CN114685273A - Preparation method of ethylene glycol phenyl ether acetate - Google Patents
Preparation method of ethylene glycol phenyl ether acetate Download PDFInfo
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- CN114685273A CN114685273A CN202210451903.6A CN202210451903A CN114685273A CN 114685273 A CN114685273 A CN 114685273A CN 202210451903 A CN202210451903 A CN 202210451903A CN 114685273 A CN114685273 A CN 114685273A
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- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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Abstract
The invention relates to a preparation method of ethylene glycol phenyl ether acetate, which comprises the following steps: mixing ethylene glycol phenyl ether, acetic anhydride and molybdenum disulfide, and reacting for 0.5-4 hours under stirring and heat preservation; filtering, decompressing, rectifying and purifying the mixture obtained by the reaction to obtain the ethylene glycol phenyl ether acetate. The preparation method has the characteristics of no harm of reactants to equipment, low price and easy obtainment of reaction raw materials, stable reaction process and high product yield.
Description
Technical Field
The invention relates to the field of fine chemical engineering, and particularly relates to a preparation method of ethylene glycol phenyl ether acetate.
Background
The ethylene glycol phenyl ether acetate is colorless transparent liquid, has pleasant flower and fruit fragrance, is dissolved in alcohol, ether, ester, benzene, hydrocarbon and the like, has no toxicity to people and livestock, and belongs to a green environment-friendly product. The product is a bifunctional high-grade industrial solvent, has better dissolving performance than glycol ether, propylene glycol ether and a general solvent, can be used as an excellent solvent for various high polymer materials, and can greatly improve the product performance when being used in coating, printing ink and adhesives; the product has high boiling point and moderate evaporation rate, can make the paint have slow drying characteristic, is more suitable for color paint and emulsion paint, can be used as an auxiliary solvent of baking paint in the automobile and household appliance industries, can obviously improve the performance of the baking paint, can be used as a solvent of a textile dyeing and finishing auxiliary agent in the textile printing and dyeing industry, and is suitable for printing and dyeing processing by a transfer printing method; the product can be used as raw material to prepare a series of chemical products, such as photosensitizer, photopolymerization initiator, liquid crystal orientation agent, insect repellent, etc., and can also be used as film assistant, anthraquinone dye dispersant, plasticizer, etc.
The ethylene glycol phenyl ether acetate is generally obtained by performing esterification reaction on ethylene glycol phenyl ether and acetic acid under catalysis. The alkyd esterification reaction usually uses strong inorganic acid such as concentrated sulfuric acid as a catalyst, and the concentrated sulfuric acid also has dehydration property and can absorb water generated in the esterification reaction to promote the forward progress of the reaction. However, the concentrated sulfuric acid as the catalyst has the following disadvantages: after the reaction is finished, the sulfuric acid is removed by neutralization, washing and other operations, so that the process route is long, the product loss is easily caused, and the yield is influenced; the strong oxidizing property and the dehydrating property of concentrated sulfuric acid can cause a series of side reactions, so that a small amount of unsaturated compounds, sulfuric esters, carbonyl compounds and the like are often accompanied in reaction products; the strong oxidizing property of the concentrated sulfuric acid can also seriously corrode reaction equipment, so that the production cost is increased; acid waste water generated by post-treatment is not suitable for discharge, and water body pollution is easy to cause.
Aiming at the problems, people adopt heterogeneous catalysts such as metal oxides, ion exchange resins, molecular sieves and the like to catalyze the reaction, the reaction conversion rate is good, the heterogeneous catalysts are easy to separate from a reaction system, and a complex process is not needed to remove the catalysts after the reaction is finished, so that the production cost is reduced, the product loss is reduced, and the yield is further improved. However, heterogeneous catalysts have the disadvantage of slow reaction rates, and the reaction times are generally from 8 to 24 hours.
Disclosure of Invention
In view of the above, a need exists for a method for preparing ethylene glycol phenyl ether acetate, which uses molybdenum disulfide as a catalyst, and has a fast reaction speed and a high yield.
In order to realize the aim, the invention provides a method for preparing ethylene glycol phenyl ether acetate,
the reaction is as follows:
a preparation method of ethylene glycol phenyl ether acetate comprises the following steps:
mixing ethylene glycol phenyl ether, acetic anhydride and molybdenum disulfide, and keeping the temperature for reaction for 0.5 to 4 hours under stirring;
filtering, decompressing, rectifying and purifying the mixture obtained by the reaction to obtain the ethylene glycol phenyl ether acetate.
