CN118026987A - Method for producing acetone glycidyl methacrylate through transesterification - Google Patents
Method for producing acetone glycidyl methacrylate through transesterification Download PDFInfo
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- CN118026987A CN118026987A CN202410133198.4A CN202410133198A CN118026987A CN 118026987 A CN118026987 A CN 118026987A CN 202410133198 A CN202410133198 A CN 202410133198A CN 118026987 A CN118026987 A CN 118026987A
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- methyl methacrylate
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- acetone glycidyl
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 16
- 238000005809 transesterification reaction Methods 0.000 title claims abstract description 12
- FEOBTMLKFHZRHZ-UHFFFAOYSA-N oxiran-2-ylmethyl 2-methylprop-2-enoate;propan-2-one Chemical compound CC(C)=O.CC(=C)C(=O)OCC1CO1 FEOBTMLKFHZRHZ-UHFFFAOYSA-N 0.000 title claims description 45
- 238000010992 reflux Methods 0.000 claims abstract description 44
- 238000010438 heat treatment Methods 0.000 claims abstract description 40
- -1 acetonide ester Chemical class 0.000 claims abstract description 34
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 238000003756 stirring Methods 0.000 claims abstract description 29
- 239000003112 inhibitor Substances 0.000 claims abstract description 23
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 23
- QAZYYQMPRQKMAC-FDGPNNRMSA-L calcium;(z)-4-oxopent-2-en-2-olate Chemical compound [Ca+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O QAZYYQMPRQKMAC-FDGPNNRMSA-L 0.000 claims abstract description 9
- NHXVNEDMKGDNPR-UHFFFAOYSA-N zinc;pentane-2,4-dione Chemical compound [Zn+2].CC(=O)[CH-]C(C)=O.CC(=O)[CH-]C(C)=O NHXVNEDMKGDNPR-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000005886 esterification reaction Methods 0.000 claims description 113
- 230000032050 esterification Effects 0.000 claims description 90
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 72
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 45
- 238000001816 cooling Methods 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 26
- 238000004817 gas chromatography Methods 0.000 claims description 24
- 238000004458 analytical method Methods 0.000 claims description 22
- 239000002994 raw material Substances 0.000 claims description 20
- BRCNMMGLEUILLG-UHFFFAOYSA-N 4,5,6-trihydroxyhexan-2-one Chemical compound CC(=O)CC(O)C(O)CO BRCNMMGLEUILLG-UHFFFAOYSA-N 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 34
- 239000002253 acid Substances 0.000 abstract description 19
- CLBRCZAHAHECKY-UHFFFAOYSA-N [Co].[Pt] Chemical compound [Co].[Pt] CLBRCZAHAHECKY-UHFFFAOYSA-N 0.000 abstract description 15
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 abstract description 2
- 229910001385 heavy metal Inorganic materials 0.000 abstract description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- YAXWOADCWUUUNX-UHFFFAOYSA-N 1,2,2,3-tetramethylpiperidine Chemical compound CC1CCCN(C)C1(C)C YAXWOADCWUUUNX-UHFFFAOYSA-N 0.000 abstract 1
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-Tetramethylpiperidine Substances CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 abstract 1
- 238000005485 electric heating Methods 0.000 description 21
- IFJOCHBDHXGFAA-UHFFFAOYSA-N CC([CH2-])=O.OCC(O)CO Chemical compound CC([CH2-])=O.OCC(O)CO IFJOCHBDHXGFAA-UHFFFAOYSA-N 0.000 description 17
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 description 5
- LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical group CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- NBVHDOZEOGAKLK-UHFFFAOYSA-N [N]=O.CC1C(N(CCC1)C)(C)C Chemical compound [N]=O.CC1C(N(CCC1)C)(C)C NBVHDOZEOGAKLK-UHFFFAOYSA-N 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- CQBPOPVKDNHISM-UHFFFAOYSA-N propane-1,2,3-triol;propan-2-one Chemical compound CC(C)=O.OCC(O)CO CQBPOPVKDNHISM-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- QYTDEUPAUMOIOP-UHFFFAOYSA-N TEMPO Chemical group CC1(C)CCCC(C)(C)N1[O] QYTDEUPAUMOIOP-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 239000012948 isocyanate Chemical group 0.000 description 2
