CN101665434A - Safe separation and purification method of nitrate ester - Google Patents
Safe separation and purification method of nitrate ester Download PDFInfo
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- CN101665434A CN101665434A CN200910307026A CN200910307026A CN101665434A CN 101665434 A CN101665434 A CN 101665434A CN 200910307026 A CN200910307026 A CN 200910307026A CN 200910307026 A CN200910307026 A CN 200910307026A CN 101665434 A CN101665434 A CN 101665434A
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Abstract
The invention discloses a safe separation and purification method of nitrate ester, comprising the steps: organic solvent is distilled from the organic solution of nitrate ester by distillation; in distillation, distilled water is added into the organic solution of nitrate ester; and the organic solvent and water can form azeotropy, azeotrope formed by the distilled water and the organic solvent is distilled out, distillate is collected, the organic solvent is completely distilled out, then residue is obtained and divided into liquid-liquid two phases after standing, and the nitrate ester product phase at a lower layer is covered by the water phase. Compared with the method for removing the organic solvent from the nitrate ester by direct atmospheric and vacuum distillation, the safe separation and purification method of nitrate ester is simple in operation, safe and clean in process and high in product purity and yield, and leads the obtained nitrate ester to be safely protected by water, avoid dangers, and be stored for a long time.
Description
Technical field
The present invention relates to nitrate compound highly effective and safe separating and purifying method, belong to the nitric ether purification technique.
Background technology
Nitric ether is a kind of important organic compound, in medicine, agricultural chemicals, civil explosive and military field purposes is very widely arranged.In nitric ether was synthetic, traditional method was starting raw material mostly with the polyvalent alcohol, adopted nitre-sulphur nitration mixture, nitric acid etc. to be prepared as nitrating agent.At present, with the nitrogen pentoxide be the research focus that the novel nitrated technology of the nitrated epoxy compounds of nitrating agent becomes the nitric acid synthesis ester compound.Yet normally exist through the nitric ether product that above-mentioned preparation method obtains,, need separate purification, remove organic solvent the nitric ether organic solution that obtains in order to obtain pure nitric ether product with the organic solution form of nitric ether.
People such as patent EP0223440 and Golding (Tetrahedron Letters l 988,29 (22): 2731-2734; Tetrahedronl993,49 (32): 705-170 62) obtain corresponding dinitrate with nitrated oxa-ring of the organic solution of nitrogen pentoxide and nitrogen heterocyclic, adopt direct underpressure distillation mode to steam organic solvent down at 30 ℃ and obtain pure nitric ether product.Patent GB2352239 and GB6072071 then adopt vacuum-drying to remove organic solvent in the product to the nitrated glycerin dinitrate for preparing of nitrogen pentoxide and polyvalent alcohol nitric ether organic solution, obtain pure nitric ether.People such as Hu Zhihua (Speciality Petrochemicals, 2004,2:1-3) the nitrated ethoxylated dodecyl alcohol nitric ether organic solvent for preparing of nitric-sulfuric acid is adopted air distillation mode refined product, reclaim solvent simultaneously.People such as Ma Qing (synthetic chemistry, 2008,16 (6): 628-631) adopt the mode of two step underpressure distillation that the nitrated Racemic glycidol nitric ether for preparing of concentrated nitric acid is separated purification with the poly epihydric alcohol nitric ether, adopt 40 ℃ of underpressure distillation 1h respectively, remove organic solvent at 55 ℃ of underpressure distillation 2h then and obtain the nitric ether product.
As from the foregoing, the nitric ether organic solution that both at home and abroad nitration reaction is obtained at present adopts normal decompression straight run distillation mode to remove organic solvent usually and obtains pure nitric ether product.It is very unstable that yet most of pure nitric ether products are heated, and especially the later stage very easily blasts in distillation in above-mentioned still-process and wait danger.
Summary of the invention
In order to solve problems of the prior art, the invention provides a kind of safe separating method of purification of nitric ether, solve in the prior art and be subjected to the easy explosion caused dangerous problem that waits of thermally labile because of pure nitric ether product.
