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Method for synthesizing pyridinium hydroxy propyl sulfobetaine

A kind of hydroxypropanesulfonic acid pyridinium salt, the technology of synthesis method, applied in the field of synthesis of nickel plating brightener, can solve the problems such as difficult pH value and temperature control in the specified range, reaction conversion rate reduction, many by-products, etc., Achieve good catalytic reaction effect, reduce free radical polymerization, and fast reaction speed

Inactive Publication Date: 2011-08-24
湖北吉和昌化工科技有限公司
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  • Summary
  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

[0010] But there is following shortcoming in synthesizing PPS-OH according to the above-mentioned method: 1. conversion rate is not high, and final conversion rate is the highest and does not surpass 70%, and there are many by-products, there are two kinds of isomers to exist in the first step reaction product, cause The product quality is not high; 2. It is difficult to realize industrialization, the test operation is cumbersome, the reaction conditions are harsh, it is difficult to control the pH value and temperature within the specified range, otherwise, the reaction conversion rate will be reduced, the heat will be violently released during the reaction process, and it is very easy to bump. , this method can only stay in the laboratory research stage and is not suitable for industrial production; 3. The effect of electroplating application is not ideal. After the application of Hull cell electroplating, due to the existence of intermediate products of the reaction product of pyridine and epichlorohydrin and free pyridine , not only produces a lot of pinholes in the coating, but also the coating is extremely brittle, and the low current density area turns black

Method used

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  • Method for synthesizing pyridinium hydroxy propyl sulfobetaine
  • Method for synthesizing pyridinium hydroxy propyl sulfobetaine
  • Method for synthesizing pyridinium hydroxy propyl sulfobetaine

Examples

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example 1

[0039] Add water (400g, 22.22mol), Na 2 S 2 o 5 (148g, 0.78mol), stirred to make it fully dissolved, then added 5.0gNa 2 SO 3. Pass in inert gas Ar, add 0.14g of phase transfer catalyst tetrabutylammonium bromide, raise the temperature to 40°C, slowly add epichlorohydrin (139g, 1.5mol) dropwise, and keep the reaction at 40°C for 2h after dropping, Then raise the temperature to 75° C. for 1 hour, and dehydrate under reduced pressure for 1 hour to obtain an aqueous solution of sodium 3-chloro-2-hydroxypropanesulfonate.

[0040] Pyridine (121g, 1.53mol) was directly added to the above solution, and 1.2g of high-efficiency catalyst 1,4,7,13-tetraoxa-10-aza-2,3-benzocyclopenta-2-ene was added, Raise the temperature to 30°C for 12 hours, dehydrate under reduced pressure for 3 hours, and decolorize to obtain PPS-OH liquid product 1 with a yield of 90.3%.

example 2

[0042] Add water (400g, 22.22mol), Na 2 S 2 o 5 (148g, 0.78mol), stirred to make it fully dissolved, then added 3gNa 2 SO 3 , add 0.14g of phase transfer catalyst triethylbenzyl ammonium chloride, heat up to 50°C, slowly add epichlorohydrin (139g, 1.5mol) dropwise, after dripping, keep warm at 50°C for 2h, then heat up to Insulate at 70°C for 1 h, dehydrate under reduced pressure for 1 h to obtain an aqueous solution of sodium 3-chloro-2-hydroxypropanesulfonate.

[0043] Pyridine (121g, 1.53mol) was directly added to the above solution, and then 1.2g of high-efficiency catalyst 1,4,7,13-tetraoxa-10-aza-2,3-benzocyclopenta-2-ene was added , heated to 40° C. for 11 h, dehydrated under reduced pressure for 3 h, and decolorized to obtain PPS-OH liquid product 2 with a yield of 91.6%.

example 3

[0045] Add water (400g, 22.22mol), Na 2 S 2 o 5 (148g, 0.78mol), stirred to make it fully dissolved, then added 5.0gNa 2 SO 3 . Pass inert gas N 2 , add phase transfer catalyst NP-21 (0.14g), raise the temperature to 55°C, slowly add epichlorohydrin (139g, 1.5mol) dropwise, keep the reaction at 55°C for 2h after dropping, then raise the temperature to 70°C and keep the temperature 1h, dehydration under reduced pressure for 1h to obtain 3-chloro-2-hydroxypropanesulfonate sodium aqueous solution.

[0046] Pyridine (121g, 1.53mol) was directly added to the above solution, and 1.2g of high-efficiency catalyst 1,4,7,13-tetraoxa-10-aza-2,3-benzocyclopenta-2-ene was added, Raise the temperature to 70° C. for 10 h, dehydrate under reduced pressure for 3 h, and decolorize to obtain PPS-OH liquid product 3 with a yield of 89.7%.

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Abstract

The invention discloses a method for synthesizing pyridinium hydroxy propyl sulfobetaine. The method comprises the following steps of: dissolving pyrosulfite or bisulfite of alkali metal into water, and performing a ring-opening addition reaction of the obtained solution and epichlorohydrin to obtain a ring-opening product with the following chemical formula in the presence of sulfite and a phase transfer catalyst, wherein M is alkali metal in the formula; and dissolving the ring-opening product into water, reacting the obtained solution and pyridine, and purifying to obtain the pyridinium hydroxy propyl sulfobetaine (PPS-OH) after the reaction is finished. By the method for synthesizing the PPS-OH, the yield is high, byproducts are avoided, a product does not contain free pyridine, and the electroplating effect is better. Meanwhile, the method is pollution-free, and is more favorable for environmental protection because water is taken as a solvent. Moreover, the catalyst is added, so that catalytic reaction effect is better, reaction speed is higher, conditions are easier to control, and the method is applicable to industrialized production. The aeration of inert gas into the reaction can also reduce the polymerization of free radicals of the epichlorohydrin caused by the existence of oxygen, so that the yield is further improved.

Description

technical field [0001] The invention belongs to a method for synthesizing a brightener for nickel plating, in particular to a method for synthesizing hydroxypropanesulfonic acid pyridinium salt. Background technique [0002] Hydroxypropanesulfonic acid pyridinium salt is an electroplating intermediate, white crystal, molecular formula: C 8 h 11 NO 4 S, molecular weight: 217.24, CAS number: 3918-73-8. A liquid product with a content between 40-50% is common. Pyridinium hydroxypropane sulfonate (PPS-OH) is one of the main products of nickel plating intermediates. It has excellent brightening and leveling effects, especially in high current density areas, and can produce white and bright effects on the coating. As a basic additive in nickel plating solution, the market consumption is large. At present, the liquid products of pyridinium hydroxypropanesulfonate (PPS-OH) are only produced by Rashing Company in Germany abroad, and domestic counterparts mainly rely on imports. ...

Claims

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Application Information

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IPC IPC(8): C07D213/20C25D3/18
Inventor 黄开伟付远波陈彰评周世骏宋文超
Owner 湖北吉和昌化工科技有限公司
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