Preparation method of monomethyl fumarate

A technology of monomethyl fumarate and monomethyl maleate, which is applied in the field of preparation of monomethyl fumarate, can solve the problems of increasing production costs and unfavorable industrial production, and achieve energy-saving reaction time and environmental protection performance Good results

Inactive Publication Date: 2010-07-14
HENAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The technical problem to be solved in the present invention is that the preparation of monomethyl fumarate uses a large amount of organic solvents, which increases the production cost and is unfavorable for industrialized production. A method for preparing monomethyl fumarate is provided

Method used

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  • Preparation method of monomethyl fumarate

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of fumaryl chloride

[0028] Add 58.0g (0.5mol) of fumaric acid and a few drops of catalyst in the reaction flask equipped with an acid gas recovery device, and then add 178.5g (1.5mol, excess) of SOCl 2 . Heat to reflux until the fumaric acid is completely reacted. Atmospheric distillation recovered excess thionyl chloride, and then vacuum distillation to collect fractions at 80-82°C / 0.09MPa to obtain 71 g of light yellow liquid, namely fumaryl chloride, with a yield of 92%.

[0029] Preparation of monomethyl fumarate

[0030] Put 49g (0.5mol) of maleic anhydride and 12.8g (0.4mol) of anhydrous methanol into the reaction flask, stir and react at room temperature, the temperature of the system automatically rises to about 35°C, react for 30 to 40 minutes, and the maleic anhydride is completely dissolved. Add 6.4 g (0.2 mol) of anhydrous methanol, and heat to 55° C. in a water bath to continue the reaction for 30 minutes.

[0031] Heat the above reaction ...

Embodiment 2

[0033] Preparation of monomethyl fumarate

[0034] Put 49g (0.5mol) of maleic anhydride and 12.8g (0.4mol) of anhydrous methanol into the reaction flask, stir and react at room temperature, the temperature of the system automatically rises to about 35°C, react for 30 to 40 minutes, and the maleic anhydride is completely dissolved. Add 6.4 g (0.2 mol) of anhydrous methanol, and heat to 55° C. in a water bath to continue the reaction for 30 minutes.

[0035] Add a certain amount of ethyl acetate to the above reaction system, heat, adjust the temperature of the hot bath to 90°C, add 3.06g (0.02mol) fumaryl chloride to the reaction system, and the temperature of the reaction system rises sharply to 90°C. After reacting for 2 minutes, crystals began to separate out in the solution, and solidified quickly. Under the condition of heat preservation, the temperature of the reaction system will further increase to 96°C. After 10 minutes of heat preservation, the temperature of the system...

Embodiment 3

[0037] Preparation of monomethyl fumarate

[0038] Put 98g (1.0mol) of maleic anhydride and 28.8g (0.9mol) of anhydrous methanol into the reaction flask, stir and react at room temperature, the temperature of the system automatically rises to about 35°C, react for 30-40 minutes, and the maleic anhydride is completely dissolved. Add 6.4 g (0.2 mol) of anhydrous methanol, and heat to 55° C. in a water bath to continue the reaction for 30 minutes.

[0039] After adding a certain amount of ethyl acetate to the above reaction system and heating to a system temperature of 85° C., 1.53 g (0.01 mol) of fumaryl chloride was added to the reaction system, and the temperature of the reaction system rose sharply to 90° C. After reacting for 2 minutes, crystals began to separate out in the solution, and solidified quickly. The reaction temperature of the system was further increased to 95°C, and after 10 minutes of heat preservation, the system temperature began to decrease, and the temper...

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Abstract

The invention discloses a preparation method of monomethyl fumarate. A main material of maleic anhydride and methanol are subjected to alcoholysis reaction, thus producing monomethyl maleate, which is then isomerized to produce the monomethyl fumarate. The preparation method comprises the following steps: the main material of the maleic anhydride and the methanol are subjected to the alcoholysis reaction, thus producing the monomethyl maleate; then the monomethyl maleate solution is added with ethyl acetate and is then added with fumaryl chloride at 80-100DEG C for reacting for 60-120 minutes, then the ethyl acetate is removed by distillation, water is added, the product is heated to dissolve, and after cooling, centrifugal separation and vacuum drying, the monomethyl fumarate is obtained. The alcoholysis reaction process can be completed at room temperature, which saves energy and has short reaction time; and the isomerization reaction of the monomethyl maleate and the alcoholysis reaction of the maleic anhydride can adopt the same set of equipment, and the isomerization reaction can be carried out as soon as the alcoholysis reaction is completed, thus having no need for new devices.

Description

technical field [0001] The invention relates to a preparation method of monomethyl fumarate. Background technique [0002] Mold is extremely harmful to the health and life safety of humans, livestock and poultry, and a small amount of compounds that can inhibit the growth of microorganisms are often added to food and feed to achieve the purpose of preventing mold. Antifungal agents used in food and feed mainly include benzoic acid and its salts, sorbic acid and its salts, paraben esters, propionic acid and its salts, dimethyl fumarate, dehydroacetic diacetic acid Sodium etc. Dimethyl fumarate (Dimethyl Fumarate, referred to as DMF) is a high-efficiency broad-spectrum preservative, which sublimates at room temperature, can effectively inhibit the growth of microorganisms in the system environment, and play a role in high-efficiency antiseptic, so it is widely used . However, DMF is irritating to human skin and eyes, and can cause skin allergies when in contact with the hum...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/60C07C67/333
Inventor 谷国团许英田玉平
Owner HENAN UNIVERSITY
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