TWI415836B - A process for preparing an alkyl diol alkyl ether (meth) acrylate - Google Patents

Abstract

A method of preparing alkylene glycol alkyl ether (meth)acrylate ester comprises continuously feeding a starting material containing a (meth)acrylic acid, an alcohol ether compound component, and a polymerization inhibitor component into a fixed catalyst bed reactor to carry out esterification to obtain a reaction mixture; using an extractant component to perform extraction on the reaction mixture so as to obtain a crude product and a reaction residue containing the starting material; mixing the crude product with a polymerization inhibitor component and performing distillation to obtain the alkylene glycol alkyl ether (meth)acrylate ester. The preparation method can achieve continuous production and extraction, increased production efficiency and enhanced yield.

Description

Method for preparing alkyl glycol alkyl ether (meth) acrylate

The present invention relates to a process for preparing a (meth) acrylate, and more particularly to a process for preparing an alkyl diol alkyl ether (meth) acrylate.

The (meth) acrylate monomer is widely used industrially, and can be applied to various plasticizers, herbicides, and adhesives in addition to various (meth) acrylate polymers. The preparation method of the general (meth) acrylate monomer sequentially includes the following steps: an esterification reaction step, a vacuum desolvation step, and a vacuum purification step. In the past, when sulfuric acid was used as the esterification reaction catalyst, the color of the crude product obtained was black, and the vacuum purification step was further required. Therefore, the production process was long and the production efficiency was low; With the progress of the polymerization reaction, unnecessary by-products are formed, resulting in a low yield, making the process unsuitable for the industry.

CN101104586A discloses a process for the preparation of a continuous process acrylate. The step of the process comprises (1) subjecting a starting material comprising a high boiling acid component and a C ₅ -C ₈ aliphatic alcohol or an alicyclic alcohol to an esterification reaction; (2) introducing the esterified reaction mixture into a low The boiling separation column is subjected to a distillation treatment to obtain a crude acrylate; (3) the crude acrylate is introduced into a refining column to obtain a purified acrylate; and (4) a bottom liquid is obtained at the bottom of the refining tower, and the The bottom liquid is poured into a high boiling separation column for recycling. This patent passes through the use of a low boiling separation column and a high boiling separation column, and it is expected to improve the problems of low productivity and poor production efficiency in the prior art process. However, since the preparation method is easily accompanied by the progress of the polymerization reaction, the problem of low yield cannot be effectively solved.

When the above acrylate process is applied to the preparation of alkyl glycol alkyl ether (meth) acrylate, the azeotropic temperature of the reaction mixture after esterification is high, which makes the process cost increase, time-consuming and energy-consuming, and equipment selection. It will be limited and does not meet the needs of the industry.

A prior art process for preparing alkyl glycol alkyl ether (meth) acrylates, such as CN 101607901 A, discloses a process for the preparation of a batch process of methoxyethyl acrylate. The method comprises the steps of: (1) subjecting a starting material comprising p-toluenesulfonic acid to an esterification step; (2) performing a water washing step with brine, alkali water and water; and (3) removing the solvent under reduced pressure. . By using p-toluenesulfonic acid as an esterification reaction catalyst, the patent can lighten the color of the crude product without the need for a vacuum purification step, and can improve the problems of long production time and low production efficiency of the conventional production process. However, this method has problems in that it is difficult to mass-produce, and the salt water and alkaline water used in the water washing step may cause the following problems: corrosion of equipment, loss of starting materials, and difficulty in increasing wastewater treatment.

CN100402484C discloses a process for the preparation of a batch process of (meth) acrylate. The method comprises the steps of: (1) pre-reflowing the starting material comprising the polymerization inhibitor; (2) adding the (meth)acrylic acid in batches or adding the esterification reaction; (3) using alkali Water and water are washed with water and neutralized; and (4) a product obtained by the step (3) is added with a polymerization inhibitor. The patent passes through the pre-reflow treatment step, and the use of the polymerization inhibitor and the polymerization inhibitor to eliminate free radicals contained in the starting materials and reduce the probability of polymerization. However, this method has problems in that it is difficult to mass-produce and that alkaline water is used.

In order to effectively reduce process cost or production cost, the production efficiency and yield of the method for preparing (meth) acrylate monomer [especially alkyl diol alkyl ether (meth) acrylate] are increasingly required. High, and in view of the above, there is still a need to develop a process for preparing (meth) acrylate monomers which can be continuously produced and continuously extracted while improving production efficiency and productivity.

