Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/47—Separation; Purification; Stabilisation; Use of additives by solid-liquid treatment; by chemisorption
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
  • C07C51/42—Separation; Purification; Stabilisation; Use of additives
  • C07C51/43—Separation; Purification; Stabilisation; Use of additives by change of the physical state, e.g. crystallisation
• • C—CHEMISTRY; METALLURGY
  • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
  • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
  • C12P7/00—Preparation of oxygen-containing organic compounds
  • C12P7/24—Preparation of oxygen-containing organic compounds containing a carbonyl group

Definitions

• Process for extracting ferulic acid and/or its salts comprising a step a) in which a biomass is extruded in the presence of a base
• the present invention refers to a process for extracting ferulic acid and/or its salts comprising a step (a) in which a biomass is extruded in the presence of a base.
• the present invention also refers to ferulic acid in protonated or salified form which can be obtained according to the process of the present invention.
• the present invention also refers to a process for the preparation of vanillin from ferulic acid obtained according to the process of the present invention.
• the invention finds applications in particular in the field of food, cosmetics and flavorings.
• Ferulic acid or 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid is a compound naturally present in plants and in particular cereals such as rice, corn, wheat or oats. It can also be present in solid or liquid co-products from the agri-food industry, in particular from the oilseed, cereal, sugar or alcohol sectors.
• Ferulic acid can be prepared by chemical synthesis, or by a biotechnological route involving microbial fermentation or plant tissue culture. It can also be obtained by a route qualified as natural and/or biosourced in which a plant material is treated in order to extract ferulic acid from said plant material. For example, it can be extracted from by-products of the food industry or from grains, for example according to the process described in WO2014/187784.
• Document WO 2001/067891 describes a process for preparing the separation of ferulic acid and arabinoxylans comprising an extrusion step followed by a step in which the extrudate is suspended in water in the presence of enzymes allowing the hydrolysis of cell walls. Table 1 also seems to indicate that an extrusion process alone does not allow the separation of ferulic acid from rice bran.
• Ferulic acid is used in various fields ranging from cosmetics to food, in particular in the preparation of a widely consumed flavoring substance, vanillin.
• Vanillin can be produced by chemical synthesis, however natural flavors are preferred over synthetic flavors by consumers. In order to satisfy current demand, particular interest has been shown in the preparation of non-synthetic vanillin. So, we have seen the growth of methods for the preparation of natural vanillin using natural and/or biosourced materials, these methods being able to be qualified as natural according to the legislation in force.
• natural vanilla can be obtained by a biotechnological process comprising in particular the culture of a microorganism capable of allowing the biotransformation of a fermentation substrate into vanillin.
• a biotechnological process is for example described in application EP0885968 in which a microorganism converts ferulic acid into vanillin.
• the natural vanillin thus obtained generally undergoes extraction and/or purification steps.
• vanillin can be purified according to the methods described in applications WO2014/114590, EP2791098 or WO2018/146210.
• Figure 1 presents a block diagram describing a first embodiment of the process for extracting ferulic acid and/or its salts according to the present invention.
• FIG 2 presents a block diagram describing a second embodiment of the method for extracting ferulic acid and/or its salts according to the present invention.
• Figure 3 represents the results obtained in example 8.
• Ferulic acid corresponds to the following formula:
• bio-based ferulic acid refers to ferulic acid entirely or significantly of vegetable or marine origin.
• bio-based ferulic acid can be derived from agricultural by-products, plants, seeds, forestry materials, or algae.
• biobased ferulic acid is of plant origin.
• biobased ferulic acid is not the result of chemical synthesis.
• the carbon-carbon double bond of the biobased ferulic acid is in the trans configuration.
• the present invention refers to a process for extracting ferulic acid and/or its salts comprising a step a) in which a biomass is extruded in the presence of a base.
• the biomass is subjected to reactive extrusion.
• Step a) allows the preparation of a raw extrudate (EB) and optionally a filtrate (F).
• the quantity of raw extrudate (EB) is equal to the sum of the masses of the raw materials entering in step a), for example in a particular embodiment the quantity of raw extrudate (EB) can be equal to the mass of the starting biomass added to the basic mass used.
