CN1071951A - The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid - Google Patents
The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid Download PDFInfo
- Publication number
- CN1071951A CN1071951A CN91109895A CN91109895A CN1071951A CN 1071951 A CN1071951 A CN 1071951A CN 91109895 A CN91109895 A CN 91109895A CN 91109895 A CN91109895 A CN 91109895A CN 1071951 A CN1071951 A CN 1071951A
- Authority
- CN
- China
- Prior art keywords
- grams per
- normal paraffin
- acid
- fermentation
- per liter
- 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.)
- Pending
Links
Abstract
The present invention is an asynchronous microbiological fermentative production long-chain alpha.The method of omega-dibasic acid.The microorganism of adopting is a not exclusively blocking-up type polyploid dissociant of candida tropicalis (Candidatropicalis).Characteristics are, after microbial strains was inserted fermented liquid, hierarchy of control pH when bacterium in the substratum is dense when reaching 7-12% (wet bacterium is heavy), added a certain amount of normal paraffin and emulsifying agent between 4.0～6.0, and regulation system pH to 7.0～8.0, begins fermentation.When present method is used for positive structure tridecane hydrocarbon fermentation and produces tridecanyldicarboxylic acid, fermented 72 hours, produce sour amount and can reach 100.1 grams per liters, fermented 120 hours, produce sour amount and can reach 144.4 grams per liters.
Description
The present invention relates to a kind of method of utilizing microbial fermentation normal paraffin production long-chain alpha omega-dibasic acid.
The long-chain alpha omega-dibasic acid is a class important chemical material.Can be used to synthetic senior spices, engineering plastics, hot melt adhesive, resin, senior lubricant additive, food preservatives etc.Particularly α ω-tridecanyldicarboxylic acid and 16-dicarboxylic acid, they are respectively the important source material of synthetic undecane dicarboxylic acid ethylene ester and exaltone.
Since the seventies, it is that matrix utilizes microbial fermentation to produce the research of long-chain biatomic acid that various countries have carried out in succession with the normal paraffin.Nineteen eighty-two Nippon Mining Co., Ltd.'s industry that takes the lead in is amplified, and builds up the device of producing 200 tons of tridecanyldicarboxylic acids per year in 1984, and has put into production.Chinese patent 87105445.0 has proposed the method for production long-chain alpha alpha, omega-dicarboxylic acid, the method for particularly producing α ω-16 carbon dicarboxylic acid.In 16 liters of fermentor tanks, normal cetane hydrocarbon input amount is 20%, and fermented liquid PH is controlled at 6.8～7.3, ferments 70 hours, produces the acid amount and reaches 77.5 grams per liters, prolongs fermentation time to 117 hour, produces the acid amount and reaches 123 grams per liters, and transformation efficiency is 79%.U.S. Pat 4,339,536 have also proposed to produce the method for long-chain biatomic acid, it is to be that 120 liters of addings of seed liquor of 10-15 grams per liter contain in the fermenter of 1200 liters of 240 liters of positive structure tridecane hydrocarbon and substratum with bacterial classification concentration, sterile air feeding amount is 400 liters/minute, be to cultivate after 12 hours under 5 the condition at 32 ℃ of temperature, PH, regulate PH to 7.0, and cultivated again 72 hours, obtain containing 1200 liters of fermented liquids of tridecanyldicarboxylic acid 40 grams per liters, positive structure tridecane hydrocarbon 8 grams per liters and thalline 20 grams per liters at last.
The objective of the invention is to propose a kind of method of utilizing asynchronous microbiological fermentation carbon atom quantity for the α omega-dibasic acid of the method, particularly high yield 12-16 carbon atom of the normal paraffin production long-chain alpha omega-dibasic acid of 11-18.
The used microorganism of the present invention is a not exclusively blocking-up type polyploid dissociant of candida tropicalis (Candlda troplcalls).It is through ultraviolet ray repeatedly mutagenic and breeding and the screening of rejuvenation regularly and the high yield diprotic acid produce bacterial strain, particularly extremely strong to the throughput of α ω-tridecanyldicarboxylic acid, SL-AH.It has two terminal omega oxidation normal paraffin abilities strong, the characteristics that assimilation normal paraffin and β-Yang Hua ability are weak.
The present invention utilizes above-mentioned bacterial classification, is main substrate with bacterial classification concentration as fermentation controlling index, employing alkane and saccharic, and be equipped with the fermentation of other nutrition component, by adding normal paraffin and alkyl phosphate, the operational condition of control cultivation stage and fermentation stage, growth and fermentation are carried out in two steps, to obtain the long-chain alpha omega-dibasic acid of high yield.
To connect by the bacterial classification of solid slant culture in people's seed substratum and cultivate, cultivate the back as fermentation seed liquid.According to certain input amount the fermentation seed liquid access is contained in the mixed solution of normal paraffin and fermention medium, begin to stir, controlled temperature, PH, regulate the nutrient solution pH value with acid solution simultaneously and be acid, carry out culture of strains and breeding, in the spawn culture stage, the α omega-dibasic acid generates few, and growth and breeding are rapid, after treating that bacterial classification reaches finite concentration, begin to add an amount of normal paraffin and alkyl phosphate, regulate nutrient solution PH with alkali lye and be alkalescence, begin to change over to fermentation stage, carry out the accumulation of diprotic acid.The diprotic acid that generates then is dissolved in the fermented liquid with the form of metal-salt.After the fermentation ends,, make purified long-chain alpha omega-dibasic acid through acidifying and separating treatment.
Bacterium culture medium of the present invention has the wort of (1) 6 degree Beaume to add the solid inclined-plane that 2% agar is made.(2) alkane liquid nutrient medium.
The alkane liquid nutrient medium consists of: Na
2HPO
412H
2O 4-6 grams per liter, KH
2PO
4The 2-4 grams per liter, MgSO
47H
2The O0.5-3 grams per liter, NaCl 1-3 grams per liter, sucrose 15-30 grams per liter, yeast extract paste 0.5-2 grams per liter, corn steep liquor 0.5-2 grams per liter, urea 0.5-3 grams per liter, VITMAIN B1 0.1-0.3 grams per liter, normal paraffin 50-80 milliliter/liter and prepare from water.After the preparation of alkane liquid nutrient medium, need its PH is transferred to about 4.5.
Cultivating the bacterial classification process is: (1) gets the full incomplete blocking-up type polyploid of a transfering loop candida tropicalis dissociant, is coated on the wort solid inclined-plane.Wort solid inclined-plane specific practice is with the wort of 6 degree Beaume and 2% agar heating for dissolving, and in the glass test tube of the φ 25 * 210mm that packs into then, every cuvette cartridge liquid measure is the 8-10 milliliter, puts into the inclined-plane, can use behind the solid inclined-plane that congeals into.The bacterial classification that is coated on the wort solid inclined-plane was cultivated 48 hours down at 30～32 ℃.(2) get a bacterial classification on the above-mentioned inclined-plane and be linked into through 600 milliliters/3000 milliliters bottoms of sterilization and have in the alkane substratum of six baffle flasks, on 180 rev/mins rotary shaker, cultivating 48 hours under 30-32 ℃, as fermented bacterium.
In the alkane fermenting process, when culture propagation arrives finite concentration, will improve the pH value of fermented liquid, make it to help fermentation and acid.Regulate PH prematurely, bacterial classification concentration is too low, and the acid amount is produced in influence, regulates pH value excessively lately, can shorten relatively again and produce the acid time.When transmitting ferment, have only bacterial classification to reach finite concentration, could obtain higher product acid amount.The suitable concentration of bacterial classification is 2.0-6.0 * 10 when transmitting ferment
8The wet bacterium of individual bacterial classification/milliliter or 7-12%(is heavy), 8-10% preferably.Obtain to transmit the required above-mentioned bacterial classification concentration of ferment at short notice, preferably the nutrient solution pH value is transferred and be acid at cultivation stage, suitable pH value is 4.0-6.0, preferably be controlled at 4.5 ± 0.1, this moment, diprotic acid generated few, and bacterial classification consumption saccharic is grown fast and is bred, and in 12-36 hour, just can reach and transmit the required bacterial classification concentration of ferment.
Adding emulsifying agent is crucial to bacterial classification with fully contacting of alkane.Add an amount of emulsifying agent and can improve the micronize degree of alkane.Alkyl phosphate is an ideal emulsifying agent comparatively.Add an amount of alkyl phosphate and can promote to produce the increase that acid is measured, particularly the product acid amount to SL-AH and tridecanyldicarboxylic acid increases comparatively obvious.Its suitable content in fermented liquid is the 1-5 grams per liter, preferably the 1-3 grams per liter.Add alkyl phosphate and preferably carry out when changing fermentation over to, it can add separately, also can add in the fermented liquid with alkane.
At cultivation stage, the suitable input amount of normal paraffin is 2-15%(v/v, accounts for total fermentating liquid volume), 5-10%(v/v preferably).The carbonatoms of normal paraffin is 11-18, and it is better to contain 12-16 carbon atomic ratio, but preferably contains 13 carbon atoms, secondly is to contain 12 carbon atoms.Fermentation stage, the suitable additional amount of normal paraffin is 15-30%(v/v, accounts for total fermentating liquid volume), it adds the same cultivation stage of carbonatoms situation of normal paraffin, and best additional amount is 20-25%.
Bacterial classification through the cultivation of cultivation stage, when its concentration reaches 7-12%, begins to add 15-30%(v/v under acidic conditions) normal paraffin and an amount of alkyl phosphate, then, little by little regulate fermentating liquid PH value, the adjusting time is 0.5-4.5 hour, preferably 3.5-4.5 hour.At last pH value is transferred to 7.0-8.0, preferably be controlled at 7.8 ± 0.1.
Cultivation stage after strain liquid inserts is used acid solution, and as 6N sulfuric acid, regulating nutrient solution PH is 4.0-6.0.Bacterial classification still wants metabolism to generate a spot of α omega-dibasic acid in growth and reproductive process, and pH value descends, and uses alkali lye, as 12N sodium hydroxide or potassium hydroxide, regulates, and makes PH maintain 4-6.During the fermentation, because a large amount of α omega-dibasic acid accumulation are arranged, PH descends, and regulates PH and maintains 7.0-8.0 with above-mentioned alkali lye, until fermentation ends.
In polynary substrate, normal paraffin and sucrose are main carbon sources, and sucrose is used for keeping the growth and the breeding of bacterial classification as carbon source, and normal paraffin is the corresponding matrix of purpose meta-bolites.The suitable content of sucrose is the 20-30 grams per liter in the fermention medium.Magnesium ion is the activator of plurality of enzymes, and an amount of magnesium ion concentration is very favourable to producing diprotic acid, and particularly to producing the α omega-dibasic acid of carbon number 12 to 15, it is particularly important to add magnesium ion.Suitable MgSO
47H
2O content is the 0.5-2.5 grams per liter, preferably the 1.0-2.0 grams per liter.Add an amount of VITMAIN B1 to the growth of bacterial classification with ferment favourablely, optimum content is the 0.1-0.2 grams per liter.Suitable urea content can improve the rate of propagation of bacterial classification, enters growth stationary phase in advance, prolongs effectively and produces the acid phase.Content of urea is the 1-2 grams per liter preferably.
All add liquid or stream liquid feeding and bacterium culture medium, fermention medium is in 0.1MPa, 121 ℃ of sterilization uses after 20-30 minute down.The normal paraffin purity that contains 11-18 carbon atom is greater than 97%, and the long-chain alpha omega-dibasic acid that contains 11-18 carbon atom is made qualitative and quantitative analysis with vapor-phase chromatography.
Can finish the present invention by following step:
(1) get a transfering loop bacterial classification and do slant culture, incubation time is 48 hours, 32 ℃ of temperature.
(2) bacterial classification with slant culture inserts in the alkane substratum, cultivates 48 hours, and 32 ℃ of temperature are as seed liquor.
(3) seed liquor is inserted in the fermentor tank, or after 1-3 level seed culture, ferment in the access fermentor tank again.
With fermented bacterium by 5-30%(v/v) input amount insert contain 2-15%(v/v) the normal paraffin and fermention medium mixed solution of 11-18 carbon atom in, PH transfers to 4.0-6.0 with mixed solution, cultivate under optimum conditions, it is heavy to treat that bacterial classification concentration reaches the wet bacterium of 7-12%() time, add 15-30%(v/v) above-mentioned alkane and alkyl phosphate, the content of alkyl phosphate is the 1-5 grams per liter, regulate fermentating liquid PH value gradually to 7.0-8.0 with alkali lye, and keep 7.0-8.0 to fermentation ends, through heating, breakdown of emulsion, divide oil, crystallization, recrystallization promptly gets α omega-dibasic acid product.
The normal paraffin that present method contains 11-18 carbon atom with the incomplete blocking-up type polyploid dissociant fermentation of candida tropicalis (Candlda troplcalls) obtains the α omega-dibasic acid of corresponding carbon number.Produce α ω-tridecanyldicarboxylic acid with the 3 cubic metres of positive structure tridecane of ferment tank hydrocarbon.Cultivation stage, positive structure tridecane hydrocarbon input amount is 5%(v/v), PH is 4.5 ± 0.1, cultivates 24 hours bacterial classification concentration and reaches the wet bacterium of 8%(heavily), begin to add 20%(v/v) above-mentioned alkane and an amount of alkyl phosphate, regulating PH is 7.8 ± 0.1, changes fermentation over to, ferments 48 hours, produce the acid amount and reach 100.1 grams per liters, extend to 96 hours, produce the acid amount and reach 144.4 grams per liters, transformation efficiency is 82.9%.Reach 120 grams per liters at ferment respectively positive structure 12,16-dicarboxylic acid output of 3 liters of fermentor tanks, α ω-16-dicarboxylic acid output reaches 68.6 grams per liters.
Embodiment 1
(1) the incomplete blocking-up type polyploid dissociant of the candida tropicalis (Candlda troplcalls) of getting a transfering loop is coated on the solid inclined-plane that wort in φ 25 * 210mm glass test tube and 2% agar makes totally 4.Cultivated 48 hours down at 32 ℃.(2) with 4 slant strains of above-mentioned cultivation, inserting 4 respectively bottledly has the triangle that has six baffle plates through 3000 milliliters of bottoms of 600 milliliters of alkane substratum of sterilization to shake in the bottle, in 32 ℃, cultivates 48 hours on 180 rev/mins the rotary shaker.(3) two bottles one group of the strain liquid (about 1.2 liters) that (2) are cultivated in the culture tank that two groups are inserted 10 liters of two liquid amounts that 8.3 liters of 0.5 liter of positive structure tridecane hydrocarbon and substratum are housed respectively, is cultivated as first order seed totally.Substratum consists of: Na
2HPO
412H
2The O6 grams per liter, KH
2PO
42 grams per liters, NaCl1 grams per liter, sucrose 30 grams per liters, VITMAIN B1 0.1 grams per liter, yeast extract paste 1 grams per liter, corn steep liquor 1 grams per liter, urea 2 grams per liters, MgSO
47H
2The O1 grams per liter, this substratum water preparation.Positive structure tridecane hydrocarbon, urea, MgSO
47H
2O is sterilization separately respectively, adds before inoculation.Above-mentioned substrate sterilising conditions is 0.1MPa, 121 ℃ of water vapors, sterilization time 30 minutes.(4) after the inoculation, 32.5 ℃, PH4.5 ± 0.1,550 rev/mins of mixing speed, 8 liters/minute of air flows, tank pressure 0.02MPa cultivate bacterial classification down, and incubation time is 36 hours.(5) 20 liters of strain liquids that (4) are cultivated insert in 200 liters of gas stripping types that 8 liters of positive structure tridecane hydrocarbon and 132 liters of substratum are housed in the circulation incubator, in the cultivation 36 hours down of 32.5 ℃, PH4.5 ± 0.1,183 liters/minute of air flows, tank pressure 0.03MPa.Cultivate as secondary seed.(6) 160 liters of strain liquids that (5) are cultivated, access is equipped with in 800 liters of culture tank of 30 liters of positive structure tridecane hydrocarbon and 410 liters of substratum, and 200 rev/mins of mixing speed, air flow is 550 liters/minute, other condition is with cultivating 40 hours under the situation of (4), as three grades of seed culture.(7) 600 liters of strain liquids accesses of (6) cultivation are equipped with in 3 cubic metres of fermentor tanks of 1775 liters of 125 liters of positive structure tridecane hydrocarbon and substratum, under the operational condition of (6), cultivated 24 hours, it is heavy that bacterial classification concentration reaches the wet bacterium of 9.8%(), begin to add 500 liters of positive structure tridecane hydrocarbon and 2.5 kilograms of alkyl phosphates, progressively regulate fermentating liquid PH value to 7.8 ± 0.1 with the 12N sodium hydroxide solution, time is 4 hours, begins to change over to fermentation.Change fermentation (stream adds a small amount of glycerin polyether defoamer) secondary fermentation 48 hours over to, α ω-tridecanyldicarboxylic acid output reaches 100.1 grams per liters.Continued fermentation to 96 hours from 48 hours, produce the acid amount and reach 144.4 grams per liters, transformation efficiency is 82.9%.
