CN115572246A - Process for preparing benzenesulfonic acid by taking hydrogen chloride gas as acidification reagent - Google Patents
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- CN115572246A CN115572246A CN202211209395.7A CN202211209395A CN115572246A CN 115572246 A CN115572246 A CN 115572246A CN 202211209395 A CN202211209395 A CN 202211209395A CN 115572246 A CN115572246 A CN 115572246A
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
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- C07—ORGANIC CHEMISTRY
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- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
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- C07C303/44—Separation; Purification
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Abstract
The invention provides a process for preparing benzenesulfonic acid by using hydrogen chloride gas as an acidification reagent, which comprises the following steps of acidification, centrifugation, concentration, decolorization, evaporation and the like: the concentration of the anhydrous benzenesulfonic acid product obtained by the method is more than 99.0%, and the yield of the benzenesulfonic acid product is more than 90%, the method takes sodium benzenesulfonate as a raw material, takes high-purity hydrogen chloride gas as an acidifying reagent, carries out acidification synthesis reaction in a pure water solvent, and prepares an anhydrous benzenesulfonic acid finished product by carrying out solid-liquid separation, concentration, decoloration and evaporation on an acidification reaction solution; has the advantages of high product yield, good product quality, little environmental pollution, low raw material cost and the like.
Description
Technical Field
The invention relates to the technical field of chemical product preparation processes, in particular to a process for preparing benzenesulfonic acid by taking hydrogen chloride gas as an acidification reagent.
Background
Benzenesulfonic acid, colorless needle-like or plate-like crystals of formula C 6 H 6 O 3 And S. Molecular weight 58.18; the benzenesulfonic acid containing 1.5 molecules of crystal water is easy to deliquesce, and the melting point of the benzenesulfonic acid is 43-44 ℃; melting point 65-66 deg.c (anhydrous), easy to dissolve in water, alcohol, benzene, ether and xyleneCarbon sulfide; benzenesulfonic acid is a strong organic acid, acidic like sulfuric acid, ka =2 × 10-1 (25 ℃), which often becomes sodium salt upon separation and storage; reaction with a base to form a salt, -SO 3 When H is used as a meta-position group for electrophilic substitution, the second group enters a meta position, for example, 72 percent of m-nitrobenzenesulfonic acid can be obtained during nitration, and the sodium salt of the m-nitrobenzenesulfonic acid is melted with NaOH to obtain phenol; the hot steam reacts with the catalyst under the catalysis of acid to generate benzene and FeCl 3 An orange precipitate resulted.
The sulfonic group of the benzenesulfonic acid can be substituted by various groups, and is subjected to alkali fusion with sodium hydroxide to generate sodium phenolate; reacting with sodium cyanide to generate cyanophenyl; reacting with bromine to generate bromobenzene; reacting with nitric acid to generate nitrobenzene; removing sulfonic acid group by heating with water. Used for preparing phenol and resorcinol; it is commonly used as catalyst and water absorbent in esterification and dehydration reactions, and has the advantages of weaker oxidizing property than sulfuric acid and capability of reducing side reactions.
The sulfonic acid group in the benzenesulfonic acid is a strong water-soluble strong acid group and is a water-soluble strong acid compound. The sulfonic acid group in the benzene sulfonic acid molecule can be replaced by hydroxyl and cyano, and is an important intermediate for preparing phenol and nitrile;
the-H part in the molecule of the benzenesulfonic acid can be substituted by halogen atoms, amino groups and the like, and the application is great in organic synthesis; benzenesulfonic acid can be prepared by sulfonation of aromatic hydrocarbons, or oxidation of mercaptans; the prior benzene sulfonic acid production method generally has the process defects of complicated steps, low yield, high cost, large wastewater quantity and the like, and is difficult to obtain high-purity anhydrous benzene sulfonic acid with the content of more than 99.0 percent in electronic grade.
Disclosure of Invention
Aiming at the defects in the prior art, the invention provides a process for preparing benzenesulfonic acid by taking hydrogen chloride gas as an acidifying reagent, which solves the problems of complicated steps, low yield, high cost, large waste water amount, limited purity and the like in the prior art.
