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α-Hydroxymethyl acrylate compounds and production method thereof

A technology of methyl hydroxymethyl acrylate and a manufacturing method, applied in the field of α-hydroxymethyl acrylate compounds and their manufacture, can solve the problems such as the inability to fully remove formaldehyde, and achieve the effect of preventing pollution

Active Publication Date: 2015-08-05
NIPPON SHOKUBAI CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it is substantially the same as the above-mentioned prior art, and formaldehyde cannot be sufficiently removed by such an aqueous solution cleaning and distillation operation.

Method used

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  • α-Hydroxymethyl acrylate compounds and production method thereof
  • α-Hydroxymethyl acrylate compounds and production method thereof
  • α-Hydroxymethyl acrylate compounds and production method thereof

Examples

Experimental program
Comparison scheme
Effect test

Synthetic example 1

[0168] (Synthesis example 1 (synthesis of crude RHMAs))

[0169] 2066 g (24 moles) of methyl acrylate as an acrylate, 195.8 g (6 moles in terms of formaldehyde) as formaldehyde were added to a 3-L four-neck flask equipped with a thermometer, a gas blowing pipe, a cooling pipe, a stirring device, and a water bath. 92% by mass of paraformaldehyde as a raw material, 237.8 g (1.2 mol) of a 30% by mass trimethylamine aqueous solution as a catalyst, and 2.1 g of p-methoxyphenol as a polymerization inhibitor. The ratio of p-methoxyphenol to methyl acrylate was 1000 ppm. Thereafter, while blowing air into the reaction solution, the reaction solution was stirred at 70° C. for 8 hours to perform a reaction.

[0170]After the reaction, the reaction solution was transferred to a separatory funnel and separated into an organic phase and an aqueous phase. Then, 100 g of water was added to the organic phase for water washing. After being separated into an organic phase and an aqueous phas...

Embodiment 1

[0173] Transfer 600 g of the crude RHMA obtained in Synthesis Example 1 into a four-neck flask with a capacity of 2 L equipped with a thermometer, a gas blowing tube, an empty column distillation tube, a stirring device, and an oil bath, and keep the internal temperature at 110 to 120° C. while blowing in air. , The condition of pressure 20hPa (15mmHg) was refluxed for 10 hours. The liquid distilled at this time was cooled at 10 degrees by a condenser and returned to the flask, and the gas component containing formaldehyde was discharged into the vacuum system.

[0174] The cumulative steam amount at this time was 801 g, the total reflux ratio was 1.3, and the formaldehyde concentration in the obtained crude RHMAs was 320 ppm.

[0175] The crude RHMAs obtained by the above-mentioned method were subjected to fractional distillation by the method described in Comparative Example 1 described later to obtain 407 g of RHMA-M having a formaldehyde concentration of 20 ppm. The resul...

Embodiment 2～5

[0177] In Example 1, the reflux time was changed to 8 hours (Example 2), 6 hours (Example 3), 5 hours (Example 4) or 4 hours (Example 5), and the polymerization inhibitor was changed to two Copper butyldithiocarbamate (Example 2), 2,2,6,6-Tetramethylpiperidinyl radical (TEMPO) (Example 3), except that RHMA was obtained in the same manner as in Example 1 -M. Table 1 shows the results of total reflux ratio, crude RHMAs and formaldehyde concentration in purified RHMA-M.

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Abstract

It is intended to provide RHMA compounds, by which only a small amount of formaldehyde employed as a starting material remains in the final products and which are substantially not colored, and a method of practically producing the same. A method of producing an a-hydroxymethyl acrylate compound which involves the step of reacting an acrylic acid ester with formaldehyde in the presence of a catalyst, wherein the production method comprises the purification step of vaporizing a crude product obtained from the reaction step under reduced pressure and flowing back substantially all of the liquefied product, and the formaldehyde content is regulated to less than 200 ppm.

Description

technical field [0001] The present invention relates to α-hydroxymethyl acrylate compounds and their production methods. More specifically, the present invention relates to α-hydroxymethacrylate compounds having a low formaldehyde content, which are useful as raw materials for chemicals and pharmaceuticals, and a method for producing the same. Background technique [0002] For hydroxyl-containing vinyl compounds, the double bond site is rich in chemical reactivity such as addition reaction and polymerization reaction, and also has the reactivity of hydroxyl group. α-Hydroxymethylacrylate compounds, which represent hydroxyl-containing vinyl compounds, are expected to be used as monomers for forming polymers; various chemicals such as paints, adhesives, detergent builders, and transparent resins It is used in a wide range of fields such as raw materials for manufacturing products, intermediates of pharmaceuticals such as anticancer agents and antiviral agents, and is expected...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/732C07C67/31C07B61/00
CPCC07C67/343
Inventor 稻垣贵大长野英明佐藤裕一
Owner NIPPON SHOKUBAI CO LTD
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