The synthetic method of n-octyl α-cyanoacrylate

A technology of cyanoacrylic acid and synthesis method, which is applied in chemical instruments and methods, preparation of carboxylic acid nitrile, preparation of organic compounds, etc., can solve the problems of great harm to human body, operator injury, methanol residue, etc., and improve the reaction rate of raw materials. , The effect of reducing side reactions and no methanol residue

Active Publication Date: 2021-09-17
GUANGZHOU BAIYUN MEDICAL ADHESIVE CO LTD
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

The traditional process of preparing n-octyl α-cyanoacrylate requires the preparation of methanol solution of formaldehyde as a synthetic raw material, which increases the operation steps, and the methanol solution of formaldehyde is volatile, has a strong pungent smell, and is harmful to the human body. It is easy to cause harm to the operator during the feeding stage of the synthesis reaction, and there may be residual methanol in the finished product, which increases the difficulty of product quality inspection. reduce

Method used

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Examples

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preparation example Construction

[0029] The present invention provides a synthetic method of n-octyl α-cyanoacrylate of one embodiment, comprising the following steps:

[0030] S1. Using paraformaldehyde and n-octyl cyanoacetate as raw materials and petroleum ether as the reaction medium, under the catalysis of a basic catalyst, carry out condensation reaction at 78 ° C to 84 ° C to obtain n-octyl α-cyanoacrylic acid Reaction mixture of ester polymer.

[0031] In one embodiment, the basic catalyst is preferably at least one selected from pyridine catalysts and amine catalysts.

[0032] Specifically, pyridine catalysts include pyridine, lutidine, and piperidine, etc.; amine catalysts include N-ethylmorpholine, triethylenediamine, triethanolamine, and the like.

[0033] Preferably, the catalyst is piperidine.

[0034] In one embodiment, the condensation reaction is a reflux condensation reaction, the temperature of the condensation reaction is 78°C-84°C, and the reaction time is 7h-8h.

[0035] In one embodi...

Embodiment 1

[0057] Add 90g of paraformaldehyde solid powder, 1.5mL of piperidine, and 500mL of petroleum ether (boiling range is 60°C to 90° C.), 650 g of n-octyl cyanoacetate, and reflux at 78° C. to 84° C. for 7.5 hours to obtain a reaction mixture containing n-octyl cyanoacrylate polymer. Continue to raise the temperature, recover petroleum ether until the temperature of the reaction mixture reaches 115° C., quickly add 20 g of phosphorus pentoxide and 1.5 g of hydroquinone, and stir thoroughly. Remove the stirring device and replace it with a vacuum distillation device. While slowly vacuuming, raise the temperature to remove residual petroleum ether. When the temperature reaches 130 ° C and the vacuum degree is less than 300 Pa, replace the receiving bottle with 0.1 g A two-necked flask containing hydroquinone and 0.3 g of phosphorus pentoxide collected the crude n-octyl α-cyanoacrylate crude monomer that was cracked when the vacuum degree was within 230 Pa and the temperature was 160...

Embodiment 2

[0059] Embodiment 2 is basically the same as Example 1, except that the consumption of n-octyl cyanoacetate is different, specifically: the consumption of n-octyl cyanoacetate in embodiment 2 is 600g. The raw material reaction rate is 95.6%, the product yield is 60.2%, and the product purity is 98.7% through gas chromatography detection.

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Abstract

The invention relates to a method for synthesizing n-octyl α-cyanoacrylate, comprising the following steps: taking paraformaldehyde and n-octyl cyanoacetate as raw materials and petroleum ether as a reaction medium; Condensation reaction at ~84°C to obtain a reaction mixture containing n-octyl α-cyanoacrylate polymer; after the reaction is completed, recover the petroleum ether in the reaction mixture, then add a polymerization inhibitor, and carry out cracking and distillation under reduced pressure to obtain α-n-octyl cyanoacrylate crude monomer; the crude n-octyl cyanoacrylate monomer is purified to obtain fine n-octyl cyanoacrylate. The method has high reaction efficiency, high product yield, strong safety and less harm to operators.

Description

technical field [0001] The invention relates to the technical field of medical adhesives, in particular to a method for synthesizing n-octyl alpha-cyanoacrylate. Background technique [0002] Since the United States first introduced the world's first α-cyanoacrylate fast adhesive (α-glue for short) for bonding skin and hemostasis in 1958, adhesives based on α-cyanoacrylate have developed rapidly. . Because it has the following advantages: 1. Single component, solvent-free, and no curing agent; 2. Physical properties compatible with natural tissues; 3. Stable chemical properties without degrading harmful substances; 4. Good biocompatibility Non-toxic, non-carcinogenic, non-teratogenic, non-mutagenic, non-hemolytic, non-pyrogenic, non-cytotoxic, non-sensitizing, non-irritating, non-carcinogenic, itself sterile, and has the advantages of forming a bacteriostatic zone against eleven kinds of bacteria, etc. , which has aroused great interest in the medical field and has been wi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/23C07C253/30C07C253/34
CPCC07C253/30C07C253/34C07C255/23
Inventor 杜宇聪谢剑波曾仑史志伟欧达欣
Owner GUANGZHOU BAIYUN MEDICAL ADHESIVE CO LTD
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