- 150000002513 isocyanates Chemical group 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- RNVYQYLELCKWAN-UHFFFAOYSA-N solketal Chemical compound CC1(C)OCC(CO)O1 RNVYQYLELCKWAN-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- SIJBDWPVNAYVGY-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane Chemical compound CC1(C)OCCO1 SIJBDWPVNAYVGY-UHFFFAOYSA-N 0.000 description 1
- ABAMIXORLKXDAB-UHFFFAOYSA-N 2,2-dimethyl-1,3-dioxolane;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CC1(C)OCCO1 ABAMIXORLKXDAB-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Landscapes
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for preparing the methyl methacrylate-condensed acetonide ester by transesterification includes such steps as preparing methyl methacrylate-condensed acetonide ester, polymerization inhibitor tetramethyl piperidine nitroxide-free phosphite triester, adding calcium acetylacetonate or zinc acetylacetonate as catalyst to esterifying reactor, stirring, heating for esterifying reaction, reacting at 103-107 deg.C for 3-6 hr, stopping heating, controlling reflux ratio of reflux unit at top of esterifying reactor to 121-131.5 deg.C, rectifying at 92-96 deg.C, and vacuum rectifying. The advantages are that: the reaction is continuous, the operation is simple and convenient, the organotin catalyst does not contain heavy metal tin, the product yield finally obtained by vacuum rectification is as high as 94.5% -96%, the purity is over 97%, the acid value is 0.001mg/g KOH, and the platinum cobalt chromaticity is 5-20.
Description
Technical Field
The invention relates to a method for producing acetone glycidyl methacrylate by transesterification.
Background
The acetone glycidyl methacrylate has high reactivity between unsaturated double bond and epoxy group difunctional group, the unsaturated double bond can be polymerized, the epoxy group can be ring-opened to form hydroxyl and isocyanate group-NCO to carry out crosslinking reaction, the acetone glycidyl methacrylate has the characteristics of excellent weather resistance, chemical resistance and water resistance, is an excellent active monomer, and is widely applied to the fields of photoresist, printing ink, paint and adhesive. Along with the development of industrial technology, the content requirement of the acetone glycidyl methacrylate is improved, and meanwhile, the acetone glycidyl methacrylate can be used as a reactive diluent to be crosslinked with isocyanate groups-NCO and polymerized and cured, so that the acetone glycidyl methacrylate is required to contain no volatile organic matters-organotin, and has great application value in reducing the emission of volatile organic matters.
At present, the acetone glycidyl methacrylate is mainly obtained by an alcohol acid method or an ester exchange method, the adopted catalyst is an organotin catalyst, such as a method for producing the acetone glycidyl methacrylate by ester exchange disclosed in CN 113831317A, a methyl cyclohexyl dioxolane methacrylate monomer and application disclosed in CN106588864A, a dimethyl dioxolane methacrylate monomer and application disclosed in CN106588860A, the catalyst is dissolved in the methyl methacrylate and the acetone glycidyl methacrylate, and the product contains organotin in the distillation separation process, so that the requirements of the application field cannot be met, or acid wastewater can be generated, and the environmental protection problem is caused. In addition, the acid value, chromaticity, metal content and the like of the product obtained in the prior art cannot meet the requirements, so that the application of the product is limited and the industrial requirements cannot be met.
CN 110272408A discloses a preparation method of a photocuring agent dimethyl dioxolane alcohol methacrylate, which uses methacrylic acid and acetone glycerol with a molar ratio of 0.9:1-1.5:1 as raw materials, adds a solvent, uses 4-dimethylaminopyridine and 1-hydroxybenzotriazole as catalysts, uses TEMPO tetramethylpiperidine nitrogen oxide, hydroquinone, p-hydroxyanisole and phenothiazine as polymerization inhibitors, and adds a dehydrating agent to react at the same time to obtain a product. The preparation method needs to use a solvent and a dehydrating agent, and is complicated in operation after washing, the produced wastewater causes pollution to the environment, the highest product yield is only 77%, and the product yield is low.
Disclosure of Invention
The invention aims to solve the technical problem of providing a method for producing the acetone glycidyl methacrylate by transesterification, which has the advantages of high production efficiency, high speed, less pollution, excellent product performance, high yield and good acid value, chromaticity and metal content of the product.
The technical scheme of the invention is as follows:
A method for producing acetone glycidyl methacrylate by transesterification comprises the following specific steps:
Adding raw materials of methyl methacrylate, acetone glycidyl, a polymerization inhibitor of tetramethylpiperidine nitroxide free radical phosphite triester, and a catalyst of calcium acetylacetonate or zinc acetylacetonate into an esterification reactor which is provided with stirring and is connected with a rectifying tower, a tower top condenser and a reflux ratio controller, wherein the molar ratio of the methyl methacrylate to the acetone glycidyl is (2.6-3.1): 1, the addition amount of the polymerization inhibitor accounts for 0.303-0.454% of the mass of the acetone glycidyl, and the addition amount of the catalyst accounts for 2.5-3.5% of the mass of the acetone glycidyl; and (3) starting stirring to electrify and heat the esterification reactor, reacting at 103-107 ℃ in the esterification reactor for 3-6 h, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, enabling the temperature in the esterification reactor to be 121-131.5 ℃, enabling the temperature at the top of a rectifying tower to be 92-96 ℃, cooling the esterification reactor to 43-54 ℃ through circulating condensed water after the esterification is finished, carrying out reduced pressure rectification, recovering unreacted methyl methacrylate and acetone glycidyl methacrylate in the raw materials, improving the vacuum degree, and continuing the reduced pressure rectification to obtain the acetone glycidyl methacrylate.
Further, when the excessive raw materials of methyl methacrylate and acetone-glycerol are recovered by reduced pressure rectification, the vacuum degree is controlled to be 10KPa-13KPa, and the temperature of the top of the rectifying tower is 40-80 ℃.
Further, when the acetone glycidyl methacrylate is collected by vacuum rectification, the vacuum degree is controlled to be 1kPa-3kPa, and the temperature of the top of the rectifying tower is 120-123 ℃.
Further, the obtained acetone-glycidyl methacrylate product was 97% pure by gas chromatography.
Further, the mass content of the acetonide glycerol is more than or equal to 96.4 percent.
Further, a mixture of methyl methacrylate and methanol, which are azeotropes, is separated from the top of the rectifying column during the esterification process.
The invention has the beneficial effects that:
The method uses an organic calcium or organic zinc neutral catalyst, an efficient polymerization inhibitor tetramethyl piperidine nitroxide free radical phosphite triester, does not use an organic tin catalyst, does not contain heavy metal tin, has small catalyst dosage, combines the efficient polymerization inhibitor, and has the advantages of stable whole reaction and rectification process, continuous reaction, simple and convenient operation, the final product yield obtained by decompression rectification is up to 94.5% -96%, the purity is above 97%, the acid value is 0.001mg/g KOH, and the platinum cobalt chromaticity is 5-20; the azeotrope is a mixture of methyl methacrylate and methanol, the temperature is reduced to below 54 ℃, excessive methyl ester is distilled off under reduced pressure for reuse, the vacuum degree is improved, the temperature is increased, the product is distilled off further, and after the process is finished, the residue is cooled and discharged to carry out the next batch of batch feeding production, so that the method has the characteristics of high production efficiency, high speed, less pollution and excellent product performance.
Drawings
FIG. 1 is a gas chromatogram of raw material acetonide glycerol in an embodiment of the invention;
FIG. 2 is a gas chromatogram of acetonide-glycerol-methacrylate of the present invention (corresponding to example 1);
FIG. 3 is a gas chromatogram of acetonide-glycerol-methacrylate of the present invention (corresponding to example 3);
FIG. 4 is a gas chromatogram of acetonide-glycerol-methacrylate of the present invention (corresponding to comparative example 1);
FIG. 5 is a gas chromatogram of acetonide-glycerol-methacrylate of the present invention (corresponding to comparative example 3).
