CN116120188A - Synthesis method of N-methyl dibutylamine - Google Patents
Synthesis method of N-methyl dibutylamine Download PDFInfo
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Abstract
The invention provides a synthesis method of N-methyl dibutylamine, which comprises the steps of reacting dibutylamine with organic acid to obtain dibutylamine organic acid salt; and then, the dibutylamine organic acid salt and formaldehyde undergo an N-methylation reaction, and the product is subjected to rectification treatment after being extracted by an extraction solvent, so that a final product N-methyl dibutylamine is obtained. The synthesis method takes formaldehyde as a carbon source and a reducing agent, and under mild reaction conditions, the conversion rate of dibutylamine is higher than 99% by controlling the proportion, the reaction time and the reaction temperature of each reactant, and the selectivity of the finally synthesized N-methyl dibutylamine is higher than 97%.
Description
Technical Field
The invention relates to the technical field of chemical intermediate synthesis, in particular to a mild synthesis method of N-methyl dibutylamine.
Background
N-methyldialkylamine is an important class of chemical intermediates, which has wide application and economic value. Among them, N-methyldibutylamine (CAS: 3405-45-6, also known as N-methyldibutylfuran) is used as an excellent organic solvent for identifying an optimized mobile phase system, and has a wide application in the fields of organic chemistry and biochemistry.
In the traditional organic chemical synthesis field, amine compounds are usually subjected to Eschweiler-Clarke reaction (Eschweiler-Clarke) by adopting amine or imine, formaldehyde and formic acid in methylation reaction, or highly toxic methyl iodide, dimethyl sulfate and the like are used as a methylation reagent, and the requirements on equipment are high due to the reaction temperature, pressure and corrosiveness, so that the safety problem is outstanding, the single-pass reaction time is long, and the industrial large-scale durable production is not facilitated. The prior art also explores the synthetic route and synthetic conditions of N-methyl dibutylamine.
For example, the invention patent application with publication number CN1597659A utilizes formaldehyde and saturated dialkylamine to prepare N-methyldialkylamine, avoids using noble metal catalysis, but the synthesis method has the problems of higher reaction pressure (1.44 MPa-3.2 MPa) and higher reaction temperature (120-160 ℃) and higher cost because degassing and water removal are needed in the subsequent treatment.
For example, in the patent application of the invention with publication number of CN110372517A, methanol is used as a carbon source, iridium complex is used for catalyzing amine to perform N-methylation reaction, the method needs to be performed in an anhydrous atmosphere under the protection of nitrogen, the single reaction time is up to 12-24 hours, and plate chromatography or column chromatography is needed for separation and purification, so that the yield is low and the cost is high.
For example, in the patent application of CN106986776a, methanol is used as a carbon source, N-methylation of an amine compound is achieved by photocatalysis, although the reaction temperature is low, the illumination time required by a single reaction still needs 1-8h, and the molar ratio of the reducing agent to the amine compound is 80: more than 1, the required raw materials are large in quantity.
For another example, the invention disclosed in CN110201720a uses a binuclear rhodium complex to perform N-methylation reaction on aliphatic amine compound, and the technical scheme uses virulent methyl iodide as reducing agent, which is not beneficial to industrial application.
For another example, in the patent application of CN103288660a, dimethyl sulfoxide is used as a solvent, and the mixed reaction of aromatic amine, formic acid and triethylamine is performed to prepare N-methylated aromatic amine, so that the reaction temperature is reduced, but the single reaction time still needs 12-24 hours, the optimal yield is 92%, and the yields of the other products are all lower than 90%.
Therefore, the method for synthesizing the N-methyldibutylamine has practical significance in developing a method with mild reaction conditions and short reaction time.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a method for synthesizing N-methyl dibutylamine, which adopts dibutylamine to react with organic acid to obtain dibutylamine organic acid salt; and then the dibutylamine organic acid salt and formaldehyde undergo an N methylation reaction to obtain a product. Under mild reaction conditions, the conversion rate of dibutylamine is higher than 99% by controlling the proportion, the reaction time and the reaction temperature of each reactant, and the selectivity of the finally synthesized N-methyl dibutylamine is higher than 97%.
