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Environment-friendly preparation method of alpha-cyanoacrylate compound

A technology of cyanoacrylate and cyanoacrylic acid, which is applied in the field of environmentally friendly preparation of α-cyanoacrylate compounds, can solve the problems of easily affecting the health of production personnel, reducing biological safety, and contacting personnel injuries, etc., to achieve reduction Contamination and operator injury, improvement of biological safety, and reduction of difficulty

Active Publication Date: 2012-11-14
BEIJING COMPONT MEDICAL DEVICES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The disadvantages of this preparation method are obvious. On the one hand, the application of toxic solvents is likely to cause environmental pollution, and it is also easy to affect the health of production personnel. , plasticizers and polymerization inhibitors, etc., so in the final product, it is unavoidable that there will be a small amount of residues. These residual toxic solvents, polymerization inhibitors and plasticizers will cause great harm to the contact personnel, greatly Reduced biosafety in clinical application

Method used

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  • Environment-friendly preparation method of alpha-cyanoacrylate compound
  • Environment-friendly preparation method of alpha-cyanoacrylate compound
  • Environment-friendly preparation method of alpha-cyanoacrylate compound

Examples

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preparation example Construction

[0031] The present invention provides an environmentally friendly preparation method of α-cyanoacrylate compounds with less environmental pollution, less harm to production personnel and high biological safety. The three-step method comprises the following steps:

[0032] 1) Formaldehyde solution and composite catalyst A are added in a low-toxicity solvent, and a mixture of α-cyanoacetate compounds and catalyst B is added dropwise under stirring to generate prepolymers and oligomers of α-cyanoacrylate compounds. mixture;

[0033] 2) Add dilute acid solution, stir for a period of time and separate the liquid, remove the water layer, so that the remaining catalyst in the prepolymer and oligomer mixture of α-cyanoacrylate can be removed, and then add plasticizer and dehydrating agent and a polymerization inhibitor, heated to remove water, distilled at high temperature to depolymerize the prepolymer or oligomer to obtain the crude product of α-cyanoacrylic acid compound;

[0034]...

Embodiment 1

[0055] Embodiment 1, formaldehyde aqueous solution method prepares n-butyl α-cyanoacrylate

[0056] Prepare α-n-butyl cyanoacrylate with the method of the present invention, formula is shown in Table 1, specifically comprises the following steps:

[0057] 1) In a 2000mL four-neck flask, add 224g 37% formaldehyde solution, 200g methyl carbonate, 4.5g composite catalyst A, stir evenly, heat to about 60°C (50-75°C is acceptable), add dropwise 400g α-cyanide The mixture of butyl acetate and 1.0g piperidine, after the dropwise addition, continue to heat and keep the reaction under reflux state and temperature 50-85°C for 1.5-2 hours to obtain the prepolymer or oligomer of n-butyl cyanoacrylate thing.

[0058]2) stop heating, add 50g dilute hydrochloric acid, leave standstill layering after stirring evenly, after removing supernatant, add 200g acetyl tributyl citrate, assemble water separator on the right side port of four-neck flask, be warming up to 80 At about ℃, reflux begins ...

Embodiment 2

[0062] Embodiment 2, paraformaldehyde method prepares n-butyl α-cyanoacrylate

[0063] Using the same operation as in Example 1, using the materials and amounts listed in Table 1, step 2) collected about 350 g of crude product, and step 3) obtained about 245 g of refined monomer, with a yield of 55.5%. Product testing results: gas chromatography purity of 99.6%, 1 H-NMR (600MHz, CDCl 3 , δ / ppm): 6.99(s, 1H), 6.61(s, 1H), 4.04(t, 2H), 1.73(m, 2H), 1.51(m, 2H), 0.95(t, 3H), confirmation sheet The body is n-butyl α-cyanoacrylate.

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Abstract

The invention discloses a preparation method of the alpha-cyanoacrylate compound, comprising the following steps: (1) subjecting the mixture of the alpha-cyanoacrylate compound and a catalyst B to reaction with formaldehyde in a low-toxicity solvent under the existence of a catalyst A to generate the mixture of a prepolymer and an oligomer; (2) removing the catalyst in the mixture of the prepolymer and the oligomer, and adding a plasticizer and a polymerization inhibitor to subject the prepared mixture of reaction to depolymerization reaction to generate a crude product; and (3) rectifying the crude product to obtain the alpha-cyanoacrylate compound with high purity. The reaction is carried out in the solvent with low toxicity under the existence of the special catalyst, and the plasticizer and the polymerization inhibitor with high boiling point and less toxicity are adopted, thus the final product has the advantages of less toxicity and low biohazard, and the biological safety of the medical adhesive product of the alpha-cyanoacrylate compound is improved greatly when being used clinically.

Description

technical field [0001] The invention relates to a compound preparation method in the field of chemical synthesis, in particular to an environmentally friendly preparation method of α-cyanoacrylate compounds. Background technique [0002] The chemical structural formula of α-cyanoacrylate compounds is shown in formula I: [0003] [0004] R may be a linear, branched, or cyclic alkyl group having 1-20 combined carbon atoms; alternatively, R may be of the formula R 2 -O-R 3 group, where R 2 and R 3 are independently linear, branched or cyclic alkyl groups with 1-20 combined carbon atoms; or, R can be of the formula R 4 -COO-R 5 group, where R 4 and R 5 are independently linear, branched or cyclic alkyl groups having 1-20 combined carbon atoms. [0005] The use of α-cyanoacrylate compounds as adhesives has the characteristics of single component, easy to use, fast curing at room temperature, and high bonding strength. Therefore, it is widely used in many fields, such ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/23C07C253/30C07C253/32
Inventor 沈伟
Owner BEIJING COMPONT MEDICAL DEVICES
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