CN113200862B - Synthetic process of sodium p-nitrophenolate - Google Patents
Synthetic process of sodium p-nitrophenolate Download PDFInfo
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- CN113200862B CN113200862B CN202110535972.0A CN202110535972A CN113200862B CN 113200862 B CN113200862 B CN 113200862B CN 202110535972 A CN202110535972 A CN 202110535972A CN 113200862 B CN113200862 B CN 113200862B
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Abstract
The invention discloses a synthesis process of sodium p-nitrophenolate, belonging to the technical field of fine chemical product synthesis, and the synthesis process comprises the following steps: firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 160-165 ℃, controlling the pressure to be 0.75-0.8MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and preheating p-nitrochlorobenzene and a sodium hydroxide solution to 150-155 ℃; secondly, feeding, wherein the flow of the p-nitrochlorobenzene is controlled to be 600-640g/h and the flow of the sodium hydroxide solution is controlled to be 5100-5200g/h; and step three, cooling and crystallizing the obtained reaction liquid to obtain the p-nitrophenol sodium. According to the invention, the quaternary ammonium salt surfactant is added in the synthesis of the p-nitrophenol sodium, so that the reaction is milder, the phenomenon that the local reaction is too fast to form black materials to a certain extent, which causes side reactions, is prevented, and the yield and the purity are further improved.
Description
Technical Field
The invention belongs to the technical field of fine chemical product synthesis, and particularly relates to a synthesis process of sodium p-nitrophenolate.
Background
Sodium p-nitrophenolate is an important fine chemical intermediate, can be used as raw material for preparing pesticides parathion and methyl parathion, and can be used for preparing p-aminophenol through acidification reduction, and the latter is an important intermediate of developing agent, medicine and dye, and the production process of the sodium p-nitrophenolate is as follows: adding a sodium hydroxide solution with a certain volume concentration of 133-136g/L into a hydrolysis kettle, and then adding quantitative molten p-nitroChlorobenzene was charged with air at 0.8kg/cm 2 Heating the material to 157 deg.C, keeping the pressure in the kettle at 0.6Mpa, stopping heating, performing hydrolysis reaction to release heat, naturally increasing the temperature and pressure to 168 deg.C and 0.75Mpa, maintaining for 3.5h, cooling to 120 deg.C, pressing the material to crystallizer by using the residual pressure in the kettle, cooling for crystallization, and vacuum filtering to obtain the product. The process has the advantages of low production efficiency, low product yield, large amount of wastewater generated in the production process and high labor intensity.
According to a thermochemical theory, the hydrolysis reaction of p-nitrochlorobenzene and sodium hydroxide is an exothermic reaction, the concentration of the sodium hydroxide participating in the hydrolysis reaction is not too high, and black materials are easily generated due to too high alkali concentration, wherein the delta H =178 KJ/mol; the concentration of alkali is increased, the reaction speed is increased in multiples, a large amount of heat released instantly causes the temperature and the pressure in the kettle to rise too fast and be difficult to control, and meanwhile, sodium p-nitrophenolate generated under the conditions of high temperature, pressure and alkalinity can generate reduction condensation reaction to form a black material phenomenon.
Disclosure of Invention
The invention provides a synthesis process of p-nitrophenol sodium.
The technical problems to be solved by the invention are as follows:
in the traditional industrial production, excessive sodium hydroxide is required to be added to ensure that high conversion rate and faster reaction speed are obtained, so that the increase of byproducts is caused, the hydrolysis reaction of p-nitrochlorobenzene and sodium hydroxide is an exothermic reaction, the concentration of the sodium hydroxide participating in the hydrolysis reaction is not too high, and black materials are easily generated due to too high alkali concentration, wherein the Delta H =178 KJ/mol; the concentration of alkali is increased, the reaction speed is increased in multiples, a large amount of heat released instantly causes the temperature and the pressure in the kettle to rise too fast and to be difficult to control, and meanwhile, sodium p-nitrophenolate generated under the conditions of high temperature, pressure and alkalinity can generate reduction condensation reaction to form a black material phenomenon.
