CN112745215B - Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material - Google Patents
Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material Download PDFInfo
- Publication number
- CN112745215B CN112745215B CN201911048850.8A CN201911048850A CN112745215B CN 112745215 B CN112745215 B CN 112745215B CN 201911048850 A CN201911048850 A CN 201911048850A CN 112745215 B CN112745215 B CN 112745215B
- Authority
- CN
- China
- Prior art keywords
- lactic acid
- lactate
- water
- carbon dioxide
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 title claims abstract description 112
- 239000004310 lactic acid Substances 0.000 title claims abstract description 56
- 235000014655 lactic acid Nutrition 0.000 title claims abstract description 56
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 title claims abstract description 28
- 239000002994 raw material Substances 0.000 title claims abstract description 14
- 238000010168 coupling process Methods 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 claims abstract description 55
- 238000006243 chemical reaction Methods 0.000 claims abstract description 44
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 42
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 21
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 21
- 239000003960 organic solvent Substances 0.000 claims abstract description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000012074 organic phase Substances 0.000 claims abstract description 11
- 238000000605 extraction Methods 0.000 claims abstract description 10
- 238000000926 separation method Methods 0.000 claims abstract description 10
- 239000012071 phase Substances 0.000 claims abstract description 6
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000011259 mixed solution Substances 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- 150000003893 lactate salts Chemical class 0.000 claims description 9
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- 230000008878 coupling Effects 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract description 13
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 abstract description 10
- 230000020477 pH reduction Effects 0.000 abstract description 6
- 239000002910 solid waste Substances 0.000 abstract description 4
- 239000002535 acidifier Substances 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 2
- 150000002148 esters Chemical class 0.000 abstract description 2
- 150000002170 ethers Chemical class 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 229940001447 lactate Drugs 0.000 description 22
- 238000000855 fermentation Methods 0.000 description 21
- 230000004151 fermentation Effects 0.000 description 21
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 description 12
- 239000001527 calcium lactate Substances 0.000 description 12
- 229960002401 calcium lactate Drugs 0.000 description 12
- 235000011086 calcium lactate Nutrition 0.000 description 12
- 239000007788 liquid Substances 0.000 description 8
- 229910000019 calcium carbonate Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 5
- 239000012527 feed solution Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- -1 lactate ion Chemical class 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- CYDQOEWLBCCFJZ-UHFFFAOYSA-N 4-(4-fluorophenyl)oxane-4-carboxylic acid Chemical compound C=1C=C(F)C=CC=1C1(C(=O)O)CCOCC1 CYDQOEWLBCCFJZ-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241001052560 Thallis Species 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000012538 ammonium bicarbonate Nutrition 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- HLKMEIITONDPGG-UHFFFAOYSA-L barium(2+);2-hydroxypropanoate Chemical compound [Ba+2].CC(O)C([O-])=O.CC(O)C([O-])=O HLKMEIITONDPGG-UHFFFAOYSA-L 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000005501 phase interface Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Abstract
A coupling method for converting lactic acid from a water-containing raw material of lactate and extracting the lactic acid comprises the steps of mixing the water-containing raw material of the lactate with an organic solvent, continuously introducing carbon dioxide into the mixed solution, reacting under the conditions that the pressure is not less than 7MPa and the temperature is not less than 30 ℃, and separating an organic phase and a water phase after the reaction is finished, wherein the organic phase contains the lactic acid; the organic solvent is an organic solvent which can dissolve lactic acid but is not completely dissolved with water, and is selected from at least one of esters, ethers and ketones with the C atom number being more than or equal to 5. The method can simultaneously carry out the conversion and extraction of the lactic acid on the water-containing raw material, and compared with the traditional sulfuric acid acidification method, the method uses carbon dioxide to replace sulfuric acid as an acidifier, does not generate calcium sulfate solid waste, and is a green pollution-free separation method.
Description
Technical Field
The present invention relates to the production and conversion of lactic acid, and is especially the phase-coupled process of converting lactic acid from water containing lactate.
Background
Lactic acid is widely used in the fields of food, medicine, chemical industry, new materials and the like, for example, as a flavoring agent, an antistaling agent, a preservative and the like in the food industry, and as a cosolvent, a prodrug preparation, a carrier agent and the like in the medicine industry. Polylactic acid (PLA) synthesized by taking lactic acid as a monomer is a new bio-based degradation material which is mainly supported by China, can replace petrochemical-based plastic products, and eliminates the white pollution of the environment. At present, the biological fermentation method is mostly adopted for producing lactic acid in industry. The lactic acid fermentation liquor is a system with very complex components, and besides lactic acid or lactate, a large amount of thalli, protein, residual sugar, pigment, inorganic salt, byproduct organic acid, unconverted starch and the like exist, and the existence of the impurities brings great difficulty for the subsequent separation and purification of lactic acid, so that the product is obtained through a long process.