The present invention is achieved by the following technical solutions: a kind of safe separating method of purification of nitric ether, comprise the step that the organic solution of nitric ether is steamed organic solvent in the distillation mode, during distillation, in the organic solution of described nitric ether, add distilled water, the volume ratio of the organic solution of distilled water and described nitric ether was controlled at 1: 1 ~ 100: 1, control pressure adds thermal rectification under 0.01MPa ~ 0.1MPa, described organic solvent can form azeotropic with water, the azeotrope of distilled water and organic solvent formation is distilled away, collect overhead product, after organic solvent distills away fully, be divided into liquid liquid two-phase after the still liquid that obtains leaves standstill, lower floor's nitric ether product is covered by water.
Described nitric ether is wherein a kind of of monohydroxy-alcohol nitric ether, dibasic alcohol nitric ether, polyvalent alcohol nitric ether or nitrous acid ester.
Described organic solvent is wherein a kind of of halohydrocarbon, other alkane or aromatic hydroxy compound.
The volume ratio of the organic solution of described distilled water and described nitric ether preferably was controlled at 1: 1 ~ 50: 1.
Described distillation pressure is preferably 0.03MPa ~ 0.1MPa.
Described overhead product boiling point control is at 20 ~ 90 ℃.
Described overhead product boiling point preferably is controlled at 20 ~ 60 ℃.
(j) preparing an oil-based drilling mud comprising the combined oil of step (g). the safe separating method of purification of nitric ether provided by the invention and normal decompression straight run distillation mode remove in the nitric ether method of organic solvent and compare, simple to operate, process safety, cleaning, product purity and yield height, the solvent recovering rate height.The nitric ether that obtains is under the safeguard protection of water, avoids causing danger, and can deposit for a long time.Nitric ether organic solution sepn process involved in the present invention is that nitric ether is separated the pure nitric ether that obtains being in the stored safely state from its organic solution, yield and purity height, process safety, and the sample that obtains can directly be stored.The meeting natural layering can reclaim organic solvent after the azeotrope that distills out left standstill after simple separation.
Embodiment
Below in conjunction with specific embodiment the present invention is done to describe in detail.
The organic solution of nitric ether is joined in the distillation tower, add a certain amount of distilled water, the volume ratio of water and organic solution was controlled at 100: 1 ~ 1: 1.Add thermal rectification under 0.01MPa ~ 0.1MPa, the azeotrope that water and organic solvent are formed distills away; After organic solvent distills away fully, be divided into liquid-liquid two-phase after the still liquid that obtains leaves standstill, lower floor's nitric ether product is covered by water.
The mentioned nitric ether of the present invention can be monohydroxy-alcohol nitric ether, dibasic alcohol nitric ether or polyvalent alcohol nitric ether, also can be nitrous acid ester.
The organic solvent that the present invention carried is the organism that can form azeotrope with water, can be halohydrocarbon such as methylene dichloride, trichloromethane, tetracol phenixin, ethylene dichloride, 2 cbloropropane isopropyl chloride, Butyryl Chloride etc., also can be other alkane or aromatic hydroxy compound such as acetonitrile, benzene,toluene,xylene, hexanaphthene, pentane, heptane, nonane etc.
The water add-on is that the volume ratio of water and organic solution preferably was controlled at 1: 1 ~ 50: 1 in the said process; Distillation pressure should be regulated according to the boiling point of azeotrope, preferably is controlled at 0.03MPa ~ 0.1MPa; The overhead product boiling point control preferably is controlled at 20 ~ 60 ℃ at 20 ~ 90 ℃.
Embodiment 1
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in dichloromethane solution, obtain the dibasic alcohol nitric ether as 1,2-propylene glycol dinitrate (PGDN))/dichloromethane solution 40mL (gross weight 57g, wherein the PGDN mass content 7%) join in the 1000mL still kettle, add 400mL distilled water.Under 0.1MPa, add thermal distillation, collect 38 ℃ ~ 40 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 398.5g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.9%; Steaming the cut gross weight is 56.5g, separates, and reclaiming lower floor's organism weight is 51.5g, the rate of recovery 97%.
Embodiment 2
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in chloroform soln, obtain 1,2-propylene glycol dinitrate (PGDN)/chloroform soln 40mL (gross weight 63.2g, wherein the PGDN mass content 6.3%) joins in the 500mL still kettle, adds 200mL distilled water.Under 0.1MPa, add thermal distillation, collect 55 ℃ ~ 61 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 202g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.8%; Steam cut and be divided into two-layerly automatically, gross weight is 59.5g, and Separation and Recovery lower floor organism weight is 57.6g, the rate of recovery 97.3%.