The purpose of the invention can be realized by the following technical scheme:
a synthetic process of sodium p-nitrophenolate comprises the following steps:
firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 160-165 ℃, controlling the pressure to be 0.75-0.8MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and preheating the p-nitrochlorobenzene and a sodium hydroxide solution to 150-155 ℃;
secondly, feeding, wherein the flow of the p-nitrochlorobenzene is controlled to be 600-640g/h and the flow of the sodium hydroxide solution is 5100-5200g/h during feeding;
and step three, cooling and crystallizing the obtained reaction liquid to obtain the p-nitrophenol sodium.
Further, the quaternary ammonium surfactant is prepared by the following steps:
step S11, mixing sodium sulfite and deionized water to prepare a saturated solution, setting the temperature to be 85 ℃, dropwise adding epoxy chloropropane, controlling the dropwise adding time to be 1.5-2h, keeping the temperature unchanged after the dropwise adding is finished, continuing to react for 1.5h, reducing the temperature of a reaction solution to room temperature after the reaction is finished, precipitating crystals, then carrying out vacuum filtration, and recrystallizing with deionized water to obtain an intermediate 1;
the reaction process is as follows:
s12, mixing xylene and diethylenetriamine, setting the temperature to be 90 ℃, dropwise adding the mixed xylene and diethylenetriamine into benzoic acid, continuously heating to 140-150 ℃ after dropwise adding is finished, continuously reacting for 3 hours at the temperature, then heating to 240 ℃, continuously reacting for 3 hours, and obtaining an intermediate 2 after the reaction is finished;
the reaction process is as follows:
and S13, cooling the intermediate 2 obtained in the step S12 to 80 ℃, adding the intermediate 1, and continuously stirring for reaction for 4 hours to obtain the quaternary ammonium surfactant.
The reaction process is as follows:
further, the molar ratio of the sodium sulfite to the epichlorohydrin used in step S11 is 1.2:1; in the step S12, the dosage ratio of the dimethylbenzene to the diethylenetriamine to the benzoic acid is 20mL:1g:1.4g; in the step S13, the mass ratio of the intermediate 2 to the intermediate 1 is 1:1.
further, the mass fraction of the sodium hydroxide solution is 4-8%; the dosage mass ratio of the nitrochlorobenzene to the quaternary ammonium salt surfactant is 100:9-11; the molar ratio of the nitrochlorobenzene to the sodium hydroxide is 1:1.7-1.9.
The invention has the beneficial effects that:
according to the invention, the quaternary ammonium salt surfactant is added in the synthesis of the p-nitrophenol sodium, and a relatively uniform environment can be formed after the quaternary ammonium salt surfactant is added, so that the reaction is milder, and the occurrence of side reactions caused by the formation of black materials due to the over-rapid local reaction can be prevented to a certain extent; in addition, bubbles generated in the reaction process form a small reaction environment, so that the reaction efficiency is improved, and the yield and the purity are further improved.
The quaternary ammonium salt surfactant prepared by the invention contains an aryl imidazoline structure in the structure, has good thermal stability and good temperature resistance in the later use process, contains a sulfonic acid group in the structure and has excellent alkali resistance, the sulfonated quaternary ammonium salt surfactant has good solubilization performance under the high temperature and alkaline conditions of the synthesis process, and meanwhile, the sulfonated quaternary ammonium salt surfactant has good biodegradability, and the generated wastewater is easy to treat.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparing a quaternary ammonium salt surfactant:
step S11, mixing sodium sulfite and deionized water to prepare a saturated solution, setting the temperature to be 85 ℃, dropwise adding epoxy chloropropane, controlling the dropwise adding time to be 1.5h, keeping the temperature unchanged after the dropwise adding is finished, continuing to react for 1.5h, cooling the temperature of a reaction solution to room temperature after the reaction is finished, precipitating crystals, then carrying out vacuum filtration, and recrystallizing with deionized water to obtain an intermediate 1;
s12, mixing xylene and diethylenetriamine, setting the temperature to be 90 ℃, dropwise adding the mixed xylene and diethylenetriamine into benzoic acid, continuously heating to 140 ℃ after dropwise adding, continuously reacting for 3 hours at the temperature, then heating to 240 ℃, continuously reacting for 3 hours, and obtaining an intermediate 2 after the reaction is finished;
and S13, cooling the intermediate 2 obtained in the step S12 to 80 ℃, adding the intermediate 1, and continuously stirring for reaction for 4 hours to obtain the quaternary ammonium surfactant.
Wherein, the molar ratio of the sodium sulfite to the epichlorohydrin used in the step S11 is 1.2:1; in the step S12, the dosage ratio of the dimethylbenzene to the diethylenetriamine to the benzoic acid is 20mL:1g:1.4g; in the step S13, the mass ratio of the intermediate 2 to the intermediate 1 is 1:1.
example 2
Preparing a quaternary ammonium salt surfactant:
step S11, mixing sodium sulfite and deionized water to prepare a saturated solution, setting the temperature to be 85 ℃, dropwise adding epoxy chloropropane, controlling the dropwise adding time to be 1.8h, keeping the temperature unchanged after the dropwise adding is finished, continuously reacting for 1.5h, cooling the temperature of a reaction solution to room temperature after the reaction is finished, precipitating crystals, then carrying out reduced pressure suction filtration, and recrystallizing with deionized water to obtain an intermediate 1;
s12, mixing xylene and diethylenetriamine, setting the temperature to be 90 ℃, dropwise adding the mixed xylene and diethylenetriamine into benzoic acid, continuously heating to 145 ℃ after dropwise adding, continuously reacting for 3 hours at the temperature, then heating to 240 ℃, continuously reacting for 3 hours, and obtaining an intermediate 2 after the reaction is finished;
and S13, cooling the intermediate 2 obtained in the step S12 to 80 ℃, adding the intermediate 1, and continuously stirring for reaction for 4 hours to obtain the quaternary ammonium surfactant.
Wherein, the molar ratio of the sodium sulfite to the epoxy chloropropane in the step S11 is 1.2:1; in the step S12, the dosage ratio of the dimethylbenzene to the diethylenetriamine to the benzoic acid is 20mL:1g:1.4g; in the step S13, the mass ratio of the intermediate 2 to the intermediate 1 is 1:1.
example 3
Preparing a quaternary ammonium surfactant:
step S11, mixing sodium sulfite and deionized water to prepare a saturated solution, setting the temperature to be 85 ℃, dropwise adding epoxy chloropropane, controlling the dropwise adding time to be 2h, keeping the temperature unchanged after the dropwise adding is finished, continuing to react for 1.5h, reducing the temperature of a reaction solution to room temperature after the reaction is finished, precipitating crystals, then carrying out reduced pressure suction filtration, and recrystallizing with deionized water to obtain an intermediate 1;
s12, mixing xylene and diethylenetriamine, setting the temperature to be 90 ℃, dropwise adding the mixed xylene and diethylenetriamine into benzoic acid, continuously heating to 150 ℃ after dropwise adding is finished, continuously reacting for 3 hours at the temperature, then heating to 240 ℃, continuously reacting for 3 hours, and obtaining an intermediate 2 after the reaction is finished;
and S13, cooling the intermediate 2 obtained in the step S12 to 80 ℃, adding the intermediate 1, and continuously stirring for reaction for 4 hours to obtain the quaternary ammonium surfactant.
Wherein, the molar ratio of the sodium sulfite to the epichlorohydrin used in the step S11 is 1.2:1; in the step S12, the dosage ratio of the dimethylbenzene to the diethylenetriamine to the benzoic acid is 20mL:1g:1.4g; in the step S13, the mass ratio of the intermediate 2 to the intermediate 1 is 1:1.
example 4
Firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 160 ℃, controlling the pressure to be 0.75MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and then preheating the p-nitrochlorobenzene and a sodium hydroxide solution to 150 ℃;
secondly, feeding, wherein the flow of the p-nitrochlorobenzene is controlled to be 600g/h and the flow of the sodium hydroxide solution is 5100g/h during feeding;
and step three, cooling and crystallizing the obtained reaction liquid to obtain the sodium p-nitrophenolate.
Wherein the mass fraction of the sodium hydroxide solution is 4 percent; the dosage mass ratio of the nitrochlorobenzene to the quaternary ammonium salt surfactant is 100:9; the molar ratio of the nitrochlorobenzene to the sodium hydroxide is 1:1.7. the quaternary ammonium surfactant was prepared as in example 2.
Example 5
Firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 162 ℃, controlling the pressure to be 0.75MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and then preheating the p-nitrochlorobenzene and a sodium hydroxide solution to 150 ℃;
secondly, feeding, wherein the flow rate of the p-nitrochlorobenzene is controlled to be 620g/h, and the flow rate of the sodium hydroxide solution is controlled to be 5150g/h;
and step three, cooling and crystallizing the obtained reaction liquid to obtain the sodium p-nitrophenolate.
Wherein the mass fraction of the sodium hydroxide solution is 6 percent; the dosage mass ratio of the nitrochlorobenzene to the quaternary ammonium salt surfactant is 10:1; the molar ratio of the nitrochlorobenzene to the sodium hydroxide is 1:1.8. the quaternary ammonium surfactant was prepared as in example 2.
Example 6
Firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 165 ℃, controlling the pressure to be 0.8MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and preheating the p-nitrochlorobenzene and a sodium hydroxide solution to 155 ℃;
secondly, feeding, wherein the flow of the p-nitrochlorobenzene is controlled to be 640g/h and the flow of the sodium hydroxide solution is 5200g/h during feeding;
and step three, cooling and crystallizing the obtained reaction liquid to obtain the p-nitrophenol sodium.
Wherein the mass fraction of the sodium hydroxide solution is 8 percent; the dosage mass ratio of the nitrochlorobenzene to the quaternary ammonium salt surfactant is 100:11; the molar ratio of the nitrochlorobenzene to the sodium hydroxide is 1:1.9. the quaternary ammonium surfactant was prepared as in example 2.
Comparative example 1
The quaternary ammonium salt surfactant in example 5 was not added, and the remaining raw materials and preparation process remained unchanged.
The yields and purities of the products of examples 4-6 and comparative example 1 were recorded, and the results are shown in table 1 below:
TABLE 1
Item | Example 4 | Example 5 | Example 6 | Comparative example 1 |
Yield% | 92.21 | 92.91 | 91.82 | 85.12 |
Purity% | 99.14 | 99.22 | 99.16 | 80.31 |
From the above table 1, it can be seen that the yield and purity of the product are kept stable under the condition of reducing the amount of alkali by adding the quaternary ammonium surfactant in the process of preparing the sodium p-nitrophenolate.
In the description herein, references to the description of "one embodiment," "an example," "a specific example" or the like are intended to mean that a particular feature, structure, material, or characteristic described in connection with the embodiment or example is included in at least one embodiment or example of the invention. In this specification, the schematic representations of the terms used above do not necessarily refer to the same embodiment or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments or examples.
The foregoing is illustrative and explanatory only, and it will be appreciated by those skilled in the art that various modifications, additions and substitutions can be made to the embodiments described without departing from the scope of the invention as defined in the appended claims.
Claims (3)
1. A synthetic process of p-nitrophenol sodium is characterized by comprising the following steps:
firstly, introducing nitrogen into a reaction kettle, preheating the reaction kettle to 160-165 ℃, controlling the pressure to be 0.75-0.8MPa, adding a quaternary ammonium salt surfactant into p-nitrochlorobenzene, and preheating the p-nitrochlorobenzene and a sodium hydroxide solution to 150-155 ℃;
secondly, feeding, wherein the flow of the p-nitrochlorobenzene is controlled to be 600-640g/h and the flow of the sodium hydroxide solution is 5100-5200g/h during feeding;
step three, cooling and crystallizing the obtained reaction liquid to obtain p-nitrophenol sodium;
the quaternary ammonium salt surfactant has the following structure:
the quaternary ammonium salt surfactant is prepared by the following steps:
s11, mixing sodium sulfite and deionized water to prepare a saturated solution, setting the temperature to be 85 ℃, dropwise adding epoxy chloropropane, controlling the dropwise adding time to be 1.5-2h, keeping the temperature unchanged after the dropwise adding is finished, continuing to react for 1.5h, and performing post-treatment after the reaction is finished to obtain an intermediate 1;
s12, mixing xylene and diethylenetriamine, setting the temperature to be 90 ℃, dropwise adding the mixed xylene and diethylenetriamine into benzoic acid, continuously heating to 140-150 ℃ after dropwise adding is finished, continuously reacting for 3 hours at the temperature, then heating to 240 ℃, continuously reacting for 3 hours, and obtaining an intermediate 2 after the reaction is finished;
and S13, cooling the intermediate 2 obtained in the step S12 to 80 ℃, adding the intermediate 1, and continuously stirring for reaction for 4 hours to obtain the quaternary ammonium surfactant.
2. The process for synthesizing sodium p-nitrophenolate according to claim 1, wherein the molar ratio of the sodium sulfite to the epichlorohydrin in step S11 is 1.2:1; in the step S12, the dosage ratio of the dimethylbenzene to the diethylenetriamine to the benzoic acid is 20mL:1g:1.4g; in the step S13, the mass ratio of the intermediate 2 to the intermediate 1 is 1:1.
3. the process for synthesizing sodium p-nitrophenolate according to claim 1, wherein the mass fraction of the sodium hydroxide solution is 4-8%; the dosage mass ratio of the nitrochlorobenzene to the quaternary ammonium salt surfactant is 100:9-11; the molar ratio of the nitrochlorobenzene to the sodium hydroxide is 1:1.7-1.9.
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB902306A (en) * | 1958-05-16 | 1962-08-01 | Monsanto Chemicals | Production of nitrophenetoles |
FR1497888A (en) * | 1966-10-27 | 1967-10-13 | Universal Oil Prod Co | Process for preparing nitrophenols |
US4329503A (en) * | 1980-01-23 | 1982-05-11 | Cassella Aktiengesellschaft | Process for the preparation of 2-amino-4-nitrophenol |
CN1613843A (en) * | 2004-09-02 | 2005-05-11 | 江苏扬农化工集团有限公司 | Preparation of p-nitrophenoxide sodium |
CN111004126A (en) * | 2020-01-22 | 2020-04-14 | 珠海派锐尔新材料有限公司 | Preparation method of p-nitrophenol sodium salt |
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 |
-
2021
- 2021-05-17 CN CN202110535972.0A patent/CN113200862B/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB902306A (en) * | 1958-05-16 | 1962-08-01 | Monsanto Chemicals | Production of nitrophenetoles |
FR1497888A (en) * | 1966-10-27 | 1967-10-13 | Universal Oil Prod Co | Process for preparing nitrophenols |
US4329503A (en) * | 1980-01-23 | 1982-05-11 | Cassella Aktiengesellschaft | Process for the preparation of 2-amino-4-nitrophenol |
CN1613843A (en) * | 2004-09-02 | 2005-05-11 | 江苏扬农化工集团有限公司 | Preparation of p-nitrophenoxide sodium |
CN111004126A (en) * | 2020-01-22 | 2020-04-14 | 珠海派锐尔新材料有限公司 | Preparation method of p-nitrophenol sodium salt |
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 |
Non-Patent Citations (1)
Title |
---|
对硝基苯甲醚合成工艺研究;陈珏;《工业技术》;20121231(第27期);65-67 * |
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