CN110713446B - Method for separating dimethyl sulfoxide from amlodipine resolution waste liquid - Google Patents
Method for separating dimethyl sulfoxide from amlodipine resolution waste liquid Download PDFInfo
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- CN110713446B CN110713446B CN201911227830.7A CN201911227830A CN110713446B CN 110713446 B CN110713446 B CN 110713446B CN 201911227830 A CN201911227830 A CN 201911227830A CN 110713446 B CN110713446 B CN 110713446B
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/06—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention relates to the technical field of solvent separation and recovery, and particularly discloses a method for separating dimethyl sulfoxide from amlodipine resolution waste liquid, which comprises the following steps: carrying out nanofiltration on the amlodipine split waste liquid by using a polyimide nanofiltration membrane to obtain nanofiltration clear liquid, namely the recovered dimethyl sulfoxide; the swelling ratio of the polyimide nanofiltration membrane in dimethyl sulfoxide is 1.4-1.6, and the interception precision is 180-200 Da. The recovery method is simple, greatly reduces the recovery cost of the dimethyl sulfoxide, and obviously improves the recovery rate and the purity of the dimethyl sulfoxide.
Description
Technical Field
The invention relates to the technical field of separation and recovery of solvents, in particular to a method for separating dimethyl sulfoxide from amlodipine resolution waste liquid.
Background
Amlodipine belongs to a third-generation long-acting calcium ion antagonist and is a common medicine for treating hypertension and angina. Amlodipine is taken as a chiral drug, wherein, levoamlodipine and dextroamlodipine respectively account for 50 percent, while the levoamlodipine has the function of reducing blood pressure, dextroamlodipine has almost no function of reducing blood pressure, the half-life period of the levoamlodipine is obviously higher than that of dextroisomer, and the dextroamlodipine in the drug can improve the incidence rate of adverse reaction, so dimethyl sulfoxide (DMSO) and tartaric acid are generally used as a resolution liquid to resolve racemic amlodipine in the production process of amlodipine drugs, wherein, the levoamlodipine can be combined with the tartaric acid in the resolution liquid to form a precipitate, the dextroamlodipine is dissolved in the dimethyl sulfoxide solution, the precipitate formed in the resolution process is separated out and further processed to obtain the levoamlodipine, the residual liquid is generally used as dangerous waste to be processed, and the levoamlodipine and the dextroamlodipine and the tartaric acid contain a large amount of DMSO and the dextroamlodipine and a small amount of tartaric acid, the dangerous waste treatment cost is about 1 ten thousand yuan/ton, the market purchase price of DMSO is about 1.2 ten thousand yuan/ton, which is equivalent to the cost of twice DMSO (dimethyl sulfoxide) in the process of producing levamlodipine, in order to further reduce the production cost and improve the market competitiveness of products, the recovery of DMSO in the split mother liquor is an urgent problem to be solved by amlodipine production enterprises, but the existing DMSO recovery method adopts a distillation mode mostly, the recovery method is complex, the recovery rate is low and the cost is high, the purpose of reducing the cost cannot be achieved, and dimethyl sulfoxide is a universal solvent, has solubility on various polymers, and has certain dissolution destructive capacity on nanofiltration membranes, so that the DMSO is difficult to be separated by a filtration separation method.
Disclosure of Invention
Aiming at the problems of complex method, high recovery cost and low recovery efficiency of the existing method for separating dimethyl sulfoxide from the amlodipine resolution waste liquid, the invention provides a method for separating dimethyl sulfoxide from the amlodipine resolution waste liquid.
In order to achieve the purpose of the invention, the embodiment of the invention adopts the following technical scheme:
a method for separating dimethyl sulfoxide from amlodipine resolution waste liquid comprises the following steps: carrying out nanofiltration on the amlodipine split waste liquid by using a polyimide nanofiltration membrane to obtain nanofiltration clear liquid, namely the recovered dimethyl sulfoxide;
the swelling ratio of the polyimide nanofiltration membrane in dimethyl sulfoxide is 1.4-1.6, and the interception precision is 180-200 Da.