• the biomass can be chosen from the group consisting of plants, seeds, forest materials, algae or agricultural by-products.
• the biomass can be chosen from the group consisting of vegetable fibers or vegetable bran, in particular chosen from the group consisting of fibers or oat bran, barley, wheat, rice or corn.
• the ferulic acid content in the biomass to be treated is between 0.3% by weight and 5% by weight, preferably between 0.5 and 5% by weight.
• the ferulic acid content is expressed by weight relative to the weight of the dry biomass.
• Step a) is an extrusion step, in particular extractive extrusion or reactive extrusion.
• the extrusion can be carried out in a co-rotating twin-screw extruder.
• the co-rotating twin-screw extruder can be from the Evolum range from Clextral or Leistritz ZSE.
• THE screw profile can comprise at least one conveying zone, at least one mixing zone and optionally counter-threads.
• step a) is carried out at a temperature less than or equal to 120°C, preferably less than or equal to 110°C, and very preferably less than or equal to 100°C.
• step a) is carried out at a temperature greater than or equal to room temperature, preferably greater than or equal to 30°C, very preferably greater than or equal to 50°C.
• step a) can be carried out at a temperature of between 60°C and 80°C.
• ambient temperature refers to a temperature between 15°C and 25°C.
• the speed of rotation of the screws of the extruder is not particularly limited in order to allow a good separation of the ferulic acid contained in the biomass.
• Extruder rotational speed refers to the rotational speed of the extruder screws.
• step a) can be carried out with an extruder rotation speed of between 100 rpm and 1200 rpm.
• step a) is carried out with a speed of rotation of the extruder of between 150 revolutions/min and 400 revolutions/min, for example at 200 revolutions/min.
• step a) is carried out in the presence of a base.
• the biomass is subjected to an extraction of the ferulic acid and/or its salts using a base simultaneously with the extrusion.
• the biomass used in the context of the present invention can be wet or dry.
• the biomass is a wet biomass, preferably the dry matter content is between 35 and 50% by weight, preferably between 38 and 45% by weight.
• the biomass is a dry biomass, preferably the dry matter content is between 80 and 95% by weight, preferably between 84 and 92% by weight.
• the base can be chosen from strong bases, in particular chosen from the group consisting of NaOH, KOH.
• the base is chosen from NaOH, KOH, CaO, Ca(OH)2 or inorganic carbonates.
• the base can be added in solid form or in the form of a solution, preferably an aqueous solution.
• the concentration of the base is between 0.5N and 5N, preferably between 1N and 4N, very preferably between 2N and 3N.
• the biomass is generally used in wet form.
• the humidity contained in the biomass makes it possible to solubilize the base used.
• the biomass and the base are added separately in the extruder.
• a water flow can also be added in the extruder.
• the mass ratio between the biomass and the base is between 10% and 90%, preferably between 25% and 75%, even more preferably between 30% and 60%.
• step (a) can be carried out with a mass ratio between the biomass and the aqueous solution of 50%.
• the mass ratio (kg/kg) between the amount of base used and the amount of biomass relative to the dry biomass is between 0.05 and 0.50, preferably between 0.05 and 0.30, very preferably between 0.09 and 0.20.
• the quantity of base used refers to the mass of the base used directly in solid form, or to the mass of solid base present in the base solution used in step a).
• these values can be adjusted according to the biomass used, or its moisture content in particular.
• the yield of ferulic acid and/or its salts during step a) is quantitative.
• the reactive extrusion of step a) generally allows the complete release of the ferulic acid contained in the biomass or of substantially all the ferulic acid contained in the biomass.
• the yield of ferulic acid and/or its salts during step a) is greater than or equal to 50%, preferably greater than or equal to 60%.
• step a) is carried out in the absence of hydrolysis enzyme such as cellulases or hemicellulases.
• the base used in step a) is substituted by at least one enzyme promoting the extraction of ferulic acid and/or its salts from the biomass.
• the combination of extrusion with the extraction of ferulic acid and/or its salts in the presence of a base allows in a single unit operation the hydrolysis of the cell walls and the release in the salified form of ferulic acid.
• the process of the present invention makes it possible in particular to reduce the size of the reactor used, also makes it possible to intensify the process, that is to say that a greater quantity of biomass can be treated in a certain volume of reactor compared to to known methods or that a greater quantity of biomass can be processed in a certain time compared to known methods, the residence time of the biomass in the extruder being shorter.
• the environmental impact of the process of the present invention is improved, in particular in that the consumption of water and/or energy is reduced while maintaining a good yield of extraction of ferulic acid.
• the raw extrudate (EB) can be subjected to at least one washing step b).
• step b) is carried out by adding a solvent, preferably chosen from water, alcohols or a mixture thereof.
• the addition of solvent is carried out in such a way as to put the extrudate in suspension.
• the water is distilled or demineralised water.
• the alcohol is generally chosen from alcohols comprising between 1 and 6 carbon atoms, such as methanol, ethanol, isopropanol, preferably ethanol.
• the use of ethanol makes it possible to improve the solid/liquid separation, the ferulic acid and/or its salts is indeed preferably recovered in the liquid phase.
• the use of ethanol also improves the recovery of fibers in the solid phase and/or the reduction of the quantity of dry matter in the liquid phase.
• the use of ethanol in the washing solvent improves the separation of polysaccharides, the polysaccharide content is reduced in the liquid phase.
• the solvent can also be a water/alcohol mixture, preferably the water/ethanol mass ratio is generally between 1:1 and 1:3.
• the solvent can also comprise an acid, preferably chosen from hydrochloric acid or sulfuric acid.
• Step b) is generally carried out at a temperature between 10°C and 80°C, preferably between 10°C and 50°C.
• step b) is generally carried out at a temperature between 10°C and 35°C.
• the solid and liquid phases of the suspension obtained during step b) are then separated to allow the preparation of a washed extrudate (EL) and a liquid solution (S).
• the pH of the liquid solution (S) is greater than or equal to 5.
• the pH of the solution (S) is preferably between 5 and 8, preferably between 5 and 6.
• the liquid solution (S) comprises ferulic acid in salified form, dissolved.
• the separation can be carried out by any process for separating a solid/liquid composition, such as in particular filtration, decantation, centrifugation, pressing (filter press, screw press), flotation.
• the centrifugation is carried out at a speed greater than or equal to 1000 revolutions/min, preferably less than or equal to 5000 revolutions/min.
• a liquid solution (S1) is isolated from a solid phase, the washed extrudate (EL).
• the solid phase obtained at the end of step b) (EL) can again be subjected to a step b) to obtain a second liquid solution (S2).
• This washing can be repeated several times.
• the subsequent washes can be carried out by adding a solvent as described above, in particular a solvent chosen from water, alcohols or mixtures thereof.
• subsequent washes can be performed by recycling of the liquid solutions obtained at the end of step c) of a process according to the present invention.
• liquid solutions (Si) (in which i represents the number of washes carried out) are combined to form a liquid solution (S).
• the total wash ratio is between 1 and 5, preferably between 1 and 4, very preferably between 1 and 3 and even more preferably between 1 and 2.5.
• the total wash ratio is defined as the ratio of the total amount of liquid used in step (b) to the amount of raw extrudate (EB) as previously defined.
• the concentration of ferulic acid or its salts in the liquid solution (S) is between 0.1 g.L-1 and 30 g.L-1, preferably between 0.5 g.L-1 and 15 g.L-1.
• the washed extrudate can be recovered, in particular in methanization, animal nutrition, or human food.
• the amount of dry matter present in the washed extrudate is less than or equal to 70%, preferably less than or equal to 60%, 50%, 40%, 30%, 20%, 10%.
• the amount of dry matter represents the amount of solid (usually fibers) remaining after complete drying of the washed extrudate.
• the quantity of dry matter present in the liquid solution (S) is less than or equal to 20%, preferably less than or equal to 10%, very preferably less than or equal to 5%.
• step a) of extrusion and step b) of washing can be carried out simultaneously allowing the preparation of a washed extrudate and of a filtrate (F).
• steps a) and b) are carried out "simultaneously" refers to a case in which all of these steps are carried out in at least one extruder, for example two consecutive extruders.
• the extrusion and washing steps are consecutive.
• this combination can in particular be produced in the presence of an extruder and at least one filter sleeve.
• the washing can be carried out against the current.
• the ferulic acid concentration in the filtrate (F) is between 0.1 g.L-1 and 10 g.L-1.
• the washed extrudate can be recovered, in particular in methanization, animal nutrition, or human food.
• the amount of dry matter present in the washed extrudate is less than or equal to 70%, preferably less than or equal to 60%, 50%, 40%, 30%, 20%, 10%.
• the amount of dry matter represents the amount of solid (usually fibers) remaining after complete drying of the washed extrudate.
• the quantity of dry matter present in the filtrate (F) is less than or equal to 20%, preferably less than or equal to 10%, very preferably less than or equal to 5%.
• the process for extracting ferulic acid and/or its salts may comprise at least one step c) for purifying the filtrate (F) and/or the liquid solution (S).
• the purification may in particular comprise a step c1) of acidification of the filtrate (F) or of the liquid solution (S).
• Step c1) is optional.
• an acidified solution is recovered in which the ferulic acid is present in the protonated form.
• the acidification step is generally carried out by adding a strong acid, in particular chosen from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid.
• a strong acid in particular chosen from the group consisting of sulfuric acid, hydrochloric acid, phosphoric acid.
• the pH of the solution is between 2 and 5, preferably between 2.5 and 4.
• the acidification step allows the precipitation of fibers and acids fats contained in the filtrate (F) or in the liquid solution (S).
• a filtration step can be carried out at the end of the acidification step c1), this step makes it possible in particular to filter the salts obtained during the acidification.
• the filtration also makes it possible to at least partially retain the fatty acids.
• the filtrate (F) or the liquid solution (S) can be used directly.
• the pH of the filtrate (F) or the liquid solution (S) is greater than or equal to 5.
• the pH of the filtrate (F) or of the liquid solution (S) is generally between 10 and 13, preferably between 11 and 12.
• the pH of the filtrate (F) or of the solution (S) is preferably between 5 and 8, preferably between 5 and 6.
• the liquid solution (S) comprises ferulic acid in salified form, dissolved.
• the purification process may also comprise at least one step c2) of adsorption of ferulic acid and/or its salts.
• the adsorption can generally be carried out with a column filled with synthetic resin preferably chosen from the group consisting of Amberlite XAD-4, Amberlite XAD-16, PVDPP (polyvinyl polypyrrolidone), DVBS (divinylbenzene styrene), DVBPS (divinylbenzene polystyrene resins), preferably polyvinyl benzyl dimethyl amine, polyvinyl benzyl dimethyl amine.
• the adsorption step can be carried out on activated carbon.
• Step c2) can also be performed with Acticarbone BGX, Acticarbone BGE, Amberlite IRA-900, Ambersep 90OH, or Purolite MN502.
• a resin or an activated carbon containing ferulic acid and/or its salts and an aqueous solution having a ferulic acid content is obtained. and/or its reduced salts.
• the aqueous solution has a content of ferulic acid and/or its salts of less than or equal to 0.1 g/L.
• This aqueous solution can advantageously be recycled in the process for extracting ferulic acid and/or its salts according to the present invention.
• this aqueous solution can be used as washing solvent for step (b).
• step c2) allows the separation of the polysaccharides from the ferulic acid. Ferulic acid or its salts is adsorbed during the adsorption step.
• a stage c3) of desorption of the ferulic acid and/or its salts with a solvent is generally carried out.
• the desorption is carried out with a countercurrent flow.
• a solution rich in ferulic acid is obtained at the end of step c3).
• the solution rich in ferulic acid has a ferulic acid content of between 5 g.L-1 and 500 g.L-1.
• the solvent used during the desorption step is chosen from the group consisting of water (acid or base, with or without a complexing agent), cyclic and acyclic hydrocarbon solvents, alcohols, aromatic alcohols, aldehydes, ketones and esters, preferably the solvent is an alcohol and very preferably the alcohol is ethanol.
• the solvent used is water, this has an acid or basic pH, the water can also contain one or more complexing agents.
• complexing agent is meant a substance capable of generating a precipitate which is insoluble in the solvent of the liquid medium, in particular insoluble in water.
• the first complexing agent is a cation, in solution in a solvent, preferably in water or in a solvent mixture.
• the first complexing agent is advantageously in the form of a monovalent, divalent, trivalent, tetravalent or pentavalent cation salt solution, in particular a divalent or trivalent cation salt.
• the cation salt in particular divalent or trivalent, can be a sulphate, chloride, nitrate, carbonate, phosphate, hydroxide, acetate salt or a mixture thereof.
• the cation in particular divalent or trivalent, can be chosen from the group consisting of transition metals, metals, alkaline earths or rare earths, it being understood that the cation, when it is brought into contact with the medium of starting point, is capable of forming a precipitate which is insoluble in the solvent of the starting medium, in particular in water.
• the first complexing agent is a cation of a transition metal selected from the group consisting of iron, nickel, copper, titanium, zirconium or a mixture thereof, preferably selected from iron or copper.
• the first complexing agent is a metal cation chosen from the group consisting of aluminum and zinc.
• the first complexing agent is a cation of an alkaline earth chosen from the group consisting of calcium and magnesium.
• the first complexing agent is chosen from the group consisting of rare earths such as yttrium or lanthanides, or metal oxides such as Al203, Ti02, Si02 and/or ZnO.
• the purification process may comprise an optional step c4) of evaporation of the solvent to allow the production of ferulic acid purified (FAP).
• An optional acidification step may be required prior to evaporation to obtain ferulic acid in the protonated form.
• the FAP can be used directly, in particular in a process for the preparation of vanillin by fermentation.
• the resin or the activated carbon used in step c2) can be regenerated.
• the extraction process can also comprise a step in which the ferulic acid is crystallized or precipitated.
• crystallized or precipitated ferulic acid can be used directly, in particular in a process for the preparation of vanillin by fermentation.
• the purification process can be preceded by a preliminary step cO) to steps c1), c2) and/or c3) in which the alcohol or alcohol mixture, optionally used during the washing step b) is evaporated from the liquid solution (S) or from the filtrate (F).
• this preliminary step is carried out by evaporation, in particular by using a falling or scraped film evaporator.
• the amount of residual solvent is less than or equal to 2 % by weight, preferably less than or equal to 1% by weight, very preferably less than or equal to 0.5% and even more preferably less than or equal to 1000 ppm relative to the dry biomass.
• Another aspect of the present invention relates to a process for the preparation of vanillin by fermentation of ferulic acid and/or its salts obtained according to the extraction process of the present invention.
• the vanillin preparation process is carried out in the presence of a microorganism, for example as described in EP0885968 in particular in the presence of Amycolatopsis ATCC 39116.
• the ferulic acid or its salts which can be used for the preparation of vanillin can be FAP, FAC.
• the method of the present invention has improved properties such as:
• the biomass extracted at the end of the process according to the present invention can be reused in methanation, animal feed,
• the other constituents of the biomass are not degraded within the framework of the method of the present invention and the biomass extracted at the end of the method according to the present invention can be used to extract other constituents.
• the present invention also refers to ferulic acid in protonated or salified form which can be obtained according to the process of the present invention.
• the invention finds applications in particular in the field of food, cosmetics and flavorings.
• step a) Dissolution in water of the extrudate obtained in step a) (crude extrudate) in a perfectly stirred standard reactor (RPAS) with a dilution rate of 10 for 3 hours with stirring at room temperature.
• RPAS perfectly stirred standard reactor
• the wash ratio is 9.
• the solution is separated from the solid phase (washed extrudate) by centrifugal decantation at room temperature. Two streams are thus obtained: the solid with a dry matter content (DM) of 15% and a liquid solution (S) with a DM content of 3%.
• the ferulic acid extraction rate contained in the liquid solution (S) measured by HPLC is equivalent to at least 80% of the ferulic acid content present in corn bran.
• Step c1) Acidification/filtration of the solution
• the solution obtained is acidified by adding sulfuric acid to pH 2-3 in order to promote the subsequent adsorption of ferulic acid.
• the solution is clarified by cartridge filtration or centrifugation of the solution before proceeding to the adsorption step.
• the ferulic acid present in the acidified solution obtained in step c1) is adsorbed on a polystyrene divinylbenzene adsorbent resin of the XAD 16 type. The desorption is carried out with ethyl acetate.
• Crystallization is carried out to obtain ferulic acid with a purity greater than 80%.
• RPAS perfectly stirred standard reactor
• the solution is separated from the solid phase (washed extrudate) by centrifugation or spin-drying to obtain a washed extrudate and a liquid solution (S).
• the ferulic acid extraction rate contained in the liquid solution (S) measured by HPLC is equivalent to at least 70% of the ferulic acid content present in the bark of oats.
• the solution from step b) is separated from the washed extrudate by centrifugal decantation at room temperature. Two streams are thus obtained: the solid with a dry matter (DM) rate of 50% and the liquid solution (S) with a DM rate of 3-4%.
• the ferulic acid extraction rate contained in the liquid solution (S) measured by HPLC is equivalent to at least 80% of the ferulic acid content present in corn bran.
• RPAS perfectly stirred reactor
• the solution from step b) is separated by centrifugal decantation at room temperature. Two streams are thus obtained: the solid with a dry matter (DM) rate of 50% and the liquid solution (S) with a DM rate of 3-4%.
• the ferulic acid extraction rate contained in the liquid solution (S) measured by HPLC is equivalent to at least 80% of the ferulic acid content present in corn bran.
• Step c1) Acidification/filtration of the solution
• the solution obtained is acidified by adding sulfuric acid to pH 2-3 in order to promote the subsequent adsorption of ferulic acid.
• the solution is clarified by cartridge filtration or centrifugation of the solution before proceeding to the adsorption step.
• the ferulic acid present in the acidified solution obtained in step c1) is adsorbed on an adsorbent polystyrene divinylbenzene type XAD 16 resin.
• the desorption is carried out with acetate of ethyl.
• Crystallization is carried out to obtain ferulic acid with a purity greater than 80%.
• Example 6 Extraction of ferulic acid from corn gluten feed (CGF)
• the pH of the extracted fiber is 6, and can advantageously be used in animal feed.
• Example 7 Extraction of ferulic acid from corn fibers
• the pH of the extracted fiber is 6, and can advantageously be used in animal feed.
• Step b): Replumping of 150 kg of extrudate in aqueous ethanol solution Dissolving the extrudate obtained in step a) (crude extrudate) in a perfectly stirred reactor with a dilution rate of 6 (washing ratio 5 ) in an aqueous ethanolic solution having a water/ethanol mass ratio of 2:3 for 2 hours with stirring at room temperature.
• the solution from step b) is separated from the washed extrudate by centrifugal decantation at room temperature. Two flows are thus obtained: the solid (EL) with a dry matter content (DM) of 52% and the liquid solution (S) with a dry matter content of 1.5%.
• the extraction rate of ferulic acid contained in the liquid solution (S) measured by HPLC is 77% of the content of ferulic acid present in corn bran.
• the fiber yield obtained in the solid (E) is 94% of the initial biomass content introduced.
• the dairy fodder unit (UFL) is 1.05 on a dry basis.
• Sbis Extraction of ferulic acid from corn bran
• the pH of the solid (extracted fiber) is 12, and can advantageously be recovered directly in methanation.
• Example 11 Extraction of ferulic acid from corn bran Stage a) and b): The extrusion and washing conditions are grouped together in the table below.
• the average residence time is 50 seconds.
• the pH of the solid (extracted fiber) is 5-6, and can advantageously be recovered directly in methanization or directly in animal feed.
• Example 12 Extraction of ferulic acid from CGF Step a) and b): The extrusion and washing conditions are grouped together in the table below.
• the pH of the solid (extracted fiber) is 5-6, and can advantageously be used in animal feed or methanation.
• the pH of the solid (extracted fiber) is 5-6, and can advantageously be upgraded in methanation.

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• 2021
  • 2021-07-27 FR FR2108154A patent/FR3125818A1/fr not_active Withdrawn
• 2022
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