Diacid citrate and method for its preparation
High-purity creatine citrate was prepared by temperature-controlled reaction and crystallization technology, which solved the problems of low purity and difficulty in controlling solubility in the existing technology. This enabled the industrial production of high-purity and high-solubility creatine citrate, which can be widely used in food, beverage additives and other fields.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- DONGYING JUNYUAN PETROLEUM TECH DEV CO LTD
- Filing Date
- 2026-03-26
- Publication Date
- 2026-06-30
AI Technical Summary
The existing preparation process for bis(creatine) citrate requires harsh reaction conditions, resulting in low product purity and difficulty in controlling solubility, which affects its application in food, beverage additives, and other fields.
By employing temperature-controlled reaction and crystallization techniques, high-purity creatine citrate is prepared by reacting creatine monohydrate with citric acid at a specific temperature, followed by filtration and drying. This method is suitable for industrial production.
The prepared creatine citrate has a purity of ≥99.6% and a molar yield of ≥90%, making it suitable for use in food, beverage additives, health products, and pharmaceutical raw materials, thus solving the problems of purity and solubility.
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Abstract
Description
Technical Field
[0001] This invention relates to the field of chemical synthesis technology, specifically to a creatine citrate and its preparation method. Background Technology
[0002] Creatine citrate is a white crystalline powder. Due to its excellent fatigue recovery effect, it is widely used in many fields such as food and beverage additives, health products, pharmaceutical raw materials, pharmaceutical chemical intermediates, daily chemical raw materials, feed additives, and veterinary drug raw materials. Market demand continues to grow. When creatine citrate is applied to ready-to-drink sports drinks, effervescent tablets, and oral liquids, it produces a refreshing taste without precipitation after reconstitution.
[0003] The current preparation of creatine citrate suffers from harsh reaction conditions and low product purity. Solubility is a key factor affecting the performance of creatine citrate in applications, and low purity makes it difficult to control solubility, thus affecting its application.
[0004] Therefore, providing a product with high purity and good solubility of creatine citrate has become a technical problem that urgently needs to be solved in this field. Summary of the Invention
[0005] In view of this, the present invention provides creatine citrate and its preparation method. In this method, creatine monohydrate is used as the creatine source, and creatine monohydrate reacts with citric acid in a reaction solvent. The creatine citrate is obtained through temperature-controlled reaction, temperature-controlled crystallization, filtration, and drying. The preparation process of the present invention is simple to operate, with mild and easily controllable reaction conditions. The resulting product has a molar yield ≥90% and a purity ≥99.6%, making it suitable for large-scale industrial production. The obtained creatine citrate is a white crystalline powder that can be widely used in food and beverage additives, health products, pharmaceutical raw materials, daily chemical raw materials, and feed and veterinary drug additives.
[0006] The technical solution of the present invention is as follows: A type of creatine citrate with the molecular formula C 14 H 26 N6O 11 Its molecular weight is 454.4, CAS: 331942-93-9; its structural formula is as follows:
[0007] Preferably, the above-mentioned creatine citrate is prepared by: using creatine monohydrate as raw material, adding citric acid to the creatine monohydrate solution, keeping the reaction at 0-70℃ for 2-8 hours, then cooling to 0-30℃, stirring for 1-5 hours, filtering, and drying the solid to obtain creatine citrate.
[0008] Creatine citrate is used as a fatigue recovery agent and is widely used in food and beverage additives; health products and pharmaceutical raw materials; pharmaceutical and chemical intermediates; raw materials for daily chemical products; feed additives; veterinary drug raw materials, etc.
[0009] A method for preparing creatine citrate, comprising the following steps: Step 1: Add the reaction solvent to the container, and add creatine monohydrate under stirring to obtain solution A; Step 2: Control the temperature of solution A to 0-70℃, add citric acid, stir, and obtain solution B; Step 3: Continue to keep solution B at 0-70℃ for 2-8 hours, then cool to 0-30℃ and stir for 1-5 hours to induce crystallization. Step 4: After filtration, collect the filter cake; after drying the filter cake, obtain dicreatine citrate.
[0010] Preferably, in step one, the reaction solvent is one or a mixture of two or three of water, methanol, and ethanol.
[0011] Preferably, the reaction solvent is ethanol.
[0012] Preferably, in step one, the mass ratio of creatine monohydrate to the reaction solvent is 1:1-6.
[0013] Preferably, the mass ratio of creatine monohydrate to the reaction solvent is 1:4.
[0014] Preferably, in step two, the citric acid is citric acid monohydrate or anhydrous citric acid; the amount of citric acid added is calculated based on the amount of creatine monohydrate added, and the mass ratio of creatine monohydrate to citric acid is 1:1.0-2.0.
[0015] Preferably, the mass ratio of creatine monohydrate to citric acid is 1:1.4-1.5.
[0016] Preferably, in step three, the temperature of the heat preservation reaction is 50-55℃, and the reaction time is 3-5h.
[0017] Preferably, in step three, the crystallization temperature is 0-5℃ and the stirring time is 1-2h.
[0018] Compared with the prior art, the beneficial effects of the present invention are as follows: 1. The dicreatine citrate prepared by this invention has a purity of ≥99.6%.
[0019] 2. The preparation method of the present invention has a molar yield ≥90%. Detailed Implementation
[0020] To enable those skilled in the art to better understand the technical solutions of this invention, the technical solutions of this invention will be clearly and completely described below in conjunction with the embodiments of this invention. Obviously, the described embodiments are only some embodiments of this invention, and not all embodiments. Based on the embodiments of this invention, all other embodiments obtained by those skilled in the art without creative effort should fall within the scope of protection of this invention.
[0021] Example 1 A creatine citrate, prepared by the following method: Step 1: Add 600g of purified water to a 1000ml container, and add 150g of creatine monohydrate at 200r / min to obtain solution A; Step 2: Heat solution A to 53°C, add 210g of citric acid monohydrate, stir, and obtain solution B; Step 3: Keep solution B at 53℃ for 3 hours, then cool it down to 4℃, stir for 2 hours, crystallize, and filter. Step 4: The filtered solid was vacuum dried at 45°C and -0.08 MPa for 5 hours to obtain 290 g of creatine citrate, which was a white crystalline powder. Based on creatine monohydrate, the molar yield was 90% and the purity was 99.6%.
[0022] Example 2 A creatine citrate, prepared by the following method: Step 1: Add 600g of methanol to a 1000ml container, and add 150g of creatine monohydrate at 200r / min to obtain solution A; Step 2: Heat solution A to 54°C, add 210g of anhydrous citric acid, stir, and obtain solution B; Step 3: Keep solution B at 54℃ for 4 hours, then cool it down to 5℃, stir for 2 hours, crystallize, and filter. Step 4: The filtered solid was vacuum dried at 45°C and -0.08 MPa for 5.5 h to obtain 295 g of creatine citrate, which is a white crystalline powder. Based on creatine monohydrate, the molar yield was 92% and the purity was 99.8%.
[0023] Example 3 A creatine citrate, prepared by the following method: Step 1: Add 600g of ethanol to a 1000ml container, and add 150g of creatine monohydrate at 200r / min to obtain solution A; Step 2: Heat solution A to 50°C, add 210g of citric acid monohydrate, stir, and obtain solution B; Step 3: Keep solution B at 50℃ for 5 hours, then cool it down to 0℃, stir for 2 hours, crystallize, and filter. Step 4: The filtered solid was vacuum dried at 45°C and -0.08 MPa for 6 hours to obtain 292 g of creatine citrate, which was a white crystalline powder. Based on creatine monohydrate, the molar yield was 91% and the purity was 99.7%.
[0024] Although the present invention has been described in detail with reference to preferred embodiments, it is not limited thereto. Various equivalent modifications or substitutions can be made to the embodiments of the present invention by those skilled in the art without departing from the spirit and essence of the invention, and such modifications or substitutions should all be within the scope of the present invention. Any variations or substitutions that can be easily conceived by those skilled in the art within the technical scope disclosed in the present invention should also be covered within the protection scope of the present invention. Therefore, the protection scope of the present invention should be determined by the scope of the claims.
Claims
1. A creatine citrate, characterized in that, The molecular formula is C 14 H 26 N6O 11 Its molecular weight is 454.4, CAS number 331942-93-9; its structural formula is as follows: 。 2. The creatine citrate as described in claim 1, characterized in that, The preparation method of this creatine citrate is as follows: using creatine monohydrate as raw material, citric acid is added to the creatine monohydrate solution, and the reaction is carried out at 0-70℃ for 2-8 hours. Then, the temperature is lowered to 0-30℃, stirred for 1-5 hours, filtered, and the solid is dried to obtain creatine citrate.
3. The method for preparing creatine citrate as described in claim 2, characterized in that, The steps are as follows: Step 1: Add the reaction solvent to the container, and add creatine monohydrate under stirring to obtain solution A; Step 2: Control the temperature of solution A to 0-70℃, add citric acid, stir, and obtain solution B; Step 3: Continue to keep solution B at 0-70℃ for 2-8 hours, then cool to 0-30℃ and stir for 1-5 hours to induce crystallization. Step 4: After filtration, collect the filter cake; after drying the filter cake, obtain dicreatine citrate.
4. The method for preparing creatine citrate as described in claim 3, characterized in that, In step one, the reaction solvent is one or a mixture of two or three of water, methanol, and ethanol.
5. The method for preparing creatine citrate as described in claim 4, characterized in that, The reaction solvent is ethanol.
6. The method for preparing creatine citrate as described in claim 3, characterized in that, In step one, the mass ratio of creatine monohydrate to the reaction solvent is 1:1-6.
7. The method for preparing creatine citrate as described in claim 6, characterized in that, The mass ratio of creatine monohydrate to the reaction solvent is 1:
4.
8. The method for preparing creatine citrate as described in claim 3, characterized in that, In step two, the citric acid is either citric acid monohydrate or anhydrous citric acid; the amount of citric acid added is calculated based on the amount of creatine monohydrate added, and the mass ratio of creatine monohydrate to citric acid is 1:1.0-2.
0.
9. The method for preparing creatine citrate as described in claim 8, characterized in that, The mass ratio of creatine monohydrate to citric acid is 1:1.4-1.
5.
10. The method for preparing creatine citrate as described in claim 3, characterized in that, In step three, the temperature for the heat preservation reaction is 50-55℃, and the reaction time is 3-5h; the crystallization temperature is 0-5℃, and the stirring time is 1-2h.