CN114736115A - Method for extracting and separating succinic acid and succinate in aqueous solution - Google Patents
Method for extracting and separating succinic acid and succinate in aqueous solution Download PDFInfo
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- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 title claims abstract description 158
- 239000001384 succinic acid Substances 0.000 title claims abstract description 78
- 238000000034 method Methods 0.000 title claims abstract description 31
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 title claims abstract description 23
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 20
- 238000000605 extraction Methods 0.000 claims abstract description 109
- 239000012074 organic phase Substances 0.000 claims abstract description 40
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 18
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- TVQGDYNRXLTQAP-UHFFFAOYSA-N ethyl heptanoate Chemical compound CCCCCCC(=O)OCC TVQGDYNRXLTQAP-UHFFFAOYSA-N 0.000 claims abstract description 14
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims abstract description 12
- UXUPPWPIGVTVQI-UHFFFAOYSA-N isobutyl hexanoate Chemical compound CCCCCC(=O)OCC(C)C UXUPPWPIGVTVQI-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000005406 washing Methods 0.000 claims abstract description 11
- 150000001298 alcohols Chemical class 0.000 claims abstract description 10
- 150000002148 esters Chemical class 0.000 claims abstract description 10
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- 238000000926 separation method Methods 0.000 claims abstract description 9
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims abstract description 7
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims abstract description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims abstract description 6
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims abstract description 6
- XTVHTJKQKUOEQA-UHFFFAOYSA-N heptane-2,5-diol Chemical compound CCC(O)CCC(C)O XTVHTJKQKUOEQA-UHFFFAOYSA-N 0.000 claims abstract description 6
- YTHTWWXHLQCJRN-UHFFFAOYSA-N n,n-dioctylbutanamide Chemical compound CCCCCCCCN(C(=O)CCC)CCCCCCCC YTHTWWXHLQCJRN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229940065472 octyl acrylate Drugs 0.000 claims abstract description 6
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 229950001902 dimevamide Drugs 0.000 claims abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 239000012071 phase Substances 0.000 claims description 8
- 238000000855 fermentation Methods 0.000 claims description 6
- 230000004151 fermentation Effects 0.000 claims description 6
- 150000003890 succinate salts Chemical class 0.000 claims 1
- 230000008569 process Effects 0.000 abstract description 5
- 238000005265 energy consumption Methods 0.000 abstract description 3
- 238000003912 environmental pollution Methods 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- 239000012535 impurity Substances 0.000 description 11
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 8
- 238000000909 electrodialysis Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 239000012528 membrane Substances 0.000 description 5
- 235000011132 calcium sulphate Nutrition 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical group O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 3
- 239000000920 calcium hydroxide Substances 0.000 description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 3
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 3
- 239000000292 calcium oxide Substances 0.000 description 3
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 3
- PBUBJNYXWIDFMU-UHFFFAOYSA-L calcium;butanedioate Chemical compound [Ca+2].[O-]C(=O)CCC([O-])=O PBUBJNYXWIDFMU-UHFFFAOYSA-L 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 229940074404 sodium succinate Drugs 0.000 description 3
