CN110357780A - A kind of production technology of Isooctyl acrylate monomer - Google Patents
A kind of production technology of Isooctyl acrylate monomer Download PDFInfo
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- CN110357780A CN110357780A CN201910644714.9A CN201910644714A CN110357780A CN 110357780 A CN110357780 A CN 110357780A CN 201910644714 A CN201910644714 A CN 201910644714A CN 110357780 A CN110357780 A CN 110357780A
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- acrylate monomer
- isooctyl acrylate
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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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- 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
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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
- C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
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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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- Crystallography & Structural Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of production technologies of Isooctyl acrylate monomer, including preparing raw material, esterification, depth esterification, thick steaming, dealcoholysis and raffinate treatment process, the production technology of Isooctyl acrylate monomer is optimized in the present invention, by the composite catalyst of high catalytic performance being added and the most of esterification of completion under room temperature environment, the generation of side reaction can effectively be controlled, deep layer esterification is carried out by heating again, improves the conversion ratio of esterification；Raw material propylene acid is added in the mode that esterification and deep layer esterification overall process are all made of dropwise addition, can guarantee that entirely reaction occurs under alcohol excess environment, reduces side reaction, guarantees the stability of esterification；The reaction residues such as water, alcohol, acid are separated in time with Isooctyl acrylate monomer by the way of thick steaming, high-temperature steam dealcoholysis, avoids being carried out dehydrating using benzene class water absorbing agent, reduces the complicated procedures of forming of post-processing；Prepare that Isooctyl acrylate monomer conversion rate of esterification is high, side reaction is few, finished product is with high purity using the present invention.
Description
Technical field:
The present invention relates to the production technical field of Isooctyl acrylate monomer more particularly to a kind of production works of Isooctyl acrylate monomer
Skill.
Background technique:
Isooctyl acrylate monomer is the monomer of a kind of important synthetic intermediate and synthesising macromolecule copolymer, is used extensively
In rubber, medicine, leather, papermaking, adhesive and coating industry.Direct esterification is to prepare the important method of Isooctyl acrylate monomer,
Direct esterification is in process of production along with a variety of side reactions, for the generation for reducing side reaction, presently mainly in reactant
In system be added dehydrating agent slough in time reaction generate water, then dehydrating agent is mostly benzene class organic solvent, be unfavorable for environmental protection and after
It handles comparatively laborious.
The information disclosed in the background technology section is intended only to increase the understanding to general background of the invention, without answering
When being considered as recognizing or imply that the information constitutes the prior art already known to those of ordinary skill in the art in any form.
Summary of the invention:
The purpose of the present invention is to provide a kind of production technologies of Isooctyl acrylate monomer, thus overcome it is above-mentioned in the prior art
Defect.
To achieve the above object, the present invention provides a kind of production technologies of Isooctyl acrylate monomer, it is characterised in that: including
Following steps:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein acrylic acid and isooctanol
Ratio is 1:1.5, and catalyst accounts for the 2-10% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for acrylic acid and isooctanol total amount
0.01-0.1%；
2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, reacted 6-8 hours under room temperature environment,
Acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；
3) depth is esterified, and the reaction solution of step 2) is heated to 80-90 DEG C of reaction 30-60 minutes in a kettle, reacted
Remaining acrylic acid is added in reaction kettle in a manner of dropwise addition in journey；
4) thick to steam, thick steaming is kept the temperature after reaction solution is warming up to 140-150 DEG C, the thick gained mixed vapour that steams recycles after condensing
It obtains slightly steaming Isooctyl acrylate monomer and reaction residue；
5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, it is different that high-temperature water vapor takes thick steaming acrylic acid out of
Alcohol in monooctyl ester obtains Isooctyl acrylate monomer finished product；
6) raffinate is handled, and lye is added into raffinate and carries out neutralization reaction, removes the acid in raffinate.
The catalyst of the step 1) is catalyst compounded using aluminium phosphotungstic acid and SO42-/ZrO2 solid acid, wherein phosphotungstic acid
The weight ratio of aluminium and SO42-/ZrO2 solid acid is 1.5:1.
