A kind of method based on acid anhydride synthesis acryloyl morpholine

A technology of acryloyl morpholine and morpholine, which is applied in the field of compound synthesis, can solve the problems of poor stability of acryloyl chloride, difficult control of the reaction process, and high corrosiveness of the reactor, and achieves stable product quality, easy reaction control and low cost. Effect

Active Publication Date: 2016-08-24
WUXI HIT SAINT OPTOELECTRONICS MATERIAL TECH CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Chinese patent CN101293880B discloses a method for preparing acryloyl morpholine using the acylation reaction method of acryloyl chloride. Acryloyl chloride is generated after phosphorus trichloride is acylated with acrylic acid, and acryloyl chloride is solvated and then acylated with morpholine to obtain Crude acryloyl morpholine, and then rectifying the reaction solution under vacuum conditions, can obtain high-purity acryloyl morpholine, the yield and purity are high, but the process route is long, and the stability of the intermediate product acryloyl chloride is poor. Its double bond is relatively active, prone to various side reactions, and the yield and purity are low. In addition, the by-product of the reaction is hydrochloric acid, which is highly corrosive to the reactor, and the post-processing of the product is complicated, which increases the production cost.
The process route of the whole reaction process is long, and the reaction process is not easy to control

Method used

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  • A kind of method based on acid anhydride synthesis acryloyl morpholine
  • A kind of method based on acid anhydride synthesis acryloyl morpholine
  • A kind of method based on acid anhydride synthesis acryloyl morpholine

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Experimental program
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Effect test

Embodiment 1

[0033] (1) Add 72g of acrylic acid and 164g of trichloroacetic acid in a four-necked flask to mix, add 5g of phosphorus pentoxide, add 2.6 grams of polymerization inhibitor, and add 110g of acetic anhydride dropwise to the above mixed solution. The reaction was carried out for 5 hours.

[0034] (2) Distill under reduced pressure after the completion of the reaction, remove the former fraction, and obtain 165 g of the product, which is acrylic acid trichloroacetic anhydride.

[0035] (3) Add 165g of acid anhydride into the solvent, lower the temperature to 0°C, add dropwise 72g of morpholine, and add 76.5g of triethylamine, keep the reaction temperature at 3°C, and finish the reaction for 2 hours to obtain crude acryloylmorpholine.

[0036] (4) Filtrate the crude acryloyl morpholine, add a polymerization inhibitor to distill under reduced pressure, collect fractions at 140-160° C., and obtain 96 g of the product, which is the final product acryloyl morpholine. The polymerizati...

Embodiment 2

[0039] (1) Add 900g of acrylic acid and 1025g of trichloroacetic acid in the reaction kettle to mix, add 50g of phosphorus pentoxide, add 26 grams of polymerization inhibitor, add 1100g of acetic anhydride to the above mixed solution dropwise, after the dropwise addition is completed, heat the mixture at 100°C Under the condition of reaction for 3 hours.

[0040] (2) Distill under reduced pressure after completion of the reaction to remove the front fraction to obtain 2071 g of acrylic acid trichloroacetic anhydride.

[0041] (3) Add 2071g of acid anhydride into the solvent, dropwise add 826.5g of morpholine, and add 682.5g of pyridine, keep the reaction temperature at 5°C, and react for 1 hour after the dropwise addition, to obtain crude acryloylmorpholine.

[0042] (4) Filtrate the crude acryloylmorpholine, add a polymerization inhibitor to distill under reduced pressure, collect fractions at 140-160°C, and obtain 1193 g of the product, which is the final product acryloylmor...

Embodiment 3

[0045] (1) Add 135g of acrylic acid and 615g of trichloroacetic acid in a four-necked flask to mix, add 10g of phosphorus pentoxide, add 5.2 grams of polymerization inhibitor, and add 200g of acetic anhydride dropwise to the above mixed solution. The reaction was carried out for 5 hours.

[0046] (2) Distill under reduced pressure after completion of the reaction, remove the front cut, and obtain 311g of acrylic acid trichloroacetic anhydride.

[0047] (3) Add 311g of acid anhydride into the solvent, lower the temperature to 0°C, add 186g of morpholine dropwise, and add 158.5g of N-methylmorpholine, keep the reaction temperature at 0°C, and drop the reaction for 4 hours to obtain the crude acryloyl Morpholine.

[0048] (4) Filtrate the crude acryloylmorpholine, add a polymerization inhibitor to distill under reduced pressure, collect fractions at 140-160°C, and obtain 181 g of the product, which is the final product acryloylmorpholine. The polymerization inhibitor is methyl ...

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Abstract

The invention discloses a method for synthesizing acryloyl morpholine based on anhydride. The acryloyl morpholine monomer is generated by performing a reaction of the acrylate trichloroacetic anhydride and the morpholine, and the acrylate trichloroacetic anhydride is obtained by performing a reaction of the acrylic acid and the trichloroacetic acid. The method for synthesizing acryloyl morpholine provided by the invention is simple in process route, easy for reaction control, mild in reaction condition, cheap in raw material, stable in product structure and low in cost; and besides, the method also increases the purity and yield of the product and has an industrial application prospect.

Description

technical field [0001] The invention relates to a method for synthesizing acryloylmorpholine, in particular to a method for synthesizing acryloylmorpholine based on an acid anhydride, and belongs to the field of compound synthesis. Background technique [0002] Acryloylmorpholine (ACMO) is a water-soluble compound with carbon-carbon unsaturated double bonds. It is a colorless or light yellow transparent liquid. Its structural formula is: [0003] Because acryloyl morpholine itself is non-toxic and has good biocompatibility, its homopolymer is often used as a drug slow-release agent, cosmetic propping agent, etc. In recent years, acryloyl morpholine has replaced toxic propylene in the field of water purification treatment. Amides are used as water treatment agents. Acryloyl morpholine is also an excellent additive and modifier for synthetic resins. It is used as a reactive diluent for UV-curable resins. It is easy to copolymerize with acrylic acid, acrylamide, gelatin, etc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/185
CPCC07D295/185
Inventor 杨恺陈君李松
Owner WUXI HIT SAINT OPTOELECTRONICS MATERIAL TECH CO LTD
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