Furthermore, in the step I, the adding amount of the molybdenum disulfide accounts for 1-6% of the mass of the ethylene glycol phenyl ether.
Preferably, the adding amount of the molybdenum disulfide is 3 percent of the mass of the glycol phenyl ether.
Further, the temperature of the heat preservation reaction in the step (i) is controlled to be 100-120 ℃.
Preferably, the temperature of the heat preservation reaction in the step (i) is controlled to be 110-115 ℃.
Furthermore, the feeding molar ratio of the ethylene glycol phenyl ether to the acetic anhydride in the step (i) is 1: 1.01-1.1.
Preferably, the feeding molar ratio of the ethylene glycol phenyl ether to the acetic anhydride in the step (I) is 1: 1.03-1.06.
Further, the reaction time was kept for 4 hours under stirring in the step (i).
Further, in the step two, the pressure of the vacuum distillation is 1KPa, and the temperature of the target product extracted in the vacuum distillation is 120-130 ℃.
Preferably, the temperature of the target product extracted in the reduced pressure rectification in the step II is 120-125 ℃.
Compared with the prior art, the invention has the advantages that:
according to the invention, the ethylene glycol phenyl ether and acetic anhydride react under the catalysis of molybdenum disulfide to generate the ethylene glycol phenyl ether acetate, so that the problem that water generated in the traditional alcohol acid esterification reaction needs to be continuously removed is avoided; because the catalyst molybdenum disulfide is solid, the catalyst molybdenum disulfide is easy to separate from reaction liquid, and complex post-treatment operation is not needed; the reaction condition is mild, the reaction raw materials are cheap and easy to obtain, the equipment is friendly, the reaction result is stable, and the product yield is high.
Detailed Description
The ethylene glycol phenyl ether acetate is generally obtained by performing esterification reaction on ethylene glycol phenyl ether and acetic acid under catalysis. In order to avoid the defects brought by concentrated sulfuric acid as a catalyst, the alkyd esterification reaction is catalyzed by adopting a heterogeneous catalyst such as metal oxide, ion exchange resin, molecular sieve and the like, although the reaction has better conversion rate, the production cost is reduced, the product loss is reduced, and the yield is further improved. However, heterogeneous catalysts have the disadvantage of a slow reaction rate. Therefore, it is necessary to develop a method for esterification reaction, which has the advantages of friendly raw materials to environment and equipment, simple process route, high catalytic activity of the catalyst and easy separation. The invention provides a preparation method of ethylene glycol phenyl ether acetate, which comprises the steps of mixing ethylene glycol phenyl ether, acetic anhydride and catalyst molybdenum disulfide, carrying out esterification reaction, filtering the solution after the reaction, and carrying out reduced pressure rectification treatment to obtain the ethylene glycol phenyl ether acetate with higher purity. The reaction route of the method is as follows:
in order to further illustrate the present invention, the following examples are provided to describe the preparation method of ethylene glycol phenyl ether acetate according to the present invention in detail.
The sources of the raw materials used in the present invention are not limited, and the raw materials used in the present invention are all those commonly available in the art unless otherwise specified.
Example 1
Influence of different raw material molar ratios on the reaction results:
550g of ethylene glycol phenyl ether, acetic anhydride with different mass and 16.5g of molybdenum disulfide are respectively put into a glass reaction kettle, stirring is started, the temperature is raised, and when the temperature is raised to be more than 110 ℃, the heat preservation reaction is started for 4 hours. Cooling the reacted liquid to room temperature, filtering to remove the catalyst, transferring the reaction liquid to a rectifying tower for rectification under reduced pressure, wherein the rectification pressure is 1KPa, collecting the components with the temperature of 120-125 ℃ as products, and performing gas chromatography analysis.
