KR102051872B1 - Method of manufacturing Dialkyl carbonate using carbon dioxide - Google Patents

Abstract

One embodiment of the present invention provides a method for preparing dialkyl carbonate using carbon dioxide. More specifically, mixing a catalyst and a base including an alcohol, an imidazolium cation and a bicarbonate anion in a solvent to form a mixture, wherein Injecting carbon dioxide into the mixture to produce a reactant and a method for producing a dialkyl carbonate comprising the step of stirring the reactant.

Description

Method of manufacturing Dialkyl carbonate using carbon dioxide

The present invention relates to a method for producing a dialkyl carbonate using carbon dioxide, and more particularly, imidazolium cation and bicarbonate anion in the dibromomethane and alcohol mixed solvent conditions of carbon dioxide and methanol to octanol alcohol in a single container The present invention relates to a method for producing a dialkyl carbonate using an alkali metal triazolide as a base as an ionic liquid compound.

Dialkylcarbonate is an environmentally friendly chemical that is not toxic to the human body and is drawing attention as the demand increases in various fields. Dialkyl carbonate is used for methylation and carbonylation of fine chemicals because it has the characteristic of introducing functional groups such as methyl group, methoxy group and methoxycarbonyl group to structurally different chemicals. The reaction can replace highly corrosive and toxic chemicals such as dimethyl sulfate and phosgene. Moreover, dialkyl carbonate can replace toxic phosgene, methyl chloride and dimethyl sulfate, as well as dilute with gasoline, high oxygen content and harmless, so it can be used as an octane number improver for automobile fuels. It is considered to be a substitute for harmful methyl tertary butyl ether (MTBE). In addition, the application range of the intermediates of electrolytes and fine chemicals of secondary batteries is very wide and is widely applied in various fields such as high-performance resins, solvents, dye intermediates, drugs, fragrances, food preservatives, lubricant additives.

Several processes are known at present as a process for producing dialkyl carbonate. Typical reactions include phosgene process for reacting toxic phosgene with methanol, methylnitrite process using methyl nitrite, methanol oxidation method for reacting carbon monoxide and oxygen with methanol, ethylene oxide And transesterification method (esterification) using. Conventionally, dialkyl carbonates are prepared using phosgene, methanol and high concentration of caustic soda solution, which are known as toxic substances, but phosgene, which is a toxic substance, is a very toxic dangerous substance. Therefore, the methanol oxidation method, the methyl nitrite method, the transesterification method, etc. have been studied as an alternative to the phosgene process.

Among them, a methanol oxidation method (enichem process) for synthesizing dialkyl carbonate by reacting oxygen and carbon monoxide with methanol under a copper (I) catalyst is carried out. However, this process has the disadvantage of short catalyst life, reactor corrosion problems and the use of toxic reactants such as carbon monoxide. In addition, the water produced as a by-product during the reaction adds high energy costs to the separation and purification.

Another phosgene replacement is the methyl nitrite process, which is a two-step process. In the first step of the process, methanol is oxidized with nitrogen dioxide to produce methyl nitrite, and in the second step, methylnitrite and carbon monoxide are reacted with carbon monoxide to produce dialkyl carbonate under palladium catalytic conditions. . Nitrogen monoxide produced as a by-product in this process has the advantage that it can be oxidized back to the reactant nitrogen dioxide and reused in the first process step. However, this process also has the problem that toxic carbon monoxide is used as a reactant and one of the products, nitrogen monoxide, corrodes the reactor.

Another method of preparing dialkyl carbonates is a transesterification process consisting of a two step process of reacting ethylene oxide with carbon dioxide under a catalyst to produce a dialkyl carbonate. Compared to the previous process, this process has the advantage of reducing the corrosion problems of the reactor, using cheaper and less toxic raw materials, and ethylene glycol produced as a reaction by-product can be recycled to the reactant ethylene oxide through an appropriate chemical reaction. However, despite the reaction at high temperature and high pressure, it shows low catalytic activity and short catalyst life.

In addition, since the organic solvent used in the reaction forms a triple azeotropy between methanol and dialkyl carbonate, there is a disadvantage that a large amount of energy is required to separate and purify the dialkyl carbonate after the reaction.