In order to achieve the above object, the present invention provides the following technical solutions:
a synthetic method of N-methyl dibutylamine, take dibutylamine and organic acid to react, get dibutylamine organic acid salt; and then, the dibutylamine organic acid salt and formaldehyde undergo an N-methylation reaction, and the product is subjected to rectification treatment after being extracted by an extraction solvent, so that a final product N-methyl dibutylamine is obtained.
As further description of the technical scheme of the invention, the synthesis method of the N-methyl dibutylamine specifically comprises the following steps:
s1, dibutylamine reacts with organic acid at 0-40 ℃ to obtain dibutylamine organic acid salt;
s2, carrying out N methylation reaction on the dibutylamine organic acid salt and formaldehyde at the temperature of 40-100 ℃;
s3, taking the reaction liquid of the S2, adding an extraction solvent, standing and extracting, and taking out an upper oil phase part;
s4, distilling the oil phase part of the S3 under reduced pressure to obtain the N-methyl dibutylamine liquid.
As a further description of the technical scheme of the invention, the specific reaction formula of the N-methyldibutylamine synthesis method is as follows:
in the method for synthesizing the N-methyl dibutylamine, dibutylamine reacts with organic acid to obtain dibutylamine organic acid salt, and then N-methylation reaction is carried out on the dibutylamine organic acid salt and formaldehyde which is taken as a carbon source and a reducing agent; in the reaction process, the organic acid has good catalytic activity, and can further improve the reaction performance of formaldehyde and dibutylamine. The conversion rate of the raw material dibutylamine can reach more than 99%, the raw material reaction is complete, and the subsequent separation operation process is simple and easy to implement; and the selectivity of the N-methyl dibutylamine can reach more than 97 percent, and almost all raw materials are converted into products with higher economic value.
As a further description of the technical scheme of the invention, in the S1, the mol ratio of the dibutylamine to the organic acid is 1:0.5-3.5.
As a further description of the technical scheme of the invention, in the S2, the reaction time of the N methylation reaction is 60-200min, and the molar ratio of the dibutylamine organic acid salt to the formaldehyde is 0.1-0.5:1-10.
As a further description of the technical scheme of the invention, the water content of the dibutylamine organic acid salt is 0-40%.
As a further description of the technical scheme of the invention, the water content of the dibutylamine organic acid salt is 10-30%.
According to the synthesis method of the N-methyl dibutylamine, provided by the invention, the N methylation reaction can be carried out under the mild conditions that the reaction time is 60-200min, the reaction temperature is 40-100 ℃, and the reaction pressure is normal pressure by controlling the mole ratio of the dibutylamine reactant, the organic acid and formaldehyde and the water content of the dibutylamine organic acid salt, so that the continuous production is facilitated.
As a further description of the technical scheme of the invention, the organic acid is glacial acetic acid, propionic acid or benzoic acid; the raw material of formaldehyde is formalin solution or paraformaldehyde.
According to the synthesis method of the N-methyl dibutylamine, the organic acid represented by glacial acetic acid and propionic acid has good catalytic activity, and the reaction performance of formaldehyde and dibutylamine can be further improved; and the higher conversion rate and selectivity of the reactant can be realized without catalysis of a noble metal catalyst.
The invention adopts formaldehyde as a carbon source and a reducing agent, has mild reaction conditions, avoids using methyl iodide, dimethyl sulfate, tertiary butyl hydroperoxide, a cyanamide solution and other extremely toxic and corrosive methylation reagents, and is beneficial to promoting the application of the reaction in actual production.
As a further description of the technical scheme of the invention, in the step S3, the extraction solvent is petroleum ether, and the petroleum ether dosage is 1-6 times of the total mass of the reaction solution.
As a further description of the technical scheme of the invention, the N-methyldibutylamine is synthesized in a kettle reactor, and the reaction pressure is kept at 0.08-12 MPa. The synthesis method of the N-methyl dibutylamine can be used for reaction under normal pressure, and is simple and easy to operate.
