CN110724063B - Method for preparing o-aminoanisole by adopting micro-flow field reaction technology - Google Patents
Method for preparing o-aminoanisole by adopting micro-flow field reaction technology Download PDFInfo
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- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
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Abstract
The invention provides a method for preparing o-aminoanisole by adopting a micro-flow field reaction technology, which takes o-aminophenol and nontoxic and pollution-free dimethyl carbonate (DMC) as raw materials under the action of a phase transfer catalyst or an alkaline catalyst, and adopts a micro-channel module reaction device for reaction.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing o-aminoanisole by adopting a micro-flow field reaction technology.
Background
Anthranilic ether, also known as o-anisidine. It is not only an important fine chemical product, but also an important intermediate for synthesizing fine chemical products such as medicine, pesticide, perfume, etc., and can be used for inhibiting polymerization and ultraviolet ray of ethylene high polymer monomer and synthesizing food antioxidant, and its application is very extensive. At present, the traditional synthetic methods of the o-aminoanisole mainly comprise two methods. 1. Dimethyl sulfate method: dimethyl sulfate is taken as a methylating agent and reacts with o-aminophenol under alkaline condition to prepare the compound; 2. the methanol method comprises the following steps: under the action of catalyst, o-aminophenol reacts with methanol to obtain the product. The synthesis methods have the defects that the dimethyl sulfate belongs to high-risk highly toxic and highly corrosive medicines, a large amount of alkali is needed to neutralize the by-product acid in the organic synthesis, and the yield is low and generally does not exceed 50%. The methanol method has the defects that the mixture of the mono-methyl ether and the bis-methyl ether is difficult to separate, the product quality is poor, and the problems restrict the production of the o-aminoanisole.
Disclosure of Invention
In order to synthesize the o-aminoanisole efficiently and greenly, the invention takes o-aminophenol and nontoxic and pollution-free dimethyl carbonate (DMC) as raw materials, and adopts a micro flow field reaction technology to synthesize the o-aminoanisole rapidly and efficiently under the action of a catalyst, in particular to a method for preparing the o-aminoanisole by adopting the micro flow field reaction technology, which comprises the following steps:
(1) mixing o-aminophenol with dimethyl carbonate or dimethyl sulfoxide to obtain a mixed system for later use;
(2) preparing a mixed solution of a catalyst and a solvent according to a certain proportion for later use;
(3) carrying out reaction on the prepared two mixed solutions at a certain temperature for a certain time by a micro-channel modular reaction device;
(4) and filtering and distilling the product obtained after the reaction, collecting the product, and analyzing the product.
As a modification, in the step (1), the solvent is dimethyl carbonate or dimethyl sulfoxide.
In the step (2), the catalyst comprises a first catalyst phase transfer catalyst and a second catalyst which is a basic catalyst or a metal catalyst, wherein the phase transfer catalyst is tetramethylammonium chloride, tetramethylammonium bromide or tetrabutylammonium bromide, and the second catalyst is sodium carbonate, potassium hydroxide, sodium hydroxide, cesium carbonate, organic amine, strongly basic anion exchange resin, cuprous iodide, cupric oxide, cupric chloride, cupric bromide, ferric acetate, silver nitrate or palladium acetate.
As an improvement, when the solvent is dimethyl carbonate, the reaction is carried out by reacting ortho-aminophenol: dimethyl carbonate: the molar ratio of the catalyst is 1: 10-25: 0.05 to 0.3.
As an improvement, the microchannel modular reaction device comprises a raw material storage tank, a micromixer, a microstructure reactor and a product collector which are sequentially connected through pipelines, wherein the raw material storage tank is provided with a plurality of groups; the reaction temperature is set to be 105-145 ℃, the reaction residence time is 12-25min, the flow rate of the mixed solution obtained after mixing by the micro mixer is 0.5-1.2mL/min, and the volume of the micro-structure reactor is 8-20 mL.
As an improvement, the distillation is to distill the solvent and the dimethyl carbonate at normal pressure, and then to distill at reduced pressure, and collect the fraction with the conditions of 580-610Pa and 130-140 ℃.
Has the advantages that: the method for preparing the o-aminoanisole by adopting the micro-flow field reaction technology provided by the invention takes o-aminophenol and nontoxic and pollution-free dimethyl carbonate (DMC) as raw materials under the action of a phase transfer catalyst or an alkaline catalyst, and adopts a micro-channel module reaction device for reaction.
Drawings
FIG. 1 is a schematic view of the structure of a microchannel module reactor apparatus of the present invention.
Detailed Description
The present invention is further illustrated below with reference to examples.
The synthetic route of the anthranilic ether in the technical scheme of the invention is as follows:
Mixing o-aminophenol and dimethyl carbonate or dimethyl sulfoxide to obtain a mixed system for later use, and placing the mixed system in a first raw material storage tank; and preparing a mixed solution of the catalyst and the solvent according to a certain proportion, placing the mixed solution in a second raw material storage tank, and sequentially passing the two groups of raw material storage tanks through a micro mixer, a micro-structure reactor and a product collector to obtain the product. The solvent is dimethyl carbonate or dimethyl sulfoxide.
The method has the characteristics of high catalytic efficiency, mild reaction conditions, high yield of the target compound, convenience in operation and the like, and has the characteristics of high catalytic efficiency, mild reaction conditions, high yield of the target compound, convenience in operation and the like.
The catalyst comprises a first catalyst phase transfer catalyst and the second catalyst is a basic catalyst or a metal catalyst. The first catalyst employs a phase transfer catalyst. The phase transfer catalyst is used for catalyzing two-phase reaction, and the reaction process mainly comprises the transfer of reactants from one phase to another phase and the chemical reaction of a transferred substance and a substance to be transferred. The phase transfer catalyst of the present invention comprises: tetramethylammonium chloride, tetramethylammonium bromide, or tetrabutylammonium bromide.
Preferably, in the method for preparing anthranilic acid ether according to the present invention, the phase transfer catalyst is tetrabutylammonium bromide. When tetrabutylammonium bromide is used as a phase transfer catalyst, very good results can be obtained both in terms of reaction yield and product purity.
In addition to the phase transfer catalyst, the catalyst in the synthesis method according to the embodiment of the present invention further includes a second catalyst. The second catalyst is primarily used to provide a specific environment. In some experimental approaches of the present invention, the inventors also investigated the effect of the type and amount of the second catalyst on the reaction yield. The results show that when the second catalyst is selected from cesium carbonate, potassium hydroxide, very good results are obtained both in terms of reaction yield and product purity. The catalyst may be either the first catalyst or the second catalyst, or both of them may be selected.
Setting the reaction temperature to be 105-145 ℃, setting the reaction retention time to be 12-25min, and setting the flow rate of the mixed solution obtained after mixing by the micro mixer to be 0.5-1.2mL/min, wherein the volume of the micro-structure reactor is 8-20 mL. Preferably, the temperature of the methylation reaction in the present invention is 130 ℃ and the reaction time is 15 min.
And after the reaction is finished, filtering, distilling and collecting a product to obtain the o-aminoanisole. The filtration is performed to recover insoluble substances such as a catalyst, and may be performed by a filtration method and an apparatus which are conventional in the art. And (4) carrying out reduced pressure distillation on the product obtained after the reaction, collecting the product, and analyzing the product.
The distillation can also be rotary distillation, namely distilling the solvent and the dimethyl carbonate at normal pressure, then distilling at reduced pressure, and collecting the fraction with the conditions of 580-610Pa and 130-140 ℃, preferably 600Pa and 130-140 ℃. The process can be carried out using methods and apparatus conventional in the art, such as a rotary evaporator or the like. The reactant dimethyl carbonate of the present invention may be used as a solvent, or dimethyl sulfoxide may be used as a solvent.
Example 1
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, a phase transfer catalyst tetrabutylammonium bromide (TBAB) (10mmol) is placed in a raw material storage tank 2, and then DMC is added to dilute to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 17min at 105 ℃, the flow rate of the mixed solution is 0.8mL/min, and the volume of the micro-structure reactor is 13.5 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 99% and the yield is 93%.
Example 2
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, a phase transfer catalyst tetramethylammonium chloride (10mmol) is placed in a raw material storage tank 2, and then DMC is added to dilute to 40 ml. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 10min at 130 ℃, the flow rate of the mixed solution is 2mL/min, and the volume of the micro-structure reactor is 20 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 97 percent and the yield is 90 percent.
Example 3
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and a phase transfer catalyst, namely tetramethylammonium bromide (10mmol), is placed in a raw material storage tank 2, and then DMC is added to dilute the solution to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 10min at 145 ℃, the flow rate of the mixed solution is 1.2mL/min, and the volume of the micro-structure reactor is 12 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing the product to obtain the anthranilic ether with the conversion rate of more than 98% and the yield of 91%.
Example 4
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and an alkali catalyst sodium carbonate (10mmol) is placed in a raw material storage tank 2 and then DMC is added to dilute to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 20min at 125 ℃, the flow rate of the mixed solution is 0.5mL/min, and the volume of the micro-structure reactor is 10 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 95% and the yield is 88%.
Example 5
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and a base catalyst triethylamine (10mmol) is placed in a raw material storage tank 2 and then DMC is added to dilute to 40 ml. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 15min at 110 ℃, the flow rate of the mixed solution is 1.0mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 98% and the yield is 89%.
Example 6
Ortho-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and an alkali catalyst cesium carbonate (10mmol) is placed in a raw material storage tank 2 and then DMC is added to dilute to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 12min at 140 ℃, the flow rate of the mixed solution is 1.0mL/min, and the volume of the micro-structure reactor is 12 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 98% and the yield is 89%.
Example 7
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and an alkali catalyst potassium hydroxide (10mmol) is placed in a raw material storage tank 2 and then DMC is added to dilute to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 18min at 130 ℃, the flow rate of the mixed solution is 0.8mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing the product to obtain the anthranilic ether with the conversion rate of more than 99% and the yield of 89%.
