CN106045859A - Method for preparing 2-nitropropane - Google Patents
Method for preparing 2-nitropropane Download PDFInfo
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- CN106045859A CN106045859A CN201610507953.6A CN201610507953A CN106045859A CN 106045859 A CN106045859 A CN 106045859A CN 201610507953 A CN201610507953 A CN 201610507953A CN 106045859 A CN106045859 A CN 106045859A
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- Prior art keywords
- acetone
- nitropropane
- ammonia
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- hydrogen peroxide
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/16—Separation; Purification; Stabilisation; Use of additives
Abstract
The invention discloses a method for preparing 2-nitropropane, and relates to the technical field of organic compound synthesis. The method comprises the following steps: enabling acetone, ammonia gas or ammonia water, hydrogen peroxide, a solvent and a catalyst to contact, heating till the reaction temperature of 30-100 DEG C, and controlling the reaction pressure to 0.1-0.2MPa to react, thereby obtaining 2-nitropropane, wherein the catalyst is a TS-1 titanium silicalite molecular sieve; the solvent is water; the mole ratio of acetone to ammonia gas or ammonia water is 1:(1-3); the mole ratio of acetone to hydrogen peroxide is 1:(0.5-2); and the mass ratio of acetone to the catalyst is 1:(0.2-0.4). The method disclosed by the invention has the advantages that the conversion rate of acetone is high and the selectivity of 2-nitropropane is good; the method is simple in reaction process, gentle in reaction condition, environment-friendly and easy in industrial production; and development of environment-friendly chemicals is promoted.
Description
Technical field
The present invention relates to organic compound synthesis technical field.
Background technology
2-nitropropane is used as ethylene and the special solvent of epoxy coating, rocket fuel, vapour oil additive etc., also
For organic synthesis.This product has the strongest solvability, is the fine solvent of various cellulose derivative, vinyl etc.,
Also serve as the solvent of wax, fat, dyestuff etc., the lubricant of ground pigment, and the cleaning of cotton goods and mordant.
About the preparation method of 2-nitropropane, it it is primarily now propane nitrification process.Reaction tower to 430-450 DEG C third
Alkane gas blowout note 75% nitric acid, propane is 5:1 with the mol ratio of nitric acid.Products obtained therefrom is nitromethane 10%-30%, nitroethane
20%-25%, 1-nitropropane 25%, 2-nitropropane 40%.These product also can obtain through propylene nitrification.The method course of reaction high temperature
High pressure, separation difficulty, environmental pollution is serious.
Summary of the invention
The technical problem to be solved in the present invention is to provide a kind of method preparing 2-nitropropane, and the method has acetone
The advantage that conversion ratio is high, the selectivity of 2-nitropropane is high, course of reaction is simple, and reaction condition is gentle, environmental friendliness, it is easy to work
Industry metaplasia is produced, and promotes the development of Green Chemistry.
For solving above-mentioned technical problem, the technical solution used in the present invention is: a kind of method preparing 2-nitropropane,
Comprise the following steps: acetone, ammonia or ammonia, hydrogen peroxide, solvent are contacted with catalyst, heating, reaction temperature 30～100
DEG C, reaction pressure 0.1～0.2MPa, react, obtain 2-nitropropane；Catalyst is TS-1 HTS；Solvent is
Water；Acetone is 1:1-3 with the mol ratio of ammonia or ammonia；Acetone is 1:0.5～2 with the mol ratio of hydrogen peroxide；Acetone and catalysis
The mass ratio of agent is 1:0.2～0.4.
Preferably, reaction temperature is 40～80 DEG C.
Preferably, the response time is 4～10 hours.
Preferably, the mass ratio of aqueous solvent and acetone is 1～3.5:1.
Preferably, acetone is 1:1-2.5 with the mol ratio of ammonia or ammonia；Acetone is 1:0.8 with the mol ratio of hydrogen peroxide
～2.
Preferably, reaction by-product acetone oxime.
Preferably, after reaction terminates, first reactant liquor rectification, distillate layering, last water washed reservoir are obtained product 2-nitre
Base propane.
Prior art " optimization of titanium silicon-1 molecular sieve catalytic acetone amine oxidation reaction condition " (Nanjing University of Technology's journal (from
So science version), in July, 2009 volume 31 the 4th phase: 74-78) investigate titanium silicon-1 molecular sieve (TS-1) catalysis acetone amine oxidative synthesis
The reaction condition of acetone oxime.It is the research prepared for acetone oxime, and process conditions, technological parameter etc. are carried out excellent by the present invention
Changing, creatively proposed as principal product by 2-nitropropane, the selectivity of 2-nitropropane is more than 50%, it is thus achieved that 2-nitre
The new applicable industrialized synthetic method of base propane, and the acetone oxime of by-product high value.
Use and have the beneficial effects that produced by technique scheme:
(1) the inventive method has the advantage that the conversion ratio selectivity high, 2-nitropropane of acetone is high, the choosing of 2-nitropropane
Selecting property is more than 50%, and course of reaction is simple, and reaction condition is gentle, and environmental friendliness, it is easy to industrialized production promotes greenization
The development learned；
(2) acetone oxime of the inventive method by-product high value.
Detailed description of the invention
Below by way of specific embodiment, preparation and the application of the present invention are described in further detail.
Wherein in the conversion ratio (%) of acetone=(mole of the mole of the middle acetone that feeds intake-unreacted acetone)/feed intake
Mole * 100 of acetone；
Mole * 100 of the mole/acetone total conversion of 2-nitropropane in selectivity (the %)=product of 2-nitropropane.
Embodiment 1
The synthetic reaction of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Gas chromatogram
Detection analysis result shows: the conversion ratio of acetone is 99%, and the selectivity of 2-nitropropane is 58%, and the selectivity of acetone oxime is
40%。
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, at ambient pressure, rectification 2-nitropropane reactant liquor, reflux ratio 2:1,70 DEG C～90 DEG C is 2-nitro
Propane distillate, layering, water washed reservoir obtain the 2-nitropropane that product is 99%, the response rate 90%；90 DEG C～98 DEG C is acetone oxime
Distillate, the response rate 95%, purity is 95%, and content is the aqueous solution of 40%.
Embodiment 2
The synthetic reaction (reduction reaction temperature) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 60 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection is analyzed
Result shows: the conversion ratio of acetone is 95%, and the selectivity of 2-nitropropane is 50%, and the selectivity of acetone oxime is 45%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 3
The synthetic reaction (liter high reaction temperature) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 80 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection is analyzed
Result shows: the conversion ratio of acetone is 99%, and the selectivity of 2-nitropropane is 59%, and the selectivity of acetone oxime is 25%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 4
The synthetic reaction (increasing the amount of ammonia) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 3:1,1.6:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection is analyzed
Result shows: the conversion ratio of acetone is 99%, and the selectivity of 2-nitropropane is 40%, and the selectivity of acetone oxime is 46%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 5
The synthetic reaction (reducing the amount of hydrogen peroxide) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.2:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection is analyzed
Result shows: the conversion ratio of acetone is 90%, and the selectivity of 2-nitropropane is 40%, and the selectivity of acetone oxime is 50%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 6
The synthetic reaction (increasing the amount of hydrogen peroxide) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,2:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Knot is analyzed in detection
Fruit shows: the conversion ratio of acetone is 98%, and the selectivity of 2-nitropropane is 45%, and the selectivity of acetone oxime is 30%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 7
The synthetic reaction (increasing the response time) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:3.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 10 hours, and the pressure of reaction system is normal pressure.Detection point
Analysis result shows: the conversion ratio of acetone is 99%, and the selectivity of 2-nitropropane is 56%, and the selectivity of acetone oxime is 40%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 8
The synthetic reaction (reducing the response time) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and dioxygen
Water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 6 hours, and the pressure of reaction system is normal pressure.Detection is analyzed
Result shows: the conversion ratio of acetone is 90%, and the selectivity of 2-nitropropane is 50%, and the selectivity of acetone oxime is 40%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 9
The synthetic reaction (reducing the amount of catalyst) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2.0:0.25 in mass ratio are added reactor, by above-mentioned reactant
System's heating, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), and ammonia is with double
Oxygen water is respectively 2:1,1.6:1 with the mol ratio of acetone, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection point
Analysis result shows: the conversion ratio of acetone is 80 %, and the selectivity of 2-nitropropane is 30%, and the selectivity of acetone oxime is 50%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 10
The synthetic reaction (increasing the amount of catalyst) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2:0.4 in mass ratio are added reactor, above-mentioned reaction system is added
Heat, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 30 wt %), ammonia and hydrogen peroxide
Being respectively 2:1,1.6:1 with the mol ratio of acetone, the response time is 8 hours, and the pressure of reaction system is normal pressure.Knot is analyzed in detection
Fruit shows: the conversion ratio of acetone is 99.5%, and the selectivity of 2-nitropropane is 59 %, and the selectivity of acetone oxime is 37 %.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 11
The synthetic reaction (changing the concentration of hydrogen peroxide) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:2:0.3 in mass ratio are added reactor, above-mentioned reaction system is added
Heat, reaction temperature is 70 DEG C, dropping ammonia (containing ammonia 25wt%) and hydrogen peroxide (containing hydrogen peroxide 50wt%), ammonia and hydrogen peroxide and
The mol ratio of acetone is respectively 2:1,1.6:1, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection analysis result
Showing: the conversion ratio of acetone is 97%, the selectivity of 2-nitropropane is 50%, and the selectivity of acetone oxime is 42%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
Embodiment 12
The synthetic reaction (ammonia changes ammonia into) of a, 2-nitropropane
Acetone, water and catalyst TS-1 HTS 1:3.5:0.3 in mass ratio are added reactor, by above-mentioned reaction system
Heating, reaction temperature is 70 DEG C, is passed through rubbing of ammonia and hydrogen peroxide (containing hydrogen peroxide 50wt%), ammonia and hydrogen peroxide and acetone
You are ratio respectively 2:1,1.6:1, and the response time is 8 hours, and the pressure of reaction system is normal pressure.Detection analysis result shows: third
The conversion ratio of ketone is 98.9 %, and the selectivity of 2-nitropropane is 55 %, and the selectivity of acetone oxime is 40%.
The purification of b, 2-nitropropane
After above-mentioned reaction terminates, it is 2-nitro third that the layering of rectification 2-nitropropane reactant liquor, distillate, water washed reservoir obtain product
Alkane, with embodiment 1.
The inventive method has the advantage that the conversion ratio selectivity high, 2-nitropropane of acetone is high, 2-nitropropane
Selectivity is more than 50%, and course of reaction is simple, and reaction condition is gentle, and environmental friendliness, it is easy to industrialized production promotes green
The development of chemistry；And the acetone oxime of by-product high value.
Claims (7)
1. the method preparing 2-nitropropane, it is characterised in that comprise the following steps:
Acetone, ammonia or ammonia, hydrogen peroxide, solvent are contacted with catalyst, heating, reaction temperature 30～100 DEG C, reaction pressure
0.1～0.2MPa, react, obtain 2-nitropropane；
Described catalyst is TS-1 HTS；Solvent is water；
Acetone is 1:1-3 with the mol ratio of ammonia or ammonia；Acetone is 1:0.5～2 with the mol ratio of hydrogen peroxide；Acetone and catalysis
The mass ratio of agent is 1:0.2～0.4.
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that reaction temperature is 40～80
℃。
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that the response time is 4～10
Hour.
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that aqueous solvent and the matter of acetone
Amount ratio is 1～3.5:1.
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that acetone and ammonia or ammonia
Mol ratio be 1:1-2.5；Acetone is 1:0.8～2 with the mol ratio of hydrogen peroxide.
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that reaction by-product acetone oxime.
A kind of method preparing 2-nitropropane the most according to claim 1, it is characterised in that after reaction terminates, first will
Reactant liquor rectification, distillate layering, last water washed reservoir obtain product 2-nitropropane.
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Cited By (10)
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| CN106831486A (en) * | 2017-03-03 | 2017-06-13 | 山东省化工研究院 | A kind of process for synthesizing ketoxime |
| CN106986772A (en) * | 2017-04-06 | 2017-07-28 | 宁波四明化工有限公司 | The synthetic method of 2 nitropropanes |
| CN107311128A (en) * | 2017-07-05 | 2017-11-03 | 郑州大学 | A kind of method for preparing hydroxylamine hydrochloride |
| CN107641084A (en) * | 2016-07-22 | 2018-01-30 | 北京旭阳科技有限公司 | A kind of method for producing nitroparaffins co-production ketoxime |
| CN107721860A (en) * | 2017-10-11 | 2018-02-23 | 中国科学院成都有机化学有限公司 | A kind of preparation method of nitroparaffins compound |
| CN110003013A (en) * | 2019-03-26 | 2019-07-12 | 山东理工大学 | Catalytic distillation prepares the green method of nitroparaffins |
| CN110511126A (en) * | 2019-09-25 | 2019-11-29 | 山东省化工研究院 | The method of by-product nitroparaffins is handled in a kind of ammoxidation oximation reaction of TS-1 catalysis |
| CN112321435A (en) * | 2020-11-03 | 2021-02-05 | 中触媒新材料股份有限公司 | Method for continuously synthesizing 2-nitropropane by adopting slurry bed |
| CN115557840A (en) * | 2022-11-04 | 2023-01-03 | 浙江新化化工股份有限公司 | Preparation method of 2-nitropropane and catalyst used in preparation method |
| CN115845915A (en) * | 2021-09-24 | 2023-03-28 | 北京旭阳科技有限公司 | Modified titanium-silicon catalyst, preparation method thereof and method for preparing nitroalkane by using same |
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| CN107641084A (en) * | 2016-07-22 | 2018-01-30 | 北京旭阳科技有限公司 | A kind of method for producing nitroparaffins co-production ketoxime |
| CN106831486A (en) * | 2017-03-03 | 2017-06-13 | 山东省化工研究院 | A kind of process for synthesizing ketoxime |
| CN106986772A (en) * | 2017-04-06 | 2017-07-28 | 宁波四明化工有限公司 | The synthetic method of 2 nitropropanes |
| CN106986772B (en) * | 2017-04-06 | 2019-01-18 | 宁波四明化工有限公司 | The synthetic method of 2- nitropropane |
| CN107311128A (en) * | 2017-07-05 | 2017-11-03 | 郑州大学 | A kind of method for preparing hydroxylamine hydrochloride |
| CN107721860A (en) * | 2017-10-11 | 2018-02-23 | 中国科学院成都有机化学有限公司 | A kind of preparation method of nitroparaffins compound |
| CN110003013A (en) * | 2019-03-26 | 2019-07-12 | 山东理工大学 | Catalytic distillation prepares the green method of nitroparaffins |
| CN110003013B (en) * | 2019-03-26 | 2021-11-05 | 山东理工大学 | Green method for preparing nitroalkane by catalytic distillation |
| CN110511126A (en) * | 2019-09-25 | 2019-11-29 | 山东省化工研究院 | The method of by-product nitroparaffins is handled in a kind of ammoxidation oximation reaction of TS-1 catalysis |
| CN110511126B (en) * | 2019-09-25 | 2022-09-23 | 山东省化工研究院 | Method for treating byproduct nitroalkane in ammoxidation oximation reaction catalyzed by TS-1 |
| CN112321435A (en) * | 2020-11-03 | 2021-02-05 | 中触媒新材料股份有限公司 | Method for continuously synthesizing 2-nitropropane by adopting slurry bed |
| CN112321435B (en) * | 2020-11-03 | 2022-06-03 | 中触媒新材料股份有限公司 | Method for continuously synthesizing 2-nitropropane by adopting slurry bed |
| CN115845915A (en) * | 2021-09-24 | 2023-03-28 | 北京旭阳科技有限公司 | Modified titanium-silicon catalyst, preparation method thereof and method for preparing nitroalkane by using same |
| CN115557840A (en) * | 2022-11-04 | 2023-01-03 | 浙江新化化工股份有限公司 | Preparation method of 2-nitropropane and catalyst used in preparation method |
| CN115557840B (en) * | 2022-11-04 | 2023-11-10 | 浙江新化化工股份有限公司 | Preparation method of 2-nitropropane and catalyst used in preparation method |
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Application publication date: 20161026 |