operation and the like.
Description
Technical Field
The invention relates to a method for continuously producing N-alkyl m-aminophenol by a fixed bed, belonging to the technical field of chemical synthesis.
Background
An N-alkyl meta-aminophenol having the formula:
wherein R is C1-9An alkyl group.
N-alkyl meta-aminophenol is an important organic intermediate and is widely applied to the industries of dyes, medicines, pesticides and the like. With the spread of facsimile technology, N-alkyl meta-aminophenol is also used for the fabrication of pressure/heat sensitive materials.
Several methods for producing N-alkyl meta-aminophenol have been reported
The method 1 comprises the steps of taking phenol or alkylphenol and ammonia gas as raw materials, taking alumina as a carrier, taking metal such as loaded Pd, Sn and the like as a catalyst, pressurizing to 0.1-0.2 MPa by using hydrogen, and reacting at 200 ℃ (CN 1381440). The reaction uses noble metal Pd as a catalyst, the reaction temperature is high, the ammonia gas toxicity is high, certain harm is caused to human bodies, and potential safety hazards exist.
Method 2, resorcinol and secondary amine are used as raw materials, Raney nickel is used as a catalyst, pressure is increased to 0.05Mpa in an autoclave, and stirring is carried out for 3h at 200 ℃ (Ge X, Pan J B, Qian C, et al. The reaction uses higher reaction temperature, and the Raney nickel has overhigh catalytic activity and certain safety risk.
Method 3, resorcinol and ethylamine are used as raw materials, ZnCl2 is used as a catalyst, hydrogen is used for pressurizing to 0.62MPa in a high-pressure reaction kettle, and stirring is carried out for 6h at 175 ℃ (JP 2011012053). The reaction has high use temperature, tin chloride can pollute the environmental water, and the yield of the N-ethyl m-aminophenol is not high and is 75.36%.
Disclosure of Invention
In order to solve the problems, the invention provides a method for continuously producing N-alkyl m-aminophenol, which has the advantages of mild reaction conditions, high resorcinol conversion rate and yield, and good N-alkyl m-aminophenol selectivity.
The method for continuously producing the N-alkyl m-aminophenol comprises the steps of placing a supported catalyst in a fixed bed, and carrying out continuous production by using resorcinol and alkylamine as raw materials through the fixed bed.
In one embodiment, the sum of the metals in the supported catalyst is from 15 to 40% by weight of the total supported catalyst.
In one embodiment, the supported catalyst consists of a carrier and a metal salt, wherein the carrier is gamma-Al2O3The metal salt is more than one of the following: nickel nitrate, magnesium nitrate and zinc nitrate.
In one embodiment, the supported catalyst is a supported nickel-based catalyst and Ni comprises 10% of the total weight of the supported catalyst.
In one embodiment, the supported catalyst is Ni-Mg-Zn/gamma-Al2O3。
In one embodiment, the method comprises:
(1) placing the supported catalyst in a fixed bed; preheating a fixed bed, injecting a solution of resorcinol and alkylamine into the fixed bed by a pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed with hydrogen, and reacting for a period of time;
(2) continuously extracting feed liquid;
(3) after the feed liquid is cooled, the high-purity N-alkyl m-aminophenol is obtained after filtration and concentration.
In one embodiment, the method comprises:
(1) preheating a fixed bed to 90-130 ℃, dissolving resorcinol and alkylamine in a solvent according to a molar ratio of 1: 1-1: 5 to prepare a solution, maintaining the temperature of the solution below 20 ℃ (0-20 ℃), injecting the solution into the fixed bed by using a metering pump, replacing air in the fixed bed by using hydrogen, pressurizing the fixed bed by using the hydrogen (0.5-2 MPa), and controlling the reaction time by the flow of the metering pump and the residence time in the fixed bed;
(2) continuously extracting feed liquid by using a rotary disc extraction tower, and collecting an organic phase flowing out of the extraction tower by using a liquid storage tank;
(3) and after the feed liquid is naturally cooled to room temperature, filtering and concentrating to obtain the high-purity N-alkyl m-aminophenol.