The polymerization inhibitor of the step 1) uses benzothiophene and 2,4- di-tert-butylphenol compound polymerization inhibitor, wherein benzothiophene
Weight ratio with 2,4- di-tert-butylphenol is 1:1.
Pressure control is in -30-30KPa when the step 2) esterification.
Pressure control is in -20-20KPa when step 3) the depth esterification.
Pressure control is in -100--20KPa, thick steaming 20-30 minutes when the step 4) is slightly steamed.
The temperature of high-temperature water vapor is 180-200 DEG C when the step 5) dealcoholysis, and pressure control is in -500-- when dealcoholysis
200KPa。
Compared with prior art, one aspect of the present invention has the following beneficial effects:
The present invention optimizes the production technology of Isooctyl acrylate monomer, by the composite catalyst that high catalytic performance is added
And most esterification is completed under room temperature environment, the generation of side reaction can be effectively controlled, then carry out deeply by heating
Layer esterification, improves the conversion ratio of esterification；Raw material third is added in the mode that esterification and deep layer esterification overall process are all made of dropwise addition
Olefin(e) acid can guarantee that entirely reaction occurs under alcohol excess environment, reduces side reaction, guarantees the stability of esterification；Using
It is thick steam, the mode of high-temperature steam dealcoholysis in time separates the reaction residues such as water, alcohol, acid with Isooctyl acrylate monomer, avoid adopting
It is carried out dehydrating with benzene class water absorbing agent, reduces the complicated procedures of forming of post-processing；Isooctyl acrylate monomer esterification is prepared using the present invention
High conversion rate, side reaction is few, finished product is with high purity.
Specific embodiment:
Specific embodiments of the present invention will be described in detail below, it is to be understood that protection scope of the present invention is not
It is restricted by specific implementation.
Unless otherwise explicitly stated, otherwise in entire disclosure and claims, term " includes " or its change
Changing such as "comprising" or " including " etc. will be understood to comprise stated element or component, and not exclude other members
Part or other component parts.
Embodiment 1:
A kind of production technology of Isooctyl acrylate monomer, it is characterised in that: the following steps are included:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein acrylic acid and isooctanol
Ratio is 1:1.5, and catalyst accounts for the 2% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for acrylic acid and isooctanol total amount
0.01%；2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, react 8 hours under room temperature environment, instead
Acrylic acid is added in reaction kettle in a manner of dropwise addition during answering；3) depth is esterified, and the reaction solution of step 2) is in reaction kettle
In be heated to 80 DEG C react 60 minutes, remaining acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；4)
Thick steaming keeps the temperature thick steaming after reaction solution is warming up to 140 DEG C, thick steaming gained mixed vapour recycles after condensing to be obtained slightly steaming acrylic acid
Different monooctyl ester and reaction residue；5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, and high-temperature water vapor takes thick steaming out of
Alcohol in Isooctyl acrylate monomer obtains Isooctyl acrylate monomer finished product；6) raffinate is handled, and lye is added into raffinate and neutralize instead
It answers, removes the acid in raffinate.
The catalyst of the step 1) is catalyst compounded using aluminium phosphotungstic acid and SO42-/ZrO2 solid acid, wherein phosphotungstic acid
The weight ratio of aluminium and SO42-/ZrO2 solid acid is 1.5:1；Polymerization inhibitor uses benzothiophene and 2, the compounding resistance of 4- di-tert-butylphenol
Poly- agent, wherein benzothiophene and 2, the weight ratio of 4- di-tert-butylphenol are 1:1；Pressure controls when the step 2) esterification
In -30KPa；Pressure control is in -20KPa when step 3) the depth esterification；The step 4) slightly steam when pressure control-
100KPa is thick to steam 20 minutes；The temperature of high-temperature water vapor is 180 DEG C when the step 5) dealcoholysis, when dealcoholysis pressure control-
500KPa。
Esterification yield is further detected by the way of acid esters titration, the esterification yield of Isooctyl acrylate monomer reaction can achieve
97%, the purity of Isooctyl acrylate monomer is up to 97.5%.