- ZDQYSKICYIVCPN-UHFFFAOYSA-L sodium succinate (anhydrous) Chemical compound [Na+].[Na+].[O-]C(=O)CCC([O-])=O ZDQYSKICYIVCPN-UHFFFAOYSA-L 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000001175 calcium sulphate Substances 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000003607 modifier Substances 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000004631 polybutylene succinate Substances 0.000 description 2
- 229920002961 polybutylene succinate Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- -1 vitamin a Substances 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- GUOCOOQWZHQBJI-UHFFFAOYSA-N 4-oct-7-enoxy-4-oxobutanoic acid Chemical compound OC(=O)CCC(=O)OCCCCCCC=C GUOCOOQWZHQBJI-UHFFFAOYSA-N 0.000 description 1
- 206010010071 Coma Diseases 0.000 description 1
- 208000035240 Disease Resistance Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000237509 Patinopecten sp. Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 239000003674 animal food additive Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 229940124350 antibacterial drug Drugs 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940030225 antihemorrhagics Drugs 0.000 description 1
- NHJPVZLSLOHJDM-UHFFFAOYSA-N azane;butanedioic acid Chemical compound [NH4+].[NH4+].[O-]C(=O)CCC([O-])=O NHJPVZLSLOHJDM-UHFFFAOYSA-N 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000015895 biscuits Nutrition 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 150000001887 cortisones Chemical class 0.000 description 1
- 229920006238 degradable plastic Polymers 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- NSYZCCDSJNWWJL-YXOIYICCSA-N erythromycin ethylsuccinate Chemical compound O1[C@H](C)C[C@H](N(C)C)[C@@H](OC(=O)CCC(=O)OCC)[C@@H]1O[C@H]1[C@@](O)(C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](CC)OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(OC)C2)[C@@H]1C NSYZCCDSJNWWJL-YXOIYICCSA-N 0.000 description 1
- 229960000741 erythromycin ethylsuccinate Drugs 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 239000002874 hemostatic agent Substances 0.000 description 1
- 230000002439 hemostatic effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 230000036039 immunity Effects 0.000 description 1
- 235000008446 instant noodles Nutrition 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 210000000663 muscle cell Anatomy 0.000 description 1
- RBMVCCBFSZZWLF-UHFFFAOYSA-N n,n-dipropylpentanamide Chemical compound CCCCC(=O)N(CCC)CCC RBMVCCBFSZZWLF-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 235000013324 preserved food Nutrition 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 235000013580 sausages Nutrition 0.000 description 1
- 235000020637 scallop Nutrition 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 230000004102 tricarboxylic acid cycle Effects 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 235000013618 yogurt Nutrition 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
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/48—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to and discloses an extraction separation method of succinic acid and succinate in aqueous solution, which comprises the following extraction steps (I): (i) an extraction separation method for extracting succinic acid and succinate in an aqueous solution by using an organic phase is adopted, the used extracting agent is one or more of alcohols, esters or amines, and the alcohols are one or more of glycerol, dimethyl ethyl methanol and 2, 5-heptanediol; the amine is one or more of diethylamine, cyclohexylamine and tripropylamine; the esters are one or more of octyl acrylate, ethyl heptanoate and isobutyl hexanoate; the amide is N, N-dimethylacetamide, N-dipropyl valeramide and N, N-dioctyl butyramide; the ketone is methyl ethyl ketone; (ii) after sufficient reaction, the loaded organic phase and raffinate were separated. The succinic acid with higher purity is obtained through extraction, washing and back extraction. The invention has mild process conditions, little environmental pollution, high productivity and low energy consumption, and is suitable for industrial production.
Description
Technical Field
The invention relates to an extraction separation method of succinic acid and succinate in an aqueous solution.
