CN1460671A - Method for extracting and separating 1,3-propylene glycol from microbial fermented liquor - Google Patents
Method for extracting and separating 1,3-propylene glycol from microbial fermented liquor Download PDFInfo
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- CN1460671A CN1460671A CN 03133584 CN03133584A CN1460671A CN 1460671 A CN1460671 A CN 1460671A CN 03133584 CN03133584 CN 03133584 CN 03133584 A CN03133584 A CN 03133584A CN 1460671 A CN1460671 A CN 1460671A
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- ammediol
- alcohol
- ketone
- supernatant liquor
- precipitation
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- 238000000034 method Methods 0.000 title claims abstract description 13
- 230000000813 microbial effect Effects 0.000 title claims description 8
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000006228 supernatant Substances 0.000 claims abstract description 15
- 238000004821 distillation Methods 0.000 claims abstract description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000001914 filtration Methods 0.000 claims abstract description 9
- 150000002576 ketones Chemical class 0.000 claims abstract description 9
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001556 precipitation Methods 0.000 claims abstract description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims abstract description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000001816 cooling Methods 0.000 claims abstract description 3
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 14
- 238000000605 extraction Methods 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 9
- 230000008020 evaporation Effects 0.000 claims description 9
- 238000000855 fermentation Methods 0.000 claims description 8
- 230000004151 fermentation Effects 0.000 claims description 8
- 238000005119 centrifugation Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 238000012262 fermentative production Methods 0.000 claims description 4
- 239000011345 viscous material Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 3
- 238000005406 washing Methods 0.000 claims description 3
- -1 cost height Chemical compound 0.000 claims description 2
- 238000005516 engineering process Methods 0.000 abstract description 6
- 235000019441 ethanol Nutrition 0.000 abstract 3
- 239000012530 fluid Substances 0.000 abstract 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 238000000703 high-speed centrifugation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- FRXSZNDVFUDTIR-UHFFFAOYSA-N 6-methoxy-1,2,3,4-tetrahydroquinoline Chemical compound N1CCCC2=CC(OC)=CC=C21 FRXSZNDVFUDTIR-UHFFFAOYSA-N 0.000 description 2
- 241000193830 Bacillus <bacterium> Species 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000005265 energy consumption Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920002215 polytrimethylene terephthalate Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000003311 flocculating effect Effects 0.000 description 1
- 238000005189 flocculation Methods 0.000 description 1
- 230000016615 flocculation Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000005374 membrane filtration Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The present invention belongs to the field of biological engineering technology, in particular, it relates to a method for extracting and separating 1,3-propanediol from fermented liquor. It includes the following steps: directly distilling and concentrating fermented liquor with bacteria to 1/2-1/20 of original volume, cooling, adding ethyl alcohol or methyl alcohol, n-propyl alcohol, isopropyl alcohol, acetone or butanone according to volume ratio of 1:0.3-1:5, settling or filtering or 1000-4500 rpm centrifugal separation and precipitation, taking supernatant fluid, then using alcohol or ketone to wash and precipitating, then settling or filtering or 1000-1500 rpm centrifugal separation and precipitation, taking supernatant fluid, then recovering alcohol or ketone from said supernatant fluid by means of distillation or rectification.
Description
Technical field
The invention belongs to technical field of bioengineering, relate to the isolation technique of microbial fermentation solution, specially refer to and from microbial fermentation solution, separate 1, the method for ammediol.
Background technology
As everyone knows, 1, ammediol is a kind of important chemical material, with ethylene glycol, 1,2-propylene glycol and 1, the 4-butyleneglycol has same purposes, but it and terephthalic acid synthetic new polyester material polytrimethylene terephthalate (PTT) have the not available good characteristic of many polyester materials, good continuous printing and dyeing that present as need not to add any speciality chemical in the tint permanence of recovery of elasticity, uvioresistant, ozone and the oxynitride of nylon sample, low static, low water absorption, the panchromatic scope and biodegradable etc.These have all shown 1, the application prospect that ammediol is fine, but its expensive price has hindered its application.Since fermentative Production 1, ammediol become may since, researcher makes great efforts to explore a separation method of not only having saved trouble but also can reduce cost always.
Extraction separation 1 from microbial fermentation solution at present, ammediol, adopt carried disease germs fermented liquid through high speed centrifugation or through film (as tunica fibrosa) filtering separation cell more, extract as DE863632397 and US5008473, molecular sieve such as WO0125178 or vacuum distillation method purification 1, ammediol by extraction agent then.In the above-mentioned technology, high speed centrifugation not only energy consumption is higher, and separating power is limited.For the production of large industrial chemicals, the shortcoming that membrane filtration separate to exist is that cost is higher, and separating power is less, and disengaging time is long, and working pressure is higher, and is prone to problem such as film polluted membrane obstruction.In fermented liquid, directly add flocculating aids/flocculation agent, help to precipitate part thalline, nucleic acid and albumen, but the salt in the fermented liquid can crystallization and separate out, and still can form viscous substance in vacuum distillation process, hinders 1, the evaporation of ammediol.People Biotechnology Progress such as Baltycka (2000,16:76-79) open report adopts reaction, extraction, its general step is, in fermented liquid, add aldehyde, make 1, ammediol and aldehyde condensation, slough in the organic phase behind the water, with o-Xylol or toluene or ethylbenzene extraction, obtain 1 by hydrolysis then, ammediol.As seen, the operation of reaction, extraction arts demand multistep causes separation efficiency lower thus, the operating procedure complexity, and problems such as the difficult control of operational condition are promoted industry and are acquired a certain degree of difficulty, and research in this respect at present still is in laboratory stage.People such as Malinowski are at Biotechnology Progress (1999,13 (2): 127-30) report adopts the liquid-liquid extraction method, but also have with a certain distance from industrialization at present, the problem of existence is that extraction efficiency is lower, and the extraction agent that specificity is strong is selected comparatively difficulty.
Summary of the invention
The objective of the invention is at present fermentative Production 1, some problems that exist in the technology of ammediol later separation purified product, as the cost height, separating power is little, and the underpressure distillation later stage salt crystallization and viscous substance occur and hinder problems such as cut evaporation, and propose a kind ofly from fermented liquid, to separate 1, the effective ways of ammediol, make Production by Microorganism Fermentation 1, ammediol technically, viable economically.
Technical solution of the present invention is:
1) germ-carrying fermented liquid direct evaporation is concentrated to 1/2～1/20 of original fermented solution volume, collects steam simultaneously, condensation is used for preparing substratum or alkali lye;
2) after the concentrated solution cooling that step 1) is obtained, add ethanol or methyl alcohol, n-propyl alcohol, Virahol, acetone, butanone etc. by 1: 0.3～1: 5 volume ratio, pass through natural subsidence or filtration then or, get supernatant liquor less than 1000～4500 rpms of centrifugation throw outs;
3) with step 2) precipitation that obtains, add above-mentioned same alcohol or ketone by 1: 1～1: 10 volume ratio, stir washing precipitation.By natural subsidence or filtration or 1000～4500 rpms of centrifugation throw outs, get supernatant liquor then;
4) with step 2) and the mixing of step 3) gained supernatant liquor, alcohol or ketone reclaimed by distillation or rectifying;
5) solution with the step 4) gained is rich in 1, the cut of ammediol by the underpressure distillation collection; Step 4) and step 5) can be carried out in same device.
Effect of the present invention and benefit are:
Overcome extraction separation 1 from microbial fermentation solution at present, many drawbacks that ammediol technology exists are simplified technology, and cost reduces, economically feasible.Be in particular in: the fermented liquid that carries disease germs directly concentrates and has solved present high speed centrifugation and membrane sepn energy consumption height, shortcomings such as the low and complex process of separating power; To steam water and collect and to be used for preparing substratum and alkali lye, conserve water resource not only, and with evaporation carry secretly 1, ammediol is reclaimed, and has reduced product losses; Add alcohol (or ketone) and not only thalline is separated with fermented liquid, and fermented liquid amplifying nucleic acid, albumen and part salt are precipitated, the salt crystallization and the viscous substance that have also solved the appearance of underpressure distillation later stage simultaneously influence 1, problems such as ammediol evaporation.
Embodiment
Below be described in detail technical solution of the present invention and specific embodiment.
Step 1
Germ-carrying fermented liquid direct evaporation is concentrated to 1/2～1/20 of original fermented solution volume, collects steam simultaneously, condensation is used for preparing substratum or alkali lye, evaporation operation can be single-action also can be multiple-effect;
Step 2
The concentrated solution that step 1) is obtained is through nature or after forcing cool to room temperature, add ethanol or methyl alcohol, propyl alcohol, Virahol, acetone, butanone etc. by 1: 0.3～1: 5 volume ratio, stirred 10～30 minutes, left standstill 3～12 hours, pass through natural subsidence or filtration then or, get supernatant liquor less than 1000～4500 rpms of centrifugation throw outs;
Step 3
With step 2) precipitation that obtains, add above-mentioned same alcohol or ketone by 1: 1～1: 10 volume ratio, to stir 10～30 minutes, washing precipitation by natural subsidence or filtration or 1000～4500 rpms of centrifugation throw outs, is got supernatant liquor then;
Step 4
With step 2) and the mixing of step 3) gained supernatant liquor, reclaim alcohol or ketone by distillation or rectifying, distillation or rectifying can be operated under normal pressure or decompression;
Step 5
The solution of step 4) gained is rich in 1, the cut of ammediol by the underpressure distillation collection; Step 4) and step 5) can be carried out in same device.
Embodiment:
Used fermented liquid is to adopt Cray Bai Shi bacillus (Klebsiella pneumoniae) batch formula stream glycerol adding fermentative production 1 in the present embodiment, and ammediol is resulting, wherein 1, and the concentration of ammediol is 63g/l.
Cray Bai Shi bacillus (K.pneumoniae) is available from Chinese common micro-organisms DSMZ (CGMCC), culture presevation number: 1.1736.
Sepn process divided for five steps:
1) fermented liquid of getting 350ml carries out underpressure distillation at Rotary Evaporators, and vacuum tightness is 0.088MPa, and≤75 ℃ of temperature controls are concentrated to 60～80ml;
2) leave standstill cool to room temperature after, add 140ml 95% industrial alcohol, stir and left standstill 5 hours after 15 minutes, centrifugal 10 minutes again, get supernatant liquor at 3000rpm;
3) throw out is added 70ml 95% industrial alcohol, stir after 15 minutes, at 3000rpm centrifugal 10 minutes, get supernatant liquor;
4) first two steps gained supernatant liquor is mixed, through underpressure distillation, vacuum tightness is 0.088MPa in water-bath, and ethanol is reclaimed in≤75 ℃ of temperature controls;
5) by underpressure distillation, vacuum tightness is 0.088MPa, in oil bath, collect 160～185 ℃ be rich in 1, the cut of ammediol.The purity of products obtained therefrom is 99%, and the rate of recovery is 85%.
Claims (1)
1, extraction separation 1 in the microbial fermentation solution, the method of ammediol is at present fermentative Production 1, ammediol later separation purifying 1, problem that exists in the method for ammediol such as cost height, separating power is little, and the underpressure distillation later stage salt crystallization and viscous substance occur and hinder evaporation etc., and propose a kind ofly from fermented liquid, to separate 1, the method of ammediol, make microbial fermentation produce 1, ammediol technically, viable economically, it is characterized in that:
1) germ-carrying fermented liquid direct evaporation is concentrated to 1/2～1/20 of original fermented solution volume;
2) after the concentrated solution cooling that step 1) is obtained, add ethanol or methyl alcohol, n-propyl alcohol, Virahol, acetone, butanone etc. by 1: 0.3～1: 5 volume ratio, by natural subsidence or filtration or 1000～4500 rpms of centrifugation throw outs, get supernatant liquor then;
3) with step 2) precipitation that obtains, add above-mentioned same alcohol or ketone by 1: 1～1: 10 volume ratio, to stir, washing precipitation by natural subsidence or filtration or 1000～4500 rpms of centrifugation throw outs, is got supernatant liquor then;
4) with step 2) and the mixing of step 3) gained supernatant liquor, alcohol or ketone reclaimed by distillation or rectifying.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031335845A CN1190400C (en) | 2003-06-02 | 2003-06-02 | Method for extracting and separating 1,3-propylene glycol from microbial fermented liquor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB031335845A CN1190400C (en) | 2003-06-02 | 2003-06-02 | Method for extracting and separating 1,3-propylene glycol from microbial fermented liquor |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1460671A true CN1460671A (en) | 2003-12-10 |
| CN1190400C CN1190400C (en) | 2005-02-23 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB031335845A Expired - Fee Related CN1190400C (en) | 2003-06-02 | 2003-06-02 | Method for extracting and separating 1,3-propylene glycol from microbial fermented liquor |
Country Status (1)
| Country | Link |
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| CN (1) | CN1190400C (en) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006006981A1 (en) * | 2004-06-21 | 2006-01-19 | Lyondell Chemical Technology, L.P. | Removal of propylene glycol and propylene glycol ethers from aqueous streams |
| CN100355899C (en) * | 2006-04-14 | 2007-12-19 | 清华大学 | Pretreatment method for filtering fermentation liquor of bacteria of possessing capsula |
| WO2011076690A1 (en) | 2009-12-22 | 2011-06-30 | Metabolic Explorer | Method for purifying 1,2-propanediol from a fermentation broth |
