Synthetic improvement method of acryloylmorpholine

A technology based on acryloylmorpholine and morpholino, applied in the field of organic synthesis, can solve problems such as difficult separation of acryloylmorpholine, difficult control of thermal cracking reaction, serious thermal polymerization of products, etc., to achieve easy separation of products and excellent reaction conditions Ease of control and less effect of aggregation phenomenon

Active Publication Date: 2014-05-07
CHANGZHOU XIAOGUO INFORMATION SERVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0012] Although this synthetic method avoids the use of acid chlorides, the raw materials are not easy to obtain, and the thermal cracking reaction is difficult to control, the product thermal polymerization is serious, and the yield is only 29%.
4-Morpholinylpropionylmorpholine is not easy to separate the product acryloylmorpholine

Method used

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  • Synthetic improvement method of acryloylmorpholine
  • Synthetic improvement method of acryloylmorpholine
  • Synthetic improvement method of acryloylmorpholine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 6.00 g (0.070 mol) of methyl acrylate, 5.11 g (0.07 mol) of diethylamine, and 0.30 g (0.0024 mol) of p-hydroxyanisole into a 100 mL four-neck flask, and keep the temperature at 65°C to 68°C for 1 hour After finishing the reaction, the reaction solution was evaporated under reduced pressure to obtain 8.85g (0.060mol) of methyl 3-methoxy-diethylpropionate, and 6.26g (0.072mol) of morpholine and 0.32g (0.006mol) of sodium methoxide were added , keep the temperature at 80°C to 85°C, react for 5 to 8 hours, after the end, add hydrochloric acid to neutral, and rotary evaporate under reduced pressure to obtain the crude product 3-morpholinyl-diethylpropionamide, then add methanol to dissolve, and filter with suction In addition to sodium chloride, the mother liquor was rotary evaporated under reduced pressure to obtain 7.20 g of 3-morpholino-diethylpropionamide. Continue to add 0.30 g (0.0024 mol) of polymerization inhibitor, and distill under reduced pressure to obtain 3....

Embodiment 2

[0041] Add 6.00 g (0.070 mol) of methyl acrylate, 10.22 g (0.14 mol) of diethylamine, and 0.30 g (0.0024 mol) of p-hydroxyanisole into a 100 mL four-neck flask, and keep the temperature at 65°C to 68°C for 1 hour After finishing the reaction, the reaction solution was evaporated under reduced pressure to obtain 9.03g (0.062mol) of methyl 3-methoxy-diethylpropionate, and 10.79g (0.124mol) of morpholine and 3.35g (0.062mol) of sodium methoxide were added , keep the temperature at 80°C to 85°C, react for 5 to 8 hours, after the end, add hydrochloric acid to neutral, and rotary evaporate under reduced pressure to obtain the crude product 3-morpholinyl-diethylpropionamide, then add methanol to dissolve, and filter with suction In addition to sodium chloride, the mother liquor was rotary evaporated under reduced pressure to obtain 7.53 g of 3-morpholino-diethylpropionamide. Continue to add 0.30 g (0.0024 mol) of polymerization inhibitor, and distill under reduced pressure to obtain ...

Embodiment 3

[0043] Add 6.00 g (0.070 mol) of methyl acrylate, 7.66 g (0.10 mol) of diethylamine, and 0.30 g (0.0024 mol) of p-hydroxyanisole into a 100 mL four-neck flask, and keep the temperature at 65°C to 68°C for 1 hour After finishing the reaction, the reaction solution was evaporated under reduced pressure to obtain 8.83g (0.061mol) of methyl 3-methoxy-diethylpropionate, and 6.35g (0.073mol) of morpholine and 1.65g (0.031mol) of sodium methoxide were added , keep the temperature at 80°C to 85°C, react for 5 to 8 hours, after the end, add hydrochloric acid to neutral, and rotary evaporate under reduced pressure to obtain the crude product 3-morpholinyl-diethylpropionamide, then add methanol to dissolve, and filter with suction In addition to sodium chloride, the mother liquor was rotary evaporated under reduced pressure to obtain 7.82 g of 3-morpholino-diethylpropionamide. Continue to add 0.30 g (0.0024 mol) of polymerization inhibitor, and distill under reduced pressure to obtain 3....

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Abstract

The invention relates to a synthetic improvement method of acryloylmorpholine, and belongs to the field of organic synthesis. The method comprises the following steps: performing Michael addition on diethylamine and methyl acrylate which are taken as raw materials so as to generate 3-methoxy-diethyl methyl propionate; then performing an amidation reaction by adding morpholine so as to generate 3-morpholinyl-diethyl propionamide; and finally performing a catalytic cracking reaction so as to obtain a target product, namely, the acryloylmorpholine. The method is simple and short in process, easy in raw material obtainment, simple in equipment, easy in reaction condition control, moderate in preparation condition and simple in purification refining process. The acryloylmorpholine is stable, easy to separate and is difficult to polymerize.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing acryloylmorpholine. Background technique [0002] N-acryloylmorpholine (ACMO) is a functional monomer and reactive diluent with excellent performance. Due to its double bond and morpholine group, its chemical properties are relatively active (high sensitivity), and it does not produce any pungent odor (odor Very low), and has the characteristics of low viscosity, fast curing and strong dilution ability. The UV and EB curable resin modified by ACMO has very low hygroscopicity, and has good acid resistance, alkali resistance and solvent resistance. Its structural formula is shown in formula 1 below: [0003] [0004] Formula 1 Acryloylmorpholine chemical structure [0005] According to existing literature reports, the synthesis of N-acryloyl morpholine is generally prepared by one-step reaction of acryloyl chloride and morpholine as raw m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/185
CPCC07D295/185
Inventor 宋国强罗九艳曹引梅姚昶旭张文楠
Owner CHANGZHOU XIAOGUO INFORMATION SERVICES
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