CN110028402B - Method for extracting 3-hydroxypropionic acid - Google Patents
Method for extracting 3-hydroxypropionic acid Download PDFInfo
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Abstract
The invention provides a method for extracting 3-hydroxypropionic acid, which comprises the following steps: flocculating the fermentation liquor containing the 3-hydroxypropionic acid, and then extracting and back-extracting to obtain a 3-hydroxypropionic acid solution; the method achieves the purpose of separating and extracting the 3-hydroxypropionic acid from the fermentation liquor of the 3-hydroxypropionic acid by selecting a specific flocculating agent, a coagulant aid and a complex extraction system, can remove more impurities such as 2, 3-butanediol, 1, 3-butanediol, succinic acid, acetic acid and the like compared with the existing method for extracting the 3-hydroxypropionic acid from the fermentation liquor by independently utilizing flocculation, membrane separation and centrifugation methods, has the thallus removal rate of more than 99 percent, the extraction rate of more than 80 percent, the final yield of the 3-hydroxypropionic acid of more than 50 to 70 percent and the purity of more than 60 percent, has important reference value for the industrial production of the 3-hydroxypropionic acid, and has good application prospect.
Description
Technical Field
The invention belongs to the field of chemical separation, and relates to a method for extracting 3-hydroxypropionic acid.
Background
The 3-hydroxypropionic acid is an achiral organic acid with three carbon atoms, has an acid dissociation constant of 4.5, is in a liquid state, is viscous, colorless and odorless, and is soluble in water, ethanol and diethyl ether. Can be used for synthesizing various chemicals such as acrylic acid and the like. 3-hydroxypropionic acid is an isomer of lactic acid (2-hydroxypropionic acid) and is chemically more reactive due to the different positions of the hydroxyl groups. A plurality of important chemical substances such as acrylic acid and malonic acid, as well as biodegradable plastic poly-3-hydroxypropionic acid can be synthesized through oxidation, dehydration, esterification reaction and the like, and the compound can also be used as an additive and a preservative of food or feed.
CN107353197A discloses a method for extracting 3-hydroxypropionic acid, comprising the following steps: 1) mixing the crude water solution containing the 3-hydroxypropionic acid with an organic solvent, and evaporating and concentrating the mixed solution to remove water to obtain the organic solvent containing the 3-hydroxypropionic acid; 2) extracting the 3-hydroxypropionic acid obtained in the step 1). However, the method cannot be applied to separation and extraction of 3-hydroxypropionic acid prepared by a biological synthesis method, and has certain limitations.
CN109704950A discloses a separation and purification method of 3-hydroxypropionic acid, which comprises the following steps: the method comprises the following steps: 1. mixing a crude water solution containing 3-hydroxypropionic acid with an organic solvent, adding 15-35 times of glacial ethanol in volume into the mixed solution to precipitate poly (3-hydroxypropionic acid), and extracting; step 2, cleaning the obtained precipitate with ethanol, and drying in vacuum for 45-60min to obtain high-purity poly-3-hydroxypropionic acid; step 3, adding the combined solvent into the solution remaining after extraction in the step 1, then distilling and concentrating, and further carrying out recrystallization; and 4, filtering the solution recrystallized in the step 3, and extracting the obtained 3-hydroxypropionic acid. The method has more steps related to transfer, and is easy to cause product loss and waste.
CN106588642A discloses a p-hydroxyphenylpropionic acid extracted from cortex mori, a preparation method and an application thereof, which effectively solve the problems of p-hydroxyphenylpropionic acid extraction from the cortex mori and the application thereof in the preparation of HPAEC (hydroxy propyl phenol acetic acid) damage drugs induced by LPS (lipopolysaccharide) and the like, the cortex mori is decocted and extracted, an extracting solution is decompressed and concentrated to obtain a dry substance, the dry substance is added with distilled water for suspension, a resin column is put on, water and ethanol are sequentially used for gradient elution, each gradient eluent is concentrated to be dry, the dry substance is dissolved by methanol, silica gel is added and added on the liquid level of a chromatographic column for gradient elution, each flow is analyzed by TLC, combined and decompressed and concentrated to obtain total samples A1, A2 and A3; dissolving the total sample A1 with methanol, loading on a Toyopearl HW-40 column, eluting with methanol, detecting with thin layer, mixing to obtain sub-stream A1-2, concentrating under reduced pressure, drying, dissolving with methanol, loading on ODS column, eluting with methanol, detecting with thin layer, mixing the same sub-streams, and concentrating under reduced pressure to obtain p-hydroxyphenylpropionic acid; the method mainly adopts a chromatographic method for separation and extraction, and is not suitable for separating 3-hydroxypropionic acid.
