CN105503661A - Method for synthesizing 1-amino-3-nitroguanidine - Google Patents
Method for synthesizing 1-amino-3-nitroguanidine Download PDFInfo
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- CN105503661A CN105503661A CN201610018973.7A CN201610018973A CN105503661A CN 105503661 A CN105503661 A CN 105503661A CN 201610018973 A CN201610018973 A CN 201610018973A CN 105503661 A CN105503661 A CN 105503661A
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- Prior art keywords
- nitroguanidine
- amino
- methyl
- hydrazine hydrate
- water
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for synthesizing 1-amino-3-nitroguanidine. The method comprises the following steps of adding 2-methyl-3-nitryl isothiourea to water, dropwise adding hydrazine hydrate with the concentration being 80%, after adding of the hydrazine hydrate is ended, raising the temperature to 40-70 DEG C, preserving the temperature for 3-6 hours, conducting cooling and filtration, and conducting elution and drying with water and ethyl alcohol, so that amino nitroguanidine is obtained, wherein the mole ratio of the hydrazine hydrate to the 2-methyl-3-nitryl isothiourea is 1: (1-2). The method is mainly applied to 1-amino-3-nitroguanidine synthesis.
Description
Technical field
The present invention relates to a kind of synthetic method of synthesizing 1-amino-3-nitroguanidine, belong to energetic material field.
Background technology
High-nitrogen energetic materials is the novel energetic material that the class grown up in recent years has applications well prospect, has high positive Enthalpies of Formation, Heat stability is good, and the high nitrogen low-carbon (LC) in molecular structure, hydrogen richness make it more easily reach oxygen balance, and N in products of combustion
2content is high, H
2o and CO
2content is low, reduces the characteristic signal of exit gas product.The electrostatic sensitivity of part of compounds, shock sensitivity, friction sensitivity are all lower.Superiority due to high-nitrogen energetic materials self makes it have potential application prospect in energetic material fields such as low characteristic signal propellant, novel high-energy desensitized explosives.1-amino-3-nitroguanidine (ANG) its density is 1.722g/cm
3, quick-fried heat is 3310K, and explosion velocity is 8729m/s, and detonation pressure is 307Kbar, gas production rate 878L/kg, and nitrogen content is 58.8%.Be a kind of high-nitrogen energetic materials, be expected to promote the use of in weaponry.
NikoFischer is at " 1-Amino-3-nitroguanidine (ANQ) inhigh-performanceionicenergeticmaterials " JournalofHigh-performanceionicenergeticmaterials2012, report the synthetic method of 1-amino-3-nitroguanidine in 573-588, its synthetic route is as follows:
Nitroguanidine is added to the water and is warming up to 55 DEG C by this synthetic method, drips the hydrazine hydrate time to be greater than 15min, and be chilled to room temperature, have hydrochloric acid to regulate PH=7, freeze overnight obtains product hot water recrystallization and obtains sterling.The method mainly has the following disadvantages: reactions steps is long, and post-reaction treatment is complicated.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, provides a kind of reactions steps short, simple to operate, the simple 1-amino of post-treating method-3-nitroguanidine synthetic method.
The present invention conceives: provide a kind of synthesis step short, the simple 1-amino of post-treating method-3-nitroguanidine synthetic method.Synthetic route of the present invention is as follows:
Of the present invention is a kind of synthetic method of 1-amino-3-nitroguanidine, and its structural formula is as shown in (I):
With 2-methyl-3-nitro isothiourea for raw material, its structural formula is as shown in (II), synthetic method of the present invention comprises the following steps: be added to the water by 2-methyl-3-nitro isothiourea, dripping mass percent is the hydrazine hydrate of 80%, add and be warming up to 40 ~ 70 DEG C, insulation 3 ~ 6h cooling, filter, obtain amino nitroguanidine with water and ethanol rinse, drying step, wherein hydrazine hydrate and 2-methyl-3-nitro isothiourea and nitric acid molar ratio are 1:1 ~ 2.
2, the synthetic method of amino nitroguanidine according to claim 1, comprises the following steps:
2-methyl-3-nitro isothiourea is added to the water, dripping mass percent is the hydrazine hydrate of 80%, add and be warming up to 50 DEG C, insulation 5h cooling, filtration, obtain amino nitroguanidine with water and ethanol rinse, drying step, wherein hydrazine hydrate and 2-methyl-3-nitro isothiourea and nitric acid molar ratio are 1:1.
Advantage of the present invention:
The inventive method, with commercial reagent 2-methyl-3-nitro isothiourea for raw material, reactions steps is a step, operating process is simple, and after aftertreatment simple reaction, direct filtration obtains product, and in documents, commercial reagent nitroguanidine is raw material, reactions steps is two steps, and post-reaction treatment is complicated.
Embodiment
Below in conjunction with embodiment, the present invention is described in further details.
Embodiment 1
Under room temperature, 2g (19.4mmol) 2-methyl-3-nitro isothiourea is added in the water of 40mL, drip 80%1.21g (19.4mmol) hydrazine hydrate, add and be warming up to 50 DEG C, insulation 5h, cooling, filters, filter cake obtains white solid 1.28g through ethanol rinse, drying step, yield 50%.
Structural Identification
Infrared spectra IR (KBr, cm
-1) ν: 3390,3323,3295,3216,1668,1618,1578,1281,1179,1010,708,639
Nuclear magnetic spectrum:
13cNMR (DMSO-d6,125MHz), δ: 161.549;
1HNMR(DMSO-d
6,500MHz)δ:9.324,8.267,7.549,4.678
Ultimate analysis: structural formula C
1h
5n
5o
2
Theoretical value: C10.08, H4.20, N58.82;
Measured value: C9.83, H4.35, N58.73;
The material that said structure appraising datum proved step obtains is 1-amino-3-nitroguanidine really.
Embodiment 2
Under room temperature, 4g (38.8mmol) 2-methyl-3-nitro isothiourea is added in the water of 40mL, drip 80%1.21g (19.4mmol) hydrazine hydrate, add and be warming up to 50 DEG C, insulation 5h, cooling, filters, filter cake obtains white solid 1.15g through ethanol rinse, drying step, yield 45%.
Embodiment 3
Under room temperature, 2g (19.4mmol) 2-methyl-3-nitro isothiourea is added in the water of 40mL, drip 80%1.21g (19.4mmol) hydrazine hydrate, add and be warming up to 70 DEG C, insulation 6h, cooling, filters, filter cake obtains white solid 1.2g through ethanol rinse, drying step, yield 47%.
Embodiment 4
Under room temperature, 2g (19.4mmol) 2-methyl-3-nitro isothiourea is added in the water of 40mL, drip 80%1.21g (19.4mmol) hydrazine hydrate, add and be warming up to 40 DEG C, insulation 3h, cooling, filters, filter cake obtains white solid 1.0g through ethanol rinse, drying step, yield 40%.
Claims (2)
1. a synthetic method for 1-amino-3-nitroguanidine, the structural formula of 1-amino-3-nitroguanidine is as shown in (I):
With 2-methyl-3-nitro isothiourea for raw material, its structural formula is as shown in (II), comprise the following steps: 2-methyl-3-nitro isothiourea is added to the water, dripping mass percent is the hydrazine hydrate of 80%, add and be warming up to 40 ~ 70 DEG C, insulation 3 ~ 6h cooling, filter, with water and ethanol rinse, dry 1-amino-3-nitroguanidine, wherein hydrazine hydrate and 2-methyl-3-nitro isothiourea and nitric acid molar ratio are 1:1 ~ 2.
2. the synthetic method of 1-amino-3-nitroguanidine according to claim 1, comprises the following steps:
2-methyl-3-nitro isothiourea is added to the water, dripping mass percent is the hydrazine hydrate of 80%, add and be warming up to 50 DEG C, insulation 5h cooling, filtration, with water and ethanol rinse, dry 1-amino-3-nitroguanidine, wherein hydrazine hydrate and 2-methyl-3-nitro isothiourea and nitric acid molar ratio are 1:1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610018973.7A CN105503661A (en) | 2016-01-12 | 2016-01-12 | Method for synthesizing 1-amino-3-nitroguanidine |
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|---|---|---|---|
| CN201610018973.7A CN105503661A (en) | 2016-01-12 | 2016-01-12 | Method for synthesizing 1-amino-3-nitroguanidine |
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| CN105503661A true CN105503661A (en) | 2016-04-20 |
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| CN201610018973.7A Pending CN105503661A (en) | 2016-01-12 | 2016-01-12 | Method for synthesizing 1-amino-3-nitroguanidine |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109580873A (en) * | 2018-12-27 | 2019-04-05 | 湖北航天化学技术研究所 | A kind of measuring method of triamido guanidine nitrate purity |
| CN115745848A (en) * | 2022-12-07 | 2023-03-07 | 上海优合生物科技有限公司 | Processing and synthesizing process of aminoguanidine |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051434A (en) * | 1988-11-29 | 1991-09-24 | Nihon Tokushu Noyaku Seizo K.K. | Insecticidally active nitro guanidine compounds |
| CN1251089A (en) * | 1997-03-27 | 2000-04-19 | 拜尔公司 | Method for producing N-alkyl-N'-nitroguanidines |
| WO2010060231A1 (en) * | 2008-11-25 | 2010-06-03 | Qin Zhaohai | Condensed amino nitroguanidine compounds, synthesis and use as botanical insecticides thereof |
| CN102863360A (en) * | 2012-10-16 | 2013-01-09 | 中国农业大学 | Synthetic method of novel nitro arylideneamino guanidine derivatives |
-
2016
- 2016-01-12 CN CN201610018973.7A patent/CN105503661A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5051434A (en) * | 1988-11-29 | 1991-09-24 | Nihon Tokushu Noyaku Seizo K.K. | Insecticidally active nitro guanidine compounds |
| CN1251089A (en) * | 1997-03-27 | 2000-04-19 | 拜尔公司 | Method for producing N-alkyl-N'-nitroguanidines |
| WO2010060231A1 (en) * | 2008-11-25 | 2010-06-03 | Qin Zhaohai | Condensed amino nitroguanidine compounds, synthesis and use as botanical insecticides thereof |
| CN102863360A (en) * | 2012-10-16 | 2013-01-09 | 中国农业大学 | Synthetic method of novel nitro arylideneamino guanidine derivatives |
Non-Patent Citations (1)
| Title |
|---|
| SORBA, GIOVANNI等: "Potential histamine H2-receptor antagonists: ranitidine analogs containing semicarbazono equivalent groups", 《ARCHIV DER PHARMAZIE (WEINHEIM, GERMANY)》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109580873A (en) * | 2018-12-27 | 2019-04-05 | 湖北航天化学技术研究所 | A kind of measuring method of triamido guanidine nitrate purity |
| CN115745848A (en) * | 2022-12-07 | 2023-03-07 | 上海优合生物科技有限公司 | Processing and synthesizing process of aminoguanidine |
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Application publication date: 20160420 |