According to the embodiment of the invention, the process for preparing the benzenesulfonic acid by using the hydrogen chloride gas as the acidifying reagent comprises the following steps of:
s1, dissolving sodium benzenesulfonate in water to prepare a saturated solution, putting the saturated solution into an acidification kettle, stirring while introducing excessive hydrogen chloride gas, heating and continuously refluxing for 10-14h, stopping refluxing and cooling after the acidification liquid is analyzed to be qualified, and centrifuging the acidification liquid to separate sodium chloride to obtain a dilute acid liquid;
s2, putting the dilute acid solution into a concentration kettle, heating and stirring, gradually heating, controlling the temperature to be lower than 140 ℃, cooling and recovering the separated gas phase, stopping heating when the concentration of the solution in the concentration kettle is qualified, and naturally cooling to be lower than 100 ℃ to remove the material to obtain concentrated acid solution;
s3, adding the concentrated acid solution into a decoloring kettle, cooling to normal temperature through a cooling system, and adding activated carbon to stir for decoloring;
s4, vacuumizing the evaporator, then heating, continuously adding the decolored concentrated acid solution, feeding while evaporating, condensing and recycling the separated gas phase, stopping feeding and heating evaporation after the feeding is finished, discharging the finished product acid in the kettle to a slicing machine after the concentration of the material in the kettle is detected to be qualified, and metering, packaging and warehousing the finished product after the finished product is sliced.
Further, the heating temperature in the step S1 is 60-70 ℃, and the temperature is lower than 30 ℃ after cooling
Further, the standard that the analysis in the step S1 is qualified is that the sodium ion concentration is less than 200ppm.
Further, the dilute acid solution obtained by centrifugal separation in the step S1 is placed into a settling pond for natural settling for more than 2 hours, and then is injected into a dilute acid storage tank through a filter for standby.
Further, the qualified concentration standard in the step S2 is that the mass concentration of the concentrated solution is more than or equal to 65%.
Further, the normal temperature in the step S3 is 25 ℃.
Further, the amount of the activated carbon added in the step S3 is positively correlated with the color shade of the concentrated acid solution.
Further, the required vacuum degree in the evaporator in the step S4 is below 3000Pa of ultimate vacuum.
Further, the qualified standard in the step S4 is that the mass concentration of the kettle liquid is greater than 99.0%.
Further, in the step S4, the qualified finished product is pressed to a slicer by using nitrogen.
The technical principle of the invention is as follows: the invention utilizes the principle of ion dissolution balance in the solution, and when the hydrogen chloride gas is continuously introduced into the saturated sodium benzenesulfonate solution, chloride ions are introduced into the solution; because the solubility of the hydrogen chloride is higher than that of the sodium chloride, when the concentration of chloride ions in the solution is increased, the dissolution balance of the sodium chloride is pushed to move towards the crystallization direction, and when the concentration of the chloride ions is saturated, sodium chloride crystals are separated out so as to reduce the concentration of the chloride ions in the solution and avoid losing balance; and (3) continuously precipitating and separating sodium chloride in the solution along with the continuous introduction of the hydrogen chloride gas until all sodium ions are discharged in a precipitation form, only the benzenesulfonic acid and the hydrogen chloride are left in the solution, and separating the hydrogen chloride by distillation at the moment to obtain the high-concentration benzenesulfonic acid.
Compared with the prior art, the invention has the following beneficial effects:
the invention takes sodium benzene sulfonate as raw material, takes high-purity hydrogen chloride gas as acidifying reagent, carries on the acidification synthesis reaction in pure water solvent, the acidification reaction liquid is processed by solid-liquid separation, condensation, decoloration, evaporation to obtain the finished product of anhydrous benzene sulfonic acid; has the advantages of high product yield, good product quality, little environmental pollution, low raw material cost and the like.
Drawings
FIG. 1 is a process flow diagram of an embodiment of the present invention.
Detailed Description
The technical solution of the present invention is further explained with reference to the drawings and the embodiments.
Example 1:
(1) Preparing sodium benzenesulfonate into a saturated solution with the actual mass concentration of 40% by using pure water as a solvent, metering the saturated solution into an acidification kettle, simultaneously starting the acidification kettle for stirring, opening a jacket cooling water inlet and outlet valve, metering and introducing hydrogen chloride gas, controlling the acidification reaction temperature to perform reflux reaction at 60 ℃ for 14 hours, stopping the reflux reaction and cooling to below 30 ℃ after the acidification solution is qualified through central control analysis (sodium ions are less than or equal to 200 ppm), opening a discharge bottom valve, performing solid-liquid centrifugal separation on the acidification solution to obtain sodium chloride, placing the acidification solution into a settling tank for natural settling for 2.5 hours, and pumping the acidification solution into a dilute acid storage tank for use in a next concentration position through a pneumatic diaphragm pump of a precision filter.
(2) The method comprises the steps of measuring a dilute acid liquid from a dilute acid storage tank, putting the dilute acid liquid into a concentration kettle, opening a stirring and jacket heat-conducting oil inlet and outlet valve of the concentration kettle, starting heating, controlling the distillation temperature to be less than 140 ℃ in the concentration process, controlling the vacuum degree, condensing a vapor phase of the concentration kettle through a graphite condenser, then feeding the vapor phase into a recovery tank for recovery and reuse, sampling and analyzing when the distillation temperature of the concentration kettle reaches 140 ℃, closing the jacket heat-conducting oil inlet and outlet valve to stop concentration after sampling and analyzing are qualified (the content of a concentrated solution is more than or equal to 65%), and opening a discharging bottom valve to pump the concentrated acid liquid to a concentrated acid liquid decolorization kettle for later use when the temperature is naturally reduced to be below 100 ℃.
(3) Opening a stirring and jacket cooling water inlet and outlet valve of a concentrated acid solution decoloring kettle, starting cooling, adding activated carbon in a proper amount according to the practical appearance color condition of the concentrated acid solution for decoloring when the concentrated acid solution is cooled to the normal temperature of 25 ℃, and opening a discharging bottom valve to press the concentrated acid solution to a concentrated acid solution head tank for use in the next evaporation post through compressed air by a precision filter after the decoloring treatment.
(4) Firstly, a Roots vacuum pump unit for a wiped film evaporator is used for pumping the vacuum degree to be below the limit vacuum of 3000Pa, then the jacket heat conducting oil of the wiped film evaporator and a steam inlet and outlet valve of a heat preservation system are opened for preheating and heating, simultaneously, an outlet valve of a concentrated acid head tank is opened for metering and feeding through a flowmeter, in the evaporation process, the vacuum degree, the evaporation temperature and the feeding quantity are strictly controlled, and the vapor phase of the evaporator enters a dilute acid recovery tank for recycling and applying after being condensed by a condenser by adjusting the feeding quantity of the wiped film evaporator; and after feeding is finished, closing a conduction oil inlet and outlet valve of a jacket of the wiped film evaporator, stopping evaporation, performing central control sampling analysis to obtain a qualified product (the concentration of the kettle liquid is more than 99.0%), then opening an outlet bottom valve of the evaporator to press finished acid to a slicing machine by using nitrogen, metering the finished product after being sliced by the slicing machine, entering a finished product packaging barrel, packaging according to a standard, sticking labels, and uniformly handling the finished product for storage.
Example 2:
(1) Preparing sodium benzenesulfonate into a saturated solution with the actual mass concentration of 40% by using pure water as a solvent, metering the saturated solution into an acidification kettle, simultaneously starting the acidification kettle for stirring, opening a jacket cooling water inlet and outlet valve, metering and introducing hydrogen chloride gas, controlling the acidification reaction temperature to carry out reflux reaction at 65 ℃ for 12 hours, stopping the reflux reaction and cooling to below 30 ℃ after the acidification solution is qualified through central control analysis (sodium ions are less than or equal to 200 ppm), opening a discharge bottom valve, carrying out solid-liquid centrifugal separation on the acidification solution to obtain sodium chloride, then placing the acidification solution into a settling tank for natural settling for 3 hours, and pumping the acidification solution into a dilute acid storage tank for use in a next concentration station through a pneumatic diaphragm pump by using a precision filter.
(2) The method comprises the steps of measuring a dilute acid liquid from a dilute acid storage tank, putting the dilute acid liquid into a concentration kettle, opening a stirring and jacket heat-conducting oil inlet and outlet valve of the concentration kettle, starting heating, controlling the distillation temperature to be less than 140 ℃ in the concentration process, controlling the vacuum degree, condensing a vapor phase of the concentration kettle through a graphite condenser, then feeding the vapor phase into a recovery tank for recovery and reuse, sampling and analyzing when the distillation temperature of the concentration kettle reaches 140 ℃, closing the jacket heat-conducting oil inlet and outlet valve to stop concentration after sampling and analyzing are qualified (the content of a concentrated solution is more than or equal to 65%), and opening a discharging bottom valve to pump the concentrated acid liquid to a concentrated acid liquid decolorization kettle for later use when the temperature is naturally reduced to be below 100 ℃.
