KR20240085155A - Method of manufacturing 3-butene-1,2-diol compounds - Google Patents

Abstract

According to embodiments of the present disclosure, a premixture containing water, an acidic compound, 2-butene-1,4-diol, and copper(I) catalyst is heated to form 3-butene-1,2-diol and divinyldiol. High purity 3-butene-1,2-diol can be obtained by preparing a reaction mixture containing oxane and separating 3-butene-1,2-diol from the reaction mixture. Therefore, a method for producing 3-butene-1,2-diol with improved yield and purity can be provided.

Description

Method for producing 3-butene-1,2-diol {METHOD OF MANUFACTURING 3-BUTENE-1,2-DIOL COMPOUNDS}

The present disclosure relates to a process for preparing 3-butene-1,2-diol.

Secondary batteries are batteries that can be repeatedly charged and discharged, and have been widely applied to portable electronic communication devices such as camcorders, mobile phones, and laptop PCs with the development of the information and communication and display industries. Examples of secondary batteries include lithium secondary batteries, nickel-cadmium batteries, and nickel-hydrogen batteries. Among these, lithium secondary batteries have high operating voltage and energy density per unit weight, and are advantageous for charging speed and weight reduction. It has been actively developed and applied in this regard.

A lithium secondary battery may include, for example, an electrode assembly including a positive electrode, a negative electrode, and a separator, and an electrolyte solution impregnating the electrode assembly. The electrolyte may react with the anode and cathode due to the charging and discharging behavior of the secondary battery, and the electrolyte may be consumed or depleted. Accordingly, the capacity and lifespan of the secondary battery may decrease, and the electrolyte solution is required to have high ionic conductivity and chemical stability.

Therefore, electrolyte additives can be used to improve the structural stability of the lithium secondary battery and prevent side reactions between the electrolyte and the electrode and depletion of the electrolyte.

As a raw material for producing the electrolyte additives, 3-butene-1,2-diol can be used. However, due to the high production cost and low yield of 3-butene-1,2-diol, the economic feasibility and fairness of the manufacturing process may be reduced. Additionally, the purity of 3-butene-1,2-diol may decrease due to side reactions that occur during the manufacturing process, and the quality of electrolyte additives may also decrease.

For example, Korean Patent Publication No. 10-2022-0133684 is a document regarding a compound, a non-aqueous electrolyte containing the same, and a lithium secondary battery containing the same, and describes a method of synthesizing the compound using 3-butene-1,2-diol. It is starting.

Korean Patent Publication No. 10-2022-0133684

One object of the present disclosure is to provide a method for producing 3-butene-1,2-diol with improved yield and purity.

The method for producing 3-butene-1,2-diol according to the present disclosure includes preparing a premixture containing water, an acidic compound, 2-butene-1,4-diol, and a copper(I) catalyst, the premixture It includes heating to prepare a reaction mixture containing 3-butene-1,2-diol and divinyldioxane, and separating 3-butene-1,2-diol from the reaction mixture.

According to exemplary embodiments, the copper(I) catalyst is copper(I) chloride, copper(I) bromide, copper(I) iodide, copper(I) oxide, copper(I) sulfide, and copper(I) acetate. It may include at least one selected from the group consisting of.

According to exemplary embodiments, the content of the copper(I) catalyst in the premix may be 0.5 parts by weight to 10 parts by weight based on 100 parts by weight of 2-butene-1,4-diol.

According to exemplary embodiments, the acidic compound may include at least one selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, acetic acid, and boric acid.

According to exemplary embodiments, the content of the acidic compound in the premix may be 0.1 to 5 parts by weight based on 100 parts by weight of 2-butene-1,4-diol.

According to exemplary embodiments, the content of water in the premix may be 20 to 50 parts by weight based on 100 parts by weight of 2-butene-1,4-diol.

According to exemplary embodiments, preparing the reaction mixture may be performed at a temperature of 40°C to 100°C.

According to exemplary embodiments, before separating 3-butene-1,2-diol from the reaction mixture, the step of neutralizing the reaction mixture by adding a basic compound may be further included.

According to exemplary embodiments, separating 3-butene-1,2-diol from the reaction mixture includes removing insoluble solids from the reaction mixture to obtain a filtrate; And it may include distilling the filtrate to obtain 3-butene-1,2-diol.

According to exemplary embodiments, the step of obtaining 3-butene-1,2-diol includes first distilling the filtrate to remove water and the divinyldioxane; and performing a second distillation of the filtrate from which the water and divinyldioxane have been removed to obtain 3-butene-1,2-diol.