In the process of producing lactic acid by fermentation, the pH in the fermentation broth decreases to a level that affects the fermentation activity of the microorganism as the produced lactic acid increases. A commonly used method is the addition of a base, salt or metal oxide that can be neutralized with lactic acid, including but not limited to calcium carbonate, calcium hydroxide, magnesium oxide, magnesium hydroxide, sodium carbonate, ammonium hydroxide, and the like. Therefore, most of the lactic acid in the fermentation broth obtained by the method is free lactate anion, and the free lactate ion needs to be converted into lactic acid through acidification in the subsequent process.
Taking a common calcium salt acidification method as an example, calcium carbonate is added in the fermentation process to neutralize the generated lactic acid to form calcium lactate, the used acidulant is sulfuric acid, and calcium sulfate solids are separated and removed after acidification to obtain a crude lactic acid solution. The process is the main method for producing the lactic acid at present, has the advantages of mature process, easy control and the like, but the concentrated sulfuric acid used for acidification and the generated calcium sulfate can cause pollution.
CN103153935A discloses a method for preparing barium lactate by reacting sugar with barium hydroxide, and contacting with ammonia or amine and with carbon dioxide, or with carbonate and/or bicarbonate of ammonia or amine, thereby preparing lactic acid-amine complex and barium carbonate. The method takes sugar as raw material, generates lactic acid by a chemical reaction method, and provides an extraction scheme of the lactic acid. The method chemically produces lactic acid, and provides a method for extracting lactic acid. However, lactic acid produced by the method is racemic, heavy metal is used in the method, and the product is a lactic acid-amine complex which still needs to be further separated.
The study on the conversion of calcium lactate to lactic acid under supercritical conditions [ C ]// tenth national academy of supercritical fluid technology and application, and the third academy of supercritical fluid technology at both sides of the strait, 2015, 386-392, proposes that carbon dioxide in a supercritical state can be used as an acidulant to produce calcium carbonate solids. Wherein the carbon dioxide can be derived from the fermentation process and the calcium carbonate produced can also be recycled as a neutralising agent for the fermentation process. Meanwhile, the method does not use sulfuric acid which is easy to cause pollution, does not generate a large amount of waste such as calcium sulfate, and is a green pollution-free separation method. However, studies have also found that the process conditions to achieve high conversion are: the temperature is 31-32 ℃, the pressure is 13-14MPa, the calcium lactate accounts for 2.3 percent of the mass fraction of the fermentation broth, the reaction balance can be achieved within 1.5h, and the conversion rate can reach more than 80 percent. There is a first problem: the operating pressure is too high; the second problem is that: the content of calcium lactate in the fermentation broth is far lower than that of lactate in the fermentation broth generated in the fermentation process under the industrial operation scale (the mass fraction of lactate in the fermentation broth is more than 10 percent). When the mass fraction of calcium lactate is 10%, the conversion rate is less than 25%.
Disclosure of Invention
In order to solve the problems of low conversion rate, solid waste generation and other pollution, harsh conversion conditions and the like of conversion and extraction of lactic acid in the post-treatment process of aqueous lactate solution, particularly fermentation liquor after lactic acid fermentation in the prior art, the invention provides a method for coupling the conversion and extraction of lactic acid from aqueous lactate raw material, which realizes the conversion and extraction of lactic acid simultaneously under relatively mild conditions and has higher conversion rate.
The technical purpose is realized by the following technical scheme:
a coupling method for converting lactic acid from a water-containing raw material of lactate and extracting the lactic acid comprises the steps of mixing the water-containing raw material of the lactate with an organic solvent, continuously introducing carbon dioxide into the mixed solution, reacting at a pressure of more than or equal to 7MPa and a temperature of more than or equal to 30 ℃, and separating an organic phase and a water phase after the reaction is finished, wherein the organic phase contains the lactic acid;
the organic solvent is an organic solvent which can dissolve lactic acid but is not completely dissolved with water, and is selected from at least one of esters, ethers and ketones with the C atom number being more than or equal to 5.
Further, in the above method, the organic solvent is at least one selected from the group consisting of methyl isobutyl ketone, diethyl ether and n-butyl acetate.
Further, in the above method, the aqueous raw material of lactate and the organic solvent are mixed in a weight ratio of 1:1-1:20, preferably 1:3-1:6.
further, in the above method, the lactate salt in the aqueous lactate salt material comprises 1% to 50%, preferably 2% to 30%, and most preferably 4% to 20% by weight of lactate.
Furthermore, in the method, after the carbon dioxide is introduced, the pressure is kept to be more than or equal to 7.29MPa, and the temperature is kept to be more than or equal to 31.26 ℃.
Further, in the above method, after the carbon dioxide is introduced, the pressure is maintained at 7.3 to 12MPa, preferably 7.3 to 10MPa.
Further, in the above method, after the introduction of carbon dioxide, the reaction temperature is maintained at 32 to 60 ℃, preferably 45 to 55 ℃.
Further, in the above method, the reaction time is 1 to 3 hours after the introduction of carbon dioxide.
In the above method, the organic phase and the aqueous phase are separated by allowing the reaction solution to stand for separation after the reaction is completed, and then reducing the pressure of carbon dioxide after the separation.
Further, in the above process, due to the different types of lactate in the raw material, after separation of the organic phase and the aqueous phase, a solid phase may also be present, for example, when the lactate is calcium lactate, calcium carbonate solids may be produced and may be reused in the lactic acid fermentation process.
Further, in the above method, the aqueous material of lactate is previously subjected to sterilization treatment.
In the above process, it will be understood by those skilled in the art that lactic acid in the aqueous feed of lactate salt, either in the form of free lactate ions or in undissociated form, may be used in the process of the present invention.
Compared with the prior art, the method has the following advantages:
(1) The method selects a mode of combining the organic solvent which can dissolve the lactic acid but is not completely miscible with water with the carbon dioxide high-pressure treatment, can simultaneously convert and extract the lactic acid from the water-containing raw material, and compared with the traditional sulfuric acid acidification method, the method uses the carbon dioxide to replace sulfuric acid as an acidifier, does not generate calcium sulfate solid waste, and is a green pollution-free separation method.
(2) For the existing lactic acid fermentation process, calcium carbonate is used for adjusting the pH value in the general fermentation liquid process, the lactic acid in the fermentation liquid generally exists in the form of calcium lactate, and after the conversion and extraction of the lactic acid are carried out by adopting the method disclosed by the invention, calcium carbonate solid is generated and can be reused in the fermentation process to realize the full utilization of the solid, so that the method cannot generate solid waste which is difficult to utilize and treat.
(3) Compared with the method only using carbon dioxide as an acidulant, the method has lower operation pressure and higher conversion rate, and the extraction and extraction of lactic acid are synchronously carried out, thereby simplifying the post-treatment process and having mild reaction conditions.
Additional features and advantages of the invention will be set forth in the detailed description which follows.
Detailed Description
The following describes the embodiments of the present invention in detail. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are given by way of illustration and explanation only, not limitation.
Example 1
Adding 100g of sterilized water-containing feed liquid containing calcium lactate into a reaction kettle, wherein the mass fraction of lactate in the water-containing feed liquid is 12%, adding 400g of organic solvent methyl isobutyl ketone, introducing carbon dioxide into the reaction kettle, pressurizing to 8MPa, heating to 50 ℃, keeping constant temperature and constant pressure, and fully stirring for reaction for 1.5h. And after the reaction is finished, standing and layering the reaction liquid, transferring the organic phase to a buffer tank which is pressurized to be equal to the pressure of the reaction kettle in advance through a lateral line pipeline of the reaction kettle at the height of a phase interface, separating inorganic phase, then cooling and depressurizing, recovering carbon dioxide, and dissolving lactic acid in the organic phase. And then separating lactic acid by a water phase back extraction method to obtain a lactic acid aqueous solution, measuring the content of the lactic acid by using liquid chromatography, and calculating the conversion rate.
Example 2
The conditions were the same as in example 1 except that the reaction temperature was changed to 60 ℃.
Example 3
The conditions were the same as in example 1 except that the reaction temperature was changed to 32 ℃.
Example 4
The conditions were the same as in example 3 except that the calcium lactate-containing aqueous feed solution was used in which the mass fraction of lactate was 4%.
Example 5
The conditions were the same as in example 3, except that an aqueous feed solution containing sodium lactate was used.
Example 6
The same conditions as in example 1 were used except that the organic solvent was changed to diethyl ether.
Example 7
The conditions were the same as in example 1 except that the organic solvent was changed to n-butyl acetate.
Example 8
The conditions were the same as in example 1 except that the reaction pressure was changed to 7.3 MPa.
Example 9
The conditions were the same as in example 1 except that the reaction pressure was changed to 10MPa.
Example 10
The reaction conditions were the same as in example 1 except that the reaction time was changed to 2.5 hours.
Example 11
The conditions were the same as in example 1 except that the reaction pressure was changed to 12 MPa.
Example 12
The conditions were the same as in example 1 except that the calcium lactate-containing aqueous feed solution was used in which the mass fraction of lactate was 16%.
Example 13
The conditions were the same as in example 1 except that the calcium lactate-containing aqueous feed solution was used in which the mass fraction of lactate was 20%.
Example 14
The conditions were the same as in example 1 except that the calcium lactate-containing aqueous feed liquid was used in which the mass fraction of lactate was 30%.
Example 15
The conditions were the same as in example 1 except that the mass ratio of the aqueous feed liquid to the organic solvent was 1.
Example 16
The conditions were the same as in example 1 except that the mass ratio of the aqueous feed liquid to the organic solvent was 1.
Comparative example 1
An aqueous solution of lactic acid was obtained after solid-liquid separation under the same operating conditions as in example 1 except that no organic solvent was added, and the conversion was calculated by measuring the lactic acid content by liquid chromatography.
The results of conversion of lactate in the above examples and comparative examples are shown in Table 1.
TABLE 1
The above non-limiting examples are intended to provide those of ordinary skill in the art with a more complete understanding of the present invention, and are not intended to limit the invention in any way.
Claims (9)
1. A method for coupling the conversion of lactic acid from water-containing raw material of lactate and the extraction of lactic acid is characterized in that the water-containing raw material of lactate is mixed with an organic solvent, then carbon dioxide is continuously introduced into the mixed solution, the reaction is carried out under the conditions that the pressure is kept between 7.3 and 12MPa and the reaction temperature is between 32 and 60 ℃, and after the reaction is finished, an organic phase and a water phase are separated, wherein the organic phase contains lactic acid;
the organic solvent is at least one selected from methyl isobutyl ketone, diethyl ether and n-butyl acetate.
2. The process according to claim 1, wherein the aqueous feed of lactate salt and organic solvent are present in a weight ratio of 1:1-1:20 and mixing.
3. The process according to claim 2, wherein the aqueous feed of lactate salt and organic solvent are present in a weight ratio of 1:3-1:6 and mixing.
4. The method as claimed in claim 1, wherein the aqueous source of lactate salt comprises from 1% to 50% by weight lactate salt, based on the weight of lactate.
5. The method as claimed in claim 4, wherein the lactate salt comprises from 2% to 30% by weight of lactate in the aqueous lactate salt stock.
6. The method according to claim 1, wherein the pressure is maintained at 7.3 to 10MPa after the introduction of the carbon dioxide.
7. The process as claimed in claim 1, wherein the reaction temperature is maintained at 45-55 ℃ after the introduction of the carbon dioxide.
8. The method of claim 1, wherein the reaction time is 1 to 3 hours after the carbon dioxide is introduced.
9. The method according to claim 1, wherein the organic phase and the aqueous phase are separated by allowing the reaction solution to stand for separation after the reaction is completed, and then reducing the pressure of carbon dioxide after the separation.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911048850.8A CN112745215B (en) | 2019-10-31 | 2019-10-31 | Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201911048850.8A CN112745215B (en) | 2019-10-31 | 2019-10-31 | Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112745215A CN112745215A (en) | 2021-05-04 |
| CN112745215B true CN112745215B (en) | 2022-11-11 |
Family
ID=75641085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201911048850.8A Active CN112745215B (en) | 2019-10-31 | 2019-10-31 | Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112745215B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510526A (en) * | 1993-06-29 | 1996-04-23 | Cargill, Incorporated | Lactic acid production, separation and/or recovery process |
| CN1407962A (en) * | 1999-10-12 | 2003-04-02 | 普拉克生化公司 | Continuous process for preparing lactic acid |
| CN1938257A (en) * | 2004-01-29 | 2007-03-28 | 齐凯姆公司 | Recovery of organic acids |
| CN103998108A (en) * | 2011-12-23 | 2014-08-20 | 普拉克生化公司 | Lactic acid extraction |
| CN107324989A (en) * | 2017-06-09 | 2017-11-07 | 安徽丰原发酵技术工程研究有限公司 | It is a kind of by being dehydrated the method that extraction prepares lactic acid and lactide |
| CN109678696A (en) * | 2019-01-31 | 2019-04-26 | 华熙福瑞达生物医药有限公司 | A method of extracting lactic acid from hyaluronic acid fermentation liquor |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL119387A (en) * | 1996-10-09 | 2001-06-14 | Cargill Inc | Process for the recovery of lactic acid by liquid-liquid extraction with a basic extractant |
-
2019
- 2019-10-31 CN CN201911048850.8A patent/CN112745215B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5510526A (en) * | 1993-06-29 | 1996-04-23 | Cargill, Incorporated | Lactic acid production, separation and/or recovery process |
| CN1407962A (en) * | 1999-10-12 | 2003-04-02 | 普拉克生化公司 | Continuous process for preparing lactic acid |
| CN1938257A (en) * | 2004-01-29 | 2007-03-28 | 齐凯姆公司 | Recovery of organic acids |
| CN103998108A (en) * | 2011-12-23 | 2014-08-20 | 普拉克生化公司 | Lactic acid extraction |
| CN107324989A (en) * | 2017-06-09 | 2017-11-07 | 安徽丰原发酵技术工程研究有限公司 | It is a kind of by being dehydrated the method that extraction prepares lactic acid and lactide |
| CN109678696A (en) * | 2019-01-31 | 2019-04-26 | 华熙福瑞达生物医药有限公司 | A method of extracting lactic acid from hyaluronic acid fermentation liquor |
Non-Patent Citations (1)
| Title |
|---|
| L-乳酸的发酵生产和聚L-乳酸的化学加工;田康明等;《中国生物工程杂志》;20110215(第02期);102-115 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112745215A (en) | 2021-05-04 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Mores et al. | Citric acid bioproduction and downstream processing: Status, opportunities, and challenges | |
| Boonmee et al. | Improved lactic acid production by in situ removal of lactic acid during fermentation and a proposed scheme for its recovery | |
| CN106083951B (en) | A method of utilizing kasugarnycin broth extraction kasugamycini hydrochloride | |
| CN106755143B (en) | Method for continuously extracting high-purity lactic acid from lactic acid fermentation liquor | |
| CN104445276A (en) | Method for efficiently preparing monocyanamide solution | |
| CN110845326A (en) | Method for preparing lactic acid and lactide by dehydration extraction | |
| WO2023116302A1 (en) | Method for co-producing erythritol and arabinose from xylose mother liquor | |
| CN108047175B (en) | A kind of synthetic method of furanone | |
| CN111574358A (en) | Preparation process of potassium diformate | |
| CN106117038B (en) | A kind of technique that calcium lactate is produced using nisin waste water | |
| CN114149351A (en) | Methionine optimized preparation method based on sulfuric acid direct acidification method and sodium sulfate washing equipment | |
| CN112745215B (en) | Coupling method for converting lactic acid and extracting lactic acid from aqueous lactate raw material | |
| CN110669797A (en) | Method for producing long-chain dicarboxylic acid by fermentation | |
| CN103420826A (en) | Method for extracting succinic acid from fermentation broth | |
| CN102875432B (en) | Preparation method of high-yield tiamulinfumarate | |
| CN103804173B (en) | A kind of process for purification of fermentation organic acid | |
| KR101952060B1 (en) | Method for preparing furan-2,5-dicarboxylic acid (FDCA) from solid salt | |
| CN105084657B (en) | Methionine produces the Biochemical pretreatment method of waste water | |
| CN106117292A (en) | A kind of separation vitamin B12 and method of propanoic acid from fermentation liquid | |
| CN106220513B (en) | A method of preparing nonamethylene diamine | |
| CN110698439B (en) | Process for preparing D-pantolactone by bipolar membrane method | |
| CN101103805B (en) | Industrial producing method for extracting fatty compound from melissa pollen | |
| CN113121329B (en) | Method for coupling conversion and extraction of lactic acid from aqueous lactate raw material | |
| CN105483165A (en) | Preparation method of L-malic acid | |
| CN106554279B (en) | A method of extracting succinate from succinic acid fermentation liquor |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20231113 Address after: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Patentee after: CHINA PETROLEUM & CHEMICAL Corp. Patentee after: Sinopec (Dalian) Petrochemical Research Institute Co.,Ltd. Address before: 100728 No. 22 North Main Street, Chaoyang District, Beijing, Chaoyangmen Patentee before: CHINA PETROLEUM & CHEMICAL Corp. Patentee before: DALIAN RESEARCH INSTITUTE OF PETROLEUM AND PETROCHEMICALS, SINOPEC Corp. |