CA2407708A1 - A method for isolating salinomycin from fermentation broth - Google Patents
A method for isolating salinomycin from fermentation broth Download PDFInfo
- Publication number
- CA2407708A1 CA2407708A1 CA002407708A CA2407708A CA2407708A1 CA 2407708 A1 CA2407708 A1 CA 2407708A1 CA 002407708 A CA002407708 A CA 002407708A CA 2407708 A CA2407708 A CA 2407708A CA 2407708 A1 CA2407708 A1 CA 2407708A1
- Authority
- CA
- Canada
- Prior art keywords
- fermentation broth
- salinomycin
- isolating
- biomass
- fermentation
- 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.)
- Abandoned
Links
- 238000000855 fermentation Methods 0.000 title claims abstract description 38
- 230000004151 fermentation Effects 0.000 title claims abstract description 38
- KQXDHUJYNAXLNZ-XQSDOZFQSA-N Salinomycin Chemical compound O1[C@@H]([C@@H](CC)C(O)=O)CC[C@H](C)[C@@H]1[C@@H](C)[C@H](O)[C@H](C)C(=O)[C@H](CC)[C@@H]1[C@@H](C)C[C@@H](C)[C@@]2(C=C[C@@H](O)[C@@]3(O[C@@](C)(CC3)[C@@H]3O[C@@H](C)[C@@](O)(CC)CC3)O2)O1 KQXDHUJYNAXLNZ-XQSDOZFQSA-N 0.000 title claims abstract description 25
- 239000004189 Salinomycin Substances 0.000 title claims abstract description 25
- 229960001548 salinomycin Drugs 0.000 title claims abstract description 25
- 235000019378 salinomycin Nutrition 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims abstract description 11
- 239000002028 Biomass Substances 0.000 claims abstract description 15
- 239000005909 Kieselgur Substances 0.000 claims abstract description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012530 fluid Substances 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 6
- 235000013312 flour Nutrition 0.000 claims abstract description 5
- 239000008187 granular material Substances 0.000 claims abstract description 5
- 239000002023 wood Substances 0.000 claims abstract description 5
- 239000010457 zeolite Substances 0.000 claims abstract description 5
- 230000002378 acidificating effect Effects 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims abstract description 4
- 239000002245 particle Substances 0.000 claims abstract description 3
- 239000000047 product Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 6
- 241000187759 Streptomyces albus Species 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 229910021536 Zeolite Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 2
- 239000003925 fat Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 239000003324 growth hormone secretagogue Substances 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000001694 spray drying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000010796 biological waste Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000273 veterinary drug Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/181—Heterocyclic compounds containing oxygen atoms as the only ring heteroatoms in the condensed system, e.g. Salinomycin, Septamycin
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Processing Of Solid Wastes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Soil Conditioners And Soil-Stabilizing Materials (AREA)
Abstract
The present solution refers to a method of isolating salinomycin for the purpose of obtaining a granulated product. The purpose aforementioned is reached by a method for isolating salinomycin from the fermentation broth according to the invention, the nature of which consists in that the fermentation broth of salinomycin is adjusted to an acidic pH range. A
suitable inert filtration aid such as diatomaceous earth, zeolites, wood flour or a mixture thereof is added in an amount of 5 to 20 wt % referred to the weight of the fermentation broth. The biomass is separated by filtration, granulated and dried in a fluid bed drier. The dry granules are ground and sieved to a required particle size.
suitable inert filtration aid such as diatomaceous earth, zeolites, wood flour or a mixture thereof is added in an amount of 5 to 20 wt % referred to the weight of the fermentation broth. The biomass is separated by filtration, granulated and dried in a fluid bed drier. The dry granules are ground and sieved to a required particle size.
Description
A METHOD FOR ISOLATING SALINOMYCIN FROM FERMENTATION BROTH
Technical field The invention relates to a process of isolation of salinomycin from the harvested fermentation broth.
Present Technical Status Spray drying of the fermentation broth to which an anti-caking agent and a filling agent have been admixed, is used for preparation of salinomycin feed grade or the pure form is isolated after the biomass separation by extraction, concentration and purification of the raw product by recrystallization. Isolation of the pure form is rather demanding as concerns the high production costs and mechanical-technological equipment of the operation plant (US pat. Document 4,212,492, US
pat. Document 4, 137, 247).
There is no need for pure form preparation should salinomycin be used as a veterinary drug or growth stimulator. After completion of the fermentation, the treated broth can be directly dried together with anti-caking agents admixed to it.
Before drying, the broth can be concentrated on an evaporator (US pat.
Document 4,395,491). .
The harvested fermentation broth of salinomycin contains many by-products that pose a problem after spray drying of the broth. Solid substances agglomerate, form clods and can not be further processed. The major reason for the agglomerate formation is the content of fat. The fats contained in the solids manifest themselves predominantly in high temperature processing, when they are moist and at mechanical stress. The product obtained from the spray drier is very dusty, and therefore, it is necessary to granulate it (US pat.
Document 5,529,9'11).
The granulation process can be performed either directly in a combined fluid bed- spray drier, or at a subsequent isolation step using a dry or wet method of processing.
It has been found out that ifi is possible to isolate the solid substances in the form of granules. from the salinomycirt fermentation broth without the formation of agglomerates. .
Backgiround of the Invention The above disadvantages are eliminated by the method for isolating salinomycin from the fermentation broth according to this invention. The nature of the invention consists in that the salinomycin fermentation broth is adjusted to an acidic pH
value of 4 to 5. A suitable inert filtration aid such as diatomaceous earth, zeolites, wood flour or a mixture thereof is added in amount ranging from 5 to wt % referred to the weight of the treated fermentation broth. The biomass is separated by filtration then granulated and dried in a fluid bed dryer.
Subsequently, the granules are ground and sieved to the required particle size.
The present method ensures a product which satisfies the veterinary code. It is advantageous that the active substance exists within an acidic pH range in cells of the biomass, and thus it is possible to discard the separated filtrate obtained by this process to the biological waste water treatment plant for aerobic treatment. Further, the dry matter content of the biomass thus obtained is higher than that of the fermentation broth, it being the reason that power consumption needed for drying the biomass is lower than the consumption for drying the whole amount of the fermentation broth.
Examples of Embodiments of the Invention Example 1 The fermentation broth obtained by fermentation of Streptomyces albus had, after 128 hours of cultivation, the pH value of 6,1 and a salinomycin content of 18,4 g/kg. 527 kg of the harvested fermentation broth have been adjusted by an addition of 10% HCI to a pH value of 4,0. Wood flour (8 wt % referred to the weight of the broth) was added to the treated fermentation broth. Using a rotary vacuum filter filled with wood flour we obtained 119,7 kg of biomass and 460,7 kg of filtrate which contained less than 0,01 % of salinomycin and after neutralisation it was discharged to the waste water aerobic treatment plant.
The separated biomass passed through a granulator and was dried in a fluid bed drier giving an amount of 74,2 kg of the product containing 12,3% of salinomycin.
Example 2 The fermentation by Streptomyces albus of the fermentation broth was terminated after 120 hours. The broth had a pH value of 6,0 and a salinomycin content of 22,6 g/kg. An amount of 589 kg of fermentation broth was adjusted by addition of 10% HCI to a pH value of 5,0. Zeolite and diatomaceous earth were added (15 wt % referred to the weight of treated fermentation broth). Using a rotary vacuum filter filled with diatomaceous earth, we obtained an amount of 184,7 kg of biomass and 495,6 kg of filtrate which contained less than 0,02% of salinomycin and was discarded as in Example 1.
The separated biomass was granulated and dried in the fluid bed drier giving an amount of 106,5 kg product containing 12,1% salinomycin.
Example 3 The fermentation broth obtained by fermentation of Streptomyces albus had, after 124 hours of fermentation, a pH value of 6,2 and a salinomycin content of 17,1 g/kg. By addition of a NaOH solution, a pH value of 7 to 8 was reached.
The fermentation broth thus treated was heated to a temperature of 60 °C, and after cooling, the pH value was adjusted by diluted HCI as in Example 1.
Zeolite (20 wt % referred to the weight of the fermentation broth) was added to 524 kg of the treated fermentation broth. We filtered the mixture through a layer of diatomaceous earth filter aid using a rotary vacuum filter and obtained an amount of 184,7 kg of biomass and 495,6 kg of filtrate which contained less than 0,001 of salinomycin. The filtrate was discarded as in Example 1.
The separated biomass, having passed through a granulator, was dried in a fluid bed drier giving an amount of 80,7 kg of the product containing 10,9% of salinomycin.