Detailed Description
Example 1
The first step: esterification reaction
310.4 G of methyl methacrylate, 132.15 g of acetonide glycerol, 0.45 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 4.23 g of calcium acetylacetonate catalyst are added into a 1L esterification reactor provided with a cooling coil, an automatic temperature control electric heating oil bath provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 103 ℃ to start reaction, stopping heating after 4 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to 121 ℃ and the temperature at the top of a rectifying tower to 94 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 43 ℃, starting a vacuum system to control the vacuum degree to 10kPa, and recovering methyl methacrylate and acetonide at the top temperature of a rectifying tower of 40-70 ℃;
And a third step of: collecting the acetone glycidyl methacrylate by vacuum rectification
And continuously heating the esterified liquid after recovering the methyl methacrylate and the acetonide, controlling the vacuum degree to be 1kPa, and obtaining 189.6 g (200.23 g of theory) of the acetonide methacrylate by fraction at the temperature of the top of a rectifying tower at 120-121 ℃, wherein the yield is 94.69%, the purity is 97.1% through gas chromatography analysis, the retention time of the gas chromatogram of the acetonide methacrylate is 9.988 minutes as shown in figure 2, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 20, and the moisture is 0.069%.
Example 2
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 260.32 g of methyl methacrylate, 132.15 g of glycerol acetonide, 0.6 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 4.62 g of calcium acetylacetonate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 107 ℃ for reaction, stopping heating after the reaction is performed for 6 hours, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of a rectifying tower in the esterification process by controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, wherein the temperature in the esterification reactor is 131.5 ℃, and the temperature at the top of the rectifying tower is 92 ℃, thus finishing the esterification reaction;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 13kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-80 ℃.
And a third step of: collecting the acetone glycidyl methacrylate by vacuum rectification
And continuously heating the esterified liquid after methyl methacrylate and acetone glycidyl methacrylate are recovered, controlling the vacuum degree to be 3kPa, and obtaining 190 g (200.23 g of theory) of the acetone glycidyl methacrylate by fraction at the temperature of 122-123 ℃ at the top of a rectifying tower, wherein the yield is 94.9%, the purity is 97.12% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 10, and the moisture is 0.04%.
Example 3
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 300.36 g of methyl methacrylate, 132.15 g of glycerol acetonide, 0.4 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 3.31 g of calcium acetylacetonate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1; ;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106 ℃ to start reaction, stopping heating after 3 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 125.3 ℃, controlling the temperature at the top of a rectifying tower to be 96 ℃, finishing the esterification reaction, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 50 ℃, starting a vacuum system to control the vacuum degree to 12kPa, and recovering methyl methacrylate and acetonide at the top temperature of a rectifying tower of 45-76 ℃;
And a third step of: collecting acetone glycidyl methacrylate by vacuum rectification
And continuously heating the esterified liquid after methyl methacrylate and acetone glycidyl methacrylate are recovered, controlling the vacuum degree to be 2kPa, and obtaining 190.3 g (200.23 g of theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121-122 ℃, wherein the yield is 95%, and the retention time of the acetone glycidyl methacrylate gas chromatogram with the purity of 97.2% is 10.251 minutes as shown in figure 3, wherein the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 10, and the moisture is 0.05%.
Example 4
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 336 g of methyl methacrylate, 158.58 g of acetonylglycerol 158.58 g, 0.64 g of polymerization inhibitor tetramethyl piperidine nitroxide free radical phosphite triester and 4.75 g of calcium acetylacetonate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 105 ℃ to start reaction, stopping heating after 5 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 128.6 ℃, controlling the temperature at the top of a rectifying tower to be 94 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 48 ℃, starting a vacuum system to control the vacuum degree to 11kPa, and recovering methyl methacrylate and acetonide at the top temperature of a rectifying tower of 46-78 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after methyl methacrylate and acetone glycidyl methacrylate are recovered, controlling the vacuum degree to be 2.5kPa, and obtaining 229 g (240.28 g of theory) of the acetone glycidyl methacrylate by fraction at the temperature of the top of a rectifying tower at 122-122.5 ℃, wherein the yield is 95.3%, and the purity is 97.1% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 15, and the moisture is 0.06%.