At present, the separation and extraction of 3-hydroxypropionic acid is mainly performed by distillation, centrifugation, membrane filtration and the like, and 3-hydroxypropionic acid cannot be effectively extracted from a solution such as fermentation liquor, so how to develop a new extraction process has important value for industrial application of 3-hydroxypropionic acid.
Disclosure of Invention
Aiming at the defects of the prior art, the invention aims to provide a method for extracting 3-hydroxypropionic acid, so as to solve the problems of low extraction efficiency and low purity in the prior art.
In order to achieve the purpose, the invention adopts the following technical scheme:
the invention provides a method for extracting 3-hydroxypropionic acid, which comprises the following steps: flocculating the fermentation liquor containing the 3-hydroxypropionic acid, and then extracting and back-extracting to obtain a 3-hydroxypropionic acid solution.
Compared with the existing method for extracting 3-hydroxypropionic acid from fermentation liquor by independently utilizing flocculation, membrane separation and centrifugation methods, the method can remove more impurities such as 2, 3-butanediol, 1, 3-butanediol, succinic acid, acetic acid and the like, the removal rate of thalli can reach more than 99%, the extraction rate can reach more than 80%, the final yield of the 3-hydroxypropionic acid can reach 50% -70%, and the purity can reach more than 60%.
Preferably, the flocculation method is as follows: adding a polymeric aluminum ferric silicate solution into fermentation liquor containing 3-hydroxypropionic acid, and standing to obtain supernatant.
The polymeric aluminum ferric silicate is a novel water-soluble polymer electrolyte. At present, the method is mainly used for purifying drinking water, and can also be used for special water quality treatment of water supply, cadmium removal, fluorine removal, radioactive pollution removal, floating oil removal and the like. The invention surprisingly discovers that when polyaluminum ferric silicate is used for flocculation in fermentation liquor, the removal effect on thalli is very good, and some common flocculating agents such as diatomite and the like have almost no flocculation effect.
The volume ratio of the fermentation liquid containing 3-hydroxypropionic acid to the polyaluminum ferric silicate solution is preferably (5-20): 1, and may be, for example, 5:1, 7:1, 8:1, 9:1, 10:1, 12:1, 15:1, 16:1, 18:1 or 20:1, and is preferably (8-10): 1.
In the flocculation process, the control of the using amount of the polymeric aluminum ferric silicate is important for the flocculation effect, and the flocculation effect is optimal when the using amount is preferably controlled within the range of (8-10): 1. In the flocculation process, under the action of polymeric aluminum ferric silicate, thalli are aggregated under the actions of bridging and the like, and finally precipitate is formed.
Preferably, the concentration of the polymeric aluminum ferric silicate solution is 15-30 g/L, for example, 15g/L, 18g/L, 20g/L, 23g/L, 25g/L, 28g/L or 30 g/L.
Preferably, the pH value of the fermentation liquid containing 3-hydroxypropionic acid is 5-9, for example, 5, 6, 7, 8, or 9, preferably 7.
In the actual flocculation process, too low or too high pH value can reduce the flocculation effect, and the optimal pH value is 7.
Preferably, the standing time is 20-50 min, for example, 20min, 25min, 30min, 35min, 40min, 45min or 50 min.
Preferably, the temperature of the standing is 20 to 50 ℃, for example, 20 ℃, 25 ℃, 30 ℃, 35 ℃, 40 ℃, 45 ℃ or 50 ℃ and the like.
Preferably, the step of adding a coagulant aid is further included after the step of adding the polyaluminum ferric silicate solution.