Background
The application field of the succinic acid is very wide, the succinic acid is colorless crystal, is an important organic acid and widely exists in human bodies, animals, plants and microorganisms; it is also a common C4 dicarboxylic acid, an important intermediate product in the Krebs cycle, and one of the 12 most potential platform compounds identified by the U.S. department of energy. The succinic acid can be used for synthesizing intermediates of various complex organic matters and manufacturing medicaments, is widely applied to various fields of chemical industry, pesticides, foods, medicines, synthetic plastics and the like, and is mainly used for synthesizing 1, 4-butanediol, gamma-butyrolactone and tetrahydrofuran in the chemical industry. In agriculture, succinic acid is a plant growth regulator to stimulate crop growth, regulate nutrients, increase disease resistance, drought resistance and freezing resistance, generally increase yield by 10-20%, and can also be used as an additive for treating barley smut and herbicides and as a feed additive. In the food field, succinic acid is mainly used as a flavoring agent, an enhancer, a flavor modifier, an emulsifier, and the like, such as: the sodium salt of succinic acid (scallop extract) has unique delicate flavor, and can be used as flavoring agent for improving the flavor of bean paste, soy sauce, liquid flavoring, vegetarian food, etc., as reinforcing agent for milk slice, biscuit, and milk powder, for promoting growth, and as flavor modifier for beer, ham, sausage, pickles, instant noodles, meat can, etc. Starch octenyl succinate is derivative of succinic acid, and can be used as high-safety emulsifying thickener for processing canned food, cheese, yogurt, powder essence, soft beverage, etc. In the pharmaceutical industry, succinic acid can be used for the synthesis of drugs such as vitamin a, antibiotics, cortisone derivatives, diuretics, tranquilizers, and hemostatics, for example: sodium succinate can be used for treating coma, ammonium succinate can be used as sedative, succinate has anticancer, health promotion and immunity regulating effects, and can improve nutrition supply of human body, make muscle cells more easily absorb nutrient substances, succinate has detoxification effect on barbiturate drug poisoning, and erythromycin ethylsuccinate is also called as lincoman and is a common oral antibacterial drug. The succinic acid has more development prospect, is in the degradable plastic industry, and is a main raw material for synthesizing polybutylene succinate (PBS).
The succinic acid has extremely important application and large domestic demand, so the extraction and separation method for separating and purifying the succinic acid and the succinate from an aqueous solution has important significance.
Patent US5168055 discloses the separation of succinic acid from succinic acid fermentation broth using a calcium salt process, in which calcium hydroxide or calcium oxide is used to obtain calcium succinate. Filtering to obtain mixed precipitate of calcium succinate, thallus and protein, and washing to remove impurities such as thallus and protein; acidifying the washed calcium succinate with concentrated sulfuric acid to obtain succinic acid and a byproduct calcium sulfate; filtering to remove calcium sulfate, removing impurities from the succinic acid solution through ion exchange resin, and finally concentrating and crystallizing to obtain succinic acid crystals with the purity of 80-99%. In this way, succinic acid crystals are difficult to obtain and the yield is low. It has been found that the main drawbacks of using calcium hydroxide or calcium oxide for precipitation are the high content of calcium sulphate by-product, the increased cost of disposing of the calcium sulphate by-product, and the inability to use it for commercial production due to problems of odour and colour impurities generated during fermentation; another problem is that reagents such as calcium hydroxide, calcium oxide and sulfuric acid are consumed and cannot be recovered or regenerated in the process, resulting in high processing costs.
Patent US5143834 adopts electrodialysis desalination method and bipolar membrane electrodialysis method to extract succinic acid from fermentation broth. The first step of the desalting electrodialysis process is to use uncharged substances, such as weak acids, residual sugars and proteins, which cannot pass through the cell membrane, and pass all charged ions through the cell membrane (such as sodium succinate) and separate them from succinic acid, in which process the succinic acid loss is about 23%; and the second step is to convert the sodium succinate in the first step into succinic acid and sodium hydroxide through bipolar membrane electrodialysis, and the sodium hydroxide can be recycled for adjusting the pH value in the succinic acid fermentation process. After two electrodialysis, the yield of succinic acid was 60%. The disadvantages of electrodialysis are high energy consumption, low membrane material cost and low succinic acid selectivity. Yet another problem is the presence of binary ions which the electrodialysis membranes cannot solve.
At present, the succinic acid is mainly separated and purified by a calcium salt method, an ammonium salt method, an ion exchange method, an electrodialysis method, a membrane separation method and the like. However, these methods are expensive and cause serious environmental pollution, and thus are not suitable for mass production. Therefore, it is necessary to develop a separation method which is simple in operation, low in cost and high in recovery rate.
Disclosure of Invention
The invention aims to provide a method for extracting and separating succinic acid and succinate in an aqueous solution, so as to solve the problems in the background technology.
