CN109265392B - Method for continuously synthesizing pyridinium hydroxy propane sulfonate - Google Patents
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- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
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Abstract
The invention discloses a method for continuously synthesizing pyridinium hydroxy propane sulfonate, which comprises the following steps: adding phase transfer catalyst and sodium sulfite into alkali metal bisulfite or pyrosulfite solution to obtain solution containing HSO3 ‑Introducing the mixed solution and epoxy chloropropane into a first reactor simultaneously to perform a ring-opening reaction; and simultaneously feeding the mixed solution of pyridine and the catalyst and the ring-opening reaction product into a second reactor for reaction to obtain a target product. The method changes the mixing sequence and the adding sequence of the raw materials, so that the raw materials to participate in the reaction enter the reactor to participate in the corresponding reaction, thereby effectively reducing the occurrence of side reactions, improving the selectivity and the conversion rate of the reaction, further improving the yield and the purity of the product, and meeting the high-end customer requirements of the electroplating industry; compared with the intermittent operation of the traditional process, the method shortens the reaction time, improves the production efficiency and is more suitable for industrial production.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a method for continuously synthesizing pyridinium hydroxypropanesulfonate.
Background
Pyridinium hydroxy propane sulfonate (PPS-OH for short) is an electroplating intermediate, and has a molecular formula as follows: c8H11NaO4S, molecular weight: 217.24, CAS number: 3918-73-8, the pure product is white crystal, and most of the commercial products are colorless to light yellow liquid with the content of 40-50% and the pH value of 3-5. PPS-OH has excellent brightening and leveling effects in nickel electroplating, especially at high current densitiesThe zone leveling effect is excellent. The nickel plating solution is used as a basic additive in the nickel plating bath solution, the dosage of the nickel plating solution is 50-500 mg/L, the consumption of the nickel plating solution is 20-50 g/kAH, and the market demand is large due to the requirements of anticorrosion and decoration functions.
The existing PPS-OH industrial synthesis method is a normal-pressure batch kettle reaction taking hydrosulfite or pyrosulfite, epichlorohydrin and pyridine as raw materials, and the synthesis method is divided into a one-step method and a two-step method. In Chinese patent CN102161639B, PPS-OH is synthesized by a two-step method, and an intermediate 3-chloro-2-hydroxypropanesulfonate is separated and purified and then reacts with pyridine; in the Chinese patent CN103922997B, PPS-OH is synthesized by adopting a one-step method, reaction conditions are effectively controlled by adding an auxiliary sulfonating agent, a phase transfer catalyst and a complexing agent, side reactions are reduced, then pyridine is directly added into a reaction system, PPS-OH is synthesized in one pot, and then an impurity removing agent, a stabilizing agent and active carbon are added for decoloration and impurity removal to obtain a final product. However, the PPS-OH synthesis is performed intermittently in a traditional reactor at present, the production efficiency is low, the subsequent separation process is complicated, the purity of the prepared product is low, the product is yellowish, and the requirements of high-end electroplating customers are difficult to meet.
Disclosure of Invention
The invention aims to overcome the technical defects and provide a method for continuously synthesizing pyridinium hydroxypropanesulfonate, which has continuous process, reduces the occurrence of side reactions, improves the selectivity and the conversion rate of the reaction and improves the yield and the purity of products.
In order to achieve the technical purpose, the technical scheme of the invention provides a method for continuously synthesizing pyridinium hydroxypropanesulfonate, which comprises the following steps: adding phase transfer catalyst and sodium sulfite into alkali metal bisulfite or pyrosulfite solution to obtain solution containing HSO3 -Introducing the mixed solution and epoxy chloropropane into a first reactor simultaneously to perform a ring-opening reaction; and simultaneously feeding the mixed solution of pyridine and the catalyst and the ring-opening reaction product into a second reactor for reaction to obtain a target product.
