CN114368762B - Exogenous source 15 NO donor sodium nitroprusside [ ] 15 Synthesis method of NO) - Google Patents

Exogenous source 15 NO donor sodium nitroprusside [ ] 15 Synthesis method of NO) Download PDF

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CN114368762B
CN114368762B CN202111324863.0A CN202111324863A CN114368762B CN 114368762 B CN114368762 B CN 114368762B CN 202111324863 A CN202111324863 A CN 202111324863A CN 114368762 B CN114368762 B CN 114368762B
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sodium nitroprusside
sodium
solid
nitroprusside
donor
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CN114368762A (en
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徐建飞
刘占峰
叶展宏
解龙
肖斌
吕竹茵
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Shanghai Research Institute of Chemical Industry SRICI
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    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01C—AMMONIA; CYANOGEN; COMPOUNDS THEREOF
    • C01C3/00—Cyanogen; Compounds thereof
    • C01C3/08—Simple or complex cyanides of metals
    • C01C3/12—Simple or complex iron cyanides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
    • C01P2006/00—Physical properties of inorganic compounds
    • C01P2006/80—Compositional purity
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/584—Recycling of catalysts

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Abstract

The application relates to an exogenous source 15 NO donor sodium nitroprusside [ ] 15 NO), comprising the steps ofThe steps are as follows: (1) Taking potassium ferrocyanide trihydrate and sodium nitrite 15 Dissolving N in water, adding catalyst, reacting, filtering to remove insoluble substances to obtain red transparent liquid sodium nitroprusside- & lt- & gt 15 NO) crude; (2) Sodium nitroprusside-NaN-N-nitroprusside 15 Adding copper sulfate into the NO) crude product, stirring, centrifugally separating and drying to obtain solid Cu [ Fe (CN) 5 15 NO]The method comprises the steps of carrying out a first treatment on the surface of the (3) Solid Cu [ Fe (CN) 5 15 NO]Mixing with sodium bicarbonate solution under stirring, adding small amount of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating for reaction, separating solid from liquid, and drying to obtain deep red solid sodium nitroprusside 15 NO). Compared with the prior art, the method does not adopt a commonly used crystallization method, can effectively improve the purity and the isotope abundance of the sodium nitroprusside, and has simple operation and short process flow. The total yield of the reaction is more than or equal to 80 percent, the chemical purity is more than or equal to 99 percent, and the isotope abundance is more than or equal to 99atom percent 15 N。

