CN108707077A - The method for preparing TNT as raw material one-step method using nitrotoleune - Google Patents
The method for preparing TNT as raw material one-step method using nitrotoleune Download PDFInfo
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- CN108707077A CN108707077A CN201810572337.8A CN201810572337A CN108707077A CN 108707077 A CN108707077 A CN 108707077A CN 201810572337 A CN201810572337 A CN 201810572337A CN 108707077 A CN108707077 A CN 108707077A
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- tnt
- nitrotoleune
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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
- C07C201/08—Preparation of nitro compounds by substitution of hydrogen atoms by nitro groups
Abstract
The invention discloses a kind of methods preparing TNT as raw material one-step method using nitrotoleune, using para-nitrotoluene or ortho-methylnitrobenzene as raw material, smoke HNO3/ dense H2SO4Mixed system be nitrating agent, a step nitration reaction prepares 2,4,6-trinitrotoluene TNT, structural characterization carried out to it using fusing point, thin-layer chromatography, mass spectrum, liquid chromatogram.Smoke HNO is inquired into3/ dense H2SO4Mixed system the influence to product yield of ratio, feed way, dosage, optimize reaction condition.The present invention passes through obtains TNT by the nitrification synthesis of one step of raw material of nitrotoleune, avoids and generates a large amount of spent acid, the pollution environment that Hong Shui is brought, reduces reaction step and nitrify the energy of equipment belt, power consumption.
Description
Technical field
The present invention relates to a kind of methods preparing TNT as raw material one-step method using nitrotoleune, belong to explosive technology of preparing neck
Domain.
Background technology
2,4,6- trinitrotoluenes（TNT）It is a kind of high explosives, synthesizes for the first time within 1863.It is to be mixed through nitre sulphur by toluene
Acid nitrification mass production.Most of TNT produced both at home and abroad at present is mixed through nitre sulphur as raw material using toluene
Acid carries out three-stage nitration technique, and using the equipment of nine nitrification machines, i.e., toluene is nitrified into mononitrotoluene in one-stage nitration
（MNT）, mononitrotoluene includes：Ortho-methylnitrobenzene, para-nitrotoluene and meta-nitrotoluene；MNT is nitrified into two stage nitration
Dinitrotoluene (DNT)（DNT）；DNT is nitrified into trinitrotoluene in three-stage nitration（TNT）.It is exactly to use toluene through hair in short
The mixture of cigarette nitric acid and the concentrated sulfuric acid obtains the mixture of dinitro toluene isomers, then with fuming nitric aicd and containing SO3Hair
DNT mixtures are converted to TNT by the mixture of cigarette sulfuric acid, are finally refined again through sodium sulfite or other methods are refined and obtained.Three
The synthetic route of section nitrification is as follows：
In TNT preparation process, in nitrification, often a upper nitro, the concentration of its nitric acid are different toluene on phenyl ring.This
Process will produce red water, be a typical pollutant and waste in TNT production processes（Sun Rongkang, Ren Tesheng, Gao Huailin
It writes；Chemistry and technology Beijing of high explosive：National Defense Industry Press；1981.07 325-335；Nitro-compound explosive
It learns and technology Sun Rong Kang Dengbian weapon industries publishing house 1992.11,175-245）.With being constantly progressive for society, industrially
The shortcomings that widely used production technology, becomes increasingly conspicuous, and is mainly shown as：Generate asymmetric TNT（2,4,5-, 2,3,4-, 2,
3,6-, 2,3,5- and 3,4,5- trinitrotoluenes）, while also generating a large amount of pollutant, such as nitrogen oxides（NOx）And tetranitro
Methane（TNM）, for example, using traditional manufacturing method, often generate the TNT of double centner by will produce 0.5% TNM, these are dirty
Object is contaminated to need to remove, to prevent its welding, to cause damages to environment；A large amount of uses of strong acid cause environment serious
Harm, cannot be satisfied environmental economy sustainable development；In the industrial production, serious corrosion is produced now to shop equipment
As；The drastically heat release occurred in reaction process causes operation unstability, is easy that the safety accidents such as explosion occur in process of production；
When nitric acid excess, oxidation side reaction easily occurs, explosive decomposition, yield is caused to decline；There is no nitrification region selective, generates big
Unwanted organic isomers is measured, resource is caused largely to waste；The discharge of a large amount of spent acid, improves processing cost.
Invention content
The present invention is intended to provide a kind of method that TNT is prepared as raw material one-step method using nitrotoleune, and use mass spectrum, melt
Point, thin-layer chromatography, liquid chromatogram characterize its structure, optimize the reaction condition of synthesis.
The nitrotoleune used in the present invention includes para-nitrotoluene or ortho-methylnitrobenzene, right（It is adjacent）Nitrotoleune derives from
Toluene one-stage nitration product, process are isolated.It is mainly used to the reaction intermediate of synthesis of organic substance, para-nitrotoluene is used for two
A aspect：First, oxidation prepares paranitrobenzoic acid or paranitrobenzaldehyde, second is that catalytic hydrogenation generates paranitroanilinum.Adjacent nitre
Base toluene can prepare the organic intermediates such as metacresol, meta-aminotoluene.The present invention is kept away using nitrotoleune or ortho-methylnitrobenzene as raw material
The a large amount of spent acid of generation are exempted from, the pollution environment that Hong Shui is brought, the energy, the power for reducing reaction step and nitrification equipment belt disappear
Consumption.
The present invention uses the concentrated sulfuric acid with fuming nitric aicd for nitrating agent, with right（It is adjacent）Nitrotoleune is raw material, by a step nitre
It is combined to obtain TNT.
The present invention synthetic route be：
。
The present invention provides a kind of methods preparing TNT as raw material one-step method using nitrotoleune, include the following steps：
（1）Prepare nitration mixture：
Measure the H of 25-30ml2SO4（98%）In four-hole boiling flask, then measure 5-10ml HNO3（98%）In separatory funnel, just
20-40 DEG C of beginning temperature opens automatic stirrer and condensation reflux unit, by HNO3（98%）It is added drop-wise to H2SO4（98%）In, it keeps
Temperature is 40 ~ 50 DEG C；
Nitric acid, sulfuric acid mol ratio are respectively 1：2.5~4；
（2）Charging：
After nitration mixture is prepared, when temperature has downward trend, start to be slowly added to 4-9g para-nitrotoluene or ortho-methylnitrobenzene,
There is heating trend, maintains the temperature at 80 ~ 90 DEG C；Charging finishes, and has cooling trend；
（3）Reaction：
Start oil bath and be warming up to 90-140 DEG C, keeps the temperature 3-8h（Reaction time）, it is kept stirring, rotating speed 350-400r/min.
（4）Processing：
Start Temperature fall after completion of the reaction, be slowly stirred, be cooled to 20-60 DEG C, solution is poured into the cold water of 50-100ml,
Side bevelling stirring, has the smoke of gunpowder to emerge, and waits for that temperature drops to 30 DEG C, starts sand core and filters；Use 80-90 DEG C of hot water washed product extremely again
Product is put into evaporating dish by neutrality, is placed in 40-60 DEG C of drying box dry 5-10h.
In the above method, by HNO3（98%）It is added drop-wise to H2SO4（98%）In rate of addition be 0.5-2mL/min.
In the above method, the yield of TNT is 89-95%.
In the above method, it is preferable that reaction time 4h, reaction temperature are 110 ~ 115 DEG C, 98%H2SO4With 98%HNO3's
Molar ratio is 10:3.
As a kind of perferred technical scheme：The method that one-step method prepares TNT, includes the following steps：
（1）Measure the 98%H of 0.5mol2SO4In four-hole boiling flask, then measure the 98%HNO of 0.15mol3In separatory funnel, just
35 DEG C of beginning temperature opens automatic stirrer and condensation reflux unit, by 98%HNO3It is added drop-wise to 98%H2SO4In, it is 40 to keep temperature
~50℃；
（2）After nitration mixture is prepared, when temperature has downward trend, start to be slowly added to 0.05mol para-nitrotoluene or adjacent nitre
Base toluene has heating trend, maintains the temperature at 80 ~ 90 DEG C；
（3）Start oil bath and be warming up to 110-115 DEG C, reacts 4h；
（4）Start Temperature fall after completion of the reaction, be slowly stirred, be cooled to 40 DEG C, solution is poured into the cold water of 100ml, side
Bevelling stirs, and has the smoke of gunpowder to emerge, and waits for that temperature drops to 30 DEG C, starts sand core and filters；Again with 100 DEG C of hot water washed products into
Property, product is put into evaporating dish, dry 10h is placed in 60 DEG C of drying boxes, measures quality, the yield of TNT can reach
92.2%。
TNT is produced by the method for the invention, and the wastewater flow rate generated after reaction is few, and COD is low, right（It is adjacent）Nitro first
Methyl and nitro have positioning action in benzene, avoid and generate a variety of other dinitrotoluene (DNT)s（Such as 2,3- dinitrotoluene (DNT)s, 2,5- bis-
This four classes dinitrotoluene (DNT) of nitrotoleune, 3,4- dinitrotoluene (DNT)s and 3,5- dinitrotoluene (DNT)s）, reduce containing for tetranitromethane
Amount.
Beneficial effects of the present invention：
The present invention passes through obtains TNT by the nitrification synthesis of one step of raw material of nitrotoleune, avoids and generates a large amount of spent acid, Hong Shui is brought
Pollution environment the shortcomings that and reduce reaction step and nitrify the energy of equipment belt, power consumption.
Description of the drawings
Fig. 1 is influence diagram of the variation to TNT yields of reaction temperature.
Fig. 2 is influence diagram of the variation to TNT yields of nitric acid and concentrated sulfuric acid molar ratio.
Specific implementation mode
It is further illustrated the present invention below by embodiment, but is not limited to following embodiment.
The present invention provides the methods for preparing TNT as raw material one-step method using nitrotoleune, include the following steps：
（1）Prepare nitration mixture：
Measure the H of 25-30ml2SO4（98%）In four-hole boiling flask, then measure 5-10ml HNO3（98%）In separatory funnel, just
20-40 DEG C of beginning temperature opens automatic stirrer and condensation reflux unit, by HNO3（98%）It is added drop-wise to H2SO4（98%）In, it keeps
Temperature is 40 ~ 50 DEG C；
（2）Charging：
After nitration mixture is prepared, when temperature has downward trend, start to be slowly added to 4-9g para-nitrotoluene or ortho-methylnitrobenzene,
There is heating trend, maintains the temperature at 80-90 DEG C；Charging finishes, and has cooling trend；
（3）Reaction：
Start oil bath and be warming up to 90-140 DEG C, keeps the temperature 3-8h（Reaction time）, it is kept stirring, rotating speed 350-400r/min.
（4）Processing：
Start Temperature fall after completion of the reaction, be slowly stirred, be cooled to 20-60 DEG C, solution is poured into the cold water of 50-100ml,
Side bevelling stirring, has the smoke of gunpowder to emerge, and waits for that temperature drops to 30 DEG C, starts sand core and filters；Use 80-90 DEG C of hot water washed product extremely again
Product is put into evaporating dish by neutrality, is placed in 40-60 DEG C of drying box dry 5-10h.
Illustrate the method for one-step synthesis method TNT below by specific embodiment.
Embodiment 1：The method of one-step synthesis method TNT
The present embodiment has investigated influence of the reaction time to TNT yields：
It is 120 DEG C to take para-nitrotoluene 0.05mol, nitric acid 0.15mol, sulfuric acid 0.5mol, reaction temperature.Reaction time is respectively
3h, 4h, 5h, 6h, 7h, 8h.Influence of the reaction time to product is shown in Table 1.From table 1 it follows that the yield of product TNT with
The extension of time, it is constant after first increasing, it is best when reacting 4h.
Influence of 1 reaction time of table to TNT yields
The optimization in reaction time：Take para-nitrotoluene 0.05mol, HNO3：H2SO4=3:10, nitric acid 0.15mol, sulfuric acid 0.5mol,
Reaction temperature is 120 degree.Reaction time is respectively 3h, 4h, 5h, 6h, 7h, 8h.The product of 3h is mixture（Reaction does not complete）,
Other yield are all 89%, and when illustrating to react 4h, the reaction was complete.
Embodiment 2：The method of one-step synthesis method TNT
The present embodiment has investigated influence of the reaction temperature to TNT yields
Take para-nitrotoluene 0.05mol, HNO3：H2SO4=1：3.5, nitric acid 0.15mol, sulfuric acid 0.5mol, reaction time 4h.
Reaction temperature is respectively 100 DEG C, 110 DEG C, 120 DEG C, 130 DEG C, 140 DEG C.
Influence of the reaction temperature to product TNT such as Fig. 1.As seen from Figure 1, product yield first increases and reduces afterwards, 110 DEG C
When product yield highest.
The optimization of reaction temperature：Take para-nitrotoluene 0.05mol, HNO3：H2SO4=1：3.5, nitric acid 0.15mol, sulfuric acid
0.5mol, reaction time 4h.Reaction temperature is respectively 100 DEG C, 110 DEG C, 120 DEG C, 130 DEG C, 140 DEG C.Yield is respectively
90.8%, 92.2%, 89%, 89%, 86%.
Embodiment 3：The method of one-step synthesis method TNT
The present embodiment has investigated nitric acid and influence of the concentrated sulfuric acid molar ratio to TNT yields
It is 110 DEG C to take ortho-methylnitrobenzene 0.05mol, reaction time 4h, reaction temperature.Nitric acid-sulfuric acid matches（Molar ratio）Respectively
It is 1：2.5,1：3,1：3.5,1：4.Product yield n (NA)：N (SA) variations are as shown in Figure 2.Figure it is seen that target product
Yield is reduced afterwards as the increase of the concentrated sulfuric acid first increases, at n (NA)：n(SA)=1：Reach maximum when 3.5.
React nitric-sulfuric acid than optimization：Take ortho-methylnitrobenzene 0.05mol, reaction time 4h, reaction temperature 110
Degree.Nitric acid-sulfuric acid proportioning is respectively 1：2.5,1：3,1：3.5,1：4.Yield is respectively 87%, 89%, 92.2%, 89%.
Embodiment 4：
The present invention detects the technique waste water after reaction, is compared with former TNT production technologies, as a result such as the following table 2
It is shown：
Table 2
Produce TNT by the method for the invention, the wastewater flow rate generated after reaction is few, and COD is low, in nitrotoleune methyl and
Nitro has positioning action, avoids and generates a variety of dinitrotoluene (DNT)s（It will be free from 2,3- dinitrotoluene (DNT)s, 2,5- dinitro first
This four classes dinitrotoluene (DNT) of benzene, 3,4- dinitrotoluene (DNT)s and 3,5- dinitrotoluene (DNT)s）, reduce the content of tetranitromethane.
Claims (9)
1. the method for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：Using nitrotoleune as raw material, smoke
HNO3/ dense H2SO4Mixed system be nitrating agent, a step nitration reaction prepares 2,4,6-trinitrotoluene TNT；
The nitrotoleune includes para-nitrotoluene or ortho-methylnitrobenzene.
2. the method according to claim 1 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：Including
Following steps：
（1）Prepare nitration mixture：
Measure the H of 25-30ml2SO4In four-hole boiling flask, then measure 5-10mlHNO3In separatory funnel, initial temperature 20-40
DEG C, automatic stirrer and condensation reflux unit are opened, by HNO3It is added drop-wise to H2SO4In, it is 40 ~ 50 DEG C to keep temperature；
H2SO4For the concentrated sulfuric acid of 98% mass concentration, HNO3For the fuming nitric aicd of 98% mass concentration；Nitric acid, sulfuric acid mol ratio
Respectively 1：2.5~4；
（2）Charging：
After nitration mixture is prepared, when temperature has downward trend, start to be slowly added to 4-9g para-nitrotoluene or ortho-methylnitrobenzene,
There is heating trend, maintains the temperature at 80 ~ 90 DEG C；Charging finishes, and has cooling trend；
（3）Reaction：
Start oil bath and be warming up to 90-140 DEG C, reacts 3-8h, stirring, it is 350-400r/min to be kept stirring speed；
（4）Processing：
Start Temperature fall after completion of the reaction, be slowly stirred, be cooled to 20-60 DEG C, solution is poured into the cold water of 50-100ml,
Side bevelling stirring, has the smoke of gunpowder to emerge, and waits for that temperature drops to 30 DEG C, starts sand core and filters；Use 80-90 DEG C of hot water washed product extremely again
Product is put into evaporating dish by neutrality, is placed in 40-60 DEG C of drying box dry 5-10h.
3. the method according to claim 2 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：By HNO3
It is added drop-wise to H2SO4In rate of addition be 0.5-2mL/min.
4. the method according to claim 2 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：TNT's
Yield is 89-95%.
5. the method according to claim 2 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：Step
（3）In, oil bath is warming up to 110-115 DEG C, reaction time 4h.
6. the method according to claim 2 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：98%
H2SO4With 98%HNO3Molar ratio be 10:3.
7. the method according to claim 2 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：Including
Following steps：
（1）Measure the 98%H of 0.5mol2SO4In four-hole boiling flask, then measure the 98%HNO of 0.15mol3In separatory funnel, just
35 DEG C of beginning temperature opens automatic stirrer and condensation reflux unit, by 98%HNO3It is added drop-wise to 98%H2SO4In, it is 40 to keep temperature
~50℃；
（2）After nitration mixture is prepared, when temperature has downward trend, start to be slowly added to 0.05mol para-nitrotoluene or adjacent nitre
Base toluene has heating trend, maintains the temperature at 80 ~ 90 DEG C；
（3）Start oil bath and be warming up to 110 DEG C, reacts 4h；
（4）Start Temperature fall after completion of the reaction, be slowly stirred, be cooled to 40 DEG C, solution is poured into the cold water of 100ml, side
Bevelling stirs, and has the smoke of gunpowder to emerge, and waits for that temperature drops to 30 DEG C, starts sand core and filters；Again with 100 DEG C of hot water washed products into
Property, product is put into evaporating dish, dry 10h is placed in 60 DEG C of drying boxes.
8. the method according to claim 7 for preparing TNT as raw material one-step method using nitrotoleune, it is characterised in that：It will production
Quality is measured after object drying, the yield of TNT reaches 92.2%.
9. according to the method that claim 1 ~ 8 any one of them prepares TNT using nitrotoleune as raw material one-step method, feature exists
In：Waste water after reaction, wastewater flow rate is few, and COD is low, and methyl and nitro have positioning action in nitrotoleune, avoid life
At a variety of dinitrotoluene (DNT)s, reduce the content of tetranitromethane.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113371906A (en) * | 2021-05-31 | 2021-09-10 | 湖北东方化工有限公司 | Dinitrotoluene recovery device and process |
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Application publication date: 20181026 |