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Preparation method of N-acryloyl morpholine

A technology of acryloyl morpholine and morpholine, which is applied in the field of condensation preparation of N-acryloyl morpholine, can solve the problems of side reactions, poor stability of acryloyl chloride, long process route, etc., and achieves mild preparation conditions and easy availability of raw materials Strong, low overall cost effect

Pending Publication Date: 2019-11-22
苏州双格新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 with high yield and purity, but the intermediate product acryloyl chloride has poor stability and its double bond is relatively active , a variety of side reactions are prone to occur. In addition, the by-products of the reaction are hydrochloric acid and phosphoric acid, which are 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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  • Preparation method of N-acryloyl morpholine

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Take 72.06g (1.0mol) of acrylic acid, 350mL of dichloroethane, 0.27g of p-hydroxyanisole, and 0.81g of cuprous chloride into a 1000mL four-necked flask and keep it at 25°C. Take morpholine 87.12g (1.0mol), control the temperature at 25±2℃, and add morpholine dropwise. After the reaction, it was filtered, and the filter cake was washed and dried in vacuo to obtain 155.2 g of yellow solid morpholine acrylate. It was added to 300 mL DMF, heated to 135°C, and 69.2 g of phosphorus pentoxide was added in three portions. After the reaction is over, the low boiling components are removed, and then 20% sodium hydroxide solution is added for neutralization. Add 1,2-dichloroethane for extraction, wash with saturated sodium chloride, add 0.23g of p-hydroxyanisole and 0.69g of cuprous chloride to the combined organic phase, distill 1,2-dichloroethane to reduce pressure, The N-acryloyl morpholine was further distilled at elevated temperature to obtain 109.52 g of N-acryloyl morpholi...

Embodiment 2

[0035] Take 72.06g (1.0mol) of acrylic acid, 350mL of ethanol, 0.27g of phenothiazine, and 0.51g of butylcatechol into a 1000mL four-neck flask and keep it at 10°C. Take morpholine 87.12g (1.0mol), control the temperature to 10±2℃, and add morpholine dropwise. After the reaction, it was filtered, and the filter cake was washed and dried in vacuum to obtain 151.5 g of yellow solid morpholine acrylate. Add it to 250mL dimethyl sulfoxide, heat to 135℃, add 69.2g of acetic anhydride in three portions, after the reaction is over, remove the low boiling components, then add 20% sodium carbonate solution to neutralize, add 1,2 -Dichloroethane extraction, saturated sodium chloride washing, adding 0.2g hydroquinone, 0.74g picric acid, and then distilling to recover 1,2-dichloroethane, reducing the pressure and increasing the temperature to further distill N-acryloyl To obtain 103.6 g of N-acryloylmorpholine, the yield was 73.4%, and the purity was 99.1%.

Embodiment 3

[0037] Take 72.06g (1.0mol) of acrylic acid, 350mL of dichloroethane, 0.27g of hydroquinone, and 0.81g of cuprous chloride into a 1000mL four-necked flask and keep it at 45°C. Take morpholine 87.12g (1.0mol), control the temperature at 45±2℃, and add morpholine dropwise. After the reaction, it was filtered, and the filter cake was washed and dried in vacuum to obtain 155.4 g of yellow solid morpholine acrylate. Add it to 350mL of dioxane, heat to 160°C, add 69.2g of phosphorus pentoxide in three times, after the reaction is over, remove the low boiling components, then add calcium hydroxide emulsion solution to neutralize, filter The filtrate is extracted with ethyl acetate, washed with saturated sodium chloride, 0.3g tert-butylphenol, 0.3g nitrobenzene, and then distilled to recover ethyl acetate, reduce the pressure, and raise the temperature to further distill N-acryloylmorpholine to obtain The yield of 107.6 g of N-acryloylmorpholine was 76.2%, and the purity was 99.0%.

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Abstract

The invention discloses a preparation method of N-acryloyl morpholine, and particularly relates to a method for preparing N-acryloyl morpholine by a condensation method; acrylic acid and morpholine are used as raw materials, and a dehydrating agent is used for dehydration. The preparation conditions are mild, and the purification process is simple; the product is easy to separate and not easy to polymerize; the preparation method has the advantages of high yield, high product purity and the like in product synthesis.

Description

Technical field [0001] The invention relates to a preparation method of N-acryloyl morpholine, in particular to a condensation preparation method of N-acryloyl morpholine. Background technique [0002] N-acryloyl morpholine (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 ACMO itself is non-toxic and has good biocompatibility, its homopolymer can be used as a drug slow release agent, beauty proppant, etc.; ACMO is also a functional monomer and active diluent with excellent performance. Double bond and morpholine group are water and oil amphoteric UV curing agent monomers. They have relatively active chemical properties (high sensitivity), and will not produce any pungent odor (very low odor), and have low viscosity, fast curing, Features such as strong dilution capacity. The UV and EB cured resin modified by ACMO has very low moisture absorption, and h...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185
CPCC07D295/185
Inventor 杨恺李现松傅泽恒
Owner 苏州双格新材料科技有限公司
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