KR20230058875A - Method for preparing carbonate compounds - Google Patents

Abstract

The present invention relates to a method for producing a carbonate compound, and more particularly, to synthesize a compound represented by the following Chemical Formula 2 by reacting a compound represented by the following Chemical Formula 1 with a fluorinating agent in a reaction solvent and an oxygen atmosphere, wherein the reaction solvent relates to a method for producing a carbonate compound, characterized in that water is used alone, and a compound containing a predetermined cation and a halogen anion is used as a solid phase as the fluorinating agent.
According to the present invention, there is an effect of providing a method for preparing a carbonate compound capable of improving the reaction environment and implementing reaction stability by using water alone as a reaction solvent.

Description

Manufacturing method of carbonate compounds {METHOD FOR PREPARING CARBONATE COMPOUNDS}

The present invention relates to a method for preparing a carbonate compound, and more particularly, to a method for preparing a carbonate compound capable of improving a reaction environment and implementing reaction stability by using water alone as a reaction solvent.

The halogenated cyclic carbonate compound can be obtained as a by-product when the terminal hydroxyl group is substituted with chlorine using PCl3 in straight-chain alcohol, or can be produced by direct halogenation of the cyclic carbonate compound using difluorine.

The obtained cyclic carbonate compound is treated with a fluorinating agent to increase reactivity, and the cyclic carbonate compound thus produced contains a highly reactive fluorine group at the end and is used as a fuel additive in industrial processes and as an electrolyte solution for lithium ion batteries. It is used as a functional material.

At this time, AsF ₃ , NaF, KF, ZnF ₂ , KSO ₂ F or SbF ₃ is usually used as a fluorination agent, and among them, SbF ₃ is known to have the best effect.

However, in the case of SbF ₃ , hydrogen fluoride, which is a by-product, is generated during reaction with water. Since the reaction is conducted under a nitrogen atmosphere to suppress this, it is difficult to control the reaction environment and difficult to treat the generated hydrogen fluoride.

In addition, when using SbF ₃ in a solid state without adding a solvent, disadvantages such as heat generation, compound damage, and yield reduction are identified during the reaction, which is disadvantageous for industrial use.

Accordingly, it is necessary to develop a technology using a fluorinating agent that can replace SbF ₃ .

Chinese Patent Publication No. 109369707

In order to solve these problems of the prior art, the present invention has no concern about the formation of by-products when reacting with water and does not require a nitrogen atmosphere, so that it can replace SbF ₃ Provides a method for producing a carbonate compound using a fluorinating agent aims to do

The above and other objects of the present invention can all be achieved by the present invention described below.

In order to achieve the above object, the present invention

Under a reaction solvent and oxygen atmosphere, the compound represented by the following formula (1) and a fluorinating agent are reacted to synthesize the compound represented by the formula (2),

The reaction solvent is water alone,

The fluorinating agent provides a method for preparing a carbonate compound, characterized in that a compound containing a cation represented by Formula 3 and a halogen anion is used in a solid phase.

[Formula 1]

[Formula 2]

(In Formulas 1 and 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0 R ₁ is hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least contains one or more carbons.)

[Formula 3]

(In Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and containing at least 1 carbon atom.)

The halogen anion may be a fluoride ion.

The water may be added in an amount of 300 to 500 parts by weight based on 100 parts by weight of the compound represented by Formula 1.

The fluorinating agent may be added in an amount of 2 to 4 equivalents based on 1 equivalent of the compound represented by Formula 1.

During the reaction, the reaction temperature may be 40 to 60 °C.

preparing a reactant solution by mixing the reaction solvent and the compound represented by Formula 1; Injecting a fluorinating agent into the reactant solution; and maintaining the reactant solution into which the fluorinating agent is introduced at 25 to 30° C. under an oxygen atmosphere.

The compound represented by Formula 1 may be a compound represented by Formula 4 below, and the compound represented by Formula 2 may be a compound represented by Formula 5 below.

[Formula 4]

[Formula 5]

The fluorinating agent may be tetrabutylammonium fluoride hydrate.

The reaction may be terminated by introducing a quench reagent.

The terminating reagent may be ammonium chloride.

In addition, the present invention,

Injecting a fluorinating agent into a reaction vessel;

sequentially introducing a reaction solvent and a compound represented by Formula 1 into the reaction vessel;

synthesizing a compound represented by Formula 2 by maintaining the reaction vessel at 25 to 30° C. under an oxygen atmosphere; and

The step of separating the layers of the compound represented by Formula 2 and then purifying the supernatant by distillation,

The reaction solvent is water alone,

The fluorinating agent provides a method for preparing a carbonate compound, characterized in that a compound containing a cation represented by Formula 3 and a halogen anion is used in a solid phase.

[Formula 1]

[Formula 2]

(In Formulas 1 and 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0 R ₁ is hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least contains one or more carbons.)

[Formula 3]

(In Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and containing at least 1 carbon atom.)

According to the present invention, there is an effect of providing a method for preparing a carbonate compound capable of improving the reaction environment and implementing reaction stability by using water alone as a reaction solvent.

1 is a ¹ H-NMR graph of a carbonate compound obtained in Example 1 to be described later.

Hereinafter, a method for preparing the carbonate compound of the present disclosure will be described in detail.

In the case of using a specific reaction solvent and a specific fluorinating agent in synthesizing a predetermined carbonate compound from a starting material under a reaction solvent and oxygen atmosphere, the reaction environment is improved and reaction stability is improved by using water alone as the reaction solvent. It was confirmed that it is possible to implement, and based on this, the present invention has been completed.

The term "alkylene" used in the present invention refers to a divalent radical derived from alkyl, and the term "alkyl" includes straight-chain, branched-chain or cyclic hydrocarbon radicals. For example, the alkylene includes methylene, ethylene, isobutylene, cyclohexylene, cyclopentylethylene, 2-propenylene, 3-butynylene, and the like.

In the expression of the term "substituted or unsubstituted" used in the present invention, "substitution" means that one or more hydrogen atoms in a hydrocarbon are each, independently of each other, replaced with the same or different substituents.

Here, the substituent may be a commonly used type, and is, for example, selected from among halo, alkyl, aryl, and arylalkyl.

In the method for producing a carbonate compound of the present invention, for example, a starting material is reacted with a fluorinating agent under a reaction solvent and an oxygen atmosphere to synthesize a predetermined carbonate compound, the reaction solvent using water alone, and the fluorinating agent reacting with a nitrogen cation It is characterized by being a compound composed of halide anions, and in this case, the reaction environment is improved by the use of water, and the reaction stability is excellent, while the reaction time is shortened compared to the prior art, and side reactions are reduced, providing improved yield. .

In the present description, unless otherwise specified, the starting material may be at least one selected from compounds represented by Formula 1 described below.

In the present description, the material produced from the starting material may be at least one selected from compounds represented by Formula 2 described below, unless otherwise specified.

Hereinafter, each component necessary for manufacturing the carbonate compound of the present invention will be described in detail.

starting material

The starting material used in the fluorine substitution reaction in the present description may be, for example, a compound represented by Formula 1 below.

[Formula 1]

In Formula 1, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0, R ₁ is Hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least one carbon atom can include

In addition, in Formula 1, X ₂ and X ₂ 'are each independently a bond, oxygen or methylene, and R ₂ and R ₂ 'are each independently hydrogen, substituted or unsubstituted alkylenyl having 1 to 10 carbon atoms. can

In Formula 1, for example, when each of X ₁ and X ₁ 'is oxygen, n is 0, and R ₁ and R ₁ ' may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 1, for example, when X ₁ and X ₁ 'are each oxygen, n is an integer of 1 to 4, and R ₁ and R ₁ ' may be substituted or unsubstituted alkylene having 1 to 10 carbon atoms, respectively. .

In Formula 1, for example, when each of X ₁ and X ₁ 'is methylene, n is 0, and R ₁ and R ₁ ' may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 1, for example, when X ₁ and X ₁ 'are each methylene, n is an integer of 1 to 4, and R ₁ and R ₁ 'may be substituted or unsubstituted alkylene having 1 to 10 carbon atoms, respectively. .

