CN110204437A - A method of producing L MALIC ACID coproduction succinic acid - Google Patents
A method of producing L MALIC ACID coproduction succinic acid Download PDFInfo
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- CN110204437A CN110204437A CN201910590995.4A CN201910590995A CN110204437A CN 110204437 A CN110204437 A CN 110204437A CN 201910590995 A CN201910590995 A CN 201910590995A CN 110204437 A CN110204437 A CN 110204437A
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- 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
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Abstract
The present invention provides a kind of method for producing L MALIC ACID coproduction succinic acid, this method is using fermentation method or the enzyme transforming process production resulting fermentation liquid containing L MALIC ACID calcium and calcium succinate of L MALIC ACID as raw material, it is separated by solid-liquid separation, respectively obtains the solid of calcium containing L MALIC ACID and calcium succinate and the liquid of calcium containing L MALIC ACID and calcium succinate；After carrying out multi-step processing using acid hydrolysis method to the solid, L MALIC ACID product can be obtained；After carrying out multi-step processing using ion exchange resin to the liquid, succinic acid product can be obtained.Method provided by the invention realizes L MALIC ACID and succinic acid separation in fermentation liquid, while the yield of L MALIC ACID and succinic acid is greatly improved.It is high-quality by the obtained L MALIC ACID of this method and succinic acid purity is high.
Description
Technical field
The present invention relates to field of food chemical industry, and in particular to a method of produce L MALIC ACID coproduction succinic acid.
Background technique
Malic acid also known as 2- hydroxysuccinic acid, due to there is an asymmetric carbon atom in molecule, there are two types of alloisomerisms
Body.In the Nature, exist in the form of three kinds, i.e. D-malic acid, L MALIC ACID and its mixture D L MALIC ACID.Malic acid is white
Color crystalline solid or crystalline powder have stronger hygroscopicity, soluble easily in water, ethyl alcohol.There is special pleasant tart flavour.L MALIC ACID master
It is used for food and medicine industry.
Succinic acid also known as amber platinic acid are colourless crystallization, are dissolved in water, are slightly soluble in ethyl alcohol, ether and acetone.Industrially, Chang You
Butene dioic acid catalysis reduction is made, and can also be hydrolyzed and be prepared by succinonitrile.Fermentation method production succinic acid also obtains application.Fermentation method
The succinic acid conventional extraction of production has calcium salt method and extraction etc..
Malic acid production method has chemical synthesis, fermentation method and enzymatic production process at present.Chemical synthesis investment is big,
Technical requirements are high, and the product of synthesis is DL-malic acid.L- is extracted from malic acid fermentation liquid prepared by fermentation method and enzyme transforming process
The common method of malic acid has acidolysis ion-exchange method and organic solvent extractionprocess.Existing acid dissociation is handed over skill, and product purity is low, receives
Rate is low.The problems such as there are it to be stripped difficulty for conventional organic solvent extraction, and product purity is low, dissolvent residual.And this field still lacks
The method that weary one kind can efficiently produce L MALIC ACID coproduction succinic acid.
Summary of the invention
Method provided by the invention obtains the fermentation liquid containing L MALIC ACID calcium and calcium succinate for fermentation method, proposes
It is a kind of to recycle L MALIC ACID calcium and fourth two using calcium salt method separation and Extraction L MALIC ACID and succinic acid and by resin adsorption method
The method of L MALIC ACID and succinic acid in sour mother liquor of calcium.The present invention realizes L MALIC ACID and succinic acid separation in fermentation liquid,
Simultaneously the yield of L MALIC ACID and succinic acid is greatly improved.Pass through the obtained L MALIC ACID of this method and succinic acid purity
Height, it is high-quality.