Preferably, the coagulant aid is a sodium alginate solution.
Preferably, the concentration of the sodium alginate solution is 5-10 g/L, for example, 5g/L, 6g/L, 7g/L, 8g/L, 9g/L or 10g/L, etc., preferably 8 g/L.
In the flocculation process, the sodium alginate can realize the thickening effect, promote to form large micelle and accelerate the precipitation effect. When the sodium alginate is used in combination with the polymeric aluminum ferric silicate, the thallus is completely removed, and the loss of the product is less.
Preferably, after the flocculation, the supernatant obtained by the flocculation is subjected to the steps of extraction and back extraction.
Preferably, the method of extraction is complex extraction.
Preferably, the step of complex extraction is: adding the n-dodecanol solution of trioctylamine into the supernatant for complexation extraction, and collecting the organic phase.
In the invention, n-dodecanol, as a solvent for trioctylamine, contributes more to the extraction distribution coefficient, and is more beneficial to extraction than other solvents due to the higher dosage form and dipole-polarization rate of n-dodecanol.
The volume ratio of the n-dodecanol solution of trioctylamine to the supernatant is preferably (0.7-1.5): 1, and may be, for example, 0.7:1, 0.8:1, 0.9:1, 1:1, 1.1:1, 1.2:1, 1.3:1, 1.4:1 or 1.5:1, and preferably 1.2: 1.
In the present invention, the higher the content of the supernatant, the lower the extraction rate gradually. When the content of the supernatant is lower, more trioctylamine is contained in the organic phase, and the extraction effect is better; however, too low a content of the supernatant also has an effect on the extraction yield. Preferably the volume ratio is 1.2: 1.
Preferably, the volume fraction of the trioctylamine in the n-dodecanol is 20% to 40%, for example, 20%, 22%, 25%, 30%, 35%, 38%, 40%, etc., preferably 35%.
In the invention, the volume fraction of the trioctylamine in the n-dodecanol is controlled within a certain range, and if the volume fraction is too high, the amount of the n-dodecanol is relatively small, so that the solvation of the extract compound in the organic phase is weakened, and the extraction effect is reduced.
Preferably, the temperature of the complex extraction is 10-15 ℃, for example, 10 ℃, 11 ℃, 12 ℃, 13 ℃, 14 ℃ or 15 ℃.
In the present invention, the temperature of the complex extraction cannot be too high, and since the extraction reaction is an exothermic reaction, a lower temperature is favorable for the forward direction of the reaction. Therefore, the temperature increases and the extraction efficiency decreases.
Preferably, the pH value of the complexing extraction is 3-5, for example, 3, 3.5, 4, 4.5 or 5.
The pH can be adjusted to the appropriate range by the skilled person by means of customary acids or bases as required. The pH value of the complex extraction is most suitable to be 3-5.
Preferably, the stripping method comprises the following steps: the sodium hydroxide solution is mixed with the organic phase for back extraction.
In the invention, 3-hydroxypropionic acid is extracted from an organic phase to a water phase by a back extraction method, so that the final separation is realized.
Preferably, the concentration of the sodium hydroxide solution is 2 to 4mol/L, and may be, for example, 2mol/L, 2.2mol/L, 2.5mol/L, 3mol/L, 3.1mol/L, 3.5mol/L, 3.7mol/L, or 4 mol/L.
Preferably, the volume ratio of the sodium hydroxide solution to the organic phase is (3-5: 1), and may be, for example, 3:1, 3.2:1, 3.5:1, 4:1, 4.3:1, 4.6:1, or 5: 1.
Preferably, the temperature of the back extraction is 30 to 50 ℃, for example, 30 ℃, 35 ℃, 40 ℃, 45 ℃ or 50 ℃ and the like.
