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Preparation process of compound containing sulfonic group

A technology containing a sulfonic acid group and a preparation process, applied in the direction of organic chemistry and the like, can solve the problems of large-scale application of compounds hindering the sulfonic acid group, difficulty in obtaining raw materials, and high manufacturing costs, and achieve high product yield, low water content, The effect of increasing productivity

Pending Publication Date: 2022-06-07
SUZHOU YACOO SCI CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] But in general, the number of patents involving sodium salt products among compounds containing sulfonic acid groups is relatively small. Among the existing patents, there are still many problems in the preparation process: the raw materials of the product are not easy to obtain, the manufacturing cost is high, and there are many wastes. Wait
Therefore hinder the large-scale application of the compound of sulfonic acid group, especially hinder it from becoming the material in the field of biological buffer reagent

Method used

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  • Preparation process of compound containing sulfonic group
  • Preparation process of compound containing sulfonic group
  • Preparation process of compound containing sulfonic group

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1: Preparation of piperazine-N,N'-bis(2-ethanesulfonic acid) disodium (PIPES-2Na)

[0052]

[0053] The preparation of piperazine-N,N'-bis(2-ethanesulfonic acid) disodium comprises the following preparation steps:

[0054] Preparation step S1:

[0055] Under stirring conditions, 100 g of compound 1, compound 2, and reaction solvent acetonitrile were added to a 1L dry reactor, wherein compound 1 was piperazine, and compound 2 was ethyl vinyl sulfonate; the moles of compound 1 and compound 2 were The ratio is 1:4, the reaction temperature is 70°C, the reaction pressure is 0.1MPa (gauge pressure), and the reaction time is 4h.

[0056] After the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and concentrated to obtain a crude product of compound 3.

[0057] Preparation step S2:

[0058] Under stirring conditions, the above 100g compound ...

Embodiment 2

[0063] Example 2: Preparation of piperazine-N,N'-bis(2-ethanesulfonic acid) (PIPES)

[0064]

[0065] The preparation of 3-morpholine propanesulfonic acid comprises the following preparation steps:

[0066] Preparation step S1:

[0067] Under stirring conditions, add 100 g of compound 1, compound 2, and reaction solvent acetone into a 1L dry reactor; wherein, compound 1 is piperazine, and compound 2 is propyl vinylsulfonate; the moles of compound 1 and compound 2 are The ratio was 1:10, the reaction temperature was 40°C, the reaction pressure was 0.2MPa (gauge pressure), and the reaction time was 15h.

[0068] After the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and concentrated to obtain a crude product of compound 3.

[0069] Preparation step S2:

[0070] Under stirring conditions, the above-mentioned 100g of compound 3 was added to a 1L dry ...

Embodiment 3

[0077] Example 3: Preparation of sodium 3-morpholine propanesulfonate (MOPS-Na)

[0078]

[0079] The preparation technology of 3-morpholine propanesulfonate sodium comprises the following preparation steps:

[0080] Preparation step S1:

[0081] Under stirring conditions, add 100 g of compound 1, compound 2, and reaction solvent N,N-dimethylformamide into a 1L dry reactor; wherein, compound 1 is morpholine, and compound 2 is methyl allylsulfonate Ester; the molar ratio of compound 2 and compound 3 is 1:1.5, the reaction temperature is 100° C., the reaction pressure is 0.4 MPa (gauge pressure), and the reaction time is 1 h.

[0082] After the completion of the reaction, the temperature was lowered to room temperature, the solvent was removed by rotary evaporation of the reaction solution under reduced pressure, and concentrated to obtain a crude product of compound 3.

[0083] Preparation step S2:

[0084] Under stirring conditions, the above 100g compound 3 was added to...

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Abstract

The invention relates to the technical field of biological buffer reagent synthesis, and discloses a preparation process of a sulfonic group-containing compound and a salt thereof, and the preparation process comprises the following preparation steps: reacting a compound 1 with a compound 2 to obtain a compound 3; reacting the compound 3 with an M-containing reagent to obtain an M-salt-containing crude product corresponding to the sulfonic group-containing compound 4; and carrying out acidification reaction to obtain a crude product of a compound 4 containing sulfonic groups. And finally, carrying out a purification process on the crude products of the sulfonic group-containing compound 4 and the salt thereof to obtain the high-purity sulfonic group-containing compound 4 and the salt thereof. The raw materials used in the preparation method are low in cost and simple to operate, the obtained product is high in purity, the yield of the product is increased, the application cost of the product is reduced, the preparation method is suitable for industrial production, and the obtained product can meet the requirements of the biological buffer on the purity, the impurity content and the cost of the biological buffer.

Description

technical field [0001] The invention belongs to the technical field of biological buffer reagent synthesis, and in particular relates to a preparation process of a sulfonic acid group-containing compound. Background technique [0002] Compounds containing sulfonic acid groups, such as PIPES, MOPS, HEPES, MES and the corresponding sodium salts PIPES-2Na, MOPS-Na, HEPES-Na, MES-Na, are important hydrogen ion buffers within a certain pH range It has good buffering capacity and can maintain a constant pH for a long time. Generally, the sulfonic acid group-containing compound in the culture medium at a concentration of 20 mmol / L can have a good buffering capacity, and the sulfonic acid group-containing compound has no toxic effect on cells. [0003] Chinese patent CN110683995A discloses the preparation methods of two kinds of piperazine ethanesulfonic acid derivatives. Both are in the early stage of feeding, by preheating to initiate the reaction, and by heating the reaction to ...

Claims

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Application Information

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IPC IPC(8): C07D295/088
CPCC07D295/088
Inventor 袁永坤蒋玉贵顾临
Owner SUZHOU YACOO SCI CO LTD
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