CN110845373A - Method for continuously preparing 2-nitro-4-methylsulfonyl toluene - Google Patents
Method for continuously preparing 2-nitro-4-methylsulfonyl toluene Download PDFInfo
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- CN110845373A CN110845373A CN201911201477.5A CN201911201477A CN110845373A CN 110845373 A CN110845373 A CN 110845373A CN 201911201477 A CN201911201477 A CN 201911201477A CN 110845373 A CN110845373 A CN 110845373A
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- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Abstract
The invention discloses a method for continuously preparing 2-nitro-4-methylsulfonyl toluene, wherein a reaction device comprises n stages of nitrification stay kettles which are sequentially connected in series, and a stirring device is arranged on each stage of nitrification stay kettle; dissolving p-methylsulfonyl toluene in concentrated sulfuric acid to prepare a raw material solution A; the temperature in each stage of nitration staying kettle is maintained at the reaction temperature, and the nitration staying kettles are all started to stir, the prepared raw material solution A and the nitrating acid mixture are mixed and flow from the first stage nitration staying kettle to the nth stage nitration staying kettle in a continuous feeding mode, reaction liquid flowing out of the nth stage nitration staying kettle is collected, and the collected reaction liquid is subjected to post-treatment to obtain a 2-nitro-4-methylsulfonyl toluene product. The method can realize continuous industrial production of the 2-nitro-4-methylsulfonyl toluene, reduces manual operation, can accurately control the raw material input ratio, the raw material input amount and the reaction time, and is safer and more reliable in the industrial production process.
Description
Technical Field
The invention relates to a method for continuously preparing 2-nitro-4-methylsulfonyl toluene.
Background
2-nitro-4-methylsulfonyltoluene is an important intermediate for synthesizing herbicide mesotrione, is also an important raw material for synthesizing chemical intermediate 2-nitro-4-methylsulfonylbenzoic acid, and is also used as medicine and dye
The intermediate is insoluble in water, ethanol and ether, is easily soluble in solvents such as acetone, chloroform and ethyl acetate, and is white powdery solid in appearance.
At present, the industrial production of the 2-nitro-4-methylsulfonyl toluene is carried out in an intermittent mode, the participation times of workers in the production process are more, repeated feeding, reaction and discharging are needed when batch reaction does not occur, errors are easily caused in operation, the production process cannot be well controlled, and the production cost is high.
Disclosure of Invention
Aiming at the technical problems in the prior art, the invention aims to provide a method for continuously preparing 2-nitro-4-methylsulfonyl toluene.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that a reaction device for continuously preparing the 2-nitro-4-methylsulfonyl toluene comprises n stages of nitrification stay kettles which are sequentially connected in series, and a stirring device for stirring liquid in each stage of nitrification stay kettle is arranged on each stage of nitrification stay kettle; dissolving p-methylsulfonyl toluene in concentrated sulfuric acid to prepare a raw material solution A for later use; the temperature in each stage of nitration staying kettle is maintained at the reaction temperature, and the nitration staying kettles are all started to stir, the prepared raw material solution A and the nitrating acid mixture are mixed and flow from the first stage nitration staying kettle to the nth stage nitration staying kettle in a continuous feeding mode, reaction liquid flowing out of the nth stage nitration staying kettle is collected, and the collected reaction liquid is subjected to post-treatment to obtain a 2-nitro-4-methylsulfonyl toluene product. The structural schematic diagram of the reaction device for continuously preparing the 2-nitro-4-methylsulfonyl toluene by using the n-stage nitrification stay kettles which are sequentially connected in series is shown in figure 1, and the multistage nitrification stay kettles are sequentially connected in series for reaction, so that the stay time of the nitrification reaction is increased, and the reaction is more thorough.
