CN109265392A - A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt - Google Patents
A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt Download PDFInfo
- Publication number
- CN109265392A CN109265392A CN201811222926.XA CN201811222926A CN109265392A CN 109265392 A CN109265392 A CN 109265392A CN 201811222926 A CN201811222926 A CN 201811222926A CN 109265392 A CN109265392 A CN 109265392A
- Authority
- CN
- China
- Prior art keywords
- reaction
- sulfonic acid
- propane sulfonic
- pyridinium salt
- hydroxy propane
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D213/20—Quaternary compounds thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The invention discloses a kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt, includes the following steps: that phase transfer catalyst and sodium sulfite are added into the bisulfites or pyrosulfurous acid salting liquid of alkali metal, HSO must be contained3 ‑Mixed liquor, the mixed liquor and epoxychloropropane are passed through in first reactor simultaneously, ring-opening reaction occurs；The mixed liquor of pyridine and catalyst, ring-opening reaction product enter in second reactor simultaneously, and reaction obtains target product.Method of the invention changes order by merging and the addition sequence of raw material, make the raw material that participate in reaction while entering the corresponding reaction of reactor participation, it is effectively reduced the generation of side reaction, improve the selectivity and conversion ratio of reaction, and then the yield and purity of product are improved, it is able to satisfy electroplating industry high-end customer demand；Compared with the intermittent operation of traditional handicraft, method of the invention shortens the reaction time, improves production efficiency, industrialized production preferably.
Description
Technical field
The present invention relates to technical field of organic synthesis, and in particular to a kind of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt
Method.
Background technique
Pyridinium hydroxy propyl sulfobetaine (abbreviation PPS-OH), it is a kind of electroplating intermediate, molecular formula are as follows:
C8H11NaO4S, molecular weight: 217.24, No. CAS: 3918-73-8, sterling is white crystal, and commercial product is largely content
Between 40~50%, pH value 3~5 it is colourless to weak yellow liquid.PPS-OH in electronickelling with excellent light and
Leveling effect especially flattens excellent in high current density region.As the base additive in nickel plating bath, dosage is
50~500mg/L, consumption is 20~50g/kAH, because of anti-corrosion and decoration functions demand, the huge market demand.
The Industrialized synthesis method of PPS-OH is with bisulfites or pyrosulfite, epoxychloropropane, pyrrole at present
Pyridine is the atmosphere intermission still reaction of raw material, which is divided into one-step method and two-step method.Chinese patent CN102161639B
It is middle that PPS-OH is synthesized using two-step method, first the separation of intermediate 3- chlorine-2-hydroxyl propane sulfonic acid salt is reacted with pyridine again after purification；In
One-step synthesis method PPS-OH is used in state patent CN103922997B, passes through addition auxiliary sulfonating agent, phase transfer catalyst and network
Mixture effectively controls reaction condition, reduces side reaction, and pyridine, one-pot synthesis PPS- are then directly added into reaction system
Then OH adds cleaner, stabilizer and decolorization and impurity removal by active carbon and obtains final products, this method and two-step synthesis method phase
Than effectively reducing three wastes discharge amount while ensureing product quality.It but is at present tradition about the synthesis of PPS-OH
The intermittent operation carried out in reactor, production efficiency is low, and subsequent separation process is cumbersome, and product purity obtained is lower, and produces
Product are in yellowish, it is difficult to meet the needs of high-end plating client.
Summary of the invention
It is an object of the invention to overcome above-mentioned technical deficiency, a kind of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt is provided
Method, this method process is continuous, reduces the generation of side reaction, improves the selectivity and conversion ratio of reaction, improves production
The yield and purity of product.
