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Synthesis method of cyanoacrylate compound

A technology of cyanoacrylate and synthesis method, which is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as production capacity limitation, potential risks to human health and environment, and improve production efficiency. , the effect of eliminating human health hazards and ecological environment pollution, and improving the utilization rate of equipment

Pending Publication Date: 2021-09-17
上海泰初化工技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0038] Although the technical solution of method seven has certain advantages, the synthesis method used in method seven is carried out in organic solvents, and general organic solvents have potential risks to human health and the environment, and the production capacity will also be limited

Method used

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  • Synthesis method of cyanoacrylate compound
  • Synthesis method of cyanoacrylate compound
  • Synthesis method of cyanoacrylate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment -1

[0054] step one,

[0055] Reaction formula:

[0056]

[0057] Operation process: the synthesis of ethyl phenyl carbamidate is carried out with reference to the relevant content of the document J.hetercyclic.Chem.33. 1903 (1996). Operation process: at 5-10°C, 150g of hydrogen chloride gas is bubbled into a solution of about 4.0 moles of benzonitrile and 8.0 moles of ethanol in 2000 milliliters of toluene. And stirred at room temperature (25°C) for 20 hours, and the white solid was filtered off. This white solid was dissolved in 3000 milliliters of absolute ethanol and neutralized to a pH value of 7-8.5 with triethylamine, the solvent was evaporated to dryness under reduced pressure, triethylamine hydrochloride was filtered out, and the filter cake was washed 3 times with 200ml dichloromethane, and combined Dichloromethane and part of the ethanol were removed from the filtrate and washing liquid under reduced pressure, and the remaining oil was distilled under reduced press...

Embodiment 2

[0061] step one,

[0062] Reaction formula:

[0063]

[0064] Operation process: Add 121g (1.0mol) of benzamide, 169.4g (1.10mol) of diethyl sulfate, and 860g of toluene into a four-necked flask equipped with mechanical stirring, a thermometer, and a reflux condenser. Raise the temperature to 110-120°C for reflux reaction for 4 hours, then cool down to 25°C. Neutralize to pH 7.0-8.5 with 5% sodium hydroxide solution, separate the phases, and dry the organic layer with 25 g of anhydrous sodium sulfate. After removing toluene, vacuum distillation cut off the fraction at 104-105°C at 2 mmHg to obtain 130 g of ethyl benzimidate with a purity of 98% by GC analysis.

[0065] step two

[0066] Reaction formula:

[0067]

[0068] Operation process: Add 149g (1.0mol) of ethyl phenylcarboximidate, 113g of ethyl cyanoacetate (1.0mol), DMAP (4-di methylaminopyridine) 0.1g to 80°C, and reacted at this temperature for 2 hours, then raised to 100°C, and kept at this temperature fo...

Embodiment 3

[0070] step one

[0071] Reaction formula:

[0072]

[0073] Operation process: the synthesis of ethyl phenyl carbamidate is carried out with reference to the relevant content of the document J.hetercyclic.Chem.33. 1903 (1996). At 5-10° C., 150 g of hydrogen chloride gas is bubbled into a solution of about 4.0 moles of benzonitrile and 8.0 moles of ethanol in 2000 milliliters of toluene. And stirred at room temperature (25° C.) for 20 hours to obtain a white solid which was filtered out. Add 10% sodium carbonate solution to neutralize to a pH value of 7.0-8.5, separate phases, wash the organic layer with (1%) sodium bicarbonate three times, dry with 50g of anhydrous sodium sulfate, filter out sodium sulfate crystals, and store at 80°C, Toluene was removed under a vacuum of 0.98 to obtain 586 g of ethyl benzoate, (content 93%, quantitative analysis by gas chromatography)

[0074] step two

[0075]

[0076] Operation process: In a four-necked glass bottle equipped with...

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Abstract

The present invention discloses a cyanoacrylate synthesis method, which comprises the following reaction process: a compound (1) and a compound (2) react to directly prepare a compound (3), and is characterized in that the reaction is performed in a molten state, and since no solvent is used, the harm of the solvent to personnel and the natural environment is reduced, and the production efficiency is improved. Compound (1); a compound (2); and a compound (3).

Description

technical field [0001] The invention belongs to the field of compound synthesis, and in particular relates to a synthesis method of 2-cyano-3-aminoacrylate compounds. Background technique [0002] Cyanoacrylate compounds have important applications in the field of life sciences. Among them, 2-cyano-3-amino-3-phenylacrylate derivatives are used as pesticide fungicides to control wheat scab and rice bakanae. It has excellent control effect. [0003] The method for synthesizing 2-cyano-3-aminoacrylate mainly contains the following methods: [0004] Method 1 (J.Am.Chem.Soc..1943, 40, 388~390): [0005] It is prepared by condensation of amidine and cyanoacetate. The reaction between cyanoacetate and amidine produces two products, of which the yield of the target product is only 28%. The yield of the method is very low and it is difficult to purify. The reaction formula is as follows: [0006] [0007] y = 28% [0008] where R 2 for C 1 ~C 6 alkyl. [0009] Method 2 (Bu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C257/08C07C255/42C07C253/30C07D251/24C07C255/30C07D213/57A01P3/00
CPCC07C257/08C07C253/30C07D251/24C07D213/57C07C255/42C07C255/30
Inventor 谭昊明付其璋陈和粲刘雨阳其他发明人请求不公开姓名
Owner 上海泰初化工技术有限公司
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