CN112457207A - Method for extracting pharmaceutical-grade leucine by using solvent method - Google Patents
Method for extracting pharmaceutical-grade leucine by using solvent method Download PDFInfo
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- CN112457207A CN112457207A CN202011205585.2A CN202011205585A CN112457207A CN 112457207 A CN112457207 A CN 112457207A CN 202011205585 A CN202011205585 A CN 202011205585A CN 112457207 A CN112457207 A CN 112457207A
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- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 title claims abstract description 66
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 31
- 239000002904 solvent Substances 0.000 title claims abstract description 10
- WYCOJIVDCGJKDB-UHFFFAOYSA-N 3,4-dimethylbenzenesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1C WYCOJIVDCGJKDB-UHFFFAOYSA-N 0.000 claims abstract description 29
- 238000000855 fermentation Methods 0.000 claims abstract description 20
- 230000004151 fermentation Effects 0.000 claims abstract description 20
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 16
- 238000001035 drying Methods 0.000 claims abstract description 11
- 239000000126 substance Substances 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 37
- 238000003756 stirring Methods 0.000 claims description 36
- 239000008367 deionised water Substances 0.000 claims description 28
- 229910021641 deionized water Inorganic materials 0.000 claims description 28
- 238000001914 filtration Methods 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 19
- 239000006228 supernatant Substances 0.000 claims description 17
- 239000000706 filtrate Substances 0.000 claims description 14
- 239000000047 product Substances 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 8
- 239000002244 precipitate Substances 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 238000010923 batch production Methods 0.000 abstract description 2
- 238000001556 precipitation Methods 0.000 abstract description 2
- 238000004806 packaging method and process Methods 0.000 abstract 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 229960003136 leucine Drugs 0.000 description 45
- 238000000605 extraction Methods 0.000 description 7
- 235000019454 L-leucine Nutrition 0.000 description 4
- 239000004395 L-leucine Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000002390 rotary evaporation Methods 0.000 description 3
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/38—Separation; Purification; Stabilisation; Use of additives
- C07C227/40—Separation; Purification
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/08—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to hydrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/29—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings
- C07C309/30—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton of non-condensed six-membered aromatic rings of six-membered aromatic rings substituted by alkyl groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a method for extracting pharmaceutical-grade leucine by using a solvent method, which comprises the following specific processes of 1) preparing fermentation liquor; 2) removing protein in the fermentation liquor; 3) concentrating the fermentation liquor; 4) carrying out chemical combination reaction on o-xylene-4-sulfonic acid and fermentation liquor for precipitation to generate leucine xylene-4-sulfonate; 5) dissolving leucine xylene-4-sulfonate, adding ammonia water for hydrolysis, and removing o-xylene-4-sulfonic acid; 6) decoloring; 7) drying, crushing, detecting finished products and packaging. In the production process, the method is simple and convenient to operate, has high separation purity, and effectively solves the problem of batch production of the pharmaceutical leucine.
Description
Technical Field
The invention belongs to the technical field of amino acid extraction, and relates to a method for extracting pharmaceutical leucine by using a solvent method.
Technical Field
L-leucine is also called leucine, its chemical name is alpha-aminoisocaproic acid, and its molecular formula is C6H13O2N, relative molecular weight 131.18, is a nonpolar amino acid, slightly bitter in taste, soluble in water, has an isoelectric point of 5.98, and has wide application in many industries such as the manufacture of medicines, foods, flavoring agents, animal feeds, cosmetics, and the like. The research of China on L-leucine starts relatively late, the L-leucine production level of partial enterprises by fermentation methods is relatively low, the research on downstream pretreatment and extraction processes is relatively less, the industrial production is difficult to realize, and the problems of high acid and alkali consumption, serious pollution, low product yield and purity and the like exist.
In the production and extraction process of leucine, a common production method comprises membrane filtration, deionization, decolorization and drying to obtain leucine. The production method has long time consumption and high cost, and the purity of the product is difficult to reach the pharmaceutical grade standard.