To reach above-mentioned technical purpose, technical solution of the present invention provides a kind of continuous synthesis of hydroxy propane sulfonic acid pyridinium
The method of salt includes the following steps: that phase transfer catalyst is added into the bisulfites or pyrosulfurous acid salting liquid of alkali metal
And sodium sulfite, HSO must be contained3 -Mixed liquor, the mixed liquor and epoxychloropropane are passed through in first reactor simultaneously, sent out
Raw ring-opening reaction；The mixed liquor of pyridine and catalyst, ring-opening reaction product enter in second reactor simultaneously, and reaction obtains target
Product.
The reaction principle of method synthesis of hydroxy propane sulfonic acid pyridinium salt method of the invention are as follows:
Compared with prior art, the beneficial effect comprise that
1, method of the invention changes order by merging and the addition sequence of raw material, make to participate in the raw material of reaction simultaneously into
Enter reactor and participate in corresponding reaction, is effectively reduced the generation of side reaction, improves the selectivity and conversion ratio of reaction, into
And the yield and purity of product are improved, it is able to satisfy electroplating industry high-end customer demand；
2, for method of the invention compared with the intermittent operation of traditional handicraft, method of the invention shortens the reaction time,
Improve production efficiency, industrialized production preferably.
Detailed description of the invention
Fig. 1 is the process flow chart that the present invention prepares PPS-OH；
Fig. 2 is the HPLC spectrogram of the PPS-OH to adopt new technology in embodiment 1；
Fig. 3 is the HPLC spectrogram of the PPS-OH obtained using old technique.
Specific embodiment
A kind of method for present embodiments providing continuous synthesis of hydroxy propane sulfonic acid pyridinium salt, includes the following steps:
(1) in deionized water after completely dissolution by the bisulfites of alkali metal or pyrosulfite, into solution plus
Enter phase transfer catalyst and sodium sulfite, after being uniformly mixed, HSO will be contained3 -Mixed liquor by film filter after enter metering
Pump, then HSO will be contained3 -Mixed liquor and epoxychloropropane simultaneously be passed through in I micro passage reaction, HSO3 -And epoxychloropropane
Ring-opening reaction is carried out at 20~50 DEG C；
(2) make the pressure of I micro passage reaction to 0.2~5MPa by adjusting counterbalance valve, make completely reacted in step (1)
Reaction product enter Section II micro passage reaction, while the mixing of pyridine and catalyst is passed through into Section II micro passage reaction
Liquid, reaction product and pyridine in step (1) generate target products in 50~90 DEG C of reactions under the effect of the catalyst, adjust back
Pressure valve makes 1~5MPa of pressure of Section II micro passage reaction, and completely reacted target product is made to be directly entered band cooling water jecket
Storage tank in.
In some preferred embodiments, HSO3-, epoxychloropropane and pyridine molar ratio be 1:0.98~1:0.97~
1, even raw material is the pyrosulfite of alkali metal, then the molar ratio of the pyrosulfite of alkali metal, epoxychloropropane and pyridine
For 0.5:0.98~1:0.97~1；If raw material is the bisulfites of alkali metal, bisulfites, the epoxy chlorine of alkali metal
The molar ratio of propane and pyridine is 1:0.98~1:0.97~1；Within the scope of the amount ratio, the hair of side reaction can be effectively reduced
The processing of waste and solid waste raw, that reduce raw material.
In some preferred embodiments, the dosage of sodium sulfite is the bisulfites or pyrosulfite matter of alkali metal
The 0.1~5% of amount.
In some preferred embodiments, the gross mass of phase transfer catalyst is the bisulfites or burnt sulfurous of alkali metal
The 0.01~0.05% of hydrochlorate quality；In this amount ranges, ring-opening reaction can be improved and generate 3- chlorine-2-hydroxyl propane sulfonate
Selectivity, and reduce the waste of phase transfer catalyst.
In some preferred embodiments, phase transfer catalyst NP-21, triethyl benzyl ammonia chloride, triethylbenzyl
At least one of ammonium bromide, tetrabutylammonium chloride and tetrabutylammonium bromide.