Each of the above processes uses toxic reactants such as carbon monoxide and has problems such as corrosion of the reactor, high process cost due to the multistage process, and difficulty in separation and purification due to by-product generation. In order to overcome this problem, a method of directly synthesizing a dialkyl carbonate from methanol and carbon dioxide (CO 2) has recently been proposed (Non Patent Literatures 12 to 14). Direct synthesis of dialkyl carbonate is a simple process, low cost of methanol and carbon dioxide (CO2) used as a raw material, and is an environmentally friendly process that does not use toxic substances such as phosgene. However, there is a problem that the yield of dialkyl carbonate is low because it is a thermodynamically balanced reversible process, and various catalyst groups have been studied, but a suitable catalyst system and an efficient synthesis method have not yet been proposed.

Therefore, it is necessary to study the catalyst necessary for synthesizing dialkyl carbonate in an environmentally friendly process.

Republic of Korea Registered Patent KR 10-1736963

The technical problem to be achieved by the present invention is to provide a method for producing dialkyl carbonate using carbon dioxide which is a cheap raw material in an environment-friendly and simple process without using a conventional toxic substance.

More specifically, the present invention relates to a method for producing an environmentally friendly dialkyl carbonate using the catalyst of the present invention, which is a simple and inexpensive raw material, which is a simple and inexpensive raw material by directly synthesizing a dialkyl carbonate from alcohol and carbon dioxide. .

The technical problem to be achieved by the present invention is not limited to the technical problem mentioned above, and other technical problems not mentioned above may be clearly understood by those skilled in the art from the following description. There will be.

In order to achieve the above technical problem, an embodiment of the present invention provides a method for producing dialkyl carbonate using carbon dioxide. The method for preparing a dialkyl carbonate includes mixing a catalyst and a base including an alcohol, an imidazolium cation and a bicarbonate anion in a solvent to form a mixture, and injecting carbon dioxide into the mixture to generate a reactant. You can do

In addition, the base is characterized in that it comprises Cs [Triazolide], Cs [Benzotriazolide] or Cs [Amino-triazolide].

In addition, the solvent is characterized in that it comprises CH ₂ Br ₂ or CH ₂ Cl ₂ .

In addition, the reaction temperature in the step of forming the mixture is characterized in that 40 ℃ to 90 ℃.

In addition, the alcohol and the base is characterized in that the 0.9 mol to 1.1 mol based on 1 mol of the catalyst.

In addition, the step of generating a reactant by injecting the carbon dioxide

Injecting carbon dioxide into the mixture at a first pressure, stirring the mixture injected with carbon dioxide at the first pressure, and injecting carbon dioxide at a second pressure into the stirred mixture.

In addition, the first pressure is characterized in that 10psi to 90psi, the second pressure is characterized in that 200psi to 600psi.

In addition, the reaction time of the method for producing a dialkyl carbonate is characterized in that more than 24 hours.

In order to achieve the above technical problem, another embodiment of the present invention is used to synthesize a dialkyl carbonate from alcohol and carbon dioxide, and provides a catalyst comprising an imidazolium cation and a bicarbonate anion.

According to an embodiment of the present invention, high yield dialkyl carbonate may be prepared by directly reacting alcohol and carbon dioxide in a simple process in a single container.

In addition, since dialkyl carbonate is prepared using carbon dioxide and alcohol, an effect of reducing manufacturing cost may be obtained.

In addition, it is possible to obtain the effect of providing an environment-friendly manufacturing, energy and time-saving process without using toxic reactants.

The effects of the present invention are not limited to the above-described effects, but should be understood to include all the effects deduced from the configuration of the invention described in the detailed description or claims of the present invention.

1 is a flow chart showing a method for producing a dialkyl carbonate of the present invention.
Figure 2 is a schematic diagram showing a process for producing a dimethyl carbonate of the present invention.

Hereinafter, with reference to the accompanying drawings will be described the present invention. As those skilled in the art would realize, the described embodiments may be modified in various different ways, all without departing from the spirit or scope of the present invention. In the drawings, parts irrelevant to the description are omitted in order to clearly describe the present invention, and like reference numerals designate like parts throughout the specification.

Throughout the specification, when a part is said to be "connected (connected, contacted, coupled)" with another part, it is not only "directly connected" but also "indirectly connected" with another member in between. "Includes the case. In addition, when a part is said to "include" a certain component, this means that it may further include other components, without excluding the other components unless otherwise stated.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. Singular expressions include plural expressions unless the context clearly indicates otherwise. As used herein, the terms "comprise" or "have" are intended to indicate that there is a feature, number, step, action, component, part, or combination thereof described on the specification, and one or more other features. It is to be understood that the present invention does not exclude the possibility of the presence or the addition of numbers, steps, operations, components, components, or a combination thereof.