Disclosure of Invention
In order to solve the technical problem of low purity of L-leucine in industrial extraction, the invention provides a method for extracting pharmaceutical-grade leucine by using a solvent method.
The invention is realized by the following technical scheme.
A method for extracting pharmaceutical grade leucine using a solvent process, comprising the steps of:
the o-xylene-4-sulfonic acid and leucine fermentation liquor are combined, reacted and precipitated to produce leucine xylene-4-sulfonate, then the leucine xylene-4-sulfonate is added with ammonia water to make hydrolysis, and the o-xylene-4-sulfonic acid is removed, and then the above-mentioned materials are decolourized, dried and pulverized so as to obtain the invented product.
Further, the method comprises the steps of:
1) taking leucine fermentation liquor, filtering, sterilizing, and concentrating at 60 ℃;
2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid, stirring for 30min, standing for 2h, and reacting to generate leucine xylene-4-sulfonate;
3) discarding supernatant, washing with deionized water, heating to 70-80 deg.C, adding 30ml ammonia water while stirring, adjusting pH to 7-8, stirring for 30min, and standing for 2 hr;
4) filtering to remove o-xylene-4-sulfonic acid, adding deionized water and activated carbon, stirring for dissolving, keeping the temperature at 34-36 deg.C, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2min, and removing supernatant;
7) drying at 85 deg.C for 3 h.
Further, the method comprises the steps of:
1) taking 10L of leucine fermentation liquor, centrifuging, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 5L of water;
2) cooling the concentrated solution to 20-30 ℃, adding 300g of o-xylene-4-sulfonic acid, stirring for 30min, standing for 2h, and reacting to generate leucine xylene-4-sulfonate;
3) discarding the supernatant, adding deionized water with the residual volume being 8 times of the volume of the supernatant, washing for 2 times, adding deionized water with the residual volume being 8 times of the volume of the supernatant, heating to 70-80 ℃, adding 30ml of ammonia water while stirring, and adjusting the pH: 7-8, stirring for 30min, and standing for 2 h;
4) filtering to remove o-xylene-4-sulfonic acid, adding 20 times volume of deionized water and 10g of active carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2min, and removing supernatant;
7) drying at 85 deg.C for 3 h.
Still further, the method comprises the steps of:
1) taking 100L of leucine fermentation liquor, centrifuging at 5000rpm for 4min by adopting a high-speed disc centrifuge, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 50L of water;
2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid 3KG, stirring for 30min, standing for 2h, and carrying out a chemical combination reaction to generate leucine xylene-4-sulfonate;
3) removing supernatant, adding deionized water with volume 8-10 times of the residual volume, washing for 2 times, adding 10 times of deionized water, heating to 70-80 deg.C, adding 300ml ammonia water while stirring, stirring for 30min, and standing for 2 hr;
4) filtering to remove o-xylene-4-sulfonic acid, adding 25 times volume of deionized water and 100g of active carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2 min;
7) drying at 85 deg.C for 3 h.
The invention also claims a pharmaceutical grade leucine product prepared by the method.
Compared with the prior art, the invention has the advantages that the following aspects are mainly included but not limited:
according to a large number of experiments, o-xylene-4-sulfonic acid and leucine fermentation liquor are subjected to chemical combination reaction and precipitation to generate leucine xylene-4-sulfonate, ammonia water is added for hydrolysis, o-xylene-4-sulfonic acid is removed, and the leucine is decolorized, dried and crushed to prepare a novel pharmaceutical-grade leucine product, wherein the purity of the product meets the detection requirement of pharmacopoeia on leucine, and the product can be produced in large batches, so that the problem of large-batch production of pharmaceutical-grade leucine is solved.
Detailed Description
In order to make those skilled in the art better understand the technical solutions in the present application, the present invention will be described more clearly and completely below with reference to specific embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
A method for extracting pharmaceutical grade leucine by using a solvent method, wherein main experimental equipment and reagents for experimental extraction comprise: a rotary evaporation concentrator, a centrifuge, a plate frame, 10L leucine fermentation liquor, 300g o-xylene-4-sulfonic acid, 30ml ammonia water, 10g activated carbon, deionized water and the like.
(1) Taking 10L of leucine fermentation broth, centrifuging at 5000rpm for 4min by adopting a high-speed disc centrifuge, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 5L of water;
(2) cooling the concentrated solution to 20-30 ℃, adding 300g of o-xylene-4-sulfonic acid, stirring for 30min, standing for 2h, and carrying out a chemical combination reaction to generate leucine xylene-4-sulfonate;
(3) removing supernatant, adding 8 times of deionized water of the residual volume, washing with water for 2 times, adding 8-10 times of deionized water, heating to 70-80 deg.C, adding 30ml of ammonia water while stirring, stirring for 30min, and standing for 2 hr;
(4) filtering to remove o-xylene-4-sulfonic acid, adding 20 times of deionized water and 10g of active carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
(5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
(6) centrifuging at 6000r/min for 2 min;
(7) drying at 85 ℃ for 3h, and detecting various indexes of the product, namely 2000 edition II on leucine. Wherein the purity of the leucine is more than 99.5 percent.
Example 2
A method for extracting pharmaceutical grade leucine by using a solvent method, wherein main experimental equipment and reagents for experimental extraction comprise: a rotary evaporation concentrator, a centrifuge, a plate frame, 100L leucine fermentation liquor, 3KG o-xylene-4-sulfonic acid, 300ml ammonia water, 100g activated carbon, deionized water and the like.
(1) Taking 100L of leucine fermentation liquor, centrifuging at 5000rpm for 4min by adopting a high-speed disc centrifuge, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 50L of water;
(2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid 3KG, stirring for 30min, standing for 2h, and carrying out a chemical combination reaction to generate leucine xylene-4-sulfonate;
(3) removing supernatant, adding deionized water with residual volume of 8-10 times, washing for 2 times, adding 10 times deionized water, heating to 70-80 deg.C, adding 300ml ammonia water while stirring, stirring for 30min, and standing for 2 hr;
(4) filtering to remove o-xylene-4-sulfonic acid, adding 25 times of deionized water and 100g of activated carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
(5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
(6) centrifuging at 6000r/min for 2 min;
(7) drying at 85 ℃ for 3h, and detecting various indexes of the product, namely 2000 edition II on leucine. Wherein the purity of the leucine is more than 99.5 percent.
Example 3
A method for extracting pharmaceutical grade leucine by using a solvent method, wherein main experimental equipment and reagents for experimental extraction comprise: a rotary evaporation concentrator, a centrifuge, a plate frame, 100L leucine fermentation liquor, 3.2KG o-xylene-4-sulfonic acid, 320ml ammonia water, 120g activated carbon, deionized water and the like.
(1) Taking 100L leucine fermentation broth, centrifuging at 5000rpm for 4min by adopting a high-speed disc centrifuge, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 40L water;
(2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid 3KG, stirring for 30min, standing for 1.5h, and carrying out a chemical combination reaction to generate leucine xylene-4-sulfonate;
(3) removing supernatant, adding 8 times of deionized water to wash for 2 times, adding 8-10 times of deionized water, heating to 70-80 deg.C, adding 300ml of ammonia water while stirring, stirring for 30min, and standing for 1.5 hr;
(4) filtering to remove o-xylene-4-sulfonic acid, adding 25 times of deionized water and 100g of activated carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
(5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
(6) centrifuging at 6000r/min for 2 min;
(7) drying at 85 ℃ for 3h, and detecting various indexes of the product, namely 2000 edition II on leucine. Wherein the purity of the leucine is more than 99.5 percent.
The foregoing list is only illustrative of the preferred embodiments of the present invention. It is obvious that the invention is not limited to the above embodiments, but that many variations are possible. All modifications which can be derived or suggested by a person skilled in the art from the disclosure of the present invention are to be considered within the scope of the invention.
