CN102443608A - Method for producing 1,3-propylene glycol by using microbial fermentation - Google Patents
Method for producing 1,3-propylene glycol by using microbial fermentation Download PDFInfo
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Abstract
The invention discloses a method for producing 1,3-propylene glycol by using microbial fermentation. The method for producing 1,3-propylene glycol by using microbial fermentation comprises seed cultivation process and fermentation cultivation process. The fermentation medium used in the fermentation cultivation process contains three-carbon or four-carbon carboxylic acid organics which contains alpha-carbonyl or alpha-amino and has a concentration of 0.3 g/L to 0.8 g/L, excluding pyruvic acid. The three-carbon or four-carbon carboxylic acid organics which contains the alpha-carbonyl or the alpha-amino excluding the pyruvic acid comprises alanine, alpha-aminobutyric acid and 2-butanone acid. By adding the three-carbon or four-carbon carboxylic acid organics in a special structure containing the alpha-carbonyl or the alpha-amino and excluding the pyruvic acid in the fermentation medium, the method of the invention can suppress activity of pyruvate kinase in a glycerin metabolic process, reduce generation of pyruvate intermediates in the metabolic pathway. Furthermore, contents of by-products, such as ethanol, generated by the pyruvic acid metabolism are reduced, transformation rate efficiency of glycerin primer is improved, and 1,3-propylene glycol production strength is enhanced.
Description
Technical field
The invention belongs to technical field of bioengineering, be specifically related to a kind of microbial fermentation that utilizes and produce 1, the method for ammediol.
Background technology
1, ammediol is a kind of important chemical material and medicine intermediate, in the manufacturing of trevira production and polyurethane and ring compound, has widely to use.By 1, ammediol synthetic polyester has biodegradable unique character and the excellent performance of waiting.In recent years, 1, ammediol is as important organic synthesis raw material and midbody, because of its special performance and widely purposes become the focus of research and development.
1, the working method of ammediol mainly contains three kinds: acrolein hydration hydride process, oxyethane carbonylation method and microbe transformation method.Though the microbe transformation method starting early, just causes people's attention gradually up to the 1980s.Although present main method remains chemical method; But compare with chemical method; Microbe transformation method has mild condition, easy and simple to handle, characteristics such as selectivity good, save the energy, facility investment is few and environment is good; Be the method that a kind of production cost is minimum, pollution is minimum, meet the requirement of current " green chemical industry " and " sustainable development ".
Produce 1 through microbial fermentation; The production technique of ammediol is ripe relatively; Mainly be divided into two types: produce 1 for the prepared using genetic engineering bacterium transforms with glucose; It is that prepared using klebsiella spp (Klebsiella pneumoniae), Fu Shi lemon bacillus (Citrobacter freundii), enterobacter agglomerans (Enterobacter agglomerans), clostridium butyricum (Clostridium butyricum) and Pasteur clostridium spp bacteriums such as (Clostridium pasteuianu) transform production 1, ammediol that ammediol reaches with glycerine.Because the production model of microbial transformation is to utilize mikrobe self metabolic process to carry out the production of useful prods; Therefore the fermentation byproduct kind is more in actual procedure; Especially be present in product such as lactic acid on the main metabolism main line, acetate, ethanol etc.; The appearance of these by products not only can exert an influence to fermentation system, so that influences fermentation production efficiency, and can impact the later stage product separation.Therefore, reduce the generation of by product in the fermentation system, help to improve 1, the productive rate of ammediol.
