CN105801417A - Preparation method of methyl 3-methoxypropionate - Google Patents
Preparation method of methyl 3-methoxypropionate Download PDFInfo
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- CN105801417A CN105801417A CN201410847814.9A CN201410847814A CN105801417A CN 105801417 A CN105801417 A CN 105801417A CN 201410847814 A CN201410847814 A CN 201410847814A CN 105801417 A CN105801417 A CN 105801417A
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- methyl acrylate
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Abstract
The invention provides a preparation method of methyl 3-methoxypropionate. The preparation method comprises that methanol and methyl acrylate undergo an addition reaction under conditions of a mole ratio of methanol to methyl acrylate of 4-6: 1, a catalyst sodium methoxide use amount 2-3% of the total weight of methanol and methyl acrylate, a polymerization inhibitor use amount 0.2-0.3% of the total weight of methanol and methyl acrylate, an addition reaction temperature of 30-40 DEG C and methyl acrylate dropwise addition time of 1-3h, and after dropwise addition, thermal reaction time of 2-3h, the reaction solution is neutralized and then is subjected to normal pressure distillation so that unreacted methanol is distilled, and the residual reaction solution is subjected to reduced pressure distillation under pressure of -0.09MPa to -0.098MPa so that a methyl 3-methoxypropionate product is obtained. Under the above reaction conditions, methyl acrylate does not undergo a polymerization reaction so that reaction time is shortened. In the reaction, methyl acrylate is completely removed so that a reaction yield is improved, a product refining process is simple and a high purity product is obtained through simple distillation.
Description
Technical field
The present invention relates to field of medicine and chemical technology, particularly the preparation method of 3-methoxy methyl propionate.
Technical background
3-methoxy methyl propionate is the colourless liquid having peat-reek, boiling point 142-143 DEG C, to human non-toxic, is a kind of important organic solvent and organic synthesis intermediate, is widely used in the fields such as electronics industry, cleaning industry and organic synthesis.
The main preparation methods of this product is that methanol carries out additive reaction in the presence of a catalyst with acrylic acid methyl ester., then uses sulphuric acid catalyst neutralisation, last rectification to obtain target product 3-methoxy methyl propionate.
The mol ratio of the preparation method that patent 200410011392.8 discloses a kind of 3-methoxy methyl propionate, methanol and acrylic acid methyl ester. is 2.0-3.0:1, and the response time is 14h.The consumption of concentrated sulphuric acid is the 1/2 or 1/3 of catalyst mole dosage, and product is deviate from through rectifying column and reclaims product front-end volatiles.
Owing to acrylic acid methyl ester. contains double bond, being easy to be polymerized in course of reaction, therefore above-mentioned reaction needed drips acrylic acid methyl ester. very lentamente, causes the prolongation in response time, it addition, the partially polymerized decline that result also in reaction yield of acrylic acid methyl ester. in course of reaction.In above-mentioned catalysts and rear reactant liquor in possibly together with a part of unreacted acrylic acid methyl ester., the subtractive process making product becomes complicated, the purity of product also can decline to some extent, and additionally in product purification process, acrylic acid methyl ester., it also occur that polymerization, causes the blocking of rectifying column.
Summary of the invention
The present invention is in order to overcome above-mentioned technological deficiency, the preparation method providing a kind of 3-methoxy methyl propionate, the mol ratio of methanol and acrylic acid methyl ester. is 4-6:1, catalyst sodium methoxide consumption is methanol and the 2-3% of acrylic acid methyl ester. gross weight, polymerization inhibitor consumption is methanol and the 0.2-0.3% of acrylic acid methyl ester. gross weight, additive reaction temperature is 30-40 DEG C, and the time for adding of acrylic acid methyl ester. is 1-3h, insulation reaction 2-3h after completion of dropwise addition.Reactant liquor air-distillation after neutralization goes out unreacted methanol, and then under-0.09MPa to-0.098MPa, the remaining reactant liquor of decompression distillation obtains 3-methoxy methyl propionate product.
The present invention compared with prior art, has following good effect:
1, with the mol ratio of methanol, reduction reaction temperature, in the reaction addition three kinds of methods of polymerization inhibitor, ethyl acrylate is not polymerized by increase acrylic acid methyl ester. in additive reaction process, thus shortening the response time, and in additive reaction process, acrylic acid methyl ester. is fallen by complete reaction, improves reaction yield.