Based on the technical scheme, compared with the prior art, the invention has the following technical effects:
(1) The synthesis method of N-methyl dibutylamine provided by the invention has the advantages that the cost of the main raw materials is low, the use of reagents such as formic acid, tertiary butyl hydroperoxide, cyanamide solution, ethyl chloroformate and the like is avoided, the requirement on equipment is reduced, and the application of the synthesis method in actual production is facilitated.
(2) The synthesis method of N-methyl dibutylamine uses formaldehyde as a carbon source and a reducing agent, avoids using highly toxic methyl iodide, dimethyl sulfate, tertiary butyl hydroperoxide, a cyanamide solution and other methylation reagents, reduces the cost and improves the reaction safety.
(3) According to the method for synthesizing the N-methyl dibutylamine, disclosed by the invention, the organic acid is used as a catalyst, so that the catalyst has good catalytic activity, and the reaction performance of formaldehyde and dibutylamine can be further improved; the synthesis method can realize higher conversion rate and selectivity of reactants without catalysis of noble metal catalysts: the conversion rate of the raw material dibutylamine can reach more than 99%, the raw material reaction is complete, and the subsequent separation process is simplified; the selectivity of the N-methyl dibutylamine can reach more than 97%, and almost all raw materials are converted into products with higher economic value.
(4) The synthesis method of N-methyl dibutylamine has the advantages of mild reaction conditions, short reaction time, reaction at normal pressure, simplicity, convenience, easiness in operation and contribution to continuous production.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of N-methyldibutylamine of example 1 of the present invention.
FIG. 2 is a gas chromatogram of dibutylamine of example 1 of the present invention.
FIG. 3 is a gas chromatogram of N-methyldibutylamine of example 1 of the present invention.
FIG. 4 is a gas chromatogram of a mixture of dibutylamine and N-methyldibutylamine.
Detailed Description
In order that the invention may be readily understood, a more particular description of the invention will be rendered by reference to specific embodiments that are illustrated in the appended drawings. The drawings illustrate preferred embodiments of the invention. This invention may, however, be embodied in many different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention.
The specific reaction formula of the synthesis method of the N-methyl dibutylamine is as follows:
the synthesis method of the N-methyl dibutylamine specifically comprises the following steps:
s1, dibutylamine and organic acid react at 0-40 ℃ to obtain dibutylamine organic acid salt, wherein the molar ratio of dibutylamine to organic acid is 1:0.5-3.5; the water content of the dibutylamine organic acid salt is 0-40%, preferably 10-30%; the organic acid is glacial acetic acid or propionic acid;
s2, performing N methylation reaction on dibutylamine organic acid salt and formaldehyde at the temperature of 40-100 ℃, wherein the reaction time is 60-200min, and the molar ratio of dibutylamine organic acid salt to formaldehyde is 0.1-0.5:1-10; the formaldehyde is formalin solution or paraformaldehyde
S3, taking the reaction liquid of the S2, adding petroleum ether, standing and extracting, and taking out an upper oil phase part; the petroleum ether consumption is 1-6 times of the total mass of the reaction solution;
s4, distilling the oil phase part of the S3 under reduced pressure to obtain the N-methyl dibutylamine liquid.
The reaction is carried out in a kettle type reactor, and the reaction pressure is normal pressure or can be kept at 0.08-12 MPa.
The reaction effect analysis method is as follows: the reaction system was sampled and analyzed by Gas Chromatography (GC).
Example 1
To a 500mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant pressure dropping funnel, 130.55g of dibutylamine, 72.08g of deionized water were added, stirring was turned on, and after the temperature of the dibutylamine-water mixed solution reached 20 ℃, 66.39g of glacial acetic acid was added dropwise thereto. After completion of the dropwise addition, the reaction was carried out for 30 minutes, whereby dibutylamine acetate having a water content of 26% was obtained.
