CN112645992B - Method for recovering glucosamine hydrochloride mother liquor and application thereof - Google Patents
Method for recovering glucosamine hydrochloride mother liquor and application thereof Download PDFInfo
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- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
The invention relates to a method for recovering glucosamine hydrochloride mother liquor and application thereof, wherein the method comprises the following steps: (1) cooling the mother liquor obtained by preparing the glucosamine hydrochloride to be within 3 ℃ above the critical temperature of the glucosamine hydrochloride precipitation to obtain metastable mother liquor; (2) placing a pipe body with an induced crystallization carrier loaded on the surface into metastable mother liquor, then introducing flowing refrigerant into the pipe body, and adding an organic precipitator into the mother liquor; the temperature of the refrigerant is lower than the critical temperature, and the induced crystallization carrier is marble slag; (3) stopping introducing the refrigerant when no glucosamine hydrochloride crystals are separated out on the surface of the tube body, taking out the tube body, and washing the crystals on the surface of the tube body with hot water to obtain a washing liquid; (4) concentrating and crystallizing the washing liquid to obtain the product. The method of the invention not only can effectively recover the glucosamine hydrochloride in the mother liquor, but also does not need a complex refining procedure, so that the recovery of the mother liquor is more efficient.
Description
Technical Field
The invention relates to the technical field of glucosamine preparation, in particular to a method for recovering glucosamine hydrochloride mother liquor and application thereof.
Background
Glucosamine hydrochloride (molecular formula: C)6H13NO5HCl), also known as glucamine hydrochloride, known as 2-aminodeoxyglucose hydrochloride, glucosamineThe hydrochloride is prepared by hydrolyzing chitin or chitosan with hydrochloric acid, is a medicine which can fundamentally treat osteoarticular diseases in medical field, and the glucosamine and the chondroitin sulfate are used together, so that the hydrochloride has the effects of relieving pain and promoting cartilage regeneration, and can fundamentally improve joint problems. Besides, the glucosamine hydrochloride also has the functions of preventing the accumulation of cholesterol in human bodies, protecting health and resisting aging.
Currently, the following methods are commonly used for preparing glucosamine hydrochloride: the method comprises the steps of hydrolyzing chitin serving as a raw material by concentrated hydrochloric acid to obtain glucosamine hydrochloride hydrolysate, refining a crude product, salifying the refined crude product with strong sodium oxide to obtain a glucosamine hydrochloride solution, cooling and crystallizing the solution, separating glucosamine hydrochloride solid, and taking the residual liquid as a mother solution. However, a considerable portion of glucosamine hydrochloride still remains in the mother liquor, which, if not recovered, would result in waste of the product.
Disclosure of Invention
In view of the above problems, the present invention provides a method for recovering glucosamine hydrochloride mother liquor and the application thereof, which can not only effectively recover glucosamine hydrochloride in the mother liquor, but also eliminate the need for complicated refining procedures, thereby making the recovery of the mother liquor more efficient. In order to achieve the purpose, the invention discloses the following technical scheme:
firstly, the invention discloses a method for recovering glucosamine hydrochloride mother liquor, which comprises the following steps:
(1) the mother liquor obtained by preparing the glucosamine hydrochloride is cooled to be higher than or within 3 ℃ of the critical temperature of the glucosamine hydrochloride separation, so that the condition that partial glucosamine hydrochloride is separated out from the mother liquor to influence the recovery is avoided, and the obtained metastable mother liquor is reserved.
(2) Placing a pipe body loaded with an induced crystallization carrier on the surface in the metastable liquid in the step (1), introducing flowing refrigerants into the pipe body, and adding an organic precipitator into the mother liquid; and (3) the temperature of the refrigerant is lower than the critical temperature of the step (1), and the induced crystallization carrier is marble slag.
(3) Stopping introducing the refrigerant when no glucosamine hydrochloride crystals are separated out on the surface of the tube body, taking out the tube body, and washing the crystals on the surface of the tube body with hot water to obtain a washing liquid.
(4) And concentrating and crystallizing the flushing fluid to obtain glucosamine hydrochloride.
Further, in the step (1), the mother liquor obtained by preparing glucosamine hydrochloride is gradually cooled until the glucosamine hydrochloride begins to be separated out, and the mother liquor is used as a critical temperature.
Further, in the step (1), the mother liquor is cooled to the temperature which is 1-3 ℃ above the critical temperature of the glucosamine hydrochloride precipitation.