2, due to neutralize after reactant liquor in containing only having methanol, 3-methoxy methyl propionate product and solid sodium sulfate, the boiling point of methanol is 64.5 DEG C, the boiling point of 3-methoxy methyl propionate product is 142-143 DEG C, both differ greatly by boiling point, not with rectifying column rectification, carrying out distillation at ambient pressure and can be obtained by highly purified methanol, then the remaining reactant liquor of decompression distillation, can obtain highly purified 3-methoxy methyl propionate product.
Detailed description of the invention
In conjunction with embodiment, the present invention is further described as follows.
Embodiment 1
Four-hole boiling flask equipped with agitator, thermometer and constant pressure funnel adds methanol 192g, Feldalat NM pressed powder 8.34g, phenothiazine 0.83g, heating is to 30 DEG C, under agitation dropping acrylic acid methyl ester. 86g, time for adding is 3h, continues insulation reaction 3h at 30 DEG C after completion of dropwise addition.Under water-bath cools down, in reactant liquor, drip concentrated sulphuric acid 5.04g with catalyst neutralisation.
Reactant liquor after neutralization is layered after standing, and takes the supernatant and beats gas chromatogram, contains only the methanol of 58.86% and the 3-methoxy methyl propionate of 40.72%, do not contain acrylic acid methyl ester. in chromatogram display reactant liquor.
Under agitation in air-distillation and after reactant liquor, obtain 158g fraction.It is 94.12% that gas chromatographic analysis obtains methanol content in fraction.
Remaining reactant liquor is evacuated to-0.098MPa, proceeds by decompression distillation, obtains 112g distillate.It is 99.78% that gas chromatographic analysis obtains 3-methoxy methyl propionate content in fraction.
Calculating the productivity obtaining 3-methoxy methyl propionate is 94.7%.
Embodiment 2
Four-hole boiling flask equipped with agitator, thermometer and constant pressure funnel adds methanol 128g, Feldalat NM pressed powder 4.28g, phenothiazine 0.4g, heating is to 40 DEG C, under agitation dropping acrylic acid methyl ester. 86g, time for adding is 1h, continues insulation reaction 2h at 40 DEG C after completion of dropwise addition.Under water-bath cools down, in reactant liquor, drip concentrated sulphuric acid 3.88g with catalyst neutralisation.
Reactant liquor after neutralization is layered after standing, and takes the supernatant and beats gas chromatogram, contains only the methanol of 48.74% and the 3-methoxy methyl propionate of 50.89%, do not contain acrylic acid methyl ester. in chromatogram display reactant liquor.
Under agitation in air-distillation and after reactant liquor, obtain 119g distillate.It is 93.01% that gas chromatographic analysis obtains methanol content in distillate.
Remaining reactant liquor is evacuated to-0.09MPa, proceeds by decompression distillation, obtains 109g distillate.It is 99.64% that gas chromatographic analysis obtains 3-methoxy methyl propionate content in distillate.
Calculating the productivity obtaining 3-methoxy methyl propionate is 92.04%.
Embodiment 3
Four-hole boiling flask equipped with agitator, thermometer and constant pressure funnel adds methanol 140g, 20% sodium methoxide solution 24.6g, phenothiazine 0.49g, heating is to 30 DEG C, under agitation dropping acrylic acid methyl ester. 86g, time for adding is 2h, continues insulation reaction 2h at 30 DEG C after completion of dropwise addition.Under water-bath cools down, in reactant liquor, drip concentrated sulphuric acid 4.46g with catalyst neutralisation.Reactant liquor after neutralization is layered after standing, and takes the supernatant and beats gas chromatogram, contains only the methanol of 54.07% and the 3-methoxy methyl propionate of 45.66%, do not contain acrylic acid methyl ester. in chromatogram display reactant liquor.
Under agitation in air-distillation and after reactant liquor, obtain 151g distillate.It is 95.28% that gas chromatographic analysis obtains methanol content in distillate.
Remaining reactant liquor is evacuated to-0.095MPa, proceeds by decompression distillation, obtains 111g distillate.It is 99.69% that gas chromatographic analysis obtains 3-methoxy methyl propionate content in distillate.
Calculating the productivity obtaining 3-methoxy methyl propionate is 93.78%.