CN200510011867.8 discloses a kind of utilization and has produced biological diesel oil byproduct glycerin production 1; The method of ammediol; This method with isolated by product raw glycerine in the production of biodiesel process as fermentative Production 1; The substrate of ammediol carries out 1 through anaerobism or aerobic fermentation, the ammediol fermentative prodn with Cray Bai Shi bacillus or clostridium butylicum, clostridium pasteurianum.But in this method 1, the productive rate of ammediol and production intensity are not high and by product is many.CN03119280.7 discloses the integrated fermentative prodn 1 of two sections Double bottom things of a kind of employing; The method of ammediol; To cultivate be to serve as to mix the Double bottom thing with glucose and glycerine to secondary seed in this method, with the secondary seed under the oxygen consumption condition cultivate and anaerobic condition under the conversion of glycerine anaerobism be integrated in the same fermentor tank and carry out.Though this method can reduce process step, improve usage ratio of equipment, shortened process cycle owing to have thalli growth and two stages of transformation of glycerol in this process, a large amount of by product of easy generation, influence final 1, the productive rate of ammediol.CN200510011917.2 discloses a kind of external source of utilizing and has added FUMARIC ACID TECH GRADE promotion mikrobe synthetic 1; The method of ammediol; This method is added FUMARIC ACID TECH GRADE as a kind of external source electron acceptor(EA) in fermention medium, thereby quickens the utilization of thalline to glycerine.Can find out through embodiment,, improve 1 though this method can improve the utilization ratio of thalline to glycerine, ammediol concentration and production intensity, by product is showed increased also.CN200510047540.6 discloses a kind of mikrobe and has utilized the glycerine anaerobically fermenting to produce 1; The method of ammediol; This method is through adding an amount of polyprotonic acid in fermention medium or in the exponential phase of thalli growth; This polyprotonic acid can be strengthened the metabolic process behind the generation pyruvic acid in the metabolic process, but this method can not effectively reduce the generation of by product, because the polyprotonic acid that adds can not be regulated and control the generation of pyruvic acid; And pyruvic acid is the source that generates multiple by product, and the pyruvic acid in the metabolism can decompose fully.CN03121946.2 discloses a kind of external source interpolation reductive agent that passes through and has promoted thalline to synthesize 1, the method for ammediol, and this method utilizes 1; Need to consume the characteristic of a certain amount of reducing equivalent in the ammediol biosynthetic process; Add an amount of reductive agent at fermention medium or in anaerobic fermentation process, strengthen the accumulation of reducing equivalent in the thalline, promote substrate glycerine along the metabolism of reduction approach; Improve 1, the synthetic concentration and the transformation efficiency of ammediol.Though in substratum, add reductive agent; Help glycerine to 1 in theory, ammediol transforms, but in whole pathways metabolism; The intervention of a large amount of reducing equivalents can promote a lot of side reactions, like pyruvic acid to the conversion of lactic acid, PEP conversion, acetyl C to succsinic acid
OA is to the alcoholic acid conversion etc., thus reductive agent add the generation that affiliation causes a large amount of by products.
Summary of the invention
To the deficiency of prior art, the present invention provides a kind of microbial fermentation that utilizes to produce 1, the method for ammediol; This method is through adding the additive with particular configuration in fermention medium; This additive can suppress the activity of pyruvate kinase in the glycerine metabolic process, reduces the generation of pyruvic acid midbody in the metabolic pathway, and then has reduced the content of by-products such as ethanol that generated by the pyruvic acid metabolism; Improve transformation efficiency efficient, the enhancing 1 of glycerine substrate, the ammediol production intensity.
The present invention utilizes microbial fermentation to produce 1; The method of ammediol; Comprise seed culture process and fermentation culture process; What contain concentration in the used fermention medium of fermentation culture process and be 0.3g/L～0.8g/L contains alpha-carbonyl or alpha-amino three carbon or four carbon carboxylic-acid organism, except the pyruvic acid.
In the inventive method, contain alpha-carbonyl or alpha-amino three carbon or four carbon carboxylic-acid organism except the described pyruvic acid comprise L-Ala, butyrine, 2-butanone acid.
The inventive method fermentation culture process is substrate with glycerine; Seed liquor volume and fermention medium volume ratio are 1: 10～1: 30; Culture temperature is 30 ℃～40 ℃, and stirring velocity is 200rpm～500rpm, and pH is controlled between 6～8; Nitrogen feeding amount is 2vvm～4vvm, keeps anaerobic condition in the fermenting process.
The used glycerine substrate of the inventive method fermentation culture process derives from the by-product glycerin that is generated in chemical method, biological process and the supercritical methanol technology production biofuel process, and this by-product glycerin only need carry out simple separating treatment and promptly can be used as the glycerine substrate in the fermentation culture.
Fermentation mode can be that batch fermentation, batch formula stream add fermentation or continuously ferments in the inventive method.During batch fermentation in the substratum glycerol concentration be 25g/L～45g/L, fermentation time is 12h～60h.
Culture presevation liquid and seed culture medium volume ratio are 1: 100～1: 500 in the inventive method seed culture process; Culture temperature is 30 ℃～40 ℃, and stirring velocity is 100rpm～200rpm, and pH is 6～8; Incubation time is 10h～20h, keeps anaerobic condition between during cultivation.
In the inventive method, described bacterial classification is klebsiella spp (Klebsiella pneumoniae), Fu Shi lemon bacillus anaerobism or facultative anaerobes such as (Citrobacter freundii).
Compared with prior art, fermentative prodn 1 of the present invention, the method for ammediol has following advantage:
1, the inventive method an amount of contains alpha-carbonyl or contains alpha-amino three carbon and four carbon carboxylic-acid organism (except the pyruvic acid through in fermention medium, adding; Below identical); Contain alpha-carbonyl or contain alpha-amino three carbon and four carbon carboxylic-acid organism (contain alpha-carbonyl or alpha-amino group and suitable molecular chain length) because its unique molecular configuration and can suppress the activity of pyruvate kinase in the glycerine metabolic process; Reduce the generation of pyruvic acid midbody in the metabolic pathway; And then reduced content of by-products such as the ethanol that generates by the pyruvic acid metabolism, acetate, improve the glycerine substrate transformation efficiency efficient, strengthen 1, the ammediol production intensity.Adopting the intermittent type fermentation mode, carry out in the fermentation test process of 1L level, under the identical fermentation condition, the glycerine fermenting substrate generates 1, and the molar yield of ammediol can reach 73.3%, obviously is superior to 63.8% in the comparative example.
Can know from prior art that 2, in the metabolic pathway of glycerine, glycerine can under anaerobic carry out metabolism through two parallel paths of oxidation and reduction.In oxidative pathway, glycerine is generated otan by the glycerol dehydrogenase dehydrogenation, and further metabolism becomes pyruvic acid then; In the reduction approach, glycerine is then generated the 3-hydroxy propanal by the glycerol dehydratase catalytic dehydration, further at NADH
2Participation under, by 1, ammediol redox enzyme catalysis generates 1, ammediol.The pyruvic acid that the glycerine oxidative pathway produces is at NADH
2Effect through different reduction reactions, can generate by products such as acetate, ethanol, lactic acid down.Because various production of by-products originate in an initial thing of common---pyruvic acid, be the reaction of pyruvic acid therefore through suppressing by transformation of glycerol, not only can reduce NADH in the by product generative process
2Consumption, to increase NADH in the glycerine reduction approach
2Supply, strengthen 1, the production intensity of ammediol, and can reduce the generation of by product improves glycerine and generates 1, the molar yield of ammediol.
3, be that the reaction of pyruvic acid has plurality of enzymes to participate in by transformation of glycerol, like glycerol dehydrogenase, dihydroxyacetone kinase, pyruvate kinase etc., competitive inhibitor through adding enzyme or substrate analogue effectively inhibitory enzyme are lived the generation of minimizing side reaction thing.Because there is the allosteric retarding effect in pyruvate kinase; Therefore can in substratum, add the suitable four carbon carboxylic-acid organism that contain alpha-carbonyl or contain alpha-amino three carbon and four carbon carboxylic-acid organism; Thereby, reduce the effect that by product generates to play in the activity of this enzyme of substrate level inhibition.
Embodiment
Further specify effect of the present invention below in conjunction with embodiment, but be not construed as limiting the invention.All adopt the batch fermentation mode in following examples and the comparative example, used glycerine substrate is made a living and is produced the raw glycerine that produces in the thing diesel oil process in the fermenting process.
In the inventive method, constitute the liquid phase analysis system with Waters 2695 separation systems and Waters 2414 differential detectors, wherein separator column is selected Aminex HPX-87H organic acid and pure analytical column for use, is used for separating of acids and alcohols.With lactic acid, glycerine, acetate, 1, standard models such as ammediol, ethanol are set up standard diagram, regularly measure consumption situation, the product 1 of glycerine in the reaction system in the reaction process, ammediol and main by product alcoholic acid accumulation.
In the inventive method; Used bacterial classification is klebsiella spp (Klebsiella pneumoniae); From Sinopec Fushun Petrochemical Research Institute patent bacterial classification, bacterial classification is in Chinese common micro-organisms DSMZ (CGMCC) preservation, culture presevation number: 0798.
The essentially consist of seed culture medium and fermention medium is following in the inventive method:
Embodiment 1 utilizes the fermention medium that contains the 0.5g/L L-Ala to carry out 1, the ammediol fermentation test
(1) seed culture: klebsiella spp (Klebsiella pneumoniae) the culture presevation liquid 1mL that gets the liquid preservation adds in the 200mL seed culture medium, is mixed in and shakes in the bottle, carries out seed liquor and cultivates.Culture condition: culture temperature is 37 ℃, and shaking table concussion speed is made as 100rpm, and pH is controlled at 7.0, keeps anaerobic condition in the culturing process, cultivates 15h altogether.
(2) fermenting process: the fermentor tank volume is selected 1L, uses batch fermentation, once adds the glycerine pattern.Getting 40mL seed liquor adding 460mL contains in the fermention medium of 0.5g/L L-Ala.The collocation method of this fermention medium is on the basis of minimum medium, adds L-Ala and substrate glycerine, makes it contain 0.5g/L L-Ala, 40g/L glycerine.Fermentating controling condition: temperature is 37 ℃, and stirring velocity is 400rpm, regulates pH with 5MNaOH in the process, makes it be controlled to be 7, feeds nitrogen in the fermenting process to keep anaerobic environment, and nitrogen feeding amount is 2vvm, and the full fermenting process time is 16h.
(3), measure consumption situation, the product 1 of glycerine in the reaction system, the accumulation of ammediol and by product ethanol etc. through the liquid phase analysis system.Through liquid phase analysis, in product 1, the concentration of ammediol is 22.047g/L, and alcohol concn is 1.190g/L, and the glycerine residual concentration is 3.575g/L.Through calculating, 1, the mole yield of ammediol is 73.3%, by product alcoholic acid mole yield is 6.53%.
Embodiment 2 utilizes the fermention medium that contains the 0.3g/L butyrine to carry out 1, the ammediol fermentation test
(1) seed culture: klebsiella spp (Klebsiella pneumoniae) the culture presevation liquid 1mL that gets the liquid preservation adds in the 300mL seed culture medium, is mixed in and shakes in the bottle, carries out seed liquor and cultivates.Culture condition: culture temperature is 37 ℃, and shaking table concussion speed is made as 100rpm, and pH is controlled at 7.0, keeps anaerobic condition in the culturing process, cultivates 16h altogether.
(2) fermenting process: the fermentor tank volume is selected 1L, uses batch fermentation, once adds the glycerine pattern.Getting 20mL seed liquor adding 480mL contains in the fermention medium of 0.3g/L butyrine.The collocation method of this fermention medium is on the basis of minimum medium, adds butyrine and substrate glycerine, makes it contain 0.3g/L butyrine, 40g/L glycerine.Fermentating controling condition: temperature is 37 ℃, and stirring velocity is 400rpm, regulates pH with 5MNaOH in the process, makes it be controlled to be 7, feeds nitrogen in the fermenting process to keep anaerobic environment, and nitrogen feeding amount is 2vvm, and the full fermenting process time is 16h.
(3), measure consumption situation, the product 1 of glycerine in the reaction system, the accumulation of ammediol and by product ethanol etc. through the liquid phase analysis system.Through liquid phase analysis, in product 1, the concentration of ammediol is 21.878g/L, and alcohol concn is 1.293g/L, and the glycerine residual concentration is 4.122g/L.Through calculating, 1, the mole yield of ammediol is 73.8%, by product alcoholic acid mole yield is 7.20%.
Embodiment 3 utilizes the fermention medium that contains the 0.8g/L2-batanone acid to carry out 1, the ammediol fermentation test
(1) seed culture: klebsiella spp (Klebsiella pneumoniae) the culture presevation liquid 1mL that gets the liquid preservation adds in the 200mL seed culture medium, is mixed in and shakes in the bottle, carries out seed liquor and cultivates.Culture condition: culture temperature is 36 ℃, and shaking table concussion speed is made as 200rpm, and pH is controlled at 7.0, keeps anaerobic condition in the culturing process, cultivates 16h altogether.
(2) fermenting process: the fermentor tank volume is selected 1L, uses batch fermentation, once adds the glycerine pattern.Getting 30mL seed liquor adding 470mL contains in the fermention medium of 0.8g/L L-Ala.The collocation method of this fermention medium is on the basis of minimum medium, adds 2-butanone acid and substrate glycerine, makes it contain 0.8g/L2-batanone acid, 40g/L glycerine.Fermentating controling condition: temperature is 37 ℃, and stirring velocity is 400rpm, regulates pH with 5MNaOH in the process, makes it be controlled to be 7, feeds nitrogen in the fermenting process to keep anaerobic environment, and nitrogen feeding amount is 2vvm, and the full fermenting process time is 16h.
(3), measure consumption situation, the product 1 of glycerine in the reaction system, ammediol and main by product alcoholic acid accumulation through the liquid phase analysis system.Through liquid phase analysis, in product 1, the concentration of ammediol is 20.209g/L, and alcohol concn is 0.755g/L, and the glycerine residual concentration is 5.809g/L.Through calculating, glycerine produces 1, and the mole yield of ammediol is 71.5%, and by product alcoholic acid mole yield is 5.73%.
Comparative example
According to the scheme of CN200510047540.6, contain the succsinic acid of concentration in the minimum medium that fermentation is used as 0.5g/L, all the other conditions are with embodiment 1.Through liquid phase analysis, in product 1, the concentration of ammediol is 18.922g/L, and alcohol concn is 1.418g/L, and the glycerine residual concentration is 4.141g/L.Through calculating, 1, the mole yield of ammediol is 63.8%, by product alcoholic acid mole yield is 7.90%.
Can know by comparative example and embodiment 1; Add the Succinic Acid and the L-Ala of equal in quality in the fermention medium, the adding of L-Ala can obviously improve 1, ammediol mole yield; Reduce main by product alcoholic acid mole yield; 1, ammediol mole yield has improved 14.9%, and main by product alcoholic acid mole yield has reduced by 17.1%.
Claims (8)
1. one kind is utilized microbial fermentation to produce 1; The method of ammediol; Comprise seed culture process and fermentation culture process; What it is characterized in that containing in the used fermention medium of fermentation culture process concentration and be 0.3g/L～0.8g/L contains alpha-carbonyl or alpha-amino three carbon or four carbon carboxylic-acid organism, except the pyruvic acid.
2. method according to claim 1 is characterized in that the contain alpha-carbonyl or alpha-amino three carbon or four carbon carboxylic-acid organism except the pyruvic acid comprises L-Ala, butyrine, 2-butanone acid.
3. method according to claim 1; It is characterized in that the fermentation culture process is substrate with glycerine, seed liquor volume and fermention medium volume ratio are 1: 10～1: 30, and culture temperature is 30 ℃～40 ℃; Stirring velocity is 200rpm～500rpm; PH is controlled between 6～8, and nitrogen feeding amount is 2vvm～4vvm, keeps anaerobic condition in the fermenting process.
4. method according to claim 3 is characterized in that the glycerine substrate derives from the by-product glycerin that is generated in chemical method, biological process and the supercritical methanol technology production biofuel process.
5. according to claim 1 or 3 described methods, it is characterized in that fermentation mode can be that batch fermentation, batch formula stream add fermentation or continuously ferments.
6. method according to claim 4, when it is characterized in that batch fermentation in the substratum glycerol concentration be 25g/L～45g/L, fermentation time is 12h～60h.
7. method according to claim 1; It is characterized in that culture presevation liquid and seed culture medium volume ratio are 1: 100～1: 500 in the seed culture process; Culture temperature is 30 ℃～40 ℃, and stirring velocity is 100rpm～200rpm, and pH is 6～8; Incubation time is 10h～20h, keeps anaerobic condition between during cultivation.
8. according to claim 1 or 6 described methods, it is characterized in that described bacterial classification is klebsiella spp, Fu Shi lemon bacillus.
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| CN115521218A (en) * | 2022-07-26 | 2022-12-27 | 盐城工学院 | Preparation method of amino acid surfactant raw material |
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| CN1955304A (en) * | 2005-10-26 | 2007-05-02 | 中国石油化工股份有限公司 | Method for producing 1,3-propylene of using glycerol anaerobic fermentation |
| CN101307335A (en) * | 2007-05-18 | 2008-11-19 | 中国石油化工股份有限公司 | Process for producing 1,3-propylene glycol by microbe fermentation |
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| CN1955304A (en) * | 2005-10-26 | 2007-05-02 | 中国石油化工股份有限公司 | Method for producing 1,3-propylene of using glycerol anaerobic fermentation |
| CN101307335A (en) * | 2007-05-18 | 2008-11-19 | 中国石油化工股份有限公司 | Process for producing 1,3-propylene glycol by microbe fermentation |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115521218A (en) * | 2022-07-26 | 2022-12-27 | 盐城工学院 | Preparation method of amino acid surfactant raw material |
| CN115521218B (en) * | 2022-07-26 | 2023-08-22 | 盐城工学院 | Preparation method of amino acid surfactant raw material |
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