Description

Exogenous source 15 NO donor sodium nitroprusside [ ] 15 Synthesis method of NO)
Technical Field
The application belongs to the technical field of stable isotope labeled organic compounds, and relates to an exogenous source 15 NO donor sodium nitroprusside [ ] 15 NO).
Background
Nitric oxide is an important redox signal molecule and toxic molecule widely existing in plant tissues, is also active nitrogen (reactive nitrogen species, RNS), can regulate the growth and development of plants, and is involved in the processes of plant respiration, photomorphogenesis, seed germination, aging, apoptosis, disease resistance and the like, and the response process of plants to various adversity stresses. The function of nitric oxide on plants is twofold, namely, low-concentration NO can be used as an antioxidant to have a scavenging function on active oxygen clusters, and the nitric oxide can induce the expression of antioxidant enzyme genes, relieve oxidative damage caused by various stresses and enhance the stress resistance of plants; however, higher concentrations of NO can initiate free radical chain reactions, leading to cell damage. At present, the mechanism of action of NO in plant physiological process is basically still in the initial stage, and needs toUsing different concentrations of exogenous sources 15 The NO donor sodium nitroprusside can regulate and control plant photosynthesis, antioxidant system, osmotic regulation and other physiological metabolism, and provide data reference for cultivating new stress-resistant plant variety.
The prior published literature is not prepared 15 The purity of the product obtained by the preparation method of the common sodium nitroprusside is generally not high. The method disclosed in the synthetic route of sodium nitroprusside in the third volume of the handbook of inorganic Compound Synthesis, japanese society of chemistry, contains a large amount of inorganic salt impurities; the patent application with publication number CN103159233A discloses a synthesis process of sodium nitroprusside, the content of which is only 96% at the highest; the patent application with publication number CN110615448A discloses sodium nitroprusside for clinically treating hypertension emergency and acute left heart failure, the purity of the sodium nitroprusside is more than or equal to 99%, but the applicant finds that the prepared sodium nitroprusside still has a small amount of inorganic salt through repeated experiments, and the sodium nitroprusside cannot be applied to the patients without isotope labeling 15 Research on the action mechanism of NO in the physiological process of plants. Based on the above drawbacks, the present application is therefore directed to a method involving an exogenous source 15 NO donor sodium nitroprusside [ ] 15 Organic synthesis method of NO), high-purity high-abundance sodium nitroprusside- & lt 15 NO) application to 15 Research on the action mechanism of NO in the physiological process of plants.
Disclosure of Invention
The application aims to provide an external source 15 NO donor sodium nitroprusside [ ] 15 NO). The method does not adopt a commonly used crystallization method, can effectively improve the purity and the isotope abundance of the sodium nitroprusside, and has simple operation and short process flow. The total yield of the reaction is more than or equal to 80 percent, the chemical purity is more than or equal to 99 percent, and the isotope abundance is more than or equal to 99atom percent 15 N。
The aim of the application can be achieved by the following technical scheme:
exogenous source 15 NO donor sodium nitroprusside [ ] 15 NO), comprising the steps of:
(1) Taking potassium ferrocyanide trihydrate and sodium nitrite 15 Dissolving N in water, adding catalyst, reacting, filtering to remove insoluble substances to obtain redTransparent liquid sodium nitroprusside 15 NO) crude;
(2) Sodium nitroprusside-NaN-N-nitroprusside 15 Adding copper sulfate into the NO) crude product, stirring, centrifugally separating and drying to obtain solid Cu [ Fe (CN) 5 15 NO]；
(3) Solid Cu [ Fe (CN) 5 15 NO]Mixing with sodium bicarbonate solution under stirring, adding small amount of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating for reaction, separating solid from liquid, and drying to obtain deep red solid sodium nitroprusside 15 NO)。
In the application, the first step of reaction prepares the deep red sodium nitroprusside- & lt- & gt 15 NO) liquid, i.e. sodium nitroprusside 15 NO) the crude product is directly subjected to the second reaction without treatment.
Further, in the step (1), potassium ferrocyanide trihydrate and sodium nitrite 15 The molar ratio of N is (1-5): 1.
further, in the step (1), the catalyst is ultrafine copper powder, and the dosage of the catalyst is 1-5% of the mass of the potassium ferrocyanide trihydrate.
Further, in the step (1), the particle size of the superfine copper powder is between 1 and 100 nm.
Further, in the step (1), the reaction temperature is 0-100 ℃ and the reaction time is 2-12 h.
