CN115947656A - Production method and system of hydroxybutyl acrylate - Google Patents
Production method and system of hydroxybutyl acrylate Download PDFInfo
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- CN115947656A CN115947656A CN202211715315.5A CN202211715315A CN115947656A CN 115947656 A CN115947656 A CN 115947656A CN 202211715315 A CN202211715315 A CN 202211715315A CN 115947656 A CN115947656 A CN 115947656A
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- hydroxybutyl acrylate
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- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 21
- 230000018044 dehydration Effects 0.000 claims abstract description 51
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 51
- 238000005886 esterification reaction Methods 0.000 claims abstract description 35
- 239000000463 material Substances 0.000 claims abstract description 29
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000006243 chemical reaction Methods 0.000 claims abstract description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 14
- 239000003112 inhibitor Substances 0.000 claims abstract description 10
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 10
- 238000006386 neutralization reaction Methods 0.000 claims abstract description 9
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 52
- 208000005156 Dehydration Diseases 0.000 claims description 47
- 239000012528 membrane Substances 0.000 claims description 34
- 230000003068 static effect Effects 0.000 claims description 27
- 238000009834 vaporization Methods 0.000 claims description 21
- 230000008016 vaporization Effects 0.000 claims description 21
- 238000001704 evaporation Methods 0.000 claims description 15
- 230000008020 evaporation Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 6
- 238000005086 pumping Methods 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 230000032050 esterification Effects 0.000 claims description 4
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 claims description 3
- 239000012670 alkaline solution Substances 0.000 claims description 3
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 claims description 3
- 229950000688 phenothiazine Drugs 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000002904 solvent Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
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Classifications
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a production method and a system of hydroxybutyl acrylate, belonging to the technical field of hydroxybutyl acrylate, and the production method comprises the following steps: mixing acrylic acid, a polymerization inhibitor, 1, 4-butanediol and a catalyst, and then sending the mixture into a first reactor for primary esterification reaction; the material after the primary esterification reaction is dehydrated and then sent into a second reactor for secondary esterification reaction; the material after the second esterification reaction is dehydrated for the second time and then is sent into a third reactor for the third esterification reaction; and (4) feeding the reaction liquid after the three times of esterification reaction into a neutralizer for neutralization treatment. The production method can realize reaction continuity, vacuum dehydration continuity and neutralization continuity without using a water-carrying solvent, reduces the operation difficulty, improves the working efficiency, and has small equipment volume, small material storage capacity and high safety.
Description
Technical Field
The invention relates to the technical field of hydroxybutyl acrylate, in particular to a production method and a system of hydroxybutyl acrylate.
Background
Hydroxybutyl acrylate is obtained by direct esterification of acrylic acid with 1, 4-butanediol, and since this reaction is a reversible reaction, water generated during the reaction prevents the reaction from proceeding in the forward direction.
In order to avoid the reaction from being blocked to proceed in the positive direction due to the generated water, the method adopted by the prior art and the disadvantages thereof are as follows:
1. water generated by the esterification reaction is taken away by utilizing water-carrying agents such as toluene, cyclohexane and the like; but it requires distillation recovery, increasing disposal costs;
2. pumping water by vacuum; however, the vacuum pumping is intermittent pumping, and the efficiency is low.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a production method and a system of hydroxybutyl acrylate.
The invention discloses a production method of hydroxybutyl acrylate, which comprises the following steps:
adding acrylic acid and a polymerization inhibitor into a first buffer tank;
adding 1, 4-butanediol and a catalyst into a second buffer tank;
pumping the acrylic acid in the first buffer tank and the 1, 4-butanediol in the second buffer tank into a first static mixer according to a preset ratio;
feeding the mixed materials into a first reactor for primary esterification reaction;
feeding the material after the primary esterification reaction into a shell pass of a vaporization dehydration membrane of a first dehydrator, vacuumizing water molecules which pass through the vaporization dehydration membrane and enter an inner tube pass of the vaporization dehydration membrane to a condenser outside the membrane, and condensing and collecting the water molecules;
feeding the material subjected to primary dehydration into a second reactor for secondary esterification;
the material after the secondary esterification reaction enters the shell pass of a vaporization dehydration membrane of a second dehydrator, water molecules which pass through the vaporization dehydration membrane and enter the inner tube pass of the vaporization dehydration membrane are pumped to a condenser outside the membrane in vacuum, and are collected after condensation;
feeding the materials subjected to secondary dehydration into a third reactor for carrying out tertiary esterification reaction;
and (4) feeding the reaction liquid after the three times of esterification reaction into a neutralizer for neutralization treatment.
