CN112592271A - Method and device for preparing isooctyl acrylate - Google Patents
Method and device for preparing isooctyl acrylate Download PDFInfo
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- CN112592271A CN112592271A CN202011531328.8A CN202011531328A CN112592271A CN 112592271 A CN112592271 A CN 112592271A CN 202011531328 A CN202011531328 A CN 202011531328A CN 112592271 A CN112592271 A CN 112592271A
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- alumina catalyst
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/02—Sulfur, selenium or tellurium; Compounds thereof
- B01J27/053—Sulfates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
- C07C67/62—Use of additives, e.g. for stabilisation
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Abstract
The invention discloses a method and a device for preparing isooctyl acrylate, wherein the method comprises the following steps: carrying out esterification dehydration reaction on acrylic acid and 2-ethylhexanol under the action of a modified alumina catalyst; wherein, the modified alumina catalyst is obtained by modifying an alumina catalyst with sulfate. The aluminum oxide modified by the sulfate is used as a catalyst for the reaction for preparing the isooctyl acrylate, so that the production capacity is greatly improved, and the selectivity of the isooctyl acrylate is greatly improved. And when the fixed bed is adopted for production, the method can realize continuous production, and has the advantages of simple process flow, stable production process, easy control, safe and reliable production, low energy consumption and less wastewater.
Description
Technical Field
The invention relates to the technical field of acrylate synthesis, in particular to a method and a device for preparing isooctyl acrylate.
Background
Isooctyl acrylate, colorless and transparent, is a monomer of high molecular polymer, and is copolymerized with other monomers, crosslinked, grafted and the like to obtain an acrylic resin product which is used for processing synthetic fiber fabrics, adhesives, coatings, plastic modification and other aspects.
The preparation method of isooctyl acrylate is mainly a direct esterification method, namely, acrylic acid and 2-ethylhexanol are esterified by taking sulfuric acid as a catalyst, and then a finished product is obtained by neutralization, dealcoholization and rectification. The direct esterification method is accompanied with a plurality of side reactions in the production process, and in order to reduce the generation of the side reactions, the dehydrating agent is mainly added into a reaction system at present to remove water generated in the reaction in time, and then the dehydrating agent is mostly benzene organic solvent, which is not beneficial to environmental protection and has more complicated post-treatment.
Therefore, a preparation process of isooctyl acrylate with high esterification efficiency, less side reaction and environmental protection is needed.
In view of this, the invention is particularly proposed.
Disclosure of Invention
The object of the present invention is to provide a method and apparatus for producing isooctyl acrylate that ameliorates at least one of the above-mentioned technical problems.
The invention is realized by the following steps:
in a first aspect, the present invention provides a method for preparing isooctyl acrylate comprising: carrying out esterification dehydration reaction on acrylic acid and 2-ethylhexanol under the action of a modified alumina catalyst; wherein, the modified alumina catalyst is obtained by modifying an alumina catalyst with sulfate.
Optionally, the mass percentage content of sulfate ions in the modified alumina catalyst is 1-4%.
Alternatively, the sulfate salt comprises (NH)4)2SO4、Al2(SO4)3And Ti (SO)4)2At least one of (1).
Alternatively, the method of modifying the alumina catalyst with sulfate employs an impregnation method or a coprecipitation method.
Alternatively, the homogeneous mixture of sulfate and alumina is extruded and then calcined.
Optionally, uniformly mixing the aqueous solution of the sulfate and the dispersion liquid of the aluminum oxide into paste, standing at room temperature for 5-8 hours, performing rotary evaporation to obtain a solid, performing extrusion forming, drying, and then roasting; optionally, the rotary evaporation is performed under vacuum conditions; optionally, extruded into a clover shape; optionally, the drying temperature is 110-120 ℃, and the drying time is 2-5 hours.
Optionally, the roasting temperature is 400-450 ℃, and the roasting time is 1.5-3 hours.
Alternatively, the alumina is γ -Al2O3。
Optionally, the esterification dehydration reaction is carried out at a temperature of 70-180 ℃, preferably at a temperature of 80-150 ℃, and more preferably at a temperature of 85-120 ℃.
Optionally, the raw materials are preheated, and then the modified alumina catalyst is added for reaction, wherein the preheating temperature is 70-120 ℃, and the preheating temperature is 95-100 ℃.
Alternatively, acrylic acid and 2-ethylhexanol in a molar ratio of 1: 1.2-1.5;
optionally, a polymerization inhibitor is added to the raw materials for the esterification dehydration reaction; optionally, the addition amount of the polymerization inhibitor is 0.1-0.3% of the weight of the acrylic acid, and optionally, the polymerization inhibitor is phenothiazine.
Alternatively, the esterification dehydration reaction is carried out in a fixed bed reactor packed with the modified alumina catalyst.
Optionally, the method further comprises the steps of sequentially neutralizing, dealcoholizing and rectifying the product after the esterification dehydration reaction.
In a second aspect, the invention also provides a device for preparing isooctyl acrylate, which comprises a fixed bed reactor, wherein a bed layer of a modified alumina catalyst is filled in the fixed bed reactor, the modified alumina catalyst is obtained by modifying the alumina catalyst with sulfate, and the fixed bed reactor is also provided with a raw material inlet and a product outlet for introducing acrylic acid and 2-ethylhexanol;
optionally, the fixed bed reactor is a vertically arranged tubular reactor, the raw material inlet is arranged above the bed layer of the filled modified alumina catalyst, the product outlet is arranged below the bed layer of the modified alumina catalyst in the fixed bed reactor, and the top of the fixed bed reactor is also provided with a steam outlet.
Optionally, the apparatus further comprises: the acrylic acid feeding container, the 2-ethylhexanol feeding container, the polymerization inhibitor feeding container and the raw material mixing container are communicated with the raw material mixing container respectively, and the raw material mixing container is communicated with the raw material inlet.
Optionally, a preheating tower is further arranged between the raw material inlet and the raw material mixing container.
Optionally, the water vapor outlet is also communicated with a condenser.
The technical scheme of the invention has the following beneficial effects: the aluminum oxide modified by the sulfate is used as a catalyst for the reaction for preparing the isooctyl acrylate, so that the production capacity is greatly improved, and the selectivity of the isooctyl acrylate is greatly improved. And when the fixed bed is adopted for production, the method can realize continuous production, and has the advantages of simple process flow, stable production process, easy control, safe and reliable production, low energy consumption and less wastewater.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
Fig. 1 is a schematic view of an apparatus for preparing isooctyl acrylate according to an embodiment of the present invention.
Icon: 1-an acrylic acid charging vessel; a 2-2-ethylhexanol addition vessel; 3-a polymerization inhibitor feeding container; 4-raw material mixer; 5-a delivery pump; 6-preheating tower; 7-fixed bed reactor; 8-a condenser.
Detailed Description
In order to make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. The examples, in which specific conditions are not specified, were conducted under conventional conditions or conditions recommended by the manufacturer. The reagents or instruments used are not indicated by the manufacturer, and are all conventional products available commercially.
The following is a detailed description of a method and apparatus for preparing isooctyl acrylate according to the present invention.
Some embodiments of the present invention provide a method of making isooctyl acrylate comprising: carrying out esterification dehydration reaction on acrylic acid and 2-ethylhexanol under the action of a modified alumina catalyst; wherein, the modified alumina catalyst is obtained by modifying an alumina catalyst with sulfate.
The inventor finds that the existing sulfuric acid catalyst is liquid, so that the existing sulfuric acid catalyst can only adopt a direct esterification method, various side reactions are generated in the production process, and although the problem can be solved to a certain extent by adding the dehydrating agent, the problem of pollution caused by the dehydrating agent is not easy to ignore. Therefore, the inventors have creatively proposed, through a great deal of practice and research, that a modified alumina catalyst obtained by modifying an alumina catalyst with a sulfate is applied to a reaction process for preparing isooctyl acrylate, and have creatively found that the use of the modified alumina catalyst can effectively improve the conversion rate and the selectivity to isooctyl acrylate.