Embodiment 3
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in tetrachloromethane solution, obtain 1,2-propylene glycol dinitrate (PGDN)/tetrachloromethane solution 40mL (gross weight 67.6g, wherein the PGDN mass content 5.9%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 65 ℃ ~ 68 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 41.3g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.8%; Steam cut and be divided into two-layerly automatically, gross weight is 65.3g, and Separation and Recovery lower floor organism weight is 62.7g, the rate of recovery 98.6%.
Embodiment 4
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in n-propyl chloride solution, obtain 1,2-propylene glycol dinitrate (PGDN)/n-propyl chloride solution 40mL (gross weight 39.7g, wherein the PGDN mass content 10%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 43 ℃ ~ 46 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 43g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.9%; Steam cut and be divided into two-layerly automatically, gross weight is 35.5g, and Separation and Recovery upper strata organism weight is 34.6g, the rate of recovery 97%.
Embodiment 5
Propylene oxide and nitrogen pentoxide 1, are carried out nitration reaction in the 2-dichloroethane solution, obtain 1,2-propylene glycol dinitrate (PGDN)/1,2-dichloroethane solution 40mL (gross weight 54g, wherein the PGDN mass content 7.4%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 70 ℃ ~ 73 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 39.5 in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.8%; Steam cut and be divided into two-layerly automatically, gross weight is 53.8g, and Separation and Recovery lower floor organism weight is 49.3g, the rate of recovery 98.6%.
Embodiment 6
With glycerol or nitroglycerine and nitrogen pentoxide 1, carry out nitration reaction in the 2-dichloroethane solution, obtain nitroglycerine (NG)/1,2-dichloroethane solution 40mL (gross weight 54g, wherein the NG mass content 7.4%) join in the 100mL still kettle, add 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 70 ℃ ~ 73 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the NG product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 39.5g in the weighing still kettle, and the purity of stratographic analysis NG is 99.6%; Steam cut and be divided into two-layerly automatically, gross weight is 53.8g, and Separation and Recovery lower floor organism weight is 49.1g, the rate of recovery 98%.
Embodiment 7
With 1,2-butylene oxide ring and nitrogen pentoxide carry out nitration reaction in dichloromethane solution, obtain 1,2-butyleneglycol dinitrate (BTDN)/dichloromethane solution 40mL (gross weight 57g, wherein the BTDN mass content 7%) join in the 100mL still kettle, add 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 38 ℃ ~ 40 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the BTDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 38.6g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.9%; Steaming the cut gross weight is 56.6g, separates, and reclaiming lower floor's organism weight is 51.6g, the rate of recovery 97.3%.
Embodiment 8
Racemic glycidol and nitrogen pentoxide are carried out nitration reaction in dichloromethane solution, obtain nitroglycerine Mononitrate (GLYN)/dichloromethane solution 40mL (gross weight 57g, wherein the GLYN mass content 7%) join in the 100mL still kettle, add 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 38 ℃ ~ 40 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the GLYN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 38.6g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.9%; Steaming the cut gross weight is 56.5g, separates, and reclaiming lower floor's organism weight is 51.5g, the rate of recovery 97%.
Embodiment 9
Epoxy chloropropane and nitrogen pentoxide 1, are carried out nitration reaction in the 2-dichloroethane solution, obtain 3-chloro-1,2-propylene glycol dinitrate (CPDN)/1,2-monochloroethane solution 40mL (gross weight 54g, wherein the CPDN mass content 7.4%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 70 ℃ ~ 73 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the CPDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 39.6g in the weighing still kettle, and the purity of stratographic analysis NG is 99.7%; Steam cut and be divided into two-layerly automatically, gross weight is 53.9g, and Separation and Recovery lower floor organism weight is 49.2g, the rate of recovery 98.4%.