Example 4 The fermentation broth obtained by fermenting Streptomyces albus had, after 128 hours of fermentation, a pH value of 6,3 and a salinomycin content of 15,5 g/kg. An amount of 566,6 kg of the fermentation broth was adjusted by an addition of 10% HCI to a pH value of 4,7. Diatomaceous earth (5 wt % referred to the weight of the fermentation broth) was added to the treated fermentation broth.
We used a rotary vacuum filter filled with diatomaceous earth. We obtained 100,7 of kg biomass and 500,6 kg of filtrate with a low content of salinomycin which, following neutralisation, was discarded fio the waste water aerobic treatment plant. The separated biomass was then processed by granulation, dried in the fluid bed drier giving an amount of 68,4 kg of a dry product containing 12,8% of salinomycin.
Industrial Applicability Salinomycin is used in veterinary medicine as a coccidiostat coccidium and as a growth stimulator in feeding farm animals
Technical field The invention relates to a process of isolation of salinomycin from the harvested fermentation broth.
Present Technical Status Spray drying of the fermentation broth to which an anti-caking agent and a filling agent have been admixed, is used for preparation of salinomycin feed grade or the pure form is isolated after the biomass separation by extraction, concentration and purification of the raw product by recrystallization. Isolation of the pure form is rather demanding as concerns the high production costs and mechanical-technological equipment of the operation plant (US pat. Document 4,212,492, US
pat. Document 4, 137, 247).
There is no need for pure form preparation should salinomycin be used as a veterinary drug or growth stimulator. After completion of the fermentation, the treated broth can be directly dried together with anti-caking agents admixed to it.
Before drying, the broth can be concentrated on an evaporator (US pat.
Document 4,395,491). .
The harvested fermentation broth of salinomycin contains many by-products that pose a problem after spray drying of the broth. Solid substances agglomerate, form clods and can not be further processed. The major reason for the agglomerate formation is the content of fat. The fats contained in the solids manifest themselves predominantly in high temperature processing, when they are moist and at mechanical stress. The product obtained from the spray drier is very dusty, and therefore, it is necessary to granulate it (US pat.
Document 5,529,9'11).
The granulation process can be performed either directly in a combined fluid bed- spray drier, or at a subsequent isolation step using a dry or wet method of processing.
It has been found out that ifi is possible to isolate the solid substances in the form of granules. from the salinomycirt fermentation broth without the formation of agglomerates. .
Backgiround of the Invention The above disadvantages are eliminated by the method for isolating salinomycin from the fermentation broth according to this invention. The nature of the invention consists in that the salinomycin fermentation broth is adjusted to an acidic pH
value of 4 to 5. A suitable inert filtration aid such as diatomaceous earth, zeolites, wood flour or a mixture thereof is added in amount ranging from 5 to wt % referred to the weight of the treated fermentation broth. The biomass is separated by filtration then granulated and dried in a fluid bed dryer.
Subsequently, the granules are ground and sieved to the required particle size.
The present method ensures a product which satisfies the veterinary code. It is advantageous that the active substance exists within an acidic pH range in cells of the biomass, and thus it is possible to discard the separated filtrate obtained by this process to the biological waste water treatment plant for aerobic treatment. Further, the dry matter content of the biomass thus obtained is higher than that of the fermentation broth, it being the reason that power consumption needed for drying the biomass is lower than the consumption for drying the whole amount of the fermentation broth.
Examples of Embodiments of the Invention Example 1 The fermentation broth obtained by fermentation of Streptomyces albus had, after 128 hours of cultivation, the pH value of 6,1 and a salinomycin content of 18,4 g/kg. 527 kg of the harvested fermentation broth have been adjusted by an addition of 10% HCI to a pH value of 4,0. Wood flour (8 wt % referred to the weight of the broth) was added to the treated fermentation broth. Using a rotary vacuum filter filled with wood flour we obtained 119,7 kg of biomass and 460,7 kg of filtrate which contained less than 0,01 % of salinomycin and after neutralisation it was discharged to the waste water aerobic treatment plant.
The separated biomass passed through a granulator and was dried in a fluid bed drier giving an amount of 74,2 kg of the product containing 12,3% of salinomycin.
Example 2 The fermentation by Streptomyces albus of the fermentation broth was terminated after 120 hours. The broth had a pH value of 6,0 and a salinomycin content of 22,6 g/kg. An amount of 589 kg of fermentation broth was adjusted by addition of 10% HCI to a pH value of 5,0. Zeolite and diatomaceous earth were added (15 wt % referred to the weight of treated fermentation broth). Using a rotary vacuum filter filled with diatomaceous earth, we obtained an amount of 184,7 kg of biomass and 495,6 kg of filtrate which contained less than 0,02% of salinomycin and was discarded as in Example 1.