In Formula 1, for example, when X ₁ and X ₁ 'are each a bond, n is 0, and R ₁ and R ₁ ' may each be a substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 1, for example, when X ₁ and X ₁ 'are each a bond, n is an integer of 1 to 4, and R ₁ and R ₁ ' may each be a substituted or unsubstituted alkylene having 1 to 10 carbon atoms. .

In Formula 1, for example, when X ₁ is methylene and X ₁ ′ is oxygen, n is 0, and R ₁ and R ₁ ′ may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 1, for example, when X ₁ is methylene and X ₁ 'is oxygen, n is an integer of 1 to 4, and R ₁ and R ₁ 'are each independently bonded or substituted or unsubstituted carbon atoms 1 to 10 It may be an alkylene of

As a specific example, the compound represented by Formula 1 may be a compound represented by Formula 4 below.

[Formula 4]

product

A product prepared by using the compound represented by Chemical Formula 1 described above in the fluorine substitution reaction in the present description may be, for example, a compound represented by Chemical Formula 2 below.

[Formula 2]

In Formula 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0, R ₁ is Hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least one carbon atom can include

In Formula 2, X ₂ and X ₂ 'are each independently a bond, oxygen or methylene, and R ₂ and R ₂ 'are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms. am.

In Formula 2, for example, when each of X ₁ and X ₁ 'is oxygen, n is 0, and R ₁ and R ₁ ' may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 2, for example, when X ₁ and X ₁ 'are each oxygen, n is an integer of 1 to 4, and R ₁ and R ₁ ' may each be a substituted or unsubstituted alkylene having 1 to 10 carbon atoms. .

In Chemical Formula 2, for example, when each of X ₁ and X ₁ 'is methylene, n is 0, and R ₁ and R ₁ ' may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 2, for example, when X ₁ and X ₁ 'are each methylene, n is an integer of 1 to 4, and R ₁ and R ₁ 'may be substituted or unsubstituted alkylene having 1 to 10 carbon atoms, respectively. .

In Formula 2, for example, when each of X ₁ and X ₁ 'is a bond, n is 0, and R ₁ and R ₁ ' may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 2, for example, when X ₁ and X ₁ 'are each a bond, n is an integer of 1 to 4, and R ₁ and R ₁ 'may be substituted or unsubstituted alkylene having 1 to 10 carbon atoms, respectively. .

In Formula 2, for example, when X ₁ is methylene and X ₁ ′ is oxygen, n is 0, and R ₁ and R ₁ ′ may each be substituted or unsubstituted alkylene having 1 to 10 carbon atoms.

In Formula 2, for example, when X ₁ is methylene and X ₁ 'is oxygen, n is an integer of 1 to 4, and R ₁ and R ₁ 'are each independently bonded or substituted or unsubstituted carbon atoms 1 to 10 It may be an alkylene of

As a specific example, the compound represented by Formula 2 may be a compound represented by Formula 5 below.

[Formula 5]

Fluorine substitution reaction

The manufacturing method according to the present description aims to obtain the compound represented by the above formula (2) by a fluorine substitution reaction using the compound represented by the above formula (1) as a starting material.

The fluorine substitution reaction of the present description can use water alone as a reaction solvent by specifying the order of input of components, the type of components and reaction conditions, thereby improving the reaction environment and providing a method for producing a carbonate compound capable of realizing reaction stability effect will be provided.

Hereinafter, after examining the fluorinating agent used in the fluorine substitution reaction, the specific conditions and changes over time of the fluorine substitution reaction using the same are sequentially examined.

Fluorine displacement reaction fluorinating agent

The fluorinating agent that performs the above-mentioned fluorine substitution reaction may be a compound containing a cation represented by Formula 3 and a halogen anion.

[Formula 3]

In Chemical Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and may contain at least 1 carbon atom.

An example of a suitable fluorinating agent may be, for example, tetrabutylammonium fluoride. In this case, water can be used as a reaction solvent, which not only improves the reaction environment, but also has excellent reaction stability, shortens the reaction time compared to the prior art, and reduces side reactions. There is an effect that can provide improved output with a small amount.

The halogen anion may be a fluoride ion.

The input amount of the fluorinating agent is, for example, 2 to 4 equivalents, 2 to 3 equivalents, or 3 to 4 equivalents based on 1 equivalent of the compound represented by Formula 1. The reaction conversion rate and reaction rate can be optimized. .