As a further improvement of the invention, the addition amount of the polymerization inhibitor is 5-10% of the weight of the acrylic acid, and the polymerization inhibitor comprises but is not limited to one or more of hydroquinone, phenothiazine, TT copper salt and p-hydroxyanisole.
As a further refinement of the present invention, the catalyst includes, but is not limited to, one or more of p-toluenesulfonic acid, methanesulfonic acid, and sulfuric acid.
As a further improvement of the invention, the mass ratio of the 1, 4-butanediol to the acrylic acid is 2.
As a further improvement of the invention, the mixed materials are sent into a first reactor tube side, circulating hot water is introduced into a first reactor shell side, the water temperature of the circulating hot water is 60-90 ℃, and the temperature of the circulating hot water is 70-80 ℃ for ensuring the reaction temperature of primary esterification reaction.
As a further improvement of the method, the material after primary dehydration is sent into the tube pass of a second reactor, circulating hot water is introduced into the shell pass of the second reactor, the water temperature of the circulating hot water is 60-90 ℃, and the temperature of the circulating hot water is used for ensuring that the reaction temperature of the secondary esterification is 80-90 ℃.
As a further improvement of the method, the material after secondary dehydration is sent to the tube pass of a third reactor, circulating hot water is introduced into the shell pass of the third reactor, the water temperature of the circulating hot water is 60-90 ℃, and the temperature of the circulating hot water is used for ensuring that the reaction temperature of the third esterification reaction is 80-90 ℃.
As a further improvement of the invention, the reaction liquid enters a cooler after being neutralized in the neutralizer, and enters a reaction liquid storage tank after being cooled.
The invention also discloses a production system of the hydroxybutyl acrylate, which is used for realizing the production method of the hydroxybutyl acrylate and comprises the following steps: the system comprises a first buffer tank, a second buffer tank, a first static mixer, a first reactor, a first dehydrator, a second reactor, a second dehydrator, a third reactor, a neutralizer, a condenser, a cooler and a reaction liquid storage tank, wherein the first buffer tank is connected with the second buffer tank;
the first buffer tank and the second buffer tank are both connected with the first static mixer;
the first static mixer is connected with a tube side inlet of the first reactor, and a hot water circulation channel is arranged in a shell side of the first reactor;
the tube pass outlet of the first reactor is connected with the evaporation dehydration membrane shell pass inlet of the first dehydrator, the evaporation dehydration membrane shell pass outlet is connected with the tube pass inlet of the second reactor, the evaporation dehydration membrane inner tube pass of the first dehydrator is connected with the condenser, and the condenser is connected with the water collection tank;
the tube pass outlet of the second reactor is connected with the shell pass inlet of the evaporation dehydration membrane of the second dehydrator, the shell pass outlet of the evaporation dehydration membrane is connected with the tube pass inlet of the third reactor, and the inner tube pass of the evaporation dehydration membrane of the second dehydrator is connected with the condenser;
and the tube pass outlet of the third reactor is connected with the neutralizer, an alkaline solution feeding port is arranged on the neutralizer, and the outlet of the neutralizer is connected with the reaction liquid storage tank through the cooler.
As a further improvement of the invention, the method also comprises the following steps: a second static mixer and a third static mixer;
the second static mixer is arranged between the first dehydrator and the second reactor;
the third static mixer is disposed between the second dehydrator and the third reactor.
Compared with the prior art, the invention has the beneficial effects that:
the production method can realize reaction continuity, vacuum dehydration continuity and neutralization continuity without using a water-carrying solvent, reduces the operation difficulty, improves the working efficiency, and has small equipment volume, small material storage capacity and high safety.
Drawings
FIG. 1 is a schematic diagram showing the structure of a hydroxybutyl acrylate manufacturing system according to an embodiment of the present invention.
In the figure:
1. a first buffer tank; 2. a second buffer tank; 3. a first static mixer; 4. a first reactor; 5. a first dehydrator; 6. a second reactor; 7. a second dehydrator; 8. a third reactor; 9. a neutralizer; 10. a condenser; 11. a cooler; 12. a reaction liquid storage tank; 13. a second static mixer; 14. a third static mixer; 15. a water collection tank.
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 with reference to the drawings in the embodiments of the present invention, and it is obvious that the described embodiments are some, but not all, embodiments of the present invention. All other embodiments, which can be obtained by a person skilled in the art without any inventive step based on the embodiments of the present invention, are within the scope of the present invention.
The invention is described in further detail below with reference to the attached drawing figures:
the invention provides a production method of hydroxybutyl acrylate, which adopts continuous reaction, continuous vacuum dehydration and continuous neutralization; the method specifically comprises the following steps:
step 1, adding acrylic acid and a polymerization inhibitor into a first buffer tank; wherein, the adding amount of the polymerization inhibitor is 5-10% of the weight of the acrylic acid, and the polymerization inhibitor comprises one or more of hydroquinone, phenothiazine, TT copper salt and p-hydroxyanisole;
step 2, adding 1, 4-butanediol and a catalyst into a second buffer tank; wherein, the catalyst includes but is not limited to one or more of p-toluenesulfonic acid, methanesulfonic acid and sulfuric acid;
step 3, pumping the acrylic acid in the first buffer tank and the 1, 4-butanediol in the second buffer tank into a first static mixer according to a preset ratio; wherein, the mass ratio of the 1, 4-butanediol to the acrylic acid is 2;
step 4, feeding the mixed materials into a first reactor for primary esterification reaction; wherein, the mixed materials are sent to a first reactor tube side, circulating hot water is introduced into a first reactor shell side, the water temperature of the circulating hot water is 60-90 ℃, and the temperature of the circulating hot water is used for ensuring that the reaction temperature of the primary esterification reaction is 70-80 ℃;
step 5, feeding the material after the primary esterification reaction into a shell pass of a vaporization dehydration membrane of the first dehydrator, vacuumizing water molecules which pass through the vaporization dehydration membrane and enter a tube pass in the vaporization dehydration membrane to a condenser outside the membrane, and condensing and collecting the water molecules;
step 6, feeding the materials subjected to primary dehydration into a second reactor for secondary esterification reaction; wherein, the material after primary dehydration is sent to the tube pass of a second reactor, circulating hot water is introduced into the shell pass of the second reactor, the water temperature of the circulating hot water is 60-90 ℃, and the temperature of the circulating hot water is used for ensuring the reaction temperature of the secondary esterification reaction to be 80-90 ℃;
step 7, feeding the material after the secondary esterification reaction into a shell pass of a vaporization dehydration film of a second dehydrator, vacuumizing water molecules which pass through the vaporization dehydration film and enter a tube pass in the vaporization dehydration film to a condenser outside the film, and condensing and collecting the water molecules;
step 8, feeding the materials subjected to secondary dehydration into a third reactor for carrying out tertiary esterification reaction; wherein, the material after the secondary dehydration is sent to the tube pass of a third reactor, the shell pass of the third reactor is filled with circulating hot water, the temperature of the circulating hot water is 60-90 ℃, and the circulating hot water is used for ensuring the reaction temperature of the tertiary esterification reaction to be 80-90 DEG C
Step 9, feeding the reaction liquid after the three times of esterification reaction into a neutralizer for neutralization treatment; and (4) after neutralization treatment, feeding the reaction mixture into a cooler, and after cooling, feeding the reaction mixture into a reaction liquid storage tank.
As shown in fig. 1, the present invention provides a hydroxybutyl acrylate production system, for implementing the above hydroxybutyl acrylate production method, comprising: a first buffer tank 1, a second buffer tank 2, a first static mixer 3, a first reactor 4, a first dehydrator 5, a second reactor 6, a second dehydrator 7, a third reactor 8, a neutralizer 9, a condenser 10, a cooler 11, a reaction liquid storage tank 12, a second static mixer 13, a third static mixer 14 and a water collection tank 15; wherein,
the first buffer tank 1 and the second buffer tank 2 are both connected with a first static mixer 3, the first static mixer 3 is connected with a tube side inlet of a first reactor 4, and a hot water circulation channel is arranged in a shell side of the first reactor 4; the tube pass outlet of the first reactor 4 is connected with the shell pass inlet of the vaporization dehydration membrane of the first dehydrator 5, the shell pass outlet of the vaporization dehydration membrane is connected with the tube pass inlet of the second reactor 6, and a second static mixer 13 is arranged between the first dehydrator 5 and the second reactor 6, the tube pass of the vaporization dehydration membrane of the first dehydrator 5 is connected with a condenser 10, and the condenser 10 is connected with a water collecting tank 15; the tube pass outlet of the second reactor 6 is connected with the evaporation dehydration membrane shell pass inlet of the second dehydrator 7, the evaporation dehydration membrane shell pass outlet is connected with the tube pass inlet of the third reactor 8, a third static mixer 14 is arranged between the second dehydrator 7 and the third reactor 8, the evaporation dehydration membrane inner tube pass of the second dehydrator 7 is connected with a condenser 10, and the condenser 10 is connected with a water collecting tank 15; the tube side outlet of the third reactor 8 is connected with a neutralizer 9, an alkaline solution feeding port is arranged on the neutralizer 9, and the outlet of the neutralizer 9 is connected with a reaction liquid storage tank 12 through a cooler 11.
Further, the power of the liquid flow is derived from a pump group such as a lift pump.
The invention has the advantages that:
the production method can realize reaction continuity, vacuum dehydration continuity and neutralization continuity without using a water-carrying solvent, reduces the operation difficulty, improves the working efficiency, and has small equipment volume, small material storage capacity and high safety. The above is only a preferred embodiment of the present invention, and is not intended to limit the present invention, and various modifications and changes will occur to 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 for producing hydroxybutyl acrylate, comprising:
adding acrylic acid and a polymerization inhibitor into a first buffer tank;
adding 1, 4-butanediol and a catalyst into a second buffer tank;
pumping the acrylic acid in the first buffer tank and the 1, 4-butanediol in the second buffer tank into a first static mixer according to a preset ratio;
feeding the mixed materials into a first reactor for primary esterification reaction;
feeding the material after the primary esterification reaction into a shell pass of a vaporization dehydration film of a first dehydrator, vacuumizing water molecules which pass through the vaporization dehydration film and enter a tube pass in the vaporization dehydration film to a condenser outside the film, condensing and collecting the water molecules;
feeding the material subjected to primary dehydration into a second reactor for secondary esterification;
the material after the secondary esterification reaction enters the shell pass of a vaporization dehydration membrane of a second dehydrator, water molecules which pass through the vaporization dehydration membrane and enter the inner tube pass of the vaporization dehydration membrane are pumped to a condenser outside the membrane in vacuum, and are collected after condensation;
feeding the material subjected to secondary dehydration into a third reactor for carrying out tertiary esterification reaction;
and (4) feeding the reaction liquid after the three times of esterification reaction into a neutralizer for neutralization treatment.
2. The method of claim 1, wherein the polymerization inhibitor is added in an amount of 5-10% by weight of the acrylic acid, and the polymerization inhibitor includes but is not limited to one or more of hydroquinone, phenothiazine, copper TT salts, and p-hydroxyanisole.
3. The method of claim 1, wherein the catalyst includes, but is not limited to, one or more of p-toluenesulfonic acid, methanesulfonic acid, and sulfuric acid.
4. The process for the production of hydroxybutyl acrylate according to claim 1, wherein the mass ratio of 1, 4-butanediol to acrylic acid is from 2.
5. The process for producing hydroxybutyl acrylate according to claim 1, wherein the mixed materials are fed into the first reactor tube side, and the first reactor shell side is filled with circulating hot water, wherein the temperature of the circulating hot water is 60-90 ℃ which is used to ensure that the reaction temperature of the primary esterification reaction is 70-80 ℃.
6. The process for producing hydroxybutyl acrylate according to claim 1, wherein the first dehydrated material is fed into the second reactor tube side, and the second reactor shell side is filled with circulating hot water, wherein the temperature of the circulating hot water is 60-90 ℃ which is used to ensure that the reaction temperature of the second esterification reaction is 80-90 ℃.
7. The process for producing hydroxybutyl acrylate according to claim 1, wherein the material after the second dehydration is fed into the tube side of the third reactor, and the shell side of the third reactor is filled with circulating hot water, wherein the temperature of the circulating hot water is 60-90 ℃ which is used to ensure that the reaction temperature of the third esterification reaction is 80-90 ℃.
8. The process for producing hydroxybutyl acrylate according to claim 1, wherein the reaction mixture is neutralized in the neutralizer, and then the neutralized reaction mixture is introduced into a cooler, and then the cooled reaction mixture is introduced into a reaction mixture storage tank.
9. A hydroxybutyl acrylate production system for implementing the hydroxybutyl acrylate production method of any one of claims 1-8, comprising: the system comprises a first buffer tank, a second buffer tank, a first static mixer, a first reactor, a first dehydrator, a second reactor, a second dehydrator, a third reactor, a neutralizer, a condenser, a cooler and a reaction liquid storage tank, wherein the first buffer tank is connected with the second buffer tank;
the first buffer tank and the second buffer tank are both connected with the first static mixer;
the first static mixer is connected with a tube side inlet of the first reactor, and a hot water circulation channel is arranged in a shell side of the first reactor;
the tube pass outlet of the first reactor is connected with the evaporation dehydration membrane shell pass inlet of the first dehydrator, the evaporation dehydration membrane shell pass outlet is connected with the tube pass inlet of the second reactor, the evaporation dehydration membrane inner tube pass of the first dehydrator is connected with the condenser, and the condenser is connected with the water collection tank;
the tube pass outlet of the second reactor is connected with the evaporation dehydration membrane shell pass inlet of the second dehydrator, the evaporation dehydration membrane shell pass outlet is connected with the tube pass inlet of the third reactor, and the evaporation dehydration membrane inner tube pass of the second dehydrator is connected with the condenser;
and the tube pass outlet of the third reactor is connected with the neutralizer, an alkaline solution feeding port is arranged on the neutralizer, and the outlet of the neutralizer is connected with the reaction liquid storage tank through the cooler.
10. The hydroxybutyl acrylate production system of claim 9, further comprising: a second static mixer and a third static mixer;
the second static mixer is arranged between the first dehydrator and the second reactor;
the third static mixer is disposed between the second dehydrator and the third reactor.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211715315.5A CN115947656A (en) | 2022-12-28 | 2022-12-28 | Production method and system of hydroxybutyl acrylate |
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| CN202211715315.5A CN115947656A (en) | 2022-12-28 | 2022-12-28 | Production method and system of hydroxybutyl acrylate |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114920628A (en) * | 2022-03-30 | 2022-08-19 | 江西浩普海诚新材料有限公司 | Continuous method for preparing dialkoxy methane compound by reactor series dehydration membrane |
Non-Patent Citations (1)
| Title |
|---|
| 王伟文等: "4-丙烯酸羟丁酯的合成与应用研究", 合成材料老化与应用, vol. 47, no. 3, pages 111 - 112 * |
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Application publication date: 20230411 |