Embodiment 4
Four-hole boiling flask equipped with agitator, thermometer and constant pressure funnel adds methanol 140g, 20% sodium methoxide solution 24.6g, phenothiazine 0.49g, heating is to 30 DEG C, under agitation dropping acrylic acid methyl ester. 86g, time for adding is 2h, continues insulation reaction 3h at 30 DEG C after completion of dropwise addition.Under water-bath cools down, in reactant liquor, drip concentrated sulphuric acid 3.88g with catalyst neutralisation.Reactant liquor after neutralization is layered after standing, and takes the supernatant and beats gas chromatogram, contains only the methanol of 40.45% and the 3-ethoxyl ethyl propionate of 59.22%, do not contain acrylic acid methyl ester. in chromatogram display reactant liquor.
Under agitation in air-distillation and after reactant liquor, obtain 136g distillate.It is 93.01% that gas chromatographic analysis obtains methanol content in distillate.
Remaining reactant liquor is evacuated to-0.095MPa, proceeds by decompression distillation, obtains 110g distillate.It is 99.71% that gas chromatographic analysis obtains 3-methoxy methyl propionate content in distillate.
Calculating the productivity obtaining 3-methoxy methyl propionate is 92.95%.
Claims (2)
1. a preparation method for 3-methoxy methyl propionate, puts in reactor by methanol, catalyst and polymerization inhibitor, and dropping acrylic acid methyl ester. carries out additive reaction, after completion of dropwise addition, continue insulation reaction a period of time at the reaction temperatures, after additive reaction terminates, use concentrated sulphuric acid catalyst neutralisation；It is characterized in that: the mol ratio of methanol and acrylic acid methyl ester. is 4-6:1, catalyst sodium methoxide consumption is methanol and the 2-3% of acrylic acid methyl ester. gross weight, polymerization inhibitor consumption is methanol and the 0.2-0.3% of acrylic acid methyl ester. gross weight, additive reaction temperature is 30-40 DEG C, the time for adding of acrylic acid methyl ester. is 1-3h, insulation reaction 2-3h after completion of dropwise addition；Reactant liquor air-distillation after neutralization goes out unreacted methanol, and then under-0.09MPa to-0.098MPa, the remaining reactant liquor of decompression distillation obtains 3-methoxy methyl propionate product.
2. the preparation method of 3-methoxy methyl propionate as claimed in claim 1, it is characterised in that: described polymerization inhibitor is phenothiazine.
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| CN201410847814.9A CN105801417A (en) | 2014-12-31 | 2014-12-31 | Preparation method of methyl 3-methoxypropionate |
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| CN201410847814.9A CN105801417A (en) | 2014-12-31 | 2014-12-31 | Preparation method of methyl 3-methoxypropionate |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107721855A (en) * | 2017-10-13 | 2018-02-23 | 北京博迩科技有限公司 | A kind of method for preparing 3 methoxy methyl propionates |
| CN111018707A (en) * | 2019-12-19 | 2020-04-17 | 深圳市普利凯新材料股份有限公司 | Preparation method of methyl 3-methoxypropionate |
| CN113896639A (en) * | 2020-06-22 | 2022-01-07 | 昂吉(上海)环保新材料科技有限公司 | 3-methoxy methyl acrylate preparation system |
| WO2025021109A1 (en) * | 2023-07-25 | 2025-01-30 | 广州天赐高新材料股份有限公司 | Method for preparing methyl 3-methoxypropionate and 3-methoxy-n,n-dimethyl propionamide |
-
2014
- 2014-12-31 CN CN201410847814.9A patent/CN105801417A/en active Pending
Non-Patent Citations (2)
| Title |
|---|
| 秦丙昌等: "3-甲氧基丙酸甲酯合成工艺研究", 《应用化工》 * |
| 黄玉媛等编: "《精细化工配方常用原料手册》", 31 March 1998 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107721855A (en) * | 2017-10-13 | 2018-02-23 | 北京博迩科技有限公司 | A kind of method for preparing 3 methoxy methyl propionates |
| CN107721855B (en) * | 2017-10-13 | 2021-01-19 | 北京博迩科技有限公司 | Method for preparing 3-methoxy methyl propionate |
| CN111018707A (en) * | 2019-12-19 | 2020-04-17 | 深圳市普利凯新材料股份有限公司 | Preparation method of methyl 3-methoxypropionate |
| CN113896639A (en) * | 2020-06-22 | 2022-01-07 | 昂吉(上海)环保新材料科技有限公司 | 3-methoxy methyl acrylate preparation system |
| WO2025021109A1 (en) * | 2023-07-25 | 2025-01-30 | 广州天赐高新材料股份有限公司 | Method for preparing methyl 3-methoxypropionate and 3-methoxy-n,n-dimethyl propionamide |
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Application publication date: 20160727 |