CN111592453A - Method for removing/recovering organic solvent in long-chain dicarboxylic acid - Google Patents
Method for removing/recovering organic solvent in long-chain dicarboxylic acid Download PDFInfo
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- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
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- C07C55/18—Azelaic acid
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- C07C55/02—Dicarboxylic acids
- C07C55/21—Dicarboxylic acids containing twelve carbon atoms
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- F26B—DRYING SOLID MATERIALS OR OBJECTS BY REMOVING LIQUID THEREFROM
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Abstract
The invention discloses a method for removing/recovering an organic solvent in a long-chain dicarboxylic acid crude product, which comprises the following steps: and (3) drying the long-chain dicarboxylic acid mixture to be treated by a vacuum blade dryer, and removing the organic solvent. The method can effectively recover the organic solvent on the basis of ensuring the purity and the extraction rate of the long-chain dibasic acid, and can not cause abnormal use of a machine due to the wall bonding phenomenon of the long-chain dibasic acid.
Description
Technical Field
The invention relates to a method for extracting and purifying long-chain dicarboxylic acid, in particular to a method for removing/recovering residual organic solvent in the process of extracting and purifying long-chain dicarboxylic acid by a vacuum paddle dryer.
Background
Long carbon chain dicarboxylic acids (Long chain dicarboxylic acids) refer to aliphatic dicarboxylic acids (DCn) with more than 10 carbon atoms in the carbon chain, have important industrial application, and can be widely used for synthesizing high-grade spices, high-performance engineering plastics, high-temperature dielectrics, high-grade hot melt adhesives, cold-resistant plasticizers, high-grade lubricating oil, high-grade paints, coatings and the like in the chemical industry.
The production of long carbon chain dibasic acid by a biological fermentation method is a microbial fermentation technology which is started in the seventies, takes petroleum byproduct wax oil as a raw material, has wide raw material source, simple production process and mild production conditions, and is widely concerned at home and abroad. The biological method can provide a series of long carbon chain diacid monomers with more than ten carbons, and the novel long carbon chain diacid monomers can compete with the existing long carbon chain diacid market of the chemical synthesis method with more excellent performance. Meanwhile, a series of new functional materials with different properties can be derived from the long carbon chain diacid monomers with different carbon chains.
In the preparation of the long-chain dicarboxylic acid, a series of treatments are generally performed on a fermentation broth obtained by a biological fermentation method to obtain a long-chain dicarboxylic acid product. The method for refining the tridecanedioic acid (beautiful silk, gayan silk, king Chonghui, fine and special chemicals, 2002, 20 (10): 13-14) is divided into a water phase method, an esterification method and a solvent method. Solvent processes in a broad sense include extraction and crystallization processes. The solvent method for processing the long-chain dibasic acid has residual solvent on crystals, and the existence of the impurities can bring adverse effects to the application of the long-chain dibasic acid, particularly can block the polymerization reaction when producing polymers, and reduce the molecular weight of the polymers, so that a great deal of research in the prior art focuses on improving the extraction rate and the conversion purity. CN102617320A discloses a method for treating a reaction solution containing a long-chain dibasic acid salt, which comprises acidifying the reaction solution to convert the long-chain dibasic acid salt into a long-chain dibasic acid, adding an extraction agent to extract the generated long-chain dibasic acid, separating a phase rich in the long-chain dibasic acid, and further separating the long-chain dibasic acid. CN1570124A discloses a method for preparing long-chain dibasic acid by a solvent method, which comprises the steps of sterilizing a long-chain dibasic acid fermentation liquid obtained by fermentation production, adding activated carbon for decolorization, acidifying to separate out dibasic acid to obtain a crude product, adding an organic solvent for dissolution, cooling, crystallizing, separating, washing and drying to obtain a finished product. The above methods are all pursuing extraction rate and conversion purity, and do not consider the recovery and reuse of the solvent, thus inevitably causing resource waste and environmental pollution.
Disclosure of Invention
The invention provides a novel method for extracting and purifying a crude long-chain dibasic acid product, in particular to a method for removing/recovering an organic solvent in the crude long-chain dibasic acid product, aiming at solving the problems that the solvent used in a solvent method is difficult to effectively recover, so that the environment is polluted and the like in the extraction and refining process of producing the long-chain dibasic acid by a biological fermentation method. The method can effectively recover the organic solvent on the basis of ensuring the purity and the extraction rate of the long-chain dibasic acid, and can not cause abnormal use of a machine due to the wall bonding phenomenon of the long-chain dibasic acid.