In one embodiment, the solvent is an alcohol solvent such as water, methanol, or ethanol.
In one embodiment, the preheating is carried out to 100-130 ℃.
In one embodiment, the molar ratio of resorcinol to alkylamine is from 1:1.2 to 1: 1.5.
In one embodiment, the reaction time and residence time for the addition of the materials is 3 to 6 hours.
In one embodiment, the continuous extraction employs an extraction solution of ethyl acetate, n-butyl acetate, or the like.
In one embodiment, the reaction equation for the synthesis of N-alkyl meta-aminophenol of the present invention is as follows:
wherein R is C1-9An alkyl group.
The invention has the beneficial effects that:
the fixed bed of the invention continuously produces the N-alkyl meta-aminophenol, and has the following advantages:
1. the supported catalyst has high reaction activity, mild temperature requirement, short reaction time and almost no side reaction, and the method of using the fixed bed for continuous production has large production capacity, small equipment investment, stable product quality and the like;
2. the resorcinol and alkylamine are adopted as raw materials to continuously react in a fixed bed, and compared with the resorcinol and ethylamine process, the resorcinol and alkylamine compound continuous reaction process has the advantages of mild reaction conditions, small environmental pollution and relatively safe operation.
Drawings
FIG. 1 is a fixed bed continuous reactor.
Detailed Description
Example 1
A fixed bed continuous reactor is shown in FIG. 1.
The supported catalyst is placed in a fixed bed, the solution is injected into the fixed bed from a raw material storage tank by a metering pump, the flow of the raw material solution is controlled by the metering pump, and the fixed bed is provided with a sleeve pipe for heating a medium and can be used for controlling the reaction temperature. Feeding the raw material solution into the fixed bed from the upper part of the fixed bed; the mixed product of the reaction continuously flows out from the bottom of the fixed bed, then is injected into the rotary disc extraction tower through a metering pump, and the organic phase flowing out of the extraction tower is collected by a liquid storage tank and is naturally cooled to the room temperature.
Example 2
Preparation of the catalyst:
①, mixing 100g of gamma-Al2O3(particle diameter of 20nm, specific surface area of 220-250 m)2Per g) 80ml of 12% H3PO4Soaking the solution at 40-60 deg.C for 30 min. Mixing gamma-Al2O3Filtered and dried at 70 ℃ for 2h, then placed in a muffle furnace and calcined at 450 ℃ for 3 h.
②, mixing 100g of Ni (NO)3)299g of Mg (NO)3)246.5g of Zn (NO)3)2Formulating the treated gamma-Al from step ① with 100ml of deionized water to form a metal salt solution2O3Soaking for 8 hr, stirring, drying at 70 deg.C for 2 hr, placing into a muffle furnace,drying at 120 ℃ for 3h, and then roasting at 400-450 ℃ for 6h to obtain the catalyst. The supported catalyst Ni-Mg-Zn/gamma-Al2O3In the catalyst, Ni, Mg and Zn respectively account for 10 percent, 5 percent and 5 percent of the total weight of the supported catalyst.
Further, in the preparation of the supported catalyst, Ni (NO) was adjusted3)2，Mg(NO3)2，Zn(NO3)2The same as above for the other methods, to obtain catalysts with different metal loading.
Example 3
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) 100g of supported catalyst with Ni, Mg and Zn supporting amounts of 10%, 5% and 5% is placed in an internal filler of a fixed bed; the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed reservoir by a metering pump and stored in the raw material reservoir while the temperature of the material was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 98.2 percent.
Example 4
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-propylamine as raw materials, and sequentially comprises the following steps:
(1) 100g of supported catalyst with Ni, Mg and Zn supporting amounts of 10%, 5% and 5% is placed in an internal filler of a fixed bed; the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 14.2g (0.24mol) of n-propylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed reservoir by a metering pump and stored in the raw material reservoir while the temperature of the material was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-propyl m-aminophenol as the product and ethyl acetate as the extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-propyl m-aminophenol with the yield of 97.6 percent.