Reaction solvent for fluorine displacement reaction

In organic reactions including the aforementioned fluorine substitution reaction, the solvent effect is very important, and even if all other conditions are the same, some reactions may not proceed depending on the solvent, and some reactions may proceed almost 100%. Therefore, in the method for preparing the carbonate compound according to the present description, the selection of the reaction solvent is very important.

Since the reaction solvent should be able to easily control or handle the reaction environment while dissolving the compound represented by Formula 1 as a starting material, preferably water is used to improve production efficiency, and a fluorinating agent and a solvent are used together, Problems occurring when a solvent is not used can be minimized.

The amount of water used is, for example, 300 to 500 parts by weight, or 400 to 500 parts by weight based on 100 parts by weight of the compound represented by Formula 1. It is preferable to optimize the reaction conversion rate and purity.

Conditions of fluorine substitution reaction and change over time

The use of the fluorinating agent in a solid state is suitable for imparting reaction stability.

At this time, the reaction temperature of the fluorine substitution reaction is, for example, 40 to 100 ℃, or 80 to 100 ℃ can exert the optimal effect.

The reaction temperature during the synthesis is, for example, 40 to 60 ℃, 40 to 50 ℃ to react

The reaction time may be, for example, 12 hours or less, preferably 10 hours or less, and more preferably 8 hours or less.

On the other hand, the pH of the reaction during the synthesis is preferably controlled to, for example, 7 to 9, preferably 7.5 to 8, and more preferably 7.6 to 7.9 using the above-described pH adjusting agent to optimize reaction efficiency.

In the present description, pH can be measured by a measurement method commonly used in the art to which the present invention belongs.

A method for preparing a carbonate compound according to the present disclosure includes, for example, preparing a reactant solution by mixing the reaction solvent and the compound represented by Formula 1; Injecting a fluorinating agent into the reactant solution; And it is characterized in that the reactant solution into which the fluorinating agent is introduced is maintained at 25 to 30 ° C. under an oxygen atmosphere, and in this case, water is used as a reaction solvent to improve the reaction environment, while the reaction stability is excellent and the reaction time compared to the prior art This is shortened, and side reactions are reduced, which has the effect of providing improved yield.

In fact, according to the method for producing a carbonate compound according to the present description, the purity of the compound represented by Formula 2 within 8 hours of reaction time is, for example, 90% by weight or more, preferably 95% by weight or more, more preferably 99% by weight or more, and most preferably 100% by weight.

In addition, according to the method for producing a carbonate compound according to the present disclosure, the yield of the compound represented by Formula 2 within 6 hours of the reaction time is, for example, 40% by weight or more, preferably 43% by weight or more, more preferably 45% by weight or more, more preferably 47% by weight or more, and most preferably 50% by weight or more.

After reacting for 8 hours according to the method for producing a carbonate compound according to the present description, the reaction was terminated, and it can be seen that the purity of the product as measured by gas chromatography was 99%.

In addition, according to the preparation method of the present disclosure, as described above, a product is obtained with a high purity of 100% by weight or close to 100% by weight and does not contain insoluble impurities, so there is no post-process such as filter treatment or filtrate purification. ) can be added to terminate the reaction. At this time, ammonium chloride may be used as the reaction termination reagent.

According to another embodiment of the present invention, injecting a fluorinating agent into the reaction vessel; sequentially introducing a reaction solvent and a compound represented by Formula 1 into the reaction vessel; synthesizing a compound represented by Formula 2 by maintaining the reaction vessel at 25 to 30° C. under an oxygen atmosphere; and distilling and purifying the supernatant after layer separation of the compound represented by Formula 2, wherein water is used as the reaction solvent alone, and the fluorinating agent is a cation represented by Formula 3 below and a halogen. It provides a method for producing a carbonate compound, characterized in that a compound containing an anion is used as a solid phase.

[Formula 1]

[Formula 2]

(In Formulas 1 and 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0 R ₁ is hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least contains one or more carbons.)

[Formula 3]

(In Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and containing at least 1 carbon atom.)

In this description, the weight ratio of the reaction solvent, the reaction conditions, and the content of the fluorinating agent are the same as those described above, so repeated description is omitted.

