WO2024228199A1 - Procédés de production d'acide lactique avec récupération et réutilisation simultanées de ses sous-produits - Google Patents

Procédés de production d'acide lactique avec récupération et réutilisation simultanées de ses sous-produits Download PDF

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WO2024228199A1
WO2024228199A1 PCT/IL2024/050421 IL2024050421W WO2024228199A1 WO 2024228199 A1 WO2024228199 A1 WO 2024228199A1 IL 2024050421 W IL2024050421 W IL 2024050421W WO 2024228199 A1 WO2024228199 A1 WO 2024228199A1
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acid
process according
sodium
ammonium
potassium
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Tal SHAPIRA
Maarten Campman
Nitsan Papo
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TripleW Ltd
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TripleW Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/02—Preparation of carboxylic acids or their salts, halides or anhydrides from salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
    • C01D3/00—Halides of sodium, potassium or alkali metals in general
    • C01D3/04—Chlorides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
    • C01D3/00—Halides of sodium, potassium or alkali metals in general
    • C01D3/10—Bromides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
    • C01D5/00—Sulfates or sulfites of sodium, potassium or alkali metals in general
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
    • C01D7/00—Carbonates of sodium, potassium or alkali metals in general
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01D—COMPOUNDS OF ALKALI METALS, i.e. LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CAESIUM, OR FRANCIUM
    • C01D9/00—Nitrates of sodium, potassium or alkali metals in general
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F5/00—Compounds of magnesium
    • C01F5/24—Magnesium carbonates
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F5/00—Compounds of magnesium
    • C01F5/26—Magnesium halides
    • C01F5/30—Chlorides
    • C—CHEMISTRY; METALLURGY
    • C01—INORGANIC CHEMISTRY
    • C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
    • C01F5/00—Compounds of magnesium
    • C01F5/40—Magnesium sulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/41—Preparation of salts of carboxylic acids
    • C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part

Definitions

  • the present invention relates to processes for preparing lactic acid with concurrent recovery and recycling of residues and by-products formed therein.
  • Lactic acid is the most widely occurring hydroxycarboxylic acid with applications in food, chemical, pharmaceutical, and cosmetic industries. This naturally occurring organic acid can be produced by chemical synthesis or microbial fermentation. When produced by microbial fermentation, care should be taken to avoid endogenous decrease in pH due to the formation of lactic acid in order to maintain the productivity of the microorganisms.
  • a pH in the range of 5-7 is preferable and can be obtained by the addition of bases such as monovalent or divalent hydroxides that neutralize the lactic acid thereby producing a lactate salt with the corresponding monovalent or divalent cations. In order to convert the lactate salt to lactic acid, an acidification step needs to be performed.
  • GB 173,479 describes a process of purifying lactic acid, characterized by lactic acid, or its salts, being first converted into magnesium lactate which (if necessary after purification) is decomposed with acid and extracted at ordinary temperature or with heat in a suitable solvent, such as ether, acetone or the like, after the distillation of which pure lactic acid remains.
  • WO 2000/017378 describes a process for the preparation of lactic acid, comprising a fermentation reaction carried out at a pH in the range of between 5.5 to 6.5, wherein the pH is adjusted to said range by introducing into the reaction mixture M(0H)2, wherein M is Ca or Mg, to obtain M-lactate-containing broth and recovering the lactic acid from said M-lactate by reacting the same with HC1, either by treating the M-lactate-containing broth with HC1 or by precipitating M-lactate from the broth, and subsequently reacting said precipitate with HC1, to yield a lactic acid solution, and extracting and/or purifying lactic acid from said solution.
  • WO 2005/123647 describes a process for the preparation of lactic acid and/or lactate from a medium comprising magnesium lactate, wherein the magnesium lactate is reacted with a hydroxide of sodium, potassium, calcium, and/or ammonium at a pH range between 9 and 12, preferably between 9.5 and 11, to form a lactate of sodium, potassium, calcium and/or ammonia and magnesium hydroxide.
  • WO 2011/095631 describes a process for the preparation of lactic acid comprising the steps of: a) providing an aqueous medium comprising magnesium lactate; b) adding to the aqueous medium comprising magnesium lactate a monovalent base to form an aqueous medium comprising a water soluble monovalent lactate salt and a solid magnesium base; c) separating the magnesium base from the aqueous medium comprising the water soluble monovalent lactate salt; d) adjusting the concentration of the monovalent lactate salt in the aqueous medium to a value between 10 and 30 wt.%; e) subjecting the aqueous medium comprising the monovalent lactate salt to watersplitting electrodialysis, to produce a first solution comprising monovalent base and a second solution comprising lactic acid and monovalent lactate salt, the electrodialysis being carried out to a partial conversion of 40 to 98 mole%; f) separating the second solution comprising lactic acid and monovalent lactate salt into lactic acid and
  • WO 2023/006876 describes a process for the preparation of lactic acid comprising the steps of: a) providing an aqueous medium comprising magnesium lactate; b) adding to the aqueous medium comprising magnesium lactate a monovalent base to form an aqueous medium comprising a water soluble monovalent lactate salt and a solid magnesium base; c) separating the solid magnesium base from the aqueous medium comprising the water soluble monovalent lactate salt; d) providing an aqueous medium comprising the water soluble monovalent lactate salt at a concentration of more than 30 wt.% and at most 45 wt.%; e) subjecting the aqueous medium comprising the water soluble monovalent lactate salt from step d) to water-splitting electrodialysis, to produce a first solution comprising monovalent base and a second solution comprising lactic acid and monovalent lactate salt, the electrodialysis being carried out to a partial conversion of 40 to 99 mole%; f) recovering
  • the present invention provides processes for preparing high-purity lactic acid with minimal by-products and residues.
  • the present invention provides a process which comprises the acidification of a lactate salt containing divalent cations using an acid thereby obtaining lactic acid and a salt residue containing the divalent cations, reacting the salt residue containing the divalent cations with a monovalent base thereby obtaining a divalent base and a salt residue containing the monovalent cations, and subjecting the salt residue containing the monovalent cations to subsequent use or to electrodialysis thereby obtaining a monovalent base and an acid.
  • the present invention provides a process which comprises reacting a lactate salt containing monovalent cations with a salt containing divalent cations thereby obtaining a lactate salt containing the divalent cations and a salt residue containing the monovalent cations, subjecting the salt residue containing the monovalent cations to subsequent use or to electrodialysis thereby obtaining a monovalent base and an acid, and acidification of a lactate salt containing divalent cations using an acid thereby obtaining lactic acid and a salt residue containing the divalent cations.
  • the present invention provides a process which comprises reacting a lactate salt containing divalent cations with a monovalent base thereby obtaining a divalent base and a lactate salt containing the monovalent cations, acidification of the lactate salt containing monovalent cations using an acid thereby obtaining lactic acid and a salt residue containing the monovalent cations, and subjecting the salt residue containing the monovalent cations to subsequent use or to electrodialysis thereby obtaining a monovalent base and an acid.
  • the present invention provides a process which comprises acidification of a lactate salt containing monovalent cations using an acid thereby obtaining lactic acid and a salt residue containing the monovalent cations, and subjecting the salt residue containing the monovalent cations to subsequent use or to electrodialysis thereby obtaining a monovalent base and an acid.
  • the by-products of lactic acid formation obtained by the processes of the present invention are recovered and recycled, preferably as reagents in the various steps of the processes therefore providing economically and environmentally beneficial processes which are essentially free of undesired residues and by-products.
  • the present invention is based, in part, on the unexpected finding of by-product free processes for preparing lactic acid from a lactate salt. Contrary to hitherto known processes of acidulation of a lactate salt which typically produce large quantities of residual by-products, the processes of the present invention afford nearly zero byproducts as they utilize multiple steps that are designed to recycle the by-products, for example as reagents that can be reused in the processes. Furthermore, the processes disclosed herein directly produce lactic acid in high purity and enhanced yield.
  • the present invention provides a process for the preparation of lactic acid, the process comprising the steps of: a. providing an aqueous medium comprising a lactate salt with divalent cations; b. adding an acid to the aqueous medium of step (a) to obtain lactic acid and a salt residue comprising the divalent cations; c. reacting the salt residue comprising the divalent cations of step (b) with a first base comprising monovalent cations to obtain a second base comprising the divalent cations and a salt residue comprising the monovalent cations; and d. collecting the salt residue comprising the monovalent cations of step (c), wherein the second base comprising the divalent cations of step (c) is recovered and reused in the process of producing an aqueous medium of step (a).
  • the divalent cations are magnesium ions. According to other embodiments, the divalent cations are calcium ions.
  • the acid in step (b) is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment.
  • the acid in step (b) is sulfuric acid.
  • the salt residue comprising the divalent cations is magnesium sulfate (e.g., magnesium sulfate heptahydrate).
  • the lactic acid obtained in step (b) is recovered using an organic solvent.
  • the organic solvent is selected from the group consisting of a ketone, an ether, an aldehyde, and a mixture thereof. Each possibility represents a separate embodiment.
  • the lactic acid obtained in step (b) is recovered using acetone.
  • the salt residue comprising the divalent cations obtained in step (b) is recovered using an organic solvent before being used in step (c).
  • the organic solvent is selected from the group consisting of a ketone, an ether, an aldehyde, and a mixture thereof. Each possibility represents a separate embodiment.
  • the salt residue comprising the divalent cations obtained in step (b) is recovered using acetone.
  • the organic solvent is at a temperature of about 5°C to about 25°C, including each value within the specified range.
  • the first base comprising monovalent cations in step (c) is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide, and a mixture thereof. Each possibility represents a separate embodiment.
  • the second base comprising the divalent cations in step (c) is magnesium hydroxide.
  • the salt residue comprising the monovalent cations is selected from the group consisting of sodium sulfate, potassium sulfate, ammonium sulfate, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium nitrate, potassium nitrate, ammonium nitrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, sodium phosphate, potassium phosphate, ammonium phosphate, and combinations thereof.
  • the salt residue comprising the monovalent cations is sodium sulfate.
  • the salt residue comprising the monovalent cations is ammonium sulfate.
  • the process further comprises step (e) of subjecting the collected salt residue comprising the monovalent cations of step (d) to electrodialysis thereby obtaining a base comprising the monovalent cations and an acid, wherein the base comprising the monovalent cations is recovered and reused as the first base in step (c), and/or the acid is recovered and reused in step (b).
  • the present invention provides a process for the preparation of lactic acid, the process comprising the steps of: a. providing an aqueous medium comprising a lactate salt with monovalent cations; b. reacting the lactate salt with monovalent cations of step (a) with a first salt comprising divalent cations to obtain a lactate salt with divalent cations and a second salt residue comprising the monovalent cations; c. adding an acid to the lactate salt with divalent cations of step (b) to obtain lactic acid and a salt residue comprising the divalent cations; and d. collecting the second salt residue comprising the monovalent cations of step (b), wherein the salt residue comprising the divalent cations of step (c) is recovered and reused as the first salt in step (b).
  • the monovalent cations are sodium ions. According to other embodiments, the monovalent cations are ammonium ions.
  • the first salt comprising the divalent cations is magnesium sulfate (e.g., magnesium sulfate heptahydrate).
  • the acid in step (c) is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment.
  • the acid in step (c) is sulfuric acid.
  • the lactic acid obtained in step (c) is recovered using an organic solvent as detailed above.
  • the salt residue comprising the divalent cations of step (c) is recovered using an organic solvent as detailed above before being reused in step (b).
  • the second salt residue comprising the monovalent cations is selected from the group consisting of sodium sulfate, potassium sulfate, ammonium sulfate, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium nitrate, potassium nitrate, ammonium nitrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, sodium phosphate, potassium phosphate, ammonium phosphate, and combinations thereof.
  • the salt residue comprising the monovalent cations is sodium sulfate.
  • the salt residue comprising the monovalent cations is ammonium sulfate.
  • the process further comprises step (e) of subjecting the collected second salt residue comprising the monovalent cations of step (d) to electrodialysis thereby obtaining a base comprising the monovalent cations and an acid, wherein the base comprising the monovalent cations is recovered and reused in the process of producing an aqueous medium of step (a), and/or the acid is recovered and reused in step (c).
  • the present invention provides a process for the preparation of lactic acid, the process comprising the steps of: a. providing an aqueous medium comprising a lactate salt with divalent cations; b. reacting the lactate salt with divalent cations of step (a) with a first base comprising monovalent cations to obtain a second base comprising the divalent cations and a lactate salt comprising the monovalent cations; c. adding an acid to the lactate salt comprising the monovalent cations of step (b) to obtain lactic acid and a salt residue comprising the monovalent cations; and d.
  • step (c) performing electrodialysis on the salt residue comprising the monovalent cations of step (c) to obtain a base comprising the monovalent cations and an acid, wherein the second base comprising the divalent cations of step (b) is recovered and reused in the process of producing an aqueous medium of step (a), the base comprising the monovalent cations of step (d) is recovered and reused as the first base in step (b), and/or the acid in step (d) is recovered and reused in step (c).
  • the divalent cations are magnesium ions. According to other embodiments, the divalent cations are calcium ions.
  • the first base comprising monovalent cations in step (b) is selected from the group consisting of sodium hydroxide, potassium hydroxide, ammonium hydroxide, and a mixture thereof. Each possibility represents a separate embodiment.
  • the second base comprising the divalent cations in step (b) is magnesium hydroxide.
  • the acid in step (c) is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment.
  • the acid in step (c) is sulfuric acid.
  • the lactic acid obtained in step (c) is recovered using an organic solvent as detailed above.
  • the salt residue comprising the monovalent cations obtained in step (c) is selected from the group consisting of sodium sulfate, potassium sulfate, ammonium sulfate, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium nitrate, potassium nitrate, ammonium nitrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, sodium phosphate, potassium phosphate, ammonium phosphate, and combinations thereof.
  • the salt residue comprising the monovalent cations is sodium sulfate.
  • the present invention provides a process for the preparation of lactic acid, the process comprising the steps of: a. providing an aqueous medium comprising a lactate salt with monovalent cations; b. adding an acid to the lactate salt with monovalent cations of step (a) to obtain lactic acid and a salt residue comprising the monovalent cations; and c.
  • step (b) performing electrodialysis on the salt residue comprising the monovalent cations of step (b) to obtain a base comprising the monovalent cations and an acid, wherein the base comprising the monovalent cations of step (c) is recovered and reused in the process of producing an aqueous medium of step (a), and/or the acid in step (c) is recovered and reused in step (b).
  • the acid for the acidulation of the lactate salt with monovalent cations to obtain lactic acid is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment.
  • the acid for the acidulation of the lactate salt with monovalent cations to obtain lactic acid is sulfuric acid.
  • the lactic acid obtained is recovered using an organic solvent as detailed above.
  • the salt residue comprising the monovalent cations is selected from the group consisting of sodium sulfate, potassium sulfate, ammonium sulfate, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium nitrate, potassium nitrate, ammonium nitrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, sodium phosphate, potassium phosphate, ammonium phosphate, and combinations thereof.
  • the salt residue comprising the monovalent cations is sodium sulfate.
  • the electrodialysis on the salt residue comprising the monovalent cations in the processes disclosed therein is bipolar membrane electrodialysis (BPED).
  • the electrodialysis is electroelectrodialysis (EED).
  • the electrodialysis is water-splitting electrodialysis.
  • the base obtained in the electrodialysis is selected from sodium hydroxide, potassium hydroxide, and ammonium hydroxide.
  • the acid obtained in electrodialysis is selected from the group consisting of sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof.
  • the aqueous medium comprising a lactate salt of the present processes is derived from decomposed organic waste.
  • the decomposed organic waste is obtained from a lactic acid fermentation.
  • the organic waste comprises a carbohydrate source.
  • the organic waste is selected from the group consisting of food waste, municipal food waste, residential food waste, agricultural waste, industrial food waste from food processing facilities, commercial food waste (from hospitals, restaurants, shopping centers, airports etc.), and a mixture or combination thereof. Each possibility represents a separate embodiment.
  • Food waste in accordance with the present invention encompasses food waste and beverages of plant origin and/or animal origin.
  • Food waste according to the present invention is typically mixed food waste, comprising one or more of bakery waste, dairy waste, animal-origin food waste including meat, poultry and fish waste, fruit and vegetable waste, and grain-based food waste (e.g., rice, couscous, pasta, noodles).
  • grain-based food waste e.g., rice, couscous, pasta, noodles.
  • mixed food waste according to the present invention comprises a combination of food wastes selected from bakery waste, dairy waste, animal-origin food waste including meat, poultry and fish waste, fruit and vegetable waste, and grain-based food waste (e.g., rice, couscous, pasta, noodles).
  • grain-based food waste e.g., rice, couscous, pasta, noodles
  • Food waste typically comprises solid components originating from food products or residues, e.g., food particles and debris, bones and bone fragments, shells and shell fragments, seeds and seed fragments, peels and the like, and also solids that do not originate from food products or residues, e.g., plastics, glass and metals, originating, for example, from packaging material.
  • solid components originating from food products or residues, e.g., food particles and debris, bones and bone fragments, shells and shell fragments, seeds and seed fragments, peels and the like, and also solids that do not originate from food products or residues, e.g., plastics, glass and metals, originating, for example, from packaging material.
  • the substrate for the lactic acid fermentation is a slurry of organic waste, particularly a slurry of food waste, or a liquid phase separated from a slurry of organic waste or pretreated slurry of organic waste.
  • An organic waste slurry e.g., a food waste slurry
  • An organic waste slurry is typically characterized by a solid content (dry matter content) in the range of 5-50%, including each value within the specified range.
  • an organic waste slurry is characterized by a solid content in the range of 10-30%, including each value within the specified range.
  • an organic waste slurry is characterized by a solid content in the range of 15-35%, including each value within the specified range.
  • an organic waste slurry is characterized by a water content in the range of 50-95%, including each value within the specified range. In some embodiments, an organic waste slurry is characterized by a water content in the range of 70%-90%, including each value within the specified range. In other embodiments, an organic waste slurry is characterized by a water content in the range of 65%-85%, including each value within the specified range.
  • the decomposed organic waste is obtained from a lactic acid-containing waste. According to other embodiments, the decomposed organic waste is obtained from hydrolysis of polylactic acid polymer.
