CN100999742B - High yield technology of producing 1,3 propyl diol by fermenting - Google Patents
High yield technology of producing 1,3 propyl diol by fermenting Download PDFInfo
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Abstract
The present invention relates to a high yield process for 1, 3-propylene glycol producing fermentation and belongs to the field of biochemical technology. During the fermentation, oxygen dissolving amount and substrate glycerin adding rate are controlled based on the concentration of 3-hydroxy propionic aldehyde as an intermediate metabolite for the 1,3-propylene glycol production by the substrate glycerin in the fermenting liquor and the variation thereof. The concentration of the 3-hydroxy propionic aldehyde is controlled in 2-10 mmol/L, and may be increased by means of increasing the substrate adding rate or lowering the oxygen dissolving amount or decreased by means of decreasing the substrate adding rate or increasing the oxygen dissolving amount, so that the fermentation pause phenomenon caused by the accumulation of the intermediate metabolite of 3-hydroxy propionic aldehyde does not happen, meanwhile the product 1, 3-propylene glycol has high producing strength, the ultimate 1, 3-propylene glycol concentration in the fermenting liquor can reach to 60-80 g/L. The whole fermentation process has simple control, convenient operation and high universality.
Description
Technical field
The invention belongs to technical field of biochemical industry, particularly a kind of fermentative production 1, the high yield tech of ammediol promotes microorganism to synthesize 1 with 3-hydroxypropyl aldehyde concentration as the fermentation control index, ammediol, raising 1,3-propylene glycol fermentation concentration and yield.
Background technology
1, ammediol is mainly produced polyester material as monomer, generates Poly(Trimethylene Terephthalate) with terephthalic acid.Also can produce some other biodegradable polyesters material in addition, as 1, ammediol and 1, polymkeric substance (the Liu Y. that 4-cyclohexanedimethanol and succsinic acid polymerization obtain, Ranucci E., Lindblad M.S., AlbertssonA.2001.New Biodegradable Polymers from Renewable Sources:Polyester-carbonates Based on 1,3-Propylene-co-1,4-CyclohexanedimethylenneSuccinate.J.Polym.Sci.Part be A.39: 25082519).1, ammediol can be produced by traditional chemical synthesis process.It is method (the Arntz D. of raw material that industrial process has the propenal of Degussa company, Haas T., Muller A., Wiegand is untersuchung zurhydratisierung von acrolein.Chem.Ing.Tech.63 N.1991Kinetische: 733-735) oxyethane with Shell company is method (the Slaugh L.H. of raw material, PowellJ.B., Forschner T.C., Semple, T.C., Weider, P.R1995.Process for preparing 1,3-propanediol.United StatesPatent.5,463,146).People have developed gradually and have utilized Production by Microorganism Fermentation 1, the method for ammediol in recent years.Though Production by Microorganism Fermentation 1, ammediol still are in the laboratory study stage at present.But it is the strong challenge that feature " green industry " proposes to traditional petrochemical complex with the biotechnology, thereby has important practical significance.Compare with chemical synthesis, microbe fermentation method has mild condition, easy and simple to handle, advantage such as by product is few, environmental pollution is little.Along with Nonrenewable resources reduce and the increasing of world population day by day, green industry is more and more paid attention to by people, utilizes microbial technique to change renewable resource into useful chemical substance and demonstrates its important practical sense.
For 1, the report of ammediol fermentation control: (willow is refined for the refined grade of willow in 2006, the palace weighing apparatus, Fu Shuilin, two stages control glycerol concentration improves 1, the ammediol fermentation level, East China University of Science's journal, 2006-09:1042-1045) find that the different glycerol concentration of different steps control has different influences to thalli growth and product generation, in addition, Barbirato (Barbirato F., SoucailleP., Bories is Involved in Accumulation of 3-Hydroxypropionaldehyde duringFermentation of Glycerol by Enterobacter agglomerans.Appl.Environ.Mi crobiol.62 A.1996PhysiologicMechanisms: 4405-4409) studying the growth of anaerobism enterobacteria and producing 1, find during ammediol, if the high density accumulation takes place in mesostate 3-hydroxy propanal, fermentation is ended, because the 3-hydroxy propanal is a kind of material to the toxic effect of thalline.Studying well aerobe fermentation method production 1, during ammediol, also there is fermentation termination phenomenon (the woods dayglow that the 3-hydroxy propanal causes equally in discovery, Liu Hongjuan etc., 3-hydroxypropyl aldehyde the 1.3-propylene glycol is produced in fermentation to Klebsillapneumoniae influence and regulation and control thereof, modern chemical industry, 2005-09: 47-51), reduce the accumulation of 3-hydroxy propanal in the fermented liquid in the literary composition by the pH value that adopts lower initial glycerol concentration of fermentation and control fermentation, but 3-hydroxypropyl aldehyde concentration is promoted microorganism synthetic 1 as the fermentation control index, ammediol, the method that improves 1,3-propylene glycol fermentation concentration and yield yet there are no report.
Summary of the invention
At first, the purpose of this invention is to provide and a kind ofly promote microorganism synthetic 1 as the fermentation control index with 3-hydroxypropyl aldehyde concentration, ammediol, raising 1, the method of 3-propylene glycol fermentation concentration and yield, it comprises according to 3-hydroxypropyl aldehyde concentration carries out the adjusting of dissolved oxygen amount in the fermenting process and the regulation and control of concentration of substrate.
It is characterized in that: thalline is in the glycerol fermentation process, no matter be anaerobism or aerobic, it utilizes the glycerine metabolism to produce 1, three kinds of key enzymes of ammediol all can be expressed, but the dissolved oxygen difference, enzyme is lived different, dissolved oxygen amount is low excessively, the metabolic enzyme imbalance of glycerine causes the mesostate 3-hydroxy propanal accumulation of toxic, thereby makes fermenting process end; Dissolved oxygen amount is too high, and then biomass and other by product metabolism increase, and the PDO yield descends.Equally, glycerine is to produce 1, the main substrate composition of ammediol, if the concentration of glycerine is low excessively in the fermenting process, then fermentative production intensity is just very low; If the excessive concentration of glycerine in the fermenting process can cause the accumulation of the mesostate 3-hydroxy propanal of toxic again, thereby make fermenting process end.So the dissolved oxygen amount of fermenting process and concentration of substrate only are controlled in the suitable scope, could both keep higher production intensity, can not cause the abort of fermentation again.
Ferment method of the present invention produces 1, and the ammediol bottoms stream adds the technology process and is:
Seed liquor is added in the fermention medium, and the glycerol concentration of fermention medium is 5-50g/l, and glucose concn is 0～5g/L, and the pH value is 5.5-8.5,30～40 ℃ of leavening temperatures.According to the actual conditions of fermentor tank, feed the air of 0-1.0vvm, mixing speed is 20～500rpm.To in time detect the concentration of 3-hydroxy propanal in the fermented liquid after the fermentation beginning, at first judge that by the change in concentration of 3-hydroxy propanal the dissolved oxygen amount of fermentation is whether suitable and adjusted, and then adjust the stream rate of acceleration of substrate, thereby adjust the concentration of substrate glycerine according to the concentration of 3-hydroxy propanal.Fermentation beginning back according to dissolved oxygen amount can occur moderate, too high, cross low three kinds of situations, be described below respectively:
1. along with the carrying out of fermenting, thalli growth, the concentration of 3-hydroxy propanal also rises gradually, along with substrate glycerine constantly is consumed, descending appears in the concentration of 3-hydroxy propanal in the fermented liquid, shows that the fermentation parameter of setting is reasonable, and the dissolved oxygen amount of fermentation is suitable, begin to flow the mixture of glycerol adding or glycerine and glucose etc. this moment when glycerol concentration is in 3-10g/L.Stream adds the concentration of 3-hydroxy propanal in the follow-up continuous monitoring fermented liquid of beginning, and adjusts the stream rate of acceleration of substrate at any time according to the concentration of 3-hydroxy propanal, when the excessive concentration of 3-hydroxy propanal in the fermented liquid, reduces the bottoms stream rate of acceleration even stops stream and add; Cross when low when the concentration of 3-hydroxy propanal in the fermented liquid, increase the stream rate of acceleration of substrate.The concentration that keeps 3-hydroxy propanal in the fermented liquid is between 2～10mmol/L.To fermentation ends.
2. along with the carrying out of fermentation, the change in concentration of 3-hydroxy propanal is little, and is lower than 2mmol/L; Continue fermentation, when glycerol concentration is in 3-10g/L, begin to flow the mixture of glycerol adding or glycerine and glucose etc.And increase the stream rate of acceleration of substrate gradually, the concentration that promptly increases substrate glycerine in the fermented liquid improves the concentration of 3-hydroxy propanal, this moment is when if the concentration of 3-hydroxy propanal still is lower than 2mmol/L in the fermented liquid, show that then dissolved oxygen is excessive, should reduce the air flow of fermentation and dissolved oxygen that rotating speed reduces fermentation as early as possible (according to the concentration of 3-hydroxy propanal and the practical situation of fermentor tank, air flow and rotating speed are transferred 10%-30% up and down on former basis), after the dissolved oxygen adjustment is suitable, again according to the concentration of 3-hydroxy propanal in the fermented liquid, according to the stream rate of acceleration of 2 described principles adjusting substrate glycerine, to fermentation ends.
3. along with the carrying out of fermenting, the concentration of 3-hydroxy propanal can constantly rise, after concentration surpasses 10mmol/L, the consumption of substrate glycerine is also slow, thalli growth is stagnated even is dead, before thalline death, in time increases dissolved oxygen amount and saves, same stream rate of acceleration of regulating the substrate glycerine according to 2 described principles is to fermentation ends.
Microorganism of the present invention is gram
Thunder Bai Shi pneumobacillusKlebsiella pneumoniae;
Cray Bai Shi produces acid BacillusKlebsiella oxytoca; Clostridium butylicum Clostridium butyricu; Any among the clostridium pasteurianum ClostridiumPasteurianum.
Fermentation mode of the present invention comprises: batch stream adds fermentation and continuously ferments, and is applicable to the container of all liquid state fermentations carried out that comprise mechanical agitator tank, gas lift fermentor tank.
Beneficial effect of the present invention is: the 3-hydroxy propanal concentration with fermented liquid is foundation during the fermentation, the stream rate of acceleration of regulation and control dissolved oxygen amount and substrate.Fermentation can be carried out smoothly, phenomenon owing to mesostate 3-hydroxy propanal accumulation causing fermentation termination can not take place, and can improve 1, the ammediol production intensity simultaneously, in the final fermented liquid 1, ammediol concentration can arrive 60～80g/L.Whole fermentation process control is simple, easy to operate, highly versatile.
Embodiment
The invention provides a kind of in fermentative Production 1, in the ammediol process, with 3-hydroxypropyl aldehyde concentration as the fermentation control index, to the dissolved oxygen amount and the method regulated and control of bottoms stream rate of acceleration of fermentation.By the content of 3-hydroxy propanal in the monitoring fermented liquid, and according to its concentration and changing conditions, the timely dissolved oxygen amount of adjusting fermentation, and determine when substrate begins the speed that stream adds and stream adds, thus reach high production intensity and safe production.Fermentative Production 1, the CONTROL PROCESS process that ammediol dissolved oxygen amount and bottoms stream add is:
Seed liquor is added in the fermention medium, and the glycerol concentration of fermention medium is 5-50g/l, and glucose concn is 0～5g/L, and the pH value is 5.5-8.5,30～40 ℃ of leavening temperatures.According to the actual conditions of fermentor tank, feed the air of 0-1.0vvm, mixing speed is 20～500rpm.To in time detect the concentration of 3-hydroxy propanal in the fermented liquid after the fermentation beginning, at first to judge that the dissolved oxygen amount of fermentation is whether suitable and adjusted by the change in concentration of 3-hydroxy propanal, and then adjust the stream rate of acceleration of substrate, thereby adjust the concentration of substrate glycerine according to the concentration of 3-hydroxy propanal.Fermentation beginning back according to dissolved oxygen amount can occur moderate, too high, cross low three kinds of situations, be described below respectively:
1. along with the carrying out of fermenting, thalli growth, the concentration of 3-hydroxy propanal also rises gradually, along with substrate glycerine constantly is consumed, descending appears in the concentration of 3-hydroxy propanal in the fermented liquid, shows that the fermentation parameter of setting is reasonable, and the dissolved oxygen amount of fermentation is suitable, begin to flow the mixture of glycerol adding or glycerine and glucose etc. this moment when glycerol concentration is in 3-10g/L.Stream adds the concentration of 3-hydroxy propanal in the follow-up continuous monitoring fermented liquid of beginning, and adjusts the stream rate of acceleration of substrate at any time according to the concentration of 3-hydroxy propanal, when the excessive concentration of 3-hydroxy propanal in the fermented liquid, reduces the bottoms stream rate of acceleration even stops stream and add; Cross when low when the concentration of 3-hydroxy propanal in the fermented liquid, increase the stream rate of acceleration of substrate.The concentration that keeps 3-hydroxy propanal in the fermented liquid is between 2～10mmol/L.To fermentation ends.
2. along with the carrying out of fermentation, the change in concentration of 3-hydroxy propanal is little, and is lower than 2mmol/L; Continue fermentation, when glycerol concentration is in 3-10g/L, begin to flow the mixture of glycerol adding or glycerine and glucose etc.And increase the stream rate of acceleration of substrate gradually, the concentration that promptly increases substrate glycerine in the fermented liquid improves the concentration of 3-hydroxy propanal, this moment is when if the concentration of 3-hydroxy propanal still is lower than 2mmol/L in the fermented liquid, show that then dissolved oxygen is excessive, should reduce the air flow of fermentation and dissolved oxygen that rotating speed reduces fermentation as early as possible (according to the concentration of 3-hydroxy propanal and the practical situation of fermentor tank, air flow and rotating speed are transferred 10%-30% up and down on former basis), after the dissolved oxygen adjustment is suitable, again according to the concentration of 3-hydroxy propanal in the fermented liquid, according to the stream rate of acceleration of 2 described principles adjusting substrate glycerine, to fermentation ends.
3. dissolved oxygen amount is low excessively: along with the carrying out of fermentation, the concentration of 3-hydroxy propanal can constantly rise, after concentration surpasses 10mmol/L, the consumption of substrate glycerine is slow, thalli growth is stagnated even is dead, before thalline death, in time increases the increase dissolved oxygen amount and saves, same stream rate of acceleration of regulating the substrate glycerine according to 2 described principles is to fermentation ends.
Example 1
(1) bacterial classification: Cray Bai Shi pneumobacillus (Klebsiella pneumoniae)
(2) fermentation mode: the 5L mechanical agitating fermentation tank, batch stream adds fermentation
(3) fermenting process: 5L fermentor tank, liquid amount 3.5L, leavening temperature are controlled at 37 ℃, and the pH value is controlled at 6.8 by stream hydro-oxidation sodium or potassium hydroxide.It is 30g/L that fermention medium initially contains glycerol concentration, and glucose concn is for being 5g/L, bubbling air, air flow 0.5vvm, fermentor tank mixing speed 300rpm.And began to monitor the concentration of 3-hydroxy propanal and glycerine in 4 hours in fermentation, the concentration of 3-hydroxy propanal has risen to 4.05mmol/L in the time of 9 hours, dropped to 2.26mmol/L in 10 hours, beginning to carry out glycerine stream then adds, continue the concentration of monitoring 3-hydroxy propanal and glycerine, and instruct the flow acceleration of substrate glycerine with the concentration of 3-hydroxy propanal, and the concentration of 3-hydroxy propanal is controlled between 2～10mmol/L, 72 hours finish to fermenting.
(4) fermentation result: fermentation 36h, 1,3-propylene glycol concentration 73.61g/L, 1, ammediol is to the yield 50.34%, 2 of glycerine, and 3-butyleneglycol concentration 22.56g/L fermented 48 hours, 1, ammediol concentration is by 74.79g/L, and 1, ammediol is to the yield 46.61% of glycerine, 2,3-butyleneglycol concentration 22.63g/L fermented 72 hours, 1,3-propylene glycol concentration 80.50g/L, 1, ammediol is to the yield 47.44%, 2 of glycerine, 3-butyleneglycol concentration 20.38g/L.
Example 2
(1) bacterial classification: Cray Bai Shi pneumobacillus (Klebsiella pneumoniiae)
(2) fermentation mode: 50m
3Mechanical agitating fermentation tank, batch stream adds fermentation, and carries out in other condition homogeneous phase whiles, constant low glycerine stream rate of acceleration and the fermentation contrast experiment who flows rate of acceleration according to 3-hydroxy propanal concentration adjustment glycerine.
(3) fermenting process: 50m
3Fermentor tank, liquid amount 35m
3, leavening temperature is controlled at 37 ℃, and the pH value is controlled at 6.8 by stream hydro-oxidation sodium or potassium hydroxide.It is 25g/L that fermention medium initially contains glycerol concentration, and glucose concn is for being 5g/L, bubbling air, air flow 0.1vvm, fermentor tank mixing speed 60rpm.And began to monitor the concentration of 3-hydroxy propanal and glycerine in 4 hours in fermentation, the concentration of 3-hydroxy propanal rises to 4.65mmol/L after 8 hours, and the density loss of 9 hours 3-hydroxy propanals is 0.98mmol/L, beginning to carry out glycerine stream in 9 hours adds, continue the concentration of monitoring 3-hydroxy propanal and glycerine, and instruct the flow acceleration of substrate glycerine with the change in concentration of 3-hydroxy propanal, and the concentration of 3-hydroxy propanal is controlled between 2～10mmol/L, 48 hours finish to fermenting.
(4) fermentation result: under similarity condition, only do not compare with the control canisters of regulating and control flow acceleration than the concentration of low glycerine with reference to the concentration of 3-hydroxy propanal, fermentation 36h, 1,3-propylene glycol concentration rises to 62.57g/L by 53.95g/L, improves 16.0%.Fermented 48 hours, 1,3-propylene glycol concentration rises to 65.69g/L by 56.16g/L, improves 16.97%, 1, and ammediol rises to 43.52% to the yield of glycerine by 41.33%, improves 5.30%.
Example 3
(1) bacterial classification: Cray Bai Shi pneumobacillus (Klebsiellapneumoniae)
(2) fermentation mode: 5m
3Mechanical agitating fermentation tank, batch stream adds fermentation, and carries out at other condition homogeneous phases simultaneously, constant ventilation and fermentation contrast experiment according to 3-hydroxy propanal concentration adjustment ventilation.
(3) fermenting process: 5m
3Fermentor tank, liquid amount 3.5m
3, leavening temperature is controlled at 37 ℃, and the pH value is controlled at 6.8 by stream hydro-oxidation sodium or potassium hydroxide.It is 25g/L that fermention medium initially contains glycerol concentration, and glucose concn is for being 5g/L, bubbling air, air flow 0.2vvm, fermentor tank mixing speed 130rpm.And began to monitor the concentration of 3-hydroxy propanal and glycerine in 4 hours in fermentation, recorded that glycerol content is 2.33g/L in the fermented liquid in 8 hours, beginning to carry out glycerine stream adds, ferment after 14 hours, the concentration of finding the 3-hydroxy propanal has fluctuateed about 0.08mmol/L since beginning fermentation always, so reduced rotating speed to 90rpm at 16 hours, air flow is 0.1vvm, continue fermentation, and the same stream rate of acceleration that instructs substrate glycerine with the concentration of 3-hydroxy propanal, the concentration of 3-hydroxy propanal is controlled between 2～10mmol/L, and 48 hours finish to fermenting.
(4) fermentation result: compare fermentation 36h, 1 with the control canisters of not regulating dissolved oxygen amount under the similarity condition, 3-propylene glycol concentration rises to 53.35g/L by 40.99g/L, improves 30.15%, 1, ammediol rises to 41.75% to the yield of glycerine by 39.32%, improves 6.18%.Fermented 48 hours, 1,3-propylene glycol concentration rises to 56.3g/L by 44.96g/L, improves 25.22%, 1, and ammediol rises to 41.11% to the yield of glycerine by 38.99%, improves 5.44%.
Claims (2)
1. fermentative production 1, the high yield tech of ammediol promotes microorganism synthetic 1 with 3-hydroxypropyl aldehyde concentration as regulation index, ammediol; It is characterized in that: technological process is:
Seed liquor is added in the fermention medium, and the glycerol concentration of fermention medium is 5-50g/l, and glucose concn is 0～5g/L, and the pH value is 5.5-8.5,30～40 ℃ of leavening temperatures; According to the actual conditions of fermentor tank, feed the air of 0-1.0vvm, mixing speed is 20～500rpm; To in time detect the concentration of 3-hydroxy propanal in the fermented liquid after the fermentation beginning, at first judge that by the change in concentration of 3-hydroxy propanal the dissolved oxygen amount of fermentation is whether suitable and adjusted, and then adjust the stream rate of acceleration of substrate, thereby adjust the concentration of substrate glycerine according to the concentration of 3-hydroxy propanal; Fermentation beginning back according to dissolved oxygen amount occur moderate, too high, cross low three kinds of situations and be:
(1) along with the carrying out of fermenting, thalli growth, the concentration of 3-hydroxy propanal also rises gradually, along with substrate glycerine constantly is consumed, descending appears in the concentration of 3-hydroxy propanal in the fermented liquid, shows that the fermentation parameter of setting is reasonable, and the dissolved oxygen amount of fermentation is suitable, begin to flow the mixture of glycerol adding or glycerine and glucose this moment when glycerol concentration is in 3-10g/L; Stream adds the concentration of 3-hydroxy propanal in the follow-up continuous monitoring fermented liquid of beginning, and adjusts the stream rate of acceleration of substrate at any time according to the concentration of 3-hydroxy propanal, when the excessive concentration of 3-hydroxy propanal in the fermented liquid, reduces the bottoms stream rate of acceleration even stops stream and add; Cross when low when the concentration of 3-hydroxy propanal in the fermented liquid, increase the stream rate of acceleration of substrate; The concentration that keeps 3-hydroxy propanal in the fermented liquid is between 2～10mmol/L; To fermentation ends;
(2). dissolved oxygen amount is too high: along with the carrying out of fermentation, the change in concentration of 3-hydroxy propanal is little, and is lower than 2mmol/L; When glycerol concentration is in 3-10g/L, begin to flow the mixture of glycerol adding or glycerine and glucose, and increase the stream rate of acceleration of substrate gradually, the concentration that increases substrate glycerine in the fermented liquid improves the concentration of 3-hydroxy propanal, this moment is when if the concentration of 3-hydroxy propanal still is lower than 2mmol/L in the fermented liquid, show that then dissolved oxygen is excessive, should reduce the air flow of fermentation and the dissolved oxygen that rotating speed reduces fermentation as early as possible, according to the concentration of 3-hydroxy propanal and the practical situation of fermentor tank, air flow and rotating speed are transferred 10%-30% up and down on former basis, after the dissolved oxygen adjustment is suitable, adjust the stream rate of acceleration of substrate glycerine again according to the concentration of 3-hydroxy propanal in the fermented liquid, the concentration of 3-hydroxy propanal is between 2～10mmol/L, to fermentation ends in the control fermented liquid;
(3) dissolved oxygen amount is low excessively: along with the carrying out of fermentation, the concentration of 3-hydroxy propanal can constantly rise, after concentration surpasses 10mmol/L, the consumption of substrate glycerine is slow, and thalli growth is stagnated even be dead, before thalline death, in time increasing the increase dissolved oxygen amount saves, adjust the stream rate of acceleration of substrate glycerine again according to the concentration of 3-hydroxy propanal in the fermented liquid, the concentration of 3-hydroxy propanal is between 2～10mmol/L, to fermentation ends in the control fermented liquid.
2. according to claim 1, it is characterized in that: described microorganism is Cray Bai Shi pneumobacillus (Klebsiella pneumoniae); Cray Bai Shi produces acidfast bacilli (Klebsiella oxytoca); Clostridium butylicum (Clostridium butyricu); Any in the clostridium pasteurianum (Clostridium Pasteurianum).
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| CN101153292B (en) * | 2007-09-19 | 2010-09-29 | 北京化工大学 | Method for producing 1, trimethylene glycol by feedback control of substrate concentration with intermediate metabolites |
| CN101307336B (en) * | 2008-05-04 | 2011-08-17 | 清华大学 | Method for fermentation co-production of PDO,BDO and PHP by constructing gene engineering strain |
| CN102154385B (en) * | 2011-02-23 | 2013-01-16 | 安徽立兴化工有限公司 | Method for preparing 1,3-propylene glycol by controlling pH value with polyethylene polyamine and fermenting |
| CN102757985B (en) * | 2011-07-13 | 2014-06-25 | 河南天冠企业集团有限公司 | Method for controlling air quantity during production of 1,3-propylene glycol |
| CN104762239B (en) * | 2015-04-24 | 2017-12-15 | 张家港美景荣化学工业有限公司 | Klebsiella pneumoniae, application thereof and method for producing 1, 3-propylene glycol |
| CN111039756B (en) * | 2018-10-15 | 2023-10-10 | 中国石油化工股份有限公司 | Method and system for preparing 1, 3-propanediol |
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