Embodiment 2:
A kind of production technology of Isooctyl acrylate monomer, it is characterised in that: the following steps are included:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein acrylic acid and isooctanol
Ratio is 1:1.5, and catalyst accounts for the 5% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for acrylic acid and isooctanol total amount
0.05%；2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, react 7 hours under room temperature environment, instead
Acrylic acid is added in reaction kettle in a manner of dropwise addition during answering；3) depth is esterified, and the reaction solution of step 2) is in reaction kettle
In be heated to 85 DEG C react 45 minutes, remaining acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；4)
Thick steaming keeps the temperature thick steaming after reaction solution is warming up to 145 DEG C, thick steaming gained mixed vapour recycles after condensing to be obtained slightly steaming acrylic acid
Different monooctyl ester and reaction residue；5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, and high-temperature water vapor takes thick steaming out of
Alcohol in Isooctyl acrylate monomer obtains Isooctyl acrylate monomer finished product；6) raffinate is handled, and lye is added into raffinate and neutralize instead
It answers, removes the acid in raffinate.
The catalyst of the step 1) is catalyst compounded using aluminium phosphotungstic acid and SO42-/ZrO2 solid acid, wherein phosphotungstic acid
The weight ratio of aluminium and SO42-/ZrO2 solid acid is 1.5:1, and polymerization inhibitor uses benzothiophene and 2, the compounding resistance of 4- di-tert-butylphenol
Poly- agent, wherein benzothiophene and 2, the weight ratio of 4- di-tert-butylphenol are 1:1；Pressure controls when the step 2) esterification
In -10KPa；Pressure control -5KPa when step 3) the depth esterification；The step 4) slightly steam when pressure control-
50KPa is thick to steam 25 minutes；The temperature of high-temperature water vapor is 190 DEG C when the step 5) dealcoholysis, when dealcoholysis pressure control-
300KPa。
Esterification yield is further detected by the way of acid esters titration, the esterification yield of Isooctyl acrylate monomer reaction can achieve
97.5%, the purity of Isooctyl acrylate monomer is up to 98%.
Embodiment 3:
A kind of production technology of Isooctyl acrylate monomer, it is characterised in that: the following steps are included:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein acrylic acid and isooctanol
Ratio is 1:1.5, and catalyst accounts for the 8% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for acrylic acid and isooctanol total amount
0.08%；2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, reacted 6.5 hours under room temperature environment,
Acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；3) depth is esterified, and the reaction solution of step 2) is reacting
It is heated to 88 DEG C in kettle to react 35 minutes, remaining acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；
4) thick steaming keeps the temperature thick steaming after reaction solution is warming up to 148 DEG C, thick steaming gained mixed vapour recycles after condensing to be obtained slightly steaming propylene
The different monooctyl ester of acid and reaction residue；5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, and high-temperature water vapor is taken out of slightly
The alcohol in Isooctyl acrylate monomer is steamed, Isooctyl acrylate monomer finished product is obtained；6) raffinate is handled, and lye is added into raffinate and is neutralized
Reaction removes the acid in raffinate.
The catalyst of the step 1) is catalyst compounded using aluminium phosphotungstic acid and SO42-/ZrO2 solid acid, wherein phosphotungstic acid
The weight ratio of aluminium and SO42-/ZrO2 solid acid is 1.5:1, and polymerization inhibitor uses benzothiophene and 2, the compounding resistance of 4- di-tert-butylphenol
Poly- agent, wherein benzothiophene and 2, the weight ratio of 4- di-tert-butylphenol are 1:1；Pressure control exists when the step 2) esterification
10KPa；Pressure control is in 10KPa when step 3) the depth esterification；The step 4) slightly steam when pressure control-
30KPa is thick to steam 30 minutes；The temperature of high-temperature water vapor is 195 DEG C when the step 5) dealcoholysis, when dealcoholysis pressure control-
350KPa。
Esterification yield is further detected by the way of acid esters titration, the esterification yield of Isooctyl acrylate monomer reaction can achieve
96.5%, the purity of Isooctyl acrylate monomer is up to 96%.