In step (2), the pipe body may include any one of a straight pipe, a "U" -shaped pipe, a serpentine pipe, and the like, and the material of the pipe body may include any one of stainless steel, aluminum alloy, and the like. The refrigerant enters from one end of the tube body and flows out from the other end, so that the temperature of the tube body is continuously kept below the critical temperature.
Further, in the step (2), the temperature of the refrigerant is not higher than 8 ℃, and the temperature of the tube body can be continuously kept in a state of being lower than the temperature of the mother liquid by continuously passing the low-temperature refrigerant in the tube body, so that the crystallization of the glucosamine hydrochloride on the surface of the tube body is facilitated.
Further, in the step (2), the refrigerant includes any one of cooling water, cold air, and the like.
Further, in the step (2), the organic precipitant includes at least one of ethanol, acetone, and the like. Optionally, the organic precipitant is added in an amount of 0.10-0.35 times the volume of the mother liquor, and mainly functions to increase the concentration of glucosamine hydrochloride and accelerate crystallization thereof.
Further, in the step (2), the temperature of the hot water is 40-65 ℃, so that the crystal on the surface of the tube body can be washed quickly and thoroughly, and the recovery loss is reduced.
Further, in the step (4), the concentration is carried out under vacuum by heating at a temperature of 65 to 85 ℃.
The invention further discloses application of the method for recovering the glucosamine hydrochloride mother liquor in the fields of chemical engineering, medical treatment and the like.
Compared with the prior art, the invention has the following beneficial effects:
(1) the method for inducing the glucosamine hydrochloride to crystallize on the surface of the tube body loaded with the induced crystallization carrier can effectively recover the glucosamine hydrochloride in the mother solution, more importantly, the method can conveniently separate a crystal from the mother solution, and then the crystal is recrystallized after being washed by water. Compared with the traditional method for directly concentrating and crystallizing, the method provided by the invention has the advantages that the purity of the glucosamine hydrochloride is higher; compared with the extraction method adopting various chemical reagents and the like, the method provided by the invention is simpler and more efficient, is low in cost, and generates less chemical waste liquid.
(2) The chemical precipitant is added in the crystallization process of the glucosamine hydrochloride, and the glucosamine hydrochloride is insoluble in organic solvents such as ethanol and the like, so that the crystallization of the glucosamine hydrochloride in the mother liquor in an induced crystallization carrier can be promoted, and meanwhile, the chemical precipitant can be recycled and reused.
(3) The mother liquor is cooled to a metastable state slightly higher than the critical temperature of glucosamine hydrochloride precipitation, and then the temperature in the mother liquor on the surface of the tube body is quickly reduced to be below the critical temperature through the tube body loaded with the crystallization inducing carrier and the low-temperature refrigerant, and under the heterogeneous nucleation effect brought by the rough crystallization inducing carrier formed by marble slag, the glucosamine hydrochloride in the mother liquor quickly forms crystal nuclei on the crystallization inducing carrier, and the crystal nuclei also provide sites for the crystallization of the glucosamine hydrochloride. Meanwhile, the low-temperature refrigerant can enable the tube body and the mother liquor to continuously form a temperature gradient, so that the glucosamine hydrochloride has the power of continuously crystallizing on the surface of the induced crystallization carrier, and the recovery rate of the mother liquor is improved.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. The invention will now be further illustrated by means of specific embodiments.
Example 1
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as a critical temperature, and then heating the mother liquor to be more than 3 ℃ of the critical temperature to obtain the metastable mother liquor.
(2) And (2) placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the metastable mother liquor obtained in the step (1), introducing cooling water (the temperature is 5 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.3 times that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) After 4 hours, basically no glucosamine hydrochloride crystals are separated out on the surface of the coiled pipe, stopping introducing cooling water into the coiled pipe, taking out the coiled pipe, and washing the crystals on the surface of the pipe body with hot water at 60 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
Example 2
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as a critical temperature, and then heating the mother liquor to be more than 3 ℃ of the critical temperature to obtain the metastable mother liquor.
(2) And (2) placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the metastable mother liquor obtained in the step (1), introducing cooling water (the temperature is 8 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.2 times that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) After 4.5 hours, basically no glucosamine hydrochloride crystals are separated out on the surface of the coiled pipe, the cooling water is stopped to be introduced into the coiled pipe, then the coiled pipe is taken out, and the crystals on the surface of the pipe body are washed off by hot water at 65 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at 85 ℃ to obtain glucosamine hydrochloride.
Example 3
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as critical temperature, and then heating the mother liquor to the temperature 2 ℃ above the critical temperature to obtain metastable mother liquor.
(2) Placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the metastable mother liquor obtained in the step (1), introducing cooling water (the temperature is 6 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding acetone with the volume 0.35 times of that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) And after crystallizing for 3.5 hours, observing that the surface of the coiled pipe is basically not separated out by the glucosamine hydrochloride crystal, stopping introducing cooling water into the coiled pipe, taking out the coiled pipe, and washing the crystal on the surface of the pipe body by hot water at 55 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
(5) And (4) carrying out reduced pressure distillation on the mother liquor from which the coiled pipe is taken out in the step (3) at 45 ℃ to recover the precipitant in the mother liquor.
Example 4
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as a critical temperature, and then heating the mother liquor to the temperature 1 ℃ above the critical temperature to obtain the metastable mother liquor.
(2) And (2) placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the metastable mother liquor obtained in the step (1), introducing cooling water (the temperature is 8 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.10 times that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) After 4.5 hours of crystallization, basically no glucosamine hydrochloride crystals are observed to be separated out on the surface of the coiled pipe, cooling water is stopped to be introduced into the coiled pipe, then the coiled pipe is taken out, the crystals on the surface of the pipe body are washed by hot water at 40 ℃, the pipe body is washed for three times, and the washing liquids are mixed for standby.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at 65 ℃ to obtain glucosamine hydrochloride.
(5) And (4) carrying out reduced pressure distillation on the mother liquor from which the coiled pipe is taken out in the step (3) at 45 ℃ to recover the precipitant in the mother liquor.
Test example 1
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) placing a stainless steel coil pipe with marble slag loaded on the surface into mother liquor obtained by preparing glucosamine hydrochloride, introducing cooling water (the temperature is 5 ℃) into one end of the coil pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.3 times of that of the mother liquor into the mother liquor to serve as a precipitator, so that the glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coil pipe.
(2) And stopping introducing cooling water into the coiled pipe after 4 hours, taking out the coiled pipe, and washing crystals on the surface of the pipe body with hot water at 60 ℃ to obtain a washing liquid.
(3) And (3) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (2) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
Test example 2
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as a critical temperature, and then heating the mother liquor to be more than 3 ℃ of the critical temperature to obtain the metastable mother liquor.
(2) And (2) placing a stainless steel coiled pipe in the mother liquor cooled in the step (1), introducing cooling water (the temperature is 5 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.3 times that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of marble slag on the surface of the coiled pipe.
(3) And stopping introducing cooling water into the coiled pipe after 4 hours, taking out the coiled pipe, and washing crystals on the surface of the pipe body with hot water at 60 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
Test example 3
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, stopping cooling, recording the temperature at the moment as a critical temperature, and then heating the mother liquor to be more than 3 ℃ of the critical temperature to obtain the metastable mother liquor.
(2) And (2) placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the metastable mother liquor in the step (1), then introducing cooling water (the temperature is 5 ℃) into one end of the coiled pipe, and enabling the cooling water to flow out from the other end, so that glucosamine hydrochloride in the mother liquor is crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) And stopping introducing cooling water into the coiled pipe after 4 hours, taking out the coiled pipe, and washing crystals on the surface of the pipe body with hot water at 60 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
Test example 4
A method for recovering glucosamine hydrochloride mother liquor comprises the following steps:
(1) gradually cooling the mother liquor obtained by preparing the glucosamine hydrochloride until the glucosamine hydrochloride is separated out, continuing to reduce the temperature by 3 ℃, and stopping cooling to obtain the cooled mother liquor.
(2) And (2) placing a coiled pipe made of stainless steel and loaded with marble slag on the surface into the cooling mother liquor obtained in the step (1), introducing cooling water (the temperature is 5 ℃) into one end of the coiled pipe, enabling the cooling water to flow out from the other end, and adding ethanol with the volume 0.3 times that of the mother liquor into the mother liquor to serve as a precipitator, so that glucosamine hydrochloride in the mother liquor is gradually crystallized on the surface of the marble slag on the surface of the coiled pipe.
(3) And stopping introducing cooling water into the coiled pipe after 4 hours, taking out the coiled pipe, and washing crystals on the surface of the pipe body with hot water at 60 ℃ to obtain a washing liquid.
(4) And (4) carrying out vacuum concentration and crystallization on the flushing liquid obtained in the step (3) at the temperature of 70 ℃ to obtain glucosamine hydrochloride.
The results of the measurement of the recovery rates of glucosamine hydrochloride in the mother liquor of examples 1-4 and experimental examples 1-4 are respectively shown in table 1 and table 2, and it can be seen from the tables that the recovery rates of glucosamine hydrochloride in the mother liquor by the methods in the examples are obviously better than those of the experimental examples, and the method of the present invention significantly improves the recovery rate of the mother liquor compared with the conventional method of direct concentration for crystallization (the recovery rate is generally below 65).
TABLE 1
| Number of implementation | Example 1 | Example 2 | Example 3 | Example 4 |
| Glucosamine hydrochloride recovery% | 95.6 | 92.8 | 94.1 | 94.4 |
TABLE 2
| Number of implementation | Test example 1 | Test example 2 | Test example 3 | Test example 4 |
| Glucosamine hydrochloride recovery% | 83.5 | 47.9 | 78.3 | 74.7 |
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (6)
1. A method for recovering glucosamine hydrochloride mother liquor is characterized by comprising the following steps:
(1) cooling the mother liquor obtained by preparing the glucosamine hydrochloride to the temperature 1-3 ℃ above the critical temperature of the glucosamine hydrochloride precipitation to obtain metastable mother liquor for later use;
(2) placing a pipe body with an induced crystallization carrier loaded on the surface into the metastable mother liquor, then introducing flowing refrigerants into the pipe body, and adding an organic precipitator into the mother liquor; the temperature of the refrigerant is lower than the critical temperature of the step (1), and the induced crystallization carrier is marble slag; the pipe body is made of stainless steel; the temperature of the refrigerant is not higher than 8 ℃, and the refrigerant is cooling water; the organic precipitator is selected from ethanol or acetone;
(3) stopping introducing the refrigerant when no glucosamine hydrochloride crystals are separated out on the surface of the tube body, taking out the tube body, and washing the crystals on the surface of the tube body with hot water to obtain a washing liquid;
(4) and concentrating and crystallizing the flushing fluid to obtain glucosamine hydrochloride.
2. The method according to claim 1, wherein the mother liquor obtained by the preparation of glucosamine hydrochloride in step (1) is gradually cooled to a critical temperature at which glucosamine hydrochloride begins to be precipitated.
3. The method for recovering glucosamine hydrochloride mother liquor according to claim 1, wherein in the step (2), the tube body is any one of a straight tube, a "U" -shaped tube and a coiled tube.
4. The method for recovering glucosamine hydrochloride mother liquor according to claim 1, wherein the amount of the organic precipitant added is 0.1-0.35 times the volume of the mother liquor.
5. The method for recovering glucosamine hydrochloride mother liquor according to any one of claims 1-4, wherein the temperature of the hot water in the step (3) is 40-65 ℃; or, in the step (4), heating concentration is carried out under vacuum condition, and the heating temperature is 65-85 ℃.
6. The use of the method for recovering glucosamine hydrochloride stock solution according to any one of claims 1-5 in the fields of chemical industry and medicine.
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| CN103694280A (en) * | 2013-11-29 | 2014-04-02 | 安徽丰原发酵技术工程研究有限公司 | Method for extracting glucosamine hydrochloride from glucosamine hydrochloride-containing mother liquor |
| CN110256506A (en) * | 2019-07-19 | 2019-09-20 | 山东润德生物科技有限公司 | A method of preparing aminoglucose hydrochloride |
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| WO2007135086A1 (en) * | 2006-05-19 | 2007-11-29 | Inalco S.P.A. | Process for the preparation of n-acetyl-d-mannosamine monohydrate |
| CN102391322A (en) * | 2011-12-15 | 2012-03-28 | 石狮市华宝海洋生物化工有限公司 | Method for recovering glucosamine hydrochloride from hydrolytic mother liquid of glucosamine hydrochloride |
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Effective date of registration: 20220831 Address after: 271000 No. 78, Runde Road, Xintai Development Zone, Tai'an City, Shandong Province Patentee after: SHANDONG RUNDE BIOTECHNOLOGY Co.,Ltd. Address before: 271000 No. 78, Runde Road, Xintai Development Zone, Tai'an City, Shandong Province Patentee before: SHANDONG RUNDE BIOTECHNOLOGY Co.,Ltd. Patentee before: Deyuantang (Shanghai) Health Technology Development Co.,Ltd. |