CN113248370A - Preparation method of o-methyl sodium phenoxyacetate in synthesis process of 2-methyl-4-sodium phenoxyacetate - Google Patents
Preparation method of o-methyl sodium phenoxyacetate in synthesis process of 2-methyl-4-sodium phenoxyacetate Download PDFInfo
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Abstract
A preparation method of o-methyl sodium phenoxyacetate in the synthesis process of 2-methyl-4-sodium phenoxyacetate. The invention provides a preparation method of sodium o-tolyloxy acetate, which comprises the steps of firstly reacting o-cresol with sodium hydroxide to prepare an o-cresol sodium solution, then reacting chloroacetic acid with sodium hydroxide to prepare a sodium chloroacetate solution, and finally reacting the o-cresol sodium with the sodium chloroacetate under the condition of adding a catalyst to prepare the sodium o-tolyloxy acetate. According to the invention, the catalyst is added in the preparation process, so that the reaction temperature and the decomposition rate of sodium chloroacetate can be effectively reduced, the conversion rate of o-cresol is improved, the problems of difficult treatment and high energy consumption of phenol-containing wastewater in the later period due to low conversion rate of o-cresol are solved, the preparation process is effectively simplified, and the purity and the yield of the o-tolyloxy sodium acetate prepared by the preparation method are high.
Description
Technical Field
The invention relates to improvement of a chemical synthesis process, in particular to a preparation method of sodium o-tolyloxy acetate in a synthesis process of 2-methyl-4-sodium chlorophenoxyacetate.
Background
Sodium 2-methyl-4-chlorophenoxyacetate is one of the basic varieties of herbicide, and is still the basic variety of herbicide up to now. The 2-methyl-4-chlorophenoxy sodium acetate is a phenoxyacetic acid selective systemic transduction hormone herbicide, can destroy the persuasive tissue of dicotyledon, and leads the growth and development of the plant to be interfered. The sodium 2-methyl-4-chlorophenoxyacetate has the characteristics of high efficiency, low toxicity, low residue, no environmental pollution and the like, thereby being widely applied and greatly demanded. The 2-methyl-4-chlorophenoxyacetic acid sodium salt is not only a hormone herbicide, but also a plant growth regulator, and is an important intermediate for pesticide and medicine synthesis.
The preparation process of the 2-methyl-4-sodium chlorophenoxyacetate mainly comprises two processes, wherein one process is chlorination and then condensation, and the other process is condensation and then chlorination. Wherein the condensation reaction process refers to the process of preparing the sodium o-tolyloxy acetate by condensing the sodium o-cresol and the sodium chloroacetate, and the sodium o-tolyloxy acetate is an important intermediate for preparing the 2-methyl-4-sodium chlorophenoxyacetate.
In the prior art, the preparation process of the sodium o-tolyloxy acetate comprises the following steps: o-cresol, a certain amount of water and sodium hydroxide are put into a reaction kettle to generate o-cresol sodium. Dropping sodium hydroxide into chloroacetic acid and water at low temperature to generate sodium chloroacetate, then heating the o-cresol sodium to reflux state, dropping sodium chloroacetate, and reacting to generate o-methyl sodium phenoxyacetate.
Because the reaction temperature is high, partial decomposition is caused in the chloroacetic acid reaction process, but the reaction effect is influenced by reducing the temperature, so that the reaction of the raw material o-cresol is incomplete, the o-cresol conversion rate is only 85 percent, and the defects of steam heating, high energy consumption and the like are also caused.
Meanwhile, o-cresol is remained in the product, water is added for heating, dephenolization treatment is carried out, a large amount of phenol-containing wastewater generated in the dephenolization process is difficult to treat and needs to be further recovered and treated, macroporous resin is required for adsorption in the treatment of the phenol-containing wastewater, and alkali desorption is used for recovery and reutilization, so that the recovery process is complicated, the effect is not ideal, the environmental protection pressure is high, a large amount of steam is consumed in the dephenolization process, and the energy consumption is high.
In view of the above problems, it is desirable to provide a method for preparing sodium o-tolyloxy acetate, which has high conversion rate of raw materials, low energy consumption and environmental protection.
