CN-122010786-A - Guanidine alkyl sulfonate and preparation method thereof

Abstract

The invention provides alkyl guanidine sulfonate and a preparation method thereof, which belong to the technical field of organic synthesis, and the preparation method of the alkyl guanidine sulfonate comprises the following steps of reacting sodium alkyl sulfonate solution with guanidine hydrochloride solution to obtain a reaction product; mixing the reaction product with organic solvent to obtain paste-containing product, freezing the product, and post-treating to obtain guanidine alkyl sulfonate. The method has the advantages of low-corrosiveness conventional chemicals as raw materials, reduced equipment requirements, water as a reaction medium, reduced use of organic solvents, more environmental protection and economy, no need of high temperature and high pressure for the reaction, substitution of multiple recrystallization by freeze filtration, simple and efficient process, contribution to improving the yield, high product purity and good stability, and is suitable for being applied to the field of high precision.

Inventors

• XIONG LI
• SHEN JUEFENG
• ZHANG YATING
• LIU JIALI
• SHEN FANGLIANG
• Shi Zhongpu

Assignees

• 蓝德(江苏)新材料科技有限公司

Dates

Publication Date

20260512

Application Date

20260123

Claims (9)

1. 1. The alkyl guanidine sulfonate is characterized by having a structural formula: Or (b) 1 And 2 Wherein R 1 、R 2 、R 3 、R 4 、R 5 is alkyl.
2. 2. The method for preparing guanidine alkyl sulfonate according to claim 1, comprising the steps of: 1) Reacting an alkyl sodium sulfonate solution with a guanidine hydrochloride solution to obtain a reaction product; 2) Mixing the reaction product with organic solvent to obtain paste-containing product, freezing the product, and post-treating to obtain guanidine alkyl sulfonate.
3. 3. The preparation method of the guanidine hydrochloride solution is characterized in that the sodium alkyl sulfonate solution is an aqueous solution of sodium alkyl sulfonate, the mass ratio of sodium alkyl sulfonate to water in the sodium alkyl sulfonate solution is 1:1-2, and the mass ratio of guanidine hydrochloride to water in the guanidine hydrochloride solution is 1:1-1.5.
4. 4. The preparation method according to claim 2 or 3, wherein the molar ratio of the sodium alkyl sulfonate to the guanidine hydrochloride is 1-1.5:1.
5. 5. The method according to claim 4, wherein the purity of sodium alkyl sulfonate is not less than 98% and the purity of guanidine hydrochloride is not less than 98%.
6. 6. The preparation method according to claim 4, wherein the reaction temperature is normal temperature and the reaction time is 3-5 hours.
7. 7. The preparation method according to claim 5 or 6, wherein the organic solvent is dichloromethane and/or xylene, and the mass ratio of the reaction product to the organic solvent is 0.8-1.2:0.8-1.2.
8. 8. The method according to claim 7, wherein the freezing temperature is-20 to-10 ℃ and the freezing time is 1 to 5 hours.
9. 9. The preparation method of the composite material according to claim 8, wherein the post-treatment is carried out by sequentially filtering and drying the frozen product, and the drying temperature is 60-70 ℃.

Description

Guanidine alkyl sulfonate and preparation method thereof Technical Field The invention relates to the technical field of organic synthesis, in particular to alkyl guanidine sulfonate and a preparation method thereof. Background The guanidine salt compound is a functional salt substance with unique structure and performance, and shows important application value in the fields of antibiosis, flame retardance, ion exchange and the like by virtue of strong polarity, biological activity of guanidine groups and ionic characteristics of sulfonate groups. The alkyl sulfonic acid guanidine salt can flexibly adjust the hydrophilicity and hydrophobicity of a compound, the interfacial activity and the compatibility with other materials due to the introduction of an alkyl chain, has the broad-spectrum antibacterial property of guanidine groups, the stability of sulfonate groups and the performance regulation and control function of the alkyl chain, has good application potential in the fields of high-performance antibacterial materials, environment-friendly flame retardant additives, fine chemical separation media and the like, and is widely focused. The properties of guanidine sulfonate vary depending on specific structures, and the main application fields include (1) guanidine groups have strong polarity and positive charge, are easily combined with negative charges (such as phospholipids and proteins) on the surfaces of microbial cell membranes, destroy cell membrane structures and inhibit metabolism, SO that guanidine sulfonate often exhibits broad-spectrum antibacterial activity, (2) sulfonate groups (-SO 3-) have strong hydrophilicity and ion exchange capacity, while guanidine groups (-C (NH 2)2+) are cationic groups, SO that guanidine sulfonate can be used as an ion exchanger or a separation medium, (3) guanidine groups are key active groups (such as antibacterial agents and antihypertensive agents) of many drug molecules, and sulfonate groups can regulate the water solubility and stability of compounds, SO that guanidine sulfonate is commonly used as an intermediate of medicines, (4) guanidine sulfonate can be used as an additive of electroplating solutions, and uniformity and adhesiveness of plating layers can be improved by adjusting ion concentration and interfacial tension. The existing alkyl guanidine sulfonate has the disadvantages that the synthesis method is difficult, the yield is low, such as hexyl guanidine sulfate, ethanol is used as a solvent, the reaction is carried out at a certain temperature, and the filtration and recrystallization are carried out, so that the yield is below 70%. Another method is to remove water and obtain the product by reacting guanidine carbonate solution with acid. The acid used in the method is strong acid such as methanesulfonic acid, sulfuric acid, nitric acid, trifluoromethanesulfonic acid and the like, and water is removed in a high-temperature and vacuum environment after the reaction is completed. Both of the above methods are not suitable for industrial production. The existing preparation method of the guanidine alkyl sulfonate has the main problems that the synthesis efficiency is low and limited by the complexity of a guanidine alkylation process, the product yield is generally lower than 70%, the efficiency requirement of industrial production is difficult to meet, the purification process is complex, the purification is realized by multiple filtration and recrystallization, the production period is prolonged, the total yield is further reduced due to crystallization loss, the compatibility of raw materials and the process is poor, equipment is easy to corrode when strong acid (such as methanesulfonic acid, sulfuric acid and the like) is adopted to participate in the reaction, and the follow-up high-temperature vacuum condition is needed to remove water, so that the energy consumption and the operation risk are increased, and the industrialization adaptability is insufficient, complicated process steps, harsh reaction conditions and lower yield are caused, so that the existing method is difficult to realize large-scale production, and the wide application of the guanidine alkyl sulfonate in various fields is limited. Therefore, the alkyl guanidine sulfonate with simple process, low corrosiveness and improved product yield and purity and the preparation method thereof have important significance. Disclosure of Invention The invention aims to provide alkyl guanidine sulfonate and a preparation method thereof, which solve the problems of high energy consumption and strong acid adopted as raw materials in the prior art. In order to achieve the above object, the present invention provides the following technical solutions: the invention provides alkyl guanidine sulfonate, which has the structural formula: Or (b) 1 And 2 Wherein R 1、R2、R3、R4、R5 is alkyl. The invention also provides a preparation method of the guanidine alkyl sulfonate, which comprises the following s