Accordingly, it is an object of the present invention to provide a process for the preparation of alkyl glycol alkyl ether (meth) acrylates which can be continuously produced and continuously extracted, and which can increase production efficiency and productivity.

Thus, the process for preparing an alkyl glycol alkyl ether (meth) acrylate according to the present invention comprises: comprising a starting material comprising a (meth)acrylic acid, an alcohol ether compound component and a polymerization inhibitor component Continuously feeding a fixed catalyst bed reactor for esterification to obtain a reaction mixture; extracting the reaction mixture with an extractant component to obtain a crude reaction product (crude reaction product) And a reaction residue containing the starting material; and mixing the crude reaction product and a polymerization inhibitor component and subjecting to distillation to obtain the alkyl glycol alkyl ether (methyl group) )Acrylate.

The invention has the advantages that the preparation method can continuously and continuously prepare the product through the use of the fixed catalytic bed reactor, thereby improving the production efficiency, and the product can be separated from the unreacted starting material by the extraction step, thereby avoiding Or reduce unnecessary by-products (such as oligomers), increase production yield and save on manufacturing costs.

The above "(meth)acrylic acid" means acrylic acid or methacrylic acid.

The method for preparing an alkyl glycol alkyl ether (meth) acrylate according to the invention comprises: continuously feeding a starting material comprising a (meth)acrylic acid, an alcohol ether compound component and a polymerization inhibitor component a fixed catalytic bed reactor for esterification to obtain a reaction mixture; the extract mixture is subjected to extraction treatment with an extractant component to obtain a crude reaction product, and a reaction residue containing the starting material; And the crude reaction product and a polymerization inhibitor component are mixed and subjected to distillation treatment to obtain the alkyl glycol alkyl ether (meth) acrylate.

The fixed catalytic bed reactor of the present invention is not particularly limited in construction, and can be generally used as long as the solid catalyst can be fixed or filled on the reactor.

Compared with the conventional processes such as CN101607901A and CN100402484C, the batch process is a single esterification reaction and a single extraction process, and the extraction process needs to be left to be layered before the subsequent treatment; the preparation method of the present invention is one. The continuous operation process, that is, the continuous raw material can be continuously supplied for esterification reaction, and the reaction mixture after the reaction can be continuously subjected to extraction treatment. Therefore, the method of the present invention has a short time required for the whole process, and does not need to be left to be layered after the extraction treatment, and then subjected to subsequent treatment, thereby being a mass production method and improving production efficiency; The solid catalyst of the preparation method is fixed in the reactor, so that the solid catalyst and the reaction mixture can be separated without increasing the filtration step after the reaction, and at the same time, the solid catalyst does not cause each other during the esterification reaction. The collision causes cracking, so that the blockage of the pipeline can be avoided, and the solid catalyst of the method of the invention can be recycled and reused after the reaction, which meets the requirements of the green environmental protection process.

When an alkyl glycol alkyl ether (meth) acrylate is prepared by a method using a (meth) acrylate such as CN101104586, since CN101104586 directly purifies the reaction mixture by distillation, it is required in the distillation process. Continuous heating and reflux to obtain a high-purity product, but this process causes unreacted starting materials [such as (meth)acrylic acid, alcohol ether compounds] or products to be polymerized with each other, resulting in a decrease in yield while producing Unnecessary by-products. In contrast, the present invention separates the product from the unreacted starting materials and the like by the extraction treatment, thereby reducing the polymerization of the unreacted starting materials or products, thereby increasing the yield. Preferably, the extraction treatment has an operating temperature in the range of from 15 °C to 250 °C. When the extraction treatment is carried out at a low temperature, the extraction partition coefficient can be increased, and the unreacted starting materials or products can be reduced from each other to increase the yield. Furthermore, the reaction mixture disclosed in CN101104586 is a mixture having a low azeotrope, which can be directly passed through the distillation treatment to obtain a crude reaction product; and the reaction mixture of the present invention is a mixture having a high azeotrope, if directly introduced into the distillation apparatus, Increasing the distillation temperature or lowering the distillation pressure will increase the process cost and consume energy. At the same time, the use limit of the equipment needs to be further considered to prevent the equipment from being able to withstand excessive temperature and excessive pressure. Therefore, the present invention introduces an extraction treatment. In addition to increasing the yield, the manufacturing cost can also be reduced.

