CN115611758A - Production method of sarcosine - Google Patents
Production method of sarcosine Download PDFInfo
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- CN115611758A CN115611758A CN202211310025.2A CN202211310025A CN115611758A CN 115611758 A CN115611758 A CN 115611758A CN 202211310025 A CN202211310025 A CN 202211310025A CN 115611758 A CN115611758 A CN 115611758A
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- sarcosine
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- electrodialysis
- ethanol
- desalted
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- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 title claims abstract description 296
- 108010077895 Sarcosine Proteins 0.000 title claims abstract description 163
- 229940043230 sarcosine Drugs 0.000 title claims abstract description 148
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 27
- 239000000243 solution Substances 0.000 claims abstract description 108
- 238000000909 electrodialysis Methods 0.000 claims abstract description 77
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
- ZUFONQSOSYEWCN-UHFFFAOYSA-M sodium;2-(methylamino)acetate Chemical compound [Na+].CNCC([O-])=O ZUFONQSOSYEWCN-UHFFFAOYSA-M 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 15
- 229940048098 sodium sarcosinate Drugs 0.000 claims abstract description 15
- 238000010612 desalination reaction Methods 0.000 claims abstract description 12
- 239000012266 salt solution Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 59
- 239000000463 material Substances 0.000 claims description 41
- 239000007787 solid Substances 0.000 claims description 36
- 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
- 238000011033 desalting Methods 0.000 claims description 19
- 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
- 239000011259 mixed solution Substances 0.000 claims description 17
- 238000001816 cooling Methods 0.000 claims description 15
- 238000002425 crystallisation Methods 0.000 claims description 14
- 230000008025 crystallization Effects 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- 238000000746 purification Methods 0.000 claims description 3
- 239000002245 particle Substances 0.000 abstract description 4
- 238000012824 chemical production Methods 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract description 2
- 230000003472 neutralizing effect Effects 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
- 238000000034 method Methods 0.000 description 18
- 239000011780 sodium chloride Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000003513 alkali Substances 0.000 description 11
- 239000008367 deionised water Substances 0.000 description 9
- 229910021641 deionized water Inorganic materials 0.000 description 9
- 238000007865 diluting Methods 0.000 description 8
- 238000010790 dilution Methods 0.000 description 8
- 239000012895 dilution Substances 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 7
- 229940071089 sarcosinate Drugs 0.000 description 7
- 230000004580 weight loss Effects 0.000 description 7
- 230000000694 effects Effects 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000004321 preservation Methods 0.000 description 3
- 239000002699 waste material Substances 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
- 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
- 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
- 230000001771 impaired effect Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- 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
Landscapes
- 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 salt solution containing sarcosine; then, carrying out concentration primary desalination and electrodialysis secondary desalination to obtain a sarcosine solution; and purifying and crystallizing the sarcosine solution to obtain the sarcosine product. The sarcosine obtained by the invention has the advantages of uniform particles, high purity, good crystal form and good fluidity, and is 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, participates in metabolism in a living body but does not generate heat, and has remarkable effects in improving intelligence, restoring physical strength, strengthening muscles and the like. Therefore, sarcosine is widely used in the fields of medicines, foods, breeding, daily chemicals, and the like.
At present, sodium sarcosine is an important raw material for synthesizing the sarcosine, and methods for preparing the sarcosine by taking the sodium sarcosine as the raw material mainly comprise an ion exchange method and an electrodialysis method. The ion exchange method generally comprises the steps of neutralizing sodium sarcosinate by inorganic acid to generate sarcosine and sodium salt, and then adsorbing and separating the sarcosine by ion exchange resin to obtain a sarcosine product. The ion exchange method has good desalting effect, but needs a large amount of acid and alkali to activate the ion exchange resin, and is easy to cause secondary pollution. The electrodialysis method is used for carrying out electrodialysis desalination on the sodium sarcosinate solution, the method does not generate waste acid, waste alkali and the like, and is simple to operate, but the electrodialysis treatment cannot be used for obtaining the high-purity and good-quality sarcosine product.
Therefore, there is a need to provide a method for producing sarcosine, which can improve the product quality 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 a sarcosine product.
In order to solve the above technical problems, the present invention provides a method for producing sarcosine, which comprises the steps of:
(1) Adjusting the pH value of the sarcosine sodium aqueous solution to 6.5-7.0 by using hydrochloric acid to obtain a salt solution containing the sarcosine;
(2) Concentrating the salt solution containing the sarcosine for primary desalination to obtain a desalted sarcosine solution;
(3) Carrying out electrodialysis secondary desalination on the desalted sarcosine solution to obtain a sarcosine solution;
(4) And purifying and crystallizing the sarcosine solution to obtain a sarcosine product.
In a preferred embodiment of the present invention, the concentration of the sodium sarcosinate aqueous solution is 37 to 40% by mass, and more preferably 38% by mass.
As a preferred embodiment of the present invention, the concentration primary desalting comprises: and concentrating the sarcosine-containing salt solution until the water content is 35-45%, cooling to separate out solids, and separating to remove the solids to obtain the desalted sarcosine solution.
As a preferred embodiment of the present invention, the concentration temperature of the sarcosine-containing salt solution is controlled to 60 to 65 ℃; and/or, cooling to 25-30 ℃ after concentration to precipitate a solid.
As a preferred embodiment of the present invention, the electrodialysis secondary desalination comprises: and (3) carrying out electrodialysis treatment on the desalted sarcosine solution, and stopping electrodialysis when the conductivity of a material chamber is reduced to be below 200us/cm to obtain the sarcosine solution.
Further preferably, the temperature in the electrodialysis process is controlled to be 20-40 ℃, and the current is 1-10A.
Preferably, before the desalted sarcosine solution is subjected to electrodialysis treatment, water is added for dilution; the mass of the added water is preferably 30-40%, more preferably 35-40% of the mass of the sodium sarcosinate aqueous solution.
Further preferably, the electrodialysis secondary desalination comprises the steps of:
diluting the desalted sarcosine solution by adding water, then placing the diluted sarcosine solution into a material chamber of an electrodialysis device, 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 device, then starting a circulating pump of each chamber, adjusting the flow rate to 20-40 cm/s, starting a power supply of the electrodialysis device, and starting electrodialysis treatment;
controlling the temperature at 20-40 deg.C during electrodialysis, adjusting current to 1-10A, and stopping operation when the conductivity of material chamber drops below 200us/cm to obtain sarcosine solution.
As a preferred embodiment of the present invention, the purification of sarcosine solution comprises: firstly, concentrating the sarcosine solution until the water content is 15-20% to obtain a concentrated solution, mixing the concentrated solution with an ethanol-acetone mixed solution, cooling for crystallization, separating a crystalline solid, and drying to obtain the 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 the temperature is reduced to 10-15 ℃, and then the heat preservation crystallization is carried out, and further, the heat preservation time is preferably 5-7h.
The invention also provides a sarcosine product obtained by the production method.
The invention provides a method for producing sarcosine, wherein a sarcosine sodium raw material is neutralized by acid to obtain a solution containing sarcosine and sodium salt, and then the solution is subjected to two times of desalting, namely one-time concentration desalting and one-time electrodialysis desalting, most of salt is removed by concentration, so that the pressure of electrodialysis equipment can be reduced, more importantly, the treatment efficiency of electrodialysis can be improved, the treatment effect is improved, the salt residue in the material subjected to electrodialysis is lower, the material loss is lower, and the product yield is higher. And then purifying the sarcosine solution obtained after the two desalting steps, 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 obtaining the crystallized sarcosine with uniform particles, high purity, good crystal form, good fluidity and convenient transportation, storage and use. The mother liquor can be continuously used for crystallization after crystallization, and resource waste is not caused.
Detailed Description
The technical solution of the present invention will be clearly and completely described in the following with reference to specific embodiments. It will be understood 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 invention. All other embodiments, such as modifications and substitutions, which can be obtained by one skilled in the art based on the embodiments of the present invention without any inventive step, belong to the protection scope of the present 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 by mass unless otherwise specified.
