CN111362803A - Microchannel reaction process for continuously synthesizing 1-nitro mesitylene - Google Patents
Microchannel reaction process for continuously synthesizing 1-nitro mesitylene Download PDFInfo
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- CN111362803A CN111362803A CN201811588680.8A CN201811588680A CN111362803A CN 111362803 A CN111362803 A CN 111362803A CN 201811588680 A CN201811588680 A CN 201811588680A CN 111362803 A CN111362803 A CN 111362803A
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- reaction
- mesitylene
- solution
- nitric acid
- nitromesitylene
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 44
- PKPAWOQKSLPLBJ-UHFFFAOYSA-N 1,3,5-trimethyl-5-nitrocyclohexa-1,3-diene Chemical group [N+](=O)([O-])C1(CC(=CC(=C1)C)C)C PKPAWOQKSLPLBJ-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 claims abstract description 21
- 239000000463 material Substances 0.000 claims abstract description 18
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 16
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 15
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 15
- 230000035484 reaction time Effects 0.000 claims abstract description 15
- 239000000243 solution Substances 0.000 claims description 20
- PEWOKNPNVPZJCB-UHFFFAOYSA-N C(C)(=O)OC(C)=O.C1(=CC(=CC(=C1)C)C)C Chemical compound C(C)(=O)OC(C)=O.C1(=CC(=CC(=C1)C)C)C PEWOKNPNVPZJCB-UHFFFAOYSA-N 0.000 claims description 8
- 239000011259 mixed solution Substances 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000006185 dispersion Substances 0.000 claims description 4
- 239000012530 fluid Substances 0.000 claims description 2
- 239000012528 membrane Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000012546 transfer Methods 0.000 abstract description 8
- 239000002253 acid Substances 0.000 abstract description 5
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical group CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- SGHZXLIDFTYFHQ-UHFFFAOYSA-L Brilliant Blue Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C(=CC=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 SGHZXLIDFTYFHQ-UHFFFAOYSA-L 0.000 abstract description 2
- 239000000980 acid dye Substances 0.000 abstract description 2
- NNBFNNNWANBMTI-UHFFFAOYSA-M brilliant green Chemical compound OS([O-])(=O)=O.C1=CC(N(CC)CC)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](CC)CC)C=C1 NNBFNNNWANBMTI-UHFFFAOYSA-M 0.000 abstract description 2
- 239000000975 dye Substances 0.000 abstract description 2
- 238000004043 dyeing Methods 0.000 abstract description 2
- 238000002474 experimental method Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract description 2
- 239000000985 reactive dye Substances 0.000 abstract description 2
- NKLPQNGYXWVELD-UHFFFAOYSA-M coomassie brilliant blue Chemical compound [Na+].C1=CC(OCC)=CC=C1NC1=CC=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)N(CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=C1 NKLPQNGYXWVELD-UHFFFAOYSA-M 0.000 abstract 1
- GPFIZJURHXINSQ-UHFFFAOYSA-N acetic acid;nitric acid Chemical compound CC(O)=O.O[N+]([O-])=O GPFIZJURHXINSQ-UHFFFAOYSA-N 0.000 description 6
- 238000005265 energy consumption Methods 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000010924 continuous production Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- SCEKDQTVGHRSNS-UHFFFAOYSA-N 1,3,5-trimethyl-2-nitrobenzene Chemical group CC1=CC(C)=C([N+]([O-])=O)C(C)=C1 SCEKDQTVGHRSNS-UHFFFAOYSA-N 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- UHXQPQCJDDSMCB-UHFFFAOYSA-L disodium;3-[[9,10-dioxo-4-(2,4,6-trimethyl-3-sulfonatoanilino)anthracen-1-yl]amino]-2,4,6-trimethylbenzenesulfonate Chemical compound [Na+].[Na+].CC1=CC(C)=C(S([O-])(=O)=O)C(C)=C1NC(C=1C(=O)C2=CC=CC=C2C(=O)C=11)=CC=C1NC1=C(C)C=C(C)C(S([O-])(=O)=O)=C1C UHXQPQCJDDSMCB-UHFFFAOYSA-L 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Abstract
The invention discloses a microchannel reaction process for continuously synthesizing 1-nitromesitylene, wherein 1-nitromesitylene is a raw material of 2-aminomesitylene, 2-aminomesitylene is an intermediate of weak acid and reactive dye, and the dye synthesized by the microchannel reaction process is bright in color and good in level-dyeing property, such as weak acid brilliant blue R A W, reactive emerald green, reactive brilliant blue and the like. The method comprises the following steps: respectively injecting a mesitylene solution and a nitric acid solution into a feed inlet of the microchannel reactor by using a plunger metering pump, controlling the reaction time of the materials, keeping the reaction temperature of at least one part of modules at 40-180 ℃, receiving the materials at an outlet after passing through a plurality of reaction modules, and carrying out subsequent conventional subsequent treatment to obtain the 1-nitromesitylene. The process method of the invention utilizes the high-efficiency mass transfer and heat transfer efficiency of the microchannel reactor, effectively strengthens the mass transfer rate between materials, stabilizes the reaction temperature, greatly improves the safety and operability of the experiment, and is suitable for the continuous industrial production.