Disclosure of Invention
Based on the above technical background, the present inventors have made a keen search and, as a result, have found that: the catalyst, especially the composite catalyst with a specific proportion, is added, so that the reaction temperature and the decomposition rate of sodium chloroacetate can be reduced, the selectivity and the conversion rate of o-cresol are improved, the reaction rate, the yield and the purity of o-methyl sodium phenoxyacetate are further improved, and meanwhile, because the conversion rate of o-cresol is improved, dephenolization treatment is omitted, the problems of difficult treatment of phenol-containing wastewater and high energy consumption are solved, and the method has the characteristics of environmental protection.
The invention provides a preparation method of sodium o-tolyloxy acetate, which comprises the following steps:
and 3, under the condition of adding the catalyst, dropwise adding the sodium chloroacetate solution into the o-cresol sodium solution for reaction to obtain the o-methyl sodium phenoxyacetate.
The preparation method of the o-methyl sodium phenoxyacetate provided by the invention has the following advantages:
(1) according to the preparation method of the sodium o-tolyloxy acetate, the reaction temperature is reduced by adding the catalyst, so that the decomposition rate of sodium chloroacetate is reduced, and the selectivity and the conversion rate of o-cresol are improved;
(2) the preparation method disclosed by the invention does not need dephenolization treatment, avoids further recovery and treatment of wastewater in the dephenolization process, reduces energy consumption, and has the excellent characteristics of environmental friendliness;
(3) the reaction in the step 1 and the step 3 is carried out in the reaction kettle with the heat-preservation cotton arranged in the jacket, the device has good heat-insulation effect, the heat released by the reaction is not easy to dissipate, additional heating is not needed, the heat released by the reaction can just keep the reaction, and the energy consumption is effectively reduced.
Drawings
FIG. 1 shows a gas chromatogram of the product obtained in example 1 of the present invention;
FIG. 2 shows a gas chromatogram of the product obtained in example 2 of the present invention;
FIG. 3 shows a gas chromatogram of the product obtained in example 3 of the present invention;
FIG. 4 shows a gas chromatogram of the product obtained in example 4 of the present invention;
FIG. 5 shows a gas chromatogram of the product obtained in example 5 of the present invention;
FIG. 6 shows a gas chromatogram of the product obtained in example 6 of the present invention;
FIG. 7 shows a gas chromatogram of the product obtained in comparative example 1 of the present invention.
Detailed Description
The present invention will be described in detail below, and features and advantages of the present invention will become more apparent and apparent with reference to the following description.
The invention provides a preparation method of sodium o-tolyloxy acetate, which comprises the following steps:
and 3, under the condition of adding the catalyst, dropwise adding the sodium chloroacetate solution into the o-cresol sodium solution for reaction to obtain the o-methyl sodium phenoxyacetate.
This step is specifically described and illustrated below.
In the step 1 of the invention, sodium hydroxide is firstly added into a reaction kettle, and then o-cresol is added into the reaction kettle, the reaction kettle is a heat-preservation reaction kettle with a jacket, and heat-preservation cotton is arranged in the jacket, so that the heat-preservation reaction kettle has an excellent heat-insulation effect. The o-cresol and the sodium hydroxide solution are reacted in the reaction kettle without heating, the heat released by the reaction can maintain the reaction, and the energy consumption is effectively reduced.
The o-cresol is preferably added in batches, and the o-cresol can be reacted more completely and the conversion rate is higher by the batch addition mode. The problems of difficult treatment and large energy consumption of the phenol-containing wastewater in the later period are avoided.
The concentration of the sodium hydroxide solution is 20-40%, preferably the concentration of the sodium hydroxide solution is 25-35%, and more preferably the concentration of the sodium hydroxide solution is 30%.
Tests show that the concentration of the sodium hydroxide solution is too high, crystallization is easy to cause, and if the concentration of the sodium hydroxide solution is too low, the reaction rate is too low, and the reaction efficiency is low.