Preferably, the method comprises the steps of:
adding a polymeric aluminum ferric silicate solution with the concentration of 15-30 g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 5-9, and standing for 20-50 min at the temperature of 20-50 ℃ in the presence of a coagulant aid with the concentration of 5-10 g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is (5-20): 1;
performing complex extraction on the supernatant by using a trioctylamine n-dodecanol solution with the volume fraction of 20-40% at the temperature of 10-15 ℃ and the pH value of 3-5, wherein the volume ratio of the trioctylamine n-dodecanol solution to the supernatant is (0.7-1.5): 1, collecting an organic phase, mixing the organic phase with a sodium hydroxide solution with the concentration of 2-4 mol/L, the volume ratio of the sodium hydroxide solution to the organic phase is (3-5): 1, performing back extraction at the temperature of 30-50 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Compared with the prior art, the invention has the following beneficial effects:
the invention achieves the purpose of separating and extracting 3-hydroxypropionic acid from the fermentation liquor of the 3-hydroxypropionic acid by combining flocculation, extraction and back extraction steps and selecting a specific flocculating agent, a coagulant aid and a complex extraction system, compared with the existing method for extracting 3-hydroxypropionic acid from the fermentation liquor by independently utilizing flocculation, membrane separation and centrifugation, the method can remove more impurities such as 2, 3-butanediol, 1, 3-butanediol, succinic acid, acetic acid and the like, the thallus removal rate can reach more than 99 percent, the extraction rate can reach more than 80 percent, the final yield of the 3-hydroxypropionic acid can reach 50 to 70 percent, the purity can reach more than 60 percent, and the method has important reference value for industrial production of the 3-hydroxypropionic acid and good application prospect.
Detailed Description
The technical solution of the present invention is further explained by the following embodiments. It should be understood by those skilled in the art that the examples are only for the understanding of the present invention and should not be construed as the specific limitations of the present invention.
Example 1
This example extracts 3-hydroxypropionic acid from a fermentation broth by the following method
Adding 20g/L polymeric aluminum ferric silicate solution into the fermentation liquor containing 3-hydracrylic acid with the pH value of 7, and standing for 30min at the temperature of 30 ℃ in the presence of 8g/L sodium alginate to obtain supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydracrylic acid to the polymeric aluminum ferric silicate solution is 9: 1;
performing complexation extraction on the supernatant by using 35% by volume of n-dodecanol solution of trioctylamine at the temperature of 10 ℃ and the pH value of 4, wherein the volume ratio of the n-dodecanol solution of trioctylamine to the supernatant is 1.2:1, collecting an organic phase, mixing the organic phase with 3mol/L sodium hydroxide solution at the volume ratio of sodium hydroxide solution to organic phase of 4:1, performing back extraction at the temperature of 40 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Example 2
This example extracts 3-hydroxypropionic acid from a fermentation broth by the following method
Adding a polymeric aluminum ferric silicate solution with the concentration of 30g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 7, and standing for 20min at 50 ℃ in the presence of sodium alginate with the concentration of 10g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is 10: 1;
performing complexation extraction on the supernatant by using a trioctylamine n-dodecanol solution with the volume fraction of 40% at the temperature of 15 ℃ and the pH value of 5, wherein the volume ratio of the trioctylamine n-dodecanol solution to the supernatant is 1.5:1, collecting an organic phase, mixing the organic phase with a sodium hydroxide solution with the concentration of 4mol/L, the volume ratio of the sodium hydroxide solution to the organic phase is 5:1, performing back extraction at the temperature of 50 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Example 3
This example extracts 3-hydroxypropionic acid from a fermentation broth by the following method
Adding a polymeric aluminum ferric silicate solution with the concentration of 15g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 7, and standing for 50min at the temperature of 20 ℃ in the presence of sodium alginate with the concentration of 5g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is 8: 1;
performing complex extraction on the supernatant by using a trioctylamine n-dodecanol solution with the volume fraction of 20% at the temperature of 10 ℃ and the pH value of 3, wherein the volume ratio of the trioctylamine n-dodecanol solution to the supernatant is 1.3:1, collecting an organic phase, mixing the organic phase with a sodium hydroxide solution with the concentration of 4mol/L, the volume ratio of the sodium hydroxide solution to the organic phase is 5:1, performing back extraction at the temperature of 30 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Example 4