The reaction principle of the method for synthesizing the pyridinium hydroxy propane sulfonate is as follows:
compared with the prior art, the invention has the beneficial effects that:
1. the method changes the mixing sequence and the adding sequence of the raw materials, so that the raw materials to participate in the reaction enter the reactor to participate in the corresponding reaction, thereby effectively reducing the occurrence of side reactions, improving the selectivity and the conversion rate of the reaction, further improving the yield and the purity of the product, and meeting the high-end customer requirements of the electroplating industry;
2. compared with the intermittent operation of the traditional process, the method shortens the reaction time, improves the production efficiency and is more suitable for industrial production.
Drawings
FIG. 1 is a process flow diagram for the preparation of PPS-OH according to the present invention;
FIG. 2 is an HPLC chromatogram of PPS-OH obtained in example 1 by using the novel process;
FIG. 3 is an HPLC chromatogram of PPS-OH obtained by an old process.
Detailed Description
The embodiment provides a method for continuously synthesizing pyridinium hydroxypropanesulfonate, which comprises the following steps:
(1) dissolving alkali metal bisulfite or pyrosulfite in deionized water, adding phase transfer catalyst and sodium sulfite, stirring and mixing to obtain solution containing HSO3 -The mixed solution is filtered by a membrane and then enters a metering pump, and then the mixed solution containing HSO is filtered by a membrane3 -The mixed liquid and the epoxy chloropropane are simultaneously introduced into a microchannel reactor I, and HSO is carried out3 -Performing ring-opening reaction with epoxy chloropropane at 20-50 ℃;
(2) and (2) adjusting the pressure of the first microchannel reactor to 0.2-5 MPa by adjusting a back pressure valve, enabling the reaction product reacted in the step (1) to enter a second microchannel reactor, simultaneously introducing a mixed solution of pyridine and a catalyst into the second microchannel reactor, enabling the reaction product and the pyridine in the step (1) to react at 50-90 ℃ under the action of the catalyst to generate a target product, adjusting the back pressure valve to enable the pressure of the second microchannel reactor to be 1-5 MPa, and enabling the reacted target product to directly enter a storage tank with a cooling water jacket.
In some preferred embodiments, HSO3-The molar ratio of the epichlorohydrin to the pyridine is 1: 0.98-1: 0.97-1, namely if the raw material is alkali metal pyrosulfite, the molar ratio of the alkali metal pyrosulfite to the epichlorohydrin to the pyridine is 0.5: 0.98-1: 0.97-1; if the raw material is alkali metal hydrosulfite, the molar ratio of the alkali metal hydrosulfite to the epoxy chloropropane to the pyridine is 1: 0.98-1: 0.97-1; within the dosage ratio range, the occurrence of side reactions can be effectively reduced, and the waste of raw materials and the treatment of solid wastes can be reduced.
In some preferred embodiments, the amount of sodium sulfite is 0.1 to 5% by mass of the alkali metal bisulfite or metabisulfite.
In some preferred embodiments, the total mass of the phase transfer catalyst is 0.01 to 0.05% of the mass of the alkali metal bisulfite or metabisulfite; within the dosage range, the selectivity of generating the 3-chloro-2-hydroxypropane sulfonate by the ring-opening reaction can be improved, and the waste of the phase transfer catalyst is reduced.
In some preferred embodiments, the phase transfer catalyst is at least one of NP-21, triethylbenzylammonium chloride, triethylbenzylammonium bromide, tetrabutylammonium chloride, and tetrabutylammonium bromide.
In some preferred embodiments, the catalyst in step (2) is 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadec-2-ene, and the 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadec-2-ene is used in an amount of 0.1-2% by mass of pyridine; within the dosage range, the subsequent treatment of solid waste can be reduced.
In some preferred embodiments, the temperature of the ring-opening reaction in the microchannel reactor I is 30 ℃ and the pressure is 2.5 MPa.
In some preferred embodiments, the reaction product of the second microchannel reactor and pyridine are reacted at a temperature of 70 ℃ and a pressure of 3 MPa.
In some preferred embodiments, in the I microchannel reactor, HSO3 is contained-The flow rate of the mixed liquid is 80-100 g/min, and the flow rate of the epoxy chloropropane is 23-26 g/min; in the II micro-channel reactor, the flow rate of the mixed liquid of pyridine and catalyst is 21-22 g/min.