Hereinafter, exemplary embodiments of the present invention will be described in detail with reference to the accompanying drawings.

1 is a flow chart showing a method for producing a dialkyl carbonate of the present invention.

Referring to FIG. 1, a method of preparing dialkyl carbonate (DMC) according to an embodiment of the present invention is to form a mixture by mixing a catalyst and a base including an alcohol, an imidazolium cation, and a bicarbonate anion in a solvent. Step (S100) and injecting carbon dioxide into the mixture may be characterized in that it comprises a step (S200) for generating a reactant.

First, a catalyst and a base including an alcohol, an imidazolium cation, and a bicarbonate anion are mixed with a solvent to form a mixture (S100).

For example, the alcohol may include 1 to 8 carbon atoms of alcohol to octanol.

For example, the catalyst including the imidazolium cation and the bicarbonate anion may include [IL tagged Huning base] cation [HCO ₃ ] anion catalyst of the following [Formula 1].

[Formula 1]

In addition, the base may be characterized by comprising Cs [Triazolide], Cs [Benzotriazolide] or Cs [Amino-triazolide].

For example, the structural formula of the base may include the following [Formula 2].

[Formula 2]

In addition, the solvent may be characterized in that it comprises CH ₂ Br ₂ or CH ₂ Cl ₂ .

For example, when CH ₂ Br ₂ is used as the solvent, the MeOH conversion may be 86.2%, and the yield of DMC may be 83.0%.

In addition, the reaction temperature in the step of forming the mixture may be characterized in that 40 ℃ to 90 ℃.

If the reaction temperature is 40 ℃ to 90 ℃ the optimum temperature of the chemical reaction and the deviation of the catalyst may be lowered.

For example, when the reaction temperature is 80 ° C., a high yield of MeOH conversion of 88.0% and DMC yield of 85.0% can be obtained.

In addition, the alcohol and the base may be characterized in that the 0.9 mol to 1.1 mol based on the catalyst.

When the alcohol and the base is less than 0.9 mol or greater than 1.1 mol based on 1 mol of the catalyst, alcohol alcohol brittleness or dialkyl carbonate yield may decrease.

For example, when the molar ratio of (catalyst: base: methanol) is 1: 1: 1, a high yield can be obtained with a methanol yield of 86.2% and a DMC yield of 83.0%.

Next, carbon dioxide is injected into the mixture to generate a reactant (S200).

Injecting the carbon dioxide to produce a reactant, injecting carbon dioxide into the mixture at a first pressure, stirring the mixture injected with carbon dioxide at the first pressure and carbon dioxide at a second pressure in the stirred mixture It may be characterized in that it comprises the step of injecting.

In addition, the first pressure may be characterized in that 10psi to 90psi, the second pressure may be characterized in that 200psi to 600psi.

When the first reaction pressure is less than 10 psi, the yield of dialkyl carbonate may be reduced. When the first reaction pressure exceeds 90 psi, the hydrolysis reaction of the dialkyl carbonate as a product is predominant by the water formed as a reaction byproduct. There may be a problem of this deterioration may be undesirable.

In addition, when the second reaction pressure is less than 200 psi, the yield may be decreased, and when the second reaction pressure exceeds 600 psi, it may not be expected to improve the yield with unnecessary pressure.

In addition, the reaction time of the method for producing a dialkyl carbonate may be characterized in that more than 24 hours.

When the reaction time is less than 24 hours, the yield of dialkyl carbonate may be reduced. When the reaction time is greater than 24 hours, the yield of dialkyl carbonate may increase as the time increases. However, yields may not improve significantly.

The stirring speed in the step of forming the reactant may be, for example, characterized in that 300rpm to 1000rpm.

When the stirring speed is 300rpm to 1000rpm, it is suitable, but it is preferable to carry out in the region where the mass transfer between carbon dioxide and alcohol is maximum in consideration of the state of the catalyst and the viscosity of the solvent.

In addition, a high yield of dialkyl carbonate can be produced by the above-described method for producing dialkyl carbonate.

It is also used to synthesize dialkyl carbonates from alcohols and carbon dioxide, and can provide a catalyst comprising an imidazolium cation and a bicarbonate anion.

The catalyst can provide a process that saves energy, cost and time by using cheap and abundant raw materials without using toxic reactants.