Example 5
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) 100g of supported catalyst with Ni, Mg and Zn supporting amounts of 10%, 5% and 5% is placed in an internal filler of a fixed bed; the fixed bed was preheated to 100 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed storage tank by a metering pump and stored in the raw material storage tank with the material temperature maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 100 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 97.3 percent.
Example 6
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-pentylamine as raw materials, and sequentially comprises the following steps:
(1) 100g of supported catalyst with Ni, Mg and Zn supporting amounts of 10%, 5% and 5% is placed in an internal filler of a fixed bed; the fixed bed was preheated to 130 ℃, 22g (0.2mol) of resorcinol and 26.1g (0.3mol) of n-pentylamine were dissolved in 200ml of methanol (as a solvent) to prepare a solution, the solution was injected into the fixed bed reservoir by a metering pump, the solution was stored in the raw material reservoir, and the material temperature was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and removing the solvent ethyl acetate by reduced pressure distillation to finally obtain the N-amyl m-aminophenol with the yield of 96.4 percent.
Example 7
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) 100g of supported catalyst with Ni, Mg and Zn supporting amounts of 10%, 5% and 5% is placed in an internal filler of a fixed bed; the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of methanol as a solvent to prepare a solution, and the solution was injected into the fixed bed reservoir by a metering pump and stored in the raw material reservoir while the temperature of the material was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 1.5MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 110 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 96.8 percent.
Example 3 to example 7:
changing the reaction conditions: the molar ratio of alkylamine to resorcinol, the type of alkylamine, the type of solvent, the reaction pressure and the reaction temperature, and example 3-7 are obtained, and the specific data are shown in table 1.
TABLE 1 data from examples 3 to 7
The yield (amount of the target product produced after rectification/amount of the reactant fed) × 100%.
Example 8
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 100 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed storage tank by a metering pump and stored in the raw material storage tank with the material temperature maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 100 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 86.2 percent.
Example 9
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 18.98g (0.26mol) of n-butylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed storage tank by a metering pump and stored in the raw material storage tank with the material temperature maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 88.1 percent.
Example 10
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of water as a solvent to prepare a solution, and the solution was injected into the fixed bed reservoir by a metering pump and stored in the raw material reservoir while the temperature of the material was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 0.5MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 85.2 percent.
Example 11
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 100 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of methanol as a solvent to prepare a solution, and the solution was injected into the fixed bed storage tank by a metering pump and stored in the raw material storage tank with the material temperature maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 100 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 84.6 percent.
Example 12
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 18.98g (0.26mol) of n-butylamine were dissolved in 200ml of methanol as a solvent to prepare a solution, and the solution was injected into the fixed bed storage tank by a metering pump and stored in the raw material storage tank with the material temperature maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 2MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 85.3 percent.
Example 13
A method for continuously producing N-alkyl m-aminophenol by a fixed bed takes resorcinol and N-butylamine as raw materials, and sequentially comprises the following steps:
(1) the fixed bed was preheated to 130 ℃ and 22g (0.2mol) of resorcinol and 21.9g (0.3mol) of n-butylamine were dissolved in 200ml of methanol as a solvent to prepare a solution, and the solution was injected into the fixed bed reservoir by a metering pump and stored in the raw material reservoir while the temperature of the material was maintained at room temperature. Injecting the solution into the fixed bed by a metering pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed to 0.5MPa by hydrogen, starting stirring for reaction, controlling the reaction time by the flow rate of the metering pump and the retention time in the fixed bed,
the reaction temperature was 130 ℃ and the reaction time was about 4 hours.
(2) Injecting the reaction mixture into a rotary disc extraction tower through a metering pump, collecting an organic phase flowing out of the extraction tower by a liquid storage tank, and naturally cooling to room temperature. (consisting essentially of N-butyl-m-aminophenol as product and ethyl acetate as extract)
(3) And filtering the organic phase, and distilling under reduced pressure to remove the solvent ethyl acetate to finally obtain the N-butyl m-aminophenol with the yield of 78.3 percent.
Example 8 to example 13:
in comparison with example 3, the reaction conditions were varied: the molar ratio of n-butylamine to resorcinol, the type of solvent, the reaction pressure and the reaction temperature gave examples 8 to 13, and the data are shown in Table 2.