26.9g of dibutylamine acetate is taken in a 250mL three-neck round-bottom flask, 85.8g of formalin solution is taken in a constant-pressure dropping funnel, the constant-pressure dropping funnel and the three-neck round-bottom flask are fixed, then the constant-pressure dropping funnel and the three-neck round-bottom flask are placed in a constant-temperature water bath kettle at 70 ℃ for heating, after the temperature of liquid in the bottle is stabilized at 70 ℃, the constant-pressure dropping funnel is opened, all formalin is rapidly added, a knob is closed, the system is kept at 70 ℃ for stabilizing, after the reaction is carried out for 240min, the temperature is cooled to room temperature, the quality is weighed, and a small amount of liquid is taken for gas chromatographic analysis. Then 300mL of petroleum ether is added, the upper oil phase is taken after standing, and N-methyl dibutylamine is obtained after decompression and rotary evaporation. And performing nuclear magnetic resonance analysis on the prepared N-methyldibutylamine prepared sample, wherein an analysis spectrum is shown as a nuclear magnetic resonance spectrum of the 3N-methyldibutylamine in figure 1.
Fig. 2 and 3 are gas chromatograms of dibutylamine and N-methyldibutylamine of this example, respectively, as shown in fig. 2 and 3, using methanol as a diluent and tetrahydrofuran as an internal standard, and analyzed by gas chromatography internal standard, the dibutylamine conversion was 99.8% and the N-methyldibutylamine selectivity was 93%.
Fig. 4 shows a gas chromatogram of a mixed sample of dibutylamine and N-methyldibutylamine, and it is clear from fig. 4 that during the detection process, the dibutylamine as a raw material and the N-methyldibutylamine as a product can be detected separately, and the separation degree meets the requirement.
Example 2
To a 250mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant pressure dropping funnel, 66.12g of dibutylamine and 36.51g of deionized water were added, stirring was turned on, and after the temperature of the dibutylamine-water mixed solution reached 10 ℃, 33.63g of glacial acetic acid was added dropwise thereto. After completion of the dropwise addition, the reaction was carried out for 60 minutes, whereby dibutylamine acetate having a water content of 27% was obtained.
13.45g of dibutylamine acetate is taken in a 250mL three-neck round-bottom flask, 85.8g of formalin solution is taken in a constant-pressure dropping funnel, the constant-pressure dropping funnel and the three-neck round-bottom flask are fixed, then the constant-pressure dropping funnel and the three-neck round-bottom flask are placed in a constant-temperature water bath kettle at 80 ℃ for heating, after the temperature of liquid in the bottle is stabilized at 80 ℃, the constant-pressure dropping funnel is opened, all formalin is rapidly added, a knob is closed, the system is kept at 80 ℃ for 120min, after the reaction, the system is cooled to room temperature, the mass is weighed, and a small amount of liquid is taken for gas chromatographic analysis. Then 500mL of petroleum ether is added, the upper oil phase is taken after standing, and N-methyl dibutylamine is obtained after decompression and rotary evaporation.
Tetrahydrofuran is used as an internal standard, and the conversion rate of dibutylamine is 99.9% and the selectivity of N-methyl dibutylamine is 98% by gas chromatography internal standard analysis.
Example 3
To a 250mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant pressure dropping funnel, 83.22g of dibutylamine, 55.95g of deionized water were added, stirring was turned on, and after the temperature of the dibutylamine-water mixed solution reached 15 ℃, 42.32g of glacial acetic acid was added dropwise thereto. After completion of the dropwise addition, the reaction was carried out for 90 minutes, whereby dibutylamine acetate having a water content of 31% was obtained.
