Method for preparing adrenochrome by catalytic oxidation using nitrogen-doped carbon nanotubes

Patent metadata

Field	Value
Publication number	US-11420939-B2
Application number	US-202016828038-A
Country	US
Kind code	B2
Filing date	Mar 24, 2020
Priority date	Feb 18, 2020
Publication date	Aug 23, 2022
Grant date	Aug 23, 2022

Abstract

Disclosed is a method for preparing adrenochrome by catalytic oxidation using nitrogen-doped carbon nanotubes. The method catalyzes dissolved oxygen in an aqueous solution by the nitrogen-doped carbon nanotubes to rapidly oxidize adrenaline, which is completely transformed into adrenochrome. It is a novel preparation process of adrenochrome, which is simple, and has mild reaction conditions, high product purity, an impurity content less than 10−8%, and low subsequent processing cost, thereby having a great application prospect. The nitrogen-doped carbon tubes after use can be regenerated and recovered, and its reutilization is still able to realize the complete transformation of adrenaline. The high utilization rate of catalytic material conforms to the concept of energy conservation, minimizing the costs.

First claim

What is claimed is:

1. A method for preparing adrenochrome by catalytic oxidation using nitrogen-doped carbon nanotubes, which is characterized in that the method comprises the steps of:
S 1 : an appropriate amount of solid powder of nitrogen-doped carbon nanotubes is weighted and dispersed in a beaker containing ultrapure water, stirred on a magnetic stirring apparatus to give a uniform suspension of nitrogen-doped carbon nanotubes;
S 2 : a solid powder of adrenaline standards is dissolved in ultrapure water and ultrasonicated for 20 min to prepare an aqueous solution of adrenaline;
S 3 : the aqueous solution of adrenaline is added to the suspension of nitrogen-doped carbon nanotubes to keep a pH of 6-7 in the system and the reaction is stirred for 30-120 min with exclusion of light;
S 4 : the suspension is poured into a Buchner funnel after the end of reaction to perform vacuum filtration to give an aqueous solution of adrenochrome; the carbon tube solid on filter paper is washed appropriately with methanol, suction-filtered, and the filtrates are combined;
S 5 : a PPL solid phase extraction cartridge is used, which is activated with methanol, ultrapure water and 0.01M HCl before use; the aqueous solution of adrenochrome obtained in S 4 is passed through the PPL cartridge at an appropriate speed;
S 6 : After enrichment, the PPL cartridge is purified by an appropriate amount of ultrapure water; the PPL cartridge is then dried with pure N2, and then slowly eluted with an appropriate amount of methanol immediately;
S 7 : The collected eluant is dried over anhydrous sodium sulfate and placed into a low-temperature bath to cool for 30 min at −30° C.; after crystal precipitation, the crystal is washed with methanol and placed in a freeze drier to give a adrenochrome solid which is stored at −20° C., protected from light and sealed.

2. The method of claim 1 , which is characterized in that: the doped amount of the solid powder of nitrogen-doped carbon nanotubes described in S 1 is 1-5%.

3. The method of claim 1 , which is characterized in that: to obtain a uniform suspension of carbon nanotubes in S 1 , an ultrasonication for 20-30 min under a condition of 30-50 W is performed.

4. The method of claim 1 , which is characterized in that: the pre-treatment method of the PPL solid phase extraction cartridge in S 5 is as follows: the cartridge is activated with methanol with a volume of 6 ml*2 firstly, then wetted with 6.0 ml *2 of ultrapure water and the residual methanol is washed off, and finally the filler is adjusted to an acidic environment with 6 mL*2 of 0.01M HCl, and the flow rate of the aqueous solution of adrenochrome through the cartridge should not be higher than 2 mL/min.

5. The method of claim 1 , which is characterized in that: the purification of the cartridge in S 6 is by washing with ultrapure water with a volume of 6 mL*1, after drying with nitrogen, the cartridge is slowly eluted with 6 mL of methanol, in which the flow rate is controlled to 30 drops/min to ensure that the volume per minute through the cartridge is no more than 2 ml; due to the limited adsorbability of the filler in each PPL cartridge, if the amount of aqueous solution to be enriched is high, the samples can be loaded to multiple PPL cartridges simultaneously and finally the eluants are combined.

6. The method of claim 1 , which is characterized in that: the suspension of nitrogen-doped carbon nanotubes formulated in S 1 is added to an appropriate concentration of H 2 O 2 aqueous solution and stirred uniformly.

Assignees

• Univ Beijing

Inventors

• Zhu Dongqiang
• Yi Langsha
• Wei Chenhui

Classifications

• B01J2235/00

  Indexing scheme associated with group B01J35/00, related to the analysis techniques used to determine the catalysts form or properties · CPC title

• C07D209/36 Primary

  in position 3, e.g. adrenochrome · CPC title

• B01D15/125

  Pre-filtration · CPC title

• B01J27/24 Primary

  Nitrogen compounds · CPC title

• B01J21/185

  Carbon nanotubes (carbon nanotubes per se C01B32/15) · CPC title