Embodiment 4:
A kind of production technology of Isooctyl acrylate monomer, it is characterised in that: the following steps are included:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein acrylic acid and isooctanol
Ratio is 1:1.5, and catalyst accounts for the 10% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for acrylic acid and isooctanol total amount
0.1%；2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, reacted 6 hours under room temperature environment, react
Acrylic acid is added in reaction kettle in a manner of dropwise addition in the process；3) depth is esterified, and the reaction solution of step 2) is in a kettle
It is heated to 90 DEG C to react 30 minutes, remaining acrylic acid is added in reaction kettle in a manner of dropwise addition in reaction process；4) thick
Steam, kept the temperature after reaction solution is warming up to 150 DEG C it is thick steam, it is thick steam gained mixed vapour recycled after condensing obtain slightly steaming acrylic acid it is different
Monooctyl ester and reaction residue；5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, high-temperature water vapor takes thick steaming third out of
Alcohol in the different monooctyl ester of olefin(e) acid, obtains Isooctyl acrylate monomer finished product；6) raffinate is handled, and lye is added into raffinate and neutralize instead
It answers, removes the acid in raffinate.
The catalyst of the step 1) is catalyst compounded using aluminium phosphotungstic acid and SO42-/ZrO2 solid acid, wherein phosphotungstic acid
The weight ratio of aluminium and SO42-/ZrO2 solid acid is 1.5:1, and polymerization inhibitor uses benzothiophene and 2, the compounding resistance of 4- di-tert-butylphenol
Poly- agent, wherein benzothiophene and 2, the weight ratio of 4- di-tert-butylphenol are 1:1；Pressure controls when the step 2) esterification
In -30KPa；Pressure control is in -20KPa when step 3) the depth esterification；The step 4) slightly steam when pressure control-
100KPa is thick to steam 20 minutes；The temperature of high-temperature water vapor is 200 DEG C when the step 5) dealcoholysis, when dealcoholysis pressure control-
500KPa。
Esterification yield is further detected by the way of acid esters titration, the esterification yield of Isooctyl acrylate monomer reaction can achieve
98%, the purity of Isooctyl acrylate monomer is up to 98.5%.
To sum up, the production technology of Isooctyl acrylate monomer is optimized in the present invention, by the way that answering for high catalytic performance is added
It closes catalyst and completes most esterification under room temperature environment, can effectively control the generation of side reaction, then by adding
Heat carries out deep layer esterification, improves the conversion ratio of esterification；The mode that esterification and deep layer esterification overall process are all made of dropwise addition adds
Enter raw material propylene acid, can guarantee that entirely reaction occurs under alcohol excess environment, reduces side reaction, guarantees the stabilization of esterification
Property；The reaction residues such as water, alcohol, acid are separated with Isooctyl acrylate monomer in time by the way of thick steaming, high-temperature steam dealcoholysis,
It avoids being carried out dehydrating using benzene class water absorbing agent, reduces the complicated procedures of forming of post-processing；It is different pungent that acrylic acid is prepared using the present invention
Ester conversion rate of esterification is high, side reaction is few, finished product is with high purity.
The aforementioned description to specific exemplary embodiment of the invention is in order to illustrate and illustration purpose.These descriptions
It is not wishing to limit the invention to disclosed precise forms, and it will be apparent that according to the above instruction, can much be changed
And variation.The purpose of selecting and describing the exemplary embodiment is that explaining specific principle of the invention and its actually answering
With so that those skilled in the art can be realized and utilize a variety of different exemplary implementation schemes of the invention and
Various chooses and changes.The scope of the present invention is intended to be limited by claims and its equivalents.