Example 1
The embodiment provides a method for producing sarcosine, which comprises the following steps:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.8 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water, concentrating to obtain 360g of water, reducing the water content in the solution to 40.6%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein the total amount of the solids is 113g, the residual amount of the sarcosine in the wet salt is 0.31%, filtering to obtain a feed liquid, diluting with the previously concentrated 360g of water, uniformly mixing, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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; controlling the temperature at 30-35 ℃ in the electrodialysis process, adjusting the current to 8A, and stopping operation when the conductance of the material chamber is reduced to 190us/cm to obtain sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 65 ℃ until the water content is 18 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 12 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
The total amount of sarcosine products is 261g, the calculated yield is 85.6%, the HPLC purity is 99.6%, the ignition residue is 0.06%, and the drying weight loss is 0.16%. The prepared sarcosine particles are uniform and do not cake after being packed and placed in vacuum.
Example 2
The embodiment provides a method for producing sarcosine, which comprises the following steps:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 7.0 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 65 ℃, concentrating under negative pressure to remove water to obtain 380g of water, reducing the water content in the solution to 38.7%, then cooling to 25 ℃, separating out solid, filtering out the solid to obtain wet salt, wherein the total amount of the solid is 109g, the residual amount of the sarcosine in the wet salt is 0.29%, filtering to obtain a feed liquid which is a desalted sarcosine solution, diluting with 380g of water concentrated previously, mixing uniformly, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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; controlling the temperature at 30-35 deg.C in electrodialysis process, adjusting current to 6A, and stopping operation when conductivity of material chamber is reduced to 193us/cm to obtain sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 62 ℃ until the water content is 16 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:5), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
The total amount of the sarcosine product is 263g, the calculated yield is 85.7%, the HPLC purity is 99.3%, the ignition residue is 0.08%, and the drying weight loss is 0.15%. The prepared sarcosine particles are uniform and do not cake after being packed and placed in vacuum.
Comparative example 1
The comparative example provides a method for producing sarcosine, comprising the steps of:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.6 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water to obtain 380g of water, reducing the water content in the solution to 38.7%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein 118g of the wet salt is obtained, the residual amount of the sarcosine in the wet salt is 0.33%, filtering to obtain a feed liquid, diluting the feed liquid with 380g of the water obtained by concentration, uniformly mixing, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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; controlling the temperature at 30-35 deg.C in electrodialysis process, adjusting current to 6A, stopping operation when the conductance of material chamber is reduced to 990us/cm to obtain sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 62 ℃ until the water content is 16 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
263g total sarcosine product, calculated yield 80.3%, HPLC purity 93.1%, ignition residue 5.6%, drying weight loss 0.16%.
As can be seen from this comparative example, when the conductivity of the feed chamber decreased to 1000us/cm or less and to 200us/cm or more, the purity of the sarcosine product was impaired, resulting in a decrease in purity.
Comparative example 2
The comparative example provides a method for producing sarcosine, comprising the steps of:
(1) Taking 1000g of 38% sodium sarcosinate aqueous solution in percentage by mass, and adjusting the pH value to 6.7 by using hydrochloric acid to obtain a solution containing sarcosine and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water to obtain 365g of water, wherein the water content of the solution is 40.2%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein the total amount of the solids is 110g, the residual amount of the sarcosine in the wet salt is 0.35%, the filtered feed liquid is a desalted sarcosine solution, diluting the desalted sarcosine solution with 365g of water concentrated previously, mixing uniformly, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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, then starting circulating pumps of the chambers, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; controlling the temperature at 30-35 ℃ in the electrodialysis process, adjusting the current to 5A, and stopping operation when the conductivity of the material chamber is reduced to 196us/cm to obtain sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 62 ℃ until the water content is 25 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
The total amount of sarcosine products is 195g, the calculated yield is 63.6%, the HPLC purity is 99.5%, the ignition residue is 0.06%, and the drying weight loss is 0.16%.