In some preferred embodiments, the catalyst in step (2) is Isosorbide-5-Nitrae, 7,13- tetra- oxa- -10- azepines -2,3-
15-2- alkene of benzo ring, and Isosorbide-5-Nitrae, the dosage of 7,13- tetra- oxa--10- azepine-2,3- benzo ring, 15-2- alkene are pyridine quality
0.1~2%；In this amount ranges, the processing of subsequent solid waste can be reduced.
In some preferred embodiments, the temperature of ring-opening reaction is 30 DEG C in I micro passage reaction, pressure
2.5MPa。
In some preferred embodiments, the reaction product of Section II micro passage reaction and the reaction temperature of pyridine are 70
DEG C, pressure 3MPa.
In some preferred embodiments, in I micro passage reaction, contain HSO3-Mixed liquor flow be 80~
100g/min, the flow of epoxychloropropane are 23~26g/min；In Section II micro passage reaction, pyridine and catalyst it is mixed
The flow for closing liquid is 21~22g/min.
Two preferred micro passage reactions of reactor in method of the invention are more preferably answered using T-type microchannel plate
Device is carried out continuously entire reaction process in the reaction system of microchannel；Metering pump uses high-precision plunger metering pump；By adopting
With micro passage reaction and high-precision plunger metering pump, the precision of charge ratio is optimized, cost of material has been saved, reduces three
Useless discharge；The time for greatly shortening reaction needs the reaction completed in more than ten hour to complete in a few minutes before being allowed to,
Production efficiency and production capacity are improved, energy consumption is also reduced.
The present invention controls the sample volume of each material, reaction temperature, reaction pressure in entire reaction system by DCS control system
The technological parameters such as power can accurately control the technological parameter in reaction process, effectively reduce the generation of side reaction.
In a preferred embodiment of the invention, it by adjusting the flow of reaction temperature, pressure and raw material, has adjusted anti-
Reaction time, reaction temperature and the pressure that material contacts during answering, further improve the selectivity and conversion ratio of reaction, adopt
With cryogenic high pressure closed-type feed mode, raw material is overcome, the drawback that product high-temperature oxydation changes colour and de- pyridine process is easy to change,
Save inert gas shielding and active carbon bleaching process.
In order to make the objectives, technical solutions, and advantages of the present invention clearer, with reference to the accompanying drawings and embodiments, right
The present invention is further elaborated.It is only right by taking it is reaction raw materials as an example below due to the price advantage of sodium pyrosulfite
The invention patent is explained, it should be understood that the specific embodiments described herein are merely illustrative of the present invention, is not used to
Limit the present invention.
Embodiment 1:
2000g sodium pyrosulfite is dissolved in 5450g deionized water, it is molten to sodium pyrosulfite after it is completely dissolved
2g sodium sulfite, 0.2g tetrabutylammonium bromide are added in liquid, after being uniformly mixed, HSO3 will be contained-Mixed liquor pass through film mistake
Enter metering pump after filter, then HSO3 will be contained-Mixed liquor with the speed of 100g/min, 1910g epoxychloropropane with 25.63g/
The speed of min is passed through in I micro passage reaction simultaneously, and the reaction temperature in I micro passage reaction is adjusted to 50 DEG C, is adjusted
Counterbalance valve stablizes the pressure of I micro passage reaction after 2MPa, produces the reaction in micro passage reaction I reaction member
Object enters Section II micro passage reaction, while being passed through with the charging rate of 21.76g/min into Section II micro passage reaction
1620g pyridine and 1.62g Isosorbide-5-Nitrae, the mixed liquor of 7,13- tetra- oxa--10- azepine-2,3- benzo ring, 15-2- alkene, by microchannel
Reaction temperature in reactor Section II reaction member is adjusted to 70 DEG C, and adjusting counterbalance valve makes the pressure of Section II micro passage reaction
3MPa is directly entered completely reacted material in the storage tank with cooling water jecket, obtains colourless, clear liquid.