Description
Technical Field
The invention relates to a microchannel reaction process for continuously synthesizing 1-nitromesitylene.
Background
1-nitro-mesitylene is a raw material of 2-amino-mesitylene, 2-amino-mesitylene is an intermediate of weak acid and reactive dye, and the dye synthesized by the 2-nitro-mesitylene, such as weak acid brilliant blue RAW, reactive emerald green, reactive brilliant blue and the like, has bright color and good level-dyeing property. The synthetic literature reports about 1-nitromesitylene are less, the industry mainly adopts a mesitylene mixed acid nitration process at present, and the process has low production efficiency and high labor intensity. The process has a series of problems of large heat release amount, serious corrosion of mixed acid to a reaction kettle, long reaction time, serious material back mixing, high energy consumption and the like during reaction.
Compared with the conventional reactor, the microchannel reactor has the characteristics of large specific surface area, small volume, continuous process, easy amplification, good quick mixing effect, good heat transfer effect and the like, and has excellent mass transfer and heat transfer properties, which are applied to the experiment for synthesizing the 1-nitromesitylene, the mass transfer and the heat transfer effects of microreactors with different microstructures are different, so the yield of the 1-nitromesitylene is different according to the reactor. So far, no technical research and equipment technical report of 1-nitromesitylene synthesis reaction in a microchannel continuous reaction mode exists, and the invention provides a novel method for continuously producing 1-nitromesitylene by using a microchannel reactor.
Disclosure of Invention
The invention aims to provide an improved technology of a preparation process of 1-nitromesitylene. The improved process mainly takes mesitylene solution and nitric acid solution as initial raw materials, simultaneously leads the initial raw materials into a micro-channel reactor for reaction, and obtains products after subsequent treatment. The process has the characteristics of simple and convenient operation, low energy consumption, high safety and suitability for continuous industrial production.
The technical scheme of the invention is as follows:
a micro-channel reaction process for continuously synthesizing 1-nitromesitylene comprises the following steps: respectively and simultaneously injecting a mesitylene solution and a nitric acid solution into a feed inlet of a micro mixer by using a plunger pump, adjusting the pressure of a back pressure valve, controlling the reaction time of materials, and when a mixture flows from an inlet of the micro mixer to an outlet of the micro mixer, at least keeping the reaction temperature of at least one single fluid module at 40-180 ℃, receiving the materials at the outlet after the reaction of a plurality of modules, and obtaining the 1-nitromesitylene by conventional aftertreatment.
The micromixer is selected from: membrane dispersion micromixer, micromesh hole dispersion mixer, microchannel mixer, and micro packed bed mixer
The micro mixer is a micro-channel reactor
The mesitylene solution is a mesitylene acetic anhydride mixed solution; the nitric acid solution is a nitric acid-acetic acid mixed solution
The mass fraction of the mesitylene acetic anhydride mixed solution is 20-80%; the mass fraction of the nitric acid and acetic acid mixed solution is 20-80%; the molar ratio of the nitric acid to the mesitylene is as follows: nitric acid: mesitylene = (1.3-2.5): 1
The preferable mass fraction of the mesitylene acetic anhydride mixed solution is 40%; the preferred mass fraction of the nitric acid acetic acid mixed solution is 60%: the molar ratio of the nitric acid to the mesitylene is preferably as follows: nitric acid: mesitylene =1.5:1
The reaction temperature is 40-180 ℃, and the reaction time is 5-50S.
The reaction temperature is preferably 60-120 ℃, and the reaction time is preferably 20S.
The reaction temperature is more preferably 90 ℃.
The pressure of the back pressure valve is controlled between 0 and 10 bar. The main purpose is to regulate the boiling point of the material so that the material is free from gasification in the reaction module.
The preferred pressure of the back pressure valve is 0bar, when no bubbles are generated in the channel.
The invention has the advantages that: 1. because the materials are seriously released when being mixed and need to be dripped for a long time, the invention does not need to undergo the traditional reaction, is long in dripping time, and has the advantages of mild reaction condition, simple and convenient operation, less three wastes, low energy consumption and automatic continuous production.
2. In the traditional kettle type reactor, due to the serious material back mixing and the increase of impurities, the microchannel reactor is almost free from back mixing, the energy consumption is low, the impurities are few, and the reaction time is short.
3. The influence of different reaction conditions on the conversion rate of the product is investigated, and better process conditions are obtained: n (concentrated sulfuric acid): n (toluene) =1.5:1, reaction temperature 90 ℃, residence time 20s, mesitylene conversion 100%.
Detailed Description
The above-described scheme is further illustrated below with reference to specific examples. It should be understood that these examples are for illustrative purposes and are not intended to limit the scope of the present invention. The implementation conditions used in the examples can be further adjusted according to the conditions of the specific manufacturer.
Example 1
In the embodiment, mesitylene and nitric acid and sulfuric acid mixed acid are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to the mol ratio of 1.3:1, the temperature is controlled at 90 ℃, a back pressure valve is adjusted to 10bar, the reaction time is 20s, materials are received at an outlet after 4 reaction modules, and the 1-nitromesitylene is obtained after post-treatment. The conversion was 7% and the selectivity 63%.
Example 2
In the embodiment, mesitylene and nitric acid and sulfuric acid mixed acid are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to the mol ratio of 1.3:1, the temperature is controlled at 90 ℃, a back pressure valve is adjusted to be 0bar, the reaction time is 20s, materials are received at an outlet after 4 reaction modules, and the 1-nitromesitylene is obtained after post-treatment. The conversion was 6% and the selectivity 100%.
Example 3
In the embodiment, a 40 mass percent mesitylene acetic anhydride solution and a 60 mass percent nitric acid acetic acid solution are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to a molar ratio of 1.3:1, the temperature is controlled at 90 ℃, a back pressure valve is adjusted to be 0bar, the reaction time is 20s, materials are received at an outlet after passing through 4 reaction modules, and the 1-nitro-mesitylene is obtained after post-treatment. The conversion was 100% and the selectivity 96%.
Example 4
In the embodiment, a 45 mass percent mesitylene acetic anhydride solution and a 75 mass percent nitric acid acetic acid solution are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to a molar ratio of 1.3:1, the temperature is controlled at 90 ℃, a back pressure valve is adjusted to 10bar, the reaction time is 20s, materials are received at an outlet after passing through 4 reaction modules, and the 1-nitro-mesitylene is obtained after post-treatment. The conversion was 59% and the selectivity 96%.
Example 5
In the embodiment, a 45 mass percent mesitylene acetic anhydride solution and a 75 mass percent nitric acid acetic acid solution are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to a molar ratio of 1.3:1, the temperature is controlled at 80 ℃, a back pressure valve is adjusted to be 0bar, the reaction time is 40s, materials are received at an outlet after 4 reaction modules, and the 1-nitro-mesitylene is obtained after post-treatment. The conversion was 65% and the selectivity was 99%.
Example 5
In the embodiment, a 45 mass percent mesitylene acetic anhydride solution and a 75 mass percent nitric acid acetic acid solution are respectively injected into a microchannel reactor simultaneously by a plunger metering pump according to a molar ratio of 1.3:1, the temperature is controlled at 100 ℃, a back pressure valve is adjusted to be 0bar, the reaction time is 20s, materials are received at an outlet after 4 reaction modules, and the 1-nitro-mesitylene is obtained after post-treatment. The conversion was 64% and the selectivity was 99%.
The above examples are only for illustrating the technical idea and features of the present invention, and the purpose thereof is to enable those skilled in the art to understand the content of the present invention and implement the present invention accordingly, and not to limit the protection scope of the present invention accordingly. All equivalent changes and modifications made according to the spirit of the present invention should be covered within the protection scope of the present invention.
Claims (11)
1. A micro-channel reaction process for continuously synthesizing 1-nitromesitylene comprises the following steps:
respectively and simultaneously injecting a mesitylene solution and a nitric acid solution into a feed inlet of a micro mixer by using a plunger pump, adjusting the pressure of a back pressure valve, controlling the reaction time of materials, when a mixture flows from an inlet of the micro mixer to an outlet of the micro mixer, at least keeping the reaction temperature of at least one independent fluid module at 40-180 ℃, receiving the materials at the outlet after the reaction of at least one module, and obtaining the 1-nitromesitylene through subsequent treatment.
2. The process of claim 1, wherein: the micromixer is selected from: membrane dispersion micromixer, micromesh hole dispersion mixer, microchannel mixer, micro packed bed mixer.
3. The process of claim 2, wherein: the micro mixer is a micro-channel reactor.
4. The process of claim 1, wherein: the mesitylene solution is a pure mesitylene solution or a mixed mesitylene acetic anhydride solution.
5. The process of claim 1, wherein: the nitric acid solution is fuming nitric acid or a nitric acid and sulfuric acid mixed solution or a nitric acid and acetic acid mixed solution.
6. The process of claim 1, wherein: the reaction temperature is 40-180 ℃, and the reaction time is 5-200 s.
7. The process of claim 6, wherein: the reaction temperature is 60-120 ℃, and the reaction time is 5-50 s.
8. The process of claim 7, wherein: the reaction temperature was 90 ℃.
9. The process of claim 1, wherein: the process of claim 1, wherein the reaction is carried out by: the pressure of the back pressure valve is controlled between 0bar and 10 bar.
10. The process of claim 9, wherein: the pressure of the back pressure valve is controlled between 0 and 3 bar.
11. The process of claim 10, wherein: the pressure of the back pressure valve is controlled at 0 bar.
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| CN201811588680.8A CN111362803A (en) | 2018-12-25 | 2018-12-25 | Microchannel reaction process for continuously synthesizing 1-nitro mesitylene |
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| CN201811588680.8A CN111362803A (en) | 2018-12-25 | 2018-12-25 | Microchannel reaction process for continuously synthesizing 1-nitro mesitylene |
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