(3) Opening a stirring and jacket cooling water inlet and outlet valve of a concentrated acid solution decoloring kettle, starting cooling, adding an appropriate amount of activated carbon for decoloring according to the actual appearance color condition of the concentrated acid solution when the concentrated acid solution is cooled to the normal temperature of 25 ℃, and after decoloring, opening a discharge bottom valve to press the concentrated acid solution to a concentrated acid solution head tank by compressed air through a precision filter for use in a next evaporation post.
(4) Firstly, a Roots vacuum pump unit for a wiped film evaporator is used for pumping the vacuum degree to be below the limit vacuum of 3000Pa, then the jacket heat conducting oil of the wiped film evaporator and a steam inlet and outlet valve of a heat preservation system are opened for preheating and heating, simultaneously, an outlet valve of a concentrated acid head tank is opened for metering and feeding through a flowmeter, in the evaporation process, the vacuum degree, the evaporation temperature and the feeding quantity are strictly controlled, and the vapor phase of the evaporator enters a dilute acid recovery tank for recycling and applying after being condensed by a condenser by adjusting the feeding quantity of the wiped film evaporator; and after feeding is finished, closing a conduction oil inlet and outlet valve of a jacket of the wiped film evaporator, stopping evaporation, performing central control sampling analysis to obtain a qualified product (the concentration of the kettle liquid is more than 99.0%), then opening an outlet bottom valve of the evaporator to press finished acid to a slicing machine by using nitrogen, metering the finished product after being sliced by the slicing machine, entering a finished product packaging barrel, packaging according to a standard, sticking labels, and uniformly handling the finished product for storage.
Example 3:
(1) Preparing sodium benzenesulfonate into a saturated solution with the actual mass concentration of 40% by using pure water as a solvent, metering the saturated solution into an acidification kettle, simultaneously starting the acidification kettle for stirring, opening a jacket cooling water inlet and outlet valve, metering and introducing hydrogen chloride gas, controlling the acidification reaction temperature to carry out reflux reaction at 70 ℃ for 10 hours, stopping the reflux reaction and cooling to below 30 ℃ after the acidification solution is qualified through central control analysis (sodium ions are less than or equal to 200 ppm), opening a discharge bottom valve, carrying out solid-liquid centrifugal separation on the acidification solution to obtain sodium chloride, then placing the acidification solution into a settling tank for natural settling for 5 hours, and pumping the acidification solution into a dilute acid storage tank for use in a next concentration station through a pneumatic diaphragm pump by using a precision filter.
(2) The dilute acid liquid is metered from a dilute acid storage tank and is placed into a concentration kettle, stirring of the concentration kettle and a jacket heat-conducting oil inlet/outlet valve are opened, temperature rise is started, the distillation temperature is controlled to be less than 140 ℃ in the concentration process, the vacuum degree is controlled, the vapor phase of the concentration kettle enters a recovery tank for recovery and reuse after being condensed by a graphite condenser, when the distillation temperature of the concentration kettle reaches 140 ℃, sampling analysis is carried out, after the sampling analysis is qualified (the content of the concentrated solution is more than or equal to 65%), the jacket heat-conducting oil inlet/outlet valve is closed to stop concentration, and when the temperature is naturally reduced to be below 100 ℃, a discharge bottom valve is opened to pump the concentrated acid liquid to a concentrated acid liquid decolorization kettle for later use.
(3) Opening a stirring and jacket cooling water inlet and outlet valve of a concentrated acid solution decoloring kettle, starting cooling, adding activated carbon in a proper amount according to the practical appearance color condition of the concentrated acid solution for decoloring when the concentrated acid solution is cooled to the normal temperature of 25 ℃, and opening a discharging bottom valve to press the concentrated acid solution to a concentrated acid solution head tank for use in the next evaporation post through compressed air by a precision filter after the decoloring treatment.
(4) Firstly, a Roots vacuum pump unit for a wiped film evaporator is used for pumping the vacuum degree to be below 3000Pa of the limit vacuum, then, the jacket heat conduction oil of the wiped film evaporator and a steam inlet and outlet valve of a heat insulation system are opened to start preheating and heating, meanwhile, an outlet valve of a concentrated acid head tank is opened to start metering and feeding through a flowmeter, in the evaporation process, the vacuum degree, the evaporation temperature and the feeding quantity are strictly controlled, and the vapor phase of the evaporator enters a dilute acid recovery tank for recycling and using after being condensed by a condenser by adjusting the feeding quantity of the wiped film evaporator; and after feeding is finished, closing a heat-conducting oil inlet and outlet valve of a jacket of the wiped film evaporator, stopping evaporation, after the heat-conducting oil inlet and outlet valve is qualified through central control sampling analysis (the concentration of the kettle liquid is more than 99.0%), opening an outlet bottom valve of the evaporator to press finished product acid to a slicing machine by using nitrogen, metering the finished product after the finished product is sliced by the slicing machine, entering a finished product packaging barrel, packaging according to standards, sticking labels, uniformly handling the finished product and warehousing.
Specific parameters of the benzenesulfonic acid product obtained in the above example are shown in table 1:
TABLE 1
As can be seen from Table 1, the concentration of the anhydrous benzenesulfonic acid product obtained by the method is more than 99.0%, and the yield of the benzenesulfonic acid product is more than 90%, so that the method has the advantages of high product yield and good product quality.
Finally, the above embodiments are only for illustrating the technical solutions of the present invention and not for limiting, although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that modifications or equivalent substitutions may be made to the technical solutions of the present invention without departing from the spirit and scope of the technical solutions of the present invention, and all of them should be covered in the claims of the present invention.
Claims (10)
1. A process for preparing benzenesulfonic acid by using hydrogen chloride gas as an acidifying reagent is characterized by comprising the following steps of:
s1, dissolving sodium benzenesulfonate in water to prepare a saturated solution, putting the saturated solution into an acidification kettle, stirring while introducing excessive hydrogen chloride gas, heating and continuously refluxing for 10-14 hours, stopping refluxing and cooling after the acidification liquid is analyzed to be qualified, and centrifuging the acidification liquid to separate sodium chloride to obtain a dilute acid liquid;
s2, putting the dilute acid solution into a concentration kettle, heating and stirring, gradually heating, controlling the temperature to be lower than 140 ℃, cooling and recovering the separated gas phase, stopping heating when the concentration of the solution in the concentration kettle is qualified, and naturally cooling to be lower than 100 ℃ to remove the material to obtain concentrated acid solution;
s3, adding the concentrated acid solution into a decoloring kettle, cooling to normal temperature through a cooling system, and adding activated carbon to stir for decoloring;
s4, vacuumizing the evaporator, heating, continuously adding decolored concentrated acid liquid, feeding while evaporating, condensing separated gas phase, recycling, stopping feeding and heating evaporation after feeding is finished, discharging finished product acid in the kettle to a slicing machine after the concentration of the material in the kettle is detected to be qualified, and measuring, packaging and warehousing the finished product after the finished product is sliced.
2. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying reagent, wherein: in the step S1, the heating temperature is 60-70 ℃, and the temperature is less than 30 ℃ after cooling.
3. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: the standard that the analysis in the step S1 is qualified is that the concentration of sodium ions is less than 200ppm.
4. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: and (2) placing the dilute acid solution obtained by centrifugal separation in the step (S1) into a sedimentation tank for natural sedimentation for more than 2 hours, and injecting the dilute acid solution into a dilute acid storage tank for later use through a filter.
5. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: the qualified concentration standard in the step S2 is that the mass concentration of the concentrated solution is more than or equal to 65 percent.
6. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: the normal temperature in the step S3 is 25 ℃.
7. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: the amount of the activated carbon added in the step S3 is positively correlated with the color depth of the concentrated acid solution.
8. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: and in the step S4, the required vacuum degree in the evaporator is below 3000 Pa.
9. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: and the qualified detection standard in the step S4 is that the mass concentration of the kettle liquid is more than 99.0%.
10. The process of claim 1 for the preparation of benzenesulfonic acid using hydrogen chloride gas as acidifying agent, wherein: and in the step S4, the qualified finished product is pressed to a slicing machine by using nitrogen.
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