Compared with the prior art, the method for separating dimethyl sulfoxide from amlodipine split waste liquid provided by the invention separates the dimethyl sulfoxide by a nanofiltration method, wherein the used nanofiltration membrane is a polyimide nanofiltration membrane, the nanofiltration membrane has higher tolerance to the dimethyl sulfoxide, and when the used polyimide nanofiltration membrane has a swelling ratio of 1.4-1.6 in the dimethyl sulfoxide and a retention precision of 180-200Da, the swelling effect generated in the nanofiltration process of the amlodipine split waste liquid can increase the distance between network chains in the polyimide nanofiltration membrane to the extent that the dimethyl sulfoxide can smoothly pass through the polyimide nanofiltration membrane without blocking a nanofiltration channel of the nanofiltration membrane, effectively prevents dextroamlodipine and tartaric acid in the amlodipine split waste liquid from passing through the nanofiltration membrane, and enables the purity of the dimethyl sulfoxide recovered by nanofiltration to reach more than 99 percent, the quality of the dimethyl sulfoxide obtained by recovery reaches more than 95% of the total amount of the dimethyl sulfoxide in the amlodipine resolution waste liquid, the recovery method can be carried out at normal temperature, no extra energy consumption is needed, the recovery method is simple, the recovery cost of the dimethyl sulfoxide is greatly reduced, the resource waste is reduced, and the environmental pressure is relieved.
Preferably, the membrane feeding pressure in the nanofiltration process is 1.5-4.0 MPa.
When the membrane feeding pressure is 1.5-4.0MPa, the high nanofiltration speed of the dimethyl sulfoxide can be ensured, and the polyimide nanofiltration membrane can not be blocked.
Preferably, the membrane feeding pressure in the nanofiltration process is 1.8-2.0 MPa.
Preferably, the nanofiltration temperature is 20-40 ℃.
Preferably, the nanofiltration flux is less than or equal to 10L/h.m in the nanofiltration process2And stopping the nanofiltration process.
When the nanofiltration flux is less than or equal to 10L/h.m in the nanofiltration process2In the process, if the nanofiltration is continued, the transmittance of tartaric acid and dextro-amlodipine is increased, the purity of the recovered dimethyl sulfoxide is influenced, the recovery cost is increased, and the industrial value is not high.
Preferably, the method also comprises the step of carrying out reduced pressure distillation on the concentrated solution obtained by nanofiltration, and mixing the obtained distillate with the nanofiltration clear solution to obtain the recovered dimethyl sulfoxide.
And (3) carrying out reduced pressure distillation treatment on the concentrated solution obtained by nanofiltration, wherein the content of dimethyl sulfoxide is low, and the dimethyl sulfoxide can be quickly and completely separated out through simple reduced pressure distillation treatment, so that the total recovery rate of the dimethyl sulfoxide reaches more than 99%.
Preferably, the temperature of the reduced pressure distillation is 105-125 ℃.
Preferably, the pressure of the reduced pressure distillation is 0.2-0.5 MPa.
Drawings
FIG. 1 is a schematic view of the structure of an apparatus used in the recovery process of DMSO in example 1 of the present invention;
the device comprises a separation device 1, a crystallizing tank 2, a centrifuge 4, a nanofiltration device 5 and a rectifying tower.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
The following examples are provided to better illustrate the embodiments of the present invention.
Example 1
The device for separating dimethyl sulfoxide from amlodipine splitting waste liquid is shown in figure 1, and comprises a splitting and separating device 1, a crystallizing tank 2, a centrifuge 3, a nanofiltration device 4 and a rectifying tower 5 which are connected in sequence; wherein, the nanofiltration device 4 is internally provided with a polyimide nanofiltration membrane component, and the liquid outlets of the nanofiltration device 4 and the rectifying tower 5 are communicated with the liquid inlet of the splitting and separating device 1.
The method for separating dimethyl sulfoxide from amlodipine split waste liquid by using the device comprises the following specific processes:
in the production process of the levamlodipine, taking DMSO and tartaric acid as splitting liquid for splitting, splitting and centrifugally separating in a splitting and separating device 1 to obtain a mother liquid of the levamlodipine, sending the mother liquid into a crystallizing tank 2 for cooling crystallization, controlling the cooling rate to be 4 ℃/h, controlling the crystallization temperature to be 12 ℃, keeping the temperature for 30min, putting the mother liquid into a centrifugal machine 3, centrifugally separating at 12 ℃ to obtain a crystal of the levamlodipine and an amlodipine splitting waste liquid, and detecting that the mass concentration of the levamlodipine in the splitting waste liquid is 5.5%, the mass concentration of the tartaric acid is 1.19% and the mass concentration of the DMSO is 93.31%;
the split waste liquid is sent into a nanofiltration device 4 provided with a polyimide nanofiltration membraneWherein the swelling ratio of the polyimide nanofiltration membrane in dimethyl sulfoxide is 1.4, the membrane inlet temperature is controlled to be 20 ℃, the membrane inlet pressure is controlled to be 1.8MPa, and the nanofiltration flux is reduced to 10L/h.m in the nanofiltration process2And stopping the nanofiltration separation process, and collecting clear liquid and concentrated liquid.
Wherein the mass fractions of DMSO in the clear liquid obtained by nanofiltration are respectively 99.2%, and the rest is tartaric acid.
And (3) feeding the concentrated solution obtained by nanofiltration into a rectifying tower 5 for reduced pressure distillation, controlling the temperature to be 105 ℃ and the pressure to be 0.2MPa, condensing and cooling the DMSO gas extracted from the tower top, collecting liquid DMSO, wherein the purity of the collected liquid DMSO is 99.7%, and the residual tartaric acid and the dextroamlodipine are in the tower kettle.
And (3) combining the clear liquid obtained by nanofiltration with the liquid DMSO obtained by reduced pressure distillation collection to obtain the recovered DMSO, wherein the total recovery rate of the DMSO is up to 99% and the purity of the DMSO is 99.22% through detection.
Wherein the recovery rate of DMSO is the percentage of the content of DMSO in the recovered product in the content of DMSO in the amlodipine resolution waste liquid.
The recovered DMSO can be re-introduced into the separation device 1 as a separation liquid for recycling.
Example 2
The method for separating dimethyl sulfoxide from amlodipine split waste liquid by using the device for separating dimethyl sulfoxide in embodiment 1 comprises the following specific processes:
in the production process of the levamlodipine, taking DMSO and tartaric acid as splitting liquid for splitting, splitting and centrifugally separating in a splitting and separating device 1 to obtain a mother liquid of the levamlodipine, sending the mother liquid into a crystallizing tank 2 for cooling crystallization, controlling the cooling rate to be 4 ℃/h, controlling the crystallization temperature to be 12 ℃, keeping the temperature for 30min, putting the mother liquid into a centrifugal machine 3, centrifugally separating at 12 ℃ to obtain levamlodipine crystals and an amlodipine splitting waste liquid, and detecting that the mass concentration of the levamlodipine in the splitting waste liquid is 6%, the mass concentration of the tartaric acid is 1.3% and the mass concentration of the DMSO is 92.7%;
feeding the split waste liquid into a nanofiltration device 4 provided with a polyimide nanofiltration membrane, wherein the polyimide nanofiltration membrane is in dimethyl sulfoxideThe swelling ratio is 1.5, the membrane feeding temperature is controlled to be 30 ℃, the membrane feeding pressure is 1.9MPa, and the nanofiltration flux is reduced to 10L/h.m in the nanofiltration process2And stopping the nanofiltration separation process, and collecting clear liquid and concentrated liquid.
Wherein the mass fraction of DMSO in the clear liquid obtained by nanofiltration is 99.3 percent respectively.
And (3) feeding the concentrated solution obtained by nanofiltration into a rectifying tower 5 for reduced pressure distillation, controlling the temperature at 120 ℃ and the pressure at 0.3MPa, condensing and cooling the DMSO gas extracted from the tower top, collecting liquid DMSO, wherein the purity of the collected liquid DMSO is 99.8%, and the residual tartaric acid and the dextroamlodipine are in the tower kettle.
And (3) combining clear liquid obtained by nanofiltration with liquid DMSO obtained by reduced pressure distillation and collection to obtain recovered DMSO, wherein the total recovery rate of the DMSO is up to 99.15% and the purity of the DMSO is up to 99.31% through detection.
The apparatus used in the specific recovery process described above was the same as in example 1.
