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Preparation method of environment-friendly type alpha-cyanoacrylate

A technology of cyanoacrylate and cyanoacetate is applied in the field of preparation of α-cyanoacrylate, can solve the problems of environmental pollution, can not meet, can not meet environmental protection requirements, etc., and achieves the effect of high yield

Inactive Publication Date: 2015-03-11
SHANDONG YUWANG IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this preparation process is that, on the one hand, such organic solvents and additives are likely to pollute the environment, and on the other hand, they also have certain damage to the health of production personnel.
The products produced according to the above process, while not meeting the requirements of environmental protection, can not meet the needs of some customers and markets, such as nail glue, etc.

Method used

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  • Preparation method of environment-friendly type alpha-cyanoacrylate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Applied to the preparation of ethyl α-cyanoacrylate

[0035] Add ethyl cyanoacetate and toluene into a 1000ml three-necked flask, and when the temperature rises to 60°C, add a mixture of hexahydropyridine and formaldehyde solution. After the dropwise addition, heat and keep warm, and keep reflux at 60°C for 1 hour. Then carry out azeotropic dehydration for 2 hours, then add tributyl citrate, phosphorus pentoxide, p-hydroxyanisole, etc., and crack at a temperature of 170°C and a vacuum of 1 mmHg to obtain the crude monomer of ethyl α-cyanoacrylate , after rectification, the refined monomer of α-ethyl cyanoacrylate with a purity of 99.9% can be obtained, and the calculated yield is 80%.

[0036] Wherein, the feeding molar ratio of ethyl cyanoacetate and formaldehyde aqueous solution is 1.00:1, and the input amount of toluene is 100ml / mol formaldehyde, and the input amount of hexahydropyridine is 0.2ml / mol formaldehyde, and the input amount of tributyl citrate is 5g / mol. ...

Embodiment 2

[0039] Applied to the preparation of methoxyethyl α-cyanoacrylate

[0040] Add paraformaldehyde and dichloropropane into a 1000ml three-necked flask. When the temperature rises to 60°C, add a mixture of sodium hydroxide and methoxyethyl cyanoacetate. After the dropwise addition, heat and keep it warm. Keep reflux at -90°C for 1.5h, carry out azeotropic dehydration for 3h, then add synthetic vegetable esters, phosphorus pentoxide, 2,5-di-tert-butylhydroquinone, etc., and crack at 200°C and 10mmHg vacuum , to obtain the crude monomer of methoxyethyl α-cyanoacrylate, after rectification, the refined monomer of α-ethyl cyanoacrylate with a purity of 99.9% can be obtained, and the calculated yield is 75%.

[0041] Wherein, the molar ratio of methoxyethyl cyanoacetate and paraformaldehyde is 1.04:1, the input amount of dichloropropane is 200ml / mol paraformaldehyde, and the input amount of sodium hydroxide is 0.6ml / mol paraformaldehyde, The input amount of synthetic vegetable ester ...

Embodiment 3

[0043] Applied to the preparation of n-butyl α-cyanoacrylate

[0044]Add formaldehyde aqueous solution and dimethyl carbonate into a 1000ml three-necked flask. When the temperature rises to 65°C, add the mixture of potassium hydroxide and n-butyl cyanoacetate. After the dropwise addition, heat and keep warm. Keep reflux for 3 hours, carry out azeotropic dehydration for 3.5 hours, then add epoxidized soybean oil, phosphorus pentoxide, butyl hydroxyanisole, etc., and crack at 190°C and 5mmHg vacuum to obtain n-butyl α-cyanoacrylate The crude monomer, after rectification, can obtain the refined monomer of α-n-butyl cyanoacrylate with a purity of 99.9%, and the yield is 70%.

[0045] Wherein, the molar ratio of n-butyl cyanoacetate and formaldehyde aqueous solution is 1.02:1, the input amount of dimethyl carbonate is 100ml / mol formaldehyde, the input amount of potassium hydroxide is 0.4ml / mol formaldehyde, the input amount of epoxy soybean oil Formaldehyde is 15g / mol, the input a...

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Abstract

The invention discloses a preparation method of environment-friendly type alpha-cyanoacrylate, which takes cyanoacetates and formaldehyde or paraformaldehyde as raw materials, under existence of a basic catalyst, an organic solvent which enables azeotropy with water can be taken as a dehydrant, then a condensation reaction is carried out, after completely dehydrating, an environment-friendly type plasticizer, an anionic polymerization inhibitor and an environment-friendly type free radical polymerization inhibitor are added for cracking, and then are rectified to obtain the alpha-cyanoacrylate monomer. The preparation method of the present invention selects the organic solvent for azeotropy and dehydration, the environmental protection plasticizer and the polymerization inhibitor are employed during the cracking process, then the environment-friendly type alpha-cyanoacrylate can be obtained with high yield, and the preparation method is suitable for field with high requirement on environmental protection.

Description

technical field [0001] The invention relates to the field of adhesives, more precisely, to a preparation method of α-cyanoacrylate. Background technique [0002] α-cyanoacrylate compounds, due to their high anionic polymerization characteristics, polymerize and solidify when exposed to water, thereby producing a certain adhesive force on the surface of the bonding material, which can be used for steel, non-ferrous metals, rubber, leather, plastics, ceramics , glass, wood, etc. [0003] At present, the main preparation process of α-cyanoacrylate is: in an organic solvent, cyanoacetate and formaldehyde or paraformaldehyde are carried out in the presence of a basic catalyst for condensation polymerization, and then the water is separated by a dehydrating agent. Removal, then add a certain amount of plasticizer and polymerization inhibitor, through high temperature cracking, to obtain the crude monomer of α-cyanoacrylate, and finally obtain the corresponding monomer through rec...

Claims

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Application Information

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IPC IPC(8): C07C255/23C07C253/30C07C253/34
Inventor 刘汝萃王彩华李晶倪洪凯王淑敏张娟娟
Owner SHANDONG YUWANG IND