Specifically, method provided by the invention includes the following steps:
The resulting fermentation liquid containing L MALIC ACID calcium and calcium succinate of L MALIC ACID is produced with fermentation method or enzyme transforming process
For raw material, it is separated by solid-liquid separation, obtains the solid of calcium containing L MALIC ACID and calcium succinate and the liquid of calcium containing L MALIC ACID and calcium succinate
Body；
The processing that the solid of the calcium containing L MALIC ACID and calcium succinate is included the following steps:
(1) solid is subjected to acidolysis, be separated by solid-liquid separation, abandon calcium sulphate solid, collected and contain L MALIC ACID hydrogen calcium and fourth
The mixed solution of diacid hydrogen calcium；The L MALIC ACID hydrogen calcium in the mixed solution is crystallized, L MALIC ACID hydrogen calcium crystal is collected；
(2) the L MALIC ACID hydrogen calcium crystal is subjected to further acidolysis, be separated by solid-liquid separation, abandoned calcium sulphate solid, obtain L-
Malic acid acid hydrolysis solution；
(3) the L MALIC ACID acid hydrolysis solution is refined, obtains L MALIC ACID product；
The processing that the liquid of the calcium containing L MALIC ACID and calcium succinate is included the following steps:
(i) liquid is passed through cation exchange resin, removal cation obtains decationizing solution；
(ii) the decationizing solution is passed through anion exchange resin, sufficiently adsorbed, then eluted with dilute sulfuric acid,
The eluent of L MALIC ACID and succinic acid must be contained；The succinic acid in the eluent is crystallized, succinic acid coarse crystal is collected；
(iii) the succinic acid coarse crystal is refined, obtains succinic acid product.
Raw material used by method provided by the invention, to produce L- apple using this field normal fermentation method or enzymatic conversion
The resulting fermentation liquid of acid.In general, in the fermentation liquid containing a large amount of calcium malate and calcium succinate (calcium succinate
Concentration can be larger, can also be micro), and the impurity such as a large amount of sugar, protein.Malic acid of the present invention refers to L- apple
Acid.
Method provided by the invention will carry out solid-liquid point containing the fermentation liquid raw material of L MALIC ACID calcium and calcium succinate first
From obtaining the solid of calcium containing L MALIC ACID and calcium succinate and liquid two parts containing L MALIC ACID calcium and calcium succinate.
In order to be sufficiently separated solid-liquid two parts, and target substance is enriched with respectively in two-phase, the preferably described separation of solid and liquid of the present invention
Temperature is 10~100 DEG C, more preferably 70~80 DEG C.
For the solid of calcium containing L MALIC ACID and calcium succinate, the present invention is handled by the way of acidolysis conversion through multi-step
The L MALIC ACID calcium of high-purity is obtained, specifically:
In the step (1), obtained solid portion is added water to size mixing or adds the part that generates in production process by the present invention
L MALIC ACID hydrogen calcium and succinic acid hydrogen mother liquor of calcium are sized mixing, concentration of sizing mixing 10~70%.By the way that sulfuric acid or L- apple is added after sizing mixing
The pH value of the mother liquor adjusting slurry containing L MALIC ACID and a small amount of succinic acid obtained after acid mother liquor or separation succinic acid is 1.5~4.5,
Preferably pH2.0~4.0 carry out acidolysis.The reaction temperature of acidolysis is preferably 10~100 DEG C, is more preferably heated to 70~90
℃.Acidolysis obtains calcium sulphate solid and the mixture containing L MALIC ACID hydrogen calcium and succinic acid hydrogen calcium, is separated by solid-liquid separation (as filtered)
Remove solid calcium sulphate.The liquid of the gained calcium of hydrogen containing L MALIC ACID and succinic acid hydrogen calcium is concentrated after calcium sulphate solid will be removed
Crystallization and/or decrease temperature crystalline, preferably control temperature are crystallized at 5~15 DEG C, crystallize out L MALIC ACID hydrogen calcium from liquid.
For the percent crystallization in massecuite for improving L MALIC ACID hydrogen calcium, crystallization process can also be suitably added the substances such as calcium carbonate, calcium oxide, calcium hydroxide
Improve percent crystallization in massecuite.The isolated more pure L MALIC ACID hydrogen calcium of the magma of obtained hydrogen containing L MALIC ACID calcium crystal is consolidated
Body and mother liquor containing L MALIC ACID hydrogen calcium and succinic acid hydrogen calcium.The mother liquor can return and L MALIC ACID calcium and succinic acid
The mixing of calcium fermentation liquid or part are for sizing mixing containing L MALIC ACID calcium and calcium succinate solid described in this step.
In the step (2), add water to size mixing the pure L MALIC ACID hydrogen calcium solid of gained, sulfuric acid solution is added to reaction
Terminal, i.e. L MALIC ACID hydrogen calcium are completely converted into calcium malate.The acidolysis temperature is preferably 20~100 DEG C, and terminal pH is preferred
It is 1.5~2.2.It is separated by solid-liquid separation and removes calcium sulfate, available purer L MALIC ACID acid hydrolysis solution.
In the step (3), the L MALIC ACID acid hydrolysis solution is refined using conventional method, obtains finished product L- apple
Acid.Such as handled with means such as decoloration, cationic exchange, anion exchanges, obtain pure L MALIC ACID solution, then into
The concentration of one step, crystallization, centrifugation, drying, obtain the L MALIC ACID crystal of high-purity.
For the liquid of calcium containing L MALIC ACID and calcium succinate, the present invention is handled using ion exchange resin through multi-step
To the succinic acid of high-purity, specifically:
In the step (i), the liquid of the calcium containing L MALIC ACID and calcium succinate is passed through at cation exchange resin
Reason removal cation.In order to improve the yield of target product, the liquid first can also be carried out acidolysis with sulfuric acid by this step, Gu
Liquid separation, abandons calcium sulphate solid, obtains the mixed liquor containing L MALIC ACID and succinic acid, then the mixed liquor is passed through cationic friendship
Change resin.
In the step (ii), the decationizing solution containing L MALIC ACID and succinic acid will be gone to be passed through anion exchange
Resin is adsorbed, to realize separating for L MALIC ACID and succinic acid and other impurities.The anion exchange resin is preferred
For acrylic type or styrene type anion exchange resin.Dilute sulfuric acid in order to be enriched with target product sufficiently, as eluant, eluent
Mass percentage concentration be preferably 3~5%.The L MALIC ACID and succinic acid being adsorbed on resin afford more through dilute sulfuric acid
The pure eluent containing L MALIC ACID and succinic acid.By the succinic acid knot in the eluent containing L MALIC ACID and succinic acid
It is brilliant, it is preferred to use to be first concentrated into that the mass percentage of dry is 50~70%, the mode dropped again is crystallized, isolated fourth
Diacid coarse crystal.After separating the succinic acid coarse crystal, the mother liquor containing L MALIC ACID and a small amount of succinic acid is also obtained, can be used for
The acidolysis of solid containing L MALIC ACID calcium and calcium succinate in abovementioned steps (1).
In the step (iii), obtained succinic acid coarse crystal is refined using conventional method, available fourth two
Sour finished product.For example, coarse crystal dissolution, decoloration, crystallization, separation, drying are obtained the succinic acid crystal of high-purity.
On the basis of common knowledge of the art, above-mentioned each optimum condition, can be combined with each other, obtain specific embodiment party
Formula.
Compared with prior art, the method for production L MALIC ACID coproduction succinic acid provided by the invention has the advantage that
Crystallization mode of the present invention due to using L MALIC ACID hydrogen calcium, so that the L MALIC ACID hydrogen calcium crystallized out from fermentation liquid has
The feature of purity is high, realizes the separation of L MALIC ACID and succinic acid, to improve the purity of L MALIC ACID, reduce production
Decoloration load in the process so that the malic acid produced have the advantages that purity is high, it is high-quality；The present invention uses resin adsorption
Method in L MALIC ACID calcium and calcium succinate filtered fluid L MALIC ACID and succinic acid recycled, improve L- apple
The yield of acid and succinic acid；The present invention is high using the succinic acid product purity that secondary crystallization mode obtains, high-quality.
Specific embodiment
The preferred embodiment of the present invention is described in detail below in conjunction with embodiment.
Embodiment 1
The present embodiment provides a kind of method for producing L MALIC ACID coproduction succinic acid, this method produces L- apple with fermentation method
The resulting fermentation liquid 33.27kg containing calcium malate and calcium succinate of acid is raw material, is proceeded as follows:
Fermentation liquid raw material is heated to 60 DEG C, centrifuge separation obtains the solid containing L MALIC ACID calcium and calcium succinate
8.06kg and filtrate 25.15kg containing L MALIC ACID calcium and calcium succinate；
The operation that the solid containing L MALIC ACID calcium and calcium succinate is comprised the following steps:
(1) solid is mixed with 8.06kg water and is sized mixing, sulfuric acid is added to slurries pH and carries out acidolysis for 3.0, it is heated
Filter obtains filter cake 9.18kg and filtrate 10.57kg, adjusts filtrate temperature to 20 DEG C, filtering obtains the wet crystal of L MALIC ACID hydrogen calcium
3.5kg；
(2) the wet crystal of L MALIC ACID hydrogen calcium is mixed with 3kg water and is sized mixing, be continuously added sulfuric acid and carry out acidolysis to L- apple
Tartaric acid hydrogen calcium is completely converted into L MALIC ACID, is separated by solid-liquid separation, and collects the L MALIC ACID solution 5.7kg (41.7% (w/ containing L MALIC ACID
w))；
(3) gained L MALIC ACID solution is obtained into L MALIC ACID ion-exchange liquid 6.8kg (containing L- after decoloration, ion-exchange processing
Malic acid 34.9% (w/w), is concentrated into 3.2kg, and crystallization, centrifugation, washing finally obtain L MALIC ACID crystal 1.68kg and mother liquor
1.62kg, by, through detecting, wherein L MALIC ACID content is 99.2% after crystal drying；
The operation that the filtrate containing L MALIC ACID calcium and calcium succinate is comprised the following steps:
(i) the filtrate 10.57kg (wherein L MALIC ACID concentration 2.3% (w/w), 2.1% (w/ of succinic acid concentration are taken
W)), sulfuric acid solution to wherein L MALIC ACID calcium is added to be completely converted into L MALIC ACID, calcium succinate is completely converted into succinic acid (i.e.
Calcium ion is completely converted into calcium sulfate), acid hydrolysis solution 10.2kg is collected in filtering；By the acid hydrolysis solution through cation exchange resin at
Cation exchange liquid 11.5kg is obtained after reason；
(ii) cation exchange liquid is adsorbed with anion exchange resin, and with 1kg water washing, then with 4%
(w/w) sulfuric acid elutes, and obtains the eluent 4.6kg containing L MALIC ACID and succinic acid, is concentrated into dry 60%, decrease temperature crystalline, from
The heart isolated succinic acid coarse crystal 0.21kg and mother liquor 0.58kg (wherein L MALIC ACID concentration 37.7%, succinic acid concentration
5.7%)；
(iii) add water 0.36kg to dissolve by heating the crude product succinic acid, burgy 20g is added and decolourizes 1 hour, is filtered to remove
Burgy, the condensing crystallizing of filtrate containing succinic acid are filtered, washed, dry and obtain succinic acid 0.17kg.
Embodiment 2
The present embodiment provides a kind of method for producing L MALIC ACID coproduction succinic acid, this method produces L- apple with fermentation method
The resulting fermentation liquid 32.45kg containing calcium malate and calcium succinate of acid is raw material, is proceeded as follows:
Fermentation liquid raw material is heated to 70 DEG C, centrifuge separation obtains the solid containing L MALIC ACID calcium and calcium succinate
8.18kg and filtrate containing L MALIC ACID calcium and calcium succinate；
The operation that the solid containing L MALIC ACID calcium and calcium succinate is comprised the following steps:
(1) take the wet L MALIC ACID calcium of 500g and calcium succinate that 350g water is added to size mixing, the L MALIC ACID that embodiment 2 is obtained and
Acidolysis is added to pH2.9 in the mother liquor of succinic acid, filters in 85 DEG C, obtains filtrate 720g, be cooled to 10 DEG C, L- apple is obtained by filtration
Sour hydrogen calcium filter cake 460g,
(2) L MALIC ACID hydrogen calcium filter cake addition 200g water is sized mixing into the acidolysis of after vulcanization acid to terminal, filtrate is obtained by filtration
622g is detected its L MALIC ACID content 48.9%；
(3) 622g filtrate is obtained into L MALIC ACID 213g by decoloration, ion-exchange, concentration, crystallization, drying.
To the filtrate containing L MALIC ACID calcium and calcium succinate, using identical as 1 step (i) of embodiment~(iii)
Method handled, obtain succinic acid product.
Embodiment 3
The present embodiment provides a kind of method for producing L MALIC ACID coproduction succinic acid, this method produces L- apple with fermentation method
The resulting fermentation liquid 32.45kg containing calcium malate and calcium succinate of acid is raw material, is proceeded as follows:
Fermentation liquid raw material is heated to 70 DEG C, centrifuge separation, obtain the solid containing L MALIC ACID calcium and calcium succinate with
And the filtrate containing L MALIC ACID calcium and calcium succinate；
The operation that the solid containing L MALIC ACID calcium and calcium succinate is comprised the following steps:
(1) mother liquor after taking the wet L MALIC ACID calcium of 500g and calcium succinate that 350g is added to filter L MALIC ACID hydrogen calcium is sized mixing, and is added
Sulfuric acid solution filters in 90 DEG C to pH2.1, obtains filtrate 705g, be cooled to 10 DEG C after adding calcium carbonate tune pH3.2, L- is obtained by filtration
Hydrogen malate calcium filter cake 410g,
(2) L MALIC ACID hydrogen calcium filter cake addition 200g water is sized mixing into the acidolysis of after vulcanization acid to terminal, filtrate is obtained by filtration
502g is detected its L MALIC ACID content 51.8%；
(3) 322g filtrate is obtained into L MALIC ACID 195.3g by decoloration, ion-exchange, concentration, crystallization, drying；
To the filtrate containing L MALIC ACID calcium and calcium succinate, using identical as 1 step (i) of embodiment~(iii)
Method handled, obtain succinic acid product.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of method for producing L MALIC ACID coproduction succinic acid, which comprises the steps of:
It is original with fermentation method or the enzyme transforming process production resulting fermentation liquid containing L MALIC ACID calcium and calcium succinate of L MALIC ACID
Material is separated by solid-liquid separation, obtains the solid of calcium containing L MALIC ACID and calcium succinate and the liquid of calcium containing L MALIC ACID and calcium succinate；
The processing that the solid of the calcium containing L MALIC ACID and calcium succinate is included the following steps:
(1) solid is subjected to acidolysis, be separated by solid-liquid separation, abandon calcium sulphate solid, collected and contain L MALIC ACID hydrogen calcium and succinic acid
The mixed solution of hydrogen calcium；The L MALIC ACID hydrogen calcium in the mixed solution is crystallized, L MALIC ACID hydrogen calcium crystal is collected；
(2) the L MALIC ACID hydrogen calcium crystal is subjected to further acidolysis, be separated by solid-liquid separation, abandoned calcium sulphate solid, obtain L- apple
Sour acid hydrolysis solution；
(3) the L MALIC ACID acid hydrolysis solution is refined, obtains L MALIC ACID product；
The processing that the liquid of the calcium containing L MALIC ACID and calcium succinate is included the following steps:
(i) liquid is passed through cation exchange resin, removal cation obtains decationizing solution；
(ii) the decationizing solution is passed through anion exchange resin, sufficiently adsorbs, then eluted with dilute sulfuric acid, must contains
The eluent of L MALIC ACID and succinic acid；The succinic acid in the eluent is crystallized, succinic acid coarse crystal is collected；
(iii) the succinic acid coarse crystal is refined, obtains succinic acid product.
2. the method according to claim 1, wherein the temperature that the fermentation liquid is separated by solid-liquid separation be 10~
100 DEG C, preferably 70~80 DEG C.
3. method according to claim 1 or 2, which is characterized in that the pH value of system is 1.5 when step (1) described acidolysis
~4.5, preferably pH2.0~4.0；
Preferably, the reaction temperature of the acidolysis is 10~100 DEG C, more preferably 70~90 DEG C.
