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Preparation process of MAME (methyl 3-methoxyacrylate)

A technology of methyl methoxyacrylate and methyl dimethoxypropionate, which is applied in the field of organic compound synthesis, can solve the problems of low reaction yield, severe exotherm, low yield and the like, and achieves high yield, The preparation process is simple and efficient, and the effect of considerable economic benefits

Inactive Publication Date: 2018-04-06
淄博齐塑环保科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] 3-Methoxymethyl acrylate (MAME) is a colorless and transparent liquid, a multifunctional compound with good reactivity, and is an important C-3 building block in organic synthesis, widely used in pesticides, medicines and polymers In the field of materials and other fields, it is used to synthesize a variety of organic compounds. It has a wide range of uses and a large demand. However, domestic industrialization is less and most rely on imports.
[0003] The currently reported synthesis methods of MAME are as follows: 1) Wacker catalytic oxidation method: PdCl 2 and CuCl 2 As a catalyst, it catalyzes the efficient oxidation of acrylic acid and methanol into 3,3-dimethoxymethyl propionate and 3-methoxymethyl acrylate, and the conversion rate of acrylic acid reaches 95.2%. This method is simple and efficient, but the catalyst is expensive and difficult to recycle. 2) Methyl propiolate method: Methyl propiolate and ethanol are catalyzed by sodium cyanide or potassium carbonate to synthesize methyl 3,3-diethoxypropionate, cyanide The catalytic yield of sodium chloride is 75%, and the catalytic yield of potassium carbonate is 70%. The process is mature, but propiolic acid is expensive, the yield is not high, and sodium cyanide is highly toxic; 3) trimethyl orthoformate and Ketene method: ketene and trimethyl orthoformate are catalyzed by montmorillonite or boron trifluoride ether to prepare methyl 3,3-dimethoxypropionate, and then catalyzed by p-toluenesulfonic acid or similar substances Cracking to prepare methyl 3-methoxyacrylate, the reaction yield is not high, 52%, and the reaction process is violently exothermic; 4) Carbon tetrachloride method: Synthesize 1 with carbon tetrachloride and vinyl ether as raw materials , 1,1,3-Tetrachloro-3-ethoxypropane, reflux esterification of propane compound and methanol to prepare 3,3-dimethoxypropionate methyl ester, and then synthesize 3-methoxymethyl acrylate by cracking , the yield of the target product in this method is also low

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Composition of raw materials in this example: 560g of methyl acrylate, 716g of methanol, 2.24g of cobalt oxide, 8.96g of indium oxide, and 17.6g of concentrated sulfuric acid;

[0018] making process:

[0019] Add methyl acrylate, methanol and synthesis catalyst to the reaction kettle, stir evenly, keep the temperature of the reaction solution at 50°C, and fill the reaction kettle with nitrogen and oxygen so that the partial pressures of nitrogen and oxygen are 0.4MPa respectively, and start the reaction. The reaction time is 16 hours, and when the content of methyl acrylate in the reaction solution is 3%, the reaction ends and the addition etherification reaction product is obtained.

[0020] Filter the addition etherification reaction product to recover the catalyst, add petroleum ether to the filtrate, stir evenly, let it stand for stratification, the upper layer is petroleum ether layer, and recover petroleum ether by atmospheric distillation to obtain the intermedi...

Embodiment 2

[0025] The difference between this example and Example 1 is that the synthetic catalyst is cobalt oxide, and the mass of cobalt oxide is 5.6 g; the preparation process is the same as that of Example 1.

[0026] The target product that present embodiment makes is 507g, is 78% based on methyl acrylate, and product purity is 94.1%.

Embodiment 3

[0028] The difference between this example and Example 1 is that the synthetic catalyst is indium oxide, and the mass of indium oxide is 16.8 g; the preparation process is the same as that of Example 1.

[0029] The target product that present embodiment makes is 520g, is 80% based on methyl acrylate, and product purity is 94.5%.

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PUM

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Abstract

The invention provides a preparation process of MAME (methyl 3-methoxyacrylate) and belongs to the technical field of synthesis of organic compounds. According to the preparation process, methyl acrylate and excess methanol taken as starting raw materials are subjected to an addition-etherification reaction in an oxygen atmosphere under the action of a synthetic catalyst, a product is subjected tofiltration and extraction, methyl 3,3-dimethoxypropionate is obtained and subjected to a catalytic cracking reaction, MAME and methanol are generated, the target product MAME is obtained through distillation, and methanol is recovered, wherein the synthetic catalyst is cobalt oxide, indium oxide or a mixture of cobalt oxide and indium oxide in any proportion. The preparation process is simple andefficient, the yield of the product MAME is higher and reaches 78%-82.4%, the catalyst can be recycled for a long time, corrosive and toxic substances are avoided, reaction equipment cannot be corroded, industrial production can be realized, and considerable economic benefits are created.

Description

technical field [0001] The invention discloses a process for preparing methyl 3-methoxyacrylate, which belongs to the technical field of organic compound synthesis. Background technique [0002] 3-Methoxymethyl acrylate (MAME) is a colorless and transparent liquid, a multifunctional compound with good reactivity, and is an important C-3 building block in organic synthesis, widely used in pesticides, medicines and polymers In the field of materials and other fields, it is used to synthesize a variety of organic compounds. It has a wide range of uses and a large demand. However, domestic industrialization is less and most rely on imports. [0003] The currently reported synthesis methods of MAME are as follows: 1) Wacker catalytic oxidation method: PdCl 2 and CuCl 2 As a catalyst, it catalyzes the efficient oxidation of acrylic acid and methanol into 3,3-dimethoxymethyl propionate and 3-methoxymethyl acrylate, and the conversion rate of acrylic acid reaches 95.2%. This metho...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/327C07C69/734C07C67/54
CPCC07C67/31C07C67/327C07C67/54C07C69/734Y02P20/584
Inventor 李勇宋毅盛慧超
Owner 淄博齐塑环保科技有限公司
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