TABLE 1 Effect of the reaction on the molar ratio of the different starting materials
| Serial number | Ethylene glycol phenyl ether: acetic anhydride | Yield/% | Purity/%) |
| 1 | 1:1.01 | 89.54 | 95.32 |
| 2 | 1:1.03 | 93.65 | 97.85 |
| 3 | 1:1.06 | 94.12 | 98.74 |
| 4 | 1:1.08 | 93.33 | 97.64 |
| 5 | 1:1.10 | 93.46 | 97.51 |
The experimental results show that: under the same condition, the yield and purity of the product are improved by properly increasing the dosage of the acetic anhydride (the molar ratio is 1:1.06), and the dosage of the acetic anhydride is not obviously improved by further increasing.
Example 2
Effect of different catalyst additions on the reaction results:
respectively putting 550g of ethylene glycol phenyl ether, 408g of acetic anhydride and molybdenum disulfide with different masses into a glass reaction kettle, starting stirring and heating, and starting heat preservation reaction for 4 hours when the temperature is raised to be more than 110 ℃. Cooling the reacted liquid to room temperature, filtering to remove the catalyst, transferring the reaction liquid to a rectifying tower for rectification under reduced pressure, wherein the rectification pressure is 1KPa, collecting the components with the temperature of 120-125 ℃ as products, and performing gas chromatography analysis.
TABLE 2 reaction Effect of different catalyst additions
The experimental results show that: under the same conditions, the product yield is increased along with the increase of the adding amount of the catalyst, and when the catalyst is added to more than 3 percent of the mass of the ethylene glycol phenyl ether, the yield is not obviously increased.
Example 3
Effect of different reaction temperatures on the reaction results:
550g of ethylene glycol phenyl ether, 408g of acetic anhydride and 16.5g of molybdenum disulfide are respectively put into a glass reaction kettle, stirred and heated, and heated to different temperatures for reaction for 4 hours. Cooling the reacted liquid to room temperature, filtering to remove the catalyst, transferring the reaction liquid to a rectifying tower for rectification under reduced pressure, wherein the rectification pressure is 1KPa, collecting the components with the temperature of 120-125 ℃ as products, and performing gas chromatography analysis.
TABLE 3 Effect of the reaction at different reaction temperatures
| Serial number | Reaction temperature/. degree.C | Yield/% | Purity/%) |
| 1 | 80 | 60.30 | 82.50 |
| 2 | 100 | 88.28 | 94.83 |
| 3 | 110 | 94.12 | 98.74 |
| 4 | 115 | 94.30 | 98.47 |
| 5 | 120 | 93.85 | 97.61 |
The experimental results show that: the higher the reaction temperature, the faster the reaction rate. When the reaction temperature is low, the reaction rate is low, the reaction is difficult to complete in a short time, and unreacted raw materials are difficult to remove in subsequent separation and purification, so that the purity is influenced. When the temperature is increased to 110-115 ℃, the reaction effect is better.
Example 4
Influence of different incubation times on the reaction results:
respectively putting 550g of ethylene glycol phenyl ether, 408g of acetic anhydride and 16.5g of molybdenum disulfide into a glass reaction kettle, starting stirring, heating, raising the temperature to 110 ℃, and carrying out heat preservation reaction for different times. Cooling the reacted liquid to room temperature, filtering to remove the catalyst, transferring the reaction liquid to a rectifying tower for rectification under reduced pressure, wherein the rectification pressure is 1KPa, collecting the components with the temperature of 120-125 ℃ as products, and performing gas chromatography analysis.
TABLE 5 reaction Effect of different incubation times
| Serial number | Holding time/h | Yield/% | Purity/%) |
| 1 | 0.5 | 54.68 | 72.47 |
| 2 | 1.0 | 85.59 | 91.13 |
| 3 | 2.0 | 89.30 | 93.46 |
| 4 | 3.0 | 92.51 | 96.73 |
| 5 | 4.0 | 94.12 | 98.74 |
| 6 | 5.0 | 93.86 | 98.53 |
The experimental results show that: when the heat preservation time is short, more reactants are not reacted, the yield and the purity are influenced, the reaction effect gradually becomes good along with the extension of the heat preservation time, the yield and the purity are higher when the heat preservation is carried out for 4 hours, and the heat preservation is continued to 5 hours without obvious improvement.
Example 5
The preparation method of ethylene glycol phenyl ether acetate includes the following steps:
550g of ethylene glycol phenyl ether, 408g of acetic anhydride and 16.5g of molybdenum disulfide are put into a glass reaction kettle to be mixed, stirring is started, the temperature is raised, and when the temperature is raised to be higher than 110 ℃, the heat preservation reaction is started for 4 hours.