  • the decomposed organic waste comprises lactic acid by-product that is derived from an industrial production of polylactic acid. In other embodiments, the decomposed organic waste comprises lactic acid by-product that is derived from industrial purification of lactic acid. In yet other embodiments, the decomposed organic waste comprises lactic acid obtained from hydrolyzing lactide byproduct from an industrial production of poly lactic acid.
  • the recovery of any one of the salt residues of the present processes can be performed using at least one of filtration, centrifugation, flotation, sedimentation, coagulation, flocculation, and decantation.
  • filtration e.g., microfiltration
  • centrifugation e.g., flotation
  • sedimentation e.g., sedimentation
  • coagulation e.g., flocculation
  • decantation e.g., filtration, filtration, microfiltration
  • the salt residues of the present processes are recovered by filtration (e.g., microfiltration) and/or centrifugation and washed with a suitable solvent prior to being reused in the processes.
  • Figure 1 shows a schematic representation of a process according to certain embodiments of the present invention.
  • Figure 2 shows a schematic representation of a process according to certain embodiments of the present invention.
  • Figure 3 shows a schematic representation of a process according to certain embodiments of the present invention.
  • Figure 4 shows a schematic representation of a process according to certain embodiments of the present invention.
  • Figure 5 shows a schematic representation of an electro-electrodialysis cell according to certain embodiments of the present invention.
  • the present invention provides processes for the production of lactic acid from a lactate salt solution or dispersion further comprising monovalent or divalent cations.
  • the processes disclosed herein for the first time provide lactic acid production with minimal to no by-products or residues as the by-products or residues are recovered and reused, for example by recycling them back to different steps of the processes. In this manner, eco- friendly recycling processes are provided, which processes are also cost-effective as the reagents utilized therein can be obtained from previous productions.
  • the processes of the present invention provide the direct production of lactic acid in high purity and yield.
  • Lactic acid production is performed from an aqueous medium containing magnesium lactate.
  • the aqueous medium containing magnesium lactate is derived from decomposed organic waste.
  • organic waste recycling is performed via fermentation of organic waste from municipal waste, food waste and agricultural waste utilizing L-lactic acid-producing microorganisms e.g., Bacillus coagulans. Due to the formation of L-lactic acid, endogenous lowering of the pH occurs. This endogenous lowering of the pH adversely affects the performance of the microorganisms.
  • the fermentation process is typically carried out in the presence of an alkaline substance to adjust the pH during fermentation.
  • the alkaline substance neutralizes the pH resulting in the formation of L-lactate ions and counterions.
  • the alkaline substance utilized is magnesium hydroxide resulting in a fermentation broth comprising magnesium lactate.
  • magnesium sulfate When the magnesium lactate is acidified to lactic acid, using e.g., sulfuric acid, magnesium sulfate is obtained as a by-product. While the main stream of lactic acid production continues to downstream processing of lactic acid purification and separation, the magnesium sulfate by-product is subjected to a side sub-process which affords its recycling back to the process. In particular, the magnesium sulfate is subjected to a step of ion exchange or swap of the magnesium ions with sodium ions using a strong base (NaOH) to result in Mg(0H)2 and Na 2 SO 4 .
  • a strong base NaOH
  • the magnesium hydroxide can then be separated and used in a subsequent fermentation process to maintain the pH during fermentation at the appropriate range suitable for the proper operation of the microorganisms.
  • This mode of operation is highly advantageous by utilizing the alkaline substance formed during one batch production of lactic acid as the source of alkaline substance in a subsequent production of lactic acid.
  • the scheme further demonstrates the subsequent recycling of the Na 2 SO 4 byproduct of the swap reaction using electrodialysis to result in the production of NaOH and sulfuric acid.
  • the NaOH can be used for a subsequent swap reaction in this side sub-process
  • the sulfuric acid can be utilized for the acidification of the main process of lactic acid formation by protonating the lactate salt.
  • Figure 2 demonstrating certain features according to embodiments of the present invention. Lactic acid production is performed from an aqueous medium containing sodium lactate.
  • the aqueous medium can be obtained, for example, from a fermentation broth in which NaOH is used as the alkaline substance to adjust the pH.
  • the sodium lactate is subjected to a step of ion exchange or swap of the sodium ions with magnesium ions using a salt, for example MgSCU, to produce magnesium lactate and Na 2 SO 4 .
  • the magnesium lactate is then acidified to lactic acid, using e.g., sulfuric acid, and magnesium sulfate is obtained as a by-product. While the main stream of lactic acid production continues to downstream processing of lactic acid purification and separation, the magnesium sulfate by-product is recovered and reused for a subsequent ion swap of the sodium ions with magnesium ions.
  • the Na 2 SO 4 obtained as a by-product of the ion swap is recycled using electrodialysis to result in the production of NaOH and sulfuric acid
  • the sulfuric acid can be utilized for the acidification of the main process of lactic acid formation by protonating the lactate salt.
  • the NaOH can be used as the alkaline substance to adjust the pH during fermentation to obtain an aqueous medium containing sodium lactate.
  • Lactic acid production is performed from an aqueous medium containing magnesium lactate which may be derived, for example, from lactic acid fermentation using magnesium hydroxide as an alkaline pH-adjusting agent as detailed above.
  • the magnesium lactate is subjected to a step of ion exchange or swap of the magnesium ions with sodium ions using a first base, for example NaOH, to produce sodium lactate and magnesium hydroxide as the second base.
  • the sodium lactate is then acidified to lactic acid, using e.g., sulfuric acid, and sodium sulfate is obtained as a byproduct.
  • the sulfuric acid can be utilized for the acidulation of the main process of lactic acid formation by protonating the lactate salt.
  • the NaOH can be used as the alkaline substance for the magnesium to sodium swap reaction.
  • Lactic acid production is performed from an aqueous medium containing sodium lactate which may be derived, for example, from lactic acid fermentation using sodium hydroxide as an alkaline pH-adjusting agent as detailed above.
  • the sodium lactate is acidified to lactic acid, using e.g., sulfuric acid, and sodium sulfate is obtained as a by-product.
  • the sulfuric acid can be utilized for the acidulation of the main process of lactic acid formation by protonating the lactate salt.
  • the NaOH can be used as the alkaline substance to adjust the pH during fermentation to obtain an aqueous medium containing sodium lactate.
  • substantially all residues and byproducts are recovered and reused in the processes of the present invention.
  • the processes disclosed herein are therefore environmentally highly advantageous in avoiding residues that need to be discarded.
  • the processes of the present invention also afford cost savings as expensive reagents are recycled and reused.
  • commercial production of lactic acid in high purity and yield is provided, the lactic acid being particularly suitable for the preparation of polylactic acid.
  • an aqueous medium comprising lactate ions and divalent or monovalent counterions is obtained.
  • the aqueous medium may be derived from decomposed organic waste or from a sugar fermentation process that produces a fermentation broth comprising lactate ions and divalent or monovalent counterions.
  • a fermentation broth containing lactate ions for use according to the present invention may be derived from lactic acid fermentation of various carbohydrate sources, including starch-based and cellulose-based carbohydrate sources.
  • carbohydrate sources for fermentation include starches such as corn, potato and cassava starches, and cane sugar. Each possibility represents a separate embodiment.
  • the carbohydrate source is organic waste, including starch-rich organic waste, lignocellulose-rich waste and dairy waste. Exemplary organic waste sources are detailed below.
  • the aqueous medium is a decomposition product of any lactic acid-containing waste such as, but not limited to, polylactic acid polymer which was subjected to hydrolysis.
  • a fermentation broth derived from organic waste feedstocks is used.
  • Organic waste feedstocks within the scope of the present invention can be obtained from any waste source including, but not limited to, food waste, municipal food waste, residential food waste, agricultural waste, industrial food waste from food processing facilities, commercial food waste (from hospitals, restaurants, shopping centers, airports etc.), and a mixture or combination thereof. Each possibility represents a separate embodiment.
  • the organic waste can additionally originate from residues ranging from animal and human excreta, vegetable and fruit residues, plants, cooked food, protein residues, slaughter waste, and combinations thereof.
  • Industrial organic food waste may include factory waste such as by products, factory rejects, market returns or trimmings of inedible food portions (such as skin, fat, crusts and peels). Each possibility represents a separate embodiment.
  • Commercial organic food waste may include waste from shopping malls, restaurants, supermarkets, etc. Each possibility represents a separate embodiment.
  • the aqueous medium is a fermentation broth obtained from a fermentation process of a carbohydrate source.
  • the fermentation broth typically comprises insoluble organic -based impurities such as, but not limited to, microorganisms (e.g., lactic acid producing microorganisms including e.g., yeasts, bacteria and fungi), fats and oils, lipids, aggregated proteins, bone fragments, hair, precipitated salts, cell debris, fibers (e.g., fruit and/or vegetables peels), and residual unprocessed waste (e.g., food shells, seeds, food insoluble particles and debris, etc.).
  • microorganisms e.g., lactic acid producing microorganisms including e.g., yeasts, bacteria and fungi
  • fats and oils lipids
  • aggregated proteins e.g., bone fragments, hair, precipitated salts
  • cell debris e.g., fruit and/or vegetables peels
  • residual unprocessed waste e.g.
  • Non-limiting examples of insoluble inorganic -based impurities include plastics, glass, residues from food packaging, sand, and combinations thereof. Each possibility represents a separate embodiment.
  • the insoluble impurities are removed from the fermentation broth. Removal of insoluble impurities can be achieved, for example, using at least one of filtration, centrifugation, flotation, sedimentation, coagulation, flocculation, and decantation. Each possibility represents a separate embodiment. Typically, removal is performed using filtration (e.g., microfiltration) and/or centrifugation.
  • Non-limiting examples of soluble impurities include water, solvents, polysaccharides, starch, cellulose, hemicellulose, lignin, seed fragment, salts, color components (e.g., tannins, flavonoids and carotenoids), and combinations thereof. Each possibility represents a separate embodiment.
  • the soluble and insoluble impurities content of the broth is identical to the soluble and insoluble impurities content of the organic waste feedstocks.
  • the soluble and insoluble impurities content of the broth is lower by at least about 1 wt.% compared to the soluble and insoluble impurities content of the organic waste feedstocks.
  • the soluble and insoluble impurities content of the broth is lower by at least about 5 wt.%, about 10 wt.%, about 15 wt.%, about 20 wt.%, about 30 wt.%, about 40 wt.%, or about 50 wt.% compared to the soluble and insoluble impurities content of the organic waste feedstocks.
  • Each possibility represents a separate embodiment.
  • the non-homogenous feedstock for the lactic acid fermentation is a slurry of organic waste, particularly food waste, or a liquid phase separated from a slurry of organic waste or pretreated slurry of organic waste (e.g., a slurry of organic waste that was subjected to saccharification and sterilization).
  • a slurry of organic waste refers to a mixture of the organic waste and water, typically containing solid particles of the organic waste.
  • a slurry of organic waste is typically formed by collecting waste material from various sources, subjecting the waste material to separation of plastics and inorganic solid components such as glass, metal and sand (to remove most and preferably all of the plastics and inorganic solid components), reducing the particle size of the waste material, e.g., by shredding or grinding, adding water if necessary, and forming a suspension of organic waste material in the water.
  • forming a slurry of organic waste particularly a slurry of food waste, comprises subjecting the waste to depackaging, namely, removal of packaging material, including plastic, metal and glass packaging material.
  • the organic waste may naturally be in the form of a slurry.
  • An organic waste slurry (e.g., a food waste slurry) is typically characterized by a solid content (dry matter content) in the range of 5-50% (namely, characterized by a liquid or moisture content in the range of 50-95%), including each value within the specified ranges.
  • an organic waste slurry is characterized by a solid content in the range of 10-30% (namely, a liquid or moisture content in the range of 70%-90%), including each value within the specified ranges.
  • an organic waste slurry is characterized by a solid content in the range of 15-35% (namely, a liquid or moisture content in the range of 65%-85%), including each value within the specified ranges.
  • the aqueous medium may be a by-product of industrial production of polylactic acid or industrial purification of lactic acid.
  • the aqueous medium is a by-product of hydrolysis of lactide from an industrial production of polylactic acid.
  • the aqueous medium comprises lactate ions at concentrations of about 10 g/L to about 500 g/L, including each value within the specified range.
  • Exemplary lactate concentrations include, but are not limited to, about 10 g/L, about 25 g/L, about 50 g/L, about 75 g/L, about 100 g/L, about 125 g/L, about 150 g/L, about 175 g/L, about 200 g/L, about 225 g/L, about 250 g/L, about 275 g/L, about 300 g/L, about 325 g/L, about 350 g/L, about 375 g/L, about 400 g/L, about 425 g/L, about 450 g/L, about 475 g/L, or about 500 g/L.
  • Each possibility represents a separate embodiment.
  • lactate counterions are divalent ions (e.g., magnesium ions or calcium ions)
  • the lactate salt is acidified or protonated by adding an acid thereby resulting in the formation of lactic acid and a divalent salt residue.
  • the lactate counterions are monovalent ions (e.g., sodium ions or ammonium ions)
  • the lactate salt is acidified or protonated by adding an acid thereby resulting in the formation of lactic acid and a monovalent salt residue.
  • lactic acid refers to the hydroxycarboxylic acid having the following chemical formula CH3CH(OH)CO2H.
  • lactic acid or lactate can refer to the stereoisomers (enantiomers) of lactic acid including L-lactic acid/L-lactate, D-lactic acid/D-lactate, or to a combination thereof. Each possibility represents a separate embodiment.
  • Any acid can be utilized in acidulation of lactate salt including, but not limited to, organic or inorganic acids.
  • Such acids include hydrochloric, hydrofluoric, trifluoroacetic, sulfuric, phosphoric, acetic, succinic, citric, lactic, maleic, fumaric, palmitic, cholic, pamoic, mucic, D-glutamic, D-camphoric, glutaric, phthalic, tartaric, lauric, stearic, salicylic, methanesulfonic, benzenesulfonic, sorbic, picric, benzoic, cinnamic, and the like.
  • Each possibility represents a separate embodiment.
  • Exemplary acids include, but are not limited to, sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment. Currently preferred is the use of sulfuric acid.
  • the addition of an acid is performed at elevated temperatures, for example at about 40°C to about 80°C, preferably about 50°C to about 70°C, including each value within the specified ranges.
  • Exemplary temperatures include, but are not limited to, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, about 70°C, about 75°C, and about 80°C.
  • Each possibility represents a separate embodiment.
  • the addition can be performed while cooling, for example using a cooling jacket to maintain the temperatures at the desired range.
  • the rate of addition may vary but typically includes a slow rate to maintain the temperature at the desired range and avoid overheating.
  • Suitable rates at which acid can be added include, but are not limited to, about 0.5% to about 5% per minute, for example about 1% to about 4% per minute, including each value within the specified ranges.
  • Exemplary rates include, but are not limited to, about 0.5%/min, about 1%/min, about 1.5%/min, about 2%/min, about 2.5%/min, about 3%/min, about 3.5%/min, about 4%/min, about 4.5%/min, and about 5%/min. Each possibility represents a separate embodiment.
  • Suitable organic solvents within the scope of the present invention include, but are not limited to, ketones, aldehydes, ethers, esters, nitriles, amides, halogenated hydrocarbons, aromatic hydrocarbons, and mixtures or combinations thereof. Each possibility represents a separate embodiment.
  • Exemplary organic solvents include, but are not limited to, ketones, ethers, aldehydes, and a mixture thereof. Each possibility represents a separate embodiment.
  • ketones particularly acetone or ethyl acetate.
  • the organic solvent being added is typically maintained at lower temperatures in order to avoid solvent evaporation. Suitable temperatures of the organic solvent include 25°C or less, for example about 5°C to about 25°C, preferably about 5°C to about 15°C, including each value within the specified ranges. Exemplary temperatures of the organic solvent include, but are not limited to, about 1°C, about 2°C, about 3 °C, about 4°C, about 5°C, about 6°C, about 7°C, about 8°C, about 9°C, about 10°C, about
  • the organic solvent can be added to the mixture of lactic acid and residual divalent or monovalent salt at a ratio of 1:10 to 10:1, including all iterations of ratios within the specified range.
  • Exemplary ratios include, but are not limited to, 1:10, 1:9, 1:8, 1:7, 1:6, 1:5, 1:4, 1:3, 1:2, 1:1, 2:1, 3:1, 4:1, 5:1, 6:1, 7:1, 8:1, 9:1, or 10:1.
  • Each possibility represents a separate embodiment.
  • the residual divalent or monovalent salt is precipitated and separated from the slurry for use in the side sub-process.
  • the remaining lactic acid-containing mixture is then further processed to collect the lactic acid as is known in the art.
  • MgSO4"7H2O MgSO4"7H2O.
  • monovalent salt residues are formed, they can be collected for subsequent reuse (e.g., ammonium sulfate salt may be isolated and used in agriculture) or subjected to further processing (e.g., electrodialysis) as detailed below.
  • ammonium sulfate salt may be isolated and used in agriculture
  • electrodialysis e.g., electrodialysis
  • ion swap between divalent cations and monovalent cations or vice versa is performed.
  • the ion swap is performed by the addition of a monovalent base to the divalent salt residue or to the divalent lactate salt.
  • Suitable monovalent bases within the scope of the present invention include, but are not limited to, sodium hydroxide, potassium hydroxide, ammonium hydroxide, and a mixture thereof. Each possibility represents a separate embodiment.
  • sodium hydroxide or ammonium hydroxide is preferred.
  • ammonia water aqua ammonia
  • the addition of a monovalent base is performed at temperatures of about 20°C to about 80°C, preferably about 30°C to about 60°C, including each value within the specified ranges.
  • Exemplary temperatures include, but are not limited to, about 20°C, about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, about 70°C, about 75°C, and about 80°C.
  • Each possibility represents a separate embodiment.
  • the present invention also contemplates the addition of the monovalent base in excess. Up to 20% excess of the monovalent base can be added according to the principles of the present invention. Typically, the addition of monovalent base is performed gradually e.g., dropwise. Suitable rates at which the monovalent base can be added include, but are not limited to, about 0.01% to about 5% per minute, for example about 0.5% to about 2.5% per minute, including each value within the specified ranges.
  • Exemplary rates include, but are not limited to, about 0.01%/min, about 0.05%/min, about 0.1%/min, about 0.5%/min, about 1%/min, about 1.5%/min, about 2%/min, about 2.5%/min, about 3%/min, about 3.5%/min, about 4%/min, about 4.5%/min, and about 5%/min. Each possibility represents a separate embodiment.
  • the divalent base includes, but is not limited to, magnesium hydroxide or calcium hydroxide with each possibility representing a separate embodiment.
  • the divalent base thus obtained is recycled back to the process to adjust the pH in the lactic acid fermentation or for hydrolyzing poly lactic acid.
  • ion swap is performed by the addition of a divalent salt to the monovalent lactate.
  • the addition of a divalent salt to the monovalent lactate is performed at temperatures of about 20°C to about 80°C, including each value within the specified range.
  • Exemplary temperatures include, but are not limited to, about 20°C, about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, about 70°C, about 75°C, and about 80°C.
  • temperatures include, but are not limited to, about 20°C, about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, about 70°C, about 75°C, and about 80°C.
  • Each possibility represents a separate embodiment.
  • the present invention also contemplates the addition of the divalent salt in excess. Up to 20% excess of the divalent salt can be added according to the principles of the present invention.
  • salt residues comprising monovalent cations are formed.
  • salt residues that include, but are not limited to, sodium sulfate, potassium sulfate, ammonium sulfate, sodium chloride, potassium chloride, ammonium chloride, sodium bromide, potassium bromide, ammonium bromide, sodium nitrate, potassium nitrate, ammonium nitrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, sodium phosphate, potassium phosphate, ammonium phosphate, and combinations thereof.
  • sodium sulfate or ammonium sulfate Each possibility represents a separate embodiment.
  • the thus obtained monovalent salt by-products are collected for subsequent reuse.
  • ammonium sulfate salt may be isolated and used in agriculture.
  • the thus obtained monovalent salts by-products are subjected to electrodialysis.
  • Electrodialysis apparatuses are typically composed of two electrodes, an anode and a cathode, separated from one another by one or more ion-selective membranes.
  • Ion- selective membranes suitable for use in the present invention include, but are not limited to, anion-selective, cation-selective and bipolar membranes. Each possibility represents a separate embodiment.
  • the aqueous medium comprising the monovalent salt byproducts is introduced into the feed chamber and the monovalent cations are transported from the feed chamber to the base chamber through the cation exchange membrane to produce a base solution comprising the monovalent cations. Simultaneously, anions are transported through the anion exchange membrane to the acid chamber to produce the second solution comprising the acid.
  • the aqueous medium comprising the monovalent salt by-product is introduced into the feed chamber where the acid is formed and the monovalent cations are transported from the feed chamber to the base chamber through the cation exchange membrane to produce a base solution comprising the monovalent cations.
  • the acid and the salt solution i.e., brine
  • the acid may further be separated via distillation before its reused or alternatively reused as a mixture that further comprises the brine.
  • electrodialysis modes of operation selected from the group consisting of water- splitting electrodialysis (WSED), electroelectrodialysis (EED), and bipolar membrane electrodialysis (BPED).
  • WSED water- splitting electrodialysis
  • EED electroelectrodialysis
  • BPED bipolar membrane electrodialysis
  • the flow rate at which the monovalent salt by-product is introduced into the feed chamber is between about 1 dm 3 /h to about 1000 dm 3 /h, for example about 10 dm 3 /h to about 500 dm 3 /h, including each value within the specified ranges.
  • Exemplary flow rates include, but are not limited to, about 1 dm 3 /h, about 5 dm 3 /h, about 10 dm 3 /h, about 20 dm 3 /h, about 30 dm 3 /h, about 40 dm 3 /h, about 50 dm 3 /h, about 60 dm 3 /h, about 70 dm 3 /h, about 80 dm 3 /h, about 90 dm 3 /h, about 100 dm 3 /h, about 200 dm 3 /h, about 300 dm 3 /h, about 400 dm 3 /h, about 500 dm 3 /h, about 600 dm 3 /h, about 700 dm 3 /h, about 800 dm 3 /h, about 900 dm 3 /h, and about 1000 dm 3 /h.
  • the concentration of the monovalent salt fed into the electrodialysis is typically in the range of about 10 g/L to about 200 g/L, for example about 50 g/L to about 200 g/L, including each value within the specified ranges.
  • Exemplary concentrations include, but are not limited to, about 10 g/L, about 20 g/L, about 30 g/L, about 40 g/L, about 50 g/L, about 60 g/L, about 70 g/L, about 80 g/L, about 90 g/L, about 100 g/L, about 110 g/L, about 120 g/L, about 130 g/L, about 140 g/L, about 150 g/L, about 160 g/L, about 170 g/L, about 180 g/L, about 190 g/L, and about 200 g/L. Each possibility represents a separate embodiment.
  • electrodialysis can be performed at room temperatures, it can also be performed at elevated temperatures. Suitable temperatures at which electrodialysis can be performed include from about 20°C to about 80°C, for example from about 40°C to about 70°C, including each value within the specified ranges. Exemplary temperatures for performing the electrodialysis include, but are not limited to, about 20°C, about 25°C, about 30°C, about 35°C, about 40°C, about 45°C, about 50°C, about 55°C, about 60°C, about 65°C, about 70°C, about 75°C, and about 80°C. Each possibility represents a separate embodiment.
  • the products of electrodialysis are an acid and a base comprising monovalent cations.
  • Exemplary bases comprising monovalent cations include, but are not limited to sodium hydroxide, potassium hydroxide, and ammonium hydroxide. Each possibility represents a separate embodiment.
  • Exemplary acids include, but are not limited to, sulfuric acid, hydrochloric acid, hydrobromic acid, nitric acid, carbonic acid, phosphoric acid, and combinations thereof. Each possibility represents a separate embodiment.
  • the products of the electrodialysis are recycled back to the process whereby the acid is reused in the step of acidifying the lactate salt to lactic acid, and the monovalent base is reused in the step of ion-exchange or swap or alternatively as an alkaline substance for obtaining an aqueous medium comprising lactate ions such as, for example, for adjusting the pH in a lactic acid fermentation or for hydrolyzing polylactic acid.
  • the recovery of any one of the solid intermediate products using at least one of filtration, centrifugation, flotation, sedimentation, coagulation, flocculation, and decantation. Each possibility represents a separate embodiment.
  • the recovery by filtration e.g., microfiltration and/or nanofiltration
  • the obtained intermediate products are separated from the remaining liquid and may be washed with an aqueous solution or with an organic solvent such as ethanol or acetone and purified prior to being reused in the process.
  • concentration of liquid intermediate products such as the acid and base obtained following electrodialysis to desirable acid and base concentrations. It is to be understood that any one of the residues or by-products that are recovered and reused according to the principles of the present invention may be further purified by e.g., distillation, solid-liquid separation, crystallization, and the like, prior to being reused.
  • the MgSCU solution of Example 1 is subjected to an ion swap by the addition of NaOH.
  • MgSCU is mixed with water to a 50% w/w slurry, and the mixture is heated to about 40°C. 2 molar equivalents of NaOH 10M solution are added dropwise, resulting in precipitation of Mg(OH)2 as a white solid.
  • the precipitated solid is separated via filtration or centrifugation and washed with water.
  • the Mg(OH)2 is recycled and reused as a base in subsequent lactic acid fermentation.
  • the solution containing Na 2 SO 4 is subjected to electrodialysis as described in Example 6.
  • a sodium lactate solution is subjected to an ion swap by the addition of magnesium sulfate.
  • the precipitated solid is separated via filtration or centrifugation and washed with water to typically afford crude MgLa2'2H2O which is subjected to acidulation as described in Example 1 and the magnesium sulfate obtained as a byproduct of acidulation is recycled and reused in a subsequent sodium to magnesium swap reaction.
  • the solution containing Na 2 SO 4 is subjected to electrodialysis as described in Example 6.
  • Example 4 Monovalent to divalent cation exchange - magnesium lactate
  • Magnesium lactate was subjected to an ion swap to sodium lactate by mixing with a sodium hydroxide base.
  • 100g of NaOH 40% were added to a 0.5L reactor equipped with temperature and pH probes, heated to 90°C and stirred at 300 RPM.
  • 20% MgLa2 slurry was added using a peristaltic pump at 12 RPM, over the course of about Ih.
  • the reaction medium solidified completely.
  • the stirring was increased to 600 RPM to mechanically break the solid.
  • a total of 450g of MgLa2 were added.
  • the solution was centrifuged at 12,000g for 5 min to separate the precipitated MgOH2 from the sodium lactate solution.
  • the Mg(0H)2 precipitate was washed with 2 weight equivalents of DW and the wash was combined with the filtrate. NaOH residues were neutralized with lactic acid. Lactate recovery yield: 97%. Magnesium recovery yield: 98%.
  • sodium lactate solution obtained as described in Example 4 is heated to 60°C and stirred at 300 RPM. 1 molar equivalent of H2SO496% is added using a dropping funnel over the course of 1 hour. After the addition, the acidulate is stirred for 1 hour under the same conditions, then cooled to 25 °C. 1 weight equivalent of acetone at 20°C is added to the reactor, followed by immediate precipitation of Na 2 SO 4 . The mixture is stirred vigorously for 2 hours, followed by a vacuum filtration using a P3 sintered glass funnel, removing the Na 2 SO 4 .
  • the Na 2 SO 4 cake is washed with additional 0.3 weight equivalents of acetone and subjected to electrodialysis as described in Example 6.
  • the wash containing the lactic acid is combined with the original filtrate followed by the evaporation of the acetone and recovery using a rotary evaporator at 40°C and 150 mbar.
  • Electro-electrodialysis process is performed on the Na 2 SO 4 solution of Examples 2, 3, or 5 to simultaneously produce H2SO4 and NaOH.
  • a cell containing three chambers including an acid chamber, a feed chamber, and a base chamber is used ( Figure 5).
  • the solution containing the Na 2 SO 4 is fed to the feed chamber at an initial volume of 300mL- 800mL.
  • the flow rate is 40-80dm 3 /h.
  • Electrodialysis is performed at initial concentrations of Na 2 SO 4 of 50-200g/L.
  • the H2SO4 produced at the acid chamber is recycled back to acidify the lactate salt (Example 1) and the NaOH is recycled back to the ion swap (Example 2) or to the formation of a sodium lactate solution (Example 3).
  • the H2SO4 produced at the acid chamber is recycled back to acidify the lactate salt (Example 4) and the NaOH is recycled back to the ion swap (Example 5) or to the subsequent formation of a sodium lactate solution (without swap).

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Abstract

L'invention concerne des procédés économiques et écologiques pour la préparation d'acide lactique. Les procédés produisent de l'acide lactique avec récupération et réutilisation simultanées de résidus formés dans les procédés, étant ainsi essentiellement exempts de sous-produits indésirables.
PCT/IL2024/050421 2023-05-03 2024-05-02 Procédés de production d'acide lactique avec récupération et réutilisation simultanées de ses sous-produits Ceased WO2024228199A1 (fr)

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB173479A (en) * 1920-12-27 1922-11-09 Joseph Schatzkes Improved process of purifying lactic acid
WO2000017378A2 (fr) * 1998-09-17 2000-03-30 Imi (Tami) Procede de preparation de l'acide lactique
WO2005123647A1 (fr) * 2004-06-17 2005-12-29 Purac Biochem B.V. Procede pour la preparation d'acide lactique ou de lactate a partir d'un milieu contenant du lactate de magnesie
WO2011095631A1 (fr) * 2010-02-08 2011-08-11 Purac Biochem Bv Procédé de fabrication d'acide lactique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB173479A (en) * 1920-12-27 1922-11-09 Joseph Schatzkes Improved process of purifying lactic acid
WO2000017378A2 (fr) * 1998-09-17 2000-03-30 Imi (Tami) Procede de preparation de l'acide lactique
WO2005123647A1 (fr) * 2004-06-17 2005-12-29 Purac Biochem B.V. Procede pour la preparation d'acide lactique ou de lactate a partir d'un milieu contenant du lactate de magnesie
WO2011095631A1 (fr) * 2010-02-08 2011-08-11 Purac Biochem Bv Procédé de fabrication d'acide lactique

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