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Process for preparing n-methyl(METH)acrylamide

A technology of acrylamide and methyl, applied in the field of preparing N-methacrylamide, achieves the effect of complete atom economy and low loss

Active Publication Date: 2021-03-09
EVONIK OPERATIONS GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, there are the same disadvantages as in DE102011089363

Method used

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  • Process for preparing n-methyl(METH)acrylamide
  • Process for preparing n-methyl(METH)acrylamide
  • Process for preparing n-methyl(METH)acrylamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Embodiment 1: the preparation of N-methylmethacrylamide

[0048] Reaction equation:

[0049]

[0050] Apparatus: 2 liter autoclave with glass insert, Ni-Cr-Ni thermocouple, gas feed: metal, steel methylamine cylinder, manometer, acetone / dry ice bath

[0051] mixture:

[0052] 6.0mol methacrylic anhydride = 940.2g

[0053] 6.0mol methylamine, gas=186.4g

[0054] Theoretical yield: (=starting weight) 1126.6g

[0055] Procedure: The methacrylic anhydride was initially added to the glass insert of the autoclave and the autoclave was screwed shut. The steel methylamine cylinder was equilibrated and connected to the autoclave by a coiled VA feed tube; thus the loss in weight as methylamine was introduced could be monitored.

[0056] The introduction of methylamine was started at room temperature at a metering rate of about 4 g / 3 min. The reaction is strongly exothermic. The temperature should not exceed 40°C (35°C±5°C). The mixture was cooled with an acetone-dry ice ...

Embodiment 2

[0061] Example 2: Workup of N-methylmethacrylamide by distillation

[0062] Apparatus: 2 liter three-neck round bottom flask with boiling capillary, Pt100 temperature sensor, 30 cm mirrored column fitted with 8 x 8 Raschig rings, automatic column head (dispenser), reflux Condenser, coiled condenser, Thiele-Anschütz connection, receiver, oil bath, vacuum pump, pressure gauge

[0063] mixture:

[0064] 1122 g of N-methylmethacrylamide obtained from Example 1

[0065] 22.4mg 4-Hydroxy-2,2,6,6-tetramethylpiperidin-1-oxyl (free radical) (20ppm)

[0066] 224.4mg hydroquinone monomethyl ether (200ppm)

[0067] 1122mg octadecyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate (1000ppm)

[0068] Operation process:

[0069]

[0070] RR = reflux ratio

[0071] Yield and GC analysis:

[0072]

[0073] *Viscous, additional peaks: 11.257 minutes: 25.653%; 11.688 minutes: 15.458%; 12.259 minutes: 5.177% + additional smaller peaks

Embodiment 3

[0074] Embodiment 3: Preparation of N-methylmethacrylamide in solvent

[0075] Apparatus: 1 liter four-neck round bottom flask with precision glass stirrer (PTFE sleeve), Pt100 temperature sensor, gas inlet (PTFE), gas outlet of PTFE with There are wash bottles as safety bottles, reflux condensers, steel methylamine cylinders, exhaust ducts leading directly into fume hoods, compressed air as feed for added air, acetone / dry ice cooling bath

[0076] mixture:

[0077] 1.0mol methacrylic anhydride = 156.4g

[0078] 250ml methyl tert-butyl ether (MTBE)

[0079] 1.0mol methylamine, gas

[0080] Theoretical yield: 99.1g

[0081] Procedure: Add methacrylic anhydride and MTBE initially and allow to cool. Methylamine gas was introduced at about 2°C-10°C. The reaction is slightly exothermic.

[0082] Since the reaction proceeds only very slowly at this temperature, the gas is introduced more quickly and the bottom temperature can be raised up to 50°C. The introduction was termin...

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Abstract

The invention relates to a process for preparing N-methyl(meth)acrylamide and to the uses thereof.

Description

technical field [0001] The present invention relates to a process for the preparation of N-methyl(meth)acrylamide. Background technique [0002] N-Methyl(meth)acrylamide can be prepared by reacting an acid halide and methylamine. In this case, however, an additional equivalent of base is required, by which the hydrogen halide formed is scavenged. In case of doubt, this base is methylamine itself, which requires two equivalents of methylamine, which would adversely affect the economic feasibility of the preparation. [0003] DE 4027843 describes in general terms another preparation, a continuous process for the preparation of N-substituted acrylamides and methacrylamides. In this process, the corresponding N-substituted propenes are obtained by reacting alkyl esters of acrylic acid or alkyl methacrylic acid with aliphatic or aromatic amines in a continuous mode in a molar ratio of 1:≥2 amides and methacrylamides. Similar to the preparation with acid chlorides, this method...

Claims

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Application Information

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IPC IPC(8): C07C231/02C07C233/09C08F220/56
CPCC07C231/02C08F220/54Y02P20/582C07C233/09C07C231/24C08F220/56
Inventor M·特雷斯科D·萨尔T·舒茨S·克里尔
Owner EVONIK OPERATIONS GMBH
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