Cooling the reacted liquid to room temperature, filtering to remove molybdenum disulfide, transferring the reacted liquid to a rectifying tower, carrying out reduced pressure rectification and purification, wherein the rectification pressure is 1KPa, and collecting the components at the temperature of 120 ℃, namely the ethylene glycol phenyl ether acetate.
The invention adopts molybdenum disulfide as a catalyst, and because the molybdenum disulfide crystal has a two-dimensional layered structure and a larger specific surface area, the molybdenum disulfide crystal can be fully contacted with reactants, the catalytic effect is good, and the purity of the prepared product is good. The method can separate the catalyst from the reaction liquid by only one step of suction filtration, and has the characteristic of easy separation. The method has high reaction rate and reaction time of only 4 hours.
The preparation method has the characteristics of no harm of reactants to equipment, low price and easy obtainment of reaction raw materials, stable reaction process, high product yield and simple operation.
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 present 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 (10)
1. A preparation method of ethylene glycol phenyl ether acetate is characterized by comprising the following steps: the method comprises the following steps:
mixing ethylene glycol phenyl ether, acetic anhydride and molybdenum disulfide, and reacting for 0.5-4 hours under stirring and heat preservation;
filtering, decompressing, rectifying and purifying the mixture obtained by the reaction to obtain the ethylene glycol phenyl ether acetate.
2. The method for preparing ethylene glycol phenyl ether acetate according to claim 1, wherein:
in the step I, the adding amount of the molybdenum disulfide accounts for 1-6% of the mass of the ethylene glycol phenyl ether.
3. The method for preparing ethylene glycol phenyl ether acetate according to claim 2, wherein: the adding amount of the molybdenum disulfide is 3 percent of the mass of the ethylene glycol phenyl ether.
4. The method for preparing ethylene glycol phenyl ether acetate according to claim 1, wherein:
the temperature of the heat preservation reaction in the step (I) is controlled to be 100-120 ℃.
5. The method for preparing ethylene glycol phenyl ether acetate according to claim 4, wherein:
the temperature of the heat preservation reaction in the step (i) is controlled to be 110-115 ℃.
6. The method for preparing ethylene glycol phenyl ether acetate according to claim 1, wherein:
in the step I, the feeding molar ratio of the ethylene glycol phenyl ether to the acetic anhydride is 1: 1.01-1.1.
7. The method for preparing ethylene glycol phenyl ether acetate according to claim 6, wherein:
in the step I, the feeding molar ratio of the ethylene glycol phenyl ether to the acetic anhydride is 1: 1.03-1.06.
8. The method for preparing ethylene glycol phenyl ether acetate according to claim 1, wherein:
the reaction time is 4 hours under stirring and heat preservation.
9. The method for preparing ethylene glycol phenyl ether acetate according to claim 1, wherein:
in the second step, the pressure of the vacuum rectification is 1KPa, and the temperature of the target product extracted in the vacuum rectification is 120-130 ℃.
10. The method for preparing ethylene glycol phenyl ether acetate according to claim 9, wherein:
in the step two, the temperature for extracting the target product in the reduced pressure distillation is 120-125 ℃.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1187234A (en) * | 1967-11-20 | 1970-04-08 | Exxon Research Engineering Co | Conversion of Acids or Anhydrides to Alcohols |
| CN101475469A (en) * | 2009-01-20 | 2009-07-08 | 南京林业大学 | Method for synthesizing diatomic alcohol ether acid ester |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1187234A (en) * | 1967-11-20 | 1970-04-08 | Exxon Research Engineering Co | Conversion of Acids or Anhydrides to Alcohols |
| CN101475469A (en) * | 2009-01-20 | 2009-07-08 | 南京林业大学 | Method for synthesizing diatomic alcohol ether acid ester |
Non-Patent Citations (2)
| Title |
|---|
| 孙浩波: "酸酐酯化新型催化剂研究", 中国优秀硕士学位论文全文数据库 工程科技I辑 * |
| 朱绍先,李延鹏,黄化民: "合成C_1～C_(10)脂肪族羧酸2-苯氧乙酯的新方法", 吉林大学学报(理学版) * |
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