CN115611758B - Method for producing sarcosine - Google Patents
Method for producing sarcosine Download PDFInfo
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- CN115611758B CN115611758B CN202211310025.2A CN202211310025A CN115611758B CN 115611758 B CN115611758 B CN 115611758B CN 202211310025 A CN202211310025 A CN 202211310025A CN 115611758 B CN115611758 B CN 115611758B
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- electrodialysis
- ethanol
- sarcosinate
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- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 title claims abstract description 257
- 108010077895 Sarcosine Proteins 0.000 title claims abstract description 156
- 229940043230 sarcosine Drugs 0.000 title claims abstract description 127
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 19
- 239000000243 solution Substances 0.000 claims abstract description 100
- 238000000909 electrodialysis Methods 0.000 claims abstract description 75
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims abstract description 32
- 229940048098 sodium sarcosinate Drugs 0.000 claims abstract description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- 238000011033 desalting Methods 0.000 claims abstract description 16
- 239000012266 salt solution Substances 0.000 claims abstract description 8
- 229940071089 sarcosinate Drugs 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 60
- 239000000463 material Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 31
- 238000001816 cooling Methods 0.000 claims description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 20
- 238000001035 drying Methods 0.000 claims description 18
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 claims description 17
- 238000002156 mixing Methods 0.000 claims description 17
- 239000011259 mixed solution Substances 0.000 claims description 16
- 238000010790 dilution Methods 0.000 claims description 9
- 239000012895 dilution Substances 0.000 claims description 9
- 238000011534 incubation Methods 0.000 claims 1
- 239000002245 particle Substances 0.000 abstract description 4
- 230000003472 neutralizing effect Effects 0.000 abstract description 3
- 238000012824 chemical production Methods 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 34
- 230000000052 comparative effect Effects 0.000 description 19
- 150000003839 salts Chemical class 0.000 description 19
- 239000011780 sodium chloride Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 239000003513 alkali Substances 0.000 description 11
- 238000010612 desalination reaction Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000007865 diluting Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 230000001105 regulatory effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 4
- 239000002699 waste material Substances 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000004321 preservation Methods 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
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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
-
- 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
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- 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
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
- C07C227/42—Crystallisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A20/00—Water conservation; Efficient water supply; Efficient water use
- Y02A20/124—Water desalination
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
Abstract
The invention belongs to the technical field of chemical production, and particularly discloses a method for producing sarcosine. The production method provided by the invention comprises the steps of neutralizing a sodium sarcosinate aqueous solution with hydrochloric acid to obtain a sarcosinate-containing salt solution; concentrating for primary desalting and electrodialysis for secondary desalting to obtain sarcosine solution; purifying and crystallizing the sarcosine solution to obtain a sarcosine product. The sarcosine particles obtained by the invention are uniform, high in purity, good in crystal form and fluidity, and convenient to transport, store and use.
Description
Technical Field
The invention belongs to the technical field of chemical production, and particularly relates to a method for producing sarcosine.
Background
Sarcosine is one of amino acids, and has remarkable effects in improving intelligence, recovering physical strength, and strengthening muscle, etc., while participating in metabolism in organism but not generating heat. Therefore, sarcosine is widely applied in the fields of medicines, foods, breeding, daily chemicals and the like.
At present, sodium sarcosinate is an important raw material for synthesizing sarcosine, and the method for preparing the sarcosine by taking the sodium sarcosinate as the raw material mainly comprises an ion exchange method and an electrodialysis method. The ion exchange method generally comprises the steps of neutralizing sodium sarcosinate with inorganic acid to generate sarcosine and sodium salt, and then adsorbing and separating the sarcosine with ion exchange resin to obtain a sarcosine product. The ion exchange method has good desalting effect, but a large amount of acid and alkali are needed to activate the ion exchange resin, so that secondary pollution is easy to form. The electrodialysis method is to carry out electrodialysis desalination on sodium sarcosinate solution, the method does not generate three wastes such as waste acid, waste alkali and the like, and has simple operation, but the electrodialysis treatment is found to be incapable of obtaining the sarcosinate product with high purity and good quality.
Therefore, it is necessary to provide a method for producing sarcosine, which improves the quality of the product of sarcosine.
Disclosure of Invention
The invention mainly solves the technical problem of providing a method for generating sarcosine, which can improve the purity of the sarcosine product.
In order to solve the technical problems, the invention provides a method for producing sarcosine, which comprises the following steps:
(1) Adjusting the pH of the aqueous solution of sodium sarcosinate to 6.5-7.0 with hydrochloric acid to obtain a salt solution containing sarcosinate;
(2) Concentrating the sarcosine-containing salt solution for one-time desalination to obtain a desalted sarcosine solution;
(3) Electrodialysis is carried out on the desalted sarcosine solution for secondary desalting to obtain a sarcosine solution;
(4) Purifying and crystallizing the sarcosine solution to obtain a sarcosine product.
As a preferred embodiment of the present invention, the concentration of the aqueous solution of sodium sarcosinate by mass is 37 to 40%, more preferably 38%.
As a preferred embodiment of the present invention, the concentrating one-time desalting comprises: concentrating the sarcosine-containing salt solution until the water content is 35-45%, cooling to separate out solid, and separating to remove the solid to obtain the desalted sarcosine solution.
As a preferred embodiment of the present invention, the concentration temperature of the sarcosinate-containing solution is controlled to be 60-65 ℃; and/or concentrating, cooling to 25-30deg.C, and precipitating solid.
As a preferred embodiment of the present invention, the electrodialysis secondary desalting comprises: and carrying out electrodialysis treatment on the desalted sarcosine solution, and stopping electrodialysis when the electric conduction of a material chamber is reduced to be lower than 200us/cm to obtain the sarcosine solution.
Further preferably, the temperature is controlled to be 20-40 ℃ and the current is controlled to be 1-10A in the electrodialysis process.
Preferably, before the desalted sarcosine solution is subjected to electrodialysis treatment, water is added for dilution; preferably, the mass of the added water is 30-40% of the mass of the aqueous solution of sodium sarcosinate, more preferably 35-40%.
Further preferably, the electrodialysis secondary desalination comprises the steps of:
Diluting desalted sarcosine solution with water, placing the diluted solution into a material chamber of electrodialysis equipment, adding deionized water with equal volume into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 20cm/s-40cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment;
In the electrodialysis process, the temperature is controlled at 20-40 ℃, the current is regulated to 1-10A, and when the conductance of a material chamber is reduced to below 200us/cm, the operation is stopped, so as to obtain the sarcosine solution.
As a preferred embodiment of the present invention, the purification of sarcosine solution comprises: concentrating the sarcosine solution to water content of 15-20% to obtain concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution, cooling for crystallization, separating crystalline solid, and drying to obtain sarcosine product.
Preferably, the mass ratio of the ethanol acetone mixed solution to the concentrated solution is (2-3): 1.
Preferably, the mass ratio of ethanol to acetone in the ethanol-acetone mixed solution is 1: (4-5).
Preferably, the concentrated solution is mixed with the ethanol-acetone mixed solution, then cooled to 10-15 ℃ and then subjected to heat preservation crystallization, and further preferably the heat preservation time is 5-7h.
The invention also provides a sarcosine product obtained by adopting the production method.
The invention provides a production method of sarcosine, which comprises the steps of neutralizing sodium sarcosinate raw materials with acid to obtain solution containing sarcosine and sodium salt, and then desalting twice, namely desalting by concentration once and desalting by electrodialysis once, concentrating and removing most of salts firstly, wherein on one hand, the pressure of electrodialysis equipment can be reduced, and more importantly, the treatment efficiency of electrodialysis can be improved, the treatment effect is improved, the salt residue in the material after electrodialysis is lower, the material loss is lower, and the yield of the product is higher. And purifying the sarcosine solution obtained after twice desalting, firstly adjusting the concentration of the sarcosine solution to ensure that the water content is 15-20%, selecting ethanol-acetone mixed solution with a certain proportion as a crystallization solvent, and crystallizing to obtain the sarcosine with uniform particles, high purity, good crystal form, good fluidity and convenient transportation, storage and use. The mother solution after crystallization can be continuously used for crystallization, so that the resource waste is not caused.
Detailed Description
The technical scheme of the present invention will be clearly and completely described in connection with the specific embodiments. It will be appreciated by those skilled in the art that the embodiments described below are merely illustrative of the present invention and should not be construed as limiting the scope of the present invention. All other embodiments, e.g., modified and substituted embodiments, which can be made by one skilled in the art without the exercise of inventive faculty, are intended to be within the scope of the invention.
The experimental methods used in the following examples are all conventional methods unless otherwise specified; the raw materials, reagents, instruments and the like used are commercially available unless otherwise specified.
