CN111004126A - Preparation method of p-nitrophenol sodium salt - Google Patents
Preparation method of p-nitrophenol sodium salt Download PDFInfo
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- CN111004126A CN111004126A CN201911375782.6A CN201911375782A CN111004126A CN 111004126 A CN111004126 A CN 111004126A CN 201911375782 A CN201911375782 A CN 201911375782A CN 111004126 A CN111004126 A CN 111004126A
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- CURNJKLCYZZBNJ-UHFFFAOYSA-M sodium;4-nitrophenolate Chemical compound [Na+].[O-]C1=CC=C([N+]([O-])=O)C=C1 CURNJKLCYZZBNJ-UHFFFAOYSA-M 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 84
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000001816 cooling Methods 0.000 claims abstract description 25
- 239000013078 crystal Substances 0.000 claims abstract description 24
- 238000002425 crystallisation Methods 0.000 claims abstract description 21
- 230000008025 crystallization Effects 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 19
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000002844 melting Methods 0.000 claims abstract description 16
- 230000008018 melting Effects 0.000 claims abstract description 16
- 239000007787 solid Substances 0.000 claims abstract description 11
- 239000005992 Sodium p-nitrophenolate Substances 0.000 claims abstract description 10
- 238000010438 heat treatment Methods 0.000 claims abstract description 9
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 8
- 238000005086 pumping Methods 0.000 claims abstract description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 29
- 239000000243 solution Substances 0.000 claims description 25
- 238000001704 evaporation Methods 0.000 claims description 20
- 230000008020 evaporation Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 239000011780 sodium chloride Substances 0.000 claims description 14
- OORLTLMFPORJLV-UHFFFAOYSA-N 4-nitrophenol;sodium Chemical compound [Na].OC1=CC=C([N+]([O-])=O)C=C1 OORLTLMFPORJLV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012267 brine Substances 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 14
- 238000004519 manufacturing process Methods 0.000 abstract description 13
- 239000002994 raw material Substances 0.000 abstract description 8
- 239000006227 byproduct Substances 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 5
- 239000000463 material Substances 0.000 abstract description 4
- 230000035484 reaction time Effects 0.000 abstract description 4
- 238000007086 side reaction Methods 0.000 abstract description 3
- 230000007062 hydrolysis Effects 0.000 description 11
- 238000012360 testing method Methods 0.000 description 8
- 239000003643 water by type Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 239000000413 hydrolysate Substances 0.000 description 3
- 238000005070 sampling Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 239000012847 fine chemical Substances 0.000 description 2
- STZCRXQWRGQSJD-GEEYTBSJSA-M methyl orange Chemical compound [Na+].C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S([O-])(=O)=O)C=C1 STZCRXQWRGQSJD-GEEYTBSJSA-M 0.000 description 2
- 229940012189 methyl orange Drugs 0.000 description 2
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000000987 azo dye Substances 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229960003893 phenacetin Drugs 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000010865 sewage Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000988 sulfur dye Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
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
- C07C201/14—Preparation of nitro compounds by formation of nitro groups together with reactions not involving the formation of nitro 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
-
- 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
-
- 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 preparation method of p-nitrophenol sodium salt, which comprises the following steps: a) heating and melting p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution in a dissolving kettle; b) introducing nitrogen into the system before reaction for 3-6 times to replace air, pumping the heated and melted p-chloronitrobenzene and sodium hydroxide solution into the microreactor by using a feed valve, mixing uniformly, and carrying out high-temperature high-pressure reaction; c) and transferring the solution after the reaction to a cooling crystallization kettle, and cooling to separate out a sodium p-nitrophenolate solid containing crystal water. The invention adopts the microchannel for hydrolysis reaction, realizes the instantaneous uniform mixing and high-efficiency heat transfer of the raw materials, simultaneously reduces the equivalence ratio of the materials in the reaction process, reduces the side reaction and the difficulty of treatment after the reaction, can recycle water, reduces the energy consumption in production, improves the utilization rate of the raw materials, ensures that the production process is more environment-friendly, has low production cost and greatly shortens the reaction time; the prepared p-nitrophenol sodium salt is light yellow or orange yellow in color, and few byproducts are generated.