This example extracts 3-hydroxypropionic acid from a fermentation broth by the following method
Adding a polymeric aluminum ferric silicate solution with the concentration of 19g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 7, and standing for 35min at the temperature of 40 ℃ in the presence of sodium alginate with the concentration of 7g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is 20: 1;
performing complex extraction on the supernatant by using 28 volume percent of n-dodecanol solution of trioctylamine at the temperature of 13 ℃ and the pH value of 4, wherein the volume ratio of the n-dodecanol solution of trioctylamine to the supernatant is 0.7:1, collecting an organic phase, mixing the organic phase with 3mol/L sodium hydroxide solution at the volume ratio of sodium hydroxide solution to organic phase of 4:1, performing back extraction at the temperature of 45 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Example 5
This example extracts 3-hydroxypropionic acid from a fermentation broth by the following method
Adding a polymeric aluminum ferric silicate solution with the concentration of 25g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 7, and standing for 45min at the temperature of 25 ℃ in the presence of sodium alginate with the concentration of 5g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is 5: 1;
performing complex extraction on the supernatant by using 28 volume percent of n-dodecanol solution of trioctylamine at the temperature of 13 ℃ and the pH value of 5, wherein the volume ratio of the n-dodecanol solution of trioctylamine to the supernatant is 0.9:1, collecting an organic phase, mixing the organic phase with 3mol/L sodium hydroxide solution at the volume ratio of sodium hydroxide solution to organic phase of 4:1, performing back extraction at the temperature of 50 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
Example 6
This example differs from example 1 in that the pH of the fermentation broth containing 3-hydroxypropionic acid is 5.
Example 7
This example differs from example 1 in that the pH of the fermentation broth containing 3-hydroxypropionic acid in this example was 9.
Example 8
This example differs from example 1 in that the volume ratio of the fermentation broth containing 3-hydroxypropionic acid to the polyaluminum ferric silicate solution in this example was 2: 1.
Example 9
This example differs from example 1 in that the volume ratio of the fermentation broth containing 3-hydroxypropionic acid to the polyaluminum ferric silicate solution in this example was 25: 1.
Example 10
This example differs from example 1 in that the volume ratio of n-dodecanol solution containing trioctylamine to supernatant in this example was 1.8: 1.
Example 11
This example differs from example 1 in that the volume ratio of n-dodecanol solution containing trioctylamine to supernatant in this example was 0.4: 1.
Example 12
This example differs from example 1 in that the temperature of complexation extraction in this example is 25 ℃.
Example 13
This example differs from example 1 in that chitosan was used as a flocculant instead of polyaluminum ferric silicate in the flocculation step.
Example 14
This example differs from example 1 in that in this example, a solution of trioctylamine in n-octanol was used for the complexation extraction.
Comparative example 1
This comparative example differs from example 1 in that it only performs the flocculation step and does not include the extraction, stripping steps.
The 3-hydroxypropionic acid solutions extracted from examples 1 to 14 and comparative example 1 were subjected to the determination of yield and purity. The yield is the ratio of the mass of the 3-hydroxypropionic acid contained in the extracted 3-hydroxypropionic acid solution to the mass of the 3-hydroxypropionic acid contained in the fermentation broth; the purity is the mass percentage of the 3-hydroxypropionic acid contained in the extracted 3-hydroxypropionic acid solution. The quality is detected by high performance liquid chromatography (Agilent 1100 HPLC) with C column18The column temperature is 30 ℃, the ultraviolet absorption wavelength is 210nm, the volume ratio of water, phosphoric acid and methanol in the mobile phase is 950.00:0.50:50.00, the flow rate is 0.80mL/min, the sample injection amount is 20.00 mu L, the external standard method is adopted for quantification, and the specific results are shown in the following table 1:
TABLE 1
As can be seen from the data in Table 1, the factors affecting the yield and purity of 3-hydroxypropionic acid are manifold.
As is clear from comparison of examples 1-5 and 8-9, the flocculation effect is better when the volume ratio of the fermentation liquid of 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is controlled within the range of (8-10): 1.
As is clear from the comparison between example 1 and examples 6 to 7, the pH of the fermentation broth affects the yield and purity, and the optimum pH is preferably controlled to about 7.