The separated biomass was granulated and dried in the fluid bed drier giving an amount of 106,5 kg product containing 12,1% salinomycin.
Example 3 The fermentation broth obtained by fermentation of Streptomyces albus had, after 124 hours of fermentation, a pH value of 6,2 and a salinomycin content of 17,1 g/kg. By addition of a NaOH solution, a pH value of 7 to 8 was reached.
The fermentation broth thus treated was heated to a temperature of 60 °C, and after cooling, the pH value was adjusted by diluted HCI as in Example 1.
Zeolite (20 wt % referred to the weight of the fermentation broth) was added to 524 kg of the treated fermentation broth. We filtered the mixture through a layer of diatomaceous earth filter aid using a rotary vacuum filter and obtained an amount of 184,7 kg of biomass and 495,6 kg of filtrate which contained less than 0,001 of salinomycin. The filtrate was discarded as in Example 1.
The separated biomass, having passed through a granulator, was dried in a fluid bed drier giving an amount of 80,7 kg of the product containing 10,9% of salinomycin.
Example 4 The fermentation broth obtained by fermenting Streptomyces albus had, after 128 hours of fermentation, a pH value of 6,3 and a salinomycin content of 15,5 g/kg. An amount of 566,6 kg of the fermentation broth was adjusted by an addition of 10% HCI to a pH value of 4,7. Diatomaceous earth (5 wt % referred to the weight of the fermentation broth) was added to the treated fermentation broth.
We used a rotary vacuum filter filled with diatomaceous earth. We obtained 100,7 of kg biomass and 500,6 kg of filtrate with a low content of salinomycin which, following neutralisation, was discarded fio the waste water aerobic treatment plant. The separated biomass was then processed by granulation, dried in the fluid bed drier giving an amount of 68,4 kg of a dry product containing 12,8% of salinomycin.
Industrial Applicability Salinomycin is used in veterinary medicine as a coccidiostat coccidium and as a growth stimulator in feeding farm animals
Claims
A method for isolating salinomycin from a fermentation broth, characterised in that the fermentation broth is adjusted to an acidic pH value of 4 to 5, a suitable inert filtering aids, such as diatomaceous earth, zeolites, wood flour or mixtures thereof (5 to 20 wt % referred to the weight of the fermentation broth) are added to fermentation broth, the biomass is separated by filtration, granulated and then dried in a fluid bed drier, and the obtained dry granules are ground and sieved to a required particle size.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SK664-2000A SK283167B6 (en) | 2000-05-04 | 2000-05-04 | Method for isolation of salinomycin from the fermented soil |
| SKPV0664-2000 | 2000-05-04 | ||
| PCT/SK2001/000015 WO2001083801A2 (en) | 2000-05-04 | 2001-05-03 | A method for isolating salinomycin from fermentation broth |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2407708A1 true CA2407708A1 (en) | 2001-11-08 |
Family
ID=20435891
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002407708A Abandoned CA2407708A1 (en) | 2000-05-04 | 2001-05-03 | A method for isolating salinomycin from fermentation broth |
Country Status (8)
| Country | Link |
|---|---|
| AU (1) | AU2001255144A1 (en) |
| BR (1) | BR0110589A (en) |
| CA (1) | CA2407708A1 (en) |
| CZ (1) | CZ20023429A3 (en) |
| DE (1) | DE10196144T1 (en) |
| SI (1) | SI21043A (en) |
| SK (1) | SK283167B6 (en) |
| WO (1) | WO2001083801A2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007145858A1 (en) * | 2006-06-13 | 2007-12-21 | Phibro Animal Health Corporation | Method of reducing the growth of lactobacilli in a process of ethanol production by yeast fermentation comprising adding a pristinamycin-type antimicrobial agent and/or a polyether ionophore antimicrobial agent dissolved in an organic solvent |
| CN108478536B (en) * | 2018-03-30 | 2019-02-26 | 内蒙古拜克生物有限公司 | A kind of salinomycin prilling process |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2353031C2 (en) * | 1972-10-27 | 1985-02-21 | Brevetti Gabbiani S.p.A., Podenzano, Piacenza | Device for forwarding objects at an angle, in particular for processing sections of plate elements |