Furthermore, in order to strengthen the nitration reaction process and reduce the series stage number of the nitration retention kettle, the reaction device for continuously preparing the 2-nitro-4-methylsulfonyl toluene further comprises a mixing pump, a circulating pump and a discharge pump, wherein a liquid outlet of the mixing pump is connected with a liquid inlet at the top of the first-stage nitration retention kettle through a pipeline, a liquid outlet at the bottom of the first-stage nitration retention kettle is connected with a liquid inlet of the mixing pump through a pipeline through the circulating pump, and partial internal circulation of reaction liquid is formed; the middle liquid outlets of other nitrification staying kettles except the nth nitrification staying kettle are connected with the top liquid inlet of the next adjacent nitrification staying kettle through pipelines, and the bottom liquid outlet of the nth nitrification staying kettle is connected with the discharge pump through a pipeline so as to pump out reaction liquid in the nth nitrification staying kettle; control valves are arranged on the corresponding pipelines; the raw material solution A and the mixture of the nitrating acid are conveyed into a mixing pump together and mixed and reacted by the mixing pump, and then flow into a first-stage nitration retention kettle from a top inlet of the first-stage nitration retention kettle to be stirred and reacted; meanwhile, the reaction liquid in the first-stage nitration retention kettle flows out in two ways, one way returns to the mixing pump again through the circulating pump to carry out repeated nitration reaction, the other way flows from the second-stage nitration retention kettle to the nth-stage nitration retention kettle in a continuous feeding mode, and the reaction liquid in the nth-stage nitration retention kettle is pumped out through the discharge pump and then is post-treated to obtain the 2-nitro-4-methylsulfonyl toluene product.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the mass concentration of the concentrated sulfuric acid is 75-98%, and the preferred mass concentration is 80%.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the nitrating acid mixture is a mixture of concentrated nitric acid and concentrated sulfuric acid, and the mass concentration of the concentrated nitric acid in the nitrating acid mixture is 65-100%, preferably 80%.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the feeding mass ratio of the p-methylsulfonyl toluene to concentrated nitric acid in a mixture of concentrated sulfuric acid and nitrating acid is 1: 1-5: 0.35-0.6, and preferably 1: 2: 0.42.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that n is an integer of 2-8, preferably an integer of 4-6.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the reaction temperature is controlled to be-5-80 ℃, and preferably 15 ℃.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the reaction solution is subjected to post-treatment by steps of recrystallization, centrifugation and drying.
The method for continuously preparing the 2-nitro-4-methylsulfonyl toluene is characterized in that the solvent adopted by recrystallization is water.
Compared with the prior art, the invention has the following beneficial effects:
1) the method can realize continuous industrial production of the 2-nitro-4-methylsulfonyl toluene, wherein the methylsulfonyl toluene, the concentrated sulfuric acid and the concentrated nitric acid firstly flow into the mixing pump to carry out forced mixing reaction (forced mixing process, reaction speed is higher), the reaction liquid flowing out of the mixing pump flows into n stages of nitration staying kettles which are connected in series in sequence to be stirred, and part of the reaction liquid in the first stage nitration staying kettle flows back into the mixing pump to continue reaction, and the process has the following two advantages that the arrangement of the 1 and n stages of nitration staying kettles which are connected in series in sequence increases the reaction time, so that the nitration reaction is more thorough; 2. it is easy to remove a large amount of heat generated by the reaction, avoid overheating the reaction temperature and improve the safety of the reaction.
2) The structural schematic diagram of the device for continuously preparing the 2-nitro-4-methylsulfonyl toluene is shown in figure 1 or figure 2, the production line with the structure shown in figure 1 or figure 2 is adopted, more control instruments can be introduced, DCS control is adopted, industrial automatic control of the 2-nitro-4-methylsulfonyl toluene is achieved, manual operation is reduced, the raw material input ratio, the raw material input amount and the reaction time can be accurately controlled, and the industrial production process is safer and more reliable.
Drawings
FIG. 1 is a schematic structural diagram of a device for continuously preparing 2-nitro-4-methylsulfonyl toluene according to the present invention;
FIG. 2 is a second schematic structural diagram of an apparatus for continuously preparing 2-nitro-4-methylsulfonyl toluene according to the present invention;
in the figure: a-mixing pump, b-circulating pump, c-discharging pump, 1-first stage nitration staying kettle, 2-second stage nitration staying kettle, 3-third stage nitration staying kettle and 4-fourth stage nitration staying kettle.
Detailed Description
The present invention is further illustrated by the following examples, which should not be construed as limiting the scope of the invention.
Example 1:
the schematic structural diagram of the reaction device for continuously preparing 2-nitro-4-methylsulfonyltoluene in this example 1 is shown in fig. 2. As can be seen from FIG. 2, the reaction device comprises 4 stages of nitrification retention kettles, a mixing pump a, a circulating pump b and a discharge pump c which are connected in series in sequence. The liquid outlet of the mixing pump a is connected with the top liquid inlet of the first-stage nitrification reactor 1 through a pipeline, and the bottom liquid outlet of the first-stage nitrification reactor 1 is connected with the liquid inlet of the mixing pump a through a circulating pump b through a pipeline to form partial internal circulation of the reaction liquid. The middle liquid outlet of the first stage nitrification staying kettle 1 is connected with the top liquid inlet of the second stage nitrification staying kettle 2 through a pipeline, the middle liquid outlet of the second stage nitrification staying kettle 2 is connected with the top liquid inlet of the third stage nitrification staying kettle 3 through a pipeline, the middle liquid outlet of the third stage nitrification staying kettle 3 is connected with the top liquid inlet of the fourth stage nitrification staying kettle 4 through a pipeline, so that 4 stages of nitrification staying kettles which are sequentially connected in series are formed, and control valves are arranged on the corresponding pipelines;
dissolving p-methylsulfonyl toluene in concentrated sulfuric acid with the mass concentration of 80%, and preparing a raw material solution A for later use;
the raw material solution A and a nitrating acid mixture (the mass concentration of concentrated nitric acid in the nitrating acid mixture is 80%) are conveyed into a mixing pump a together, are mixed and react by the mixing pump a (the feeding mass ratio of the methyl sulfonyl toluene, the concentrated sulfuric acid and the concentrated nitric acid is 1: 2: 0.5), and flow into a first-stage nitration retention kettle 1 from a top inlet of the first-stage nitration retention kettle 1 to be stirred and reacted; meanwhile, the reaction liquid in the first-stage nitration retention kettle 1 flows out in two ways, one way returns to the mixing pump a again through the circulating pump b to carry out repeated nitration reaction, the other way flows to the fourth-stage nitration retention kettle from the second-stage nitration retention kettle 2 in a continuous feeding mode, and the reaction liquid in the fourth-stage nitration retention kettle is pumped out through the discharge pump c, recrystallized by an aqueous solvent, centrifuged and dried to prepare the 2-nitro-4-methylsulfonyl toluene product. Wherein the reaction temperature is controlled to be about 15-20 ℃, and the total residence time of the reaction liquid in the mixing pump a and the nitrification retention kettles with 4 stages connected in series in sequence is about 2 h.
By adopting the production process, when the reaction is basically complete (namely the conversion rate of the p-methylsulfonyl toluene reaches more than 98 percent), the molar yield of the 2-nitro-4-methylsulfonyl toluene product can reach more than 90 percent. The quality indexes of the finally prepared 2-nitro-4-methylsulfonyl toluene product are as follows: the mass fraction of the 2-nitro-4-methylsulfonyl toluene is more than or equal to 99 percent.
Example 2:
the schematic structural diagram of the reaction device for continuously preparing 2-nitro-4-methylsulfonyltoluene in this example 2 is shown in fig. 1. As can be seen from FIG. 1, the reaction device comprises 4 stages of nitrification stay kettles and discharge pumps c which are connected in series in sequence. The middle liquid outlet of the first stage nitrification staying kettle 1 is connected with the top liquid inlet of the second stage nitrification staying kettle 2 through a pipeline, the middle liquid outlet of the second stage nitrification staying kettle 2 is connected with the top liquid inlet of the third stage nitrification staying kettle 3 through a pipeline, the middle liquid outlet of the third stage nitrification staying kettle 3 is connected with the top liquid inlet of the fourth stage nitrification staying kettle 4 through a pipeline, so that 4 stages of nitrification staying kettles which are sequentially connected in series are formed, and control valves are arranged on the corresponding pipelines;
dissolving p-methylsulfonyl toluene in concentrated sulfuric acid with the mass concentration of 80%, and preparing a raw material solution A for later use;
the raw material solution A and the nitrating acid mixture (the mass concentration of the concentrated nitric acid in the nitrating acid mixture is 80%) flow into the first-stage nitration retention kettle 1 from the top inlet of the first-stage nitration retention kettle 1 to carry out stirring reaction (the feeding mass ratio of the p-methylsulfonyl toluene, the concentrated sulfuric acid and the concentrated nitric acid is 1: 2: 0.5), flow from the first-stage nitration retention kettle 1 to the fourth-stage nitration retention kettle in a continuous feeding mode, and the reaction liquid in the fourth-stage nitration retention kettle is pumped out by a discharge pump c and then is recrystallized, centrifuged and dried by using an aqueous solvent to prepare the 2-nitro-4-methylsulfonyl toluene product. Wherein the reaction temperature is controlled to be about 15-20 ℃, and the total residence time of the reaction liquid in 4 stages of nitration residence kettles which are connected in series in sequence is about 4 h.
By adopting the production process, the conversion rate of the p-methylsulfonyl toluene is about 96.3 percent, and the molar yield of the 2-nitro-4-methylsulfonyl toluene product can reach about 88.6 percent.
It can be seen that the feed flow rate of the reaction liquid in example 2 is slower compared to the preparation process of example 1. The reaction results of the comparative example 1 and the example 2 show that the method of the invention can be used for continuously preparing the 2-nitro-4-methylsulfonyl toluene and can obtain better reaction effect. Compared with the embodiment 2, the method in the embodiment 1 has better reaction effect and greatly shortens the reaction time, which is probably because the mixing pump a can effectively strengthen the nitration reaction process when the reaction device in the embodiment 1 is used for continuously preparing the 2-nitro-4-methylsulfonyl toluene, the retention time of the reaction liquid in the mixing pump a is shorter, the reaction liquid after being forcibly mixed by the mixing pump a flows into the nitration retention kettle, a large amount of heat generated by the reaction is easy to remove, and the overheating of the reaction temperature is avoided.
Example 3:
the schematic structural diagram of the reaction apparatus for continuously preparing 2-nitro-4-methylsulfonyltoluene in this example 3 is shown in fig. 2. The reaction process is repeated as in example 1, except that the reaction temperature is controlled to be about 0-5 ℃, the conversion rate of the p-methylsulfonyltoluene is about 93.5 percent and the molar yield of the 2-nitro-4-methylsulfonyltoluene product can reach about 85.7 percent by adopting the production process.
Example 4:
the schematic structural diagram of the reaction apparatus for continuously preparing 2-nitro-4-methylsulfonyltoluene in this example 4 is shown in fig. 2. The reaction process is repeated as in example 1, except that the reaction temperature is controlled to be about 65-70 ℃, the conversion rate of the methyl sulfonyl toluene is more than 94.8 percent by adopting the production process, and the molar yield of the 2-nitro-4-methyl sulfonyl toluene product can reach about 83.2 percent.
The statements in this specification merely set forth a list of implementations of the inventive concept and the scope of the present invention should not be construed as limited to the particular forms set forth in the examples.
Claims (9)
1. A method for continuously preparing 2-nitro-4-methylsulfonyl toluene is characterized in that a reaction device for continuously preparing 2-nitro-4-methylsulfonyl toluene comprises n stages of nitrification stay kettles which are sequentially connected in series, and a stirring device for stirring the liquid in each stage of nitrification stay kettle is arranged on each stage of nitrification stay kettle;
dissolving p-methylsulfonyl toluene in concentrated sulfuric acid to prepare a raw material solution A for later use;
the temperature in each stage of nitration staying kettle is maintained at the reaction temperature, and the nitration staying kettles are all started to stir, the prepared raw material solution A and the nitrating acid mixture are mixed and flow from the first stage nitration staying kettle (1) to the nth stage nitration staying kettle in a continuous feeding mode, reaction liquid flowing out of the nth stage nitration staying kettle is collected, and the collected reaction liquid is subjected to post-treatment to obtain a 2-nitro-4-methylsulfonyl toluene product.
2. The method for continuously preparing 2-nitro-4-methylsulfonyl toluene according to claim 1, wherein the reaction apparatus for continuously preparing 2-nitro-4-methylsulfonyl toluene further comprises a mixing pump (a), a circulating pump (b) and a discharging pump (c), wherein a liquid outlet of the mixing pump (a) is connected with a liquid inlet at the top of the first-stage nitrification staying still (1) through a pipeline, a liquid outlet at the bottom of the first-stage nitrification staying still (1) is connected with a liquid inlet of the mixing pump (a) through the circulating pump (b) through a pipeline, so as to form partial internal circulation of the reaction liquid;
the middle liquid outlets of other stages of nitrification stay kettles except the nth stage of nitrification stay kettle are connected with the top liquid inlet of the next adjacent stage of nitrification stay kettle through pipelines, and the bottom liquid outlet of the nth stage of nitrification stay kettle is connected with the discharge pump (c) through a pipeline so as to pump out reaction liquid in the nth stage of nitrification stay kettle; control valves are arranged on the corresponding pipelines;
the raw material solution A and the mixture of the nitrating acid are conveyed into a mixing pump (a) together and are mixed and reacted by the mixing pump (a), and then flow into the first-stage nitration retention kettle (1) from the top inlet of the first-stage nitration retention kettle (1) for stirring reaction; meanwhile, the reaction liquid in the first-stage nitrification retention kettle (1) flows out in two ways, one way returns to the mixing pump (a) again through the circulating pump (b) to carry out repeated nitrification reaction, the other way flows to the nth-stage nitrification retention kettle from the second-stage nitrification retention kettle (2) in a continuous feeding mode, and the reaction liquid in the nth-stage nitrification retention kettle is pumped out through the discharge pump (c) and then is subjected to post-treatment to obtain the 2-nitro-4-methylsulfonyl toluene product.
3. The method for continuously preparing 2-nitro-4-methylsulfonyl toluene according to claim 1, wherein the mass concentration of the concentrated sulfuric acid is 75% to 98%, preferably 80%.
4. The method for continuously preparing 2-nitro-4-methylsulfonyl toluene according to claim 1, wherein the nitrating acid mixture is a mixture of concentrated nitric acid and concentrated sulfuric acid, and the mass concentration of the concentrated nitric acid in the nitrating acid mixture is 65% to 100%, preferably 80%.
5. The method for continuously preparing 2-nitro-4-methylsulfonyl toluene according to claim 4, wherein the mass ratio of the p-methylsulfonyl toluene to the concentrated sulfuric acid to the concentrated nitric acid in the mixture of the nitrating acid is 1: 1-5: 0.35-0.6, preferably 1: 2: 0.42.
6. The method for continuously preparing 2-nitro-4-methylsulfonyltoluene according to claim 1, wherein n is an integer of 2 to 8, preferably an integer of 4 to 6.
7. The method for continuously preparing 2-nitro-4-methylsulfonyl toluene according to claim 1, wherein the reaction temperature is controlled at-5 to 80 ℃, preferably 15 ℃.
8. The method for continuously preparing 2-nitro-4-methylsulfonyltoluene according to claim 1, wherein the reaction solution is post-treated by recrystallization, centrifugation and drying.
9. The continuous preparation method of 2-nitro-4-methylsulfonyltoluene as claimed in claim 8, wherein the solvent used for recrystallization is water.
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