Example 5
The first step: esterification reaction
309 G of methyl methacrylate, 132 g of acetonide glycerol, 0.56 g of polymerization inhibitor tetramethyl piperidine nitroxide free radical phosphite triester and 3.96 g of zinc acetylacetonate catalyst are added into a 1L esterification reactor provided with a cooling coil and provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106 ℃ for reaction, stopping heating after 3 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to 125 ℃ and the temperature at the top of a rectifying tower to 94 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 52 ℃, starting a vacuum system to control the vacuum degree to 11.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower to 50-74 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after methyl methacrylate and acetone glycidyl methacrylate are recovered, controlling the vacuum degree to be 2.6kPa, and obtaining 189 g (200 g of theory) of the acetone glycidyl methacrylate by fraction at the temperature of 122-122.8 ℃ at the top of a rectifying tower, wherein the yield is 94.5%, the purity is 97% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 18, and the moisture is 0.06%.
Example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 363 g of methyl methacrylate, 160 g of acetonylglycerol, 0.61 g of polymerization inhibitor tetramethyl piperidine nitroxide free radical phosphite triester and 4.64 g of zinc acetylacetonate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106.6 ℃ to start reaction, stopping heating after 5 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 131 ℃, controlling the temperature at the top of a rectifying tower to be 93 ℃, finishing the esterification reaction, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after recovering methyl methacrylate and acetone glycidyl, controlling the vacuum degree to be 1.6kPa, and obtaining 229.8 g (242.43 g in theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121-122 ℃, wherein the yield is 94.8%, the purity is 97.01% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 15, and the moisture is 0.055%.
Example 7
The first step: esterification reaction
310 G of recovered methyl methacrylate, 132 g of acetonide glycerol, 0.56 g of polymerization inhibitor tetramethyl piperidine nitroxide free radical phosphite triester and 4.62 g of calcium acetylacetonate catalyst are added into a 1L esterification reactor provided with a cooling coil and provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 107 ℃ to start reaction, stopping heating after the reaction is performed for 6 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 129.6 ℃, controlling the temperature at the top of a rectifying tower to be 96 ℃, finishing the esterification reaction, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 11.8kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 52-75 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And (3) continuously heating the esterified liquid after recovering the methyl methacrylate and the acetone glycidyl ester, controlling the vacuum degree to be 1.3kPa, and obtaining 192 g (200 g of theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121.8-122.5 ℃, wherein the yield is 96%, the purity is 97% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 5, and the moisture is 0.075%.
Comparative example 1 the catalyst was replaced with dioctyltin oxide, otherwise identical to example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil, a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle are added into a 1L esterification reactor of the esterification reactor at one time, 363 g of methyl methacrylate, 160 g of acetone glycerol with the content of 96.42 percent, 0.61 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 4.64 g of dioctyltin oxide catalyst;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring materials in a reaction kettle uniformly, heating an esterification reactor of the esterification kettle by an oil bath to raise the temperature of the esterification reactor to 106.6 ℃ by using an oil bath to start reaction, reacting for 5 hours, keeping the reaction for 5 hours without complete reaction, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to (8-12): 2, controlling the temperature of the esterification reactor to 131 ℃, finishing the esterification reaction at the temperature of 93 ℃ at the top of a rectifying tower, finishing the esterification reaction, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification:
cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after recovering the methyl methacrylate and the acetone glycidyl, controlling the vacuum degree to be 1.6kPa, and obtaining 189.9 g (242.43 g in theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121-122 ℃, wherein the yield is 78.3%, and the retention time of the acetone glycidyl methacrylate gas chromatogram with the purity of 95.07% is 10.192 minutes, the acid value is 0.003mg/g KOH, the platinum cobalt chromaticity is 35 and the moisture is 0.08% as shown in figure 4.