| US4009262A (en) * | 1975-04-21 | 1977-02-22 | Eli Lilly And Company | Antibiotic a-28086 recovery process |
| JPS53148595A (en) * | 1977-06-01 | 1978-12-25 | Kaken Pharmaceut Co Ltd | Preparation of salinomycines |
| DE3005642A1 (en) * | 1980-02-15 | 1981-08-20 | Hoechst Ag, 6000 Frankfurt | SOLID OF THE SALINOMYCIN CULTURAL BROTH AND METHOD FOR ITS PRODUCTION |
| JPS61247398A (en) * | 1986-01-21 | 1986-11-04 | Kaken Pharmaceut Co Ltd | Production of salinomycin |
| BG60973B1 (en) * | 1990-12-21 | 1996-07-31 | Biochemie Gesellschaft M.B.H. | Granulate of salinomycin biomass, with free fluidity, containing no dust and with unlimited availability of the active substance, and method for its preparation |
-
2000
- 2000-05-04 SK SK664-2000A patent/SK283167B6/en unknown
-
2001
- 2001-05-03 CZ CZ20023429A patent/CZ20023429A3/en unknown
- 2001-05-03 AU AU2001255144A patent/AU2001255144A1/en not_active Abandoned
- 2001-05-03 CA CA002407708A patent/CA2407708A1/en not_active Abandoned
- 2001-05-03 WO PCT/SK2001/000015 patent/WO2001083801A2/en not_active Application Discontinuation
- 2001-05-03 DE DE10196144T patent/DE10196144T1/en not_active Withdrawn
- 2001-05-03 SI SI200120024A patent/SI21043A/en not_active IP Right Cessation
- 2001-05-03 BR BR0110589-2A patent/BR0110589A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001083801A2 (en) | 2001-11-08 |
| SK283167B6 (en) | 2003-03-04 |
| CZ20023429A3 (en) | 2003-04-16 |
| BR0110589A (en) | 2003-04-01 |
| AU2001255144A1 (en) | 2001-11-12 |
| SI21043A (en) | 2003-04-30 |
| DE10196144T1 (en) | 2003-04-17 |
| SK6642000A3 (en) | 2002-01-07 |
| WO2001083801A3 (en) | 2002-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CZ300262B6 (en) | Process for preparing L-Lysine feed supplement | |
| KR19990035867A (en) | How to extract proanthocyanidins from materials collected from plants | |
| RU2007124368A (en) | METHOD OF INDUSTRIAL PROCESSING OF OIL BY-PRODUCTS AND PRODUCED PRODUCT | |
| JPH0367659B2 (en) | ||
| EP2668849A1 (en) | Feed additive of plant origin | |
| EP2674397B1 (en) | Method for preparing an intercalated and/or exfoliated organophillic clay from clay and macroalgae, corresponding fertiliser product, food supplement for animals and fish feed | |
| CN1665521A (en) | Purified amylase inhibitor and novel process for obtaining the same | |
| CA2407708A1 (en) | A method for isolating salinomycin from fermentation broth | |
| JPH0339677B2 (en) | ||
| JP2000102378A (en) | High-density bacillus sp and highly concentrated bacillus sp metabolite-including material, and production and utilization thereof | |
| US5061627A (en) | Method for preparing enzymes from crustaceans | |
| CN1056845C (en) | Purification for riboflavin | |
| US20100304449A1 (en) | Method for Obtaining Products Containing Different Concentrations of Compounds Produced by Fermentation | |
| RU2215426C2 (en) | Brewing wastes reprocessing method (versions) | |
| CN101496554A (en) | Garlic stalk extract powder and extracting method | |
| CN104744277A (en) | Simulated moving bed and method for extracting three-branch chain amino acid based on simulated moving bed | |
| EP3023409A1 (en) | Method for extracting ferulic acid and/or its salts | |
| KR100876921B1 (en) | How to soften the shell of a crustacean or the keratin of a beast. | |
| RU2070808C1 (en) | Brown algae processing method | |
| KR102751562B1 (en) | Method for manufacturing bittern-derived food or feed additives | |
| RU2178708C2 (en) | Method of insulin producing | |
| KR100450048B1 (en) | a manufacturing method of the arabinoxylane by means of the barns of barley | |
| RU2097980C1 (en) | Method for producing biologically-active substances | |
| US4045582A (en) | Beneficiation of uric acid from natural products | |
| KR20090040788A (en) | Manufacturing method of water improver for fish farm |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |