CN103922997B - A kind of synthetic method of pyridinium hydroxy propyl sulfobetaine - Google Patents
A kind of synthetic method of pyridinium hydroxy propyl sulfobetaine Download PDFInfo
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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
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Abstract
A kind of synthetic method of pyridinium hydroxy propyl sulfobetaine, its step comprises: under normal temperature condition, after hydrosulphite or pyrosulfite fully being dissolved in water, adding auxiliary sulphonating agent S-WAT regulation system pH value is between 5.2-5.5, after add catalyzer polyethers F-6; Add complexing agent again, the condition that controls environment also adds epoxy chloropropane, ring-opening reaction occurs and obtains 3-chlorine-2-hydroxyl propane sulfonate; Pyridine is added again in above-mentioned system, after temperature control back flow reaction, add cleaner triethylamine, react 1 hour, afterwards dehydration and decolorization adjust ph is 2-5, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain the aqueous solution of product pyridinium hydroxy propyl sulfobetaine.The inventive method synthesis of hydroxy propane sulfonic acid pyridinium salt, for one kettle way is produced, meet the requirement of current electroplating industry development, its product foreign matter content is low, outward appearance good, low production cost.
Description
Technical field
The invention belongs to nickel plating intermediate hydroxyl propane sulfonic acid pyridinium salt novel preparation method, it is a kind of electroplating additive in high current density region with light, leveling excellent property
Background technology
Pyridinium hydroxy propyl sulfobetaine is a kind of electroplating intermediate, and sterling is white crystal, commonly content between 40%-50%, colourless to weak yellow liquid product at 3-5 of pH value.No. CAS: 3918-73-8, molecular formula: C
8h
11naO
4s, molecular weight: 217.24.
Pyridinium hydroxy propyl sulfobetaine (PPS-OH) has excellent light and leveling effect in electronickelling, especially good high current density region leveling effect spy.Be 20-50g/kAH as the base additive in nickel plating bath, its consumption, consumption 50-500mg/L, the huge market demand.At present, pyridinium hydroxy propyl sulfobetaine (PPS-OH) liquid product only has German La Xige abroad, BASF AG produces, domestic pharmaceutical industry mainly adopts two-step approach to prepare, its production cost is high, wastewater flow rate is large, product is unstable, the production cycle is long, thus causes domestic main or dependence on import high-quality PPS-OH product.
The domestic and international report of the synthesis to PPS-OH is less at present, mainly contain French Patent FR1390191, patent of the same name is the synthesis preparation method that GB1006139, US3280130, DE19620724 and Chinese patent CN102161639A disclose this product, there is isomer in the synthetic method that wherein French Patent is mentioned, end reaction yield is lower, application effect of products is poor, is not suitable for suitability for industrialized production.I house journal CN102161639A is the new synthetic method proposed in conjunction with foreign data, provides important references suggestion to the suitability for industrialized production of this product domestic.
Its synthetic method is also divided into two steps:
The first step: the synthesis of 3-chlorine-2-hydroxyl propanesulfonate
Under normal temperature condition, by Na
2s0
3, Na
2s
2o
5add catalyzer with after water stirring and dissolving, be warming up between 40-80 DEG C, pass into protection of inert gas, slowly drip epoxy chloropropane, after dripping off, between 40-80 DEG C, be incubated 2 hours, after the de-part water of decompression, obtain 3-chlorine-2-hydroxyl propanesulfonate.
Second step: the synthesis of pyridinium hydroxy propyl sulfobetaine
3-chlorine-2-hydroxyl propane sulfonic acid sodium is dissolved in water, add effective catalyst 1 again, 4,7,13-tetra-oxa--10-azepine-2,3-benzo ring 15-2-alkene, between 30-100 DEG C, with pyridine reaction 6-12 hour, part water is sloughed in decompression, eventually passes decolouring removal of impurities and obtains the pyridinium hydroxy propyl sulfobetaine aqueous solution.
Its reaction principle is:
There is following shortcoming in synthesis of hydroxy propane sulfonic acid pyridinium salt according to the method described above;
Analyze through HPLC and find that foreign matter content is higher, plating application shows as coating fragility is comparatively large, obfuscation; Secondly foreign matter content is higher comparatively large on the impact of product colourity, and comparatively external product colourity is dark, in faint yellow to yellow to show as the product of production; The product produced according to the method described above is long placed in and easily occurs metachromatism afterwards, show as to redden/yellow; Pyridine large usage quantity in such scheme and reclaim difficulty, causes raw materials for production to waste serious.
In today that nickel plating industry development becomes more meticulous day by day, said synthesis route has been difficult to produce the high-end product that becomes more meticulous that can meet industry needs.
Summary of the invention
The object of the invention is to improve the deficiencies in the prior art, provides that a kind of foreign matter content meeting current electroplating industry demand for development is low, outward appearance good, the preparation method of the pyridinium hydroxy propyl sulfobetaine of low production cost.
The present invention is achieved through the following technical solutions: a kind of synthetic method of pyridinium hydroxy propyl sulfobetaine, and its step comprises:
(1) synthesis of intermediate 3-chlorine-2-hydroxyl propane sulfonate
Under normal temperature condition, after hydrosulphite or pyrosulfite fully being dissolved in water, adding auxiliary sulphonating agent S-WAT regulation system pH value is between 5.2-5.5, after add catalyzer polyethers F-6; Add complexing agent again, the condition that controls environment also adds epoxy chloropropane, ring-opening reaction occurs and obtains 3-chlorine-2-hydroxyl propane sulfonate.
(2) synthesis of pyridinium hydroxy propyl sulfobetaine
Pyridine is added again in above-mentioned system, after temperature control back flow reaction, add cleaner triethylamine, react 1 hour, afterwards dehydration and decolorization adjust ph is 2-5, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain the aqueous solution of product pyridinium hydroxy propyl sulfobetaine.
Described catalyzer polyethers F-6 consumption is the 0.04-0.07% of system total amount quality.
Described stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount.
Described complexing agent citric acid, its consumption is the 0.003-0.005% of pyrosulfite total mass.
During described epoxy chloropropane generation ring-opening reaction, in the hierarchy of control, temperature is 40-70 DEG C, and passes into nitrogen as protection gas.
During described epoxy chloropropane generation ring-opening reaction, need epoxy chloropropane slowly to instill, and its consumption and Sodium Pyrosulfite mol ratio are 1:0.51-0.52.
Described system directly adds pyridine after being obtained by reacting 3-chlorine-2-hydroxyl propane sulfonate, and the mol ratio of its consumption and epoxy chloropropane is 0.93:1.
After described system adds pyridine, be warming up to back flow reaction 10-14 hour between 95-110 DEG C.
Described cleaner triethylamine, its addition is the 5-7.5% of pyridine total mass.
The preferred technical solution of the present invention is: under normal temperature condition, after sodium bisulfite or Sodium Pyrosulfite are fully dissolved in water, add auxiliary sulphonating agent S-WAT regulation system pH value be between 5.2-5.5 after add catalyzer polyethers F-6 (that is: vinyl carbinol and oxyethane, epoxypropane polymer), its consumption is the 0.04-0.07% of system total amount quality.Add citric acid in this system again as complexing agent, its consumption is the 0.003-0.005% of Sodium Pyrosulfite total amount quality.After this system is warming up to 40-70 DEG C, pass into nitrogen as protection gas, slowly drip epoxy chloropropane under this condition, its consumption and Sodium Pyrosulfite mol ratio are 1:(0.51-0.52).Above-mentionedly be obtained by reacting intermediate product 3-chlorine-2-hydroxyl propane sulfonate.
In above-mentioned system, add appropriate pyridine again, the mol ratio of its consumption and epoxy chloropropane is 0.93:1.Between system intensification 95-110 DEG C, after back flow reaction 10-14 hour, then add cleaner triethylamine, its addition is the 5-7.5% of pyridine consumption, reacts 1 hour.After this system dehydration and decolorization, adjust ph is between 2-5, adds stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount, obtains pyridinium hydroxy propyl sulfobetaine (PPS-OH) aqueous products.
Reaction principle of the present invention is as follows:
Synthesis of hydroxy propane sulfonic acid pyridinium salt (PPS-OH) of the present invention, this process is one kettle way, does not need isolation of intermediate products to get final product subsequent production; And in multiple reaction control condition and use catalyzer, complexing agent, stablizer etc., strictly can control the content of pyridine in product and pyridine derivate.Use low bubble catalyzer polyethers F-6 (that is: vinyl carbinol and oxyethane, epoxypropane polymer), speed of reaction can be accelerated improve transformation efficiency, avoid follow-up decompression dehydration process system foaming abundancy to bring the loss of punching material simultaneously, improve reaction conversion ratio.The formation reaction of intermediate product 3-chlorine-2-hydroxyl propane sulfonic acid sodium, control condition pH value is between 5.2-5.5, suppresses raw material hydrolysis, effectively can reduce the content of pyridine derivate in product.Add after citric acid makes complexing agent in reaction, resultant metal total ion concentration controls at below 10ppm, effectively avoids metal ion and pyridine derivate effect and causes product variable color, improve application effect of products simultaneously.Adding stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives in reaction end can make the colourity of product ensure to remain unchanged for a long period of time look at below 50# (platinum-cobalt method), raising product quality.In reaction process, epoxy chloropropane and pyridine consumption mol ratio are 1:0.93, while the high yield of guarantee, greatly reduce product cost, decrease follow-up pyridine recycling step, meet green chemistry route.Reaction end adds cleaner triethylamine and effectively can go out pyridine and its derivatives in product and improve application effect of products, reduces coating fragility and blackout phenomenon.
Embodiment
By the following specific examples further illustrate the invention:
Example 1
To with in the 500ml tetra-neck flask of mechanical stirring, thermometer, reflux condensing tube, constant pressure funnel, add deionized water (335g, 18.59mol), Sodium Pyrosulfite (97g, 0.51mol), after abundant stirring makes it dissolve, add auxiliary sulphonating agent S-WAT (11.57g, 0.091mol) regulation system pH is 5.5, add 0.2552g catalyzer polyethers F-6 (vinyl carbinol and oxyethane, epoxypropane polymer), citric acid 0.0028g.System passes into nitrogen protection after being warming up to 60-65 DEG C; slow dropping epoxy chloropropane (92.31g, 1.0mol), controlling dropping temperature is between 60-65 DEG C; after dripping between this 60-65 DEG C insulation reaction 4 hours, be warming up to 70-75 DEG C of insulation reaction 1 hour afterwards.Insulation reaction terminates to add pyridine (73.77g, 0.93mol), is warming up to 90-105 DEG C of back flow reaction 10 hours.Add 4g cleaner triethylamine afterwards, with between hydrochloric acid regulation system pH value 2-5 after decompression dehydration decolouring, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives obtain colourity and are less than 50# (platinum-cobalt method) light yellow transparent liquid.
Respond well through plating application testing, high current density region coating Bai Liangwu fragility free of pinholes, analyze its yield through HPLC and reach 90.03%, before contrast, synthetic schemes product impurity is lower, and colourity is less, and room temperature keeps in Dark Place 1 year without color stability.
Example 2
To with in the 2000ml tetra-neck flask of mechanical stirring, thermometer, reflux condensing tube, constant pressure funnel, add deionized water (775g, 43mol), Sodium Pyrosulfite (194.20g, 1.02mol), after abundant stirring makes it dissolve, add auxiliary sulphonating agent S-WAT (20.42g, 0.162mol) regulation system pH value is 5.35, add 0.933g catalyzer polyethers F-6 (that is: vinyl carbinol and oxyethane, epoxypropane polymer), complexing agent citric acid 0.058g.System passes into nitrogen protection after being warming up to 65-70 DEG C, slowly drips epoxy chloropropane (185.07g, 2.0mol).To be added dropwise to complete between rear 65-70 DEG C insulation reaction 3 hours, to be warming up to 75-80 DEG C of insulation reaction 1 hour afterwards.Insulation reaction terminates to add pyridine (147.66g, 1.86mol), and is warming up to back flow reaction between 95-105 DEG C, and backflow end adds 11.07g cleaner triethylamine.With adding 2.66g stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives after hydrochloric acid regulation system pH value to 3.5 after decompression dehydration decolouring, obtain micro-yellow transparent clarification PPS-OH aqueous products.
91.63% is reached through HPLC ultra-violet analysis yield, it was 0.55% (patent CN102161639A synthetic method product impurity accounting is about 1.3-1.5% before) that impurity accounts for main peak ratio, colourity is 25# (platinum-cobalt method), and plating test piece applied analysis is good.
Example 3
1600kg deionized water is added in 3000L standard reaction still, Sodium Pyrosulfite (500Kg is dropped under stirring, S-WAT (38kg is added after 2.63kmol) dissolving, 0.3kmol) adjust ph to 5.35, add catalyzer 2.06kg polyethers F-6 (that is: vinyl carbinol and oxyethane, epoxypropane polymer), complexing agent citric acid 0.15kg.Be warming up to 60-70 DEG C and pass into nitrogen protection, slowly drip epoxy chloropropane (470kg, 5.07kmol), now heat release is obvious.Drip end temperature control 65-70 DEG C of insulation reaction and be warming up to 80-90 DEG C of reaction 1 hour after 4 hours, reaction end adds pyridine (375kg, 4.74kmol).Be warming up to 100-110 DEG C of back flow reaction after 14 hours, add 18.75kg cleaner triethylamine.With after salt acid for adjusting pH value to 3.5 after dehydration and decolorization, add 5.88kg stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, react to filter after 1 hour and obtain colourity and be less than 25# (platinum-cobalt method) micro-yellow transparent clarified liq PPS-OH product.
Be 0.71% through HPLC analysing impurity and main peak content balance, yield is 91.32%, and test piece effect is good.
Example 4
Be used for barrel plating nickel plating bath and additive according to recipe configuration described in following table, the pH value that PPS-OH is used in barrel plating nickel plating is 4.5-5.8, Hull cell current intensity 2-4A/dm
2, bright current density range 2-4A/dm
2, temperature range 50-60 DEG C, coating is bright, excellent without blackout phenomenon, ductility, resistance to abrasion without pit, low current density district in vain.
(wherein PPS-OH: pyridinium hydroxy propyl sulfobetaine, PME: propiolic alcohol oxyethyl group ether, PABS:N, N-PABS, PS: propargyl sodium sulfonate, PA: propargyl alcohol, BEO: butynediol ethoxy compound, POPDH: propiolic alcohol glyceryl ether, PN: sodium hydroxymethane sulfonate, UPS: isothiourea propanesulfonic acid inner salt, EHS: sodium isethionate, BBI: two phenyl ring imide, ALS: sodium allyl sulfonate, ATPN:S-propyloic isothiourea drone.)
Example 5
Be used for rack plating nickel plating bath and additive according to recipe configuration described in following table, the pH value that PPS-OH is used in rack plating nickel plating is 4.5-5.8, Hull cell current intensity 2-4A/dm
2, bright current density range 2-4A/dm
2, temperature range 50-60 DEG C, coating is bright, excellent without blackout phenomenon, ductility, resistance to abrasion without pit, low current density district in vain.
