Method for preparing alpha-aminonitrile and product and application thereof

A technology of amino nitrile and amino group, applied in the field of preparing α-amino nitrile, can solve the problems of toxicity and cost that cannot be ignored, increased production cost and high preparation cost, and achieves the effects of low toxicity, short reaction time and high reactivity

Active Publication Date: 2021-02-23
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows us to make small molecules called alpha -nitrogen imides (α-NIT) with fewer chemical substances than previously used by other methods such as hydrolysis or condensation techniques that were developed earlier. It can be done at room temperature without adding any extra materials like pigments or dyes. Additionally, this process produces less harmful waste products when producing these types of compound.

Problems solved by technology

This patented technical problem addressed by this patent relates to finding a safer way to prepare alpha -aminitrile without use expensive precious metallic catalysis agents like platinum (Pt) that could cause harmful effects on human health.

Method used

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  • Method for preparing alpha-aminonitrile and product and application thereof
  • Method for preparing alpha-aminonitrile and product and application thereof
  • Method for preparing alpha-aminonitrile and product and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1 (do not add alkali)

[0041] Synthetic method: Add 2mmol of tertiary amine 1 into a 100mL reaction flask, then add 2mmol of benzoylnitrile and 40mL of acetonitrile, vacuumize the reaction device and pass in argon, and magnetically Stir the reaction. The reaction vial was placed at a distance of 1 cm from an 18W purple light with a wavelength of 390-400nm, and the reaction was continued for 24 hours. After the reaction was completed, silica gel was used for adsorption and the solvent was spin-dried in vacuum. The eluent was petroleum ether / ethyl acetate system (volume ratio: 20:1). The results are shown in Table 1. The reaction formula is as follows:

[0042]

[0043] Table 1

[0044]

[0045]

Embodiment 2-6

[0046] Embodiment 2-6 (different light sources)

[0047] Synthesis method: 2mmol of tertiary amine 1 is added to a 100mL reaction flask, then 3mmol of benzoyl nitrile, 2mmol of lithium carbonate or other bases such as those in Table 2, and 40mL of acetonitrile are added, the reaction device is evacuated and Argon gas was introduced, and the reaction was magnetically stirred at room temperature under the protection of argon gas. Place the reaction bottle at a distance of 1cm from 18W 365-375nm ultraviolet light source, 380-390nm purple light source, 400-415nm purple light source, 450-465nm blue light source or 510-520nm green light source, and continue to react for 24 hours. After the reaction was completed, silica gel was used for adsorption and the solvent was spin-dried in vacuum. The eluent was petroleum ether / ethyl acetate system (volume ratio: 20:1). The results are shown in Table 2. The reaction formula is as follows:

[0048]

[0049] Table 2

[0050]

Embodiment 7-27

[0052]Synthesis method: Add 2mmol of tertiary amine 1 into a 100mL reaction flask, then add 3mmol of benzoyl nitrile, 2mmol of lithium carbonate, and 40mL of acetonitrile, vacuumize the reaction device and pass it into argon, Under protective conditions, the reaction was stirred magnetically at room temperature. The reaction vial was placed at a distance of 1 cm from an 18W purple light with a wavelength of 390-400nm, and the reaction was continued for 24 hours. After the reaction was completed, silica gel was used for adsorption and the solvent was spin-dried in vacuum. The eluent was petroleum ether / ethyl acetate system (volume ratio 10-40:1). The results are shown in Table 3. The reaction formula is as follows:

[0053]

[0054] table 3

[0055]

[0056]

[0057]

[0058]

[0059]

[0060]

[0061] In the above examples, lithium carbonate is replaced by 2,6-lutidine, pyridine, 1,8-diazabicycloundec-7-ene, N-methylmorpholine, Hans ester, phosphoric aci...

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Abstract

The invention discloses a method for preparing alpha-aminonitrile, which comprises the following steps: by using tertiary amine and benzoyl cyanide as reactants, carrying out visible light irradiationin an organic solvent under the condition of oxygen or inert gas, and reacting at room temperature to obtain alpha-aminonitrile. The invention also discloses alpha amino nitrile and an application thereof. Visible light irradiation is used for promoting tertiary amine and benzoyl nitrile to react to prepare alpha-amino nitrile, a photocatalyst and a metal catalyst do not need to be additionally added, even alkali does not need to be added in some reactions, the reaction activity is high, the reaction conditions are mild, the reaction time is short, and the target product yield is high. According to the method, benzoyl nitrile is used as a cyanation reagent, so that the toxicity is low, the cost is low, and the industrial production of alpha-aminonitrile is facilitated.

Description

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Claims

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Application Information

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Owner NANJING AGRICULTURAL UNIVERSITY
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