One of the purposes of the invention is to apply the paddle dryer to the removal or recovery of the organic solvent in the process of extracting and purifying the long-chain dibasic acid.
In a preferred embodiment of the present invention, the paddle dryer is preferably a vacuum paddle dryer.
The second purpose of the invention is a method for removing the organic solvent in the long-chain binary acid mixture; the method comprises the following steps: drying the long-chain dicarboxylic acid mixture to be treated by a vacuum paddle dryer, and removing the organic solvent; controlling the vacuum degree of the vacuum paddle dryer to be-0.02 to-0.1 MPa, and controlling the drying temperature of the vacuum paddle dryer to be 45-125 ℃.
The invention relates to a method for recovering an organic solvent by using a vacuum blade dryer. The inventor discovers that when researching the technology: in the operation process of the vacuum paddle dryer, caking is easily formed to influence the operation of the dryer. Through intensive research, the reasons for this may be: the temperature is increased to cause the dissolution of the long-chain dibasic acid in the organic solvent, and the long-chain dibasic acid is rapidly separated out along with the reduction of the solvent, so that the long-chain dibasic acid is bonded with the particles to form blocks. On one hand, the agglomeration influences the operation of the vacuum paddle dryer, and on the other hand, the long-chain binary acid is dissolved and then separated out, and has certain influence on the particle form of the product.
In a preferred embodiment of the present invention, the long-chain dicarboxylic acid mixture comprises a long-chain dicarboxylic acid and an organic solvent.
In a preferred embodiment of the present invention, the long-chain dicarboxylic acid comprises: one or more of azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, and 9-ene octadecanedioic acid.
In a preferred embodiment of the present invention, the organic solvent includes: one or more of alcohols, acids, ketones, and esters. Wherein the alcohol comprises one or more of methanol, ethanol, isopropanol, and n-butanol. The acid comprises acetic acid. The ketone comprises acetone. The esters include ethyl acetate and/or butyl acetate.
In a preferred embodiment of the present invention, the vacuum degree of the vacuum paddle dryer is controlled to be-0.02 to-0.08 MPa, preferably-0.04 to-0.06 MPa, for example, in the present invention, the vacuum degree may be: -0.03MPa, -0.035MPa, -0.04MPa, -0.045MPa, -0.05MPa, -0.055MPa, -0.06MPa, -0.065MPa, -0.07MPa, -0.075MPa, etc.
According to a preferable technical scheme of the invention, the drying temperature of the vacuum paddle dryer is controlled to be 75-125 ℃, and is preferably 80-115 ℃.
The invention also aims to provide a method for extracting and refining the long-chain dibasic acid, which comprises the following steps:
obtaining a long-chain dicarboxylic acid crude product from fermentation liquor, dissolving the long-chain dicarboxylic acid crude product in an organic solvent, crystallizing to obtain a long-chain dicarboxylic acid crystallization product, drying the long-chain dicarboxylic acid crystallization product by a vacuum paddle dryer, and removing the organic solvent to obtain the long-chain dicarboxylic acid product.
The method for obtaining the crude product of the long-chain dicarboxylic acid from the fermentation liquor is not limited. As a preferred technical scheme, the fermentation liquor containing the long-chain dicarboxylic acid is acidified to obtain a crude product of the long-chain dicarboxylic acid. As another preferred technical scheme, acidifying fermentation liquor containing long-chain dibasic acid, and separating crude long-chain dibasic acid and impurities to obtain crude long-chain dibasic acid; the impurities include bacteria and/or proteins. As another preferable technical scheme, adding alkali into the fermentation liquor containing the long-chain dicarboxylic acid to adjust the pH value to 7-11, heating to 60-100 ℃, carrying out solid-liquid separation, and then acidifying to obtain the crude long-chain dicarboxylic acid.
In a preferred embodiment of the present invention, the pH of the acidification is preferably 2.5 to 5, more preferably 3 to 4, and may be 2.5, 2.6, 2.7, 2.8, 2.9, 3.0, 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9, 4.0, 4.1, 4.2, 4.3, 4.4, 4.5, 4.6, 4.7, 4.8, 4.9, 5.0.
In a preferred embodiment of the present invention, the acidification is carried out by using sulfuric acid and/or hydrochloric acid.
According to a preferable technical scheme of the invention, the crude long-chain dicarboxylic acid product can also contain impurities such as thalli, protein and the like besides the long-chain dicarboxylic acid.
According to a preferable technical scheme, after the long-chain dicarboxylic acid crude product is dissolved in an organic solvent, the solid-liquid separation is carried out to obtain clear liquid, and the clear liquid is recrystallized to obtain a long-chain dicarboxylic acid crystallization product. The separation method is centrifugation or filtration. The purpose of the solid-liquid separation is to remove some of the impurities that are insoluble in the organic solvent.
According to a preferable technical scheme, the long-chain dicarboxylic acid crude product is dissolved in an organic solvent, decolorized and recrystallized to obtain a long-chain dicarboxylic acid crystallization product. The decoloring method can be activated carbon decoloring. The adding amount of the activated carbon is not more than 5% of the volume of the clear liquid. The decoloring temperature is 85-100 ℃. The decoloring time is 15-165 min.
In a preferred embodiment of the present invention, the crystallization is a temperature-decreasing crystallization. The cooling crystallization comprises the following steps: cooling to 65-80 ℃, keeping the temperature for 1-2 hours, then cooling to 25-35 ℃, and crystallizing.
According to a preferable technical scheme of the invention, after the organic solvent is removed, the long-chain dicarboxylic acid product is obtained by washing with distilled water and drying.
According to a preferable technical scheme, after the organic solvent is removed, the obtained solid is placed in a high-temperature water crystallization tank, the temperature is controlled to be 70-100 ℃, the heat preservation time is 60-180 min, the temperature is reduced to 30-50 ℃, and the long-chain dicarboxylic acid product is obtained through crystallization and separation. The separation is preferably centrifugation. After the separation, the drying treatment is preferably carried out, and the drying method is preferably flash evaporation.
In a preferred embodiment of the present invention, the method for recovering the organic solvent may be that a condensing device is externally connected to the paddle dryer, and the condensing device recovers the organic solvent.
The fourth object of the invention is a long-chain dicarboxylic acid product in which the organic solvent content is less than or equal to 450ppm, preferably less than or equal to 300 ppm.
The method can effectively recover the organic solvent on the basis of ensuring the purity and the extraction rate of the long-chain dibasic acid, the recovery rate of the organic solvent reaches more than 99 percent, and meanwhile, the wall bonding phenomenon of the long-chain dibasic acid does not occur in a machine. The solvent recovery and product refining are carried out at a relatively low temperature, and the method is very favorable for heat-sensitive substances. The scheme avoids washing filter cakes by water and the like, and can not cause organic solvent to enter water to form sewage or cause environmental pollution.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
Preparation of C10 long-chain dibasic acid fermentation liquor
(1) Activating strains: inoculating the glycerol tube strain of the candida tropicalis into a shake flask filled with 30ml of seed culture medium, wherein the pH is natural, and the shake culture is carried out for 24 hours at the temperature of 29 ℃ and the rpm of 220;
(2) preparing a seed solution: inoculating the shake flask seeds into a seed tank filled with a seed culture medium, wherein the initial pH value of the inoculated system is 6.0, the ventilation quantity is 0.5vvm at 29 ℃, the tank pressure is 0.1MPa, the system is cultured for 18h, the pH value is naturally reduced to 3 in the culture process, and the OD620 is grown to 15;
(3) fermentation: inoculating the seeds into a fermentation tank containing a fermentation culture medium, adding 10% (v/v) of n-decane hydrocarbon, controlling the temperature at 30 ℃ in the fermentation process, controlling the ventilation quantity at 0.5vvm and the tank pressure at about 0.1MPa (gauge pressure), adding a substrate or n-decane hydrocarbon, and fermenting; the total fermentation period is 130h, and the residual hydrocarbon content is basically 0 at the end of fermentation; obtaining C10 long-chain dicarboxylic acid fermentation liquor; or C10 long chain binary acid fermentation liquor, wherein the weight of the C10 long chain binary acid accounts for more than 95% of the total acid weight of the fermentation liquor.
Example 2
Preparation of C12 long-chain dibasic acid fermentation liquor
(1) Activating strains: inoculating the glycerol tube strain of the candida tropicalis into a shake flask filled with 30ml of seed culture medium, wherein the pH is natural, and the shake culture is carried out for 24 hours at the temperature of 29 ℃ and the rpm of 220;
(2) preparing a seed solution: inoculating the shake flask seeds into a seed tank filled with a seed culture medium, wherein the initial pH value of the inoculated system is 6.0, the ventilation quantity is 0.5vvm at 29 ℃, the tank pressure is 0.1MPa, the system is cultured for 18h, the pH value is naturally reduced to 3 in the culture process, and the OD620 is grown to 15;
(3) fermentation: inoculating the seeds into a fermentation tank containing a fermentation culture medium, adding 10% (v/v) n-dodecane, controlling the temperature at 30 ℃ in the fermentation process, controlling the ventilation quantity at 0.5vvm and the tank pressure at about 0.1MPa (gauge pressure), adding a substrate of n-dodecane, and fermenting; the total fermentation period is 130h, and the residual hydrocarbon content is basically 0 at the end of fermentation; obtaining C12 long-chain dicarboxylic acid fermentation liquor; in the C12 long-chain dibasic acid fermentation liquor, the weight of the C12 long-chain dibasic acid accounts for more than 95 percent of the total acid weight of the fermentation liquor.
Example 3
(1) Adjusting the pH value of C10 long-chain dibasic acid fermentation liquor obtained in example 1 to 2.8 by using sulfuric acid, acidifying, crystallizing and centrifugally separating to obtain a long-chain dibasic acid solid, dissolving the solid in acetic acid, adding activated carbon with the volume of less than 5% of that of clear liquid, decoloring for 90min at 93 ℃, separating to obtain clear liquid, cooling to 70 ℃, preserving heat for 1.5h, cooling to 30 ℃, crystallizing and centrifugally separating to obtain a long-chain dibasic acid crystal product;
(2) drying the long-chain dibasic acid crystallization product by a vacuum paddle dryer, removing acetic acid to obtain a solid, controlling the vacuum degree of the vacuum paddle dryer to be-0.05 MPa, controlling the drying temperature to be 98 ℃, and simultaneously further recovering an organic solvent by an external condensing device;
(3) washing and drying to obtain the long-chain dicarboxylic acid product.
Example 4
(1) Adjusting the pH value of C10 long-chain dibasic acid fermentation liquor obtained in example 1 to 3.4 by using sulfuric acid, acidifying, crystallizing and centrifugally separating to obtain a long-chain dibasic acid solid, dissolving the solid in acetic acid, adding activated carbon with the volume of less than 5% of that of clear liquid, decoloring for 60min at 95 ℃, separating to obtain clear liquid, cooling to 72 ℃, preserving heat for 2h, cooling to 32 ℃, crystallizing and centrifugally separating to obtain a long-chain dibasic acid crystal product;
(2) drying the long-chain dibasic acid crystallization product by a vacuum paddle dryer, removing acetic acid to obtain a solid, controlling the vacuum degree of the vacuum paddle dryer to be-0.04 MPa, controlling the drying temperature to be 102 ℃, and simultaneously further recovering an organic solvent by an external condensing device;
(3) putting the obtained solid into a crystallizing tank, adding water into the crystallizing tank, controlling the water temperature to be 100 ℃, preserving the heat for 120min, cooling to 45 ℃, crystallizing, centrifuging, and performing flash evaporation drying to obtain the long-chain dicarboxylic acid product.
Example 5
(1) Adjusting the pH value of C12 long-chain dibasic acid fermentation liquor obtained in the embodiment 2 to 3 by using sulfuric acid, acidifying, crystallizing and centrifuging to obtain a long-chain dibasic acid solid, dissolving the solid in acetic acid, adding activated carbon with the volume of less than 5% of that of clear liquid, decoloring for 120min at the temperature of 92 ℃, separating to obtain clear liquid, cooling to 76 ℃, preserving heat for 1.5h, cooling to 28 ℃, crystallizing and centrifuging to obtain a long-chain dibasic acid crystallization product;
(2) drying the long-chain dibasic acid crystallization product by a vacuum paddle dryer, removing acetic acid to obtain a solid, controlling the vacuum degree of the vacuum paddle dryer to be-0.045 MPa and the drying temperature to be 100 ℃, and simultaneously further recovering the organic solvent by an external condensing device;
(3) washing and drying to obtain the long-chain dicarboxylic acid product.
Example 6
(1) Adjusting the pH value of C12 long-chain dibasic acid fermentation liquor obtained in the embodiment 2 to 3.3 by using sulfuric acid, acidifying, crystallizing and centrifugally separating to obtain a long-chain dibasic acid solid, dissolving the solid in acetic acid, adding activated carbon with the volume of less than 5% of that of clear liquid, decoloring for 90min at 90 ℃, separating to obtain clear liquid, cooling to 78 ℃, preserving heat for 2h, cooling to 30 ℃, crystallizing and centrifugally separating to obtain a long-chain dibasic acid crystal product;
(2) drying the long-chain dibasic acid crystallization product by a vacuum paddle dryer, removing the organic solvent to obtain a solid, controlling the vacuum degree of the vacuum paddle dryer to be-0.06 MPa and the drying temperature to be 92 ℃, and simultaneously further recovering the organic solvent by an external condensing device;
(3) and putting the obtained solid into a crystallizing tank, adding water into the crystallizing tank, controlling the water temperature to be 95 ℃, preserving the heat for 150min, cooling to 40 ℃, crystallizing, centrifuging, and performing flash evaporation drying to obtain a long-chain dicarboxylic acid product.
Comparative example 1
In the step (2), the vacuum paddle dryer is controlled to dry at 120 ℃ under normal pressure, and the rest of the process is the same as that of the example 3.
Comparative example 2
In the step (2), the vacuum paddle dryer is controlled to dry at 102 ℃ under normal pressure, and the rest of the process is the same as that of the example 3.
Comparative example 3
(1) Adjusting the pH value of C12 long-chain dibasic acid fermentation liquor obtained in the embodiment 2 to 3.3 by using sulfuric acid, acidifying, crystallizing and centrifugally separating to obtain a long-chain dibasic acid solid, dissolving the solid in acetic acid, adding activated carbon with the volume of less than 5% of that of clear liquid, decoloring for 90min at 90 ℃, separating to obtain clear liquid, cooling to 78 ℃, preserving heat for 2h, cooling to 30 ℃, crystallizing and centrifugally separating to obtain a long-chain dibasic acid crystal product; simultaneously recovering acetic acid through a rectifying tower;
(2) and (3) putting the obtained long-chain dicarboxylic acid crystallization product into a crystallization tank, adding water into the crystallization tank, controlling the water temperature to be 95 ℃, keeping the temperature for 150min, cooling to 40 ℃, crystallizing, centrifuging, and performing flash evaporation and drying to obtain the long-chain dicarboxylic acid product.
The performance indexes of the long-chain dicarboxylic acid products obtained in examples 3 to 6 are shown in Table 1.
TABLE 1
| Item | Example 3 | Example 4 | Example 5 | Example 6 |
| Total acid content (%) | 99.73％ | 99.81％ | 99.77％ | 99.84％ |
| Content of Monoacid (%) | 99.60％ | 99.67％ | 99.53％ | 99.66％ |
| Total ammonia content (ppm) | 22 | 18 | 31 | 20 |
| Fe ion content (ppm) | 0.8 | 0.8 | 1.1 | 1.0 |
| Ash content (ppm) | 15 | 14 | 16 | 22 |
| Water content (%) | 0.4 | 0.4 | 0.4 | 0.4 |
| Colour(s) | Whitening agent | Whitening agent | Whitening agent | Whitening agent |
| Form of the composition | Powder of | Powder of | Powder of | Powder of |
| Organic solvent residue (ppm) | 319 | 215 | 402 | 204 |
| Recovery ratio of organic solvent (%) | >99％ | >99％ | >99％ | >99％ |
| Wall build-up phenomenon of machine | Wall without knot | Wall without knot | Wall without knot | Wall without knot |
In comparative example 1, the long-chain dibasic acid was partially melted to form a large lump, the local wall deposition was severe, and the machine was difficult to operate effectively.
In comparative example 2, 4000ppm of acetic acid remained in the long-chain dicarboxylic acid product, and the product quality was not qualified.
In comparative example 3, 300ppm of acetic acid remained in the long-chain dibasic acid product, but the acetic acid recovery rate was 80%.
In conclusion, the vacuum paddle dryer is used for removing or recycling the organic solvent in the process of extracting and purifying the long-chain dibasic acid for the first time, the parameters of the vacuum paddle dryer are optimized, so that the dibasic acid product is high in purity and low in organic solvent residue, and meanwhile, the vacuum paddle dryer does not have the phenomenon of machine wall bonding and can effectively run for a long time.
Claims (10)
1. The paddle dryer is preferably a vacuum paddle dryer and is used for removing or recycling the organic solvent in the process of extracting and purifying the long-chain dicarboxylic acid.
2. A method for removing organic solvents from a mixture of long chain dibasic acids, the method comprising the steps of: drying the long-chain dicarboxylic acid mixture to be treated by a vacuum paddle dryer, and removing the organic solvent; controlling the vacuum degree of the vacuum paddle dryer to be-0.02 to-0.1 MPa, and controlling the drying temperature of the vacuum paddle dryer to be 45-125 ℃.
3. The method of claim 2, wherein: the long-chain binary acid mixture comprises long-chain binary acid and an organic solvent;
the long-chain dibasic acid comprises: one or more of azelaic acid, sebacic acid, undecanedioic acid, dodecanedioic acid, tridecanedioic acid, tetradecanedioic acid, pentadecanedioic acid, hexadecanedioic acid, heptadecanedioic acid, octadecanedioic acid, and 9-ene octadecanedioic acid;
the organic solvent includes: one or more of alcohols, acids, ketones, and esters.
4. The method of claim 2, wherein: controlling the vacuum degree of the vacuum blade dryer to be-0.02 to-0.08 MPa, preferably-0.04 to-0.06 MPa;
and/or, controlling the drying temperature of the vacuum paddle dryer to be 75-125 ℃, preferably 80-115 ℃.
5. The method for extracting and refining the long-chain dicarboxylic acid comprises the following steps:
obtaining a long-chain dicarboxylic acid crude product from fermentation liquor, dissolving the long-chain dicarboxylic acid crude product in an organic solvent, crystallizing to obtain a long-chain dicarboxylic acid crystallization product, drying the long-chain dicarboxylic acid crystallization product by a vacuum paddle dryer, and removing the organic solvent to obtain the long-chain dicarboxylic acid product.
6. The method of claim 5, wherein: the method for obtaining the crude long-chain dicarboxylic acid from the fermentation liquor can be any one of the following methods:
acidifying fermentation liquor containing long-chain dibasic acid to obtain a crude product of the long-chain dibasic acid;
or acidifying the fermentation liquor containing the long-chain dibasic acid, and separating the crude long-chain dibasic acid and impurities to obtain the crude long-chain dibasic acid;
or adding alkali into the fermentation liquor containing the long-chain dicarboxylic acid to adjust the pH value to 7-11, heating to 60-100 ℃, carrying out solid-liquid separation, and then acidifying to obtain the crude long-chain dicarboxylic acid.
7. The method of claim 6, wherein:
dissolving the long-chain dicarboxylic acid crude product in an organic solvent, carrying out solid-liquid separation to obtain a clear solution, and recrystallizing to obtain a long-chain dicarboxylic acid crystallized product;
and/or dissolving the crude long-chain dicarboxylic acid in an organic solvent, decoloring, and recrystallizing to obtain a long-chain dicarboxylic acid crystallization product.
8. The method of any one of claims 5-7, wherein:
the crystallization is cooling crystallization; the cooling crystallization comprises the following steps: cooling to 65-80 ℃, keeping the temperature for 1-2 hours, then cooling to 25-35 ℃, and crystallizing.
9. The method of any one of claims 5-7, wherein:
after the organic solvent is removed, washing with distilled water, and drying to obtain a long-chain dicarboxylic acid product;
and/or after the organic solvent is removed, putting the obtained solid into a high-temperature water crystallization tank, controlling the temperature to be 70-100 ℃, keeping the temperature for 60-180 min, cooling to 30-50 ℃, crystallizing, and separating to obtain the long-chain dicarboxylic acid product.
10. The long chain dicarboxylic acid product prepared by the method according to any one of claims 2 to 9, wherein: the content of the organic solvent in the long-chain dicarboxylic acid product is less than or equal to 450ppm, preferably less than or equal to 300 ppm.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112321418A (en) * | 2020-11-24 | 2021-02-05 | 淮安清江石油化工有限责任公司 | Refining method of long-chain dibasic acid |
| CN114716311A (en) * | 2021-01-04 | 2022-07-08 | 上海凯赛生物技术股份有限公司 | Double aqueous phase extraction process of long-chain dibasic acid, product and application |
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| CN111592453B (en) | 2023-07-25 |
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