As can be seen from the comparison of example 1 with examples 10 to 11, the extraction efficiency is the best when the volume ratio of the n-dodecanol solution containing trioctylamine to the supernatant is 1.2:1, while the extraction efficiency is reduced when the supernatant is too much or too little.
As can be seen from the comparison of example 1 with example 12, the effect of the temperature of the complex extraction on the yield and purity is very significant, and the extraction yield is greatly reduced as the temperature is increased.
As can be seen by comparing example 1 with examples 13-14, the yield and purity of 3-hydroxypropionic acid is affected when the flocculant or complex extraction system is changed.
As is clear from comparison of example 1 with the comparative example, when flocculation was carried out alone, the yield of 3-hydroxypropionic acid was not affected, but the purity was less than 40%, and the purity could not meet the requirements.
The applicant states that the present invention is illustrated in detail by the above examples, but the present invention is not limited to the above detailed methods, i.e. it is not meant that the present invention must rely on the above detailed methods for its implementation. It should be understood by those skilled in the art that any modification of the present invention, equivalent substitutions of the raw materials of the product of the present invention, addition of auxiliary components, selection of specific modes, etc., are within the scope and disclosure of the present invention.
Claims (23)
1. A method of extracting 3-hydroxypropionic acid, the method comprising: flocculating the fermentation liquor containing the 3-hydroxypropionic acid, and then extracting and back-extracting to obtain a 3-hydroxypropionic acid solution;
the flocculation method comprises the following steps: adding a polymeric aluminum ferric silicate solution into fermentation liquor containing 3-hydroxypropionic acid, and standing to obtain supernatant;
the volume ratio of the fermentation liquor containing the 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is (5-20): 1;
the concentration of the polymeric aluminum ferric silicate solution is 15-30 g/L;
the pH value of the fermentation liquor containing the 3-hydroxypropionic acid is 5-9.
2. The method according to claim 1, wherein the volume ratio of the fermentation liquid containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is (8-10): 1.
3. The method of claim 1, wherein the fermentation broth comprising 3-hydroxypropionic acid has a pH of 7.
4. The method according to claim 1, wherein the standing time is 20-50 min.
5. The method according to claim 1, wherein the temperature of the standing is 20 to 50 ℃.
6. The method of claim 1, further comprising the step of adding a coagulant aid after the step of adding the polyaluminum ferric silicate solution.
7. The method of claim 6, wherein the coagulant aid is a sodium alginate solution.
8. The method as claimed in claim 7, wherein the concentration of the sodium alginate solution is 5-10 g/L.
9. The method as claimed in claim 8, wherein the concentration of the sodium alginate solution is 8 g/L.
10. The method according to claim 1, characterized in that after flocculation, the supernatant obtained by flocculation is subjected to extraction and back extraction steps.
11. The method of claim 10, wherein the extraction method is complex extraction.
12. The method of claim 11, wherein the step of complex extraction is: adding the n-dodecanol solution of trioctylamine into the supernatant for complexation extraction, and collecting the organic phase.
13. The method according to claim 12, wherein the volume ratio of the n-dodecanol solution of trioctylamine to the supernatant is (0.7-1.5): 1.
14. The method of claim 13, wherein the volume ratio of n-dodecanol solution of trioctylamine to supernatant is 1.2: 1.
15. The method of claim 12, wherein the volume fraction of trioctylamine in n-dodecanol is 20% to 40%.
16. The method of claim 15, wherein the trioctylamine is present in the n-dodecanol at a volume fraction of 35%.
17. The method according to claim 11, wherein the temperature of the complex extraction is 10-15 ℃.
18. The method according to claim 11, wherein the pH value of the complex extraction is 3-5.
19. The method of claim 10, wherein the stripping process comprises: the sodium hydroxide solution is mixed with the organic phase for back extraction.
20. The method according to claim 19, wherein the concentration of the sodium hydroxide solution is 2-4 mol/L.
21. The method according to claim 19, wherein the volume ratio of the sodium hydroxide solution to the organic phase is (3-5): 1.