Example 8
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol), and the solution is placed in a raw material storage tank 1, a phase transfer catalyst tetrabutylammonium bromide (10mmol) is placed in a raw material storage tank 2, and then DMSO is added to dilute the solution to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 20min at the temperature of 110 ℃, the flow rate of the mixed solution is 0.7mL/min, and the volume of the micro-structure reactor is 14 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 96 percent and the yield is 82 percent.
Example 9
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and a phase transfer catalyst, namely tetramethylammonium bromide (10mmol), is placed in a raw material storage tank 2, and then DMSO is added to dilute the solution to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 15min at 115 ℃, the flow rate of the mixed solution is 0.6mL/min, and the volume of the micro-structure reactor is 9 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 96 percent and the yield is 80 percent.
Example 10
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol), and is placed in a raw material storage tank 1, and an alkali catalyst sodium carbonate (10mmol) is placed in a raw material storage tank 2, and then DMSO is added to dilute to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 18min at 125 ℃, the flow rate of the mixed solution is 0.8mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 97 percent and the yield is 82 percent.
Example 11
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol) and placed in a raw material storage tank 1, and a base catalyst triethylamine (10mmol) is placed in a raw material storage tank 2 and then DMSO is added to dilute the raw material storage tank to 40 ml. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 18min at 130 ℃, the flow rate of the mixed solution is 1.0mL/min, and the volume of the micro-structure reactor is 18 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 99% and the yield is 83%.
Example 12
O-aminophenol (0.1mol) was dissolved in 45ml dimethyl carbonate (0.5mol) and placed in raw material storage tank 1, and base catalyst cesium carbonate (10mmol) was placed in raw material storage tank 2 and then diluted to 40ml by adding DMSO. The mixture is fully mixed by a micro-structure mixer and then injected into a micro-structure reactor of a micro-channel modular reaction device, the mixture stays for 18min at 130 ℃, the flow rate of the mixed solution is 0.8mL/min, and the volume of the micro-structure reactor is 15 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the o-aminoanisole is more than 98% and the yield is 80%.
Example 13
O-aminophenol (0.1mol) is dissolved in 45ml dimethyl carbonate (0.5mol), and is placed in a raw material storage tank 1, and an alkali catalyst potassium hydroxide (10mmol) is placed in a raw material storage tank 2, and then DMSO is added to dilute to 40 ml. Fully mixed by a micro-structure mixer, injected into a micro-structure reactor of a micro-channel modular reaction device, and stays for 20min at 130 ℃, the flow rate of the mixed solution is 0.8mL/min, and the volume of the micro-structure reactor is 16 mL. And (3) introducing a discharge port of the microstructure reactor into a product collector, and analyzing a product to obtain that the conversion rate of the anthranilic ether is more than 98% and the yield is 81%.
In general chemical reactions, the role of the solvent is not prominent. However, in the present invention, based on the disclosure of the above examples, the inventors have found that in the methylation reaction of the present invention, the solvent greatly affects the yield of the reaction product, and that other reaction conditions also have a certain effect on the yield of the reaction. On the basis, the inventor obtains the preparation method of the o-aminoanisole, which has higher yield, product purity and dimethyl carbonate utilization rate and is suitable for industrial production.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (5)
1. A method for preparing o-aminoanisole by adopting a micro-flow field reaction technology is characterized by comprising the following steps: the method comprises the following steps:
(1) mixing o-aminophenol and dimethyl carbonate to obtain a mixed system for later use;
(2) preparing a mixed solution of a catalyst and a solvent according to a certain proportion for later use; the catalyst comprises a first catalyst phase transfer catalyst and a second catalyst which is an alkaline catalyst or a metal catalyst, wherein the phase transfer catalyst is tetramethylammonium chloride, tetramethylammonium bromide or tetrabutylammonium bromide, the second catalyst is sodium carbonate, potassium hydroxide, sodium hydroxide or cesium carbonate, and the first catalyst and/or the second catalyst is/are selected during reaction;
(3) carrying out reaction on the prepared two mixed solutions at a certain temperature for a certain time by a micro-channel modular reaction device;
(4) and filtering and distilling the product obtained after the reaction, collecting the product, and analyzing the product.
2. The process for producing anthranilic ether according to claim 1, characterized in that: in the step (2), the solvent is dimethyl carbonate.
3. The process for producing anthranilic ether according to claim 2, characterized in that: ortho-aminophenol in the reaction: dimethyl carbonate: the molar ratio of the catalyst is 1: 10-25: 0.05 to 0.3.
4. The process for producing anthranilic ether according to claim 1, characterized in that: the microchannel modular reaction device comprises a raw material storage tank, a micromixer, a microstructure reactor and a product collector which are sequentially connected through pipelines, wherein the raw material storage tank is provided with a plurality of groups; the reaction temperature is set to be 105-145 ℃, the reaction residence time is 12-25min, the flow rate of the mixed solution obtained after mixing by the micro mixer is 0.5-1.2mL/min, and the volume of the micro-structure reactor is 8-20 mL.
5. The method for preparing anthranilic ether as claimed in claim 1, wherein the distillation comprises distilling off the solvent and dimethyl carbonate under normal pressure, and then distilling under reduced pressure, and collecting the fraction under 580-610Pa and 130-140 ℃.
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