Preparation Example 1

1) Catalyst 5 mmol, Cs [Triazolide] containing 5 mmol methanol, imidazolium cation and bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) in 100 ml of high pressure stainless steel reactor equipped with magnetic stirrer and electric heater A mixture was prepared by mixing 5 mmol of base and 15 ml of CH ₂ Br ₂ solvent.

2) The mixture was purged of carbon dioxide to the reactor at 80 psi pressure.

3) The atmosphere was evacuated three times from the mixture.

4) Stirred at 500 rpm, heated to 50 ° C. and raised carbon dioxide pressure to 300 psi.

5) The reaction was performed for 24 hours while maintaining the carbon dioxide pressure at 300 psi to prepare dimethyl carbonate (DMC).

6) After the reaction was completed, the reaction mixture was allowed to stand at room temperature, and the resulting mixture was transferred to a vial to calculate the conversion of methanol and the yield of dimethyl carbonate using GD-FID.

In addition, the yield calculation method of the dimethyl carbonate of Preparation Example 6 6 may be the following equation.

[Equation]

For example, the DMC yield can be confirmed by substituting the number of moles of DMC generated through the theoretical value and the number of moles of DMC generated in Preparation Example 1.

Figure 2 is a schematic diagram showing a process for producing a dimethyl carbonate of the present invention.

2, methanol, [IL tagged huning base] [HCO ₃ ] catalyst and Cs [Triazolide] base is added to a solvent to prepare a mixture, and the mixture is injected with CO ₂ to the catalyst and base. By reacting methanol and carbon dioxide, dimethyl carbonate (DMC) can be easily produced in a single container.

[Scheme]

Catalyst (catalyst) of the scheme may be [IL tagged huning base] [HCO ₃ ] and Cs [Triazolide].

Comparative Example 1

1) Preparation Example except that [Bmim] [HCO3] of [Formula 3] was used as a catalyst instead of a catalyst containing an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) DMC was prepared in the same manner as in 1.

[Formula 3]

Comparative Example 2

1) Preparation Example except that [Bmim] [Benzotriazolide] of [Formula 4] was used as a catalyst instead of a catalyst containing an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) DMC was prepared in the same manner as in 1.

 [Formula 4]

Comparative Example 3

1) DMC was carried out in the same manner as in Preparation Example 1, except that a catalyst supporting CsBr in PEG400 was used instead of a catalyst including an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]). Was prepared.

Comparative Example 4

1) DMC was carried out in the same manner as in Preparation Example 1, except that K ₃ PO ₄ was used as the catalyst instead of the catalyst including the imidazolium cation and the bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]). Prepared.

Comparative Example 5

1) Preparation Example 1 except that it was used as the [IL-1] catalyst of [Formula 5] in place of the catalyst containing an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) DMC was prepared in the same manner.

 [Formula 5]

Comparative Example 6

1) Preparation Example 1 except that it was used as the [IL-2] catalyst of [Formula 6] in place of the catalyst containing an imidazolium cation and a bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) DMC was prepared in the same manner.

 [Formula 6]

Comparative Example 7

1) In the same manner as in Preparation Example 1, except that the catalyst was used instead of the catalyst containing imidazolium cation and bicarbonate anion ([IL tagged Hunig base] [HCO ₃ ]) as [IL3] of [Formula 7]. DMC was prepared by the operation.

 [Formula 7]

[Table 1] to [Table 6] is a table comparing the conversion rate of methanol (MeOH) and the yield of DMC (dimethyl carbonate) by changing the reaction conditions of the production examples and comparative examples.

In addition, C of Table 1-Table 6 shows conversion Y as a yield.

Table 1 is a comparison table of methanol conversion and DMC yield according to catalyst.

catalyst base C _MeOH ,
(%) Y _DMC ,
(%) Preparation Example 1 Cs [Triazolide] 86.2 83.0 Comparative Example 1 Cs [Triazolide] 65.6 60.0 Comparative Example 2 Cs [Triazolide] 14.0 11.1 Comparative Example 3 Cs [Triazolide] 2.4 0 Comparative Example 4 Cs [Triazolide] 5.3 0

Referring to Table 1, MeOH 5 mmol, catalyst 5 mmol, base (Cs [Triazolide]) 5 mmol, solvent (CH ₂ Br ₂ ) 15 mL, reaction temperature 50 ℃, reaction pressure 300 psi, the same reaction time of 24 hours When the DMC was prepared using different catalysts under the reaction conditions, comparing Preparation Example 1 and Comparative Example 1 to Comparative Example 4, it was confirmed that the highest conversion rate of 86.2% of MeOH and 83.0% of DMC in Preparation Example 1 have.

Table 2 is a comparison table of methanol conversion and DMC yield according to base type.

catalyst base C _MeOH ,
(%) Y _DMC ,
(%) Preparation Example 1 None 69.1 51.2 Preparation Example 1 Cs [Triazolide] 86.2 83.0 Preparation Example 1 Cs [Benzotriazolide] 70.5 66.1 Preparation Example 1 Cs ₂ CO ₃ 78.1 72.0 Preparation Example 1 DBU 76.7 70.5 Preparation Example 1 Cs [Nitroo-Triazolide] 62.6 56.3

Referring to Table 2, when prepared under the same reaction conditions as in Preparation Example 1, but prepared DMC with different bases, when Cs [Triazolide] is used as the base, conversion of MeOH, yield of 86.2%, DMC yield of 83.0% It could be confirmed that high.

The following structural formulas show the structural formulas of the bases used in Table 2.

Table 3 is a comparison table of methanol conversion and DMC yield according to the catalyst.

catalyst base C _MeOH ,
(%) Y _DMC ,
(%) None Cs [Triazolide] 2.4 0 Preparation Example 1 Cs [Triazolide] 86.2 83.0 Comparative Example 5 Cs [Triazolide] 88.1 74.9 Comparative Example 6 Cs [Triazolide] 89.7 79.4 Comparative Example 7 Cs [Triazolide] 70.5 65.7

Referring to Table 3 above, MeOH 5 mmol, catalyst 5 mmol, base (Cs [Triazolide]) 5 mmol, solvent (CH ₂ Br ₂ ) 15 mL, reaction temperature 50 ° C., reaction pressure 300 psi, reaction time of 24 hours When the DMC was prepared using different catalysts under the reaction conditions, when no catalyst was added, it was confirmed that the DMC yield was the highest as 83.0% in Preparation Example 1 when comparing Preparation Example 1 and Comparative Examples 5 to 7. And it can be seen that the DMC can not be produced without using a catalyst.

Table 4 is a comparison table of methanol conversion and DMC yield according to reaction temperature.

catalyst base Reaction temperature,
(℃) C _MeOH ,
(%) Y _DMC ,
(%) Preparation Example 1 Cs [Triazolide] 50 86.2 83.0 Preparation Example 1 Cs [Triazolide] 80 88.0 85.0 Preparation Example 1 Cs [Triazolide] 100 70.2 67.9

Referring to Table 4, when the DMC was prepared under the same reaction conditions as in Preparation Example 1, but with different reaction temperatures, when the reaction temperature was 80 ° C, the conversion was 88.0% for MeOH and 85.0% for DMC. It can be confirmed that the high, it is confirmed that the reactivity of the catalyst is lower than a certain reaction temperature.

Table 5 is a comparison table of methanol conversion and DMC yield depending on the solvent.

catalyst base menstruum C _MeOH ,
(%) Y _DMC ,
(%) Preparation Example 1 Cs [Triazolide] CH ₂ Br ₂ 86.2 83.0 Preparation Example 1 Cs [Triazolide] NMP 2.8 0 Preparation Example 1 Cs [Triazolide] DMF 3.6 0 Preparation Example 1 Cs [Triazolide] Dioxane 1.5 0 Preparation Example 1 Cs [Triazolide] Toluene 2.0 0 Preparation Example 1 Cs [Triazolide] THF 2.7 0

Referring to Table 5, when the DMC was prepared under the same reaction conditions as in Preparation Example 1, but using different solvents, using CH ₂ Br ₂ solvent, the conversion rate of MeOH was 86.2%, and the yield of DMC was 83.0%. It can be confirmed that the high, in the case of other solvents was confirmed that little reactivity.

Table 6 is a comparison table of methanol conversion and DMC yield according to the ratio of catalyst, base and MeOH.

catalyst base Molar ratio,
(Catalyst: base: MeOH) C _MeOH ,
(%) Y _DMC ,
(%) Preparation Example 1 Cs [Triazolide] 1: 1: 1 86.2 83.0 Preparation Example 1 Cs [Triazolide] 1: 1: 2 36.4 30.2 Preparation Example 1 Cs [Triazolide] 1: 1: 4 15.6 13.8

Referring to Table 6, the DMC was prepared under the same reaction conditions as Preparation Example 1, but the catalyst, base, and MeOH ratios were different, and the molar ratio (catalyst: base: MeOH) was 1: 1: 1. In the case of MeOH conversion rate of 86.2%, DMC yield of 83.0% can be confirmed that the highest, the amount of MeOH increases the decrease in reactivity can be confirmed.

Table 7 is a comparative table comparing the alcohol conversion and the dialkyl carbonate yield after preparing the alcohol type in Preparation Example 1.

catalyst base Alcohol types C _ROH ,
(%) Y _{dialkyl carbonate} ,
(%) Preparation Example 1 Cs [Triazolide] methanol 86.2 83.0 Preparation Example 1 Cs [Triazolide] ethanol 78.9 75.4 Preparation Example 1 Cs [Triazolide] n-Propanol 75.4 72.3 Preparation Example 1 Cs [Triazolide] Isopropanol 70.6 68.7 Preparation Example 1 Cs [Triazolide] n-butanol 68.5 64.9 Preparation Example 1 Cs [Triazolide] n-pentanol 64.7 63.7 Preparation Example 1 Cs [Triazolide] n-hexanol 65.8 64.7 Preparation Example 1 Cs [Triazolide] n-heptanol 60.7 58.7 Preparation Example 1 Cs [Triazolide] n-octanol 60.4 55.7

Referring to Table 7, the dialkyl carbonate was prepared under the same reaction conditions as in Preparation Example 1, but when dialkyl carbonates were prepared using different alcohols, the conversion of alcohol was 55.7 to 83.0% and the yield was 60.4 to 86.2%. It could be confirmed that the longer the length of the alkyl group can be seen that the lower the yield.

According to an embodiment of the present invention, high yield dialkyl carbonate may be prepared by directly reacting alcohol and carbon dioxide in a simple process in a single container.

In addition, since dialkyl carbonate is prepared using carbon dioxide and alcohol, an effect of reducing manufacturing cost may be obtained.

In addition, it is possible to obtain the effect of providing an environment-friendly manufacturing, energy and time-saving process without using toxic reactants.

The effects of the present invention are not limited to the above-described effects, but should be understood to include all the effects deduced from the configuration of the invention described in the detailed description or claims of the present invention.

The foregoing description of the present invention is intended for illustration, and it will be understood by those skilled in the art that the present invention may be easily modified in other specific forms without changing the technical spirit or essential features of the present invention. will be. Therefore, it should be understood that the embodiments described above are exemplary in all respects and not restrictive. For example, each component described as a single type may be implemented in a distributed manner, and similarly, components described as distributed may be implemented in a combined form.

The scope of the present invention is represented by the following claims, and it should be construed that all changes or modifications derived from the meaning and scope of the claims and their equivalents are included in the scope of the present invention.

Claims (9)

Mixing an alcohol, a catalyst including a imidazolium cation of Formula 1 and a bicarbonate anion, and a base in a solvent to form a mixture; And
Injecting carbon dioxide into the mixture to produce a reactant; Dialkyl carbonate manufacturing method comprising a:
[Formula 1]

The method of claim 1,
The base is Cs [Triazolide], Cs [Benzotriazolide] or Cs [Amino-triazolide] method comprising a dialkyl carbonate.
The method of claim 1,
The solvent is a method for producing a dialkyl carbonate, characterized in that it comprises CH ₂ Br ₂ or CH ₂ Cl ₂ .
The method of claim 1,
The reaction temperature in the step of forming the mixture is a dialkyl carbonate production method, characterized in that 40 ℃ to 90 ℃.
The method of claim 1,
The alcohol and the base is a dialkyl carbonate production method, characterized in that from 0.9mol to 1.1mol based on 1mol of the catalyst.
The method of claim 1,
Injecting the carbon dioxide to generate a reactant
Injecting carbon dioxide into the mixture at a first pressure;
Stirring the mixture injected with carbon dioxide at the first pressure; And
Injecting carbon dioxide into the stirred mixture at a second pressure; Dialkyl carbonate production method comprising a.
The method of claim 6,
The first pressure is characterized in that 10psi to 90psi, the second pressure is a dialkyl carbonate manufacturing method, characterized in that 200psi to 600psi.
The method of claim 1,
The reaction time of the method for producing a dialkyl carbonate is a dialkyl carbonate production method, characterized in that more than 24 hours.
A catalyst, which is used to synthesize dialkyl carbonate from alcohol and carbon dioxide, comprises an imidazolium cation and a bicarbonate anion and is represented by the following formula (1):
[Formula 1]

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