In order to solve the technical problems, the technical scheme provided by the invention is as follows: the extraction and separation method of succinic acid and succinate in an aqueous solution is characterized by comprising the following steps of:
and (3) extraction: extracting succinic acid and succinate in the aqueous solution by using an organic phase extracting agent, wherein the organic phase extracting agent is one or more of alcohols, esters, amines and ketones, and the alcohols are one or more of glycerol, dimethyl ethyl methanol and 2, 5-heptanediol; the amine is one or more of diethylamine, cyclohexylamine and tripropylamine; the esters are one or more of octyl acrylate, ethyl heptanoate and isobutyl hexanoate; the amines are N, N-dimethylacetamide, N-dipropylpentanamide and N, N-dioctylbutanamide; the ketone is methyl ethyl ketone; after sufficient reaction, the loaded organic phase was separated from the raffinate.
Preferably, the phase ratio during extraction is between 0.1:1 and 10: 1.
More preferably, the phase ratio during extraction is 1.5:1 to 4: 1.
Preferably, the extraction step is countercurrent extraction, the extraction stage number is more than 1 stage, the extraction time is not less than 1min, and the extraction temperature is 20-80 ℃.
Preferably, the method further comprises the following steps: back extraction: back extracting the succinic acid in the loaded organic phase by using a back extractant, wherein the back extractant is water; after sufficient reaction, the loaded organic phase is separated from the stripping agent.
Preferably, the extraction process is countercurrent extraction, the number of countercurrent extraction stages is not less than 1 stage, the extraction time is not less than 1min, the extraction temperature is 20-80 ℃, and the extraction phase ratio is 0.1:1-10: 1; the back extraction step is counter-current back extraction, the number of counter-current back extraction stages is not less than 1 stage, the back extraction time is not less than 1min, the back extraction temperature is 30-80 ℃, and the phase ratio in the back extraction step is as follows: 0.5:1-10:1.
More preferably, the phase ratio of the extractions is from 1.5:1 to 4: 1; the phase ratio in the back extraction step is as follows: 4:1-8:1.
More preferably, the method further comprises the following steps: countercurrent extraction: extracting succinic acid in fermentation liquor by using organic phase countercurrent to obtain a loaded organic phase and raffinate, wherein the used organic phase extracting agent is one or more of alcohols, esters, amines and ketones, and the alcohols are one or more of glycerol, dimethyl ethyl methanol and 2, 5-heptanediol; the amine is one or more of diethylamine, cyclohexylamine and tripropylamine; the esters are one or more of octyl acrylate, ethyl heptanoate and isobutyl hexanoate; the amines are N, N-dimethylacetamide, N-dipropylpentanamide and N, N-dioctylbutanamide; the ketone is methyl ethyl ketone; the loaded organic phase enters a countercurrent pickling and back extraction process section, and the loaded organic phase is back extracted by water.
Preferably, the ratio of the extraction steps is 1.5:1-4:1, the number of countercurrent extraction stages is more than or equal to 4, the extraction time is 2-10min, and the extraction temperature is 40-50 ℃; the back extraction step comprises: the ratio is 4:1-8:1, the counter-current back-extraction stage number is more than or equal to 5, the back-extraction time is 2-10min, and the back-extraction temperature is 60-70 ℃.
The invention has the advantages that: mild technological conditions, less environmental pollution, high productivity, low energy consumption and suitability for industrial production.
Detailed Description
The invention is illustrated below by means of specific examples, without being restricted thereto.
Example 1
The present example is directed to a succinic acid and succinate solution in an aqueous solution that contains a small amount of organic acids as impurities in addition to a large amount of succinic acid. Extracting succinic acid by using 60% (V/V, volume fraction) diethylamine, 20% (V/V, volume fraction) glycerol and 20% (V/V, volume fraction) octyl acrylate as an extraction system, wherein the volume ratio of the three is 6:2:2, the extraction rate of the succinic acid is 20.89% when the ratio is 2, and the extraction rate of the succinic acid can reach 50.69% when the ratio is continuously increased to 4.5, and the extraction rate of 9-level countercurrent extraction on the succinic acid can reach 98.42%, so as to obtain a loaded organic phase; carrying out acid washing on the loaded organic phase to obtain an organic phase which is washed and does not contain impurities; and finally, performing back extraction by using deionized water to obtain succinic acid solution with the purity of 99.25 percent.
Example 2
This example is directed to a succinic acid solution. Extracting succinic acid by using 70% (V/V, volume fraction) cyclohexylamine and 30% (V/V, volume fraction) 2, 5-heptanediol as an extraction system, wherein the succinic acid has a volume ratio of 7:3, compared with 2.5, the extraction rate of the succinic acid is 52.32%, and the extraction rate of 8-stage countercurrent extraction on the succinic acid can reach 98.56%, so as to obtain a loaded organic phase; carrying out acid washing on the loaded organic phase to obtain an organic phase which does not contain impurities after washing; and finally, performing back extraction by using deionized water to obtain succinic acid solution with the purity of 99.12 percent.
Example 3
The present example is directed to a succinate solution. Extracting succinic acid by using 80% (V/V, volume fraction) of N, N-dipropyl valeramide and 20% (V/V, volume fraction) of methyl ethyl ketone as an extraction system, wherein the volume ratio of the two is 8:2, and the ratio is 2.5, so that the extraction rate of the succinic acid is 50.26%, and the extraction rate of 9-stage countercurrent extraction on the succinic acid can reach 97.88%, thereby obtaining a loaded organic phase; carrying out acid washing on the loaded organic phase to obtain an organic phase which does not contain impurities after washing; and finally, performing back extraction by using deionized water to obtain a succinic acid solution with the purity of 99.16%.
Example 4
This example is directed to a succinic acid and succinate solution. Using 60% (V/V, volume fraction) N, N-dioctyl butanamide and 40% (V/V, volume fraction) dimethyl ethyl methanol as an extraction system to extract succinic acid, wherein the volume ratio of the two is 6:4, the ratio is 2, the extraction rate of the succinic acid is 48.97%, and the extraction rate of 9-grade countercurrent extraction on the succinic acid can reach 98.35%, so as to obtain a loaded organic phase; carrying out acid washing on the loaded organic phase to obtain an organic phase which is washed and does not contain impurities; and finally, performing back extraction by using deionized water to obtain succinic acid solution with the purity of 99.19 percent.
Example 5
The present example is directed to a succinic acid solution that contains a small amount of organic acids as impurities in addition to a large amount of succinic acid. Extracting succinic acid by using 50% (V/V, volume fraction) tripropylamine and 50% (V/V, volume fraction) ethyl heptanoate as an extraction system, wherein the volume ratio of the tripropylamine to the ethyl heptanoate is 5:5, the extraction rate of the succinic acid is 53.47% compared with 2, the extraction rate of the succinic acid by 8-grade countercurrent extraction can reach 98.87%, and a loaded organic phase is obtained; carrying out acid washing on the loaded organic phase to obtain an organic phase which is washed and does not contain impurities; and finally, performing back extraction by using deionized water to obtain succinic acid solution with the purity of 99.01 percent.
Example 6
This example is directed to a succinic acid solution. Extracting succinic acid by using 90% (V/V, volume fraction) N, N-dimethylacetamide and 10% (V/V, volume fraction) isobutyl caproate as an extraction system, wherein the volume ratio of the two is 9:1, and compared with 2, the extraction rate of the succinic acid is 52.36%, and the extraction rate of 8-level countercurrent extraction on the succinic acid can reach 98.66%, so as to obtain a loaded organic phase; carrying out acid washing on the loaded organic phase to obtain an organic phase which is washed and does not contain impurities; and finally, performing back extraction by using deionized water to obtain succinic acid solution with the purity of 99.23%.
