CN1162644A - Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously - Google Patents
Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously Download PDFInfo
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- 239000002253 acid Substances 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000855 fermentation Methods 0.000 claims abstract description 22
- 230000004151 fermentation Effects 0.000 claims abstract description 22
- IIYFAKIEWZDVMP-UHFFFAOYSA-N tridecane Chemical compound CCCCCCCCCCCCC IIYFAKIEWZDVMP-UHFFFAOYSA-N 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 19
- 241000222178 Candida tropicalis Species 0.000 claims abstract description 9
- 230000001360 synchronised effect Effects 0.000 claims abstract description 4
- 150000007513 acids Chemical class 0.000 claims abstract description 3
- 239000011159 matrix material Substances 0.000 claims abstract description 3
- 230000001580 bacterial effect Effects 0.000 claims description 9
- 150000007520 diprotic acids Chemical class 0.000 claims description 8
- 244000005700 microbiome Species 0.000 claims description 6
- 150000001335 aliphatic alkanes Chemical class 0.000 abstract description 16
- 239000001963 growth medium Substances 0.000 abstract description 9
- 102100022210 COX assembly mitochondrial protein 2 homolog Human genes 0.000 abstract 4
- 101000900446 Homo sapiens COX assembly mitochondrial protein 2 homolog Proteins 0.000 abstract 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 abstract 2
- 230000000869 mutational effect Effects 0.000 abstract 1
- 239000007788 liquid Substances 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
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Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
A synchronous microbe fermentation process for producing hendecane 1,11-dicarboxylic acid (DC13) with high output from n-tridecane (nC13) features that after the mutational strain resultant from Candidatropicalis is inoculated to culture medium whose matrix is different normal alkanes containing C11-C18, its main action is to grow thallus within 28 hrs, generating a certain quantity of biatomic acid by controlling pH value under 6.8, then to generate acid while growing a certain amount of thallus in 28-60 hrs by controlling pH value under 7.3, and finally to quickly generate different biatomic acids after 60 hrs by controlling pH value to 7.5-7.8. When the process is used to produce DC13 by fermentation in 2.5 cu.m fermentator, the DC13 content is high up to 205 g/l in 161 hrs, the transform rate is 94% and the purity of DC13 is 96-97%.
Description
The present invention relates to the method that the synchronous fermentation n-paraffins of microorganism is produced the long-chain alpha, omega-dibasic acid, n-tridecane (nC especially ferments
13) high yield undecane 1,11-dicarboxylic acid (DC
13) method.
C
10Above long-chain biatomic acid is a synthetic senior spices on the chemical industry, senior nylon engineering plastic, high-grade clothing nylon hot-melt adhesive, high temperature dielectric medium, high grade paint, the important source material of lubricating oil additive and cold-resistant plasticizer etc.Especially tridecanyldicarboxylic acid (DC
13) and 15 carbon dicarboxylic acid (DC
15), they are respectively the important source material of synthetic daily spices astrotone and famous and precious spices muskone.
C
10Above long-chain biatomic acid at occurring in nature Individual existence not, has only a few diprotic acid to split from vegetables oil to be situated between and produces, for example sebacic acid (DC
10) can split to be situated between from castor seeds oil and produce; DC
13Can from rapeseed oil, extracting go out the glycerine eruciate again with the production of ozone oxidation method; DC
15Can split to be situated between from the cranial nerve acid the malania oleifera oil and produce.But they all are subjected to the restriction of farmland and weather, far can not satisfy the demand.So far yet there are not economically viable synthetic route and method on the chemical industry.Microbiologist's applied bioengineering technology is utilized the diprotic acid of the normal paraffin production respective chain length in the microbial fermentation oil, has remedied the deficiency on the chemical industry, has opened up the new source of long-chain biatomic acid.
Before the seventies, the various countries scientist sends out the research that alcohol is produced diprotic acid to microorganism, only be in theoretical research stage, the diprotic acid that produces and accumulate also all is the following short chain diprotic acid of ten carbon, after the seventies, enter the applied research stage, by a large amount of induction mutation of bacterium screenings, cultivate a collection of new mutant bacterial strain, can be from ten long-chain biatomic acids that the normal alkane generation more than the carbon is identical with the matrix chain length with accumulation, and, make accumulation several grams from the outset of diprotic acid in every liter of fermented liquid by constantly cultivating and metabolic regulation is studied, tens grams, tens grams are brought up to about present more than 100 grams and two hectograms.
Since the eighties, the research of diprotic acid enters the Small Scale Industry production phase, and several patent documentations that have actual production to be worth occurred.Chinese patent 87105445.0, CN1046757A, CN1092108A and CN1130685A propose to produce the method for long-chain alpha, omega-dibasic acid respectively, particularly distinguish high yield DC
16, DC
17, DC
15And DC
12Method.In 16 liters of automatic controlling tank, fermented DC 5 days
16Be 123g/L, fermented DC 6 days
17Be 133g/L, at 2.5m
3In the general form fermentor tank, fermented DC 6 days
15Be 178g/L, at 3m
3In the fermentor tank, send out alcohol 5 days, DC
12Be 145g/L.
To DC
13Research, Nippon Mining Co., Ltd.'s industry that takes the lead in is amplified, and builds up in 1984 to produce 200 tons DC per year
13The industrial fermentation device, and put into production.Chinese patent CN1071951A proposes a kind of method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid, especially produces DC
13Method.Its method is to carry out in two steps, and according to experimental example 4, the first step is cultured 600 liters of strain liquids to be inserted n-tridecane (nC is housed
13) 3m of 1775 liters of 125 liters and substratum
3In the fermentor tank (being that liquid amount is 83%), PH is 4.5 ± 0.1 in control, and thalline is cultivated in breeding, and 24 hours, cell concentration reached 8.7% (wet bacterium is heavy); Second goes on foot, and adds the nC of 20% (V/V)
13, transfer PH to 7.8 ± 0.1, change the fermentation and acid stage over to, fermented DC 72 hours
13Reach 98.2g/L, continue fermentation 72 hours, produce acid and reach 166.3g/L (beginning to fermentation ends totally 168 hours from inoculation), transformation efficiency is 84%.
The objective of the invention is to propose another kind utilizes the synchronous fermentation n-paraffins of microorganism to produce C
11-C
18The method of long-chain alpha, omega-dibasic acid, especially high yield DC
13Method.
The used bacterial strain of the present invention is candida tropicalis (Candida tropicalis) P-12-242, be to produce the candida tropicalis of mixed dicarboxylic acid (referring to " microorganism journal " 20 (1): 88-93 with a strain oxidation normal alkane, 1980) be starting strain, by nitrous acid and ultraviolet repeatedly repeatedly mutagenesis screening cultivate, can be from C
11-C
18Various single normal alkane and mix normal alkane, especially n-tridecane, the dicarboxylic acid of high production ground production respective chain length.Candida tropicalis P-12-242 (hereinafter to be referred as P-12-242) is deposited in China Committee for Culture Collection of Microorganisms common micro-organisms center, and preserving number is: CGMCC NO..
The physiological property of P-12-242 is as follows:
One, the fermentation of carbohydrate: glucose+, semi-lactosi+, sucrose+, maltose+, lactose-.
Two, assimilation: glucose+, semi-lactosi+, sorbose-, sucrose+, maltose+,
Cellobiose+, trehalose+, lactose-, close disaccharides-, raffinose-, melizitose+,
Levulin-, Zulkovsky starch+, wood sugar+, the L-arabinose+, the D-arabinose-,
Ribose-, rhamnosyl-, α-Jia Jiputaotanggan+, glycerine+, ethanol+, tetrahydroxybutane-,
N.F,USP MANNITOL+, inositol-, the nuclear furfuryl alcohol+, melampyrum-, sorbitol+,
Trisodium Citrate-, Soduxin+, calcium lactate-.
Three, the needs of growth hormone: vitamin H ++, vitamins B
1++, vitamins B
2+,
Vitamins B
6+, vitamins B
12+, folic acid+, nicotinic acid+, pantothenic acid+, inositol+,
Para-amino benzoic acid+.
Four, other: nitrate-, freezing milk-, ursolic acid decomposes-, solidify milk-, the grease enzyme-.
Morphological specificity: creamy-white, gauffer type, bacterium colony are the crisp shape of cake shape and peach.
Cultural characteristic:
When cultivating in malt juice liquid medium, pseudohypha is many and grow; When in the alkane seed culture medium, cultivating, the short pseudohypha of some amount is arranged; And when fermenting in fermention medium, major part is a single ellipse garden cell.Seed culture medium of the present invention: the wort of (1), 10 Bahrain's pols adds the solid inclined-plane that 2% agar is made; (2), the malt juice liquid medium of 10 Bahrain; (3), the alkane seed culture medium comprises: KH
2PO
46-12g/L, corn steep liquor 3-8g/L, yeast extract paste 3-
8g/L, sucrose 3-8g/L, urea 3-6g/L, heavy wax 40-70ml/L, the tap water preparation,
Nature PH.
The process of cultivating seed is: get a transfering loop P-12-242 yeast thalline, be coated on by (15 * 180 test tubes, every dress 6-7mL substratum is put into the inclined-plane) on the wort solid inclined-plane, cultivated 40 hours in 28-30 ℃.Getting an above-mentioned cultured P-12-242 bacterial classification branch scrapes in the 250mL triangular flask that 25ml alkane seed culture medium is housed, on 28-30 ℃ 220 rev/mins rotary shaker, cultivated 40-48 hour, as the shake flask fermentation seed or get two above-mentioned cultured P-12-242 bacterial classifications and all scrape in the 5000ml triangular flask that the 500mL substratum is housed, on 180 rev/mins of rotary shakers, cultivated 44-48 hour for 28-30 ℃, as the seed of first class seed pot.
Produce long chain dicarboxylic acid with P-12-242 bacterial strain of the present invention, particularly the concrete grammar of 13 carbon dicarboxylic acid is: the seed of fermentation is inserted PH5.5-9.0, be preferably the C that contains 15-45% (V/V) of 6.5-7.5
11-C
18Normal alkane and the mixed solution of 85-55% (V/V) fermention medium in.Consisting of of fermention medium: alkali metal phosphate 6-14g/L, be preferably 7-10g/L, sodium-chlor 0.5-2.0g/L, yeast extract paste 1-6g/L, be preferably 3-5g/L, corn steep liquor 0.5-2g/L, urea 0.5-2.5g/L is preferably 1.0-2.0g/L, nitrate 5-15g/L, be preferably 6-12g/L, sucrose 10-30g/L is preferably 10-20g/L, froth breaking Liu 400-1200ppm and some other known nutrition sources, between PH5.8-7.5 with said mixture at 25-30 ℃, be preferably in 27-31 ℃ of aerobic fermentation 48-170 hour.In 28 hours, PH is controlled at below 6.8, based on thalli growth, produce acid for paying, this moment, strain growth optical density(OD) OD reached about 0.6, produced acid and reached 20-30g/L, at 28-60 hour, PH is controlled at below 7.3, and it is main producing acid, and thalli growth is for paying, this moment, OD reached to about 0.9, produce acid and reach 75-85g/L, after 60 hours, used N every 6-8 hour
aOH solution is transferred a PH to 7.5-8.0, and biomass no longer increases, and continues to increase sharply and produce the acid amount, then the dicarboxylic acid that produces is separated from fermented liquid.In when beginning fermentation, normal alkane content is 10-20% (V/V) in the mixed solution, adds normal alkane between in due course later on, make in the fermented liquid normal alkane concentration all the time＞5% (V/V) be as the criterion.Alkali metal phosphate can be from KH
2PO
4, N
aH
2PO
4K
2HPO
4And N
A2HPO
4In select a kind of.Nitrate can select a kind of from potassium or sodium salt.
After the fermentation ends, add an amount of water, add alkali to PH10-12, be heated to 85-90 ℃, carry out the breakdown of emulsion layering, the upper strata is a Residual oil, reclaim usefulness again, clear liquid in the middle of emitting, lower floor's thalline layer is handled once or press filtration or centrifugal again, merge clear liquid, add proper amount of active carbon, at 85-90 ℃, decoloured 30 minutes, after removing gac, destainer is heated to 60-70 ℃, adds HCI or H
2SO
4Carry out acidizing crystal to PH4-5, be cooled to 30 ℃ after, air blow drying is used in press filtration, 60 ℃ of oven dry, white 13 carbon dicarboxylic acid crystallizates.
With P-12-242 bacterial strain of the present invention and fermentation process, can produce C
11-C
18Various single and mixed dicarboxylic acid.Wherein on 2.5 tons of jars, from n-tridecane fermentative production 13 carbon dicarboxylic acid, fermented 6 days, produce the acid amount up to 180-200g/L, the aftertreatment total recovery reaches 80%, and purity reaches more than 96%.
Example one (1), get a transfering loop P-12-242 bacterial classification, be coated on 15 * 180 Boiling tube wort solid inclined-planes
On, cultivated two days for 30 ℃.(2), get one of above-mentioned bacterial classification, insert in the 250ml triangular flask that 25ml alkane seed culture medium is housed in
On 220 rev/mins rotary shaker, cultivated 48 hours for 30 ℃.In the alkane seed culture medium
KH
2PO
48g/L, yeast extract paste 5g/L, corn steep liquor 3g/L, sucrose 5g/L, urea 3g/L is heavy
Wax 50ml/L, tap water preparation, PH5.0.(3), in the 500ml triangular flask of 15ml fermention medium is housed, insert the above-mentioned seed liquor of 3.5ml,
N was used in 200 rev/mins of rotary shaker top fermentations 4 days in per 24 hours
aOH transfers a PH to 7.5-
8.0。Fermention medium contains KH
2PO
48g/L, yeast extract paste 2g/L, corn steep liquor 1g/L, sodium-chlor
1.5g/L, urea 1g/L, n-tridecane 200ml/L, bubble enemy 500ppm, KNO
37g/L, from
Come the water preparation, PH7.5 sterilized 30 minutes down at 110 ℃.Transfer PH extremely with HCl after the fermentation ends
3, use the 100ml ether extraction, remove ether, get white crystals, use standard N
aThe titration of OH solution,
Calculate dicarboxylic acid content.DC as a result
12Output is 85.2g/L, through gas chromatographic analysis, and DC
12Purity
Be 97.46%.
Example 2
According to the method for example 1, be normal alkane nC
15, DC as a result
15Output be 53.6g/L, purity is 96.81%.
Example 3
According to the method for example 1, be normal alkane nC
17, DC as a result
17Output be 52.0g/L, purity is 97.2%.
Example 4
Seed culture medium and cultural method are with example 1, and fermention medium is KH
2PO
48g/L, N
aCl1g/L, yeast extract paste 2g/L, corn steep liquor 1g/L, KNO
37g/L, sucrose 15g/L, bubble enemy 600ppm, urea 1.8g/L, n-tridecane 200ml/L, the tap water preparation, PH7.5 fermented DC 4 days
13Output is 86.06g/L, DC
13Purity 93.3%.
Example 5
Seed culture medium and cultural method are with example one, and fermention medium is with example 4.Cultivating two days, 1500L fermention medium, wherein nC are equipped with in the 400LP-12-242 kind liquid access of not having assorted bacterium through microscopy
13300L in 40 minutes 2500L fermentor tanks of 121 ℃ of sterilizations, 29 ℃, 200 rev/mins, tank pressure 0.8Kg/cm
2, air flow 1: 0.8, before 28 hours, PH is controlled at below 6.8, and 28-60 hour, PH was controlled at below 7.3, every 8-6 hour, used N after 60 hours
aOH solution is transferred a PH to 7.5, since the 3rd day, adds n-tridecane 120L every day, and totally 3 times, fermentation (161 hours) more than 6 days, 13 carbon dicarboxylic acid content are 205g/L in the fermentation clear liquid.After the fermentation ends, add the 300L tap water, be heated to 80 ℃, add alkali and transfer PH to 11, cool, put into layering jar standing demix one day to 50 ℃, emit the upper strata Residual oil, reclaim and use, lower floor's bacterium layer is by press filtration, remove thalline, cleaner liquid and middle level clear liquid merge, and add 0.7% gac, 90 ℃ decoloured 15 minutes, gac is removed in press filtration, and the decolouring cleaner liquid is squeezed in the souring tank, adds water to DC
13Concentration is 4%, is heated to 70 ℃, adds dense HCl and is acidified to PH3, cool to about 30 ℃, and filter press, air blow drying, solid substance gets white DC 60 ℃ of oven dry
13249Kg, transformation efficiency 94.0%, purity is 96.7%.
Claims (2)
1. one kind is utilized the synchronous fermentation n-paraffins of microorganism to produce C
11-C
18The method of various long-chain alpha, omega-dibasic acids is characterized in that with n-tridecane (nC
13) be in the substratum of matrix, with candida tropicalis (Candida tropicalis) P-12-242, i.e. formed diprotic acid is reclaimed in CGMCC NO.0297 fermentation then.
2. candida tropicalis (Candida tropicalis) P-12-242 is a CGMCC NO.0297 bacterial strain.
Priority Applications (1)
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|---|---|---|---|
| CN97103876A CN1053470C (en) | 1997-04-04 | 1997-04-04 | Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN97103876A CN1053470C (en) | 1997-04-04 | 1997-04-04 | Method for producing undecane-1,11-bicarboxylic acid by microorgan fermenting synchronously |
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| CN1162644A true CN1162644A (en) | 1997-10-22 |
| CN1053470C CN1053470C (en) | 2000-06-14 |
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|---|---|---|---|
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067725C (en) * | 1998-12-16 | 2001-06-27 | 中国石油化工集团公司 | Process for producing alpha, omega-long chain binary acid by using microorganism fermentation |
| CN100360678C (en) * | 1999-09-30 | 2008-01-09 | 科金斯公司 | Improved fermentation process |
| CN102115767B (en) * | 2009-12-30 | 2013-04-17 | 张艾琳 | Method for synchronously fermenting n-undecane (nC11) to highly yield eleven-carbon dicarboxylic acid (DC11) by utilizing microorganism |
| CN107312804A (en) * | 2017-07-21 | 2017-11-03 | 张艾琳 | A kind of biofermentation new method of positive long-chain tridecanyldicarboxylic acid |
| CN113461514A (en) * | 2020-03-31 | 2021-10-01 | 上海凯赛生物技术股份有限公司 | Method for extracting long-chain dicarboxylic acid from fermentation liquor |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5626191A (en) * | 1979-08-09 | 1981-03-13 | Nippon Mining Co Ltd | Preparation of long-chain dicarboxylic acid |
| JPS608796B2 (en) * | 1982-03-26 | 1985-03-05 | 株式会社バイオリサ−チセンタ− | Method for producing long chain dicarboxylic acids from fats and oils |
| CN1071951A (en) * | 1991-10-29 | 1993-05-12 | 中国石油化工总公司抚顺石油化工研究院 | The method of asynchronous microbiological fermentative production long-chain alpha, omega-dibasic acid |
| CN1048754C (en) * | 1995-11-09 | 2000-01-26 | 中国科学院微生物研究所 | Process for producing long-chain alpha, omega-dicarboxylic acid by synchronous fermentation of microbe |
-
1997
- 1997-04-04 CN CN97103876A patent/CN1053470C/en not_active Expired - Lifetime
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1067725C (en) * | 1998-12-16 | 2001-06-27 | 中国石油化工集团公司 | Process for producing alpha, omega-long chain binary acid by using microorganism fermentation |
| CN100360678C (en) * | 1999-09-30 | 2008-01-09 | 科金斯公司 | Improved fermentation process |
| US7320884B2 (en) | 1999-09-30 | 2008-01-22 | Cognis Corporation | Fermentation process |
| CN102115767B (en) * | 2009-12-30 | 2013-04-17 | 张艾琳 | Method for synchronously fermenting n-undecane (nC11) to highly yield eleven-carbon dicarboxylic acid (DC11) by utilizing microorganism |
| CN107312804A (en) * | 2017-07-21 | 2017-11-03 | 张艾琳 | A kind of biofermentation new method of positive long-chain tridecanyldicarboxylic acid |
| CN113461514A (en) * | 2020-03-31 | 2021-10-01 | 上海凯赛生物技术股份有限公司 | Method for extracting long-chain dicarboxylic acid from fermentation liquor |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1053470C (en) | 2000-06-14 |
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