Further, in the step (2), copper sulfate and sodium nitroprusside used for preparing the same 15 The molar ratio of the potassium ferrocyanide trihydrate of the crude product of NO) is (1-5): 1.
further, in the step (2), the temperature of stirring is 30-120 ℃ and the time is 2-12 h.
Further, in the step (3), solid Cu [ Fe (CN) 5 15 NO]The molar ratio of the sodium bicarbonate to the sodium bicarbonate is 0.8-1.2: 1. Further, in the step (3), solid Cu [ Fe (CN) 5 15 NO]Molar ratio to sodium bicarbonate 1:1.
further, in the step (3), solid Cu [ Fe (CN) 5 15 NO]Molar ratio of the sodium dodecyl sulfate to disodium ethylenediamine tetraacetate (EDTA-2 Na) is 10-15: 1.
in the step (3), the temperature of the heating reaction is 30-120 ℃ and the time is 1-8 h.
The synthetic process route of the application is as follows:
compared with the prior art of preparing the conventional sodium nitroprusside product by adopting excessive nitric acid, potassium ferrocyanide and the like as raw materials, the sodium nitroprusside prepared by the application 15 NO) is an isotopic label, the labeling site is 15 NO, isotope source is sodium nitrite 15 The N-isotope labels are expensive and cannot be excessive in the reaction so as not to cause a significant increase in cost. The consumption of the raw material potassium ferrocyanide is excessive, and ultrafine copper powder is needed to be added as a catalyst in order to ensure the reaction efficiency.
In the application, a metal ion complexing agent disodium ethylenediamine tetraacetate (EDTA-2 Na) is used in the step (3), and the aim (1) is to promote the generation of sodium nitroprusside; (2) Because sodium nitroprusside is easy to oxidize and the solution is easy to change color, the purity is reduced, and the addition of the metal ion complexing agent disodium ethylenediamine tetraacetate (EDTA-2 Na) can effectively prevent sodium nitroprusside from being oxidized and improve the purity of the product.
The application uses potassium ferrocyanide trihydrate and sodium nitrite- 15 N is used as raw material, superfine copper powder is used as catalyst, and sodium nitroprusside- & lt- & gt is prepared by reaction 15 NO) crude; adding copper sulfate aqueous solution, centrifuging to obtain solid Cu [ Fe (CN) 5 15 NO]The method comprises the steps of carrying out a first treatment on the surface of the Mixing the solid with sodium bicarbonate solution, adding small amount of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating for reaction, centrifuging to obtain dark red liquid, and drying the spin-dried liquid to obtain dark red solid sodium nitroprusside- 15 NO). The method does not adopt a commonly used crystallization method, and can effectively improve sodium nitroprusside-sodium @ and 15 NO), and the purity and isotopic abundance of the NO), and the operation is simple, and the process flow is short. The total yield of the reaction is more than or equal to 80 percent (calculated by potassium ferrocyanide trihydrate), the chemical purity is more than or equal to 99 percent, and the isotopic abundance is more than or equal to 99atom percent 15 N (Thermo TSQ Quantum liquid chromatography-mass spectrometry) determination). The method stabilizes isotope labeled exogenous sources 15 The NO donor sodium nitroprusside has high yield, short process flow, simple operation, less byproducts and undiluted isotope abundance, is suitable for producing the stable isotope product in a laboratory, and has good economical efficiency and practical application value.
Detailed Description
The present application will be described in detail with reference to specific examples. The present embodiment is implemented on the premise of the technical scheme of the present application, and a detailed implementation manner and a specific operation process are given, but the protection scope of the present application is not limited to the following examples.
In the following examples, unless otherwise indicated, the starting materials or processing techniques are all conventional commercially available in the art.
Example 1
42.2g of potassium ferrocyanide trihydrate and 7g of sodium nitrite are taken 15 N is taken as a raw material, 100ml of water is used for dissolution, 0.42g of superfine copper powder is added as a catalyst, the particle size is 1nm, and after water bath reaction for 12 hours at 60 ℃, the reaction liquid is dark red. Filtering while hot to remove insoluble substances to obtain dark red transparent liquid which is sodium nitroprusside- & lt- & gt 15 NO) crude product. The liquid is directly subjected to the second step reaction without treatment.
16g of anhydrous copper sulfate is added into the red transparent liquid, and the mixture is stirred for 2 hours at 120 ℃ to generate more solid, and the solid Cu [ Fe (CN) is obtained after centrifugation at 4000 rpm 5 15 NO]And (5) drying in vacuum.
Solid Cu [ Fe (CN) 5 15 NO]Mixing with 13.7g sodium bicarbonate (the molar ratio of the two is controlled at 1:1), mixing 200ml water, stirring, adding 0.016mol of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating at 30 ℃ for reaction for 8 hours, making the reaction solution dark, centrifuging at 4000 rpm to obtain dark red liquid, spin-drying the liquid, and vacuum drying to obtain dark red solid sodium nitroprusside- 15 NO) 24.5g. The total yield of the reaction is 82 percent (sodium nitrite) 15 N) with chemical purity greater than or equal to 99% and isotope abundance greater than or equal to 99atom% 15 N (Thermo TSQ Quantum liquid Mass Spectrometry).
Example 2
84.4g of potassium ferrocyanide trihydrate and 7g of sodium nitrite are taken 15 N is taken as a raw material, 100ml of water is used for dissolution, 1g of superfine copper powder is added as a catalyst, the particle size is 50nm, and after water bath reaction for 6 hours at 0 ℃, the reaction liquid is in dark red. Filtering while hot to remove insoluble substances to obtain dark red transparent liquid which is sodium nitroprusside- & lt- & gt 15 NO) crude product. The liquid is directly subjected to the second step reaction without treatment.
Adding 32g anhydrous copper sulfate into red transparent liquid, stirring at 30 deg.C for 12 hr to obtain more solid, centrifuging at 3000 rpm to obtain solid Cu [ Fe (CN) 5 15 NO]And (5) drying in vacuum.
Solid Cu [ Fe (CN) 5 15 NO]Mixing with 14.3g sodium bicarbonate (the molar ratio of the two is controlled at 1:1), mixing 200ml water, stirring, adding 0.011mol of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating at 80 ℃ for reaction for 4 hours, making the reaction solution dark, centrifuging at a centrifugal speed of 3000 r/min to obtain dark red liquid, spin-drying the liquid, and vacuum drying to obtain dark red solid sodium nitroprusside- 15 NO) 25.1g. The total yield of the reaction is 84 percent (sodium nitrite) 15 N) with chemical purity greater than or equal to 99% and isotope abundance greater than or equal to 99atom% 15 N (Thermo TSQ Quantum liquid Mass Spectrometry).
Example 3
211g of potassium ferrocyanide trihydrate and 7g of sodium nitrite are taken 15 N is taken as a raw material, 100ml of water is used for dissolution, 2.11g of superfine copper powder is added as a catalyst, the particle size is 100nm, and after water bath reaction for 2 hours at the temperature of 100 ℃, the reaction liquid is dark red. Filtering while hot to remove insoluble substances to obtain dark red transparent liquid which is sodium nitroprusside- & lt- & gt 15 NO) crude product. The liquid is directly subjected to the second step reaction without treatment.
79.5g of anhydrous copper sulfate is added into the red transparent liquid, and the mixture is stirred for 6 hours at 50 ℃ to generate more solid, and the solid Cu [ Fe (CN) is obtained after centrifugation at 2000 rpm 5 15 NO]And (5) drying in vacuum.
Solid Cu [ Fe (CN) 5 15 NO]Mixing with 14.5g sodium bicarbonate (the molar ratio of the two is controlled at 1:1), mixing with 200ml water, stirring,adding 0.014mol of disodium ethylenediamine tetraacetate (EDTA-2 Na), heating at 120deg.C for reaction for 1 hr, making the reaction solution dark, centrifuging at 2000 rpm to obtain dark red liquid, spin drying the liquid, and vacuum drying to obtain dark red solid sodium nitroprusside- ("A") 15 NO) 25.4g. The total yield of the reaction is 85 percent (sodium nitrite) 15 N) with chemical purity greater than or equal to 99% and isotope abundance greater than or equal to 99atom% 15 N (Thermo TSQ Quantum liquid Mass Spectrometry).
Comparative example 1:
as compared with example 1, the preparation method is largely the same except that sodium nitrite is added 15 N is replaced by 2 times mole of nitric acid 15 N, without using superfine copper powder as catalyst, the total reaction yield is 40 percent (using nitric acid- 15 N) with chemical purity not less than 99% and isotope abundance not less than 98atom% 15 N。
Comparative example 2:
the reaction was not performed, except that the addition of the ultra fine copper powder was omitted, as compared with example 1, for the most part.
Comparative example 3:
as compared with example 1, the reaction was carried out in the same manner as in example 1 except that disodium ethylenediamine tetraacetate (EDTA-2 Na) was not added to the reaction mixture in an overall yield of 75% (in terms of nitric acid- 15 N) with chemical purity not less than 97% and isotope abundance not less than 98atom% 15 N。
The previous description of the embodiments is provided to facilitate a person of ordinary skill in the art in order to make and use the present application. It will be apparent to those skilled in the art that various modifications can be readily made to these embodiments and the generic principles described herein may be applied to other embodiments without the use of the inventive faculty. Therefore, the present application is not limited to the above-described embodiments, and those skilled in the art, based on the present disclosure, should make improvements and modifications without departing from the scope of the present application.