The two reactors in the method of the invention are preferably microchannel reactors, more preferably T-shaped microchannel reactors, so that the whole reaction process is continuously carried out in a microchannel reaction system; the metering pump adopts a high-precision plunger metering pump; by adopting the microchannel reactor and the high-precision plunger metering pump, the precision of the feeding proportion is optimized, the raw material cost is saved, and the discharge of three wastes is reduced; the reaction time is greatly shortened, so that the reaction which needs to be finished for more than ten hours is finished within a few minutes, the production efficiency and the productivity are improved, and the energy consumption is also reduced.
The DCS control system is used for controlling the process parameters such as the sample volume, the reaction temperature, the reaction pressure and the like of each material in the whole reaction system, so that the process parameters in the reaction process can be accurately controlled, and the occurrence of side reactions is effectively reduced.
In the preferred embodiment of the invention, the reaction temperature, the reaction pressure and the reaction time of material contact in the reaction process are adjusted by adjusting the reaction temperature, the reaction pressure and the flow of the raw materials, the selectivity and the conversion rate of the reaction are further improved, the defect that the raw materials and the products are easy to discolor in the high-temperature oxidation and de-pyridine processes is overcome by adopting a low-temperature high-pressure closed feeding mode, and the inert gas protection and active carbon de-coloring procedures are also omitted.
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. Because of the price advantage of sodium metabisulfite, the patent of the present invention is described below by way of example only with reference to sodium metabisulfite as the reaction raw material, it being understood that the specific examples described herein are intended to be illustrative of the present invention only and are not intended to be limiting.
Example 1:
dissolving 2000g sodium pyrosulfite in 5450g deionized water, adding 2g sodium sulfite and 0.2g tetrabutylammonium bromide into the sodium pyrosulfite solution after the sodium pyrosulfite is completely dissolved, stirring and mixing uniformly, and then mixing the mixture containing HSO3-The mixed solution is filtered by a membrane and then enters a metering pump, and the mixed solution containing HSO3 is filtered by a membrane-The mixed solution is simultaneously introduced into a first microchannel reactor at the speed of 100g/min and 1910g of epoxy chloropropane at the speed of 25.63g/min, the reaction temperature in the first microchannel reactor is adjusted to 50 ℃, a back pressure valve is adjusted to stabilize the pressure of the first microchannel reactor at 2MPa, then a reaction product in a first reaction unit of the microchannel reactor enters a second microchannel reactor, simultaneously a mixed solution of 1620g of pyridine and 1.62g of 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadec-2-ene is introduced into the second microchannel reactor at the feeding speed of 21.76g/min, the reaction temperature in a second reaction unit of the microchannel reactor is adjusted to 70 ℃, the back pressure of the second microchannel reactor is adjusted to 3MPa by the back pressure valve, and the reacted materials directly enter a storage tank with a cooling water jacket, a colorless, clear and transparent liquid was obtained.
The sample was analyzed and detected by HPLC, and the product prepared by the method of this example had a purity of 99.94%, a yield of 99%, a chromaticity of 15# (platinum-cobalt colorimetric method), and was qualified in the hall cell test piece.
Example 2:
dissolving 2000g sodium pyrosulfite in 5450g deionized water, adding 5g sodium sulfite and 0.4g tetrabutylammonium bromide into the sodium pyrosulfite solution after the sodium pyrosulfite is completely dissolved, stirring and mixing uniformly, and then mixing the mixture containing HSO3-The mixed solution is filtered by a membrane and then enters a metering pump, and the mixed solution containing HSO3 is filtered by a membrane-The mixed solution is simultaneously introduced into a first microchannel reactor at the speed of 100g/min and the speed of 1910g of epichlorohydrin of 25.62g/min, the reaction temperature in the first microchannel reactor is adjusted to 30 ℃, a back pressure valve is adjusted to stabilize the pressure of the first microchannel reactor to 2.5MPa, then the reaction product in the first microchannel reactor enters a second microchannel reactor, and 21.77g/min is simultaneously used for introducing the reaction product into the second microchannel reactorIntroducing a mixed solution of 1620g of pyridine and 3g of 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadecan-2-ene into a second microchannel reactor at a feeding speed, adjusting the reaction temperature in a second reaction unit of the microchannel reactor to 50 ℃, adjusting a back pressure valve to ensure that the pressure of the second microchannel reactor is 3.5MPa, and directly feeding the reacted material into a storage tank with a cooling water jacket to obtain colorless, clear and transparent liquid.
The sample was analyzed and detected by HPLC, and the purity of the product prepared by the method of this example was 99.86%, the yield thereof reached 98.86%, the chromaticity was 15# (platinum cobalt colorimetry), and the hall cell test piece was qualified.
Example 3:
dissolving 2000g sodium metabisulfite in 5450g deionized water, adding 3g sodium sulfite and 0.4g tetrabutylammonium bromide into sodium metabisulfite solution after completely dissolving, stirring and mixing uniformly, and mixing with HSO3-The mixed solution is filtered by a membrane and then enters a metering pump, and the mixed solution containing HSO3 is filtered by a membrane-The mixed solution is simultaneously introduced into a first microchannel reactor at the speed of 90g/min and 1948g of epichlorohydrin at the speed of 23g/min, the reaction temperature in the first microchannel reactor is adjusted to 30 ℃, a back pressure valve is adjusted to stabilize the pressure of the first microchannel reactor at 2.5MPa, the reaction product in the first microchannel reactor enters a second microchannel reactor, a mixed solution of 1665g of pyridine and 3g of 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadec-2-ene is simultaneously introduced into the second microchannel reactor at the feeding speed of 22g/min, the reaction temperature in the second microchannel reactor is adjusted to 50 ℃, the back pressure valve is adjusted to make the pressure of the second microchannel reactor at 3.5MPa, and the reacted material directly enters a storage tank with a cooling water jacket, a colorless, clear and transparent liquid was obtained.
The sample was analyzed and detected by HPLC, and the product prepared by the method of this example had a purity of 99.76%, a yield of 99.1%, a chromaticity of 15# (platinum-cobalt colorimetric method), and was qualified in the hall cell test piece.
Example 4:
2000g of sodium metabisulfite are dissolved in 4000g of deionised waterAdding 5g of sodium sulfite and 0.4g of tetrabutylammonium bromide into sodium metabisulfite solution after the sodium metabisulfite is completely dissolved in water, stirring and mixing uniformly, and then adding 3 containing HSO-The mixed solution is filtered by a membrane and then enters a metering pump, and the mixed solution containing HSO3 is filtered by a membrane-The mixed solution is simultaneously introduced into a first microchannel reactor at the speed of 80g/min and 1910g of epoxy chloropropane at the speed of 25g/min, the reaction temperature in the first microchannel reactor is adjusted to 20 ℃, a back pressure valve is adjusted to stabilize the pressure of the first microchannel reactor at 2.5MPa, a reaction product in the first microchannel reactor enters a second microchannel reactor, simultaneously, a mixed solution of 1620g of pyridine and 3g of 1,4,7, 13-tetraoxa-10-aza-2, 3-benzocyclopentadec-2-ene is introduced into the second microchannel reactor at the feeding speed of 21.2g/min, the reaction temperature in the second microchannel reactor is adjusted to 80 ℃, the back pressure valve is adjusted to make the pressure of the second microchannel reactor at 3.5MPa, and the reacted material directly enters a storage tank with a cooling water jacket, a colorless, clear and transparent liquid was obtained.
The sample was analyzed and detected by HPLC, and the product obtained by the method of this example had a purity of 99.12%, a yield of 96.35%, a color number of # 20 (platinum-cobalt colorimetry), and slight fogging in the high region detected by the hall cell strip.
