CN112209858B - Preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid - Google Patents
Preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid Download PDFInfo
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- CN112209858B CN112209858B CN202011108629.XA CN202011108629A CN112209858B CN 112209858 B CN112209858 B CN 112209858B CN 202011108629 A CN202011108629 A CN 202011108629A CN 112209858 B CN112209858 B CN 112209858B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/42—Separation; Purification; Stabilisation; Use of additives
- C07C303/44—Separation; Purification
Abstract
The invention provides a preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, which comprises the following steps: putting 20g of tris (hydroxymethyl) aminomethane, 100g of methanol, 1g of copper powder, 1g of potassium iodide and 300g of dichloroethane into a three-necked flask, and heating to reflux; dissolving 9g of sodium methoxide in 50g of methanol to obtain a sodium methoxide methanol solution, and slowly dropwise adding the sodium methoxide methanol solution into a three-necked bottle for reflux reaction for 6 hours; adding 200g of water into the three-necked bottle, heating to recover the solvent, and heating to 95 ℃ after the solvent is completely removed; adding 23.5g of sodium bisulfite and 100g of water into a three-necked bottle, carrying out heat preservation reaction for 5 hours, filtering to obtain a first filtrate, and adding the first filtrate into the three-necked bottle; adding 100g of ion exchange resin into a three-necked bottle, heating to reflux, stirring for 1 hour, cooling to room temperature, filtering to obtain a filter cake and a second filtrate, and decolorizing and filtering the second filtrate to obtain a third filtrate; heating and evaporating the third filtrate to be pulpous, adding ethanol, cooling and rapidly stirring to obtain white crystal-shaped 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid. The preparation method provided by the invention is simple in process.
Description
Technical Field
The invention relates to the technical field of biological pharmacy, in particular to a preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid.
Background
TES, the Chinese name 2- [ [ Tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, also known as Tris ethanesulfonic acid, has a structure similar to Trizma and meets various standards of "Good" buffers, and the structure is neutral molecules but still shows zwitterions in solution. TES is suitable for a variety of cell culture systems that require divalent metal ions, and many other buffers (such as citrate or phosphate) can produce chelation or precipitation reactions that do not meet this requirement. In addition, TES is extremely useful for the study of succinic acid oxidation reactions.
In the related technology, the preparation of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid is usually to prepare sodium chloroethanesulfonate first, and then to react with sodium chloroethanesulfonate to generate 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid.
Therefore, there is a need to provide a novel method for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid to solve the above problems.
Disclosure of Invention
The invention aims to overcome the technical problems and provide a preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, which has simple preparation process and short preparation time.
In order to achieve the above object, the present invention provides a method for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, comprising the steps of:
s1: putting 20g of tris (hydroxymethyl) aminomethane, 100g of methanol, 1g of copper powder, 1g of potassium iodide and 300g of dichloroethane into a three-necked bottle, and heating until reflux;
s2: dissolving 9g of sodium methoxide in 50g of methanol to obtain a sodium methoxide methanol solution, then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle, and carrying out reflux reaction for 6 hours after dropwise adding the sodium methoxide methanol solution;
s3: adding 200g of water into the three-mouth bottle, continuously heating to recover dichloroethane and methanol, and heating to 95 ℃ after recovery;
s4: adding 23.5g of sodium bisulfite and 100g of water into the three-mouth bottle, carrying out heat preservation reaction for 5 hours, filtering to obtain a first filtrate, and adding the first filtrate into the three-mouth bottle;
s5: adding 100g of ion exchange resin into the three-mouth bottle, heating to reflux, stirring for 1 hour, cooling to room temperature, filtering to obtain a filter cake and a second filtrate, decoloring the second filtrate, and filtering again to obtain a third filtrate;
s6: heating the third filtrate to evaporate water to be in a slurry state, adding ethanol, cooling and rapidly stirring to obtain white crystal-shaped 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid.
Preferably, the three-mouth bottle is a 1000ml three-mouth bottle.
Preferably, the step S2 of "slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle" includes the following steps:
s21: adding the sodium methoxide methanol solution into a dropping funnel, and then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle;
s22: and monitoring the pH value of the solution in the three-mouth bottle when the solution is dripped, stopping dripping when the pH value is more than 10, and continuing dripping after the pH value falls back.
Preferably, the dichloroethane and methanol recovered in step S3 can be recycled.
Preferably, the ion exchange resin in step S5 is a strong acid adsorption type ion exchange resin.
Preferably, the "filter cake" in step S5 is an ion exchange resin, and the filter cake can be reused after being acidified and regenerated.
Preferably, the "decoloring the second filtrate" in the step S5 specifically includes: and 2g of activated carbon is added into the second filtrate for adsorption and decoloration.
Compared with the prior art, the preparation method of the 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid provided by the invention adopts a one-pot method to prepare the 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, so that the process of preparing and purifying sodium chloroacetate is omitted, the total preparation time is shorter, and meanwhile, strong acid type ion exchange resin is adopted during acidification, so that sodium ions can be removed more simply, conveniently and effectively, the method is simple, convenient and effective, and the method can be used for industrial production.
Detailed Description
The technical solutions in the embodiments of the present invention will be described clearly and completely below, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention provides a preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, which comprises the following steps:
s1: 20g of tris (hydroxymethyl) aminomethane, 100g of methanol, 1g of copper powder, 1g of potassium iodide, and 300g of dichloroethane were put into a three-necked flask and heated to reflux.
In this embodiment, the three-necked bottle is a 1000ml three-necked bottle, and a stirring rod may be provided in the middle opening of the three-necked bottle to facilitate the stirring process in the subsequent step.
The raw materials are directly and completely added into the three-mouth bottle in a one-pot method, so that the process of preparing and purifying sodium chloroethanesulfonate in the related technology is omitted, and the process is simple.
S2: dissolving 9g of sodium methoxide in 50g of methanol to obtain a sodium methoxide methanol solution, then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle, and carrying out reflux reaction for 6 hours after dropwise adding the sodium methoxide methanol solution.
The step S2 of "slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle" includes the following steps:
s21: adding the sodium methoxide methanol solution into a dropping funnel, and then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle;
s22: and monitoring the pH value of the solution in the three-mouth bottle when the solution is dripped, stopping dripping when the pH value is more than 10, and continuing dripping after the pH value falls back.
Adopt dropping funnel to carry out the dropping liquid, can effectual control the addition of sodium methoxide methanol solution avoids local concentration too big.
S3: 200g of water is added into the three-mouth bottle, heating is continued to recover dichloroethane and methanol, and the temperature is raised to 95 ℃ after recovery.
The recycled dichloroethane and methanol can be repeatedly utilized, the waste of materials is avoided, and the production cost is reduced.
S4: adding 23.5g of sodium bisulfite and 100g of water into the three-mouth bottle, carrying out heat preservation reaction for 5 hours, filtering to obtain a first filtrate, and adding the first filtrate into the three-mouth bottle;
s5: adding 100g of ion exchange resin into the three-mouth bottle, heating to reflux, stirring for 1 hour, cooling to room temperature, filtering to obtain a filter cake and a second filtrate, decoloring the second filtrate, and filtering again to obtain a third filtrate.
The ion exchange resin in the step S5 is strong acid adsorption type ion exchange resin; the 'filter cake' in the step S5 is ion exchange resin, and the filter cake can be repeatedly used after being acidified and regenerated. The step S5 of "decoloring the second filtrate" specifically includes: and 2g of activated carbon is added into the second filtrate for adsorption and decoloration.
S6: and heating the third filtrate to evaporate water to be in a paste state, adding ethanol, cooling and rapidly stirring to obtain white crystal-shaped 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid.
30g of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid can be prepared according to the above-mentioned proportion, the calculated yield is 81%, and the prepared 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid nuclear magnetic data are consistent with those in relevant documents.
Compared with the prior art, the preparation method of the 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid provided by the invention adopts a one-pot method to prepare the 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid, so that the process of preparing and purifying sodium chloroacetate is omitted, the total preparation time is shorter, and meanwhile, strong acid type ion exchange resin is adopted during acidification, so that sodium ions can be removed more simply, conveniently and effectively, the method is simple, convenient and effective, and the method can be used for industrial production.
While the foregoing is directed to embodiments of the present invention, it will be understood by those skilled in the art that various changes may be made without departing from the spirit and scope of the invention.
Claims (7)
1. A preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid is characterized by comprising the following steps:
s1: putting 20g of tris (hydroxymethyl) aminomethane, 100g of methanol, 1g of copper powder, 1g of potassium iodide and 300g of dichloroethane into a three-necked bottle, and heating until reflux;
s2: dissolving 9g of sodium methoxide in 50g of methanol to obtain a sodium methoxide methanol solution, then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle, and carrying out reflux reaction for 6 hours after the dropwise adding of the sodium methoxide methanol solution is finished;
s3: adding 200g of water into the three-mouth bottle, continuously heating to recover dichloroethane and methanol, and heating to 95 ℃ after recovery;
s4: adding 23.5g of sodium bisulfite and 100g of water into the three-mouth bottle, carrying out heat preservation reaction for 5 hours, filtering to obtain a first filtrate, and adding the first filtrate into the three-mouth bottle;
s5: adding 100g of ion exchange resin into the three-mouth bottle, heating to reflux, stirring for 1 hour, cooling to room temperature, filtering to obtain a filter cake and a second filtrate, decoloring the second filtrate, and filtering again to obtain a third filtrate;
s6: and heating the third filtrate to evaporate water to be in a paste state, adding ethanol, cooling and rapidly stirring to obtain white crystal-shaped 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid.
2. The process for the preparation of 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 1, characterized in that the three-necked bottle is a 1000ml three-necked bottle.
3. The method for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 1, wherein the step S2 of "slowly dropping the sodium methoxide methanol solution into the three-necked bottle" comprises the steps of:
s21: adding the sodium methoxide methanol solution into a dropping funnel, and then slowly dropwise adding the sodium methoxide methanol solution into the three-necked bottle;
s22: and monitoring the pH value of the solution in the three-mouth bottle during dripping, stopping dripping when the pH value is more than 10, and continuing to drip after the pH value falls back.
4. The process for the preparation of 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 1, wherein dichloroethane and methanol recovered in step S3 can be recycled.
5. The process for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 1, wherein the ion exchange resin in step S5 is a strong acid adsorption type ion exchange resin.
6. The process for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 5, wherein the "filter cake" in step S5 is an ion exchange resin, and the filter cake is regenerated by acidification and can be reused.
7. The process for preparing 2- [ [ tris (hydroxymethyl) methyl ] amino ] ethanesulfonic acid according to claim 1, wherein the "decolorizing the second filtrate" in step S5 is specifically: and 2g of activated carbon is added into the second filtrate for adsorption and decoloration.
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| CN202011108629.XA CN112209858B (en) | 2020-10-16 | 2020-10-16 | Preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid |
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| CN202011108629.XA CN112209858B (en) | 2020-10-16 | 2020-10-16 | Preparation method of 2- [ [ tri (hydroxymethyl) methyl ] amino ] ethanesulfonic acid |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2472562A1 (en) * | 1979-07-30 | 1981-07-03 | Nippon Paint Co Ltd | PROCESS FOR PREPARING HYDROXYALKYLAMINOSULFONIC ACIDS |
| CN104829470A (en) * | 2015-04-20 | 2015-08-12 | 江苏宇田生物医药科技有限公司 | Set of intermediate compounds used for synthesis of Ivabradine, and applications thereof |
| CN111116441A (en) * | 2020-01-07 | 2020-05-08 | 浙江工业大学 | Synthesis method and application of sulfo-containing sulfur ylide |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH04149168A (en) * | 1990-10-12 | 1992-05-22 | Mitsui Toatsu Chem Inc | Production of aminoalkylsulfonic acid compounds |
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- 2020-10-16 CN CN202011108629.XA patent/CN112209858B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2472562A1 (en) * | 1979-07-30 | 1981-07-03 | Nippon Paint Co Ltd | PROCESS FOR PREPARING HYDROXYALKYLAMINOSULFONIC ACIDS |
| CN104829470A (en) * | 2015-04-20 | 2015-08-12 | 江苏宇田生物医药科技有限公司 | Set of intermediate compounds used for synthesis of Ivabradine, and applications thereof |
| CN111116441A (en) * | 2020-01-07 | 2020-05-08 | 浙江工业大学 | Synthesis method and application of sulfo-containing sulfur ylide |
Non-Patent Citations (1)
| Title |
|---|
| "Hydrogen Ion Buffers for Biological Research";Norman E. Good et al. et al.;《BIOCHEMISTRY》;19660228;第5卷(第2期);第467-477页 * |
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