The percentages in the following examples and comparative examples are mass percentages unless otherwise specified.
Example 1
The embodiment provides a method for producing sarcosine, which comprises the following steps:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.8, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 360g of water altogether, wherein the water content in the solution is 40.6%, then cooling to 28 ℃, separating out solid, filtering out the solid, namely wet salt, wherein the total amount of the sarcosine in the wet salt is 113g, the residual amount of the sarcosine in the wet salt is 0.31%, filtering the liquid to obtain a desalted sarcosine solution, diluting the desalted sarcosine solution with 360g of water concentrated before, uniformly mixing, and carrying out electrodialysis secondary desalting treatment;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 25cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 8A, and when the conductance of a material chamber is reduced to 190us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 65 ℃ until the water content is 18%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 12 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total of the sarcosine products is 261g, the calculated yield is 85.6%, the HPLC purity is 99.6%, the burning residue is 0.06%, and the drying loss is 0.16%. The prepared sarcosine particles are uniform and do not agglomerate after being placed in vacuum package.
Example 2
The embodiment provides a method for producing sarcosine, which comprises the following steps:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 7.0, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating the solution containing sarcosine and sodium chloride to 65 ℃, concentrating under negative pressure to remove water, concentrating 380g of water altogether, wherein the water content in the solution is 38.7%, then cooling to 25 ℃, separating out solid, filtering out the solid, namely wet salt, wherein the total amount of the sarcosine in the wet salt is 0.29%, diluting the filtered feed liquid which is a desalted sarcosine solution with 380g of water concentrated before, and carrying out electrodialysis secondary desalting treatment after uniform mixing;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 6A, and when the conductance of a material chamber is reduced to 193us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 16%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:5, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total sarcosine product is 263g, the calculated yield is 85.7%, the HPLC purity is 99.3%, the burning residue is 0.08%, and the drying loss is 0.15%. The prepared sarcosine particles are uniform and do not agglomerate after being placed in vacuum package.
Comparative example 1
The comparative example provides a process for the production of sarcosine comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.6, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 380g of water altogether, wherein the water content in the solution is 38.7%, then cooling to 28 ℃, separating out solids, filtering out the solids, namely wet salt, 118g of the solids, wherein the residual quantity of the sarcosine in the wet salt is 0.33%, diluting the filtered feed liquid which is a desalted sarcosine solution with 380g of water concentrated before, and carrying out electrodialysis secondary desalting treatment after uniform mixing;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 6A, and when the conductance of a material chamber is reduced to 990us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 16%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total sarcosine product is 263g, the calculated yield is 80.3%, the HPLC purity is 93.1%, the burning residue is 5.6%, and the drying loss is 0.16%.
As is clear from the comparative example, when the conductance of the material chamber is reduced to 1000us/cm or less and more than 200us/cm, the purity of the sarcosine product is affected, and the purity is reduced.
Comparative example 2
The comparative example provides a process for the production of sarcosine comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.7, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 365g of water altogether, wherein the water content in the solution is 40.2%, cooling to 28 ℃, separating out solids, filtering out the solids, namely 110g of wet salt, wherein the residual quantity of the sarcosine in the wet salt is 0.35%, diluting the filtered feed liquid with 365g of water concentrated before, and carrying out electrodialysis secondary desalination treatment after uniform mixing;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 5A, and when the conductance of a material chamber is reduced to 196us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 25%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total sarcosine product is 195g, the calculated yield is 63.6%, the HPLC purity is 99.5%, the burning residue is 0.06%, and the drying loss is 0.16%.
As is clear from the comparative example, when the sarcosine solution is purified, the water content in the concentrated solution obtained by vacuum concentration of the sarcosine solution has a significant effect on the yield of the finally obtained sarcosine product, and when the water content of the concentrated solution is 25%, the yield of the sarcosine product is only 63.6%.
Comparative example 3
The comparative example provides a process for the production of sarcosine comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.7, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 365g of water altogether, wherein the water content in the solution is 40.2%, cooling to 28 ℃, separating out solids, filtering out the solids, namely 110g of wet salt, wherein the residual quantity of the sarcosine in the wet salt is 0.35%, diluting the filtered feed liquid with 365g of water concentrated before, and carrying out electrodialysis secondary desalination treatment after uniform mixing;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 5A, and when the conductance of a material chamber is reduced to 195us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 19%, obtaining concentrated solution, mixing the concentrated solution with 1 time of ethanol-acetone mixed solution (wherein the mass ratio of ethanol to acetone is 1:4), stirring uniformly, cooling to 15 ℃, preserving heat, crystallizing for 6h, separating out crystalline solid, and drying to obtain the sarcosine product.
