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Method for producing N-methyl-N-vinylacetamide having improved stability and polymerizability

一种乙烯基乙酰胺、甲基乙酰胺的技术，应用在N-甲基-N-乙烯基乙酰胺聚合而成的聚合物领域，能够解决不易获得聚合物等问题，达到品质稳定的效果

Inactive Publication Date: 2010-12-08
RESONAC HOLDINGS CORPORATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These polymers can be used in contact lenses, tackifiers for oil drilling, gas hydrate inhibitors, coating agents, materials for biomaterials, substrates for DDS, substrates for cosmetics, lubricant additives for fuels, coagulants, liquid absorbents , tackifier, etc., but when performing homopolymerization or copolymerization, since the polymerizability of the raw material monomers varies between production batches, it is difficult to obtain polymers with target physical properties such as molecular weight and residual monomer concentration. question

Method used

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Examples

Experimental program
Comparison scheme
Effect test

manufacture example 1

[0091] Add 7.31g (0.1 mol) of N-methylacetamide, 21.47g (0.67 mol) of methanol, 2.16g (15 mmol) of ethylenebis( N-methylacetamide), 9.01g (0.1 mole) of acetaldehyde dimethyl acetal, stirred at 45-48°C until uniform, and dissolved. A liquid obtained by dissolving 0.04 g (0.1% by mass relative to the above total addition amount) of concentrated sulfuric acid in 1.06 g (33 mmol) of isopropanol (the same applies to the following examples) was added and stirred, and then dripped 17.62 g (0.4 mol) of acetaldehyde was added into the funnel in 3 portions. After the dropwise addition, the reaction was carried out at 50° C. for 3 hours to neutralize the catalyst, and then quantified by gas chromatography. As a result, the conversion rate of N-methylacetamide was 86%, and N-(1-methoxyethyl) The selectivity of -N-methylacetamide was 93%, and the selectivity of ethylenebis(N-methylacetamide), a by-product, was 5.2%. Starting from the resulting reaction solution, N-(1-methoxyethyl)-N-meth...

Embodiment 1

[0094] The pyrolysis liquid obtained in Production Example 1 was distilled under the following conditions. Fill glass beads in a 20mm×500mm distillation column, and process with a reflux ratio of 0.3 (designated distillation stages: about 10 stages). The main fraction was divided into Fraction 1 to Fraction 7 each 50 mL from the initial fraction at 63° C. (21 mmHg), and bottoms. Then, the above-mentioned Fraction 2 and Fraction 3 were mixed and simply distilled to obtain N-methyl-N-methyl-N-methyl-N-N-methyl-N-methyl-N-methyl-N-methyl-N-methyl-N-methyl-N-N-methyl-N-methyl-N-methyl-N-methyl-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-methyl-N-N-N-methyl-N-N-methyl-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N-N- which had a purity of 97.5% and a content of N-1,3-butadienyl-N-methylacetamide of 146 ppm. vinyl acetamide. When the polymerizability evaluation test was performed in t...

Embodiment 2

[0096] 245 g of potassium tert-butoxide (potassium tert-butoxide / N-vinylacetamide=1.2 (molar ratio)) was added to a liquid mixture of 150 g of Showa Denko Co., Ltd. N-vinylacetamide and 2680 g of THF. Then, 302 g of methyl iodide (99.5%) was added and stirred (methyl iodide / N-vinylacetamide=1.2 (molar ratio)). The mixed liquid in slurry state was filtered with filter paper (5C), and the filtrate was concentrated (40° C.) with an evaporator. Then, distillation was performed at 20 mmHg and 65° C. to obtain N-methyl-N-vinylacetamide with a purity of 98% (total yield: 69%). Furthermore, the obtained N-methyl-N-vinylacetamide was a colorless transparent liquid, and the concentration of N-1,3-butadienyl-N-methylacetamide was 30 ppm. When the polymerizability evaluation test was performed in the same manner as in Production Example 1, the viscosity was 160 mPa·s.

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Abstract

Disclosed is a method for producing N-methyl-N-vinylacetamide, which comprises a step for controlling the N-1,3-butadienyl-N-methylacetamide content in N-methyl-N-vinylacetamide to 0.01-150 ppm. This method enables production of N-methyl-N-vinylacetamide having a stable quality, which can be controlled in stability and polymerizability as a monomer. N-methyl-N-vinylacetamide produced by such a method enables production of an N-methyl-N-vinylacetamide polymer having stable physical properties such as a molecular weight.

Description

technical field [0001] The present invention relates to a polymerization inhibitor for improving the stability and / or polymerizability of N-methyl-N-vinylacetamide, and N- A method for producing methyl-N-vinylacetamide, and a polymer obtained by polymerizing N-methyl-N-vinylacetamide obtained by the production method. [0002] More specifically, the present invention relates to N-1,3-butadienyl-N-methyl that will inhibit and stabilize N-methyl-N-vinylacetamide and control its polymerizability A method for producing N-methyl-N-vinylacetamide in which the content of acetamide is controlled within a specific range and whose stability and / or polymerizability are improved, and N-methyl-N-vinylacetamide obtained by the production method Homopolymers formed by amide polymerization and copolymers formed by copolymerization with other monomers, the N-methyl-N-vinylacetamide is used in contact lenses, tackifiers for oil excavation, gas hydrate inhibition N-methyl-N-ethylene for agents...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C231/22C07C233/05C08F26/02
CPCC07C231/08C07C231/22C07C231/24C08F126/02C07C233/05C08F226/02
Inventor 石井彻弥
Owner RESONAC HOLDINGS CORPORATION
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