(wherein: PPS-OH: pyridinium hydroxy propyl sulfobetaine, PME: propiolic alcohol oxyethyl group ether, PABS:N, N-PABS, PS: propargyl sodium sulfonate, PA: propargyl alcohol, BEO: butynediol ethoxy compound, POPDH: propiolic alcohol glyceryl ether, EHS: sodium isethionate, BBI: two phenyl ring imide, ALS: sodium allyl sulfonate, ATPN:S-propyloic isothiourea drone.)
The above, be only the specific embodiment of the present invention, it should be pointed out that any those of ordinary skill in the art are in the technical scope disclosed by the present invention, the change that can expect easily or replacement, all should be encompassed within protection scope of the present invention.
Claims (9)
1. a synthetic method for pyridinium hydroxy propyl sulfobetaine, its step comprises:
(1) synthesis of intermediate 3-chlorine-2-hydroxyl propane sulfonate
Under normal temperature condition, after hydrosulphite or pyrosulfite fully being dissolved in water, adding auxiliary sulphonating agent S-WAT regulation system pH value is between 5.2-5.5, after add catalyzer polyethers F-6; Add complexing agent again, the condition that controls environment also adds epoxy chloropropane, ring-opening reaction occurs and obtains 3-chlorine-2-hydroxyl propane sulfonate.
(2) synthesis of pyridinium hydroxy propyl sulfobetaine
Pyridine is added again in above-mentioned system, after temperature control back flow reaction, add cleaner triethylamine, react 1 hour, afterwards dehydration and decolorization adjust ph is 2-5, add stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, obtain the aqueous solution of product pyridinium hydroxy propyl sulfobetaine.
2. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described catalyzer polyethers F-6 consumption is the 0.04-0.07% of system total amount quality.
3. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described stablizer 4-hydroxyl-2,2,6,6-tetramethyl piperidine-1-oxyradical and vitamin C derivatives, its consumption is 0.02% of system total amount.
4. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described complexing agent citric acid, and its consumption is the 0.003-0.005% of pyrosulfite total mass.
5. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: during described epoxy chloropropane generation ring-opening reaction, in the hierarchy of control, temperature is 40-70 DEG C, and passes into nitrogen as protection gas.
6. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, it is characterized in that: during described epoxy chloropropane generation ring-opening reaction, need epoxy chloropropane slowly to instill, and its consumption and Sodium Pyrosulfite mol ratio are 1:0.51-0.52.
7. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described pyridine, and the mol ratio of its consumption and epoxy chloropropane is 0.93:1.
8. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: after described system adds pyridine, is warming up to back flow reaction 10-14 hour between 95-110 DEG C.
9. the synthetic method of pyridinium hydroxy propyl sulfobetaine according to claim 1, is characterized in that: described cleaner triethylamine, and its addition is the 5-7.5% of pyridine total mass.
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| WO2023211589A1 (en) * | 2022-04-25 | 2023-11-02 | Saudi Arabian Oil Company | Corrosion inhibitor formulations based on compounds with both pyridinium and hydroxy substituents |
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| 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 |
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| CN111748830A (en) * | 2020-07-22 | 2020-10-09 | 六安市金安区宝德龙科技创新有限公司 | High-speed barrel nickel plating brightener and preparation method thereof |
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3280130A (en) * | 1962-07-21 | 1966-10-18 | Dehydag Gmbh | Process for the preparation of sulfobetaines of 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 |
-
2014
- 2014-04-14 CN CN201410146820.1A patent/CN103922997B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3280130A (en) * | 1962-07-21 | 1966-10-18 | Dehydag Gmbh | Process for the preparation of sulfobetaines of 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 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2023211589A1 (en) * | 2022-04-25 | 2023-11-02 | Saudi Arabian Oil Company | Corrosion inhibitor formulations based on compounds with both pyridinium and hydroxy substituents |
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