13.45g of dibutylamine acetate is taken in a 250mL three-neck round-bottom flask, 42.9g of formalin solution is taken in a constant-pressure dropping funnel, the constant-pressure dropping funnel and the three-neck round-bottom flask are fixed, then the constant-pressure dropping funnel and the three-neck round-bottom flask are placed in a constant-temperature water bath kettle at 90 ℃ for heating, after the temperature of liquid in the bottle is stabilized at 90 ℃, the constant-pressure dropping funnel is opened, all formalin is rapidly added, a knob is closed, a system is kept at 90 ℃ for 120min, the reaction is carried out, the reaction is cooled to room temperature, the mass is weighed, a small amount of liquid is taken for gas chromatographic analysis, then 200mL of petroleum ether is added for standing, and then an upper oil phase is taken, and the N-methyl dibutylamine is obtained through reduced pressure rotary evaporation.
Tetrahydrofuran is used as an internal standard, and the conversion rate of dibutylamine is 99.0% and the selectivity of N-methyl dibutylamine is 90% by gas chromatography internal standard analysis.
Example 4
To a 250mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant pressure dropping funnel, 83.22g of dibutylamine, 75.95g of deionized water were added, stirring was turned on, and after the temperature of the dibutylamine-water mixed solution reached 15 ℃, 42.32g of propionic acid was added dropwise thereto. After completion of the dropwise addition, the reaction was carried out for 90 minutes, whereby dibutylamine propionate having a water content of 37% was obtained.
13.45g of dibutylamine propionate is taken in a 250mL three-neck round bottom flask, 42.9g of formalin solution is taken in a constant pressure dropping funnel, the constant pressure dropping funnel and the three-neck round bottom flask are fixed, then the constant pressure dropping funnel and the three-neck round bottom flask are placed in a constant temperature water bath kettle for heating, after the temperature of liquid in the bottle is stabilized at 60 ℃, the constant pressure dropping funnel is opened, all formalin is rapidly added, a knob is closed, a system is kept at 60 ℃ for 240min, the reaction is carried out, the reaction is cooled to room temperature, the mass is weighed, a small amount of liquid is taken for gas chromatographic analysis, then 200mL of petroleum ether is added for standing, the upper oil phase is taken, and the N-methyl dibutylamine is obtained through reduced pressure rotary evaporation.
Tetrahydrofuran is used as an internal standard, and the conversion rate of dibutylamine is 99.7% and the selectivity of N-methyl dibutylamine is 63% by gas chromatography internal standard analysis.
Example 5
To a 500mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant pressure dropping funnel, 212.52g of dibutylamine, 40g of deionized water were added, stirring was turned on, and after the temperature of the dibutylamine-water mixed solution reached 15 ℃, 108.08g of benzoic acid was added dropwise thereto. After completion of the dropwise addition, the reaction was carried out for 120 minutes, whereby dibutylbenzoate having a water content of 11% was obtained.
25.74g of formalin solution is taken in a 250mL three-neck round-bottom flask, 26.9g of dibutylamine benzoate is taken in a constant-pressure dropping funnel, the constant-pressure dropping funnel and the three-neck round-bottom flask are fixed, then the flask is placed in a constant-temperature water bath kettle at 75 ℃ for heating, after the temperature of liquid in the flask is stabilized at 60 ℃, the constant-pressure dropping funnel is opened, the dibutylamine benzoate is slowly added in a dropwise manner within 30min, the system is kept at 60 ℃, after the reaction is carried out for 240min, the system is cooled to room temperature, the mass is weighed, a small amount of liquid is taken for gas chromatography analysis, 200mL of petroleum ether is added for standing, and then the upper oil phase is taken, and the N-methyl dibutylamine is obtained through reduced pressure rotary evaporation.
Tetrahydrofuran is used as an internal standard, and the conversion rate of dibutylamine is 99.6% and the selectivity of N-methyl dibutylamine is 73% by gas chromatography internal standard analysis.
Example 6
To a 250mL three-necked flask equipped with a thermometer, a condenser, a stirrer and a constant-pressure dropping funnel was added 39.12g of dibutylamine, 24.35g of formalin solution and 15.68g of formic acid (wt 88%) were placed in the constant-pressure dropping funnel, the constant-pressure dropping funnel and the three-necked round bottom flask were fixed, and after the round bottom flask was placed in a constant-temperature water bath at 70℃to be heated, stirring was turned on. After the temperature of the liquid in the bottle is stabilized at 70 ℃, dropwise adding the mixture of formalin and formic acid in 20min, keeping the system at 70 ℃, reacting for 120min, cooling to room temperature, layering the solution, reserving the upper layer of liquid, weighing and taking a small amount of liquid for gas chromatography analysis.
Tetrahydrofuran is used as an internal standard, and the conversion rate of dibutylamine is 99.6% and the selectivity of N-methyl dibutylamine is 92% by gas chromatography internal standard analysis.
Specific experimental data on the conversion of dibutylamine and the selectivity of N-methyldibutylamine corresponding to example 1-example 6 are shown in table 1.
TABLE 1 conversion of dibutylamine and N-methyldibutylamine Selectivity corresponding to example 1-example 6
Dibutylamine molar mass (g/mol): 129.24; n-methyldibutylamine molar mass (g/mol): 143.27
As can be seen from table 1, the synthesis method of N-methyldibutylamine provided in the above example adopts dibutylamine to react with organic acid to obtain dibutylamine organic acid salt; and then the dibutylamine organic acid salt and formaldehyde undergo an N methylation reaction to obtain a product. Under mild reaction conditions, the conversion rate of dibutylamine is higher than 99% by controlling the proportion, the reaction time and the reaction temperature of each reactant. Wherein the selectivity of the N-methyldibutylamine of example 2 reaches 98%.
The foregoing is merely illustrative and explanatory of the invention as it is described in more detail and is not thereby to be construed as limiting the scope of the invention. It should be noted that modifications and improvements can be made by those skilled in the art without departing from the spirit of the invention, and that these obvious alternatives fall within the scope of the invention.
Claims (10)
1. A synthesis method of N-methyl dibutylamine is characterized in that dibutylamine is taken to react with organic acid to obtain dibutylamine organic acid salt; and then, the dibutylamine organic acid salt and formaldehyde undergo an N-methylation reaction, and the product is subjected to rectification treatment after being extracted by an extraction solvent, so that a final product N-methyl dibutylamine is obtained.
2. The method for synthesizing the N-methyldibutylamine according to claim 1, comprising the following steps:
s1, dibutylamine reacts with organic acid at 0-40 ℃ to obtain dibutylamine organic acid salt;
s2, carrying out N methylation reaction on the dibutylamine organic acid salt and formaldehyde at the temperature of 40-100 ℃;
s3, taking the reaction liquid of the S2, adding an extraction solvent, standing and extracting, and taking out an upper oil phase part;
s4, distilling the oil phase part of the S3 under reduced pressure to obtain the N-methyl dibutylamine liquid.
3. The method for synthesizing N-methyldibutylamine according to claim 2, wherein the specific reaction formula is:
4. the method for synthesizing N-methyldibutylamine according to claim 2, wherein in S1, a molar ratio of the dibutylamine to the organic acid is 1:0.5 to 3.5.
5. The method for synthesizing N-methyldibutylamine according to claim 2, wherein in S2, the reaction time of the N-methylation reaction is 60 to 200min, and the molar ratio of the dibutylamine organic acid salt to formaldehyde is 0.1 to 0.5:1 to 10.
6. The method for synthesizing N-methyldibutylamine according to claim 2, wherein the water content of the dibutylamine organic acid salt is 0 to 40%.
7. The method for synthesizing N-methyldibutylamine according to claim 6, wherein the water content of the dibutylamine organic acid salt is 10-30%.
8. The method for synthesizing N-methyldibutylamine according to claim 2, wherein the organic acid is glacial acetic acid, propionic acid, or benzoic acid; the raw material of formaldehyde is formalin solution or paraformaldehyde.
9. The method for synthesizing N-methyldibutylamine according to claim 2, wherein in S3, the extraction solvent is petroleum ether, and the petroleum ether is used in an amount of 1 to 6 times the total mass of the reaction solution.
10. The method for synthesizing N-methyldibutylamine according to any one of claims 1 to 9, wherein the reaction pressure is kept at 0.08 to 12MPa.
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