Table 2 data from example 8 to example 13
Comparative example 1:
compared with the example 3, the difference is only that the supported catalyst Ni-Mg-Zn/gamma-Al with 15 percent, 10 percent and 5 percent of Ni-Mg-Zn is adopted2O3The catalyst of example 3 was substituted with 10%, 5%, 5% Ni-Mg-Zn loading and the other steps or parameters were in accordance with example 3.
The results showed that the yields were 94.2%, respectively.
Comparative example 2:
the only difference compared to example 3 was that tin chloride catalyst was used instead of the catalyst with Ni-Mg-Zn loadings of 10%, 5% in example 3, and the other steps or parameters were consistent with example 3.
The result showed a yield of 66.8%.
Although the present invention has been described with reference to the preferred embodiments, it should be understood that various changes and modifications can be made therein by those skilled in the art without departing from the spirit and scope of the invention as defined in the appended claims.
Claims (8)
1. The method for producing the N-alkyl m-aminophenol is characterized by comprising the steps of placing a supported catalyst in a fixed bed, and carrying out continuous production by using resorcinol and alkylamine as raw materials through the fixed bed; the supported catalyst is prepared from a carrier and metal salt, wherein the carrier is gamma-Al2O3The metal salt is nickel nitrate, magnesium nitrate and zinc nitrate, and the sum of the metals accounts for 15-40% of the total weight of the supported catalyst; wherein Ni accounts for 10% of the total weight of the supported catalyst.
2. The method according to claim 1, characterized in that it comprises:
(1) placing the supported catalyst in a fixed bed; preheating a fixed bed, injecting a solution of resorcinol and alkylamine into the fixed bed by a pump, replacing air in the fixed bed with hydrogen, pressurizing the fixed bed with hydrogen, and reacting for a period of time;
(2) continuously extracting feed liquid;
(3) after the feed liquid is cooled, the high-purity N-alkyl m-aminophenol is obtained after filtration and concentration.
3. The method according to claim 1, characterized in that it comprises:
(1) preheating a fixed bed to 90-130 ℃, dissolving resorcinol and alkylamine in a solvent according to a molar ratio of 1: 1-1: 1.5 to prepare a solution, maintaining the temperature of the solution below 20 ℃, injecting the solution into the fixed bed by using a metering pump, replacing air in the fixed bed by using hydrogen, pressurizing the fixed bed by using the hydrogen, and controlling the reaction time by the flow of the metering pump and the retention time in the fixed bed;
(2) continuously extracting feed liquid by using a rotary disc extraction tower, and collecting an organic phase flowing out of the extraction tower by using a liquid storage tank;
(3) and after the feed liquid is naturally cooled to room temperature, filtering and concentrating to obtain the high-purity N-alkyl m-aminophenol.
4. The method of claim 3, wherein the solvent is water or an alcohol solvent.
5. The method of claim 2, wherein the molar ratio of resorcinol to alkylamine is from 1:2 to 1: 5.
6. The method of claim 2, wherein the reaction time and residence time of the added materials is 3 to 6 hours.
7. The process of claim 2, wherein the continuous extraction is carried out using ethyl acetate or n-butyl acetate as the extraction solvent.
8. The method of claim 2, wherein the reaction occurring in the method has the following equation:
wherein R is C1-9 alkyl.
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| EP0402935A3 (en) * | 1989-06-16 | 1992-02-26 | Mitsui Petrochemical Industries, Ltd. | Method of producing n-alkylaminophenols |
| JP3811819B2 (en) * | 1995-05-09 | 2006-08-23 | 山田化学工業株式会社 | Method for producing 3-N-monoalkylaminophenol or 3-N, N-dialkylaminophenol |
| US5856575A (en) * | 1997-01-22 | 1999-01-05 | Council Of Scientific Industrial Research | Process for the preparation of N-acetyl aminophenols |
| JP2011012053A (en) * | 2009-06-04 | 2011-01-20 | Sumitomo Chemical Co Ltd | Method for preparing n-alkylamino phenol |
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