According to the comparative example, when the sarcosine solution is purified, the water content of the concentrated solution obtained by vacuum concentration of the sarcosine solution has a remarkable influence 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 method for producing sarcosine, comprising the steps of:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.7 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water to obtain 365g of water, wherein the water content of the solution is 40.2%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein the total amount of the solids is 110g, the residual amount of the sarcosine in the wet salt is 0.35%, the filtered feed liquid is a desalted sarcosine solution, diluting the desalted sarcosine solution with 365g of water concentrated previously, mixing uniformly, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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; controlling the temperature at 30-35 deg.C in electrodialysis process, adjusting current to 5A, stopping operation when the conductance of material chamber is reduced to 195us/cm to obtain sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 62 ℃ until the water content is 19 percent to obtain a concentrated solution, the concentrated solution is mixed with 1 time of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
275g total sarcosine product, 84.5% calculated yield, 93.6% HPLC purity, 0.26% residue on ignition, 0.16% loss on drying.
As can be seen from this comparative example, when the amount of the ethanol-acetone mixed solution added to the concentrated solution was decreased in the purification of the sarcosine solution, the purity of the sarcosine product was significantly decreased.
Comparative example 4
This comparative example provides a process for the production of sarcosine without concentration desalting comprising the steps of:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.7 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Directly carrying out electrodialysis desalination treatment on a solution containing sarcosine and sodium chloride, putting 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, then 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; controlling the temperature at 30-35 ℃ in the electrodialysis process, adjusting the current to 5A, and stopping operation when the conductivity of the material chamber is reduced to 2000us/cm and is difficult to reduce continuously to obtain sarcosine solution;
(3) The sarcosine solution is firstly concentrated in vacuum at 60 ℃ until the water content is 18 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
The total amount of sarcosine products is 281g, the calculated yield is 84.2%, the HPLC purity is 91.6%, the ignition residue is 2.6%, and the drying weight loss is 0.16%.
As can be seen from this comparative example, when the electrodialysis desalination treatment was directly performed, the purity of the obtained sarcosine product was very low, only 91.6%.
Comparative example 5
The comparative example provides a method for producing sarcosine, comprising the steps of:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.7 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water to obtain 460g of water, wherein the water content in the solution is 29.6%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein the total amount of the solids is 145g, the residual amount of the sarcosine in the wet salt is 16.31%, the filtered feed liquid is a desalted sarcosine solution, diluting with 460g of water concentrated previously, mixing uniformly, and performing electrodialysis secondary desalting treatment;
(3) Placing the feed 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; controlling the temperature at 30-35 deg.C in electrodialysis process, adjusting current to 5A, stopping operation when the conductance of material chamber is reduced to 196us/cm to obtain sarcosine solution;
(4) Firstly, concentrating the sarcosine solution at 62 ℃ in vacuum until the water content is 18% to obtain a concentrated solution, mixing the concentrated solution with 2 times of ethanol-acetone mixed solution (wherein the mass ratio of ethanol to acetone is 1:4), uniformly stirring, cooling to 15 ℃, then carrying out heat preservation and crystallization for 6 hours, separating out a crystalline solid, and drying to obtain the sarcosine product.
The total amount of sarcosine products is 161g, the calculated yield is 52.6%, the HPLC purity is 99.6%, the ignition residue is 0.06%, and the drying weight loss is 0.16%.
It can be seen from this comparative example that the water content after concentration was too low during desalting by concentration, and the residual amount of sarcosine in the wet salt separated by filtration was large, which resulted in a significant decrease in the yield of sarcosine product.