Hereinafter, preferred embodiments are presented to aid understanding of the present invention, but the following examples are merely illustrative of the present invention, and various changes and modifications are possible within the scope and spirit of the present invention. It is obvious to those skilled in the art, It goes without saying that these variations and modifications fall within the scope of the appended claims.

[Example]

Example 1

A thermometer was installed in a 2L four-necked reaction vessel, 380 g of tetrabutylammonium fluoride trihydrate (Bu ₄ NF.3H ₂ O) was added as a solid phase as a fluorinating agent, and then 1228 g of water was added and a compound represented by Formula 4 ( Hereinafter, also referred to as 'starting material') 50 g was added.

[Formula 4]

The temperature of the reaction solution was maintained at 40 to 60° C. under an oxidizing atmosphere.

As a reaction termination reagent, 3 equivalents of ammonium chloride based on 1 equivalent of the starting material were added, stirred for 30 to 60 minutes, and then layer separation was performed. The separated filtrate was filtered using a celite filter, and the reaction solution was concentrated to obtain a liquid product, and the calculated yield was 53% by weight.

In addition, as a result of ¹ H-NMR analysis of the product, it was confirmed that the product was a compound represented by Formula 4 (see FIG. 1).

¹ H-NMR (400 MHz, CDCl ₃ ) δ 6.38-6.21 (m, 1H), 4.65-4.59 (m, 1H), 4.56-4.53 (m, 1H), HRMS m/z : [M] ⁺ calcd for C ₃ H ₃ FO ₃ 106.0066; Found 106.0065

Subsequently, the product was obtained after vacuum drying at 40 ° C., gas chromatography was performed, and the purity of the compound represented by Formula 5 (hereinafter referred to as the product) was confirmed to be 99% by weight.

[Formula 5]

Example 2

A thermometer was installed in a 5L four-necked reaction vessel, 400 g of tetrabutylammonium fluoride trihydrate (Bu ₄ NF.3H ₂ O) was added as a solid phase as a fluorinating agent, and then 2040 g of water was added and the starting material (represented by Formula 4) Compound) 50 g was added.

The temperature of the reaction solution was maintained at 60 to 100° C. under an oxidizing atmosphere.

As a reaction termination reagent, 3 equivalents of ammonium chloride based on 1 equivalent of the starting material were added, stirred for 30 to 60 minutes, and then layer separation was performed. The separated filtrate was filtered using a celite filter, and the reaction solution was concentrated to obtain a liquid product, and the yield was calculated to be 48% by weight.

Then, after vacuum drying at 40 ° C., the product was obtained, gas chromatography was performed, and the purity of the product (compound represented by Formula 5) was confirmed to be 99% by weight.

Comparative Example 1

The same process as in Example 1 was performed except that the fluorinating agent used in Example 1 was replaced with SbF ₃ and the reaction was performed in a nitrogen atmosphere.

During the process, it was confirmed that the fluorinating agent contacted water used as a solvent in Example 1 as a solvent to form hydrogen fluoride, and the reaction was stopped due to danger in use.

Comparative Example 2

The same process as in Example 1 was repeated, except that 57 g of the compound represented by Formula 6 was used instead of 50 g of the compound represented by Formula 3 as a starting material in Example 1.

[Formula 6]

As a reaction termination reagent, 3 equivalents of ammonium chloride based on 1 equivalent of the starting material were added, stirred for 30 to 60 minutes, and then layer separation was performed. The separated filtrate was filtered using a celite filter, and the reaction solution was concentrated to obtain a liquid product, and the yield was calculated to be 38% by weight.

Subsequently, the product was obtained after vacuum drying at 40 ° C., gas chromatography was performed, and the purity of the compound represented by the following formula (7) (hereinafter referred to as the product) was confirmed to be 90% by weight.

[Formula 7]

Compared to Example 1, in the case of Comparative Example 2 in which an appropriate kind of starting material was not used even though the same reaction solvent was used, it was found that it was difficult to apply an efficient reaction mechanism and the yield was reduced to 40% or less.

Comparative Example 3

The same process as in Example 1 was repeated, except that the fluorinating agent used in Example 1 was used in a liquid phase instead of a solid phase.

As a reaction termination reagent, 3 equivalents of ammonium chloride based on 1 equivalent of the starting material were added, stirred for 30 to 60 minutes, and then layer separation was performed. The separated filtrate was filtered using a celite filter, and the reaction solution was concentrated to obtain a liquid product, and the yield was calculated to be 48% by weight.

Subsequently, the product was obtained after vacuum drying at 40 ° C., gas chromatography was performed, and the purity of the product (compound represented by Formula 5) was confirmed to be 99% by weight.

Compared to Example 1, in the case of Comparative Example 3 in which an appropriate form was not used even though the same fluorination agent was used, it was found that it was difficult to implement an efficient reaction mechanism and the yield was reduced to 50% or less.

In conclusion, a starting material is reacted with a predetermined fluorinating agent under a reaction solvent and an oxygen atmosphere to synthesize a predetermined carbonate compound, using water alone as the reaction solvent and using water when the fluorinating agent is used in a solid phase In addition to improving the reaction environment, it was confirmed that the reaction stability was excellent, the reaction time was shortened compared to the prior art, and the side reaction was small, so that improved yield could be provided.

Claims (11)

Under a reaction solvent and oxygen atmosphere, the compound represented by the following formula (1) and a fluorinating agent are reacted to synthesize the compound represented by the formula (2),
The reaction solvent is water alone,
The fluorinating agent is a method for producing a carbonate compound, characterized in that using a compound containing a cation represented by the formula (3) and a halogen anion in a solid phase.
[Formula 1]

[Formula 2]

(In Formulas 1 and 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0 R ₁ is hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least contains one or more carbons.)
[Formula 3]

(In Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and containing at least 1 carbon atom.) According to claim 1,
The method for producing a carbonate compound, characterized in that the halogen anion is a fluoride ion. According to claim 1,
The water is a method for producing a carbonate compound, characterized in that added in 300 to 500 parts by weight based on 100 parts by weight of the compound represented by Formula 1. According to claim 1,
The fluorinating agent is a method for producing a carbonate compound, characterized in that added in 2 to 4 equivalents based on 1 equivalent of the compound represented by Formula 1. According to claim 1,
The reaction temperature during the reaction is a method for producing a carbonate compound, characterized in that 40 to 60 ℃. According to claim 1,
preparing a reactant solution by mixing the reaction solvent and the compound represented by Formula 1; Injecting a fluorinating agent into the reactant solution; and maintaining the reactant solution into which the fluorinating agent is introduced at 25 to 30° C. under an oxygen atmosphere. According to claim 1,
The compound represented by Formula 1 is a compound represented by Formula 4, and the compound represented by Formula 2 is a method for producing a carbonate compound, characterized in that a compound represented by Formula 5 below.
[Formula 4]

[Formula 5]

According to claim 1,
The method for producing a carbonate compound, characterized in that the fluorinating agent is tetrabutylammonium fluoride hydrate. According to claim 1,
The reaction is a method for producing a carbonate compound, characterized in that terminated by introducing a quench reagent. According to claim 9,
The method for producing a carbonate compound, characterized in that the termination reagent is ammonium chloride. Injecting a fluorinating agent into a reaction vessel;
sequentially introducing a reaction solvent and a compound represented by Formula 1 into the reaction vessel;
synthesizing a compound represented by Formula 2 by maintaining the reaction vessel at 25 to 30° C. under an oxygen atmosphere; and
Including; separating the layers of the compound represented by Formula 2 and then purifying the supernatant by distillation,
The reaction solvent is water alone,
The fluorinating agent is a method for producing a carbonate compound, characterized in that using a compound containing a cation represented by the formula (3) and a halogen anion in a solid phase.
[Formula 1]

[Formula 2]

(In Formulas 1 and 2, A is C=O, X ₁ , and X ₁ 'are each independently a bond, oxygen or methylene, n is an integer from 0 to 4, and when n is 0 R ₁ is hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and when n is an integer of 1 to 4, R ₁ is a bond, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and at least contains one or more carbons.)
[Formula 3]

(In Formula 3, R ₁ , R ₂ , R ₃ and R ₄ are each independently hydrogen, substituted or unsubstituted alkylene having 1 to 10 carbon atoms, and containing at least 1 carbon atom.)

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