According to the invention, the mass ratio of o-cresol to sodium hydroxide is 1: (0.9-2), preferably 1: (1 to 1.5), more preferably 1 (1.1 to 1.3).
The reaction temperature is 60-100 ℃, preferably 70-90 ℃, and more preferably 75-85 ℃.
The reaction temperature is too low, the o-cresol reaction is incomplete, the o-cresol conversion rate is reduced, raw material waste and reaction yield are reduced, and phenol-containing wastewater in the later period is difficult to treat and the preparation energy consumption is increased.
The reaction time is 0.5-2 h, preferably 1-1.5 h, and more preferably 1 h.
And 2, reacting chloroacetic acid with a sodium hydroxide solution to obtain a sodium chloroacetate solution.
The reaction for generating the sodium chloroacetate in the step 2 is carried out in a heat-preservation reaction kettle with a jacket, and frozen saline is introduced into the jacket of the reaction kettle to cool the reaction process. The reaction temperature is maintained at 5 to 15 ℃, preferably 7 to 12 ℃, and more preferably 10 ℃. Too high reaction temperature is easy to cause decomposition, which is not beneficial to the preparation of sodium chloroacetate, and too low reaction temperature causes too low reaction speed, which reduces the preparation efficiency.
The reaction time is 2-4h, preferably 3-3.5h, more preferably 3 h.
In step 2 of the present invention, the concentration of the sodium hydroxide solution is 20 to 40%, preferably the concentration of the sodium hydroxide solution is 25 to 35%, and more preferably the concentration of the sodium hydroxide solution is 30%.
The concentration of the sodium hydroxide solution influences the reaction rate and the reaction conversion rate, and the concentration of the sodium hydroxide solution is too high or too low, so that the reaction conversion rate and the reaction rate are not improved, and the inventor finds that the reaction conversion rate and the reaction rate are high when the concentration of the sodium hydroxide solution is 20-40%, particularly 30%.
The mass ratio of sodium chloroacetate to sodium hydroxide is 1: (1 to 3), preferably 1: (1.2 to 2.5), more preferably 1: (1.3-2).
And 3, under the condition of adding the catalyst, dropwise adding the sodium chloroacetate solution into the o-cresol sodium solution for reaction to obtain the o-methyl sodium phenoxyacetate.
The sodium chloroacetate solution is added dropwise, so that the reaction is more complete and the conversion rate of o-cresol is higher.
The dropping rate of the sodium chloroacetate is 200-400kg/h, preferably 250-350kg/h, and more preferably 300 kg/h.
The mol ratio of the sodium chloroacetate to the o-cresol sodium is 1: (1-2), preferably 1: (1.1 to 1.7), more preferably 1: 1.25.
the sodium chloroacetate and the o-cresol sodium are added in the molar ratio range, so that the conversion rate of the o-cresol sodium can be ensured to be more complete, the later treatment of phenol-containing wastewater is avoided, and the preparation process is simplified.
The mass ratio of the catalyst to the o-cresol sodium is (0.5-3): 650, preferably the mass ratio is (1.5-2.5): 650, more preferably in a mass ratio of 2: 650.
Experiments show that high catalytic efficiency can be realized by only adding a small amount of catalyst, and when the mass ratio of the catalyst to the o-cresol sodium is (0.5-3): 650, the conversion rate of the raw material and the yield of the product are both high.
The catalyst is selected from one or more of compounds containing iron, cobalt, nickel, copper and zinc, preferably from one or more of zinc chloride, ferric chloride, cobalt chloride, nickel chloride and copper chloride, more preferably from one or two of zinc chloride and ferric chloride, such as a mixture of ferric chloride and zinc chloride.
The inventor finds that the reaction temperature can be reduced by adding the catalyst in the process of preparing the sodium o-tolyloxyacetate, so that the reaction can be carried out at a lower temperature, the decomposition of chloroacetic acid caused by high temperature is effectively avoided, the conversion rate of o-cresol is improved, the later dephenolization recovery process of phenol-containing wastewater is avoided, the preparation process is simplified, and the yield and the purity of the prepared product are high. In a preferred embodiment, one or more of the chlorides are preferably added as a catalyst, so that the price is low, impurity removal in a post-treatment process can be avoided, the preparation process is simplified, one or two of zinc chloride and ferric trichloride are more preferably adopted as the catalyst, the catalytic effect is better, and the conversion rate and the yield of the o-cresol are higher.
According to a preferred embodiment of the present invention, when the catalyst is a mixture of ferric chloride and zinc chloride, the catalytic effect is better, and the conversion rate of o-cresol and the yield of the prepared product are higher. Wherein the mass ratio of the ferric trichloride to the zinc chloride is (0.1-10): 1, preferably (0.3-5): 1, and more preferably (0.5-3): 1.
The inventor finds that when the mixture of ferric trichloride and zinc chloride in the mass ratio is used as a catalyst for reaction, the conversion rate of raw materials is higher, and the prepared product has higher yield and purity, and particularly, when the mass ratio of ferric trichloride to zinc chloride is 1:1, the prepared product has the highest purity and yield.
The reaction in the step 3 is carried out in a reaction kettle with heat insulation cotton arranged in a jacket, and the heat insulation effect can be good by arranging the heat insulation cotton in the jacket, so that the heat released by the reaction is not easy to dissipate. In the invention, under the action of the catalyst, sodium chloroacetate and o-cresol sodium can react at a lower temperature, and the reaction kettle has good heat insulation effect, so that the heat generated by the reaction of the sodium chloroacetate and the o-cresol sodium in the reaction kettle can just maintain the reaction, the reaction temperature is controlled to be between 80 and 85 ℃, the reaction at the temperature can avoid chloroacetic acid decomposition caused by high temperature, the conversion rate of raw materials is effectively improved, and on the other hand, due to the good heat insulation effect of the reaction kettle, no additional heating is needed for the reaction in the reaction kettle, and the energy consumption is reduced.
In the reaction process, a pH regulator is added to regulate the pH of the reaction system to 7-10, preferably 7.5-9, and more preferably 8. Adjusting the pH value of the reaction system to be alkalescent is not only beneficial to protecting the material of the reactor, but also beneficial to maintaining the stability of the catalyst, ensuring the good catalytic effect of the catalyst in the reaction process and being more beneficial to improving the purity and yield of the product.
The pH regulator is alkali, preferably sodium hydroxide, potassium hydroxide or ammonia water, and more preferably sodium hydroxide.
The preparation method of the o-methyl sodium phenoxyacetate has the advantages that the conversion rate of o-cresol is high and reaches more than 95%, the purity and the yield of the o-methyl sodium phenoxyacetate are high, the purity is 96-99.9%, and the yield is 91-97%.
The invention has the following beneficial effects:
(1) the preparation method has the advantages that the reaction temperature is low, chloroacetic acid cannot be decomposed in the reaction process, in the step 1 and the step 3, the reaction is carried out in the reaction kettle with the jacket, the heat preservation cotton is arranged in the jacket, the good heat insulation effect is achieved, the reaction belongs to exothermic reaction, the heat released in the sodium chloroacetate dropwise adding reaction process is just maintained at the reaction temperature of the system, the reaction can be carried out without extra heating and temperature rise, the heat energy consumption in the reaction process is avoided, and the reaction energy consumption is effectively reduced;
(2) the preparation method of the invention does not reduce the conversion rate of the o-cresol raw material while reducing the reaction temperature by adding the catalyst, and the reaction speed is accelerated;
(3) the preparation method reduces the reaction temperature due to the addition of the catalyst, reduces the decomposition rate of sodium chloroacetate, improves the conversion rate of o-cresol, omits dephenolization treatment, solves the problems of difficult treatment and large energy consumption of phenol-containing wastewater, meets the requirement of environmental protection and reduces the preparation cost, the conversion rate of the o-cresol sodium reaches more than 95 percent, the purity and the yield of the o-tolyloxy sodium acetate are higher, and the purity of the o-tolyloxy sodium acetate is 96 to 99.9 percent;
(4) the preparation method provided by the invention has the advantages of simple preparation method, high raw material conversion rate, high product yield, environmental friendliness and the like.