Description
Technical Field
The invention relates to the technical field of fine chemical product synthesis methods, in particular to a preparation method of p-nitrophenol sodium salt.
Background
P-nitrophenol is an important intermediate and is mainly used for producing fine chemicals such as pesticides, medicines, dyes and the like. The compound is used for preparing phenacetin, paracetamol, a developer, a rubber anti-aging agent, a sulfur dye, an azo dye, a fur dye and the like, can also be used for a leather mildew preventive and an indicator, and can also be used as a raw material for synthesizing diaminodiphenyl ether for preparing polyimide high-performance engineering plastics. In recent years, with the expansion of industrial production, the demand for nitrophenol is increasing.
P-nitrophenol is usually produced by a traditional batch method, p-nitrochlorobenzene is hydrolyzed into p-nitrophenol sodium salt at high temperature and high pressure, and then is acidified to form p-nitrophenol. Such as chinese patent CN 03818517.2. An excess of alkali is often required to ensure a high conversion and a fast reaction rate, which results in an increase in by-products, makes the post-treatment more complicated and results in a large amount of waste. The Chinese patent CN200410041851.7 adopts a continuous hydrolysis process flow in a plurality of serially connected reaction kettles, improves the hydrolysis efficiency, but is still an intermittent reaction in the reaction kettles essentially and also needs to treat a large amount of sewage.
The Chinese patent CN200910251614.6 adopts the method of improving the concentration of sodium hydroxide so as to improve the productivity of a hydrolysis kettle, reduce energy consumption and reduce the discharge of waste water, and obtains certain effect, however, the method still belongs to batch reaction, the separation and purification of materials are complex, the reaction conversion rate is low, and a large amount of industrial alkaline waste water can still be generated. Chinese patent CN200410014570.2 adopts a water treatment method of activated carbon adsorption. How to reduce reaction byproducts and improve hydrolysis efficiency becomes a technical problem which needs to be solved urgently.
The microchannel reaction technology can not only strengthen the process and greatly improve the production efficiency, but also improve the stability, safety, operability and environmental friendliness of the process. However, at present, microchannels are often used for nitration, oxidation and the like, and are rarely used for hydrolysis.
Disclosure of Invention
In order to solve the defects or shortcomings in the prior art, the invention aims to provide a preparation method of p-nitrophenol sodium salt, which adopts a microchannel for hydrolysis reaction, realizes the instantaneous uniform mixing and high-efficiency heat transfer of raw materials, simultaneously reduces the equivalence ratio of materials in the reaction process, reduces the occurrence of side reactions and the difficulty of treatment after the reaction, can recycle water, reduces the energy consumption in production, improves the utilization rate of the raw materials, ensures that the production process is more environment-friendly, has low production cost and greatly shortens the reaction time; the prepared p-nitrophenol sodium salt is light yellow or orange yellow in color, and few byproducts are generated.
The invention adopts the following technical scheme to realize the purpose of the invention:
a preparation method of p-nitrophenol sodium salt comprises the following steps:
a) heating and melting p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution in a dissolving kettle;
b) introducing nitrogen into the system before reaction for 3-6 times to replace air, pumping the heated and melted p-chloronitrobenzene and sodium hydroxide solution into the microreactor by using a feed valve, mixing uniformly, and carrying out high-temperature high-pressure reaction;
c) and transferring the solution after the reaction to a cooling crystallization kettle, and cooling to separate out a sodium p-nitrophenolate solid containing crystal water.
Wherein in the step b), the molar ratio of the sodium hydroxide to the p-chloronitrobenzene is (2.0-2.4): 1.
in the step b), the specific conditions of the high-temperature high-pressure reaction are as follows: the nitrogen pressure is 4-8MPa, the temperature is 150-.
In the step c), water in the heat exchanger of the cooling crystallization kettle is heated to be changed into steam, and the steam can enter a coil of the evaporation crystallization kettle in the next step to be used for evaporating the sodium chloride solution; and (3) feeding the cooled and filtered sodium chloride solution into a brine evaporation kettle for evaporation, collecting evaporated white sodium chloride crystals, and circulating the evaporated water vapor and the filtrate (containing a small amount of unreacted sodium hydroxide) remaining after crystallization into a dissolving kettle for further reaction.
Wherein, in the step c), the color of the p-nitrophenol sodium solid containing the crystal water is light yellow or orange yellow.
Compared with the prior art, the invention has the following beneficial effects:
1) the invention adopts the microchannel for hydrolysis reaction, realizes the instantaneous uniform mixing and high-efficiency heat transfer of the raw materials, simultaneously reduces the equivalence ratio of the materials in the reaction process, reduces the side reaction and the difficulty of treatment after the reaction, can recycle water, reduces the energy consumption in production, improves the utilization rate of the raw materials, ensures that the production process is more environment-friendly, has low production cost and greatly shortens the reaction time; the prepared p-nitrophenol sodium salt is light yellow or orange yellow in color, and few byproducts are generated.
2) The production process has the advantages of low reaction energy consumption, short reaction time and low production cost, and is suitable for large-scale batch production.
Drawings
FIG. 1 is a schematic diagram of the process for preparing p-nitrophenol sodium salt of the present invention.
Detailed Description
The present invention is further illustrated by the following specific examples, which are, however, not intended to limit the scope of the invention.
The raw materials used in the examples of the present invention are all commercially available.
Various performance test standards or methods:
the color was observed by naked eye.
The method for testing the content of the sodium p-nitrophenolate comprises the following steps: accurately weighing 3.0000g of sample in a 250mL conical flask, adding 50mL of boiling water for dissolving, cooling to room temperature, adding 100mL of water, adding 2-3 drops of phenolphthalein indicator (10 g/L of ethanol solution: weighing 1g of phenolphthalein in absolute ethanol, diluting with absolute ethanol to 100 mL), titrating with 1.0mol/L of hydrochloric acid standard solution until the sample is orange, recording the reading V1, dropwise adding 2-3 drops of methyl orange indicator (1 g/L of solution: weighing 0.1g of methyl orange, dissolving in 70 ℃ of water, cooling, diluting to 100 mL), continuously titrating with 1.0mol/L of hydrochloric acid standard solution until the sample is reddish, recording the reading V2.
Purity test method: HPLC liquid chromatography was used for testing.
Example 1
A preparation method of p-nitrophenol sodium salt comprises the following steps:
a) heating and melting 630Kg of p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution with the mass concentration of 15 percent (320 Kg of sodium hydroxide is dissolved in 1800Kg of water) in a dissolving kettle at the same time;
b) before the reaction, nitrogen gas was repeatedly introduced into the system for 3 times to displace air, and the p-chloronitrobenzene and the aqueous sodium hydroxide solution which were heated and melted were mixed in the mass ratio (6.3: 21.2) pumping the mixture into a micro reactor by using a feed valve, uniformly mixing, and carrying out high-temperature and high-pressure reaction under the specific conditions of: the nitrogen pressure is 4Mpa, the temperature is 150 ℃, and the residence time in the reaction system is 2 h;
c) transferring the reaction liquid to a cooling crystallization kettle, wherein water in a heat exchanger of the cooling crystallization kettle is heated to be changed into steam, and the steam can enter a coil pipe of the evaporation crystallization kettle in the next step for evaporating the sodium chloride solution; the sodium chloride solution filtered by cooling enters a brine evaporation kettle for evaporation, evaporated sodium chloride crystals are collected, and the evaporated water vapor and the residual filtrate after crystallization circularly enter a dissolution kettle for further reaction; cooling to separate out light yellow p-nitrophenol sodium solid containing four crystal water. The color and other performance index test data of the prepared p-nitrophenol sodium solid containing four crystal water are shown in table 1.
Example 2:
a preparation method of p-nitrophenol sodium salt comprises the following steps:
a) heating and melting 630Kg of p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution with the mass concentration of 12 percent (352 Kg of sodium hydroxide is dissolved in 2581Kg of water) in a dissolving kettle at the same time;
b) before the reaction, nitrogen gas was repeatedly introduced into the system for 5 times to displace air, and the p-chloronitrobenzene and the aqueous sodium hydroxide solution which were heated and melted were mixed in the mass ratio (6.3: 29.3) pumping the mixture into a microreactor by using a feed valve, uniformly mixing, and carrying out high-temperature and high-pressure reaction under the specific conditions of: the nitrogen pressure is 6Mpa, the temperature is 160 ℃, and the residence time in the reaction system is 1 h;
c) transferring the reaction liquid to a cooling crystallization kettle, wherein water in a heat exchanger of the cooling crystallization kettle is heated to be changed into steam, and the steam can enter a coil pipe of the evaporation crystallization kettle in the next step for evaporating the sodium chloride solution; the sodium chloride solution filtered by cooling enters a brine evaporation kettle for evaporation, evaporated sodium chloride crystals are collected, and the evaporated water vapor and the filtrate (containing a small amount of unreacted sodium hydroxide) left after crystallization circularly enter a dissolving kettle to further participate in the reaction; cooling to separate out light yellow p-nitrophenol sodium solid containing four crystal water. The color and other performance index test data of the prepared p-nitrophenol sodium solid containing four crystal water are shown in table 1.
Example 3:
a preparation method of p-nitrophenol sodium salt comprises the following steps:
a) heating and melting 630Kg of p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution with the mass concentration of 25 percent (384 Kg of sodium hydroxide is dissolved in 1152Kg of water) in a dissolving kettle at the same time;
b) nitrogen gas is repeatedly introduced into the system for 6 times to replace air before the reaction, and the p-chloronitrobenzene and the sodium hydroxide aqueous solution which are heated and melted are mixed according to the mass ratio (6.3: 15.36) pumping the mixture into a micro reactor by a feed valve, mixing the mixture uniformly, and carrying out high-temperature and high-pressure reaction under the specific conditions: the nitrogen pressure is 8Mpa, the temperature is 180 ℃, and the residence time in the reaction system is 15 min;
c) transferring the reaction liquid to a cooling crystallization kettle, wherein water in a heat exchanger of the cooling crystallization kettle is heated to be changed into steam, and the steam can enter a coil pipe of the evaporation crystallization kettle in the next step for evaporating the sodium chloride solution; the sodium chloride solution filtered by cooling enters a brine evaporation kettle for evaporation, evaporated sodium chloride crystals are collected, and the evaporated water vapor and the filtrate (containing a small amount of unreacted sodium hydroxide) left after crystallization circularly enter a dissolving kettle to further participate in the reaction; cooling to separate out orange-yellow p-nitrophenol sodium solid containing two crystal waters. The color and other performance index test data of the prepared p-nitrophenol sodium solid containing two crystal waters are shown in Table 1.
Comparative example 1:
adding 2120Kg of sodium hydroxide solution (320 Kg of sodium hydroxide is dissolved in 1800Kg of water) with the mass concentration of 15% into a hydrolysis kettle, adding 630Kg of p-chloronitrobenzene into a melting kettle, melting, and adding into the hydrolysis kettle; heating to 160 ℃, controlling the pressure in the pot to be 0.6MPa, then continuing to react for 6 hours, sampling and detecting the reaction end point, cooling the hydrolysate to 40 ℃ after the reaction is finished, performing suction filtration and centrifugation to obtain the sodium p-nitrophenolate containing four crystal waters. The test data of various performance indexes such as color and the like of the prepared sodium p-nitrophenolate containing four crystal waters are shown in Table 1.
Comparative example 2:
2933Kg of sodium hydroxide solution with the mass concentration of 12% (352 Kg of sodium hydroxide is dissolved in 2581Kg of water) is added into the hydrolysis kettle, and 630Kg of p-chloronitrobenzene is added into the melting kettle to be melted and then also added into the hydrolysis kettle; heating to 160 ℃, controlling the pressure in the pot to be 0.6MPa, then continuing to react for 6 hours, sampling and detecting the reaction end point, cooling the hydrolysate to 40 ℃ after the reaction is finished, performing suction filtration and centrifugation to obtain the sodium p-nitrophenolate containing four crystal waters. The test data of various performance indexes such as color and the like of the prepared sodium p-nitrophenolate containing four crystal waters are shown in Table 1.
Comparative example 3:
1536Kg of sodium hydroxide solution with the mass concentration of 25% (384 Kg of sodium hydroxide is dissolved in 1152Kg of water) is added into the hydrolysis kettle, 630Kg of p-chloronitrobenzene is added into the melting kettle to be melted and then is also added into the hydrolysis kettle; heating to 160 ℃, controlling the pressure in the pot to be 0.6MPa, then continuing to react for 6 hours, sampling and detecting the reaction end point, cooling the hydrolysate to 40 ℃ after the reaction is finished, performing suction filtration and centrifugation to obtain the sodium p-nitrophenolate containing two crystal waters. The test data of various performance indexes such as the color and the like of the prepared sodium p-nitrophenolate containing two crystal waters are shown in Table 1.
TABLE 1
| Example 1 | Example 2 | Example 3 | Comparative example 1 | Comparative example 2 | Comparative example 3 | |
| Colour(s) | Light yellow | Light yellow | Orange yellow | Brown colour | Yellow brown | Orange red |
| Content% | 79 | 78 | 77 | 65 | 66 | 63 |
| Weight (Kg) | 822 | 825 | 830 | 910 | 920 | 835 |
| Purity% | 99.2 | 99.8 | 99.0 | 97 | 95 | 96 |
Claims (6)
1. The preparation method of the p-nitrophenol sodium salt is characterized by comprising the following steps:
a) heating and melting p-chloronitrobenzene in a melting kettle, and preparing a sodium hydroxide solution in a dissolving kettle;
b) introducing nitrogen into the system before reaction for 3-6 times to replace air, pumping the heated and melted p-chloronitrobenzene and sodium hydroxide solution into the microreactor by using a feed valve, mixing uniformly, and carrying out high-temperature high-pressure reaction;
c) and transferring the solution after the reaction to a cooling crystallization kettle, and cooling to separate out a sodium p-nitrophenolate solid containing crystal water.
2. The method for preparing p-nitrophenol sodium salt according to claim 1, wherein in step b), the molar ratio of sodium hydroxide to p-chloronitrobenzene is (2.0-2.4): 1.
3. the method for preparing p-nitrophenol sodium salt according to claim 1, wherein in step b), the specific conditions of the high temperature and high pressure reaction are as follows: the nitrogen pressure is 4-8MPa, the temperature is 150-.
4. The method for preparing p-nitrophenol sodium salt according to claim 1, wherein in step c), the water in the heat exchanger of the cooling crystallization kettle is heated to become steam which can be sent to the coil of the next evaporation crystallization kettle for evaporating the sodium chloride salt solution; and (3) feeding the cooled and filtered sodium chloride solution into a brine evaporation kettle for evaporation, collecting evaporated white sodium chloride crystals, and circulating the evaporated water vapor and the filtrate (containing unreacted sodium hydroxide) remaining after crystallization into a dissolving kettle for further reaction.
5. The method for preparing p-nitrophenol sodium salt according to claim 1, wherein in step c), the amount of crystal water of the p-nitrophenol sodium solid containing crystal water is 2-4.
6. The method for preparing p-nitrophenol sodium salt according to claim 1, wherein in step c), the color of the p-nitrophenol sodium containing crystal water is light yellow or orange yellow.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111499515A (en) * | 2020-04-28 | 2020-08-07 | 南京简迪环境工程有限公司 | Process for synthesizing sodium nitrophenolate by continuous hydrolysis of nitrochlorobenzene |
| CN113200862A (en) * | 2021-05-17 | 2021-08-03 | 安徽东至广信农化有限公司 | Synthetic process of sodium p-nitrophenolate |
| CN116078334A (en) * | 2023-04-10 | 2023-05-09 | 山东冠森高分子材料科技股份有限公司 | Paranitrophenol sodium apparatus for producing with automatic temperature control function |
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| CN113200862B (en) * | 2021-05-17 | 2023-02-28 | 安徽东至广信农化有限公司 | Synthetic process of sodium p-nitrophenolate |
| CN116078334A (en) * | 2023-04-10 | 2023-05-09 | 山东冠森高分子材料科技股份有限公司 | Paranitrophenol sodium apparatus for producing with automatic temperature control function |
| CN116078334B (en) * | 2023-04-10 | 2023-06-02 | 山东冠森高分子材料科技股份有限公司 | Paranitrophenol sodium apparatus for producing with automatic temperature control function |
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