CN105330537A - Preparation method of methoxyethyl acrylate - Google Patents
Preparation method of methoxyethyl acrylate Download PDFInfo
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- CN105330537A CN105330537A CN201510852633.XA CN201510852633A CN105330537A CN 105330537 A CN105330537 A CN 105330537A CN 201510852633 A CN201510852633 A CN 201510852633A CN 105330537 A CN105330537 A CN 105330537A
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- acrylate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/03—Preparation of carboxylic acid esters by reacting an ester group with a hydroxy group
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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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- 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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- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
The invention discloses a preparation method of methoxyethyl acrylate. The preparation method is characterized in that methyl acrylate and methyl cellosolve are taken as raw materials; in the presence of a catalyst and a polymerization inhibitor, a reactive distillation ester exchange process is adopted for reaction; the catalysis in the reaction is realized by using zinc acetylacetonate, and methanol generated by reaction is timely removed by azeotropic distillation, so that a reaction product containing the methoxyethyl acrylate is obtained; the dosage mole ratio of the methyl acrylate to the methyl cellosolve is (1.0-5.0) to 1, the usage of the catalyst is 0.01 to 1.0 percent of total mass of raw materials, and the usage of the polymerization inhibitor is 0.02 to 2.0 percent of total mass of the raw materials. The method has better catalytic effect for preparing the methoxyethyl acrylate; according to the method, the movement of the reaction towards the direction of generating the methoxyethyl acrylate is promoted, reaction time is shortened, the content of polymer is obviously reduced, and the efficiency of a reaction still is improved.
Description
Technical field
The present invention relates to a kind of preparation method of Chemicals, be related specifically to a kind of preparation method of methoxyethyl acrylate.
Background technology
Methoxyethyl acrylate is a kind of important two-component acrylicester adhesive and thermosetting acrylic resin, and it is high temperature resistant/and oil-proofness makes it can be used as the comonomer of polyacrylic elastomer.Can be used as barrier coat and tackiness agent in addition, PVC impact modifying agent, contact lens.There is provided good bounding force, chemical resistance, elasticity, impact, weathering resistance and low-shrinkage.It or UV solidify the splendid reactive diluent of series.The preparation method of prior art methoxyethyl acrylate mainly contains direct esterification and ester-interchange method.
CN102850217A discloses the preparation method of one (methyl) methoxyethyl acrylate, is with (methyl) methyl acrylate and ethylene glycol-methyl ether for raw material, under composite catalyst and stopper effect, generates (methyl) methoxyethyl acrylate.Described catalyzer is that organic tin catalyzer is or/and organic titanium class catalyzer.
TQ225.13+1 describes a kind of with the methoxyethyl acrylate green syt route of the solvent-free participation of heteropolyacid (silicotungstic acid) catalysis.Adopt ethylene glycol monomethyl ether and vinylformic acid direct esterification and obtain, productive rate is 93.2%.
0258-3283(2008) 12-0947-01 describes a kind of synthetic method of methoxyethyl acrylate.Employing tosic acid is catalyzer, and Resorcinol is stopper, and utilize ethylene glycol monomethyl ether and vinylformic acid direct esterification and obtain, water entrainer is toluene, productive rate nearly 70%.
CN101475475 discloses a kind of method being prepared vinylformic acid alkoxyalkyl methacrylate or methacrylic ethyl ester by esterification process operational path, be with acrylic or methacrylic acid and ethylene glycol monoalkyl ether for raw material, with SO
4 2-/ TiO
2solid super-strong acid is catalyzer, thiodiphenylamine or thiodiphenylamine-Resorcinol-copper powder are stopper, toluene is water entrainer, direct esterification acrylic acid synthesizing alkoxyalkyl methacrylate or methacrylic ethyl ester, the method catalyzer and product separation are easily, little to equipment corrosion.
US6008404 discloses the transesterification reaction that a kind of alkyl methacrylate and alcohols carry out, and catalyzer is alkali metal alcoholates, and stopper is bromine salt.
US2002111511 discloses a kind of Exchange Ester Process of methylpropionate class, and used catalyst is a) alkali metal cyanate or thiocyanate-, b) alkaline earth metal oxide, alkali metal hydroxide or halogenide, the mixture of the two.
The catalyzer mentioned in above-mentioned document and patent, kind is more, and different, organic tin catalyzer or/and compound catalyst (based on the organic tin catalyzer) relative price of organic titanium class catalyzer costly, cost is higher; There is the problems such as the loss of active ingredient solution-off and carbon distribution inactivation in heteropolyacid (silicotungstic acid) catalyzer; Solid super-strong acid SO
4 2-/ TiO
2, an acidic catalyst such as toluene sulfonic acide, it generally all has certain acidity, has certain requirement to equipment, apparatus and operational condition etc., and long reaction time, side reaction are many, serious three wastes; Alkali metal alcoholates, alkali metal cyanate or thiocyanate-and alkaline earth metal oxide, alkali metal hydroxide or the mixture etc. both halogenide are mentioned specific to preparing methoxyethyl acrylate.The direct esterification reaction adopted in report, there is complicated operation, easily causes the problems such as environmental pollution in this method more in technique.
Summary of the invention
Object of the present invention is exactly to solve the problem, and provides the preparation method of the methoxyethyl acrylate that a kind of reaction efficiency is high, cost is low.
In order to achieve the above object, present invention employs following technical scheme: a kind of preparation method of methoxyethyl acrylate, is characterized in that: adopt acrylate and methyl cellosolve reaction, react and carry out catalysis by zinc acetylacetonate.
The reaction of acrylate and methyl cellosolve is, getting methyl acrylate and methyl cellosolve is 1.0 ~ 5.0:1 batching in molar ratio, add together in reactor, then the methyl ethyl diketone zinc catalyst of the total mass 0.01% ~ 1.0% being equivalent to methyl acrylate and methyl cellosolve is added, and stopper, open and stir, heat temperature raising, after tower top temperature rises, after tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column ratio, controlling reflux ratio makes tower top temperature be stabilized in 61 ~ 66 DEG C, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature has when obviously rising, stop heating, cooling, temperature controls at 60-80 DEG C, reaction solution is moved on to separating still underpressure distillation, first excessive methyl acrylate is removed, then Removal of catalyst, stopper and heavy component, the methoxyethyl acrylate product that purity is greater than 99.5% can be obtained from tower top.
Reaction solution removes the vacuum degree control of methyl acrylate at 10 ~ 15kPa when moving on to separating still underpressure distillation, tower top temperature controls at 40 ~ 50 DEG C.
Methoxyethyl methacrylate distillation vacuum degree control at 0.01 ~ 2kPa, tower top temperature controls at 66 ~ 100 DEG C.
The consumption mol ratio of described methyl acrylate and methyl cellosolve is 2.0 ~ 3.0:1.
The consumption of described methyl ethyl diketone zinc catalyst is raw material total mass 0.01% ~ 1.0%.
Stopper consumption is equivalent to the total mass 0.02% ~ 2.0% of methyl acrylate and methyl cellosolve.
Described stopper is the one in nitroxyl oxides of free radical inhibitor, is di-tert-butyl nitroxide or 2,2,6,6-tetramethyl--4-hydroxy piperidine-1-oxygen nitroxyl free radical or tetramethyl piperidine nitrogen oxygen free radical tris phosphite
.
The temperature of reaction of acrylate and methyl cellosolve controls at 80 ~ 130 DEG C.
The reaction of acrylate and methyl cellosolve is under agitation carried out, and stir speed (S.S.) is 100-500rpm.
The preparation method of methoxyethyl acrylate of the present invention, owing to have employed above technical scheme, makes it compared with prior art, has following advantage and disadvantage:
Owing to employing efficient catalyzer, shorten the reaction times, reduce polymer content, improve quality product and yield.Catalyst levels is few, and cost is low.Reactive distillation process technology, by excessive methyl acrylate and the formation of methanol azeotrope, removes by-product carbinol in time, facilitate reaction and want that the direction generating methoxyethyl acrylate is moved, shorten the reaction times, significantly reduce polymer content, improve the efficiency of reactor.
Accompanying drawing explanation
Fig. 1 is the process flow diagram of the preparation method of methoxyethyl acrylate of the present invention.
Shown in process flow sheet, 1 is reactor, and 2 is one-level rectifying tower, and 3 is azeotrope receiving tank, and 4 is separating still, and 5 is two-stage rectification tower, and 6 is Light ends receiving tank, and 7 is intermediate component receiving tank, and 8 is product receiving tank.
Embodiment
The preparation method of methoxyethyl acrylate of the present invention is: getting methyl acrylate and methyl cellosolve is 2.0 ~ 3.0:1 batching in molar ratio, adds together in reactor.Then the catalyzer of the total mass 0.01% ~ 1.0% being equivalent to methyl acrylate and methyl cellosolve is added, and be equivalent to the stopper of total mass 0.02% ~ 2.0% of methyl acrylate and methyl cellosolve, open and stir, heat temperature raising, after tower top temperature rises, after tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column ratio, controlling reflux ratio makes tower top temperature be stabilized in 61 ~ 66 DEG C, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature has when obviously rising, stop heating, cooling (controlling at 60-80 DEG C).Reaction solution is moved on to separating still underpressure distillation, first (vacuum degree control is at 10 ~ 15kPa to remove excessive methyl acrylate, tower top temperature controls at 40 ~ 50 DEG C), then Removal of catalyst, stopper and heavy component, can from tower top obtain purity be greater than 99.5% methoxyethyl acrylate product (methoxyethyl acrylate product distillation vacuum degree control at 0.01 ~ 2kPa, tower top temperature controls at 66 ~ 100 DEG C).
The present invention is further illustrated below by embodiment.Embodiment 1
5 liters of reactors, on reactor, rectifying tower is φ 50*2.5mm, tower height 1000mm
Add 2263g methyl acrylate and 1000g methyl cellosolve in a kettle., add 65.3g dibutyl tin sulfide as catalyzer, add 6.53g tetramethyl piperidine nitrogen oxygen free radical tris phosphite as stopper.
Open and stir, heat temperature raising, when reactor temperature rises to 90 ~ 100 DEG C, tower top starts discharging, total reflux, when tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column than system, reflux ratio is 6:1 ~ 6:2, tower top temperature is made to be stabilized in 61 ~ 66 DEG C by regulating reflux ratio, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature have when obviously rising, and stops heating, cooling, sampling analysis.
Reaction solution composition (passing through gas chromatography determination):
Methyl alcohol 0.12%
Methyl cellosolve 8.63%
Methyl acrylate 27.24%
Methoxyethyl acrylate 59.22%
Heavy constituent 2.83%
Reaction solution is moved on to separating still, start decompression separation, under 10 ~ 15kPa condition, remove excessive methyl methacrylate, then Removal of catalyst, stopper and heavy component under 1 ~ 2000Pa condition, obtains at product receiving tank the methoxyethyl acrylate product 1631g that purity is greater than 99.8%.
Embodiment 2
5 liters of reactors, on reactor, rectifying tower is φ 50*2.5mm, tower height 1000mm
Add 2037g methyl acrylate and 1200g methyl cellosolve in a kettle., the mixture adding 64.7g Dibutyltin oxide and tetrabutyl titanate, as catalyzer (the two quality proportioning 3:1), adds 6.47g tetramethyl piperidine nitrogen oxygen free radical tris phosphite as stopper.
Open and stir, heat temperature raising, when reactor temperature rises to 90 ~ 100 DEG C, tower top starts discharging, total reflux, when tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column than system, reflux ratio is 6:1 ~ 6:2, tower top temperature is made to be stabilized in 61 ~ 66 DEG C by regulating reflux ratio, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature have when obviously rising, and stops heating, cooling, sampling analysis.
Reaction solution composition (passing through gas chromatography determination):
Methyl alcohol 0.05%
Methyl cellosolve 7.27%
Methyl acrylate 27.11%
Methoxyethyl acrylate 61.55%
Heavy constituent 2.92%
Reaction solution is moved on to separating still, start decompression separation, under 10 ~ 15kPa condition, remove excessive methyl methacrylate, then Removal of catalyst, stopper and heavy component under 1 ~ 2000Pa condition, obtains at product receiving tank the methoxyethyl acrylate product 1783g that purity is greater than 99.8%.
Embodiment 3
5 liters of reactors, on reactor, rectifying tower is φ 50*2.5mm, tower height 1000mm
Add 2263g methyl acrylate and 1000g methyl cellosolve in a kettle., add 16.32g zinc acetylacetonate, add 3.26g tetramethyl piperidine nitrogen oxygen free radical tris phosphite as stopper.
Open and stir, heat temperature raising, when reactor temperature rises to 90 ~ 100 DEG C, tower top starts discharging, total reflux, when tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column than system, reflux ratio is 6:1 ~ 6:2, tower top temperature is made to be stabilized in 61 ~ 66 DEG C by regulating reflux ratio, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature have when obviously rising, and stops heating, cooling, sampling analysis.
Reaction solution composition (passing through gas chromatography determination):
Methyl alcohol 0.4%
Methyl cellosolve 6.82%
Methyl acrylate 31.33%
Methoxyethyl acrylate 60.38%
Heavy constituent 0.81%
Reaction solution is moved on to separating still, start decompression separation, under 10 ~ 15kPa condition, remove excessive methyl methacrylate, then Removal of catalyst, stopper and heavy component under 1 ~ 2000Pa condition, obtains at product receiving tank the methoxyethyl acrylate product 1793g that purity is greater than 99.8%.
Embodiment 4
5 liters of reactors, on reactor, rectifying tower is φ 50*2.5mm, tower height 1000mm
Add 2037g methyl acrylate and 1200g methyl cellosolve in a kettle., add 22.66g zinc acetylacetonate, add 3.24g tetramethyl piperidine nitrogen oxygen free radical tris phosphite as stopper.
Open and stir, heat temperature raising, when reactor temperature rises to 90 ~ 100 DEG C, tower top starts discharging, total reflux, when tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column than system, reflux ratio is 6:1 ~ 6:2, tower top temperature is made to be stabilized in 61 ~ 66 DEG C by regulating reflux ratio, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature have when obviously rising, and stops heating, cooling, sampling analysis.
Reaction solution composition (passing through gas chromatography determination):
Methyl alcohol 0.4%
Methyl cellosolve 7.31%
Methyl acrylate 27.50%
Methoxyethyl acrylate 64.01%
Heavy constituent 0.35%
Reaction solution is moved on to separating still, start decompression separation, under 10 ~ 15kPa condition, remove excessive methyl methacrylate, then Removal of catalyst, stopper and heavy component under 1 ~ 2000Pa condition, obtains at product receiving tank the methoxyethyl acrylate product 1750g that purity is greater than 99.8%.
Embodiment 5
1000 liters of reactors, on reactor, rectifying tower is φ 400*5mm, tower height 6800mm
Add 680kg methyl acrylate and 300kg methyl cellosolve in a kettle., add 5.88kg zinc acetylacetonate, add 0.98kg tetramethyl piperidine nitrogen oxygen free radical tris phosphite as stopper.
Open and stir, heat temperature raising, when reactor temperature rises to 90 ~ 100 DEG C, tower top starts discharging, total reflux, when tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column than system, reflux ratio is 6:1 ~ 6:2, tower top temperature is made to be stabilized in 61 ~ 66 DEG C by regulating reflux ratio, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature have when obviously rising, and stops heating, cooling, sampling analysis.
Reaction solution composition (passing through gas chromatography determination):
Methyl alcohol 0.06%
Methyl cellosolve 9.27%
Methyl acrylate 23.46%
Methoxyethyl acrylate 65.88%
Heavy constituent 0.61%
Reaction solution is moved on to separating still, start decompression separation, under 10 ~ 15kPa condition, remove excessive methyl methacrylate, then Removal of catalyst, stopper and heavy component under 1 ~ 2000Pa condition, obtains at product receiving tank the methoxyethyl acrylate product 559kg that purity is greater than 99.8%.
Claims (10)
1. a preparation method for methoxyethyl acrylate, is characterized in that: adopt acrylate and methyl cellosolve reaction, react and carry out catalysis by zinc acetylacetonate.
2. the preparation method of a kind of methoxyethyl acrylate according to claim 1, is characterized in that: the reaction of acrylate and methyl cellosolve is, getting methyl acrylate and methyl cellosolve is 1.0 ~ 5.0:1 batching in molar ratio, add together in reactor, then the methyl ethyl diketone zinc catalyst of the total mass 0.01% ~ 1.0% being equivalent to methyl acrylate and methyl cellosolve is added, and stopper, open and stir, heat temperature raising, after tower top temperature rises, after tower top temperature is stabilized in 61 ~ 63 DEG C, open trim the top of column ratio, controlling reflux ratio makes tower top temperature be stabilized in 61 ~ 66 DEG C, treat between still temperature rise to 115 ~ 125 DEG C, and tower top temperature has when obviously rising, stop heating, cooling, temperature controls at 60-80 DEG C, reaction solution is moved on to separating still underpressure distillation, first excessive methyl acrylate is removed, then Removal of catalyst, stopper and heavy component, the methoxyethyl acrylate product that purity is greater than 99.5% can be obtained from tower top.
3. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: remove the vacuum degree control of methyl acrylate when reaction solution moves on to separating still underpressure distillation at 10 ~ 15kPa, tower top temperature controls at 40 ~ 50 DEG C.
4. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: methoxyethyl methacrylate distillation vacuum degree control at 0.01 ~ 2kPa, tower top temperature controls at 66 ~ 100 DEG C.
5. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: the consumption mol ratio of described methyl acrylate and methyl cellosolve is 2.0 ~ 3.0:1.
6. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: the consumption of described methyl ethyl diketone zinc catalyst is raw material total mass 0.01% ~ 1.0%.
7. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: stopper consumption is equivalent to the total mass 0.02% ~ 2.0% of methyl acrylate and methyl cellosolve.
8. the preparation method of a kind of methoxyethyl acrylate according to claim 2 or 7, it is characterized in that: described stopper is the one in nitroxyl oxides of free radical inhibitor, for di-tert-butyl nitroxide or 2,2,6,6-tetramethyl--4-hydroxy piperidine-1-oxygen nitroxyl free radical or tetramethyl piperidine nitrogen oxygen free radical tris phosphite
.
9. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: the temperature of reaction of acrylate and methyl cellosolve controls at 80 ~ 130 DEG C.
10. the preparation method of a kind of methoxyethyl acrylate according to claim 2, is characterized in that: the reaction of acrylate and methyl cellosolve is under agitation carried out, and stir speed (S.S.) is 100-500rpm.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110713438A (en) * | 2019-05-29 | 2020-01-21 | 抚顺东联安信化学有限公司 | Production process of ethylene glycol di (meth) acrylate |
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| JPH03181449A (en) * | 1989-12-08 | 1991-08-07 | Mitsui Toatsu Chem Inc | Production of acrylic acid or methacrylic acid alkylaminoalkyl ester |
| JP2005132790A (en) * | 2003-10-31 | 2005-05-26 | Mitsubishi Gas Chem Co Inc | Method for producing 2-methyl-2-hydroxy-1-propyl (meth)acrylate |
| CN101952239A (en) * | 2008-02-22 | 2011-01-19 | 出光兴产株式会社 | Alicyclic structure-containing compound, (meth) acrylic acid esters and process for producing the same |
| CN102351693A (en) * | 2011-08-23 | 2012-02-15 | 里光 | Preparation method for methoxyethyl methacrylate |
| CN103140287A (en) * | 2010-06-15 | 2013-06-05 | 埃科辛斯私人有限公司 | Transesterification process using mixed salt acetylacetonates catalysts |
-
2015
- 2015-11-30 CN CN201510852633.XA patent/CN105330537A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH03181449A (en) * | 1989-12-08 | 1991-08-07 | Mitsui Toatsu Chem Inc | Production of acrylic acid or methacrylic acid alkylaminoalkyl ester |
| JP2005132790A (en) * | 2003-10-31 | 2005-05-26 | Mitsubishi Gas Chem Co Inc | Method for producing 2-methyl-2-hydroxy-1-propyl (meth)acrylate |
| CN101952239A (en) * | 2008-02-22 | 2011-01-19 | 出光兴产株式会社 | Alicyclic structure-containing compound, (meth) acrylic acid esters and process for producing the same |
| CN103140287A (en) * | 2010-06-15 | 2013-06-05 | 埃科辛斯私人有限公司 | Transesterification process using mixed salt acetylacetonates catalysts |
| CN102351693A (en) * | 2011-08-23 | 2012-02-15 | 里光 | Preparation method for methoxyethyl methacrylate |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110713438A (en) * | 2019-05-29 | 2020-01-21 | 抚顺东联安信化学有限公司 | Production process of ethylene glycol di (meth) acrylate |
| CN110713438B (en) * | 2019-05-29 | 2022-04-15 | 抚顺东联安信化学有限公司 | Production process of ethylene glycol di (meth) acrylate |
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