Sampling uses the purity of product made from the method for the present embodiment for 99.94%, yield through HPLC analysis detection
Reach yield 99%, coloration is 15# (platinum-cobalt method), and slot test piece detection in Hull is qualified.
Embodiment 2:
2000g sodium pyrosulfite is dissolved in 5450g deionized water, it is molten to sodium pyrosulfite after it is completely dissolved
5g sodium sulfite, 0.4g tetrabutylammonium bromide are added in liquid, after being uniformly mixed, HSO3 will be contained-Mixed liquor pass through film mistake
Enter metering pump after filter, then HSO3 will be contained-Mixed liquor with 100g/min speed, 1910g epoxychloropropane with 25.62g/min
Speed is passed through in I micro passage reaction simultaneously, and the reaction temperature in I micro passage reaction is adjusted to 30 DEG C, adjusts back pressure
Valve stablizes the pressure of I micro passage reaction after 2.5MPa, and the reaction product in I micro passage reaction is made to enter Section II
Micro passage reaction, while 1620g pyridine and 3g are passed through into Section II micro passage reaction with the charging rate of 21.77g/min
Micro passage reaction Section II is reacted single by Isosorbide-5-Nitrae, the mixed liquor of 7,13- tetra- oxa--10- azepine-2,3- benzo ring, 15-2- alkene
Reaction temperature in member is adjusted to 50 DEG C, and adjusting counterbalance valve makes the pressure 3.5MPa of Section II micro passage reaction, makes completely reacted
Material is directly entered in the storage tank with cooling water jecket, obtains colourless, clear liquid.
Sampling uses the purity of product made from the method for the present embodiment for 99.86%, yield through HPLC analysis detection
Reach yield 98.86%, coloration is 15# (platinum-cobalt method), and slot test piece detection in Hull is qualified.
Embodiment 3:
2000g sodium pyrosulfite is dissolved in 5450g deionized water, it is molten to sodium pyrosulfite after it is completely dissolved
3g sodium sulfite, 0.4g tetrabutylammonium bromide are added in liquid, after being uniformly mixed, HSO3 will be contained-Mixed liquor pass through film mistake
Enter metering pump after filter, then HSO3 will be contained-Mixed liquor with 90g/min speed, 1948g epoxychloropropane with 23g/min speed
It is passed through in I micro passage reaction simultaneously, the reaction temperature in I micro passage reaction is adjusted to 30 DEG C, adjusting counterbalance valve makes
The pressure of I micro passage reaction is stablized after 2.5MPa, so that the reaction product in I micro passage reaction is entered Section II micro- logical
Road reactor, while 1665g pyridine and 3g Isosorbide-5-Nitrae are passed through into Section II micro passage reaction with the charging rate of 22g/min, 7,
The mixed liquor of tetra- oxa--10- azepine-2,3- benzo ring of 13-, 15-2- alkene, by the reaction temperature in Section II micro passage reaction
50 DEG C are adjusted to, adjusting counterbalance valve makes the pressure 3.5MPa of Section II micro passage reaction, and completely reacted material is made to be directly entered band
In the storage tank of cooling water jecket, colourless, clear liquid is obtained.
Sampling uses the purity of product made from the method for the present embodiment for 99.76%, yield through HPLC analysis detection
Reach yield 99.1%, coloration is 15# (platinum-cobalt method), and slot test piece detection in Hull is qualified.