Embodiment 10
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in benzole soln, obtain the dibasic alcohol nitric ether as 1,2-propylene glycol dinitrate (PGDN))/benzole soln 40mL (gross weight 39.2g, wherein the PGDN mass content 10.2%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.03MPa, add thermal distillation, collect 60 ℃ ~ 65 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid-liquid two-phase state, and lower floor is the PGDN product, the water of upper strata for not steaming.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 38.8g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.5%; Steaming the cut gross weight is 40.0g, separates, and reclaiming upper strata organism weight is 34.5g, the rate of recovery 98%.
Embodiment 11
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in acetonitrile solution, obtain the dibasic alcohol nitric ether as 1,2-propylene glycol dinitrate (PGDN))/acetonitrile solution 40mL (gross weight 35g, wherein the PGDN mass content 11.4%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.01MPa, add thermal distillation, collect 20 ℃ ~ 25 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the PGDN product, and the water that the upper strata is not steamed covers.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 38.8g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.8%; Steaming the cut gross weight is 36.0g, separates, and reclaiming lower floor's organism weight is 30.5g, the rate of recovery 98%.
Embodiment 12
Propylene oxide and nitrogen pentoxide are carried out nitration reaction in pentane solution, obtain the dibasic alcohol nitric ether as 1,2-propylene glycol dinitrate (PGDN))/pentane solution 40mL (gross weight 29.2g, wherein the PGDN mass content 13.7%) joins in the 100mL still kettle, adds 40mL distilled water.Under 0.1MPa, add thermal distillation, collect 33 ℃ ~ 35 ℃ cut, in receiving flask, be divided into two-layer after cut is cooled automatically.When the cut temperature raises suddenly, stop heating, leave standstill, gained still liquid is liquid liquid two-phase state, and lower floor is the PGDN product, and the water that the upper strata is not steamed covers.Product and overhead product are cooled to room temperature, and the weight of nitric ether and water is 43.5g in the weighing still kettle, and the purity of stratographic analysis nitric ether is 99.8%; Steaming the cut gross weight is 26.0g, separates, and reclaiming lower floor's organism weight is 24.9g, the rate of recovery 98.8%.
Claims (7)
1. the safe separating method of purification of a nitric ether, comprise the step that the organic solution of nitric ether is steamed organic solvent in the distillation mode, it is characterized in that, during distillation, in the organic solution of described nitric ether, add distilled water, the volume ratio of the organic solution of distilled water and described nitric ether was controlled at 1: 1 ~ 100: 1, control pressure adds thermal rectification under 0.01MPa ~ 0.1MPa, described organic solvent can form azeotropic with water, the azeotrope of distilled water and organic solvent formation is distilled away, collect overhead product, after organic solvent distills away fully, be divided into liquid-liquid two-phase after the still liquid that obtains leaves standstill, lower floor's nitric ether product is covered by water.
2. according to the safe separating method of purification of the described nitric ether of claim 1, it is characterized in that described nitric ether is wherein a kind of of monohydroxy-alcohol nitric ether, dibasic alcohol nitric ether, polyvalent alcohol nitric ether or nitrous acid ester.
3. according to the safe separating method of purification of the described nitric ether of claim 1, it is characterized in that described organic solvent is wherein a kind of of halohydrocarbon, other alkane or aromatic hydroxy compound.
4. according to the safe separating method of purification of the described nitric ether of claim 1, it is characterized in that the volume ratio of the organic solution of described distilled water and described nitric ether was controlled at 1: 1 ~ 50: 1.
5. according to the safe separating method of purification of the described nitric ether of claim 1, it is characterized in that described distillation pressure is 0.03MPa ~ 0.1MPa.
6. according to the safe separating method of purification of the described nitric ether of claim 1, it is characterized in that described overhead product boiling point control is at 20 ~ 90 ℃.
7. according to the safe separating method of purification of the described nitric ether of claim 6, it is characterized in that described overhead product boiling point control is at 20 ~ 60 ℃.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102816032A (en) * | 2012-09-11 | 2012-12-12 | 北京理工大学 | Xylitol nitrate ray-level simulation explosive mimics |
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| GB2352239A (en) * | 1999-07-03 | 2001-01-24 | Secr Defence | Preparation of Glycerol Dinitrates |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102816032A (en) * | 2012-09-11 | 2012-12-12 | 北京理工大学 | Xylitol nitrate ray-level simulation explosive mimics |
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