Claims (7)
1. a kind of production technology of Isooctyl acrylate monomer, it is characterised in that: the following steps are included:
1) prepare raw material, prepare acrylic acid, isooctanol, catalyst and polymerization inhibitor raw material, wherein the ratio of acrylic acid and isooctanol
For 1:1.5, catalyst accounts for the 2-10% of acrylic acid and isooctanol total amount, and polymerization inhibitor accounts for the 0.01- of acrylic acid and isooctanol total amount
0.1%；
2) it is esterified, isooctanol, catalyst and polymerization inhibitor is added in reaction kettle, reacted 6-8 hours under room temperature environment, react
Acrylic acid is added in reaction kettle in a manner of dropwise addition in the process；
3) depth is esterified, and the reaction solution of step 2) is heated to 80-90 DEG C of reaction 30-60 minutes in a kettle, in reaction process
Remaining acrylic acid is added in reaction kettle in a manner of dropwise addition；
4) thick steaming keeps the temperature thick steaming after reaction solution is warming up to 140-150 DEG C, thick steaming gained mixed vapour recycles after condensing to be obtained
It is thick to steam Isooctyl acrylate monomer and reaction residue；
5) dealcoholysis is passed through high-temperature water vapor toward thick steam in Isooctyl acrylate monomer, high-temperature water vapor takes thick steaming Isooctyl acrylate monomer out of
In alcohol, obtain Isooctyl acrylate monomer finished product；
6) raffinate is handled, and lye is added into raffinate and carries out neutralization reaction, removes the acid in raffinate.
2. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the step 1) is urged
Agent uses aluminium phosphotungstic acid and SO4 2-/ZrO2Solid acid is catalyst compounded, wherein aluminium phosphotungstic acid and SO4 2-/ZrO2The weight of solid acid
Amount is than being 1.5:1.
3. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the resistance of the step 1)
Poly- agent uses benzothiophene and 2,4- di-tert-butylphenol compound polymerization inhibitor, wherein benzothiophene and 2, the weight of 4- di-tert-butylphenol
Than for 1:1.
4. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the step 2) esterification
Pressure control is in -30-30KPa when reaction.
5. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the step 3) depth
Pressure control is in -20-20KPa when esterification.
6. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the step 4) is slightly steamed
When pressure control in -100--20KPa, it is thick to steam 20-30 minutes.
7. a kind of production technology of Isooctyl acrylate monomer according to claim 1, it is characterised in that: the step 5) dealcoholysis
When high-temperature water vapor temperature be 180-200 DEG C, pressure control is in -500--200KPa when dealcoholysis.
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| CN201910644714.9A CN110357780A (en) | 2019-07-17 | 2019-07-17 | A kind of production technology of Isooctyl acrylate monomer |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111807960A (en) * | 2020-08-01 | 2020-10-23 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
| CN111807956A (en) * | 2020-06-26 | 2020-10-23 | 江苏国胶新材料有限公司 | Production process of isooctyl acrylate of ultralow-concentration oligomer |
| CN112592271A (en) * | 2020-12-22 | 2021-04-02 | 河北兴柏农业科技有限公司 | Method and device for preparing isooctyl acrylate |
| CN115353816A (en) * | 2022-08-10 | 2022-11-18 | 福建友谊胶粘带集团有限公司 | Manufacturing process of insulating adhesive tape |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111807956A (en) * | 2020-06-26 | 2020-10-23 | 江苏国胶新材料有限公司 | Production process of isooctyl acrylate of ultralow-concentration oligomer |
| CN111807960A (en) * | 2020-08-01 | 2020-10-23 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
| CN111807960B (en) * | 2020-08-01 | 2022-04-22 | 浙江亦龙新材料有限公司 | Preparation process of isooctyl acrylate |
| CN112592271A (en) * | 2020-12-22 | 2021-04-02 | 河北兴柏农业科技有限公司 | Method and device for preparing isooctyl acrylate |
| CN115353816A (en) * | 2022-08-10 | 2022-11-18 | 福建友谊胶粘带集团有限公司 | Manufacturing process of insulating adhesive tape |
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Application publication date: 20191022 |