Claims (8)

1. Exogenous source 15 NO donor sodium nitroprusside [ ] 15 NO), characterized by comprising the steps of:
(1) Taking ferrocyanidePotassium trihydrate and sodium nitrite 15 Dissolving N in water, adding catalyst, reacting, filtering to remove insoluble substances to obtain red transparent liquid sodium nitroprusside- & lt- & gt 15 NO) crude;
(2) Sodium nitroprusside-NaN-N-nitroprusside 15 Adding copper sulfate into the NO) crude product, stirring, centrifugally separating and drying to obtain solid Cu [ Fe (CN) 5 15 NO]；
(3) Solid Cu [ Fe (CN) 5 15 NO]Mixing with sodium bicarbonate solution under stirring, adding disodium ethylenediamine tetraacetate, heating for reaction, separating solid from liquid, and drying to obtain deep red solid sodium nitroprusside 15 NO)；
Potassium ferrocyanide trihydrate and sodium nitrite 15 The molar ratio of N is (1-5): 1, a step of;
in the step (1), the catalyst is ultrafine copper powder, and the dosage of the catalyst is 1-5% of the mass of the potassium ferrocyanide trihydrate.
2. An external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), characterized in that in step (1), the particle size of the ultrafine copper powder is between 1 and 100 nm.
3. An external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), wherein in the step (1), the reaction temperature is 0-100 ℃ and the reaction time is 2-12 h.
4. An external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 The synthesis method of NO) is characterized in that in the step (2), copper sulfate and sodium nitroprusside used for preparing the same 15 The molar ratio of the potassium ferrocyanide trihydrate of the crude product of NO) is (1-5): 1.
5. an external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), wherein in the step (2), the stirring temperature is 3The temperature is 0-120 ℃ and the time is 2-12 h.
6. An external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), characterized in that in step (3), solid Cu [ Fe (CN) 5 15 NO]The molar ratio of the sodium bicarbonate to the sodium bicarbonate is 0.8-1.2: 1.
7. an external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), characterized in that in step (3), solid Cu [ Fe (CN) 5 15 NO]The molar ratio of the sodium ethylene diamine tetraacetate to the disodium is 10-15: 1.
8. an external source according to claim 1 15 NO donor sodium nitroprusside [ ] 15 NO), characterized in that in step (3), the heating reaction temperature is 30-120 ℃ and the time is 1-8 h.
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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1478578A1 (en) * 1987-04-24 1995-07-20 Научно-исследовательский институт технологии и безопасности лекарственных средств Method for production of sodium nitroprusside
CN103159233A (en) * 2011-12-09 2013-06-19 康普药业股份有限公司 Sodium nitroprusside synthesis process
CN107141345A (en) * 2017-06-07 2017-09-08 南京师范大学 A kind of keratin large biological molecule nitric oxide donors and its synthesis and application
CN110342541A (en) * 2019-07-01 2019-10-18 嘉实（湖南）医药科技有限公司 A kind of method that the general hydrogen of nitre prepares sodium nitroprussiate
CN110615448A (en) * 2018-06-20 2019-12-27 四川科瑞德凯华制药有限公司 Method for preparing sodium nitroprusside

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU1478578A1 (en) * 1987-04-24 1995-07-20 Научно-исследовательский институт технологии и безопасности лекарственных средств Method for production of sodium nitroprusside
CN103159233A (en) * 2011-12-09 2013-06-19 康普药业股份有限公司 Sodium nitroprusside synthesis process
CN107141345A (en) * 2017-06-07 2017-09-08 南京师范大学 A kind of keratin large biological molecule nitric oxide donors and its synthesis and application
CN110615448A (en) * 2018-06-20 2019-12-27 四川科瑞德凯华制药有限公司 Method for preparing sodium nitroprusside
CN110342541A (en) * 2019-07-01 2019-10-18 嘉实（湖南）医药科技有限公司 A kind of method that the general hydrogen of nitre prepares sodium nitroprussiate

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