According to exemplary embodiments, the first distillation may be reduced pressure distillation.

According to exemplary embodiments, the first distillation may be performed at a pressure of 12 torr or less.

According to exemplary embodiments, the second distillation may be reduced pressure heating distillation.

According to exemplary embodiments, the second distillation may be performed at a pressure of 12 torr or less and a temperature of 70°C to 90°C.

According to exemplary embodiments, the yield of 3-butene-1,2-diol may be 60% to 99%.

The method for producing 3-butene-1,2-diol according to exemplary embodiments of the present disclosure includes mixing and heating water, an acidic compound, 2-butene-1,4-diol, and a copper(I) catalyst, 3 -Butene-1,2-diol and divinyldioxane can be produced. Accordingly, the reverse reaction of 3-butene-1,2-diol can be suppressed, and the production of divinyldioxane, a by-product of oxidation of 2-butene-1,4-diol, can be reduced. Therefore, the yield of the production process of 3-butene-1,2-diol can be improved, and the purity of 3-butene-1,2-diol can be improved.

The copper(I) catalyst is a low-toxicity compound and can be reused, thereby improving the reaction efficiency of the 3-butene-1,2-diol production process. Additionally, the copper(I) catalyst may be included in a predetermined amount relative to 2-butene-1,4-diol. Therefore, it is possible to suppress the oxidation of 2-butene-1,4-diol, the production of divinyldioxane, which is an oxide of 2-butene-1,4-diol, and the reverse reaction of 3-butene-1,2-diol. It can be prevented. Accordingly, the reaction rate of 2-butene-1,4-diol can be improved, and the yield of 3-butene-1,2-diol can be further improved.

Additionally, the acidic aqueous solution may be included in a predetermined amount relative to 2-butene-1,4-diol. In this case, not only can the reaction of 2-butene-1,4-diol be promoted, but also the dehydration reaction, which is a side reaction, can be suppressed. Therefore, the production of divinyldioxane as a by-product of the side reaction can be prevented, and the selectivity of 3-butene-1,2-diol can be further improved.

1 is a schematic flowchart illustrating a method for producing 3-butene-1,2-diol according to exemplary embodiments.

Examples of the present disclosure are for producing 3-butene-1,2-diol from 2-Butene-1,4-diol. A method can be provided.

According to exemplary embodiments of the present disclosure, a premixture comprising water, an acidic compound, 2-butene-1,4-diol, and copper(I) catalyst is heated to produce 3-butene-1,2-diol and diol. A reaction mixture containing vinyldioxane can be prepared, and 3-butene-1,2-diol can be separated from the reaction mixture. Accordingly, the purity of 3-butene-1,2-diol and the yield of the manufacturing process can be improved.

Hereinafter, embodiments of the present invention will be described in more detail with reference to the drawings. However, the following drawings attached to this specification illustrate preferred embodiments of the present invention, and serve to further understand the technical idea of the present invention along with the contents of the above-described invention, so the present invention is described in such drawings. It should not be interpreted as limited to the specifics.

<Method for producing 3-butene-1,2-diol>

1 is a schematic flowchart showing a method for producing 3-butene-1,2-diol according to exemplary embodiments.

Referring to Figure 1, a preliminary mixture containing water, an acidic compound, 2-butene-1,4-diol, and a copper(I) catalyst can be prepared (eg, step S10). For example, a preliminary mixture can be prepared by mixing 2-butene-1,4-diol and a copper(I) catalyst in an acidic aqueous solution containing water and an acidic compound.

According to exemplary embodiments, the copper(I) catalyst is copper(I) chloride, copper(I) bromide, copper(I) iodide, copper(I) oxide, copper(I) sulfide, and copper(I) acetate. It may include at least one selected from the group consisting of. By including the copper(I) catalyst, the selectivity of 3-butene-1,2-diol can be improved, and high purity 3-butene-1,2-diol can be produced. In addition, the dehydration reaction can be suppressed, so the production of divinyldioxane generated due to the dehydration reaction of 2-butene-1,4-diol can be suppressed.

In some embodiments, the copper(I) catalyst may include copper(I) chloride. Accordingly, the conversion reaction of 2-butene-1,4-diol to 3-butene-1,2-diol can be promoted, and side reactions and reverse reactions can be suppressed. Therefore, the selectivity of the forward reaction can be improved and the yield of 3-butene-1,2-diol can be improved.

According to exemplary embodiments, the content of the copper (I) catalyst in the premix may be 0.1 to 15 parts by weight, preferably 0.5 parts by weight, based on 100 parts by weight of 2-butene-1,4-diol. It may be 10 to 10 parts by weight, and more preferably 2.5 to 4.5 parts by weight. Within the above range, the rate of conversion reaction of 2-butene-1,4-diol to 3-butene-1,2-diol can be increased. Additionally, a by-product of the dehydration reaction of 2-butene-1,4-diol can inhibit the production of divinyldioxane. Accordingly, the catalyst remaining after the reaction can be reused, which can be more advantageous in terms of environmental friendliness and fairness.

In some embodiments, the water and acidic compound can be premixed. For example, the water and the acidic compound may be premixed to form an acidic aqueous solution and may act as a solvent. Accordingly, the added 2-butene-1,4-diol and the copper(I) catalyst can be dissolved more quickly, and the manufacturing process of 3-butene-1,2-diol can be further improved.

According to exemplary embodiments, the acidic compound in the premix may include at least one selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, acetic acid, and boric acid. Accordingly, the solubility of 2-butene-1,4-diol may increase, and the conversion rate and reaction rate to 3-butene-1,2-diol may be improved.

In some embodiments, the acidic compound may include sulfuric acid. Accordingly, a stronger acidic environment can be provided, and the conversion reaction rate of 2-butene-1,4-diol into 3-butene-1,2-diol can be further improved. Accordingly, the side reaction of 2-butene-1,4-diol can be suppressed, and the yield can be further increased.

According to exemplary embodiments, the content of the acidic compound in the premix may be 0.05 parts by weight to 1 part by weight, preferably 0.1 parts by weight to 5 parts by weight, based on 100 parts by weight of 2-butene-1,4-diol. It may be parts by weight, and more preferably 0.3 parts by weight to 1 part by weight. Within the above range, the dehydration reaction of 2-butene-1,4-diol can be suppressed, and the conversion rate of 3-butene-1,2-diol can be higher. In addition, the production of divinyldioxane, a by-product of the dehydration reaction, which is a side reaction, may be suppressed.

According to exemplary embodiments, the content of water in the premix may be 10 parts by weight to 70 parts by weight, preferably 20 parts by weight to 50 parts by weight, based on 100 parts by weight of 2-butene-1,4-diol. parts, and more preferably 25 to 40 parts by weight. Within the above range, the added 2-butene-1,4-diol and the copper(I) catalyst can be dissolved more quickly, and the manufacturing process of 3-butene-1,2-diol can be further improved. In addition, the dehydration reaction of 2-butene-1,4-diol can be suppressed, and the yield of 3-butene-1,2-diol can be improved.

According to exemplary embodiments, 2-butene-1,4-diol may be a compound represented by Formula 1 below. For example, 2-butene-1,4-diol represented by Formula 1 below is in cis form, but may include geometric isomers in trans form.

[Formula 1]

According to exemplary embodiments, the premix may be heated to prepare a reaction mixture containing 3-butene-1,2-diol and divinyldioxane (eg, step S20).

According to exemplary embodiments, 3-butene-1,2-diol may be a compound represented by Formula 2 below.

[Formula 2]

According to exemplary embodiments, divinyldioxane may include a compound in which two vinyl groups (-CH=CH ₂ ) are independently bonded to dioxane. For example, dioxane may include 1,4-dioxane, 1,3-dioxane, and 1,2-dioxane.

In some embodiments, divinyldioxane may include 2,5-divinyl-1,4-dioxane represented by Chemical Formula 3 below.

[Formula 3]

For example, in step S20, the reaction represented by Scheme 1 below may proceed to prepare the reaction mixture.

[Scheme 1]

According to exemplary embodiments, the preparation of the reaction mixture may be performed at a temperature of 25°C to 120°C, preferably at a temperature of 40°C to 100°C, and more preferably at a temperature of 50°C to 100°C. It can be carried out at a temperature of 80°C. Within the above range, the conversion rate to 3-butene-1,2-diol can be increased, and the production of divinyldioxane by side reactions and 2-butene-1,4-diol by reverse reactions can be suppressed. Yield can be improved.

In some embodiments, preparation of the reaction mixture may be performed for 1 hour to 5 hours, and preferably may be performed for 2 hours to 4 hours. Within the above range, conversion of 2-butene-1,4-diol to 3-butene-1,2-diol can be sufficiently performed.