Embodiment 2
(1) method is with embodiment 1(1), cultivate a slant strains.(2) method is with embodiment 1(2), cultivate one bottle of strain liquid (about 600 milliliters).The liquid amount that 150 milliliters of positive structure dodecane hydrocarbon and 2550 milliliters of fermention mediums are equipped with in 300 milliliters of accesses of strain liquid taking-up of (3) (2) being cultivated is in 3 liters of fermentor tanks of controlling automatically.Substratum composition and sterilising method and culture condition are with embodiment 1(3).Incubation time 40 hours, bacterial classification concentration reaches 8%, begins to add 600 milliliters of positive structure dodecane hydrocarbon and 3 gram alkyl phosphates, progressively regulates fermented liquid PH to 7.8 ± 0.1 with the 12N sodium hydroxide solution, 4.5 hours time, begins to change over to fermentation.Change fermentation secondary fermentation 70 hours over to, α ω-SL-AH output reaches 102 grams per liters, and transformation efficiency is 75%.
Embodiment 3
Method is with embodiment 2.Fermentation normal cetane hydrocarbon is produced α ω-16-dicarboxylic acid.Transmit ferment secondary fermentation 70 hours, α ω-16-dicarboxylic acid output reaches 68.6 grams per liters, and transformation efficiency is 56%.
Embodiment 4
Slant culture bacterial classification (1) and shake-flask culture bacterial classification (2) are with the method for (1) among the embodiment 1 and (2).(3) cultivate MgSO in the 10 liters of culture tank of seed liquor access with shake-flask culture
47H
2O content is 2 grams per liters, and other condition is with (3) among the embodiment 1.(4) after the inoculation, mixing speed is 600 rev/mins, and air flow is 6.5 liters/minute, and other condition is with (4) among the embodiment 1.(5) 20 liters of seed liquor that 10 liters of culture tank are cultivated insert in the interior circulation incubator of 200 liters of gas stripping types, and air flow is 150 liters/minute, cultivates 33 hours, and other condition is with (5) in the example 1.(6) 160 liters of seed liquor that (5) are cultivated insert in 800 liters of culture tank, and stirring velocity is 160 rev/mins, and air flow is 500 liters/minute, and other condition is with (6) among the embodiment 1.(7) 600 liters of seed liquor that (6) are cultivated insert in 3 cubic metres of fermentor tanks, cultivated 20 hours, bacterial classification concentration reaches 8.7%, and the alkyl phosphate of adding is 3.0 kilograms, with the 12N sodium hydroxide solution fermentating liquid PH value is progressively transferred to 7.8 by 4.5, the adjusting time is 4.5 hours.After changing fermentation over to, fermented 48 hours, produce the acid amount and reach 98.2 grams per liters, continue fermentation 72 hours, produce the acid amount up to 166.3 grams per liters, transformation efficiency is 84%.
Claims (10)
1, a kind of method of utilizing asynchronous microbiological fermentation normal paraffin production long-chain alpha omega-dibasic acid, fermented bacterium inserted in the mixed solution contain normal paraffin and fermention medium cultivate, at cultivation stage, regulate nutrient solution and be acid, make the bacterial classification ramp, when bacterial classification reaches finite concentration in short vegetative period, add normal paraffin and emulsifying agent, regulate nutrient solution and be alkalescence, change fermentation stage over to, until fermentation ends.It is characterized in that growth and produce acid and carry out in two steps.At cultivation stage, to contain culture of strains liquid pH value is controlled between 4.0～6.0, cultivate bacterial classification, the accumulation of α omega-dibasic acid is few, when bacterial classification concentration reaches 7-12% (wet bacterium is heavy), add a certain amount of normal paraffin and emulsifying agent, and progressively regulate between the medium pH value 7.0～8.0, change fermentation stage over to, begin to accumulate the long-chain alpha omega-dibasic acid under optimum conditions.
2, according to the method for claim 1, the bacterial classification concentration when it is characterized in that transmitting ferment preferably 8～10%.
3, according to the method for claim 1, it is characterized in that preferably alkyl phosphate of the emulsifying agent added, its suitable content is the 1-5 grams per liter, preferably the 1-3 grams per liter.
4,, it is characterized in that cultivation stage normal paraffin input amount is 2-15%(v/v according to the method for claim 1), the optimum input amount is 5～10%.Adding the normal paraffin amount is 15-30%(v/v), 20-25% preferably.
5, according to the method for claim 1, it is characterized in that cultivation stage nutrient solution pH value preferably is controlled at 4.5 ± 0.1, the fermentation stage fermentating liquid PH value preferably is controlled at 7.8 ± 0.1.
6, the method according to claim 1 is characterized in that said microorganism is that the diprotic acid that candida tropicalis belongs to is produced bacterium, the preferably incomplete blocking-up type polyploid of candida tropicalis dissociant.
7, according to the method for claim 1, it is characterized in that in the said fermention medium preferably 20-30 grams per liter of sucrose content, urea content is the 1-2 grams per liter preferably, vitamins B
1Content is the 0.1-0.2 grams per liter preferably, MgSO
47H
2O content is the 1-2 grams per liter preferably.
8, according to claim 1,4 method, it is characterized in that said normal paraffin contains 11-18 carbon atom.
9, according to the method for claim 1, it is better to it is characterized in that said normal paraffin contains 12-16 carbon atomic ratio.
10, according to claim 1,4 method, it is characterized in that said normal paraffin preferably contains 13 carbon atoms.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN91109895A CN1071951A (en) | 1991-10-29 | 1991-10-29 | The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN91109895A CN1071951A (en) | 1991-10-29 | 1991-10-29 | The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1071951A true CN1071951A (en) | 1993-05-12 |
Family
ID=4910041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN91109895A Pending CN1071951A (en) | 1991-10-29 | 1991-10-29 | The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1071951A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1053470C (en) * | 1997-04-04 | 2000-06-14 | 中国科学院微生物研究所 | Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously |
| CN101346470B (en) * | 2005-12-30 | 2011-11-23 | 科学与工业研究委员会 | Method for preparing long chain dicarboxylic acid |
| CN103717745A (en) * | 2011-08-15 | 2014-04-09 | 丰田自动车株式会社 | Method for producing alkane and recombinant microorganism having alkane-synthesizing ability |
| CN103805643A (en) * | 2012-11-07 | 2014-05-21 | 中国石油化工股份有限公司 | Production method for long-chain dicarboxylic acids |
| CN107312804A (en) * | 2017-07-21 | 2017-11-03 | 张艾琳 | A kind of biofermentation new method of positive long-chain tridecanyldicarboxylic acid |
| EP3533879A1 (en) | 2018-03-01 | 2019-09-04 | Cathay R&D Center Co., Ltd. | Method for producing a long chain dicarboxylic acid by fermentation |
| EP3550014A1 (en) | 2018-04-04 | 2019-10-09 | Shanghai Cathay Biotech R&D Center Ltd. | Directed evolution of cyp52a12 gene and its use in dicarboxylic acid production |
| CN111100884A (en) * | 2018-10-26 | 2020-05-05 | 中国石油化工股份有限公司 | Method for preparing long-chain dicarboxylic acid by fermentation |
-
1991
- 1991-10-29 CN CN91109895A patent/CN1071951A/en active Pending
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1053470C (en) * | 1997-04-04 | 2000-06-14 | 中国科学院微生物研究所 | Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously |
| CN101346470B (en) * | 2005-12-30 | 2011-11-23 | 科学与工业研究委员会 | Method for preparing long chain dicarboxylic acid |
| CN103717745A (en) * | 2011-08-15 | 2014-04-09 | 丰田自动车株式会社 | Method for producing alkane and recombinant microorganism having alkane-synthesizing ability |
| CN103717745B (en) * | 2011-08-15 | 2016-04-27 | 丰田自动车株式会社 | The manufacture method of alkane and there is the recombinant microorganism of alkane synthesis capability |
| CN103805643A (en) * | 2012-11-07 | 2014-05-21 | 中国石油化工股份有限公司 | Production method for long-chain dicarboxylic acids |
| CN103805643B (en) * | 2012-11-07 | 2016-04-27 | 中国石油化工股份有限公司 | A kind of method of producing long-chain biatomic acid |
| CN107312804A (en) * | 2017-07-21 | 2017-11-03 | 张艾琳 | A kind of biofermentation new method of positive long-chain tridecanyldicarboxylic acid |
| EP3533879A1 (en) | 2018-03-01 | 2019-09-04 | Cathay R&D Center Co., Ltd. | Method for producing a long chain dicarboxylic acid by fermentation |
| US20190271012A1 (en) * | 2018-03-01 | 2019-09-05 | Cathay R&D Center Co., Ltd. | Method for producing a long chain dicarboxylic acid by fermentation, fermentation broth, treated fermentation broth and wastewater |
| US11319561B2 (en) * | 2018-03-01 | 2022-05-03 | Cathay Biotech Inc. | Method for producing a long chain dicarboxylic acid by fermentation, fermentation broth, treated fermentation broth and wastewater |
| EP3550014A1 (en) | 2018-04-04 | 2019-10-09 | Shanghai Cathay Biotech R&D Center Ltd. | Directed evolution of cyp52a12 gene and its use in dicarboxylic acid production |
| CN111100884A (en) * | 2018-10-26 | 2020-05-05 | 中国石油化工股份有限公司 | Method for preparing long-chain dicarboxylic acid by fermentation |
| CN111100884B (en) * | 2018-10-26 | 2022-03-08 | 中国石油化工股份有限公司 | Method for preparing long-chain dicarboxylic acid by fermentation |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Bornstein et al. | The nutrition of Clostridium kluyveri | |
| CN101353636B (en) | Production method of lactobacillus micro-ecological preparation for cultivation water regulation | |
| CN110218745A (en) | The method of fermenting and producing long-chain biatomic acid and its obtained long-chain biatomic acid | |
| Mostafa | Production and recovery of volatile fatty acids from fermentation broth | |
| CN110218661A (en) | A kind of Candida tropicalis and its application and a kind of production method of long-chain biatomic acid | |
| CN1071951A (en) | The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid | |
| CN111500464A (en) | Method for producing lutein by first mixotrophic-later autotrophic microalgae | |
| CN1026129C (en) | Process for producing long-chain alpha, omega-dicarboxylic acid from orthoalkanes by microbe fermentation | |
| CN102115768B (en) | Method for producing hexadecanedioic acid by synchronously fermenting n-hexadecane with microbe | |
| Ko et al. | Transient kinetics of yeast growth in batch and continous culture with an inhibitory carbon and energy source | |
| Hitschmann et al. | Oxygen deficiency and its effect on the adenylate system in Acetobacter in the submerse acetic fermentation | |
| CN112266946B (en) | Mixed nitrogen source for tetracycline fermentation and application method thereof in tetracycline fermentation | |
| CN1141733A (en) | Application method of rare earth in feed microbe | |
| Malek et al. | Continuous cultivation of microorganisms | |
| CA2521419A1 (en) | Fermentation processes with low concentrations of carbon-and nitrogen-containing nutrients | |
| RU1243354C (en) | Method of obtaining lactic acid | |
| US4752584A (en) | Process for the production of inoculum for anaerobic fermentation of coenzyme B12 | |
| RU2138549C1 (en) | Method of microorganism biomass preparing | |
| SU955683A1 (en) | Method of producing acetic acid | |
| SU506613A1 (en) | The method of obtaining biomass | |
| CN117778292A (en) | Method for improving fermentation yield of L-isoleucine | |
| SU618407A1 (en) | Method of producing crop | |
| Málek et al. | Continuous cultivation of microorganisms: A review | |
| Málek et al. | Continuous cultivation of microorganisms: A review | |
| RU2125608C1 (en) | Method of l-lysine producing |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |