CN115322122A - Method for preparing creatine monohydrate from creatine chelated calcium aqueous solution - Google Patents
Method for preparing creatine monohydrate from creatine chelated calcium aqueous solution Download PDFInfo
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- CN115322122A CN115322122A CN202211113927.7A CN202211113927A CN115322122A CN 115322122 A CN115322122 A CN 115322122A CN 202211113927 A CN202211113927 A CN 202211113927A CN 115322122 A CN115322122 A CN 115322122A
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- aqueous solution
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- sarcosinate
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing creatine monohydrate from a creatine calcium chelate aqueous solution. The method comprises the following steps: s1: dropwise adding sulfuric acid with the same amount as the sarcosine chelated calcium into the aqueous solution; s2: filtering after the reaction in the previous step is finished, draining the filter cake, washing the filter cake, and combining washing liquid with filtrate; s3: adjusting the pH value of the combined solution to 10 to 11, and then evaporating, dehydrating and filtering impurities to obtain a filtrate; s4: heating the filtrate obtained in the last step to 60-70 ℃, dropwise adding cyanamide, and reacting for 1-8h under the condition of heat preservation after dropwise adding; s5: and after the reaction in the previous step is finished, cooling to 20 to 30 ℃, adjusting the pH value to 7.5 to 8, stirring for reaction, filtering to obtain a wet creatine product, cleaning a filter cake, draining, and drying to obtain creatine monohydrate. The method has the advantages of simple operation, stable process, easy control of process parameters and no generation of waste gas and harmful gas. The obtained creatine has high purity, and the conversion rate and the yield are higher than those of other synthetic methods. The preparation method is environment-friendly and economical in all the existing synthesis processes.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a method for preparing creatine monohydrate from a creatine calcium chelate aqueous solution.
Background
Creatine is also known as N-methyl guanidinoacetic acid, and the English name is: creatine is white crystal or crystalline powder in appearance, odorless, slightly soluble in water, and high in solubility in hot water. 1.3 g of creatine monohydrate can be dissolved in 100 g of water at the temperature of 20 ℃, and 12 g of creatine monohydrate can be dissolved in 100 g of water at the temperature of about 100 ℃.
Creatine belongs to amino acid derivatives and is an endogenous amino acid. It is naturally present in vertebrates, mainly in skeletal muscle. Can assist in providing energy to muscle and nerve cells.
Regarding the synthetic route of creatine, the following methods are summarized in the prior art:
1. hydroxy acetonitrile and monomethylamine are condensed and hydrolyzed to obtain liquid sodium (potassium) sarcosine aqueous solution, and then the liquid sodium (potassium) sarcosine aqueous solution and the monomethylamine are reacted to obtain creatine monohydrate.
2. The creatine is prepared by reacting sodium sarcosinate with o-methylisourea hydrochloride (sulfate), the method has low conversion rate and low yield, and the qualified creatine can be obtained only by refining the impurities of the product more than twice. And the preparation of o-methylisourea sulfate requires the use of highly toxic dimethyl sulfate.
3. The creatine is prepared by reacting sodium sarcosinate with S-methyl isourea sulfate, and the process has the advantages of low conversion rate, low yield and more impurities, and generates highly toxic byproduct gas of methionine; the preparation of S-methylisourea also requires the use of highly toxic dimethyl sulfate.
The method has obvious defects of low yield, poor quality, generation of extremely toxic substances (or use of extremely toxic raw materials) and great hidden danger for environmental protection and safety.
Disclosure of Invention
Aiming at the defects and shortcomings, the invention provides a new technical scheme: a method for preparing creatine monohydrate from an aqueous solution of calcium sarcosinate comprises the following steps:
s1: dropwise adding sulfuric acid with the same amount as the sarcosine chelated calcium into the aqueous solution;
s2: filtering after the reaction in the previous step is finished, draining the filter cake, washing the filter cake, and combining washing liquid with filtrate;
s3: adjusting the pH value of the combined solution to 10-11, and then evaporating, dehydrating and filtering impurities to obtain a filtrate;
s4: heating the filtrate obtained in the last step to 60-70 ℃, dropwise adding cyanamide, and reacting for 1-8 h after dropwise adding;
s5: after the reaction in the previous step is finished, the temperature is reduced to 20-30 ℃, the PH value is adjusted to 7.5-8, wet creatine is obtained by filtering after stirring reaction, and the creatine monohydrate is obtained by cleaning a filter cake, pumping out and drying.
Further, in step S1, the sarcosine chelated calcium aqueous solution is placed in a reaction vessel with a stirring function, 45% -55% of sulfuric acid is dripped while stirring, and the stirring reaction is continuously carried out for 0.5-5 hours after dripping.
Further, in step S3, the pH is adjusted to 10 with sodium hydroxide.
Further, in step S3, evaporation and dehydration are carried out until the liquid weight is 3-4 times of that of the sarcosine chelated calcium.
Further, the amount of the material of the cyanamide added dropwise in the step S4 is 1.8 to 2.5 times of that of the calcium sarcosinate chelate, and the concentration is 30%.
Further, the pH is adjusted to 7.5 to 8 with 30% hydrochloric acid in step S5.
Further, the cake is washed with 1-fold amount of purified water in step S5.
The invention has the beneficial effects that: the method has the advantages of simple operation, stable process, easily controlled process parameters and no generation of waste gas and harmful gas. The obtained creatine has high purity, and the conversion rate and the yield are higher than those of other synthetic methods. The preparation method is environment-friendly and economical in all the existing synthesis processes.
Detailed Description
A method for preparing creatine monohydrate from an aqueous solution of calcium sarcosinate chelate comprises the following chemical reaction equation:
1.(CH 3 NHCH 2 COO) 2 Ca+H 2 SO 4 →2CH 3 NHCH 2 COOH+CaSO 4 ↓
2.2CH 3 NHCH 2 COOH+NH 2 CN 
feeding molar ratio:
(CH 3 NHCH 2 COO) 2 Ca:H 2 SO 4 ：NH 2 CN＝1:1:2
the method comprises the following operation steps:
accurately weighing 1mol of sarcosine chelated calcium aqueous solution, placing the solution in a clean reaction vessel, starting stirring, dripping 1mol of 50% sulfuric acid at 30 ℃, and stirring for reaction for 30 minutes to 1 hour after dripping;
filtering, separating calcium sulfate precipitate, washing the filter cake precipitate with purified water, and combining the washing liquid and the filtrate.
Adjusting the pH value of the filtrate to 10 by using sodium hydroxide, then evaporating and dehydrating the filtrate until the weight of the filtrate is 700 g, and filtering impurities to obtain filtrate;
and (2) heating the filtrate to 65 ℃, dropwise adding 2mol of 30% cyanamide, keeping the temperature for 1 hour after finishing dripping for about 6-8 hours, cooling to 25 ℃, adjusting the pH value to 7.5-8 by using 30% hydrochloric acid, stirring for 30 minutes, filtering to obtain a wet creatine product, washing by using 1 time of purified water of the filter cake, pumping to dry to obtain about 200 g of wet creatine product, and drying to obtain 185 g of creatine monohydrate.
Claims (7)
1. A method for preparing creatine monohydrate by using an aqueous solution of calcium sarcosinate chelate, which is characterized by comprising the following steps:
s1: dropwise adding sulfuric acid with the same amount as the sarcosine chelated calcium into the aqueous solution;
s2: filtering after the reaction in the previous step is finished, draining the filter cake, washing the filter cake, and combining the washing liquid with the filtrate;
s3: adjusting the pH value of the combined solution to 10 to 11, and then evaporating, dehydrating and filtering impurities to obtain a filtrate;
s4: heating the filtrate obtained in the last step to 60 to 70 ℃, dropwise adding cyanamide, and reacting for 1 to 8h under the condition of heat preservation after dropwise adding;
s5: and after the reaction in the previous step is finished, cooling to 20-30 ℃, adjusting the pH value to 7.5-8, stirring for reaction, filtering to obtain a wet creatine product, cleaning a filter cake, draining, and drying to obtain creatine monohydrate.
2. The method for preparing creatine monohydrate from the aqueous solution of calcium sarcosinate as claimed in claim 1, wherein in step S1, the aqueous solution of calcium sarcosinate is placed in a reaction vessel with a stirring function, 45% to 55% of sulfuric acid is added dropwise while stirring, and the reaction is continued for 0.5 to 5h after the dropwise addition.
3. The method for preparing creatine monohydrate from an aqueous solution of calcium sarcosinate according to claim 2, wherein the PH in step S3 is adjusted to 10 with sodium hydroxide.
4. The method for preparing creatine monohydrate from the aqueous solution of calcium sarcosinate according to claim 1, wherein the aqueous solution of calcium sarcosinate is evaporated and dehydrated to a liquid weight 3 to 4 times that of calcium sarcosinate in step S3.
5. The method for preparing creatine monohydrate from the aqueous solution of calcium sarcosinate according to claim 1, wherein the amount of the material of cyanamide added dropwise in step S4 is 1.8 to 2.5 times of that of calcium sarcosinate, and the concentration of the material is 30%.
6. The method for preparing creatine monohydrate from an aqueous solution of calcium sarcosinate according to claim 1, wherein the pH of the solution is adjusted to 7.5 to 8 by 30% hydrochloric acid in step S5.
7. The method for preparing creatine monohydrate from an aqueous solution of calcium sarcosinate according to claim 6, wherein the filter cake is washed with 1 time of purified water in step S5.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202211113927.7A CN115322122A (en) | 2022-09-14 | 2022-09-14 | Method for preparing creatine monohydrate from creatine chelated calcium aqueous solution |
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| CN202211113927.7A CN115322122A (en) | 2022-09-14 | 2022-09-14 | Method for preparing creatine monohydrate from creatine chelated calcium aqueous solution |
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB775738A (en) * | 1954-11-17 | 1957-05-29 | Colgate Palmolive Co | Process for the preparation of sarcosine |
| CN1140707A (en) * | 1995-07-18 | 1997-01-22 | Skw特罗斯特贝格股份公司 | Process for preparing creatine or creatine-hydrate |
| US20040133040A1 (en) * | 2002-12-18 | 2004-07-08 | Matthias Boldt | Creatine salts and method of making same |
| CN103664665A (en) * | 2013-12-13 | 2014-03-26 | 天津天成制药有限公司 | Solid sodium sarcosine preparation method |
| CN104892440A (en) * | 2015-04-16 | 2015-09-09 | 重庆紫光化工股份有限公司 | Clean production method of glycine and derivatives thereof |
-
2022
- 2022-09-14 CN CN202211113927.7A patent/CN115322122A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB775738A (en) * | 1954-11-17 | 1957-05-29 | Colgate Palmolive Co | Process for the preparation of sarcosine |
| CN1140707A (en) * | 1995-07-18 | 1997-01-22 | Skw特罗斯特贝格股份公司 | Process for preparing creatine or creatine-hydrate |
| US20040133040A1 (en) * | 2002-12-18 | 2004-07-08 | Matthias Boldt | Creatine salts and method of making same |
| CN103664665A (en) * | 2013-12-13 | 2014-03-26 | 天津天成制药有限公司 | Solid sodium sarcosine preparation method |
| CN104892440A (en) * | 2015-04-16 | 2015-09-09 | 重庆紫光化工股份有限公司 | Clean production method of glycine and derivatives thereof |
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