According to exemplary embodiments, the step of neutralizing the reaction mixture by adding a basic compound may be further included. For example, a basic compound may be added to the reaction mixture and then mixed. The acidic mixture in the reaction mixture can be neutralized by the added basic compound. For example, a sulfuric acid mixture can be neutralized. Accordingly, the side reaction of the dehydration reaction can be reduced and the production of divinyldioxane can be suppressed. In addition, the reverse reaction, which is a reaction back to 2-butene-1,4-diol, can be suppressed, and the yield can be further improved.

In some embodiments, the basic compound may include at least one selected from the group consisting of potassium carbonate (K ₂ CO ₃ ), sodium carbonate (Na ₂ CO ₃ ), sodium hydroxide (NaOH), and potassium hydroxide (KOH). there is. For example, the basic compound may include potassium carbonate.

According to exemplary embodiments, 3-butene-1,2-diol can be obtained by separating it from the reaction mixture (eg, step S30).

According to exemplary embodiments, the step of separating 3-butene-1,2-diol includes removing insoluble solids from the reaction mixture to obtain a filtrate and distilling the filtrate to obtain 3-butene-1,2 -The step of obtaining diol may be further included. For example, insoluble solids that precipitate or precipitate from the reaction mixture can be removed, thereby further improving the purity of 3-butene-1,2-diol.

In some embodiments, the filtrate may be heated and distilled to obtain 3-butene-1,2-diol. The heating and distillation may be performed in stages.

According to exemplary embodiments, first distilling the filtrate to remove water and divinyldioxane, and second distilling the filtrate from which the water and divinyldioxane were removed to produce 3-butene- It may include a step of obtaining 1,2-diol.

The term “boiling point” used in this specification refers to the temperature at which the vapor pressure of the compound is in equilibrium with the surrounding atmospheric pressure or pressure. For example, the boiling point of a specific compound at a specific stage may be the temperature at which the vapor pressure of the compound is in equilibrium with the atmospheric pressure or pressure of the reactor at that stage.

For example, the first distillation may be performed at a temperature below the boiling point of 3-butene-1,2-diol. Accordingly, compounds that boil at a temperature lower than the boiling point of 3-butene-1,2-diol can be removed from the filtrate, and 3-butene-1,2-diol can remain in the filtrate. For example, water and divinyldioxane are low boiling point substances and can be partially removed from the filtrate.

According to exemplary embodiments, the first distillation may be reduced pressure distillation. As the pressure is reduced, the boiling points of the compounds can be reduced, allowing the compounds to be separated at relatively low temperatures. For example, through the first distillation, water and divinyldioxane can be separated at a lower temperature, and process time and efficiency can be improved.

According to exemplary embodiments, the first distillation may be performed at a pressure of 20 torr or less, and preferably, may be performed at a pressure of 12 torr or less. Additionally, the first distillation may be performed at a temperature of 10°C to 50°C. Within the range of the above conditions, substances with a low boiling point can be selectively removed from the filtrate. For example, water and divinyldioxane can be removed, and 3-butene-1,2-diol can be prevented from being removed from the filtrate.

According to exemplary embodiments, the second distillation may be reduced pressure heating distillation. By reducing pressure, compounds can be separated at relatively low temperatures. For example, 3-butene-1,2-diol can be separated at a lower temperature from the filtrate from which water and divinyldioxane have been removed, thereby improving process time and efficiency.

According to exemplary embodiments, the second distillation may be performed at a pressure of 20 torr or less, and preferably, may be performed at a pressure of 12 torr or less.

According to exemplary embodiments, the second distillation may be performed at 65°C to 95°C, and preferably at 70°C to 90°C. Within the range of the above conditions, 3-butene-1,2-diol can be selectively separated from the filtrate from which water and divinyldioxane have been removed. Therefore, other reactants and reaction products can be prevented from being distilled together with 3-butene-1,2-diol, and the purity of 3-butene-1,2-diol can be improved.

In some embodiments, the second distillation may be performed at a temperature above the boiling point of 3-butene-1,2-diol and below the boiling point of 2-butene-1,4-diol. Accordingly, through the second distillation, 2-butene-1,4-diol, which has a relatively high boiling point, remains in the filtrate, and only 3-butene-1,2-diol, which has a relatively low boiling point, is evaporated and obtained. It can be.

According to exemplary embodiments, the yield of 3-butene-1,2-diol may be 50% to 99%, preferably 60% to 98%, and more preferably 65% or more. . Accordingly, the conversion rate from 2-butene-1,4-diol to 3-butene-1,2-diol can be improved by including a copper (I) catalyst, and 3-butene-1,2 with improved purity can be obtained. -Dior can be obtained.

Hereinafter, experimental examples including specific examples and comparative examples are presented to aid understanding of the present invention, but these are only illustrative of the present invention and do not limit the scope of the appended claims, and do not limit the scope and technical idea of the present invention. It is obvious to those skilled in the art that various changes and modifications to the embodiments are possible within the scope, and it is natural that such changes and modifications fall within the scope of the appended patent claims.

Examples and Comparative Examples: Preparation of 3-butene-1,2-diol

(1) Example 1

Add 100 g of 2-butene-1,4-diol, 30 g of water, 0.6 g of sulfuric acid (H ₂ SO ₄ ), and 3 g of copper(I) chloride (CuCl) catalyst to a 250 mL reactor. A preliminary mixture was prepared. The premix was heated at a temperature of 60°C for 3 hours and reacted to produce a reaction mixture containing 3-butene-1,2-diol and divinyldioxane. was manufactured. The reaction mixture was cooled to room temperature, and potassium carbonate (K ₂ CO ₃ ), a basic compound, was added. It was neutralized by adding 3g. Insoluble solids were removed from the neutralized reaction mixture to obtain a filtrate. The ratios of 2-butene-1,4-diol, 3-butene-1,2-diol, and divinyldioxane present in the filtrate were analyzed using gas chromatography (GC). The filtrate was distilled under reduced pressure at a pressure of 10 torr and a temperature of 30°C to remove water and divinyldioxane, and then distilled under reduced pressure at a pressure of 10 torr and a temperature of 80°C to obtain 3-butene-1,2-diol. did.

(2) Example 2

3-Butene-1,2-diol was obtained in the same manner as in Example 1, except that 1.5 g of copper (I) chloride (CuCl) was added instead of 3 g of copper (I) chloride (CuCl).

(3) Example 3

3-Butene-1,2-diol was obtained in the same manner as in Example 1, except that 5 g of copper (I) chloride (CuCl) was added instead of 3 g of copper (I) chloride (CuCl).

(4) Example 4

3-Butene-1,2-diol was obtained in the same manner as in Example 1, except that 0.6 g of hydrochloric acid (HCl) was added instead of 0.6 g of sulfuric acid (H ₂ SO ₄ ).

(5) Example 5

3-Butene-1,2-diol was obtained in the same manner as in Example 1, except that 1.2 g of sulfuric acid (H ₂ SO ₄ ) was added instead of 0.6 g of sulfuric acid (H ₂ SO ₄ ).

(6) Comparative Example 1

3-Butene-1,2-diol was obtained in the same manner as in Example 1, except that 3 g of mercury sulfate (HgSO ₄ ) was added instead of 3 g of copper (I) chloride (CuCl).

(7) Comparative Example 2

The same procedure as in Example 1 was carried out, except that 3 g of copper (I) chloride (CuCl) was not added.

The types and contents of acidic compounds and catalysts in the examples and comparative examples are shown in Table 1 below.

Acidic compound content (g) Catalyst content (g) Example 1 Sulfuric acid 0.6 Copper(I) chloride 3 Example 2 Sulfuric acid 0.6 Copper(I) chloride 1.5 Example 3 Sulfuric acid 0.6 Copper(I) chloride 5 Example 4 Hydrochloric acid 0.6 Copper(I) chloride 3 Example 5 Sulfuric acid 1.2 Copper(I) chloride 3 Comparative Example 1 Sulfuric acid 0.6 Mercury(II) sulfate 3 Comparative Example 2 Sulfuric acid 0.6 -

Experimental example: Yield evaluation of 3-butene-1,2-diol

Gas chromatography (GC) was used to analyze the ratios of 2-butene-1,4-diol, 3-butene-1,2-diol, and divinyldioxane present in the filtrate.

Afterwards, the yield of 3-butene-1,2-diol was calculated as a percentage of the ratio of the weight of 3-butene-1,2-diol obtained to the weight of 2-butene-1,4-diol added.

The evaluation results are shown in Table 2 below.

division GC analysis results 3-Butene-1,2-diol yield (%) 2-Butene-1,4-diol ratio (%) Divinyldioxane
ratio (%) 3-Butene-1,2-diol ratio (%) Example 1 2 3 76 68 Example 2 3 4 68 63 Example 3 One 2 73 65 Example 4 4 5 66 62 Example 5 3 3 72 65 Comparative Example 1 15 45 30 35 Comparative Example 2 90 - - -

Referring to Table 2, when 3-butene-1,2-diol was produced by the method for producing 3-butene-1,2-diol according to the exemplary embodiments, the proportion of 2-butene-1,4-diol in the filtrate was further reduced. You can check it. Therefore, it can be confirmed that the conversion rate of 2-butene-1,4-diol to 3-butene-1,2-diol was improved.

Additionally, in the examples, it can be seen that the proportion of divinyldioxane was relatively reduced. Accordingly, it can be seen that the side reaction of 2-butene-1,4-diol is suppressed, and the proportion of divinyldioxane, a by-product of the side reaction, is further reduced.

Additionally, in the examples, it can be seen that the yield of 3-butene-1,2-diol was further improved. Therefore, it can be confirmed that the reverse reaction of converting 3-butene-1,2-diol back to 2-butene-1,4-diol is suppressed.

In the case of Comparative Example 1, which used a mercury sulfate catalyst instead of a copper (I) chloride catalyst, it can be seen that the proportion of divinyldioxane was relatively increased compared to the examples. In addition, it can be confirmed that not only is the conversion of 2-butene-1,4-diol to 3-butene-1,2-diol suppressed, but side reactions are further promoted. Therefore, it can be confirmed that the yield of 3-butene-1,2-diol was reduced.

In the case of Comparative Example 2 in which a copper(I) chloride catalyst was not used, it could be confirmed that the reaction to convert 2-butene-1,4-diol to 3-butene-1,2-diol did not occur.

Claims (15)

Preparing a premixture comprising water, an acidic compound, 2-butene-1,4-diol and a copper(I) catalyst;
Preparing a reaction mixture containing 3-butene-1,2-diol and divinyldioxane by heating the preliminary mixture; and
A method for producing 3-butene-1,2-diol, comprising the step of separating 3-butene-1,2-diol from the reaction mixture.
The method of claim 1, wherein the copper(I) catalyst is a group consisting of copper(I) chloride, copper(I) bromide, copper(I) iodide, copper(I) oxide, copper(I) sulfide, and copper(I) acetate. A method for producing 3-butene-1,2-diol, comprising at least one selected from.
The method of claim 1, wherein the content of the copper (I) catalyst in the premix is 0.5 parts by weight to 10 parts by weight based on 100 parts by weight of 2-butene-1,4-diol. Manufacturing method.
The method for producing 3-butene-1,2-diol according to claim 1, wherein the acidic compound includes at least one selected from the group consisting of sulfuric acid, hydrochloric acid, nitric acid, phosphoric acid, acetic acid, and boric acid.
The method for producing 3-butene-1,2-diol according to claim 1, wherein the content of the acidic compound in the premix is 0.1 parts by weight to 5 parts by weight based on 100 parts by weight of 2-butene-1,4-diol.
The method of claim 1, wherein the content of water in the premix is 20 to 50 parts by weight based on 100 parts by weight of 2-butene-1,4-diol.
The method for producing 3-butene-1,2-diol according to claim 1, wherein the step of preparing the reaction mixture is performed at a temperature of 40°C to 100°C.
The method of claim 1, further comprising the step of neutralizing 3-butene-1,2-diol by adding a basic compound to the reaction mixture before separating 3-butene-1,2-diol from the reaction mixture. Manufacturing method.
The method of claim 1, wherein the step of separating 3-butene-1,2-diol from the reaction mixture comprises:
Obtaining a filtrate by removing insoluble solids from the reaction mixture; and
A method for producing 3-butene-1,2-diol, comprising the step of distilling the filtrate to obtain 3-butene-1,2-diol.
The method of claim 9, wherein the step of obtaining 3-butene-1,2-diol,
First distilling the filtrate to remove water and the divinyldioxane; and
A method for producing 3-butene-1,2-diol, comprising the step of second distilling the water and the filtrate from which the divinyldioxane was removed to obtain 3-butene-1,2-diol.
The method of claim 10, wherein the first distillation is reduced pressure distillation.
The method of claim 11, wherein the first distillation is performed at a pressure of 12 torr or less.
The method for producing 3-butene-1,2-diol according to claim 10, wherein the second distillation is reduced pressure heating distillation.
The method of claim 13, wherein the second distillation is performed at a pressure of 12 torr or less and a temperature of 70°C to 90°C.
The method for producing 3-butene-1,2-diol according to claim 1, wherein the yield of 3-butene-1,2-diol is 60% to 99%.