It should be understood that the above-mentioned embodiments of the present invention are only examples for clearly illustrating the present invention, and are not intended to limit the embodiments of the present invention, and it will be obvious to those skilled in the art that other variations or modifications may be made on the basis of the above description, and all embodiments may not be exhaustive, and all obvious variations or modifications may be included within the scope of the present invention.
Claims (9)
1. The extraction and separation method of succinic acid and succinate in an aqueous solution is characterized by comprising the following steps of:
and (3) extraction: extracting succinic acid and succinate in the aqueous solution by using an organic phase extracting agent, wherein the organic phase extracting agent is one or more of alcohols, esters, amines and ketones, and the alcohols are one or more of glycerol, dimethyl ethyl methanol and 2, 5-heptanediol; the amine is one or more of diethylamine, cyclohexylamine and tripropylamine; the esters are one or more of octyl acrylate, ethyl heptanoate and isobutyl hexanoate; the amines are N, N-dimethylacetamide, N-dipropyl valeramide and N, N-dioctyl butyramide; the ketone is methyl ethyl ketone; after sufficient reaction, the loaded organic phase was separated from the raffinate.
2. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 1, wherein the method comprises the following steps: the ratio in the extraction process is 0.1:1-10: 1.
3. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 2, wherein the method comprises the following steps: the ratio in the extraction process is 1.5:1-4: 1.
4. The method for extracting and separating succinic acid and succinate from an aqueous solution according to any one of claims 1 to 3, wherein the method comprises the following steps: the extraction step is countercurrent extraction, the extraction stage number is more than 1 stage, the extraction time is not less than 1min, and the extraction temperature is 20-80 ℃.
5. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 1, further comprising the following steps: back extraction: back extracting the succinic acid in the loaded organic phase by using a back extractant, wherein the back extractant is water; after sufficient reaction, the loaded organic phase is separated from the stripping agent.
6. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 5, wherein the method comprises the following steps: the extraction process is countercurrent extraction, the stage number of the countercurrent extraction is not less than 1, the extraction time is not less than 1min, the extraction temperature is 20-80 ℃, and the extraction ratio is 0.1:1-10: 1; the back extraction step is counter-current back extraction, the number of counter-current back extraction stages is not less than 1 stage, the back extraction time is not less than 1min, the back extraction temperature is 30-80 ℃, and the phase ratio in the back extraction step is as follows: 0.5:1-10:1.
7. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 6, wherein the method comprises the following steps: the extraction ratio is 1.5:1-4: 1; the phase ratio in the back extraction step is as follows: 4:1-8:1.
8. The method for extracting and separating succinic acid and succinate salt from aqueous solution according to claim 5, further comprising the following steps: countercurrent extraction: extracting succinic acid in fermentation liquor by using organic phase countercurrent to obtain a loaded organic phase and raffinate, wherein the used organic phase extracting agent is one or more of alcohols, esters, amines and ketones, and the alcohols are one or more of glycerol, dimethyl ethyl methanol and 2, 5-heptanediol; the amine is one or more of diethylamine, cyclohexylamine and tripropylamine; the esters are one or more of octyl acrylate, ethyl heptanoate and isobutyl hexanoate; the amines are N, N-dimethylacetamide, N-dipropylpentanamide and N, N-dioctylbutanamide; the ketone is methyl ethyl ketone; the loaded organic phase enters a countercurrent acid washing and back extraction process section, and the loaded organic phase is back extracted by water.
9. The method for extracting and separating succinic acid and succinate from an aqueous solution according to claim 8, wherein the method comprises the following steps: the ratio of the extraction step to the counter-current extraction step is 1.5:1-4:1, the number of stages of counter-current extraction is more than or equal to 4, the extraction time is 2-10min, and the extraction temperature is 40-50 ℃; the back extraction step comprises: the ratio of the counter current back extraction stage number to the counter current back extraction stage number is 4:1-8:1, the counter current back extraction stage number is more than or equal to 5, the back extraction time is 2-10min, and the back extraction temperature is 60-70 ℃.
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