Claims (5)
1. A method for extracting pharmaceutical grade leucine using a solvent process, comprising the steps of:
the o-xylene-4-sulfonic acid and leucine fermentation liquor are combined, reacted and precipitated to produce leucine xylene-4-sulfonate, then the leucine xylene-4-sulfonate is added with ammonia water to make hydrolysis, and the o-xylene-4-sulfonic acid is removed, and then the above-mentioned materials are decolourized, dried and pulverized so as to obtain the invented product.
2. Method according to claim 1, characterized in that it comprises the following steps:
1) taking leucine fermentation liquor, filtering, sterilizing, and concentrating at 60 ℃;
2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid, stirring for 30min, standing for 2h, and reacting to generate leucine xylene-4-sulfonate;
3) discarding supernatant, washing with deionized water, heating to 70-80 deg.C, adding 30ml ammonia water while stirring, adjusting pH to 7-8, stirring for 30min, and standing for 2 hr;
4) filtering to remove o-xylene-4-sulfonic acid, adding deionized water and activated carbon, stirring for dissolving, keeping the temperature at 34-36 deg.C, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2min, and removing supernatant;
7) drying at 85 deg.C for 3 h.
3. Method according to claim 1, characterized in that it comprises the following steps:
1) taking 10L of leucine fermentation liquor, centrifuging, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 5L of water;
2) cooling the concentrated solution to 20-30 ℃, adding 300g of o-xylene-4-sulfonic acid, stirring for 30min, standing for 2h, and reacting to generate leucine xylene-4-sulfonate;
3) discarding the supernatant, adding deionized water with the residual volume being 8 times of the volume of the supernatant, washing for 2 times, adding deionized water with the residual volume being 8 times of the volume of the supernatant, heating to 70-80 ℃, adding 30ml of ammonia water while stirring, and adjusting the pH: 7-8, stirring for 30min, and standing for 2 h;
4) filtering to remove o-xylene-4-sulfonic acid, adding 20 times volume of deionized water and 10g of active carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2min, and removing supernatant;
7) drying at 85 deg.C for 3 h.
4. Method according to claim 1, characterized in that it comprises the following steps:
1) taking 100L of leucine fermentation liquor, centrifuging at 5000rpm for 4min by adopting a high-speed disc centrifuge, collecting filtrate and mycoprotein precipitate, and concentrating the filtrate at 60 ℃ to obtain 50L of water;
2) cooling the concentrated solution to 20-30 ℃, adding o-xylene-4-sulfonic acid 3KG, stirring for 30min, standing for 2h, and carrying out a chemical combination reaction to generate leucine xylene-4-sulfonate;
3) removing supernatant, adding deionized water with volume 8-10 times of the residual volume, washing for 2 times, adding 10 times of deionized water, heating to 70-80 deg.C, adding 300ml ammonia water while stirring, stirring for 30min, and standing for 2 hr;
4) filtering to remove o-xylene-4-sulfonic acid, adding 25 times volume of deionized water and 100g of active carbon, stirring to dissolve, keeping the temperature between 34 and 36 ℃, filtering and decolorizing;
5) concentrating the effluent to 1/5 of the original volume, and stopping concentration;
6) centrifuging at 6000r/min for 2 min;
7) drying at 85 deg.C for 3 h.
5. A pharmaceutical grade leucine product prepared according to the process of any one of claims 1-4.
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101108815A (en) * | 2007-08-03 | 2008-01-23 | 湖北新生源生物工程股份有限公司 | Method of recycling precipitating agent in production of L-leueine |
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- 2020-11-02 CN CN202011205585.2A patent/CN112457207A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101108815A (en) * | 2007-08-03 | 2008-01-23 | 湖北新生源生物工程股份有限公司 | Method of recycling precipitating agent in production of L-leueine |
Non-Patent Citations (2)
| Title |
|---|
| 翁连进 等: "邻二甲苯- 4- 磺酸从猪血粉水解液中沉淀提取L-亮氨酸的工艺", 《化工进展》 * |
| 韩勇 等: "亮氨酸沉淀法在色层法分离多种氨基酸工艺中的应用", 《氨基酸杂志》 * |
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