| CN102625845A (en) * | 2009-09-09 | 2012-08-01 | 基因组股份公司 | Microorganisms and methods for the co-production of isopropanol with primary alcohols, diols and acids |
| WO2012130316A1 (en) | 2011-03-31 | 2012-10-04 | Metabolic Explorer | Method for purifying mpg (monopropylene glycol) from a fermentation broth |
| CN101830777B (en) * | 2010-02-07 | 2012-12-26 | 大连理工大学 | Method for recovering carbon dioxide by salting and extracting dihydric alcohol in fermentation liquor by coupling |
| CN101875598B (en) * | 2009-04-30 | 2013-11-06 | 中国石油天然气股份有限公司 | Separation method of 1, 3-propylene glycol fermentation liquor |
| WO2014051448A1 (en) | 2012-09-28 | 2014-04-03 | Prochimia Surfaces Sp. Z O.O. | A method for isolation of propane-1,3-diol from post-fermentation broth obtained by bioconversion |
| EP3085683A1 (en) * | 2006-02-10 | 2016-10-26 | DuPont Tate & Lyle Bio Products Company, LLC | Bio-derived 1,3-propanediol as natural and non irritating solvents for biomass-derived extracts, fragrance concentrates, and oils |
| CN106673995A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Method for refining long-chain dicarboxylic acids |
| CN106673996A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Method for purifying long-chain dicarboxylic acid |
| CN113773174A (en) * | 2021-09-15 | 2021-12-10 | 花安堂生物科技集团有限公司 | Method for simultaneously extracting dihydric alcohol and organic acid ester from microbial fermentation broth |
-
2003
- 2003-06-02 CN CNB031335845A patent/CN1190400C/en not_active Expired - Fee Related
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100519427C (en) * | 2004-06-21 | 2009-07-29 | 利安德化学技术有限公司 | Removal of propylene glycol and propylene glycol ethers from aqueous streams |
| WO2006006981A1 (en) * | 2004-06-21 | 2006-01-19 | Lyondell Chemical Technology, L.P. | Removal of propylene glycol and propylene glycol ethers from aqueous streams |
| EP3085683A1 (en) * | 2006-02-10 | 2016-10-26 | DuPont Tate & Lyle Bio Products Company, LLC | Bio-derived 1,3-propanediol as natural and non irritating solvents for biomass-derived extracts, fragrance concentrates, and oils |
| CN100355899C (en) * | 2006-04-14 | 2007-12-19 | 清华大学 | Pretreatment method for filtering fermentation liquor of bacteria of possessing capsula |
| CN101875598B (en) * | 2009-04-30 | 2013-11-06 | 中国石油天然气股份有限公司 | Separation method of 1, 3-propylene glycol fermentation liquor |
| CN102625845A (en) * | 2009-09-09 | 2012-08-01 | 基因组股份公司 | Microorganisms and methods for the co-production of isopropanol with primary alcohols, diols and acids |
| WO2011076690A1 (en) | 2009-12-22 | 2011-06-30 | Metabolic Explorer | Method for purifying 1,2-propanediol from a fermentation broth |
| CN101830777B (en) * | 2010-02-07 | 2012-12-26 | 大连理工大学 | Method for recovering carbon dioxide by salting and extracting dihydric alcohol in fermentation liquor by coupling |
| WO2012130316A1 (en) | 2011-03-31 | 2012-10-04 | Metabolic Explorer | Method for purifying mpg (monopropylene glycol) from a fermentation broth |
| WO2014051448A1 (en) | 2012-09-28 | 2014-04-03 | Prochimia Surfaces Sp. Z O.O. | A method for isolation of propane-1,3-diol from post-fermentation broth obtained by bioconversion |
| CN104640993A (en) * | 2012-09-28 | 2015-05-20 | 普罗奇米尔表面有限公司 | A method for isolation of propane-1,3-diol from post-fermentation broth obtained by bioconversion |
| US9434667B2 (en) | 2012-09-28 | 2016-09-06 | Prochimia Surfaces SP. Z.o.o. | Method for isolation of 1,3-propanediol from post-fermentation broth obtained by bioconversion |
| CN106673995A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Method for refining long-chain dicarboxylic acids |
| CN106673996A (en) * | 2015-11-09 | 2017-05-17 | 中国石油化工股份有限公司 | Method for purifying long-chain dicarboxylic acid |
| CN113773174A (en) * | 2021-09-15 | 2021-12-10 | 花安堂生物科技集团有限公司 | Method for simultaneously extracting dihydric alcohol and organic acid ester from microbial fermentation broth |
Also Published As
| Publication number | Publication date |
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| CN1190400C (en) | 2005-02-23 |
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