Embodiment 4:
2000g sodium pyrosulfite is dissolved in 4000g deionized water, it is molten to sodium pyrosulfite after it is completely dissolved
5g sodium sulfite, 0.4g tetrabutylammonium bromide are added in liquid, after being uniformly mixed, HSO3 will be contained-Mixed liquor pass through film mistake
Enter metering pump after filter, then HSO3 will be contained-Mixed liquor with 80g/min speed, 1910g epoxychloropropane with 25g/min speed
It is passed through in I micro passage reaction simultaneously, the reaction temperature in I micro passage reaction is adjusted to 20 DEG C, adjusting counterbalance valve makes
The pressure of I micro passage reaction is stablized after 2.5MPa, so that the reaction product in I micro passage reaction is entered Section II micro- logical
Road reactor, while 1620g pyridine and 3g Isosorbide-5-Nitrae are passed through into Section II micro passage reaction with the charging rate of 21.2g/min,
The mixed liquor of 7,13- tetra- oxa--10- azepine-2,3- benzo ring, 15-2- alkene, by the reaction temperature in Section II micro passage reaction
Degree is adjusted to 80 DEG C, and adjusting counterbalance valve makes the pressure 3.5MPa of Section II micro passage reaction, is directly entered completely reacted material
In storage tank with cooling water jecket, colourless, clear liquid is obtained.
Sampling uses the purity of product made from the method for the present embodiment for 99.12%, yield through HPLC analysis detection
Reach 96.35%, coloration is 20# (platinum-cobalt method), and Hull slot test piece, which detects high area, slight hair mist.
The HPLC spectrogram of PPS-OH that (method in embodiment 1) obtains of adopting new technology is shown in Fig. 2, (specially using old technique
Method in sharp CN103922997B) the obtained HPLC spectrogram of PPS-OH is shown in Fig. 3；By Fig. 2 and Fig. 3 it is found that only occurring in Fig. 2
There are 4 groups of reservation peaks in Fig. 3 in 2 groups of reservation peaks, and the concentration of PPS-OH is the dense of PPS-OH in 99.94%, Fig. 3 in Fig. 2
Degree is 99.02%, illustrates that the purity that PPS-OH is made using the method for the present embodiment 1 is higher than using made from old process
The purity of PPS-OH.
The properties of PPS-OH made from two kinds of processes are detected, obtained testing result is shown in Table 1.
Table 1
| Detection project | Standard value | Old technique | New process |
| Coloration (APHA) | ≤50# | 30 | 15 |
| Purity (%, HPLC) | ≥98 | 99.02 | 99.94 |
| PH value | 2.0~5.5 | 3.21 | 4.51 |
| Specific gravity (20 DEG C, g/cm3) | 1.26~1.30 | 1.27 | 1.27 |
| Pyridine (ppm) | < 50 | 45 | 5 |
| Iron ion (ppm) | < 20 | 18 | 9 |
As shown in Table 1, it is superior to using the performance indexes of PPS-OH made from the method in embodiment 1 using old work
PPS-OH made from the method for skill；And be used to be electroplated by PPS-OH made from two methods, it is obtained using the product in embodiment 1
Coating it is bright, without any impurity or point, also without hair mist phenomenon, but have impurity using the coating that the product of old technique obtains,
There is slight hair mist phenomenon in low current density areas.
The present invention is not only realized by the reasonable utilization of various technological parameters and consersion unit in control reaction process
The continuous production of PPS-OH also improves the quality of the yield of PPS-OH, purity and product.
The above described specific embodiments of the present invention are not intended to limit the scope of the present invention..Any basis
Any other various changes and modifications that technical concept of the invention is made should be included in the guarantor of the claims in the present invention
It protects in range.
Claims (10)
1. a kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt, which comprises the steps of: to alkali metal
Bisulfites or pyrosulfurous acid salting liquid in phase transfer catalyst and sodium sulfite is added, HSO must be contained3 -Mixed liquor,
The mixed liquor and epoxychloropropane are passed through in first reactor simultaneously, ring-opening reaction occurs；The mixing of pyridine and catalyst
Liquid, ring-opening reaction product enter in second reactor simultaneously, and reaction obtains target product.
2. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that the alkali
The bisulfites or pyrosulfite of metal, epoxychloropropane and pyridine molar ratio be 1:0.98~1:0.97~1 or
0.5:0.98~1:0.97~1.
3. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that sulfurous acid
The dosage of sodium be alkali metal bisulfites or pyrosulfurous acid salt quality 0.1~5%.
4. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that the phase
Transfer catalyst is NP-21, triethyl benzyl ammonia chloride, triethylbenzyl ammonium bromide, tetrabutylammonium chloride and tetrabutyl phosphonium bromide
At least one of ammonium, dosage be alkali metal bisulfites or pyrosulfurous acid salt quality 0.01~0.05%.
5. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that described to urge
Agent is Isosorbide-5-Nitrae, and 7,13- tetra- oxa--10- azepine-2,3- benzo ring, 15-2- alkene, dosage is the 0.1~2% of pyridine quality.
6. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that described
Temperature is 20~50 DEG C in one reactor, and pressure is 0.2~5MPa.
7. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that described
Temperature is 50~90 DEG C in two reactors, and pressure is 1~5MPa.
8. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 1, which is characterized in that described to contain
HSO3-The flow of mixed liquor be 80~100g/min, the flow of epoxychloropropane is 23~26g/min, pyridine and catalyst
Mixed liquor, the ring-opening reaction product flow be 21~22g/min.
9. the method for described in any item continuous synthesis of hydroxy propane sulfonic acid pyridinium salt, feature exist according to claim 1~8
In the first reactor and the second reactor are micro passage reaction.
10. the method for continuous synthesis of hydroxy propane sulfonic acid pyridinium salt according to claim 9, it is characterised in that described micro-
Channel reactor is T-type micro passage reaction, and entire reaction process is carried out continuously in the reaction system of microchannel.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811222926.XA CN109265392B (en) | 2018-10-19 | 2018-10-19 | Method for continuously synthesizing pyridinium hydroxy propane sulfonate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201811222926.XA CN109265392B (en) | 2018-10-19 | 2018-10-19 | Method for continuously synthesizing pyridinium hydroxy propane sulfonate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN109265392A true CN109265392A (en) | 2019-01-25 |
| CN109265392B CN109265392B (en) | 2022-02-18 |
Family
ID=65193938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201811222926.XA Active CN109265392B (en) | 2018-10-19 | 2018-10-19 | Method for continuously synthesizing pyridinium hydroxy propane sulfonate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109265392B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349688A (en) * | 2021-12-20 | 2022-04-15 | 常熟聚和化学有限公司 | High-purity pyridinium propanesulfonate solution and preparation method thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1390191A (en) * | 1963-07-19 | 1965-02-26 | Dehydag Gmbh | Process for the preparation of sulfobetaines containing heterocyclic bases of the aromatic type |
| CN102161639A (en) * | 2011-02-21 | 2011-08-24 | 湖北吉和昌化工科技有限公司 | Method for synthesizing pyridinium hydroxy propyl sulfobetaine |
| CN102491942A (en) * | 2011-11-25 | 2012-06-13 | 株洲时代电气绝缘有限责任公司 | Production method of high-purity PPS-OH |
| CN103204802A (en) * | 2012-01-13 | 2013-07-17 | 湖北和昌新材料科技有限公司 | Preparation method of high purity pyridinium hydroxy propyl sulphobetaine |
| CN103922997A (en) * | 2014-04-14 | 2014-07-16 | 湖北吉和昌化工科技有限公司 | Synthetic method of pyridinium hydroxy propyl sulfobetaine |
| CN105198798A (en) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | Production process of pyridinium hydroxy propyl sulfobetaine |
| CN106831544A (en) * | 2017-02-15 | 2017-06-13 | 中卫市创科知识产权投资有限公司 | A kind of PPS OH production technologies |
-
2018
- 2018-10-19 CN CN201811222926.XA patent/CN109265392B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1390191A (en) * | 1963-07-19 | 1965-02-26 | Dehydag Gmbh | Process for the preparation of sulfobetaines containing heterocyclic bases of the aromatic type |
| CN102161639A (en) * | 2011-02-21 | 2011-08-24 | 湖北吉和昌化工科技有限公司 | Method for synthesizing pyridinium hydroxy propyl sulfobetaine |
| CN102491942A (en) * | 2011-11-25 | 2012-06-13 | 株洲时代电气绝缘有限责任公司 | Production method of high-purity PPS-OH |
| CN103204802A (en) * | 2012-01-13 | 2013-07-17 | 湖北和昌新材料科技有限公司 | Preparation method of high purity pyridinium hydroxy propyl sulphobetaine |
| CN103922997A (en) * | 2014-04-14 | 2014-07-16 | 湖北吉和昌化工科技有限公司 | Synthetic method of pyridinium hydroxy propyl sulfobetaine |
| CN105198798A (en) * | 2015-11-03 | 2015-12-30 | 江苏梦得电镀化学品有限公司 | Production process of pyridinium hydroxy propyl sulfobetaine |
| CN106831544A (en) * | 2017-02-15 | 2017-06-13 | 中卫市创科知识产权投资有限公司 | A kind of PPS OH production technologies |
Non-Patent Citations (2)
| Title |
|---|
| 李陵岚，等: "一种高纯度羟基丙烷磺酸吡啶鎓盐的生产方法", 《山东化工》 * |
| 穆金霞，等: "微通道反应器在合成反应中的应用", 《化学进展》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114349688A (en) * | 2021-12-20 | 2022-04-15 | 常熟聚和化学有限公司 | High-purity pyridinium propanesulfonate solution and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN109265392B (en) | 2022-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101607925B (en) | Method for preparing naphthalene sulphonic acid by sulfonating sulfur trioxide in microreactor | |
| CN101717355A (en) | Method for synthesizing dyestuff intermediate H acid by naphthalene | |
| CN112897488B (en) | Method for preparing difluoro sulfimide by micro-channel reactor | |
| CN113999199B (en) | Vinylene carbonate synthesis method | |
| CN109265392A (en) | A kind of method of continuous synthesis of hydroxy propane sulfonic acid pyridinium salt | |
| CN112225642A (en) | Method for preparing resorcinol through microchannel reaction | |
| CN102161639B (en) | Method for synthesizing pyridinium hydroxy propyl sulfobetaine | |
| CN106975360A (en) | A kind of method that many sodium molybdate solutions are prepared based on bipolar membrane electrodialysis | |
| CN110078731A (en) | A kind of method of continuous production tea sodium | |
| CN211734231U (en) | Production system of high-quality fatty alcohol polyoxyethylene ether sulfate | |
| CN110857280B (en) | Preparation method of 2-acrylamide-2-methylpropanesulfonate | |
| CN104250219A (en) | Production method of acrylamido tertiary butyl sulfonic acid | |
| CN109232329A (en) | A kind of synthetic method of Sodium Allyl Sulfonate | |
| CN113897629A (en) | Method for synthesizing anisic aldehyde by flow electrolysis | |
| CN112979579B (en) | Low-temperature diazonium salt continuous preparation method of halogenated thiazole compound | |
| CN112354508B (en) | Continuous synthesis device and process of 2-acrylamido-2-methylpropanesulfonic acid | |
| CN106345387B (en) | A kind of continuous reaction apparatus and method of amino acid surfactant | |
| CN112625034B (en) | Preparation method of vinpocetine | |
| CN107922324B (en) | Beta-naphthol ether sulfonates, process for their preparation and their use as brightness improvers | |
| CN210458383U (en) | Device suitable for inorganic salt electrolysis | |
| CN105820054A (en) | Preparation method of 3-methoxy-2-nitrobenzoate | |
| CN208407002U (en) | A kind of device of continuity method production tetramethyl ammonium carbonate | |
| CN115745850B (en) | Method for continuous flow production of sodium dodecyl diphenyl ether sulfonate | |
| CN112079751B (en) | Preparation method of high-purity methane sulfonic acid | |
| CN215783355U (en) | Device for continuously producing hydroxyl acetonitrile by using liquid-phase hydrocyanic acid |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |