CN114685307A - Method for preparing 4-acetamido-3-nitrobenzoic acid by micro-reaction system - Google Patents
Method for preparing 4-acetamido-3-nitrobenzoic acid by micro-reaction system Download PDFInfo
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- CN114685307A CN114685307A CN202210135063.2A CN202210135063A CN114685307A CN 114685307 A CN114685307 A CN 114685307A CN 202210135063 A CN202210135063 A CN 202210135063A CN 114685307 A CN114685307 A CN 114685307A
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- acid
- acetamido
- sulfuric acid
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- flow rate
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 29
- BRQIMWBIZLRLSV-UHFFFAOYSA-N 4-acetamido-3-nitrobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1[N+]([O-])=O BRQIMWBIZLRLSV-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 35
- 239000000243 solution Substances 0.000 claims abstract description 10
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 239000007787 solid Substances 0.000 claims abstract description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims abstract description 6
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 5
- 238000001035 drying Methods 0.000 claims abstract description 4
- 239000012065 filter cake Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 239000005457 ice water Substances 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims abstract description 4
- 238000010791 quenching Methods 0.000 claims abstract description 4
- 230000000171 quenching effect Effects 0.000 claims abstract description 4
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000004519 manufacturing process Methods 0.000 abstract description 3
- 238000010924 continuous production Methods 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J19/0093—Microreactors, e.g. miniaturised or microfabricated reactors
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
Abstract
The invention discloses a method for preparing 4-acetamido-3-nitrobenzoic acid by a micro-reaction system, which comprises the following steps: s1, dissolving 4-acetamidobenzoic acid (25g,0.1523mol) in 98% sulfuric acid (125mL,2.3000mol), and dissolving 65% nitric acid (48mL,0.6923mol) in 98% sulfuric acid (39mL,0.7176 mol); s2, controlling the flow rate of the 4-acetamino-sulphuric acid solution to be 0.4mL/min and the flow rate of the nitric-sulfuric acid mixed solution to be 0.2mL/min, injecting materials into the microchannel reaction tube, controlling the reaction temperature to be 20 ℃, and ensuring the liquid holdup of the microchannel reaction tube to be 3.2 mL; and S3, quenching the reaction liquid by using an ice water solution, separating out, filtering, washing a filter cake by using water, and drying in vacuum to obtain a yellow solid, wherein the yellow solid is the 4-acetamido-3-nitrobenzoic acid. The invention has the advantages that: the liquid holdup can be obviously reduced, the temperature control is more accurate, the danger of production operation is reduced, and the continuous production is realized by using the microchannel reaction tube.
Description
Technical Field
The invention relates to the technical field of chemical industry, in particular to a method for preparing 4-acetamido-3-nitrobenzoic acid by a micro-reaction system.
Background
4-acetamido-3-nitrobenzoic acid is an important nitro-containing compound, has important medicinal value and application prospect, is widely applied to the fields of chemistry, medicine, materials, agricultural science and the like, the synthesis of the compound increasingly arouses the interest of organic chemists, and various methods for synthesizing 4-acetamido-3-nitrobenzoic acid have been developed, and the synthesis reaction formula is shown in figure 1.
Through improvement, several improved synthesis methods of 4-acetamido-3-nitrobenzoic acid are developed, and the synthesis reaction formula is shown in figure 2.
These methods have great limitations, such as more reaction liquid and great danger; the reaction is sensitive to temperature, the temperature control is difficult, and the like, and a new method for synthesizing the 4-acetamido-3-nitrobenzoic acid needs to be developed.
Disclosure of Invention
In order to solve the problems, the application provides the method for preparing the 4-acetamido-3-nitrobenzoic acid by using the micro-reaction system which can obviously reduce liquid holdup, control temperature more accurately, reduce production operation danger and realize continuous production by using the micro-channel reaction tube.
In order to solve the technical problems, the technical scheme provided by the invention is as follows: a method for preparing 4-acetamido-3-nitrobenzoic acid by using a micro-reaction system comprises the following steps:
s1, dissolving 4-acetamidobenzoic acid (25g,0.1523mol) in 98% sulfuric acid (125mL,2.3000mol), and dissolving 65% nitric acid (48mL,0.6923mol) in 98% sulfuric acid (39mL,0.7176 mol);
s2, controlling the flow rate of the 4-acetamino-sulphuric acid solution to be 0.4mL/min and the flow rate of the nitric-sulfuric acid mixed solution to be 0.2mL/min, injecting materials into the microchannel reaction tube, controlling the reaction temperature to be 20 ℃, and ensuring the liquid holdup of the microchannel reaction tube to be 3.2 mL;
and S3, quenching the reaction liquid by using an ice water solution, separating out, filtering, washing a filter cake by using water, and drying in vacuum to obtain a yellow solid, wherein the yellow solid is the 4-acetamido-3-nitrobenzoic acid.
Compared with the prior art, the invention has the advantages that: 4-Acylaminobenzoic acid 1(25g,0.1523mol) was dissolved in 98% sulfuric acid (125mL,2.3000mol) in a total volume of 136 mL; 65% nitric acid (48mL,0.6923mol) was dissolved in 98% sulfuric acid (39mL,0.7176mol) in a total volume of 81 mL; controlling the flow rate of the injected material, the reaction temperature and the liquid holdup in the microchannel reaction tube; the liquid holdup can be obviously reduced, the temperature control is more accurate, and the danger of production operation is reduced.
Drawings
FIG. 1 is a diagram of a prior art synthesis of the present invention.
FIG. 2 is a diagram of the synthesis of reaction formula two according to the prior art.
FIG. 3 is a synthesis scheme of the present invention.
FIG. 4 is a product spectrum of the present invention.
Detailed Description
Examples
4-Acylaminobenzoic acid 1(25g,0.1523mol) was dissolved in 98% sulfuric acid (125mL,2.3000mol) in a total volume of 136 mL. 65% nitric acid (48mL,0.6923mol) was dissolved in 98% sulfuric acid (39mL,0.7176mol) in a total volume of 81 mL.
The flow rate of the raw material sulfuric acid solution is controlled to be 0.8mL/min, the reaction temperature is 0 ℃, and the flow rate of the mixed acid of nitric acid and sulfuric acid is changed.
TABLE I shows the yield change at different flow rates of mixed nitric-sulfuric acid
The flow rate of the raw material sulfuric acid solution is controlled to be 0.8mL/min, the flow rate of the nitric-sulfuric mixed acid is controlled to be 0.4mL/min, and the reaction temperature is changed.
TABLE II yield change at different temperatures
The reaction temperature was controlled at 0 ℃ and the time was varied by changing the flow rate of the two feed paths (ratio).
TABLE III is the change in yield at different reaction times
The method for preparing the 4-acetamido-3-nitrobenzoic acid by the micro-reaction system comprises the following steps:
s1, dissolving 4-acetamidobenzoic acid (25g,0.1523mol) in 98% sulfuric acid (125mL,2.3000mol), and dissolving 65% nitric acid (48mL,0.6923mol) in 98% sulfuric acid (39mL,0.7176 mol);
s2, controlling the flow rate of the 4-acetamino-sulphuric acid solution to be 0.4mL/min and the flow rate of the nitric-sulfuric acid mixed solution to be 0.2mL/min, injecting materials into the microchannel reaction tube, controlling the reaction temperature to be 20 ℃, and ensuring the liquid holdup of the microchannel reaction tube to be 3.2 mL;
and S3, quenching the reaction liquid by using an ice water solution, separating out, filtering, washing a filter cake by using water, and drying in vacuum to obtain a yellow solid, wherein the yellow solid is the 4-acetamido-3-nitrobenzoic acid.
It should be understood that the above examples are only for clarity of illustration and are not intended to limit the embodiments. Other variations and modifications will be apparent to persons skilled in the art in light of the above description. And are neither required nor exhaustive of all embodiments. And obvious variations or modifications therefrom are within the scope of the invention.
Claims (1)
1. A method for preparing 4-acetamido-3-nitrobenzoic acid by using a micro-reaction system is characterized by comprising the following steps:
s1, dissolving 4-acetamidobenzoic acid (25g,0.1523mol) in 98% sulfuric acid (125mL,2.3000mol), and dissolving 65% nitric acid (48mL,0.6923mol) in 98% sulfuric acid (39mL,0.7176 mol);
s2, controlling the flow rate of the 4-acetamino-sulphuric acid solution to be 0.4mL/min and the flow rate of the nitric-sulfuric acid mixed solution to be 0.2mL/min, injecting materials into the microchannel reaction tube, controlling the reaction temperature to be 20 ℃, and ensuring the liquid holdup of the microchannel reaction tube to be 3.2 mL;
and S3, quenching the reaction liquid by using an ice water solution, separating out, filtering, washing a filter cake by using water, and drying in vacuum to obtain a yellow solid, wherein the yellow solid is the 4-acetamido-3-nitrobenzoic acid.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210135063.2A CN114685307A (en) | 2022-02-14 | 2022-02-14 | Method for preparing 4-acetamido-3-nitrobenzoic acid by micro-reaction system |
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|---|---|---|---|
| CN202210135063.2A CN114685307A (en) | 2022-02-14 | 2022-02-14 | Method for preparing 4-acetamido-3-nitrobenzoic acid by micro-reaction system |
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| CN114685307A true CN114685307A (en) | 2022-07-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN202210135063.2A Pending CN114685307A (en) | 2022-02-14 | 2022-02-14 | Method for preparing 4-acetamido-3-nitrobenzoic acid by micro-reaction system |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428673A (en) * | 1964-06-03 | 1969-02-18 | Du Pont | Nitration of 4-acetamidobenzoic acid |
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2022
- 2022-02-14 CN CN202210135063.2A patent/CN114685307A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3428673A (en) * | 1964-06-03 | 1969-02-18 | Du Pont | Nitration of 4-acetamidobenzoic acid |
Non-Patent Citations (1)
| Title |
|---|
| 李林吉等: ""微通道反应器在芳香化合物硝化反应中的应用进展"", 《化学与生物工程》, vol. 38, no. 2, pages 7 - 11 * |
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Application publication date: 20220701 |