The total sarcosine product is 275g, the calculated yield is 84.5%, the HPLC purity is 93.6%, the burning residue is 0.26%, and the drying loss is 0.16%.
As is clear from the comparative example, when the sarcosine solution is purified, the purity of the sarcosine product is significantly reduced when the ethanol-acetone mixture solution added to the concentrate is reduced.
Comparative example 4
The comparative example provides a process for the production of sarcosine without concentration for desalting, comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.7, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Directly carrying out electrodialysis desalination treatment on a solution containing sarcosine and sodium chloride, placing the solution containing sarcosine and sodium chloride into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is adjusted to 5A, the material chamber is difficult to continuously reduce after the electric conduction is reduced to 2000us/cm, and the operation is stopped to obtain sarcosine solution;
(3) Concentrating the sarcosine solution in vacuum at 60 ℃ until the water content is 18%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total of the sarcosine products is 281g, the calculated yield is 84.2%, the HPLC purity is 91.6%, the burning residue is 2.6%, and the drying loss is 0.16%.
As is clear from the comparative example, the purity of the obtained sarcosine product is very low, namely 91.6%, by directly carrying out electrodialysis desalination treatment.
Comparative example 5
The comparative example provides a process for the production of sarcosine comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.7, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 460g of water altogether, wherein the water content in the solution is 29.6%, then cooling to 28 ℃, separating out solids, filtering out 145g of solids, wherein the residual quantity of the sarcosine in the wet salt is 16.31%, diluting the filtered feed liquid with 460g of water concentrated before, uniformly mixing, and carrying out electrodialysis secondary desalination treatment;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 5A, and when the conductance of a material chamber is reduced to 196us/cm, the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 18%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total sarcosine product is 161g, the calculated yield is 52.6%, the HPLC purity is 99.6%, the burning residue is 0.06%, and the drying loss is 0.16%.
As is clear from the comparative example, when the salt is removed by concentration, the water content after concentration is too low, and the residual amount of sarcosine in the wet salt separated by filtration is large, which results in a significant reduction in the yield of the sarcosine product.
Comparative example 6
The comparative example provides a process for the production of sarcosine comprising the steps of:
(1) 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38% is taken, and hydrochloric acid is used for adjusting the pH value to 6.7, so as to obtain solution containing the sodium sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating 260g of water altogether, wherein the water content in the solution is 48.6%, then cooling to 28 ℃, separating out solids, filtering out the solids, namely wet salt, wherein the total amount of sarcosine in the wet salt is 33g, the filtered feed liquid is desalted sarcosine solution, diluting with 260g of water concentrated before, uniformly mixing, and carrying out electrodialysis secondary desalting treatment;
(3) Placing the material liquid obtained by dilution in the step (2) into a material chamber of electrodialysis equipment, adding deionized water with the same volume as the material in the material chamber into an acid chamber and an alkali chamber of the electrodialysis equipment, starting a circulating pump of each chamber, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; in the electrodialysis process, the temperature is controlled at 30-35 ℃, the current is regulated to 5A, the material chamber is difficult to continuously reduce after the electric conduction is reduced to below 1600us/cm, and the operation is stopped to obtain sarcosine solution;
(4) Concentrating the sarcosine solution in vacuum at 62 ℃ until the water content is 18%, obtaining concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution with the mass ratio of 2 times of that of ethanol to acetone being 1:4, uniformly stirring, cooling to 15 ℃, preserving heat, crystallizing for 6 hours, separating out crystalline solid, and drying to obtain the sarcosine product.
The total of the sarcosine products is 261g, the calculated yield is 79.6%, the HPLC purity is 92.9%, the burning residue is 1.6%, and the drying loss is 0.16%.
According to the comparative example, when the concentration and the desalination are carried out, the water content after the concentration is too high, the wet salt content separated by filtration is reduced, and when the electrodialysis is carried out for desalination, the desalination effect is poor, so that the purity of the sarcosine product is influenced, and the purity of the product is reduced.
While the invention has been described in detail in the foregoing general description, embodiments and experiments, it will be apparent to those skilled in the art that modifications and improvements can be made thereto. Accordingly, such modifications or improvements may be made without departing from the spirit of the invention and are intended to be within the scope of the invention as claimed.