22. The method according to claim 10, wherein the temperature of the stripping is 30 to 50 ℃.
23. Method according to claim 1, characterized in that it comprises the following steps:
adding a polymeric aluminum ferric silicate solution with the concentration of 15-30 g/L into a fermentation liquor containing 3-hydroxypropionic acid with the pH value of 5-9, and standing for 20-50 min at the temperature of 20-50 ℃ in the presence of a coagulant aid with the concentration of 5-10 g/L to obtain a supernatant, wherein the volume ratio of the fermentation liquor containing 3-hydroxypropionic acid to the polymeric aluminum ferric silicate solution is (5-20): 1;
performing complex extraction on the supernatant by using a trioctylamine n-dodecanol solution with the volume fraction of 20-40% at the temperature of 10-15 ℃ and the pH value of 3-5, wherein the volume ratio of the trioctylamine n-dodecanol solution to the supernatant is (0.7-1.5): 1, collecting an organic phase, mixing the organic phase with a sodium hydroxide solution with the concentration of 2-4 mol/L, the volume ratio of the sodium hydroxide solution to the organic phase is (3-5): 1, performing back extraction at the temperature of 30-50 ℃, collecting an aqueous phase, and obtaining the 3-hydroxypropionic acid.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1832915A (en) * | 2003-06-26 | 2006-09-13 | 嘉吉有限公司 | Process for separating and recovering 3-hydroxypropionic acid and acrylic acid |
| CN101823953A (en) * | 2010-03-31 | 2010-09-08 | 北京科技大学 | Method for separating lactic acid from fermentation liquor by flocculation and carrying out flocculate comprehensive utilization |
| JP2013023481A (en) * | 2011-07-22 | 2013-02-04 | Nippon Shokubai Co Ltd | Method for handling or storing 3-hydroxypropionic acid solution |
| CN103922489A (en) * | 2014-05-09 | 2014-07-16 | 四川清和科技有限公司 | Microorganism composite flocculant coagulation bacterium application method |
| CN103998108A (en) * | 2011-12-23 | 2014-08-20 | 普拉克生化公司 | Lactic acid extraction |
| WO2014144400A1 (en) * | 2013-03-15 | 2014-09-18 | Cargill, Incorporated | Recovery of 3-hydroxypropionic acid |
| CN107353197A (en) * | 2017-06-09 | 2017-11-17 | 安徽丰原发酵技术工程研究有限公司 | A kind of method for extracting 3 hydracrylic acids |
-
2019
- 2019-05-30 CN CN201910464861.8A patent/CN110028402B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1832915A (en) * | 2003-06-26 | 2006-09-13 | 嘉吉有限公司 | Process for separating and recovering 3-hydroxypropionic acid and acrylic acid |
| CN101823953A (en) * | 2010-03-31 | 2010-09-08 | 北京科技大学 | Method for separating lactic acid from fermentation liquor by flocculation and carrying out flocculate comprehensive utilization |
| JP2013023481A (en) * | 2011-07-22 | 2013-02-04 | Nippon Shokubai Co Ltd | Method for handling or storing 3-hydroxypropionic acid solution |
| CN103998108A (en) * | 2011-12-23 | 2014-08-20 | 普拉克生化公司 | Lactic acid extraction |
| WO2014144400A1 (en) * | 2013-03-15 | 2014-09-18 | Cargill, Incorporated | Recovery of 3-hydroxypropionic acid |
| CN103922489A (en) * | 2014-05-09 | 2014-07-16 | 四川清和科技有限公司 | Microorganism composite flocculant coagulation bacterium application method |
| CN107353197A (en) * | 2017-06-09 | 2017-11-17 | 安徽丰原发酵技术工程研究有限公司 | A kind of method for extracting 3 hydracrylic acids |
Non-Patent Citations (2)
| Title |
|---|
| 3-羟基丙酸发酵液絮凝-脱色工艺研究;曹哲统;《北京化工大学学报（自然科学版）》;20170120;第44卷(第1期);第45-51页 * |
| 肺炎克雷伯氏杆菌代谢产物3-HP的分离;赵超楠;《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》;20190115;B018-217 * |
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