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WO2011076690A1 - Procédé de purification du 1,2-propanediol à partir d'un bouillon de fermentation - Google Patents

Procédé de purification du 1,2-propanediol à partir d'un bouillon de fermentation Download PDF

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Publication number
WO2011076690A1
WO2011076690A1 PCT/EP2010/070102 EP2010070102W WO2011076690A1 WO 2011076690 A1 WO2011076690 A1 WO 2011076690A1 EP 2010070102 W EP2010070102 W EP 2010070102W WO 2011076690 A1 WO2011076690 A1 WO 2011076690A1
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propanediol
fermentation broth
purifying
solvent
anyone
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Inventor
Pascal Rousseaux
Frédéric OLLIVIER
Claire Ethgen
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Metabolic Explorer SA
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Metabolic Explorer SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
    • C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
    • C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation

Definitions

  • the present invention relates to the purification of 1 ,2-propanediol (MPG) from a fermentation broth.
  • MPG 1,2-propanediol
  • 1 ,2-propanediol is currently produced by chemical processes using a propylene oxide hydration process that consumes large amounts of water.
  • Propylene oxide can be produced by either of two processes, one using epichlorhydrin, and the other hydroperoxide. Both routes use highly toxic substances.
  • the hydroperoxide route generates by-products such as tert-butanol and 1 -phenyl ethanol. For the production of propylene to be profitable, a use must be found for these by-products.
  • the chemical route generally produces racemic 1 ,2-propanediol, whereas each of the two stereoisomers (R) 1 ,2-propanediol and (S) 1 ,2-propanediol are of interest for certain applications (e.g. chiral starting materials for specialty chemicals and pharmaceutical products).
  • 1 ,2-propanediol may be produced by fermentation of microorganisms using sugars such as glucose or sucrose.
  • Another major challenge is the elimination of heavy impurities including organic molecules such as organic acids which are less volatile or have a higher boiling point than 1 ,2-propanediol. These impurities tend to precipitate or to stick to the distillation columns used for purification of 1 ,2-propanediol.
  • the state of the art addresses mostly the purification of 1 ,3-propanediol from fermentation broths.
  • 1 ,3-propanediol and 1 ,2-propanediol are not produced through the same metabolic pathway. Therefore the composition of the fermentation broth containing the product to be purified is not the same and in particular the impurity profile is different.
  • the removal of mineral salts most notably it has been proposed to eliminate salts upstream from the purification steps by various techniques such as the use of ion-exchange resins (WO 2004101479), electrodialysis (CN101143301) and precipitation-filtration (US 6,361,983).
  • CN1460671 also describes purification of 1,3- propanediol from a fermentation broth comprising precipitation/separation steps with a solvent.
  • these methods suffer from major drawbacks and they do not address the elimination of the heavy impurities after removal of the salts.
  • WO 2009/068110 describes a method for purifying an alcohol from a fermentation broth.
  • the addition of glycerol to the concentrated fermentation broth prevents crystallization of salts at the bottom of the distillation columns.
  • the addition of glycerol retains salts in the liquid phase until the end of the purification process.
  • a major drawback of this process is that the amount of glycerol required to dissolve salts may be very high, leading to high purification costs.
  • WO 2004/101479 is related to the purification of biologically-produced 1,3- propanediol.
  • the purification process comprises filtration, ion exchange purification and a distillation procedure comprising at least two distillation columns. Salts are removed at the start of the process using ion exchange resins.
  • a major problem is the fouling of the ion exchange resins, which is due to the heavy impurities of the filtrated fermentation broth. Ion exchange is an efficient technique but it leads to very high operation costs due to the need for regeneration of the resin, when the technique is applied to solutions having a high salt content. Fouling of the ion exchange resin due to the heavy impurities and quick saturation due to high salts content both lead to elevated operation costs because regeneration and/or replacement of the resin are frequently required.
  • Xiu et al. (2008) is related to downstream processing of biologically produced 1,3- propanediol and 2,3-butanediol.
  • biological production of 1,3-propnaediol and 1,2-propanediol leads to different impurities requiring different purification methods.
  • Gao et al. (2007) is related to separation of 1,3 -propanediol from glycerol-based fermentations by alcohol precipitation and dilution crystallization. This document does not describe purification of 1,2-propanediol and the purification methods do not combine alcohol precipitation and an evaporation step on a falling film evaporator, wiped film evaporator, a thin film evaporator or a short path evaporator.
  • US2004/0222753 describes a process for producing 1,3 -propanediol from an aqueous feed stream using a solvent extractant. Precipitation of impurities and purification of 1,2-propanediol are not described.
  • the present invention proposes a novel method for purifying 1,2-propanediol from a fermentation broth.
  • the methods of the present invention provide both efficient desalinisation of the fermentation broth prior to further purification and efficient elimination of organic impurities and in particular of heavy impurities such as organic acids.
  • the methods of the present invention prevent degradation of 1,2- propanediol during the purification steps.
  • the methods according to the present invention make it possible to efficiently eliminate salts and impurities during the purification of 1,2-propanediol from a fermentation broth using a simple, cheap and easily scalable process.
  • the present invention is related to a method for purifying 1,2-propanediol from a fermentation broth comprising the following steps:
  • step e evaporating solvent and water from the solution obtained in the previous step d), f) evaporating the 1,2-propanediol from the solution obtained in step e) on a falling film evaporator, a wiped film evaporator, a thin film evaporator or a short path evaporator,
  • the clarification of the fermentation broth in step a) is carried out by filtration.
  • filtration consists in successive microfiltration, ultrafiltration and/or nano filtration steps.
  • step b) removing water from the aqueous solution containing the 1 ,2- propanediol is performed by evaporation.
  • the solvent is ethanol.
  • the solvent is added to reach a proportion of solvent comprised between 30% and 60% per weight.
  • step d) the solids are removed by filtration.
  • steps c), d) and e) are repeated before performing step f).
  • steps c), d) and e) are repeated two times before performing step f).
  • the 1,2-propanediol is evaporated from the solution obtained in step e) in a whipped thin film evaporator with an internal condenser.
  • the methods of the present invention comprise further purification of the 1,2-propanediol recovered in step g).
  • Further purification of the 1,2-propanediol may comprise removing by distillation products and/or azeotropes which have a boiling point lower than that of 1,2-propanediol by distillation; and removing products and/or azeotropes having a boiling point higher than that of 1 ,2-propanediol by distillation.
  • purification of the 1,2-propanediol may also comprise removing water by evaporation.
  • Further purification of the 1,2-propanediol may comprises ion exchange and/or adsorption.
  • the invention thus relates to the purification of 1,2-propanediol from a fermentation broth.
  • 1,2-propanediol may, for example, be produced by the fermentation of various carbon sources e.g. glucose, sucrose or glycerol.
  • the fermentation broth obtained after fermentation contains typically water, 1,2-propanediol, residual carbon source, mineral and organic salts of the carboxylate type.
  • 1,2-propanediol produced by fermentation contains a high concentration of organic and mineral salts.
  • salt means any mineral or organic salt present in the fermentation broth
  • mineral salts include ions such as Na , K , CI " , S0 4 and P0 4 Mg , Ca , NH 4 .
  • Organic impurities and by-products may include citrates, glucose, sucrose, succinates, acetates, pyruvates glycerol, hydroxyacetone and methylglyoxal.
  • the present invention relates to a method for removing salts from a fermentation broth after fermentative production of 1,2-propanediol.
  • the methods of the present invention also relate to further purification of the 1,2-propanediol after removal of mineral and organic salts.
  • Another object of the present invention is the efficient purification of 1,2- propanediol from an aqueous solution containing mineral and/or organic salts.
  • Purification of an alcohol from a fermentation broth by techniques such as distillation and evaporation leads to the crystallization of the mineral and organic salts which can prevent the further purification of the alcohol.
  • Various attempts have been made to remove mineral and organic salts from the fermentation broth prior to further purification of the alcohol.
  • distillation methods crystallization of salts at the bottom of the distillation column is a common problem, other methods such as ion exchange lead to quick fouling of the ion exchange resin due to the high amount of mineral salts and organic salts present in the fermentation broth.
  • an object of the present invention is the separation of the 1,2-propanediol from sodium chlorides, calcium chlorides, potassium chlorides, ammonium, sulfates and phosphate salts.
  • Another object of the present invention is the separation of 1,2-propanediol from heavy impurities present in the fermentation broth including organic molecules such as organic acids which are less volatile or have a higher boiling point than 1,2-propanediol.
  • a first embodiment of the present invention is a method for purifying 1,2- propanediol from a fermentation broth comprising the following steps:
  • step e) evaporating the 1,2-propanediol from the solution obtained in step e) on a falling film evaporator, a wiped film evaporator, a thin film evaporator or a short path evaporator,
  • Fermentation may optionally be stopped by addition of a base to the fermentation broth.
  • a base is added, for example, in the form of soda, potash or ammonia with the purpose of stopping bacterial activity.
  • the pH achieved is between 7.5 and 14.
  • the first step of the 1,2-propanediol purification method consists in clarification of the fermentation broth to eliminate insoluble elements, most notably large molecules, biomass, proteins and all suspended particles.
  • insoluble elements most notably large molecules, biomass, proteins and all suspended particles.
  • all molecules having a size over 0.1 ⁇ are eliminated by filtration.
  • all molecules having a molecular weight over 200 Da are eliminated by clarification. Any convenient method may be used for clarification of the fermentation broth.
  • clarification of the fermentation broth is carried out by filtration.
  • “Filtration” refers to a membrane separation method.
  • filtration consists successively of micro filtration, ultrafiltration and nano filtration steps.
  • the clarification step consists of micro filtration and ultrafiltration. More preferably, the clarification step consists of micro filtration. Most preferably, micro filtration is a 0.1 ⁇ cutoff micro filtration. Filtration may be carried out on a filter press or a rotary filter.
  • clarification of the fermentation broth is carried out by centrifugation.
  • water is removed prior to further purification of the 1,2-propanediol. Any appropriate method may be applied to remove water from the aqueous solution, e.g; but not limited to evaporation, cristalization or reverse osmosis. Preferably, water is removed by evaporation. Evaporation may be carried out in a thermosyphon-type evaporator or in any suitable evaporator.
  • this first step consisting in the concentration of the clarified fermentation broth, between 10% and 95 % of the aqueous solution is evaporated; preferably at least 60%>, 70%> or at least 80%> of the aqueous solution is evaporated.
  • a concentrated aqueous solution enriched in 1,2- propanediol is recovered after this first evaporation step. Preferably, this concentrated solution comprises at least 15%, 20% or 25% of 1,2-propanediol.
  • the next steps provide for precipitation of salts contained in the aqueous solution by addition of an appropriate solvent, precipitation and removal of the salts and evaporation of solvent and water as an azeotropic composition. These steps may be repeated 2-3 times to remove most of the mineral and organic salts.
  • Precipitation of solids from the aqueous solution containing the 1,2-propanediol is obtained by adding a solvent to reach a proportion of solvent comprised between 0.1% and 99%) per weight, preferably comprised between 30%> and 60%> per weight
  • the amount of solvent added is sufficient to promote the precipitation of solids from the aqueous solution.
  • the solvent is selected from ethanol, methanol and acetone. In preferred embodiments, the solvent is ethanol.
  • the solids are removed by any appropriate method.
  • the solid-liquid mixture is filtered to separate the wet cake consisting of the precipitated solids and the solution containing the 1,2-propanediol.
  • solvent and water are removed from the solution containing the 1,2-propanediol.
  • solvent and water are removed by evaporation of an azeotropic composition.
  • solvent and water are preferably evaporated at atmospheric pressure and the evaporation rate is at least 50%, 60% or 65%.
  • steps including solvent addition, precipitation and removal of solvent/water may be performed several times in order to remove most of the salts. In preferred embodiments, these steps are performed three times. At this stage, mineral salts and organic salts are removed from the solution containing the 1,2-propanediol. The final evaporation of solvent and water is performed under conditions allowing removal of 100% of the solvent.
  • the aqueous solution containing the 1,2-propanediol is fed to a falling film evaporator, a wiped film evaporator, a thin film evaporator or a short path evaporator.
  • the aqueous solution containing the 1,2-propanediol is fed to a wiped thin film evaporator with an internal condenser.
  • vacuum i.e. low pressure evaporation is used.
  • a substantial decrease of the boiling temperature of the 1,2-propanediol is obtained by reducing the operating pressure.
  • the operating pressure is set typically between 0.1 and 200 mbar, preferably between 1 and 50 mbar and the temperature is set between 50 and 150 °C.
  • the conditions are set to evaporate most but not the total amount of 1,2- propanediol in order to avoid the evaporation of impurities at this step.
  • the evaporate to fed mass ratio is comprised between 5 and 95 %, most preferably, the evaporate to fed mass ratio is 70%>.
  • the evaporated product typically comprises mostly 1,2-propanediol and water.
  • the bottom product contains heavy impurities, for example sugar, biomass, proteins and some remaining salts.
  • the bottom product may also comprise some residual 1,2-propanediol, which has not been evaporated.
  • the residual 1,2-propanediol amounts are preferably less than 10% and preferably less than 5% of the 1,2-propanediol fed to the evaporator. This 1,2- propanediol may also be recovered later in the process.
  • a successful evaporation step will provide both a high yield of 1,2-propanediol in the evaporated product, and sufficient liquid bottom product to draw out the heavy impurities and remaining salts.
  • the evaporated product contains most of the 1,2- propanediol, it is preferred that some residual 1,2-propanediol is recovered in the bottom product to avoid contamination of the evaporated 1,2-propanediol with impurities.
  • the residual 1,2-propanediol in the bottom product of the evaporator may amount to at least 1%, 2%, 5% or 10% of the 1,2-propanediol of the aqueous solution fed to the evaporator.
  • 1,2-propanediol can be further purified according to any known alcohol-purification technique, in particular by distillation.
  • topping and stripping may be performed.
  • an ion exchange step and/or adsorption step may also be included in the distillation sequence, as a polishing step, to maximize final product quality.
  • Another optional step of the method of the present invention is adjusting the pH to a pH>7 during purification. By raising the pH, acids can be separated and eliminated as ions.
  • the method according to the present invention also comprises further removal of water leading to concentration of the evaporated product containing the 1,2-propanediol.
  • Water can be eliminated by various techniques known to persons skilled in the art.
  • water is removed by evaporation.
  • further purification of the 1,2-propanediol is performed by distillation techniques. Elimination by distillation of products with a boiling point lower than that of the 1,2-propanediol to be purified and products with a boiling point higher than that of the 1,2-propanediol to be purified is carried out according to conventional techniques known to persons skilled in the art.
  • an ion exchange step and/or adsorption may be performed in between the different distillation steps or after the final distillation step. These techniques are used as a final polishing step, in order to maximize product quality.
  • ion exchange is an efficient technique for the removal of salts from various solutions.
  • the removal of high salt concentration requires frequent regeneration or renewal of ion exchange resins and is linked to high operation costs.
  • the majority of organic and mineral salts are removed by precipitation of the salts and further evaporation of the 1,2-propanediol on a falling film evaporator, a wiped film evaporator, a thin film evaporator or a short path evaporator.
  • Ion exchange may be used primarily to remove residual ionic impurities. Fouling of the resin is thus reduced, avoiding frequent regeneration and/or replacement of the ion exchange resins and preventing high operation costs.
  • so-called ion exchange resins may further be used for the removal of other impurities.
  • ion exchange resins may be used for adsorption of various organic impurities.
  • Ion exchange is a well-known technique and may be carried out with any suitable resin.
  • ion exchange resins are selected from strong anion exchange resins, weak anion exchange resins, strong cation exchange resins and weak cation exchange resins, or mixtures thereof, e.g. well known mixed-bed type ion exchange resins.
  • the ion exchange step may consist in a treatment on any combination of the above-mentioned ion exchange resins.
  • Further purification of the 1,2-propanediol may further comprise adsorption of impurities on adsorbent solids.
  • adsorption refers to the collection of impurities onto the surface of an adsorbent solid. This adsorption step allows removal of impurities, which are bound to the adsorbent solid by chemical or physical attraction.
  • activated charcoal or other solid adsorbents are used to remove impurities from the purified 1,2-propanediol.
  • ion exchange resins may also be used for adsorption of such impurities.
  • adsorption and/or ion exchange are performed after distillation, thus reducing fouling of the solid adsorbent and minimizing costs.
  • an ion exchange step and/or adsorption step is performed at the end of the distillation sequence, to produce pure 1,2-propanediol from distilled 1,2-propanediol.
  • addition of water to the distilled 1,2-propanediol may be needed to prevent degradation of the resin or adsorbent solid degradation and/or to decrease viscosity, thus increasing mass transfer coefficients and adsorption efficiency.
  • water may have to be added in proportions ranging from 1 and 100%, more preferably from 10 and 20%.
  • Figure 1 Method for purifying 1,2-propanediol from a fermentation broth with one pass of solvent.
  • Microfiltration Ultrafiltration (3) Nano filtration (4) Water evaporation (5) Addition of the solvent (6)
  • Solid-Liquid separation unit (8)
  • Solvent and water evaporation (9) Evaporation on a falling film or wiped film wherein 1,2-propanediol, light products and a fraction of the heavy products are recovered in the vapour phase whereas salts crystallize in the evaporator and are drawn out mechanically at the bottom of the evaporator by scraping (10)
  • Topping elimination of light impurities by distillation (11)
  • Stripping elimination of heavy impurities by distillation.
  • Figure 2 Method for purifying 1,2-propanediol from a fermentation broth with two passes of solvent.
  • Figure 3 Method for purifying 1,2-propanediol from a fermentation broth with one pass of solvent and a final purification.
  • the (Al) filtered fermentation broth was first concentrated by evaporation.
  • (Al) Filtered fermentation broth (55.6 kg) was loaded into a thermosyphon-type evaporator. Operating top pressure was 120 mbar. 84.6 wt% of the solution was evaporated. 8.3 kg of a MPG-rich mixture (Bl) was recovered. This concentrate mixture was analyzed by HPLC and results are reported in Table 1.
  • the solid-liquid mixture is filtered to separate 1770 g of (CI) solution and 55 of wet (Dl) cake filtration. 160 g of (Bl)-ethanol mixture were lost due to the filtration process hold-up.
  • the (Fl) MPG-rich mixture obtained was fed to a laboratory wiped thin film evaporator with an internal condenser.
  • the operating pressure was set to 25 mbar.
  • the heating temperature was set to 140 °C up to 170°C.
  • Valuable compounds, including most part of the MPG, were evaporated. Remaining salts and heavy compounds were collected in the bottom product.
  • the recovered mass of (Gl) distillate was 332 g, and the distillate to feed mass ratio was 70.2%.

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  • Organic Chemistry (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des procédés de purification du 1,2-propanediol à partir d'un bouillon de fermentation comprenant la précipitation de sels par ajout d'un solvant et évaporation de l'alcool sur un évaporateur à film tombant, un évaporateur à film raclé, un évaporateur à film mince ou un évaporateur à trajet court.
PCT/EP2010/070102 2009-12-22 2010-12-17 Procédé de purification du 1,2-propanediol à partir d'un bouillon de fermentation Ceased WO2011076690A1 (fr)

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US28894209P 2009-12-22 2009-12-22
US61/288,942 2009-12-22
EP09306305 2009-12-22
EP09306305.5 2009-12-22

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Cited By (6)

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CN105597351A (zh) * 2016-03-15 2016-05-25 新疆美克化工股份有限公司 高沸物回收装置
CN105924331A (zh) * 2016-04-28 2016-09-07 湖南尔康制药股份有限公司 一种丙二醇的精制方法
WO2017042602A1 (fr) 2015-09-10 2017-03-16 Metabolic Explorer Nouvelles lactaldéhydes réductases pour la production de 1,2-propanédiol
CN106748648A (zh) * 2016-12-02 2017-05-31 苏州苏震生物工程有限公司 一种1,3‑丙二醇发酵液脱盐除杂系统及方法
EP3342873A1 (fr) 2016-12-29 2018-07-04 Metabolic Explorer Conversion de méthylglyoxale en hydroxyacétone utilisant des enzymes et applications associées
CN110573625A (zh) * 2017-04-28 2019-12-13 Gs 加德士 二醇的制备方法

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WO2010037843A1 (fr) * 2008-10-03 2010-04-08 Metabolic Explorer Procédé de purification d'un alcool à partir d'un bouillon de fermentation à l’aide d’un évaporateur à film tombant, à film essuyé, à film mince ou d’un évaporateur moléculaire

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WO2010037843A1 (fr) * 2008-10-03 2010-04-08 Metabolic Explorer Procédé de purification d'un alcool à partir d'un bouillon de fermentation à l’aide d’un évaporateur à film tombant, à film essuyé, à film mince ou d’un évaporateur moléculaire

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Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017042602A1 (fr) 2015-09-10 2017-03-16 Metabolic Explorer Nouvelles lactaldéhydes réductases pour la production de 1,2-propanédiol
CN105597351A (zh) * 2016-03-15 2016-05-25 新疆美克化工股份有限公司 高沸物回收装置
CN105924331A (zh) * 2016-04-28 2016-09-07 湖南尔康制药股份有限公司 一种丙二醇的精制方法
CN106748648A (zh) * 2016-12-02 2017-05-31 苏州苏震生物工程有限公司 一种1,3‑丙二醇发酵液脱盐除杂系统及方法
EP3342873A1 (fr) 2016-12-29 2018-07-04 Metabolic Explorer Conversion de méthylglyoxale en hydroxyacétone utilisant des enzymes et applications associées
WO2018122388A1 (fr) 2016-12-29 2018-07-05 Metabolic Explorer Conversion du méthylglyoxal en hydroxyacétone à l'aide de nouvelles enzymes et applications associées
CN110573625A (zh) * 2017-04-28 2019-12-13 Gs 加德士 二醇的制备方法

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