Comparative example 2 the catalyst was replaced with dibutyltin dilaurate catalyst, otherwise identical to example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 363 g of methyl methacrylate, 160 g of acetonylglycerol, 0.61 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 4.64 g of dibutyltin dilaurate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106.6 ℃ to start reaction, reacting for 5 hours, keeping on reacting for 3 hours, finishing the esterification reaction, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 131 ℃, controlling the temperature at the top of a rectifying tower to be 93 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification:
cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
And a third step of: and (3) continuously heating the esterified liquid of the recovered methyl methacrylate and the acetone-condensed glyceride, controlling the vacuum degree to be 3kPa, and obtaining 213.85 g (theoretical 242.43 g) of the acetone-condensed glyceride methacrylate by distilling at the top temperature of 121-122 ℃ in a rectifying tower, wherein the yield is 88.3%, the purity is 96.3% through gas chromatography analysis, the acid value is 0.005mg/g KOH, the platinum cobalt chromaticity is 35, and the moisture is 0.085%.
Comparative example 3 the catalyst was replaced with tetrabutyl titanate catalyst, otherwise identical to example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot equipped with a cooling coil is provided with a 1L esterification reactor which is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 363 g of methyl methacrylate, 160 g of acetonylglycerol, 0.61 g of polymerization inhibitor tetramethylpiperidine nitroxide free radical phosphite triester and 4.64 g of tetrabutyl titanate catalyst are added at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106.6 ℃ to start reaction, reacting for 5 hours, keeping on reacting for 11 hours, finishing the esterification reaction, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 131 ℃, controlling the temperature at the top of a rectifying tower to be 93 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after recovering the methyl methacrylate and the acetonide, controlling the vacuum degree to be 3kPa, and controlling the top temperature to be in a fraction of 121-122 ℃ to obtain 210.9 g (242.43 g in theory) of the acetonide methacrylate, wherein the yield is 87%, and the gas chromatogram of the acetonide methacrylate with the purity of 95.6% is analyzed by gas chromatography, wherein the retention time is 10.278 minutes, the acid value is 0.006mg/g KOH, the platinum cobalt chromaticity is 40, and the moisture is 0.09%.
Comparative example 4 polymerization inhibitor was replaced with TEMPO tetramethylpiperidine nitroxide, catalyst was replaced with dioctyl tin oxide catalyst, otherwise identical to example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot provided with a cooling coil is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 363 g of methyl methacrylate, 160 g of acetonylglycerol, 0.61 g of a polymerization inhibitor TEMPO tetramethylpiperidine nitrogen oxide and 4.64 g of dioctyl tin oxide catalyst are added into a 1L esterification reactor at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106.6 ℃ to start reaction, reacting for 5 hours without complete reaction, continuing to react for 5 hours to finish the esterification reaction, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 131 ℃, controlling the temperature at the top of a rectifying tower to be 93 ℃, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after recovering the methyl methacrylate and the acetone glycidyl, controlling the vacuum degree to be 1.6kPa, and obtaining 181.8 g (242.43 g of theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121-122 ℃, wherein the yield is 75%, and the purity is 96.3% through gas chromatography analysis, the acid value is 0.005mg/g KOH, the platinum cobalt chromaticity is 50, and the moisture is 0.08%.
Comparative example 5 polymerization inhibitor A TEMPO tetramethylpiperidine nitroxide was used instead of the polymerization inhibitor, otherwise as in example 6
The first step: esterification reaction
An automatic temperature-control electric heating oil bath pot provided with a cooling coil is provided with a stirring device, a thermocouple, a pressure display instrument, a rectifying tower, a reflux ratio controller, a condenser, a vacuum device and a receiving bottle, wherein 363 g of methyl methacrylate, 160 g of acetonylglycerol, 0.61 g of a polymerization inhibitor TEMPO tetramethylpiperidine nitrogen oxide and 4.64 g of a calcium acetylacetonate catalyst are added into a 1L esterification reactor at one time;
the mass content of raw material acetonide glycerol is 96.42% by gas chromatography analysis, as shown in figure 1;
Stirring the materials in the reaction kettle uniformly, heating the esterification reactor by using an electric heating oil bath pot to raise the temperature in the esterification reactor to 106.6 ℃ to start reaction, stopping heating after 5 hours, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, controlling the temperature in the esterification reactor to be 131 ℃, controlling the temperature at the top of a rectifying tower to be 93 ℃, finishing the esterification reaction, and separating a mixture of azeotrope methyl methacrylate and methanol from the top of the rectifying tower in the esterification process;
and a second step of: recovering methyl methacrylate and acetonylglycerol by vacuum rectification
Cooling to 54 ℃, starting a vacuum system to control the vacuum degree to 10.5kPa, and recovering methyl methacrylate and acetonide at the top temperature of the rectifying tower of 50-72 ℃;
and a third step of: collecting acrylic acid acetone glycidyl ester by vacuum rectification
And continuously heating the esterified liquid after recovering the methyl methacrylate and the acetone glycidyl, controlling the vacuum degree to be 1.6kPa, and obtaining 218.2 g (242.43 g of theory) of the acetone glycidyl methacrylate by fraction at the top temperature of a rectifying tower at 121-122 ℃, wherein the yield is 90%, and the purity is 97.09% through gas chromatography analysis, the acid value is 0.001mg/g KOH, the platinum cobalt chromaticity is 30, and the moisture is 0.08%.