Comparative example 6
The comparative example provides a method for producing sarcosine, comprising the steps of:
(1) Taking 1000g of sodium sarcosinate aqueous solution with the mass percentage concentration of 38%, and adjusting the pH value to 6.7 by using hydrochloric acid to obtain solution containing the sarcosinate and sodium chloride;
(2) Heating a solution containing sarcosine and sodium chloride to 60 ℃, concentrating under negative pressure to remove water to obtain 260g of water, wherein the water content in the solution is 48.6%, then cooling to 28 ℃, separating out solids, filtering out the solids to obtain wet salt, wherein the total amount of the solids is 33g, the residual amount of the sarcosine in the wet salt is 0.06%, the filtered feed liquid is a desalted sarcosine solution, diluting the desalted sarcosine solution with 260g of the water concentrated previously, and carrying out electrodialysis secondary desalting treatment after uniform mixing;
(3) Placing the feed 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, then starting circulating pumps of the chambers, adjusting the flow rate to 30cm/s, starting a power supply of the electrodialysis equipment, and starting electrodialysis treatment; controlling the temperature at 30-35 ℃ in the electrodialysis process, adjusting the current to 5A, hardly continuously reducing the conductance of the material chamber when the conductance of the material chamber is reduced to below 1600us/cm, and stopping the operation to obtain a sarcosine solution;
(4) The sarcosine solution is firstly concentrated in vacuum at 62 ℃ until the water content is 18 percent to obtain a concentrated solution, the concentrated solution is mixed with 2 times of ethanol-acetone mixed solution (wherein, the mass ratio of ethanol to acetone is 1:4), the mixture is uniformly stirred, the temperature is reduced to 15 ℃, the mixture is kept for crystallization for 6 hours, crystalline solids are separated out, and the sarcosine product is obtained after drying.
261g total sarcosine product, calculated yield 79.6%, HPLC purity 92.9%, residue on ignition 1.6%, drying weight loss 0.16%.
According to the comparative example, when the concentration desalting is carried out, the water content is too high after the concentration, the wet salt amount separated by filtration is reduced, and when the electrodialysis desalting is carried out, the desalting effect is poor, so that the purity of the sarcosine product is influenced, and the product purity is reduced.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A method for producing sarcosine, which comprises the steps of:
(1) Adjusting the pH value of the sarcosine sodium aqueous solution to 6.5-7.0 by using hydrochloric acid to obtain a sarcosine-containing salt solution;
(2) Concentrating the salt solution containing the sarcosine for primary desalination to obtain a desalted sarcosine solution;
(3) Performing electrodialysis secondary desalination on the desalted sarcosine solution to obtain a sarcosine solution;
(4) And purifying and crystallizing the sarcosine solution to obtain the sarcosine product.
2. The production process according to claim 1, wherein the concentration of the aqueous solution of sodium sarcosinate is 37 to 40% by mass, preferably 38% by mass.
3. The production method according to claim 1 or 2, wherein the concentration primary desalting comprises: and concentrating the sarcosine-containing salt solution until the water content is 35-45%, cooling to separate out solids, and separating to remove the solids to obtain the desalted sarcosine solution.
4. The production method according to claim 3, wherein the concentration temperature of the sarcosine-containing salt solution is controlled to 60 to 65 ℃; and/or, cooling to 25-30 ℃ to precipitate a solid.
5. The production method according to any one of claims 1 to 4, wherein the electrodialysis secondary desalination comprises: and (3) carrying out electrodialysis treatment on the desalted sarcosine solution, and stopping electrodialysis when the conductivity of a material chamber is reduced to be below 200us/cm to obtain the sarcosine solution.
6. The production method according to claim 5, wherein the temperature during the electrodialysis is controlled to be 20-40 ℃ and the current is 1-10A.
7. The production process according to any one of claims 1 to 6, wherein the desalted sarcosine solution is diluted with water before being subjected to the electrodialysis treatment; preferably, the mass of the added water is 30-40% of the mass of the sodium sarcosinate aqueous solution.
8. The production method according to any one of claims 1 to 7, wherein the sarcosine solution purification comprises: firstly, concentrating the sarcosine solution until the water content is 15-20% to obtain a concentrated solution, mixing the concentrated solution with an ethanol-acetone mixed solution, cooling for crystallization, separating a crystalline solid, and drying to obtain the sarcosine product.
9. The production method according to claim 8, wherein the mass ratio of the ethanol-acetone mixed solution to the concentrated solution is (2-3): 1; and/or the presence of a gas in the gas,
the mass ratio of ethanol to acetone in the ethanol-acetone mixed solution is 1: (4-5); and/or the presence of a gas in the gas,
cooling to 10-15 deg.C, and crystallizing at constant temperature, preferably for 5-7h.
10. Sarcosine product obtainable by the production process according to any one of claims 1 to 9.
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