Examples
The invention is further illustrated by the following specific examples, which are intended to be illustrative only and not limiting to the scope of the invention.
Example 1
Placing 108g of o-cresol and 135g of sodium hydroxide with the mass fraction of 30% in a reaction kettle with a jacket for adiabatic reaction, wherein heat-preservation cotton is arranged in the jacket, the reaction temperature is 80 ℃, and the reaction time is 1h, so as to obtain an o-cresol sodium solution.
113g of chloroacetic acid and 160g of sodium hydroxide with the mass fraction of 30 percent are placed in a heat-preservation reaction kettle with a jacket, frozen saline is introduced into the jacket to maintain the reaction temperature at 10 ℃, and the reaction is carried out for 3 hours, so as to obtain the sodium chloroacetate solution.
Adding 0.2g of catalyst zinc chloride into a reaction kettle with heat-insulating cotton arranged in a jacket, dropwise adding a sodium chloroacetate solution into an o-cresol sodium solution at a dropwise adding rate of 300kg/h, stirring for reaction, controlling the reaction temperature to be 80-85 ℃, adjusting the pH value of a reaction system to be 8, and reacting for 5 hours, wherein the o-cresol content is less than 0.5% at the moment to obtain a solution of o-tolyloxy sodium acetate.
The purity of the o-methyl sodium phenoxyacetate is 99.51 percent, the content of the o-cresol raw material is less than 0.5 percent and the yield is 95.5 percent by gas chromatography.
Example 2
The procedure of example 1 was repeated except that: 0.2g of catalyst iron trichloride was added.
The purity of the o-tolyloxy sodium acetate is 96.2%, the content of the raw material o-cresol is 3.8% and the yield is 91% through gas chromatography.
Example 3
The procedure of example 1 was repeated except that: 0.2g of a mixture of ferric trichloride and zinc chloride in a mass ratio of 2:1 was added as a catalyst.
The purity of the sodium o-tolyloxy acetate was 98.3%, the content of the raw material o-cresol was 1.7%, and the yield was 93% as determined by gas chromatography.
Example 4
The procedure of example 1 was repeated except that: 0.2g of a mixture of ferric trichloride and zinc chloride in a mass ratio of 1:1 was added as a catalyst.
The purity of the sodium o-tolyloxy acetate was 99.62%, the content of the raw material o-cresol was 0.38%, and the yield was 96% as determined by gas chromatography.
Example 5
The procedure of example 1 was repeated except that: 0.2g of a mixture of ferric trichloride and zinc chloride in a mass ratio of 1:2 was added as a catalyst.
The purity of the sodium o-tolyloxy acetate was 98.23%, the content of the raw material o-cresol was 1.77%, and the yield was 93% as determined by gas chromatography.
Example 6
The procedure of example 1 was repeated except that: 0.2g of catalyst copper chloride was added.
The purity of the sodium o-tolyloxy acetate was 96.53%, the content of the raw material o-cresol was 3.47%, and the yield was 92.5% as determined by gas chromatography.
Comparative example
Comparative example 1
The procedure of example 1 was repeated except that: no catalyst is added in the preparation process, and the reaction temperature of the o-cresol sodium and the sodium chloroacetate is 100 ℃.
The purity of the o-tolyloxy sodium acetate is 87.52%, the content of the raw material o-cresol is 12.48%, and the yield is 85% by gas chromatography.
Examples of the experiments
Experimental example 1 gas chromatography analysis
The sodium o-tolyloxyacetate obtained in examples 1 to 5 and comparative examples 1 to 2 was subjected to gas chromatography under the following test conditions: filling: hyper 0DS2C18, flow rate: 1.0mL/min, mobile phase: 60% MeOH, pressure: 10.0Mpa, column length: 250mm, detector: UV 220nm, column diameter: 4.6mm, sample size: 20 μ L. The test results are shown in FIGS. 1 to 7.
As can be seen from FIGS. 1 to 7, the purity of the products prepared in examples 1 to 6 of the present invention is high, the purity is 96% to 99.9%, and the purity of the product prepared in comparative example 1 is 87.52%, which indicates that the purity of the product can be improved by adding the catalyst. By comparing examples 1, 2, 6 and 2 to 4, it is understood that the product purity can be further improved by the composite catalyst of ferric trichloride and zinc chloride.
The invention has been described in detail with reference to specific embodiments and illustrative examples, but the description is not intended to be construed in a limiting sense. Those skilled in the art will appreciate that various equivalent substitutions, modifications or improvements may be made to the technical solution of the present invention and its embodiments without departing from the spirit and scope of the present invention, which fall within the scope of the present invention. The scope of the invention is defined by the appended claims.
Claims (10)
1. A preparation method of sodium o-tolyloxy acetate is characterized by comprising the following steps:
step 1, reacting o-cresol with a sodium hydroxide solution to prepare an o-cresol sodium solution;
step 2, reacting chloroacetic acid with a sodium hydroxide solution to prepare a sodium chloroacetate solution;
and 3, under the condition of adding the catalyst, dropwise adding the sodium chloroacetate solution into the o-cresol sodium solution for reaction to obtain the o-methyl sodium phenoxyacetate.
2. The production method according to claim 1, wherein, in step 1,
the concentration of the sodium hydroxide solution is 20-40%, and the mass ratio of the o-cresol to the sodium hydroxide is 1: (0.9-2).
3. The production method according to claim 1, wherein, in step 1,
the reaction is carried out in a heat-preservation reaction kettle with a jacket, heat-preservation cotton is arranged in the jacket, the reaction temperature is 60-100 ℃, and the reaction time is 0.5-2 h.
4. The production method according to claim 1, wherein, in step 2,
the mass ratio of sodium chloroacetate to sodium hydroxide is 1: (1-3).
5. The production method according to claim 1, wherein, in step 2,
the reaction is carried out in a reaction kettle with a jacket, frozen saline is introduced into the jacket, the reaction temperature is 5-15 ℃, and the reaction time is 2-4 hours.
6. The production method according to claim 1, wherein, in step 3,
the mass ratio of the catalyst to the o-cresol sodium is (0.5-3): 650.
7. The production method according to claim 1, wherein, in step 3,
the catalyst is selected from one or more of compounds containing iron, cobalt, nickel, copper and zinc, preferably selected from one or more of zinc chloride, ferric trichloride, cobalt chloride, nickel chloride and copper chloride, and more preferably selected from one or two of zinc chloride and ferric trichloride.
8. The production method according to claim 7, wherein, in step 3,
when the adopted catalyst is a mixture of ferric trichloride and zinc chloride, the mass ratio of the ferric trichloride to the zinc chloride is (0.1-10): 1.
9. The production method according to claim 1, wherein, in step 3,
the reaction is carried out in a reaction kettle with heat-preservation cotton arranged in a jacket, and the reaction temperature is maintained at 80-85 ℃ without heating.
10. The production method according to claim 1,
the preparation method has the advantages that the conversion rate of o-cresol is more than 95 percent, the purity of the prepared o-tolyloxy sodium acetate is 96 to 99.9 percent, and the yield is 91 to 97 percent.
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| CN113788750A (en) * | 2021-10-27 | 2021-12-14 | 安庆朗坤药业有限公司 | Preparation method of sodium phenoxyacetate |
| CN114685264A (en) * | 2022-05-06 | 2022-07-01 | 山东潍坊润丰化工股份有限公司 | A kind of preparation method of high-quality 2-methyl-4-chlorophenoxyacetic acid |
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| CN113788750A (en) * | 2021-10-27 | 2021-12-14 | 安庆朗坤药业有限公司 | Preparation method of sodium phenoxyacetate |
| CN113788750B (en) * | 2021-10-27 | 2024-04-16 | 安庆朗坤药业有限公司 | Preparation method of sodium phenoxyacetate |
| CN114685264A (en) * | 2022-05-06 | 2022-07-01 | 山东潍坊润丰化工股份有限公司 | A kind of preparation method of high-quality 2-methyl-4-chlorophenoxyacetic acid |
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