As can be seen from the comparison of the parallel tests of the example 6 and the comparative examples 1-5, the invention has the characteristics of high product yield, good product storage, good acid value and platinum cobalt chromaticity, short esterification reaction time and shortened reaction time.
The above is only a specific embodiment of the present invention, and is not intended to limit the present invention, but various modifications and variations can be made to the present invention by those skilled in the art. Any modification, equivalent replacement, improvement, etc. made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (6)
1. A method for producing acetone glycidyl methacrylate by transesterification is characterized by comprising the following steps:
The method comprises the following specific steps:
Adding raw materials of methyl methacrylate, acetone glycidyl, a polymerization inhibitor of tetramethylpiperidine nitroxide free radical phosphite triester, and a catalyst of calcium acetylacetonate or zinc acetylacetonate into an esterification reactor which is provided with stirring and is connected with a rectifying tower, a tower top condenser and a reflux ratio controller, wherein the molar ratio of the methyl methacrylate to the acetone glycidyl is (2.6-3.1): 1, the addition amount of the polymerization inhibitor accounts for 0.303-0.454% of the mass of the acetone glycidyl, and the addition amount of the catalyst accounts for 2.5-3.5% of the mass of the acetone glycidyl; and (3) starting stirring to electrify and heat the esterification reactor, reacting at 103-107 ℃ in the esterification reactor for 3-6 h, stopping heating, controlling the reflux ratio of a reflux device at the top of the esterification reactor to be (8-12): 2, enabling the temperature in the esterification reactor to be 121-131.5 ℃, enabling the temperature at the top of a rectifying tower to be 92-96 ℃, cooling the esterification reactor to 43-54 ℃ through circulating water after the esterification is finished, carrying out reduced pressure rectification, recovering unreacted methyl methacrylate and acetone glycidyl methacrylate in the raw materials, improving the vacuum degree, and continuing the reduced pressure rectification to obtain the acetone glycidyl methacrylate.
2. The method for producing acetone glycidyl methacrylate by transesterification according to claim 1, wherein the method comprises the steps of: when the excessive raw material methyl methacrylate and acetone glycidyl are recovered by reduced pressure rectification, the vacuum degree is controlled to be 10KPa-13KPa, and the temperature of the top of the rectifying tower is 40-80 ℃.
3. The method for producing acetone glycidyl methacrylate by transesterification according to claim 1, wherein the method comprises the steps of: when the acetone glycidyl methacrylate is collected by vacuum rectification, the vacuum degree is controlled to be 1kPa-3kPa, and the temperature of the top of the rectifying tower is 120-123 ℃.
4. The method for producing acetone glycidyl methacrylate by transesterification according to claim 1, wherein the method comprises the steps of: the purity of the obtained acetone-glycidyl methacrylate product is 97% by gas chromatography analysis.
5. The method for producing acetone glycidyl methacrylate by transesterification according to claim 1, wherein the method comprises the steps of: the mass content of the acetonylglycerol is more than or equal to 96.4 percent.
6. The method for producing acetone glycidyl methacrylate by transesterification according to claim 1, wherein the method comprises the steps of: the mixture of the azeotrope methyl methacrylate and the methanol is separated from the top of the rectifying tower in the esterification process.
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