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

A separation method and technology for acrylic acid, applied in the chemical industry, can solve the problems of increased loss of hydroxyhexyl acrylate, low yield of hydroxyhexyl acrylate, inability to realize separation, etc., and achieve the effects of improving separation effect, good extraction effect and effective separation

Active Publication Date: 2020-06-19
WANHUA CHEM GRP CO LTD
View PDF6 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the reaction solution of acrylate-6-hydroxyhexyl ester, mainly comprise excessive 1,6-hexanediol, by-product 1,6-hexanediol diacrylate and product acrylate-6-hydroxyhexyl ester, yet from 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, make product hydroxyhexyl acrylate loss increase, yield is lower; 1,6-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 through conventional vacuum distillation, and long-term high temperature may make 1,6 -Hexanediol diacrylate is polymerized and cross-linked, resulting in a further increase in impurities in the product -6-hydroxyhexyl acrylate, resulting in a lower yield and lower purity of the product hydroxyhexyl acrylate

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation and separation method of acrylic acid-6-hydroxyhexyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] The preparation and separation method of the 6-hydroxyhexyl acrylate of the present embodiment comprises the following steps:

[0043] (1) Put 106.2kg of 1,6-hexanediol, 36kg of acrylic acid, 0.36kg of copper N,N-dibutyldithiocarbamate and 0.72kg of p-toluenesulfonic acid into a 250L reactor, stir and heat up to 105°C for reaction 1.5h, the reaction solution was obtained. Among them, the reaction solution mainly includes the following main components: 47.6wt% of 1,6-hexanediol, 42.2wt% of 6-hydroxyhexyl acrylate, 6.3wt% of 1,6-hexanediol diacrylate, The selectivity of 6-hydroxyhexyl acrylate was 82.8%, and the conversion rate was 78.1%.

[0044] (2) Add water to the reaction solution obtained in step (1) to form water phase A, the mass ratio of water to the reaction solution is 1: 2.75; use cyclohexane as the extraction agent, and remove the reaction by 9 stages of continuous countercurrent centrifugal extraction 1,6-hexanediol diacrylate in the liquid; during the ext...

Embodiment 2

[0049] The preparation and separation method of the 6-hydroxyhexyl acrylate of the present embodiment comprises the following steps:

[0050] (1) Put 129.8kg of 1,6-hexanediol, 36kg of acrylic acid, 0.54kg of copper N,N-dibutyldithiocarbamate, and 1.26kg of phosphoric acid into a 250L reactor, stir and heat up to 110°C for 0.5h, get the reaction solution. Among them, the reaction solution mainly includes the following main components: 48.6 wt% of 1,6-hexanediol, 41.1 wt% of 6-hydroxyhexyl acrylate, and 5.2 wt% of 1,6-hexanediol diacrylate , the selectivity of acrylate-6-hydroxyhexyl ester was 84.2%, and the conversion rate was 79.3%.

[0051] (2) Add water to the reaction solution obtained in step (1) to form water phase A, the mass ratio of water to the reaction solution is 1: 3.25; use cyclohexane as the extraction agent, and remove the reaction solution through 11 stages of continuous countercurrent centrifugal extraction 1,6-hexanediol diacrylate; during the extraction p...

Embodiment 3

[0056] The preparation and separation method of the 6-hydroxyhexyl acrylate of the present embodiment comprises the following steps:

[0057] (1) Put 115kg of 1,6-hexanediol, 36kg of acrylic acid, 0.42kg of copper N,N-dibutyldithiocarbamate, and 1.1kg of methanesulfonic acid into a 250L reactor, stir and heat up to 108°C for 1 hour , to get the reaction solution. Among them, the reaction solution mainly includes the following main components: 47.9 wt% of 1,6-hexanediol, 41.6 wt% of 6-hydroxyhexyl acrylate, and 5.8 wt% of 1,6-hexanediol diacrylate , the selectivity of acrylate-6-hydroxyhexyl ester was 83.2%, and the conversion rate was 78.7%.

[0058] (2) Add water to the reaction solution obtained in step (1) to form water phase A, the mass ratio of water to the reaction solution is 1:3; use cyclohexane as the extraction agent, and remove the reaction by 10 stages of continuous countercurrent centrifugal extraction 1,6-hexanediol diacrylate in the liquid; during the extracti...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention provides a preparation and separation method of acrylic acid-6-hydroxyhexyl ester, which comprises the following steps: mixing acrylic acid, 1, 6-hexanediol, a copper salt polymerizationinhibitor and a catalyst, and heating to 105-110 DEG C for reaction to obtain a reaction solution containing acrylic acid-6-hydroxyhexyl acrylate, 1, 6-hexanediol and 1, 6-hexanediol diacrylate; adding water into the reaction liquid to form a water phase A, and carrying out extraction by taking aliphatic alkane as an extracting agent to obtain a water phase B; carrying out reduced pressure distillation on the water phase B to obtain a mixture containing 1, 6-hexanediol and acrylic acid-6-hydroxyhexyl ester; and feeding the mixture from the bottom of a rectifying tower, feeding the mixture ofionic liquid and the copper salt polymerization inhibitor from a tower plate at the upper part of the rectifying tower, and distilling the tower bottom liquid in a short-path evaporator to obtain theacrylic acid-6-hydroxyhexyl ester product. According to the method, the acrylic acid-6-hydroxyhexyl ester with the yield of 94%-96% and the purity of more than 99% can be obtained.

Description

technical field [0001] The invention belongs to the field of chemical industry, 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 compared with 4-Hydroxybutyl Acrylate (4-HBA). Compared with 4-HBA, it has the following advantages: (1) the carbon chain of -6-hydroxyhexyl acrylate is longer, and the viscosity of resin can be further reduced by using it to prepare resin, thereby obtaining high-solid and low-viscosity products; (2) realizing It achieves a better balance between hardness and softness, and solves the problem of traditional acrylates; (3) the chain segment connected to the hydroxyl group has greater flexibility, which reduces the steric hindrance of the alcoholic hydroxyl group, and because the hydroxyl group has more The large activity and higher r...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
IPC IPC(8): C07C67/08C07C67/48C07C67/54C07C67/58C07C69/54
CPCC07C67/08C07C67/48C07C67/54C07C67/58C07C69/54
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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap