CN115772100B - Method for continuously producing creatine monohydrate by micro-channel reaction device - Google Patents
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- 238000006243 chemical reaction Methods 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title claims abstract description 33
- MEJYXFHCRXAUIL-UHFFFAOYSA-N 2-[carbamimidoyl(methyl)amino]acetic acid;hydrate Chemical compound O.NC(=N)N(C)CC(O)=O MEJYXFHCRXAUIL-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 229960004826 creatine monohydrate Drugs 0.000 title claims abstract description 31
- 239000007864 aqueous solution Substances 0.000 claims abstract description 66
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims abstract description 51
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims abstract description 48
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 30
- 108010077895 Sarcosine Proteins 0.000 claims abstract description 26
- 229940043230 sarcosine Drugs 0.000 claims abstract description 25
- CVSVTCORWBXHQV-UHFFFAOYSA-N creatine Chemical compound NC(=[NH2+])N(C)CC([O-])=O CVSVTCORWBXHQV-UHFFFAOYSA-N 0.000 claims abstract description 24
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229940106681 chloroacetic acid Drugs 0.000 claims abstract description 16
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000243 solution Substances 0.000 claims abstract description 13
- 229960003624 creatine Drugs 0.000 claims abstract description 12
- 239000006046 creatine Substances 0.000 claims abstract description 12
- 238000005086 pumping Methods 0.000 claims abstract description 12
- 239000012295 chemical reaction liquid Substances 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims description 6
- 238000006386 neutralization reaction Methods 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims 1
- 239000011259 mixed solution Substances 0.000 claims 1
- 238000005457 optimization Methods 0.000 abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- 238000005265 energy consumption Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 102000004364 Myogenin Human genes 0.000 description 1
- 108010056785 Myogenin Proteins 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- FFBHFFJDDLITSX-UHFFFAOYSA-N benzyl N-[2-hydroxy-4-(3-oxomorpholin-4-yl)phenyl]carbamate Chemical compound OC1=C(NC(=O)OCC2=CC=CC=C2)C=CC(=C1)N1CCOCC1=O FFBHFFJDDLITSX-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 229940048098 sodium sarcosinate Drugs 0.000 description 1
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for continuously producing creatine monohydrate by a microchannel reaction device, which comprises the following steps: pumping monomethylamine aqueous solution and chloroacetic acid aqueous solution into a micro-channel reactor I at the same time to react to generate sarcosine aqueous solution; pumping the sarcosine aqueous solution and the sodium hydroxide solution into a micro-channel reactor II at the same time for reaction, and distilling under reduced pressure after the reaction to obtain a concentrated sarcosine aqueous solution; pumping the concentrated sarcosine aqueous solution and the cyanamide aqueous solution into a tubular reactor III at the same time for reaction to obtain creatine reaction liquid; and (3) carrying out post-treatment on the creatine reaction liquid to obtain creatine monohydrate. According to the invention, the micro-channel reaction device is utilized to continuously produce the creatine monohydrate, so that the mass transfer rate and the heat transfer rate are greatly improved, the molar ratio of chloroacetic acid to monomethylamine is reduced from intermittent 1:8-12 to intermittent 1:5-7 through the optimization of reaction conditions, the consumption of monomethylamine is greatly reduced, and the molar yield is also improved.
Description
Technical Field
The invention relates to a method for producing creatine monohydrate, in particular to a method for continuously producing creatine monohydrate by a micro-channel reaction device, belonging to the technical field of synthesis of large health products.
Background
Creatine (Creatine), also known as myogenin, is an energy reserve substance present in muscle tissue and can be used as a pharmaceutical product, energy supplement, food additive, etc.
In the prior art, a plurality of methods for synthesizing creatine monohydrate exist, including: 1. the sodium sarcosinate reacts with the cyanamide aqueous solution, and hydrochloric acid is continuously used for adjusting the pH value of the reaction solution to be 9-10, so that creatine monohydrate is obtained; 2. preparing creatine monohydrate by reacting an aqueous solution of hydroxyacetonitrile, an aqueous solution of monomethylamine and an aqueous solution of cyanamide; 3. the chloroacetic acid aqueous solution, the monomethylamine aqueous solution and the cyanamide aqueous solution react to synthesize creatine monohydrate. The above processes are all batch kettle processes and have different disadvantages, and in the process 1, a large amount of inorganic salt is introduced in the process of adjusting the pH value of the reaction liquid, and a large amount of deionized water is needed for washing, so that a large amount of salt-containing wastewater is difficult to treat; the processes 2 and 3 use aqueous solutions of monomethylamine, monomethylamine is volatilized in the reaction process, and the volatilized and residual monomethylamine must be recovered, so that the reaction time, the operation are complicated and the energy consumption is high. In addition, the molar ratio of chloroacetic acid to monomethylamine is 1:8-12, a large amount of methylamine hydrochloride is generated in the reaction, the purification of subsequent products is difficult, and the yield is only about 50%. Therefore, finding a method for preparing creatine monohydrate with simple operation, high yield and low energy consumption is a technical problem which needs to be solved urgently at present.
Disclosure of Invention
The invention aims to provide a method for continuously producing creatine monohydrate by a microchannel reaction device, which realizes continuous production of creatine monohydrate by using the microchannel reaction device, reduces the consumption of raw material monomethylamine aqueous solution, greatly shortens monomethylamine recovery time, reduces energy consumption, improves production efficiency, improves reaction yield by screening process conditions, and is more suitable for industrial production.
In order to achieve the above purpose, the present invention provides the following specific technical solutions:
A method for continuously producing creatine monohydrate by means of a microchannel reactor, the method comprising the steps of:
(1) Pumping monomethylamine aqueous solution and chloroacetic acid aqueous solution into a micro-channel reactor I at the same time to react to generate sarcosine aqueous solution;
(2) Pumping the sarcosine aqueous solution and the sodium hydroxide solution into a micro-channel reactor II at the same time for neutralization reaction, and distilling under reduced pressure after the reaction to obtain a concentrated sarcosine aqueous solution;
(3) Pumping the concentrated sarcosine aqueous solution and the cyanamide aqueous solution into a tubular reactor III at the same time for reaction to obtain creatine reaction liquid;
(4) And (3) carrying out post-treatment on the creatine reaction liquid to obtain creatine monohydrate.
Further, in the step (1), when the concentration of the monomethylamine aqueous solution is 40wt% and the concentration of the chloroacetic acid aqueous solution is 70wt%, the volume flow ratio of the monomethylamine aqueous solution to the chloroacetic acid aqueous solution is 4 to 7:1, for example, 4:1, 5:1, 6:1, 7:1, preferably 4.3:1.
Further, in step (1), the temperature in the microchannel reactor I is 5 to 30 ℃, for example 5 ℃,10 ℃, 15 ℃, 20 ℃, 25 ℃, 30 ℃, preferably 10 ℃; the residence time of the material in the microchannel reactor I is 12-20 min, for example 12min, 14min, 16min, 18min, 20min, preferably 16min.
In the step (2), when the concentration of the sodium hydroxide aqueous solution is 32wt%, the volume flow ratio of the sodium hydroxide aqueous solution to the sarcosine aqueous solution is 0.05-0.2:1, preferably 0.15:1, so as to achieve the purpose of neutralizing the byproduct methylamine chloride in the decomposition reaction solution.
Further, in the step (2), the temperature in the microchannel reactor II is 20-40 ℃, such as 20 ℃, 30 ℃, 40 ℃, preferably 30 ℃; the residence time of the material in the microchannel reactor II is 4-8 min, for example 4min, 5min, 6min, 7min, 8min, preferably 5min.
Further, in the step (3), when the concentration of the concentrated aqueous solution of sarcosine is 60wt% and the concentration of the aqueous solution of cyanamide is 30wt%, the volume flow ratio of the concentrated aqueous solution of sarcosine to the aqueous solution of cyanamide is 1:1 to 1.3, for example, 1:1, 1:1.1, 1:1.2, 1:1.3, preferably 1:1.2.
Further, in the step (3), the temperature in the tubular reactor III is 60 to 80 ℃, for example 60 ℃, 65 ℃, 70 ℃, 75 ℃, 80 ℃, preferably 75 ℃; the residence time of the material in the tubular reactor III is 10 to 30min, for example 10min, 15min, 20min, 25min, 30min, preferably 20min.
Further, in the step (4), the post-treatment comprises the steps of cooling, filtering, washing, filtering and drying the creatine reaction liquid to obtain creatine monohydrate.
Furthermore, the creatine monohydrate is produced by the micro-channel reaction device, and the micro-channel reaction device comprises a micro-channel reactor I, a micro-channel reactor II and a tubular reactor III which are sequentially connected in series. The micro-channel reactor I, the micro-channel reactor II and the tubular reactor III can be obtained through the market and are made of 316L, HC-276 silicon carbide and the like, and the internal structures of the micro-channel reactor I and the micro-channel reactor II comprise but are not limited to rectangular, heart-shaped and the like. The micro-channel reactors I and II can adopt plate-type micro-channel reactors or tubular micro-channel reactors, and the diameter is 1-2 mm. The diameter of the tubular reactor III is 5-10 mm.
Compared with the prior art, the invention has the following advantages:
1. The method of the invention utilizes the micro-channel reaction device to prepare the creatine monohydrate, skillfully converts the disadvantage of monomethylamine volatilization in the reaction process of chloroacetic acid and monomethylamine into advantages, namely, liquid-liquid homogeneous phase reaction is converted into gas-liquid two-phase reaction, the generation of bubbles increases the gas-liquid phase interface area, and the gas-liquid mass transfer process is strengthened, thereby accelerating the reaction rate.
2. According to the method, the micro-channel reaction device is used for preparing the creatine monohydrate, the mass transfer process is enhanced, the consumption of a monomethylamine aqueous solution is reduced, the molar ratio of the intermittent process chloroacetic acid to the monomethylamine is reduced to 1:5-7 from 1:8-12, the generation of byproduct methylamine hydrochloride is obviously reduced, the production efficiency is improved, and meanwhile, the material consumption and the energy consumption are reduced.
3. According to the method, the micro-channel reaction device is used for preparing the creatine monohydrate, so that the accurate temperature control is realized, the formation of local hot spots caused by exothermic reaction is avoided, and further, obvious side reactions influenced by temperature in the reaction process, such as side reactions of self-polymerization of cyanamide, self-polymerization of cyanamide and water into urea, self-polymerization of creatine, decomposition of creatine and the like, are inhibited, the reaction selectivity is improved, and the product yield is improved through the optimization of reaction conditions.
4. In the traditional batch production process, the yield of creatine monohydrate is generally about 50%, and the highest product yield can reach 68% through the optimization of reaction conditions.
Drawings
FIG. 1 is a flow chart of a process for continuously producing creatine monohydrate by a microchannel reactor according to the present invention.
Detailed Description
The invention will be described in further detail with reference to the following specific embodiments, but the scope of the invention is not limited thereto. Unless otherwise indicated, all the starting materials used in the examples below were commercially available.
In the following embodiments, the microchannel reactor I and the microchannel reactor II may be plate-type or tubular microchannel reactors, the diameters of the microchannel reactor I and the microchannel reactor II are 1-2 mm, and the diameter of the tubular reactor III is 5-10 mm.
Example 1
Pumping a monomethylamine aqueous solution with the mass fraction of 40% and a 70% chloroacetic acid aqueous solution into a micro-channel reactor I at the volume flow ratio of 4.3:1, wherein the reaction temperature is 10 ℃, and the residence time is 16min, so as to obtain a sarcosine aqueous solution; pumping 32% sodium hydroxide solution and sarcosine water solution into a micro-channel reactor II at the same time according to the volume flow ratio of 0.15:1, wherein the reaction temperature is 30 ℃, and the residence time is 5min; after the reaction is finished, decompressing and distilling to remove water to obtain concentrated sarcosine water solution, wherein the concentration of the concentrated sarcosine water solution is 60%;
Pumping concentrated sarcosinate aqueous solution and 30% of cyanamide aqueous solution into a tubular reactor III at the volume flow ratio of 1:1.2 for reaction at the reaction temperature of 75 ℃ for 20min to obtain creatine reaction liquid; the reaction solution was cooled, filtered, washed with water, filtered and dried to give a product having a purity (HPLC) of 99.95% and a molar yield of 68% based on chloroacetic acid.
Examples 2 to 3
Creatine monohydrate was produced according to the method of example 1, except that: the volume flow ratio of 40% monomethylamine aqueous solution to 70% chloroacetic acid aqueous solution was varied, with the remaining reaction conditions unchanged. The results are shown below:
Examples 4 to 7
Creatine monohydrate was produced according to the method of example 1, except that: the reaction temperature and the residence time of the monomethylamine aqueous solution and the chloroacetic acid aqueous solution in the micro-channel reactor I are changed, and the rest reaction conditions are unchanged. The results are shown below:
Examples 8 to 9
Creatine monohydrate was produced according to the method of example 1, except that: the volume flow ratio of the 32% sodium hydroxide solution to the sarcosine aqueous solution was changed, and the remaining reaction conditions were unchanged. The results are shown below:
Examples 10 to 13
Creatine monohydrate was produced according to the method of example 1, except that: the reaction temperature and the residence time of the 32% sodium hydroxide solution and the sarcosine aqueous solution micro-channel reactor II are changed, and the rest reaction conditions are unchanged. The results are shown below:
Examples 14 to 15
Creatine monohydrate was produced according to the method of example 1, except that: the volume flow ratio of the concentrated sarcosine aqueous solution to the cyanamide aqueous solution is changed, and the rest reaction conditions are unchanged. The results are shown below:
Examples 16 to 19
Creatine monohydrate was produced according to the method of example 1, except that: the reaction temperature and the residence time of the tubular reactor III are changed, and the rest reaction conditions are unchanged. The remaining reaction conditions were unchanged. The results are shown below:
Claims (5)
1. A method for continuously producing creatine monohydrate by means of a microchannel reactor, comprising the steps of:
(1) Pumping monomethylamine aqueous solution and chloroacetic acid aqueous solution into a micro-channel reactor I at the same time to react to generate sarcosine aqueous solution;
(2) Pumping the sarcosine aqueous solution and the sodium hydroxide solution into a micro-channel reactor II at the same time for neutralization reaction, and distilling under reduced pressure after the reaction to obtain a concentrated sarcosine aqueous solution;
(3) Pumping the concentrated sarcosine aqueous solution and the cyanamide aqueous solution into a tubular reactor III at the same time for reaction to obtain creatine reaction liquid;
(4) Carrying out post-treatment on the creatine reaction liquid to obtain creatine monohydrate;
In the step (1), the concentration of the monomethylamine aqueous solution is 40wt%, the concentration of the chloroacetic acid aqueous solution is 70wt%, and the volume flow ratio of the monomethylamine aqueous solution to the chloroacetic acid aqueous solution is 4-7:1;
in the step (1), the temperature in the micro-channel reactor I is 5-30 ℃, and the residence time of the mixed solution in the micro-mixer is 12-20 min;
In the step (3), the concentration of the concentrated sarcosine aqueous solution is 60wt%, the concentration of the cyanamide aqueous solution is 30wt%, and the volume flow ratio of the concentrated sarcosine aqueous solution to the cyanamide aqueous solution is 1:1-1.3;
in the step (3), the temperature in the tubular reactor III is 60-80 ℃, and the residence time of the materials in the tubular reactor III is 10-30 min.
2. The method according to claim 1, characterized in that: in the step (2), the concentration of the sodium hydroxide aqueous solution is 32wt%, and the volume flow ratio of the sodium hydroxide aqueous solution to the sarcosine aqueous solution is 0.05-0.2:1.
3. The method according to claim 1, characterized in that: in the step (2), the temperature in the micro-channel reactor II is 20-40 ℃, and the retention time of the materials in the micro-channel reactor II is 4-8 min.
4. The method according to claim 1, characterized in that: the micro-channel reactor I, the micro-channel reactor II and the tubular reactor III are sequentially connected in series, and the micro-channel reactor I and the micro-channel reactor II are plate-type micro-channel reactors or tubular micro-channel reactors.
5. The method according to claim 1, characterized in that: the diameters of the micro-channel reactor I and the micro-channel reactor II are 1-2 mm, and the diameter of the tubular reactor III is 5-10 mm.
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| CN116924942A (en) * | 2023-05-19 | 2023-10-24 | 山东凯密斯新材料科技有限公司 | A kind of synthesis method of creatine |
| CN117756679A (en) * | 2023-12-04 | 2024-03-26 | 宁夏大学 | Method for reducing content of trace and trace impurities in creatine monohydrate |
| CN118993942B (en) * | 2024-08-07 | 2025-07-11 | 宁夏恒康科技有限公司 | A method for synthesizing creatine monohydrate from glycine |
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| GB775738A (en) * | 1954-11-17 | 1957-05-29 | Colgate Palmolive Co | Process for the preparation of sarcosine |
| CN1240207A (en) * | 1998-06-19 | 2000-01-05 | 李森 | Production process of high-purity creatine and its monohydrate |
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