4. method according to any one of claims 1 to 3, which is characterized in that step (1) is described to make L MALIC ACID hydrogen calcium
The condition of crystallization are as follows: control temperature is crystallized at 5~15 DEG C.
5. method described in any one according to claim 1~4, which is characterized in that step (1) crystallization is also contained
The mother liquor is returned and is mixed with fermentation liquid by the mother liquor of L MALIC ACID hydrogen calcium and succinic acid hydrogen calcium, or is used for step (1) described acid
Solution.
6. method described in any one according to claim 1~5, which is characterized in that the temperature of step (2) the further acidolysis
Degree is 20~100 DEG C, and the pH value of acidolysis reaction terminal is 1.5~2.2.
7. method described in any one according to claim 1~6, which is characterized in that the step (i) further include: will be described
Liquid carries out acidolysis with sulfuric acid, is separated by solid-liquid separation, and abandons calcium sulphate solid, the mixed liquor containing L MALIC ACID and succinic acid is obtained, by institute
It states mixed liquor and is passed through cation exchange resin.
8. method described in any one according to claim 1~7, which is characterized in that step (ii) the anion exchange tree
Rouge is acrylic type or styrene type anion exchange resin；
Mass percentage concentration preferably as the dilute sulfuric acid of eluant, eluent is 3~5%.
9. method described in any one according to claim 1~8, which is characterized in that step (ii) is described to crystallize succinic acid
Condition specifically: the mass percentage for being concentrated into dry is 50~70%, then decrease temperature crystalline.
10. method described in any one according to claim 1~9, which is characterized in that step (ii) crystallization is also contained
There is the mother liquor of L MALIC ACID and succinic acid, the mother liquor is used for step (1) described acidolysis.
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| CN201910590995.4A CN110204437A (en) | 2019-07-02 | 2019-07-02 | A method of producing L MALIC ACID coproduction succinic acid |
| CN202010625172.3A CN111732507B (en) | 2019-07-02 | 2020-07-02 | Method for producing L-malic acid and coproducing succinic acid |
| CN202010626545.9A CN111909025B (en) | 2019-07-02 | 2020-07-02 | Method for producing calcium hydrogen malate and application of method in production of malic acid |
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| CN201910590995.4A CN110204437A (en) | 2019-07-02 | 2019-07-02 | A method of producing L MALIC ACID coproduction succinic acid |
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| CN114014751A (en) * | 2021-12-10 | 2022-02-08 | 新疆至臻化工工程研究中心有限公司 | Method for separating and extracting malic acid from succinic acid crystallization filtrate |
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| CN112552164B (en) * | 2020-12-08 | 2022-12-09 | 日照金禾博源生化有限公司 | Process method for extracting malic acid from unqualified sodium citrate mother liquor |
| CN113185397B (en) * | 2021-04-09 | 2023-12-01 | 安徽丰原集团有限公司 | Method for recovering malic acid from fermentation broth |
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| US5068419A (en) * | 1986-12-18 | 1991-11-26 | Uop | Separation of an organic acid from a fermentation broth with an anionic polymeric adsorbent |
| BR9908464A (en) * | 1998-03-02 | 2000-12-05 | Michigan Biotech Inst | Processes for recovering carboxylic acid from a solution containing carboxylic acid, and for producing an ester from a solution containing carboxylic acid |
| US7241918B1 (en) * | 2003-03-18 | 2007-07-10 | Uop Llc | Separation of citric acid from gluconic acid in fermentation broth using a weakly or strongly basic anionic exchange resin adsorbent |
| CN101348428B (en) * | 2008-09-05 | 2011-01-05 | 江南大学 | Method for extracting amber acid in fermentation liquor by anion resin adsorption |
| US9233906B2 (en) * | 2009-12-31 | 2016-01-12 | Group Novasep SAS | Purification of succinic acid from the fermentation broth containing ammonium succinate |
| CN106148209B (en) * | 2015-03-23 | 2020-11-20 | 中国科学院天津工业生物技术研究所 | Novel binary organic acid producing strain and preparation and application thereof |
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Application publication date: 20190906 |