Preferably, the glycol ether compound component is selected from the group consisting of a propylene glycol monomethyl ether compound, a dipropylene glycol monomethyl ether compound or a tripropylene glycol. a compound of the formula (tripropylene glycol monomethyl ether).

Preferably, the propylene glycol methyl ether compound is selected from the group consisting of 1-methoxy-2-propanol, 2-methoxy-1-propanol, or a combination thereof.

Preferably, the dipropylene glycol methyl ether compound is selected from the group consisting of 1-(2-methoxy-1-methylethoxy)-2-propanol and 2-(2-methoxy-1- Methyl ethoxy)-1-propanol, 1-(1-methoxy-1-methylethoxy)-2-propanol, 2-(1-methoxy-1-methylethoxyl Base)-1-propanol, or a combination of these.

Preferably, the tripropylene glycol methyl ether compound is selected from 1-[2-(2-methoxy.yl-1-methylethoxy)-1-methylethoxy]-2-propane Alcohol, 2-[2-(2-methoxy-1-methylethoxy)-1-methylethoxy]-1-propanol, 1-[1-(2-methoxy-1) -methylethoxy)-1-methylethoxy]-2-propanol, 2-[1-(2-methoxy-1-methylethoxy)-1-methylethoxy 1--1-propanol, 1-[2-(1-methoxy-1-methylethoxy)-1-methylethoxy]-2-propanol, 2-[2-(1- Methoxy-1-methylethoxy)-1-methylethoxy]-1-propanol, 1-[1-(1-methoxy-1-methylethoxy)-1- Methyl ethoxy]-2-propanol, 2-[1-(1-methoxy-1-methylethoxy)-1-methylethoxy]-1-propanol, or such A combination.

Preferably, the polymerization inhibitor component is selected from the group consisting of phenol-based compounds, phenylamine compounds, piperidinyloxy compounds, copper sources, and iron sources. , 铈 source, phenothiazine (10H-phenothiazine), 2-butanone oxime, triethyl phosphite, sulfur powder, or a combination thereof.

The phenolic compound includes, but is not limited to, bisphenol A or a compound represented by the following formula (I). The compound represented by the formula (I):

In the formula (I), R ¹ , R ¹¹ , R ¹² , R ¹³ and R ¹⁴ are each the same or different and represent an alkyl group of H, OH, OR ¹⁵ , NH ₂ , COOH or C ₁ to C ₆ , Wherein R ¹⁵ represents a C ₁ -C ₆ alkyl group. Preferably, the phenolic compound is selected from the group consisting of hydroquinone, 4-methoxyphenol, 2-methoxy-4-methylphenol, bisphenol A, or a combination thereof.

The aniline compound includes, but is not limited to, a compound represented by the following formula (II). The compound represented by the formula (II):

In the formula (II), R ² , R ²¹ , R ²² , R ²³ and R ²⁴ are respectively the same or different and each represents an alkyl group of H, -NR ²⁵ R ²⁶ or C ₁ -C ₆ wherein R ²⁵ Or R ²⁶ are respectively the same or different and each represents hydrogen or a C ₁ -C ₆ alkyl group. Preferably, the aniline compound is selected from the group consisting of p-phenylenediamine, nitrogen, nitrogen-dimethyl-p-phenylenediamine, nitrogen, nitrogen-diethyl-p-phenylenediamine, nitrogen, nitrogen-dipropyl. - p-phenylenediamine, nitrogen, nitrogen-dibutyl-p-phenylenediamine, nitrogen, nitrogen-dipentyl-p-phenylenediamine, nitrogen, nitrogen-dihexyl-p-phenylenediamine, or a combination thereof .

Preferably, the nitroxide piperidine is selected from 4-hydroxy-2,2,6,6-tetramethylpiperidine nitrogen-oxyl radical (4-hydroxy-2,2,6, 6-tetramethyl-piperidinyloxy), 4-oxo-2,2,6,6-tetramethyl-piperidinyloxy, (4-oxo-2,2,6,6-tetramethyl-piperidinyloxy), 4- -acetate-2,2,6,6-tetramethyl-piperidinyloxy, 2,2,6,6-tetramethyl - piperidine nitroxide (2,2,6,6-tetramethyl-piperidinyloxy), or a combination thereof.

Preferably, the copper source is selected from copper chloride (CuCl) or copper trichloride (CuCl ₂ ).

Preferably, the iron source is selected from iron dichloride (FeCl ₂ ) or iron trichloride (FeCl ₃ ).

Preferably, the source of germanium is cerium (III) acetate.