The HPLC chromatogram of PPS-OH obtained by the new process (method in example 1) is shown in FIG. 2, and the HPLC chromatogram of PPS-OH obtained by the old process (method in patent CN 103922997B) is shown in FIG. 3; as can be seen from FIGS. 2 and 3, only 2 sets of retained peaks appear in FIG. 2, 4 sets of retained peaks appear in FIG. 3, and the PPS-OH concentration in FIG. 2 is 99.94%, and the PPS-OH concentration in FIG. 3 is 99.02%, indicating that the purity of PPS-OH obtained by the method of example 1 is higher than that of PPS-OH obtained by the conventional method.
The PPS-OH prepared by the two process methods is detected in various properties, and the obtained detection results are shown in Table 1.
TABLE 1
| Detecting items | Standard value | Old process | New process |
| Chroma (APHA) | ≤50# | 30 | 15 |
| Purity (%, HPLC) | ≥98 | 99.02 | 99.94 |
| pH value | 2.0～5.5 | 3.21 | 4.51 |
| Specific gravity (20 ℃, g/cm)3) | 1.26～1.30 | 1.27 | 1.27 |
| Pyridine (ppm) | ＜50 | 45 | 5 |
| Iron ion (ppm) | ＜20 | 18 | 9 |
As can be seen from Table 1, the PPS-OH prepared by the method in example 1 has better performance indexes than the PPS-OH prepared by the method of the old process; the PPS-OH prepared by the two methods is used for electroplating, and the plating layer obtained by the product in the example 1 is bright, has no impurities or pockmarks, and has no fogging phenomenon, but the plating layer obtained by the product in the old process has impurities, and has slight fogging phenomenon in a low current density area.
The invention not only realizes the continuous production of PPS-OH, but also improves the yield and purity of PPS-OH and the quality of products by controlling various process parameters in the reaction process and reasonably utilizing reaction equipment.
The above-described embodiments of the present invention should not be construed as limiting the scope of the present invention. Any other corresponding changes and modifications made according to the technical idea of the present invention should be included in the protection scope of the claims of the present invention.
Claims (2)
1. A method for continuously synthesizing pyridinium hydroxy propane sulfonate is characterized by comprising the following steps: adding phase transfer catalyst and sodium sulfite into alkali metal bisulfite or pyrosulfite solution to obtain solution containing HSO3 -Introducing the mixed solution and epoxy chloropropane into a first reactor simultaneously to perform a ring-opening reaction; simultaneously feeding mixed liquor of pyridine and a catalyst and a ring-opening reaction product into a second reactor, and reacting to obtain a target product; the molar ratio of the bisulfite or the pyrosulfite of the alkali metal to the epoxy chloropropane to the pyridine is 1: 0.98-1: 0.97-1 or 0.5: 0.98-1: 0.97-1; the using amount of the sodium sulfite is 0.1-5% of the mass of the bisulfite or the pyrosulfite of the alkali metal; the phase transfer catalyst is at least one of NP-21, triethylbenzylammonium chloride, triethylbenzylammonium bromide, tetrabutylammonium chloride and tetrabutylammonium bromide, and the dosage of the phase transfer catalyst is 0.01-0.05% of the mass of the bisulfite or the pyrosulfite of the alkali metal; what is needed isThe catalyst is 1,4,7, 13-tetraoxa-10-aza-2, 3-benzo cyclopentadec-2-ene, and the dosage of the catalyst is 0.1-2% of the mass of pyridine; the temperature in the first reactor is 20-50 ℃, and the pressure is 0.2-5 MPa; the temperature in the second reactor is 50-90 ℃, and the pressure is 1-5 MPa; said HSO-containing 3-The flow rate of the mixed liquid is 80-100 g/min, the flow rate of the epoxy chloropropane is 23-26 g/min, and the flow rates of the mixed liquid of pyridine and the catalyst and the ring-opening reaction product are 21-22 g/min; the first reactor and the second reactor are both microchannel reactors.
2. The method for continuously synthesizing pyridinium hydroxypropanesulfonate as claimed in claim 1, wherein the microchannel reactor is a T-shaped microchannel reactor, and the whole reaction process is continuously carried out in the microchannel reaction system.
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