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Preparation and separation method of acrylic acid-6-hydroxyhexyl ester

A separation method and acrylic acid technology are applied in the separation/purification of carboxylate, the preparation of carboxylate, the separation/purification of hydroxyl compounds, etc., and can solve the problems of low purity, increase in impurities, increase in loss of hydroxyacrylate, etc. High degree of automation, small size of equipment, and the effect of reducing difficulty

Active Publication Date: 2020-03-10
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] The reaction solution of acrylate-6-hydroxyhexyl mainly includes excess 1,6-hexanediol, by-product 1,6-hexanediol diacrylate and product acrylate-6-hydroxyhexyl, yet from the reaction solution It is difficult to isolate the product 6-hydroxyhexyl acrylate for the following reasons: On the one hand, due to the large excess of 1,6-hexanediol and its strong water solubility, the amount of water used in the process of removing 1,6-hexanediol by extraction Larger, so that the product acrylate hydroxy ester loss increases, the yield is lower; , 6-Hexanediol diacrylate contains two vinyl groups at both ends, and it is very easy to polymerize at high temperature. Therefore, the separation of the two cannot be achieved by conventional vacuum distillation, and the long-term high temperature may make 1,6- Polymerization and crosslinking of hexanediol diacrylate leads to further increase of impurities in the product 6-hydroxyhexyl acrylate, resulting in lower yield and lower purity of the product hydroxy acrylate

Method used

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  • Preparation and separation method of acrylic acid-6-hydroxyhexyl ester

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Experimental program
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Effect test

Embodiment 1

[0051] The preparation and separation method of present embodiment acrylate-6-hydroxyhexyl ester comprises the following steps:

[0052] (1) Put 118kg of 1,6-hexanediol, 36kg of acrylic acid, 0.6kg of phenothiazine and 0.81kg of methanesulfonic acid into a 250L reactor, stir and heat up to react, control the temperature of the reactor at 105°C, and keep it warm for 1.5h After cooling down, the reaction solution of 6-hydroxyhexyl acrylate was obtained. Among them, the selectivity of 6-hydroxyhexyl acrylate is 81.8%, and the conversion rate is 77.6%. %, 1,6-hexanediol diacrylate 6.1wt%.

[0053] (2) The reaction solution was poured into the frozen crystallizer through a centrifugal pump, the initial temperature was controlled at 25° C., the stirring speed was 100 rpm, the amount of 1,6-hexanediol seed crystal added was 1 wt % of the reaction solution, and the mixture was stirred at constant temperature for 30 minutes. Set the temperature program to lower the temperature, the c...

Embodiment 2

[0059] The preparation and separation method of present embodiment acrylate-6-hydroxyhexyl ester comprises the following steps:

[0060] (1) Put 129.8kg of 1,6-hexanediol, 36kg of acrylic acid, 0.4kg of p-hydroxyanisole, and 0.8kg of p-toluenesulfonic acid into a 250L reactor. Stir and heat up to react, control the temperature of the reactor to 110° C., keep the reaction for 1 hour, then cool down to obtain a reaction solution of 6-hydroxyhexyl acrylate. Among them, the selectivity of 6-hydroxyhexyl acrylate is 83.2%, and the conversion rate is 80.3%. %, 1,6-hexanediol diacrylate 5.4wt%.

[0061] (2) The reaction solution was poured into the frozen crystallizer through a centrifugal pump, the initial temperature was controlled at 25° C., the stirring speed was 100 rpm, the amount of 1,6-hexanediol seed crystals added was 2 wt % of the reaction solution, and the mixture was stirred at constant temperature for 30 minutes. Set the temperature program to cool down, the cooling r...

Embodiment 3

[0067] The preparation and separation method of present embodiment acrylate-6-hydroxyhexyl ester comprises the following steps:

[0068] (1) Put 79.6kg of 1,6-hexanediol, 27kg of acrylic acid, 0.5kg of copper N,N-dibutyldithiocarbamate, and 0.9kg of p-toluenesulfonic acid into a 250L reactor. Stir and heat up to react, control the temperature of the reactor to 110°C, keep the reaction for 0.5h, then cool down to obtain a reaction liquid of 6-hydroxyhexyl acrylate. Among them, the selectivity of 6-hydroxyhexyl acrylate is 78.6%, and the conversion rate is 75.3%. %, 1,6-hexanediol diacrylate 7.8wt%.

[0069] (2) The reaction solution was poured into the frozen crystallizer through a centrifugal pump, the initial temperature was controlled at 30°C, the stirring speed was 300 rpm, the amount of 1,6-hexanediol seed crystals added was 1.2wt% of the reaction solution, and the mixture was stirred at constant temperature for 30 minutes. Set the temperature program to cool down, the c...

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Abstract

The invention provides a preparation and separation method of acrylic acid-6-hydroxyhexyl ester. The method comprises the following steps: respectively adding acrylic acid, 1, 6-hexanediol, a polymerization inhibitor and a catalyst into a reaction container, stirring, heating to 105-110 DEG C, and reacting for 0.5-1.5 hours to obtain an acrylate-6-hydroxyhexyl ester reaction solution; adding 1, 6-hexanediol seed crystals into the acrylic acid-6-hydroxyhexyl ester reaction solution, then carrying out programmed cooling to separate out 1, 6-hexanediol crystals in the acrylic acid-6-hydroxyhexylester reaction solution, and filtering to obtain a filtrate and a filter cake; and carrying out extraction and reduced pressure distillation on the filtrate to obtain refined acrylic acid-6-hydroxyhexyl ester. The acrylic acid-6-hydroxyhexyl ester disclosed by the invention is relatively high in yield and relatively high in purity.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a preparation and separation method of 6-hydroxyhexyl acrylate. Background technique [0002] 6-Hydroxyhexyl acrylate belongs to new hydroxy acrylates, and the market for this product is blank at present. 6-Hydroxyhexyl acrylate is mainly against 4-Hydroxybutyl acrylate (4-HBA). Compared with 4-HBA, it has the following advantages: (1) The carbon chain of 6-Hydroxyhexyl acrylate is longer, Using it to prepare resin can further reduce the viscosity of the resin, so as to obtain high-solid and low-viscosity products; (2) achieve a good balance between hardness and softness, and solve the problem of traditional acrylates; (3) its hydroxyl-linked The chain segment has greater flexibility, which reduces the steric hindrance of the alcoholic hydroxyl group, and because the hydroxyl group has greater activity and higher reactivity, the curing speed of the synthesized hydrox...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/08C07C67/48C07C67/58C07C69/653C07C29/78C07C31/20
CPCC07C67/08C07C67/48C07C67/58C07C29/78C07C69/653C07C31/20
Inventor 陆国太黎源秦承群鞠昌迅郭华郑京涛胡展康学青胡爽李晶赵文娟王勤隆李文滨方璞
Owner WANHUA CHEM GRP CO LTD