Claims (9)
1. A method for producing sarcosine is characterized in that,
The method comprises the steps of:
(1) Adjusting the pH of the aqueous solution of sodium sarcosinate to 6.5-7.0 with hydrochloric acid to obtain a salt solution containing sarcosinate; the mass percentage concentration of the sodium sarcosinate aqueous solution is 37-40%;
(2) Concentrating the sarcosine-containing salt solution to a water content of 35-45% to obtain desalted sarcosine solution;
(3) Carrying out electrodialysis secondary desalting on the desalted sarcosine solution, and stopping electrodialysis when the conductance of a material chamber is reduced to be below 200us/cm to obtain the sarcosine solution;
(4) Concentrating sarcosine solution to water content of 15-20% to obtain concentrated solution, mixing the concentrated solution with ethanol-acetone mixed solution, wherein the mass ratio of the ethanol-acetone mixed solution to the concentrated solution is (2-3): 1, cooling and crystallizing, separating a crystallized solid, and drying to obtain a sarcosine product.
2. The production method according to claim 1, wherein the concentration of the aqueous solution of sodium sarcosinate by mass is 38%.
3. The method according to claim 1, wherein,
In the step (2), the sarcosine-containing salt solution is concentrated to a water content of 35-45%, then cooled to separate out solids, and the solids are separated and removed to obtain a desalted sarcosine solution.
4. The method according to claim 3, wherein,
The concentration temperature of the sarcosinate-containing salt solution is controlled to be 60-65 ℃; and/or cooling to 25-30 ℃ to precipitate solid.
5. The method according to claim 1, wherein,
The temperature is controlled to be 20-40 ℃ and the current is controlled to be 1-10A in the electrodialysis process.
6. The method according to claim 1, wherein,
Before electrodialysis treatment is carried out on the desalted sarcosine solution, water is added for dilution.
7. The method according to claim 6, wherein,
The mass of the added water is 30-40% of the mass of the sodium sarcosinate aqueous solution.
8. The method according to claim 1, wherein,
The mass ratio of the ethanol to the acetone in the ethanol-acetone mixed solution is 1: (4-5); and/or the number of the groups of groups,
Cooling to 10-15deg.C, and crystallizing.
9. The method according to claim 8, wherein the incubation time is 5-7 hours.
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Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19920962A1 (en) * | 1999-05-06 | 2000-11-16 | Basf Ag | Production of a sarcosine solution with a predetermined pH comprises subjecting a crude sarcosine solution to bipolar electrodialysis, useful for e.g. creatine production |
| CN1962611A (en) * | 2005-11-11 | 2007-05-16 | 重庆三峡英力化工有限公司 | Process for preparing glycine using hydroxy-acetonitrile method |
| CN101407479A (en) * | 2007-10-12 | 2009-04-15 | 天津天成制药有限公司 | Preparation of sarcosine |
| CN103964989A (en) * | 2014-01-27 | 2014-08-06 | 重庆紫光化工股份有限公司 | System for continuously separating and purifying amino acid from water solution of amino acid containing alkaline metal salt |
| CN104744280A (en) * | 2015-04-07 | 2015-07-01 | 湖北锡太化工有限公司 | Method of preparing sarcosine by bipolar membrane electrodialysis process |
-
2022
- 2022-10-25 CN CN202211310025.2A patent/CN115611758B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19920962A1 (en) * | 1999-05-06 | 2000-11-16 | Basf Ag | Production of a sarcosine solution with a predetermined pH comprises subjecting a crude sarcosine solution to bipolar electrodialysis, useful for e.g. creatine production |
| CN1962611A (en) * | 2005-11-11 | 2007-05-16 | 重庆三峡英力化工有限公司 | Process for preparing glycine using hydroxy-acetonitrile method |
| CN101407479A (en) * | 2007-10-12 | 2009-04-15 | 天津天成制药有限公司 | Preparation of sarcosine |
| CN103964989A (en) * | 2014-01-27 | 2014-08-06 | 重庆紫光化工股份有限公司 | System for continuously separating and purifying amino acid from water solution of amino acid containing alkaline metal salt |
| CN104744280A (en) * | 2015-04-07 | 2015-07-01 | 湖北锡太化工有限公司 | Method of preparing sarcosine by bipolar membrane electrodialysis process |
Non-Patent Citations (1)
| Title |
|---|
| 氨基酸溶液脱盐技术的进展;甘林火，翁连进;《福建化工》(第4期);第72-73页 * |
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