Example 3
The method for separating dimethyl sulfoxide from amlodipine split waste liquid by using the device for separating dimethyl sulfoxide in embodiment 1 comprises the following specific processes:
in the production process of the levamlodipine, taking DMSO and tartaric acid as splitting liquid for splitting, splitting and centrifugally separating in a splitting and separating device 1 to obtain a mother liquid of the levamlodipine, sending the mother liquid into a crystallizing tank 2 for cooling crystallization, controlling the cooling rate to be 4 ℃/h, controlling the crystallization temperature to be 12 ℃, keeping the temperature for 30min, putting the mother liquid into a centrifugal machine 3, centrifugally separating at 12 ℃ to obtain a crystal of the levamlodipine and an amlodipine splitting waste liquid, and detecting that the mass concentration of the levamlodipine in the splitting waste liquid is 5.5%, the mass concentration of the tartaric acid is 1.5% and the mass concentration of the DMSO is 93%;
feeding the split waste liquid into a nanofiltration device 4 provided with a polyimide nanofiltration membrane, wherein the swelling ratio of the polyimide nanofiltration membrane in dimethyl sulfoxide is 1.6, the membrane inlet temperature is controlled to be 40 ℃, the membrane inlet pressure is 2MPa, and the nanofiltration flux is reduced to 10L/h.m in the nanofiltration process2And stopping the nanofiltration separation process, and collecting clear liquid and concentrated liquid.
Wherein the mass fraction of DMSO in the clear liquid obtained by nanofiltration is 99.33 percent respectively.
And (3) feeding the concentrated solution obtained by nanofiltration into a rectifying tower 5 for reduced pressure distillation, controlling the temperature to be 125 ℃ and the pressure to be 0.5MPa, condensing and cooling the DMSO gas extracted from the tower top, collecting liquid DMSO, wherein the purity of the collected liquid DMSO is 99.75%, and the residual tartaric acid and the dextroamlodipine are in the tower kettle.
And (3) combining the clear liquid obtained by nanofiltration with the liquid DMSO obtained by reduced pressure distillation and collection to obtain the recovered DMSO, wherein the total recovery rate of the DMSO is 99.1% and the purity of the DMSO is 99.35% through detection.
The apparatus used in the specific recovery process described above was the same as in example 1.
Comparative example 1
And (3) replacing the nanofiltration membrane in the example 1 with a polyimide nanofiltration membrane with the swelling ratio of 2.0 in dimethyl sulfoxide for nanofiltration, wherein other conditions and methods are the same as those in the example 1, and dimethyl sulfoxide is obtained by recovery, the total recovery rate of DMSO is 95.2% through detection, and the purity is 88.3%.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents or improvements made within the spirit and principle of the present invention should be included in the scope of the present invention.
Claims (8)
1. A method for separating dimethyl sulfoxide from amlodipine resolution waste liquid is characterized in that: carrying out nanofiltration on the amlodipine split waste liquid by using a polyimide nanofiltration membrane to obtain nanofiltration clear liquid, namely the recovered dimethyl sulfoxide; in the amlodipine resolution waste liquid, the mass concentration of the dextroamlodipine is 5.5-6%, the mass concentration of the tartaric acid is 1.19-1.5%, and the mass concentration of the DMSO is 92.7-93.31%;
the swelling ratio of the polyimide nanofiltration membrane in dimethyl sulfoxide is 1.4-1.6, and the interception precision is 180-200 Da.
2. The method of claim 1, wherein: the membrane feeding pressure in the nanofiltration process is 1.5-4.0 MPa.
3. The method of claim 2, wherein: the membrane feeding pressure in the nanofiltration process is 1.8-2.0 MPa.
4. The method of claim 1, wherein: the nanofiltration temperature is 20-40 ℃.
5. The method of claim 1, wherein: when the nanofiltration flux is less than or equal to 10L/h.m in the nanofiltration process2And stopping the nanofiltration process.
6. The method of claim 1, wherein: and carrying out reduced pressure distillation on the concentrated solution obtained by nanofiltration, and mixing the obtained distillate with the nanofiltration clear solution to obtain the recovered dimethyl sulfoxide.
7. The method of claim 6, wherein: the temperature of the reduced pressure distillation is 105-125 ℃.
8. The method of claim 6, wherein: the pressure of the reduced pressure distillation is 0.2-0.5 MPa.
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