Preferably, the solid catalyst in the fixed catalytic bed reactor is an acidic cationic exchange resin. Preferably, the acidic cationic exchange resin is an acidic cationic exchange resin having a benzenesulfonate. The acid-cationic exchange resin having a benzenesulfonate group includes, but is not limited to, Duolite C-26C (manufactured by ROHM & HAAS), DIAION PK-208 (manufactured by Mitsubishi Chemistry), SPC-108 (manufactured by Bayer), and DOWEX MSC-1 (Dow). , or Amberlyst-15, Amberlyst-36, Amberlyst-39, Amberlyst-70, etc. made by ROHM & HAAS. In the past, catalysts such as p-toluenesulfonic acid or methanesulfonic acid, such as p-toluenesulfonic acid or methanesulfonic acid, decompose and release sulfur dioxide at high temperatures, and the sulfur dioxide induces polymerization, resulting in unnecessary by-product formation. The solid catalyst used in the fixed catalytic bed reactor of the present invention is relatively stable at high temperatures.

Preferably, in the starting material, the molar ratio of the (meth)acrylic acid to the alcohol ether compound ranges from 0.5 to 5. Preferably, the polymerization inhibitor component is present in an amount ranging from 20 ppm to 2,000 ppm based on the total amount of the (meth)acrylic acid of 1 mole.

Preferably, the esterification reaction has an operating temperature in the range of from 15 °C to 250 °C. Preferably, the esterification reaction has an operating time ranging from 2 minutes to 480 minutes.

Preferably, the extractant component is an alkyl acetate compound selected from C ₂ to C ₁₈ , a C ₁ - C ₂₀ saturated alkane compound, and a C ₁ - C ₁₀ at least one chlorine substituted alkane. a compound, a C ₅ - C ₂₀ alicyclic hydrocarbon compound, a C ₆ - C ₂₀ aromatic hydrocarbon compound, a compound of the formula C _m H _{2m + n} O _n , or a combination thereof; m represents an integer of 0 to 20; n represents an integer of 1 to 5, and m≧n-1. Preferably, the extractant component is contained in an amount ranging from 50 parts by weight to 500 parts by weight based on 100 parts by total of the total amount of the reaction mixture.

The C ₂ -C ₁₈ alkyl acetate compound may be used singly or in combination, and the C ₂ -C ₁₈ alkyl acetate compound includes, but is not limited to, ethyl acetate, n-propyl acetate, and isopropyl acetate. , n-butyl acetate, isobutyl acetate, second butyl acetate or tert-butyl acetate.

The C ₁ - C ₂₀ saturated alkane compound may be used singly or in combination, and the C ₁ - C ₂₀ saturated alkane compound may include, but is not limited to, pentane, hexane, heptane, octane or petroleum ether.

The C ₁ - C ₁₀ at least one chlorine-substituted alkane compound may be used singly or in combination, and the C ₁ - C ₁₀ at least one chlorine-substituted alkane compound includes, but is not limited to, methyl chloride, dichloromethane or trichlorobenzene. Methane, etc.

The C ₅ - C ₂₀ alicyclic hydrocarbon compound may be used singly or in combination, and the C ₅ - C ₂₀ alicyclic hydrocarbon compound may include, but is not limited to, cyclopentane, cyclohexane, cycloheptane or cyclooctane. Wait.

The C ₆ - C ₂₀ aromatic hydrocarbon compound may be used singly or in combination, and the C ₆ - C ₂₀ aromatic hydrocarbon compound may include, but is not limited to, toluene or xylene.

The compound of C _m H _2m+n O _n is selected from the group consisting of C ₁ - C ₂₀ alcohol compounds containing at least one hydroxyl group, C ₂ - C ₂₀ ether compounds containing at least one ether group, and at least one hydroxyl group. And at least one ether group of a C ₂ - C ₂₀ alcohol ether compound, water, or a combination thereof.

The C ₁ - C ₂₀ alcohol compound containing at least one hydroxyl group may be used singly or in combination, and the C ₁ - C ₂₀ alcohol compound containing at least one hydroxyl group includes, but not limited to, ethanol or the like.

The C ₂ - C ₂₀ ether compound containing at least one ether group may be used singly or in combination, and the C ₂ - C ₂₀ ether compound containing at least one ether group includes, but not limited to, methyl isobutyl ether and the like. .

In the past, the extractant component used in CN101607901A and CN100402484C is alkaline water or salt water, which is easy to cause corrosion of equipment or pipeline; in contrast, the extractant component used in the present invention can reduce damage of equipment or pipeline due to corrosion. situation. Considering the current demand for green production capacity, it is necessary to adopt the concept of recycling and recycling of raw materials that have not been reacted in each process. Therefore, if alkaline reagents (such as alkaline water) are used in the past, unreacted raw materials will be consumed [eg ( Methyl)acrylic acid or an alcohol ether compound, etc., cannot be recycled and reused; in contrast, the present invention can effectively recycle unreacted starting materials through the use of the above extracting agent component. Furthermore, the extractant component (alkaline water or brine) used in the past is difficult to recover; in contrast, the extractant component used in the present invention is recyclable, and the process of the present invention does not exist as in the past. There are a lot of problems with wastewater discharge in the system. Therefore, the method of the present invention is a concept of a green process.

Preferably, the distillation treatment has an operating temperature in the range of from 70 °C to 140 °C. Preferably, the distillation process has an operating pressure in the range of 0.1 torr to 760 torr. Preferably, the preparation method further comprises subjecting the reaction residue to a distillation treatment to obtain an unreacted starting material. Preferably, the unreacted starting material is further recovered to the fixed catalytic bed reactor.

A detailed description of a preferred embodiment of the process for preparing an alkyl glycol alkyl ether (meth) acrylate of the present invention is shown in Figure 1: controlling the wall temperature of the fixed catalytic bed reactor 1 to an appropriate temperature The temperature range (15 ° C ~ 250 ° C), and the outlet end pressure is controlled between 1 kg / cm ² ~ 20 kg / cm ² . The starting material of the uniformly mixed (meth)acrylic acid, the alcohol ether compound component and the polymerization inhibitor component is gradually flowed into the fixed catalytic bed reactor 1 and retained for a period of time, and then reacted via a fixed catalyst bed. The outlet of the vessel 1 exits a reaction mixture.

The reaction mixture and the extractant component are continuously introduced into an extraction device 2 for continuous and uninterrupted extraction treatment. The extraction treatment is carried out at a suitable pressure (1 kg/cm ² to 20 kg/cm ² ) and at a temperature to obtain a first component containing an extractant component and a crude reaction product, and A reaction residue containing the starting material. Next, the first component and the polymerization inhibitor are introduced into a first distillation apparatus 3 for distillation treatment. The distillation treatment is carried out under a suitable pressure, and the extractant can be recovered from the top of the first distillation apparatus 3 and introduced into the extraction apparatus 2, and the crude product of the present invention can be obtained at the bottom of the distillation apparatus 3. Next, the crude product of the present invention is further introduced into a rectification unit 4 (e.g., a thin film evaporation tower) for purification, and a polymerization inhibitor component may be optionally added. The reaction residue containing the starting material is introduced into a second distillation apparatus 5, and optionally a polymerization inhibitor component is added, and subjected to distillation dehydration treatment. The distillation dehydration treatment is carried out under a suitable pressure, and the unreacted starting material can be recovered from the bottom of the second distillation apparatus 5 and introduced into the fixed catalytic bed reactor 1 to carry out the esterification reaction again.

The extraction device 2, the first distillation device 3, the rectification device 4, and the second distillation device 5 described above may be generally used, and therefore will not be described again.

<Example>

The preparation system used in the examples is shown in FIG. First, the wall temperature of the fixed catalytic bed reactor 1 was controlled at 120 ° C, and the outlet end pressure was controlled at 1.1 kg / cm ² . The starting material of uniformly mixed 1 mol of acrylic acid, 1.2 mol of 1-methoxy-2-propanol and 0.0016 mol of hydroquinone was slowly flowed into the fixed catalytic bed reactor 1 to be retained. After 5 minutes, a reaction mixture was passed through the outlet of the fixed catalyst bed reactor 1.

The reaction mixture was continuously introduced into an extraction apparatus 2 with 100 parts by weight of toluene and water for continuous and uninterrupted extraction treatment. The extraction treatment is carried out at 1.1 kg/cm ² and room temperature at 25 ° C to obtain a first component containing the extractant component and the crude reaction product, and a reaction residue containing the starting material. Next, the first component and 0.0016 mol of hydroquinone were introduced into a first distillation apparatus 3 for distillation treatment. The distillation treatment is carried out at 0.9 kg/cm ² , the extractant can be recovered from the top of the distillation unit 3 and introduced into the extraction unit 2, and 0.323 mol of crude product can be obtained at the bottom of the distillation unit 3, and the crude product is produced. The rate is 32.3%. Next, the crude product and the polymerization inhibitor component were introduced into a thin film evaporation tower as a rectification apparatus 4, and the yield was 30%. The reaction residue containing the starting material is introduced into a second distillation apparatus 5, and optionally a polymerization inhibitor component is added, and subjected to distillation dehydration treatment. This distillation dehydration treatment was carried out at 0.9 kg/cm ² , and the unreacted starting material was recovered from the bottom of the second distillation apparatus 5, and introduced into the fixed catalyst bed reactor 1 to carry out an esterification reaction again.

In summary, the present invention allows the process to continuously and continuously produce products by using a fixed catalyst bed reactor, thereby improving production efficiency, and separating the product from unreacted starting materials by extraction treatment. To avoid or reduce the formation of unnecessary by-products (such as oligomers) and increase the production yield. Furthermore, the solid catalyst, the extractant component and the unreacted starting materials used in the present invention can be recycled and reused, and at the same time, the extractant component used in the present invention does not cause corrosion of equipment or pipelines, so The object of the invention can be achieved.

The above is only the preferred embodiment of the present invention, and the scope of the invention is not limited thereto, that is, the simple equivalent changes and modifications made by the scope of the invention and the description of the invention are All remain within the scope of the invention patent.

1. . . Fixed catalyst bed reactor

2. . . Extraction device

3. . . First distillation unit

4. . . Distillation unit

5. . . Second distillation unit

BRIEF DESCRIPTION OF THE DRAWINGS Figure 1 is a flow chart showing a preferred embodiment of the process for preparing an alkyl glycol alkyl ether (meth) acrylate of the present invention.

1. . . Fixed catalyst bed reactor

2. . . Extraction device

3. . . First distillation unit

4. . . Distillation unit

5. . . Second distillation unit

Claims (10)

A method for preparing an alkyl glycol alkyl ether (meth) acrylate, comprising: continuously feeding a starting material comprising a (meth)acrylic acid, an alcohol ether compound component and a polymerization inhibitor component a fixed catalytic bed reactor for esterification to obtain a reaction mixture; the extract mixture is subjected to extraction treatment with an extractant component to obtain a crude reaction product, and a reaction residue containing the starting material; And the crude reaction product and a polymerization inhibitor component are mixed and subjected to distillation treatment to obtain the alkyl glycol alkyl ether (meth) acrylate. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to the above patent application, wherein the alcohol ether compound component is selected from a propylene glycol methyl ether compound and a dipropylene glycol methyl group. An ether compound or a tripropylene glycol methyl ether compound. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, wherein the molar ratio of the (meth)acrylic acid to the alcohol ether compound ranges from 0.5 to 5. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, wherein the total amount of the (meth)acrylic acid is 1 mol based on the total amount of the (meth)acrylic acid in the starting material. The inhibitor component has a content ranging from 20 ppm to 2,000 ppm. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, wherein the solid catalyst in the fixed catalytic bed reactor is an acidic cationic exchange resin. A method for producing an alkyl glycol alkyl ether (meth) acrylate according to the above patent application, wherein the polymerization inhibitor component is selected from the group consisting of a phenol compound, an aniline compound, and a nitrogen oxide free A piperidine compound, a copper source, an iron source, a ruthenium source, a phenothiazine, a butanone oxime, a triethyl phosphite, a sulfur powder, or a combination thereof. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, wherein the content of the extractant component is based on 100 parts by weight of the total of the reaction mixture. It is 50 parts by weight to 500 parts by weight. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, wherein the extractant component is an alkyl acetate compound selected from C ₂ to C ₁₈ , saturated alkanes C ₁ ~ C ₂₀ compound, and at least a chloro-substituted the C ₁ ~ C ₁₀ alkyl compound, alicyclic C ₅ ~ C ₂₀ hydrocarbon compounds, aromatic hydrocarbon compounds C ₆ ~ C _20, and The molecular formula is C _m H _2m+n O _n , or a combination thereof; wherein. m represents an integer of 0 to 20; n represents an integer of 1 to 5, and m≧n-1. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 1, further comprising subjecting the reaction residue to a distillation treatment to obtain an unreacted starting material. The method for producing an alkyl glycol alkyl ether (meth) acrylate according to claim 9 of the patent application, further comprising recovering the unreacted starting material into the fixed catalytic bed reactor.