Specifically, in order to enable good pertinence to preparation of isooctyl acrylate, the mass percentage content of sulfate ions in the modified alumina catalyst is 1-4%. In some embodiments, the alumina is γ -Al2O3。
That is, the catalyst of the embodiment of the present invention is on ordinary γ -Al2O3Modified by using gamma-Al2O3Adding appropriate sulfate to make SO4 2-Adding gamma-Al2O3To produce a medium strength acidity. Using a suitable sulfate as a modifying component for gamma-Al2O3Is modified, SO4 2-The addition of (2) increases the acidity of the aluminum trioxide.
In some embodiments, the sulfate salt comprises (NH)4)2SO4、Al2(SO4)3And Ti (SO)4)2At least one of (1). That is, the sulfate may be (NH)4)2SO4、Al2(SO4)3And Ti (SO)4)2One of them, two or a mixture of two or more of the above sulfates may be used.
In some embodiments, the sulfate may be added in various ways, for example, the sulfate may be used to modify the alumina catalyst by impregnation or coprecipitation, or may be added during the preparation of alumina.
In some embodiments, the modified alumina is prepared by the process of: the uniform mixture of sulfate and alumina is extruded and molded and then roasted.
More specifically, in some embodiments, an aqueous solution of sulfate and a dispersion of alumina are uniformly mixed to form a paste, the paste is placed at room temperature for 5-8 hours, and then is subjected to rotary evaporation to obtain a solid, extrusion molding, drying and roasting; preferably, the rotary evaporation is performed under vacuum conditions.
It should be noted that the shape of the modified nano alumina catalyst particles is not particularly limited, and for example, in some embodiments, the modified nano alumina catalyst particles may be extruded into a cloverleaf shape, and may be selected from powder, spheres, cylinders, and the like.
Further, in some embodiments, the drying temperature after molding is 110 to 120 ℃, for example, 110 ℃, 111 ℃, 112 ℃, 113 ℃, 114 ℃, 115 ℃, 116 ℃, 117 ℃, 118 ℃, 119 ℃ or 120 ℃. The drying time may be 2 to 5 hours, such as 2 hours, 3 hours, 4 hours, or 5 hours.
Further, in some embodiments, the baking temperature is 400 to 450 ℃, for example, 400 ℃, 410 ℃, 420 ℃, 430 ℃, 440 ℃, or 450 ℃. The baking time is 1.5 to 3 hours, and may be, for example, 1.5 hours, 2 hours, 2.5 hours, or 3 hours.
For the reaction system for preparing isooctyl acrylate, increasing the reaction temperature is beneficial to the reaction, but too high temperature can increase side reaction, further reduce the selectivity of isooctyl acrylate, and too low temperature can reduce the conversion rate, so in some embodiments, the esterification dehydration reaction is performed at the temperature of 70-180 ℃, preferably at the temperature of 80-150 ℃, and more preferably at the temperature of 85-120 ℃.
Further, in order to enable the reaction raw materials to react better in the reaction vessel, in some embodiments, the raw materials may be preheated first, and then the modified alumina catalyst is added to react, and further preferably, the preheating temperature is 70 to 120 ℃, and more preferably, the preheating temperature is 95 to 100 ℃.
In the reaction system according to the embodiment of the present invention, the reaction of producing isooctyl acrylate by dehydration of acrylic acid and 2-ethylhexanol is usually carried out under normal pressure. The reaction is a normal pressure reaction, no solvent is required to be added, and the protection of inert gases such as nitrogen or helium is not required in the reaction.
In some embodiments, for the present reaction system, acrylic acid and 2-ethylhexanol are present in a molar ratio of 1: 1.2 to 1.5 in proportion. Meanwhile, in the reaction system of the esterification dehydration reaction, a polymerization inhibitor is added to the raw materials. The amount of the polymerization inhibitor added is 0.1-0.3% of the weight of the acrylic acid, and in some embodiments, the polymerization inhibitor may be phenothiazine.
In some embodiments, the esterification dehydration reaction is carried out in a fixed bed reactor containing a bed of modified alumina catalyst. Namely, the reaction raw materials can be contacted with the modified catalyst bed layer through the fixed bed reactor so as to meet the requirement of continuous reaction.
In some embodiments, the preparation of isooctyl acrylate generally further comprises neutralizing, dealcoholizing and rectifying the product after the esterification dehydration reaction. Wherein, the neutralization, dealcoholization and rectification processes are all the prior art, and are not described again.
Some embodiments of the present invention provide a method for preparing isooctyl acrylate, comprising: and (2) contacting acrylic acid with 2-ethyl hexanol and a modified alumina catalyst at the temperature of 80-150 ℃, performing esterification dehydration reaction, collecting a crude product, and performing neutralization, dealcoholization and rectification to obtain a finished product.
Referring to fig. 1, some embodiments of the present invention further provide an apparatus for preparing isooctyl acrylate, which comprises a fixed bed reactor 7, wherein the fixed bed reactor 7 is filled with a bed layer of a modified alumina catalyst, the filling amount of the catalyst is determined according to the size of the specific fixed bed reactor 7, and the modified alumina catalyst is obtained by modifying an alumina catalyst with sulfate.
The fixed-bed reactor 7 is also provided with a feed inlet and a product outlet for the introduction of acrylic acid and 2-ethylhexanol. The fixed bed reactor 7 is a vertical tubular reactor, a raw material inlet is arranged above a bed layer of the filled modified alumina catalyst, a product discharge port is also arranged at the part of the fixed bed reactor 7, which is positioned below the bed layer of the modified alumina catalyst, and a steam discharge port is also arranged at the top of the fixed bed reactor 7. Therefore, the reaction raw materials can be introduced into the fixed bed reactor from the upper part, so that the reaction raw materials are contacted with the catalyst bed layer, in the reaction process, the generated isooctyl acrylate product is continuously discharged from the bottom of the fixed bed reactor under the action of gravity, meanwhile, the water generated in the reaction process is continuously changed into water vapor to be discharged from the top of the fixed bed reactor 7, so that the reaction balance can be continuously moved to one side of generating the isooctyl acrylate, and the reaction can be continuously carried out until the acrylic acid is completely reacted, therefore, the conversion rate of the reaction can be up to 98%.
Further, referring to fig. 1, the apparatus for preparing isooctyl acrylate further comprises: the acrylic acid charging container 1, the 2-ethylhexanol charging container 2, the polymerization inhibitor charging container 3 and the raw material mixing container 4 are respectively communicated with the acrylic acid charging container 1, the 2-ethylhexanol charging container 2 and the polymerization inhibitor charging container 3, and the raw material mixing container 4 is communicated with the raw material inlet.
The acrylic acid feeding container 1, the 2-ethylhexanol feeding container 2 and the polymerization inhibitor feeding container 3 are corresponding raw material storage tanks, the positions of the raw material storage tanks are all arranged at high positions, raw materials can be directly conveyed to the raw material mixer 4 through gravity, the raw material mixer 4 is of a sealed kettle type structure, and a stirring device is arranged in the raw material mixer 4, so that various raw materials can be fully mixed.
Further, a preheating tower 6 is provided between the raw material inlet of the fixed bed reactor 7 and the raw material mixing vessel 4. The preheating tower 6 can heat the raw materials to a preheating temperature before the reaction, so as to avoid the influence of the whole reaction efficiency caused by the heating process of the reaction raw materials in the fixed bed reactor 7. A delivery pump 5 is also arranged on the delivery pipeline between the raw material mixer 4 and the preheating tower 6 to provide power for the delivery of the mixed raw materials.
Further, the steam discharge port is also communicated with a condenser 8, and the steam can be condensed by the condenser, and the condensed water can be further utilized.
It should be noted that the heating process of the fixed bed reactor 7 in the above embodiment is realized by circulation of heat transfer oil, and the condensation of the condenser 8 is realized by circulation of cooling water.
The features and properties of the present invention are described in further detail below with reference to examples.
The following examples were all conducted using the apparatus shown in FIG. 1 to prepare isooctyl acrylate.
Example 1
The method for preparing isooctyl acrylate provided by the embodiment specifically comprises the following steps:
weighing Ti (SO)4)250.0g, adding 3000ml distilled water, stirring to dissolve, weighing commercially available powder gamma-Al2O3(A: specific surface area 2900m2Per g)950.0g, the above Ti (SO) was poured in4)2Stirring the solution to form paste. Standing at room temperature for 5 hr, rotary evaporating under vacuum to obtain solid, extruding into clover shape, oven drying at 110 deg.C for 2 hr, and roasting at 450 deg.C for 1.5 hr to obtain Ti (SO)4)2Modified gamma-Al2O3Modified gamma-Al obtained by the method, denoted as catalyst A2O3Containing SO4 2-The content of (B) is 4 wt%.
20g of catalyst A was charged into a tubular reactor having a diameter of 8mm and a length of 400mm, and acrylic acid, 2-ethylhexanol and phenothiazine, a polymerization inhibitor, were added in an amount of 1: 1.5: 0.002, pre-mixing well in advance, inputting the premix into a reactor at a speed of 5ml/min by a metering pump, keeping the outlet temperature of a preheater at 98 ℃, keeping the reactor temperature at 110 ℃, continuously reacting for 100 hours, collecting a crude product, and neutralizing, dealcoholizing and rectifying to obtain the isooctyl acrylate. Product purity 99.5% (GC), moisture: 0.16% (KF) in 90% yield.
Example 2
Weighing (NH)4)2SO4250.0g, adding 2000ml distilled water, stirring to dissolve, weighing commercially available powder gamma-Al2O3(A: specific surface area 2900m2490.0 g/g), the above (NH) is poured in4)2SO4Stirring the solution to form paste. Standing at room temperature for 5 hr, rotary evaporating under vacuum to obtain solid, extruding into clover shape, oven drying at 110 deg.C for 2 hr, and baking at 450 deg.C for 1.5 hr to obtain (NH)4)2SO4Modified gamma-Al2O3Denoted as catalyst B, modified gamma-Al thus obtained2O3Containing SO4 2-The content of (B) is 4 wt%.
20g of catalyst B was added to a tubular reactor having a diameter of 8mm and a length of 400mm, and acrylic acid, 2-ethylhexanol and phenothiazine, a polymerization inhibitor, were added in an amount of 1: 1.5: 0.002, pre-mixing well in advance, inputting the premix into a reactor at a speed of 5ml/min by a metering pump, keeping the outlet temperature of a preheater at 98 ℃, keeping the reactor temperature at 110 ℃, continuously reacting for 100 hours, collecting a crude product, and neutralizing, dealcoholizing and rectifying to obtain the isooctyl acrylate. Product purity 99.2% (GC), moisture: 0.18% (KF) in 90.5% yield.
In summary, the method for preparing isooctyl acrylate provided by the embodiment of the invention adopts the modified alumina catalyst, so that the production capacity is greatly improved, 90-1200 g of isooctyl acrylate can be produced per gram of catalyst per hour, and the selectivity of isooctyl acrylate can reach more than 95%. In addition, the method of the embodiment of the present invention is to distill off the generated water while the reaction is carried out, so that the reaction can be continued at the temperature until the acrylic acid is completely reacted, and thus the conversion rate of the reaction is 98%. Therefore, the method can effectively improve the conversion rate and selectivity of the reaction, and adopts a continuous production process, the process flow is simple, the production process is stable and easy to control, the production is safe and reliable, the energy consumption is low, and the waste water is less.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. A method of making isooctyl acrylate, comprising: carrying out esterification dehydration reaction on acrylic acid and 2-ethylhexanol under the action of a modified alumina catalyst;
wherein, the modified alumina catalyst is obtained by modifying an alumina catalyst with sulfate.
2. The method for preparing isooctyl acrylate of claim 1 wherein the modified alumina catalyst contains 1-4% by mass of sulfate ions.
3. The method of claim 1, wherein the sulfate salt comprises (NH)4)2SO4、Al2(SO4)3And Ti (SO)4)2At least one of (1).
4. The method for preparing isooctyl acrylate according to claim 1 wherein the sulfate is used to modify the alumina catalyst by impregnation or coprecipitation;
preferably, the uniform mixture of the sulfate and the alumina is extruded and then roasted;
preferably, the aqueous solution of the sulfate and the dispersion liquid of the alumina are uniformly mixed into paste, the paste is placed at room temperature for 5 to 8 hours, and then is subjected to rotary evaporation to obtain a solid, extrusion molding, drying and roasting; preferably, the rotary evaporation is performed under vacuum conditions; preferably, extruded into a clover shape; preferably, the drying temperature is 110-120 ℃, and the drying time is 2-5 hours;
preferably, the roasting temperature is 400-450 ℃, and the roasting time is 1.5-3 hours;
preferably, the alumina is γ -Al2O3。
5. The method for preparing isooctyl acrylate according to any one of claims 1-4, wherein the esterification dehydration reaction is carried out at a temperature of 70-180 ℃, preferably 80-150 ℃, more preferably 85-120 ℃;
preferably, the raw materials are preheated, and then the modified alumina catalyst is added for reaction, further preferably, the preheating temperature is 70-120 ℃, and more preferably, the preheating temperature is 95-100 ℃.
6. The method for preparing isooctyl acrylate according to any one of claims 1-4, wherein the ratio of acrylic acid to 2-ethylhexanol is in the molar ratio of 1: 1.2-1.5;
preferably, a polymerization inhibitor is also added to the raw materials for the esterification dehydration reaction; further preferably, the addition amount of the polymerization inhibitor is 0.1-0.3% of the weight of the acrylic acid, and the polymerization inhibitor is phenothiazine.
7. The method for preparing isooctyl acrylate according to any one of claims 1-4, wherein the esterification dehydration reaction is carried out in a fixed bed reactor containing the modified alumina catalyst.
8. The method for preparing isooctyl acrylate according to any one of claims 1-4, further comprising neutralizing, dealcoholizing and rectifying the product after the esterification dehydration reaction.
9. The device for preparing isooctyl acrylate is characterized by comprising a fixed bed reactor, wherein a bed layer of a modified alumina catalyst is filled in the fixed bed reactor, the modified alumina catalyst is obtained by modifying the alumina catalyst with sulfate, and the fixed bed reactor is also provided with a raw material inlet and a product outlet for introducing acrylic acid and 2-ethylhexanol;
preferably, the fixed bed reactor is a tubular reactor vertically arranged, the raw material inlet is arranged above the bed layer of the filled modified alumina catalyst, the product outlet is arranged below the bed layer of the modified alumina catalyst in the fixed bed reactor, and the top of the fixed bed reactor is also provided with a steam outlet.
10. The apparatus of claim 9, further comprising: the device comprises an acrylic acid feeding container, a 2-ethylhexanol feeding container, a polymerization inhibitor feeding container and a raw material mixing container, wherein the acrylic acid feeding container, the 2-ethylhexanol feeding container and the polymerization inhibitor feeding container are respectively communicated with the raw material mixing container, and the raw material mixing container is communicated with a raw material inlet;
preferably, a preheating tower is further arranged between the raw material inlet and the raw material mixing container;
preferably, the water vapor outlet is also communicated with a condenser.
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Citations (5)
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|---|---|---|---|---|
| US4280009A (en) * | 1975-10-30 | 1981-07-21 | Heinz Erpenbach | Continuous production of 2-ethyl-hexyl acrylate free from dioctylether |
| JPH0596171A (en) * | 1991-10-03 | 1993-04-20 | Nikko Kyodo Co Ltd | Production of alumina-base solid acid catalyst |
| CN1613558A (en) * | 2004-10-12 | 2005-05-11 | 南京大学 | Modified alumina catalyst for synthetizing dimethyl ether |
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2020
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4280009A (en) * | 1975-10-30 | 1981-07-21 | Heinz Erpenbach | Continuous production of 2-ethyl-hexyl acrylate free from dioctylether |
| JPH0596171A (en) * | 1991-10-03 | 1993-04-20 | Nikko Kyodo Co Ltd | Production of alumina-base solid acid catalyst |
| CN1613558A (en) * | 2004-10-12 | 2005-05-11 | 南京大学 | Modified alumina catalyst for synthetizing dimethyl ether |
| CN102633611A (en) * | 2012-03-28 | 2012-08-15 | 南开大学 | Method of using modified alumina catalyst to continuously prepare methyl vinyl ketone |
| CN110357780A (en) * | 2019-07-17 | 2019-10-22 | 江苏新东风化工科技有限公司 | A kind of production technology of Isooctyl acrylate monomer |
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