EP4071226A1 - Verfahren zur herstellung von fettsäurealkylestern - Google Patents

Verfahren zur herstellung von fettsäurealkylestern Download PDF

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Publication number
EP4071226A1
EP4071226A1 EP21167432.0A EP21167432A EP4071226A1 EP 4071226 A1 EP4071226 A1 EP 4071226A1 EP 21167432 A EP21167432 A EP 21167432A EP 4071226 A1 EP4071226 A1 EP 4071226A1
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EP
European Patent Office
Prior art keywords
phase
light phase
separated
free fatty
fatty acids
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EP21167432.0A
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English (en)
French (fr)
Inventor
Michael SIRCH
Lukasz Surma
Moritz Gaede
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At Agrar Technik Int GmbH
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At Agrar Technik Int GmbH
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Priority to EP21167432.0A priority Critical patent/EP4071226A1/de
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B3/00—Refining fats or fatty oils
    • C11B3/02—Refining fats or fatty oils by chemical reaction
    • C11B3/06—Refining fats or fatty oils by chemical reaction with bases

Definitions

  • the present invention relates to a process for producing fatty acid alkyl esters.
  • Fatty acid alkyl esters are widely used in the chemical and pharmaceutical industries both as raw materials and as intermediates. In addition, such compounds are also used in the food industry and, more recently, as diesel fuel (biodiesel).
  • unrefined oils often contain considerable amounts of free fatty acids, the presence of which negatively impact the transesterification reaction.
  • the free fatty acids react with the basic transesterification catalyst, thereby neutralizing the catalyst, which is then no longer available for the transesterification reaction.
  • the oils and/or fats are first treated with a non-miscible basic glycerol phase so that the free fatty acids are neutralized and pass into the glycerol phase, and then the triglycerides, after separation from the glycerol phase, are transesterified with monohydric alcohols using a base as catalyst in a stirred vessel to give the fatty acid esters. Further, the basic glycerol phase resulting from the transesterification of the triglycerides is used, after separation of the fatty acid esters, for the treatment of the oils and/or fats to remove the free fatty acids.
  • a problem to be solved by the present invention was thus the provision of an improved process for the production of fatty acid alkyl esters.
  • it was an object to render the process more suitable to accept unrefined oils and fats with varying amounts of free fatty acids and / or to increase the economy, while at the same time keep the complexity of the process low.
  • the present invention is based on the innovation of the inventors that a crude feedstock can be fed to different process steps. Thereby, it is possible to process with the same process different crude feedstocks, in particular crude feedstocks having relatively low as well as rather high amounts of free fatty acids as further explained herein. In comparison to the process of EP 1 183 225 B1 , where only feedstocks can be economically processed that do not contain too much free fatty acids (otherwise more than catalytic amounts of catalyst would be necessary), it is possible to directly use feedstocks with higher free fatty acid contents.
  • a crude feedstock of any origin can be generally processed as starting material as long as the crude feedstock contains triglycerides.
  • the benefits of the invention will be achieved only when the crude feedstock also contains free fatty acids, usually as unwanted by-products. Examples include: rapeseed oil, soybean oil, sunflower oil, tallow, palm oil and palm fat, olive oil, peanut oil, safflower oil, linseed oil, pure nut oil, cottonseed oil, rice oil, pork fat.
  • the process according to the invention is suitable for a large number of crude feedstocks of varying quality
  • the palette ranges from vegetable oils of edible oil quality to unrefined oils to animal fats or fat wastes, such as used hydraulic oils based on fat, and used edible oils, waste food fats, animal fats category I, II and III, trap grease from waste water treatment, POME (Palm oil mill effluent) and further side strains from the oleochemical industry.
  • Preferred crude feedstocks are selected from the group consisting of animal or vegetable fats and oils, in particular as they are traditionally used for the production of fatty acid esters.
  • Rapeseed oil, soybean oil and tallow are particularly suitable as crude feedstock, whereby the transesterification produces rapeseed oil fatty acid methyl ester, soybean fatty acid methyl ester and tallow fatty acid methyl ester if methanol is used as the alcohol.
  • waste oil and / or waste fat such as used cooking oil and / or deep-frying fat or used hydraulic oils based on fat, is / are used as crude feedstock.
  • the crude feedstock is fed to the neutralization reaction in step a) and / or to the esterification reaction in step c), depending on the amount of free fatty acids contained in the crude feedstock.
  • the free fatty acid content should not be too high, when the crude feedstock is fed to the neutralization reaction.
  • the crude feedstock is fed to the neutralization reaction in step a), if the crude feedstock contains free fatty acids in an amount of 8.0 wt.-% or less, preferably 7.5 wt.-% or less, more preferably 7.0 wt.-% or less, yet more preferably 6.5 wt.-% or less, most preferably 6.0 wt.-% or less, relative to the total weight of the crude feedstock, and /or if the crude feedstock contains free fatty acids in an amount 0.2 wt.-% or more, preferably 0.4 wt.-% or more, more preferably 0.6 wt.-% or more, yet more preferably 0.8 wt.-% or more, most preferably 1.0 wt.-% or more, relative to the total weight of the crude feedstock.
  • the crude feedstock is preferably fed to the esterification reaction. Accordingly, a process is preferred, wherein the crude feedstock is fed to the esterification reaction in step c), if the crude feedstock contains free fatty acids in an amount of 10 wt.-% or more, preferably 15 wt.-% or more, more preferably 20 wt.-% or more, yet more preferably 25 wt.-% or more, most preferably 30 wt.-% or more, relative to the total weight of the crude feedstock.
  • Fig. 1 the processes for producing fatty acid alkyl esters by catalytic transesterification of triglycerides from an oil and / or fat based crude feedstock containing triglycerides and free fatty acids of the invention as well as further embodiments thereof will be described below.
  • the process comprises the step:
  • the mixture 13 used in step a) comprises oil and / or fat as well as free fatty acids and triglycerides primarily originating from the crude feedstock, which may be directly fed to the neutralization reaction 10 of step a) and / or indirectly fed to the neutralization reaction 10 of step a) via the esterification reaction 30 in step c) and recycling 60 the separated third light phase 36 to the neutralization reaction of step a).
  • the neutralizing reaction preferably comprises mixing the mixture 13 with the alkaline glycerine phase. Mixing may be carried out in a first stirred tank reactor 12. Thereby, free fatty acids and residual water, if present, are largely extracted into the glycerine phase.
  • a preferred embodiment pertains to a process as described herein, wherein the neutralization 10 in step a) comprises mixing for less than 1 minute, preferably less than 55 seconds, more preferably less than 50 seconds and most preferably less than 45 seconds and/or wherein step a) comprises mixing for at least 10 seconds, preferably at least 15 seconds, more preferably at least 20 seconds, even more preferably at least 25 second and most preferably at least 30 seconds.
  • step a) comprises mixing for at least 10 seconds, preferably at least 15 seconds, more preferably at least 20 seconds, even more preferably at least 25 second and most preferably at least 30 seconds.
  • the reaction conditions during neutralization 10 are primarily limited by the solidification point of the components present in step a), in particular the oil and / or fat as well as free fatty acids and triglycerides originating from the crude feedstock. From an economic point of view, the neutralization 10 should be carried out at moderate temperatures, for instance at a temperature of 20 to 65 °C, preferably 25 to 60 °C, more preferably 30 to 55 °C. As the reaction preferably takes place in a pipe against a large vessel, e.g. a full vessel of 15 m height, the pressure preferably ranges between 0 and 3 bar.
  • the alkaline glycerine phase preferably contains enough free base to neutralize substantially all or the free fatty acids.
  • the base content may be 1 to 30 %, preferably 3 to 8 % (w/w).
  • the glycerine content can be 20 to 99 %, preferably 50 to 70 % (w/w).
  • the alkaline glycerine phase resulting from the transesterification reaction 40 of step e) is recycled to the neutralization reaction 10 in step a), as set forth further below.
  • the content of transesterification alcohol may be 5 to 40 % (w/w), preferably 15 to 25 % (w/w).
  • the amount of added alkaline glycerine phase, relative to the amount of added crude feedstock, may vary in a range of 1 to 100 % (w/w), preferably 5 to 20 % (w/w).
  • the alkaline glycerine phase can be supplemented by adding solid base or an alcohol/base mixture. It is possible to use any grade of glycerine, from technical to pharmaceutical grade as well as mixtures of different grades.
  • the base may be used with or without an alcohol. All base catalysts used for the transesterification reaction 40 of step e) can also be used as base in the neutralization reaction 10 in step a). Preferred bases / catalysts are described further below.
  • the mixture 13 is allowed to settle in order to allow the light phase and the heavy phase to separate from each other.
  • the mixture 13 can be transferred into a first settling tank 14.
  • Phase separation preferably occurs by sedimentation. Usual sedimentation times are 1 to 72 h, preferably 5 to 10 h.
  • the sedimentation temperature is preferably between 0 to 100 °C, preferably 45 to 60 °C, more preferably 47 to 55 °C. The skilled person will further appreciate that the temperature is limited by the solidification point of the components contained in the mixture / crude feedstock.
  • the temperature should be at least 30 °C, in the case of animal body and deep-fryer fats, the temperature should be 40 to 50 °C.
  • Phase separation results in formation of the first light phase 16 and the first heavy phase 18.
  • triglycerides are enriched. It may further contain up to 0.5 %, preferably up to 0.2 %, more preferably up to 0.1 % (w/w) free fatty acids, relative to the total weight of the first light phase 16.
  • neutralized free fatty acids also referred to herein as soaps or fatty acid salts
  • It further contains glycerine and optionally one or more of water and alcohol.
  • the process further comprises the step: b) separating the first light phase 16 and the first heavy phase 18 from each other, and acidifying 20 the separated first heavy phase 18.
  • the separated first heavy phase 18 may be transferred in a second stirred tank reactor 22 (alternatively, a static mixer can be used) and mixed with an acidic solution.
  • the pH value is preferably decreased to 1 to 4, preferably 2 to 3.
  • other side streams like washing water (from washing step h), methanol containing condensate (from esterification 30 and or from drying step g) etc. also may be added.
  • a glycerine-rich phase 18 is obtained as a by-product. This phase also contains soaps.
  • the glycerine phase is treated with an acid. This treatment releases the fatty acids from the soaps.
  • the released fatty acids and the fatty acid esters themselves are not miscible with glycerin and therefore separate from the glycerin phase as a separate phase.
  • the reaction mixture 23 is allowed to settle in order to allow the light phase and the heavy phase to separate from each other.
  • the mixture 23 can be transferred into a second settling tank 24.
  • Phase separation preferably occurs by sedimentation. Usual sedimentation times are 1 to 48 h, preferably 3 to 8 h.
  • the sedimentation temperature is preferably between 0 to 100 °C, preferably 45 to 60 °C, more preferably 47 to 55 °C.
  • Phase separation results in formation of the second light phase 26 and the second heavy phase 28. In the second light phase 26 free fatty acids are enriched, whereas the second heavy phase 28 is rich in glycerine. Further components of the second heavy phase 28 include water and alcohol.
  • the process further comprises the step: c) separating the second light phase 26 and the second heavy phase 28 from each other, and esterifying 30 free fatty acids in the separated second light phase 26 in the presence of an alcohol to enrich fatty acid esters in a third light phase 36 and the alcohol in a third heavy phase 38.
  • the esterification 30 allows both reacting the free fatty acids present in the processed feedstock having a relatively high free fatty acid content, e.g., above 10 %, to form fatty acid esters, and recovering the fatty acid compounds from all streams that were added to the reaction mixture 23.
  • the esterification 30 can be carried out by known processes.
  • An esterification 30 in the presence of an acid catalyst is preferred.
  • the separated second light phase 26 is mixed with the alcohol and the acid catalyst, for instance in a third stirred tank reactor 32.
  • the acid catalyst is not particularly limited and can, for example, be selected from the group consisting of sulfuric acid, paratoluenesulfonic acid, ion exchangers in H + form and methanesulfonoic acid . Sulfuric acid or methanesulfonic acid is particularly preferred.
  • the alcohol added in step c) is preferably a linear, branched or cyclic alkyl alcohol with 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms. Examples include: methanol, ethanol, propanol, i-propanol, butanol, sec-butanol, pentanol, hexanol, heptanol and octanol. It is further preferred that the alcohol has 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms. Most preferably, the alcohol is methanol, ethanol and / or propanol; methanol is particularly preferred.
  • the alcohol added in step e) is preferably independently selected from the aforementioned alcohols. The same or a different alcohol may be used. Preferably, the same alcohol is used in steps c) and e).
  • the esterification reaction 30 it is possible to add to the esterification reaction 30 a crude feedstock, which has a relative high content of free fatty acids.
  • the total amount of free fatty acids, which will undergo esterification 30, is the sum of the free fatty acids present in the separated second light phase 26 and the free fatty acids present in the crude feedstock.
  • the esterification reaction may take place at about 40 to 160 °C, preferably 50 to 140 °C, more preferably 60 to 75°C and / or at a pH value of 0 to 1.
  • the pressure preferably ranges between 900 to 1200 mbar, whereas at 160°C the pressure can be up to or even more than 4 bar.
  • the reaction may be allowed to proceed for 1 to 8 hours, preferably 4 to 6 hours and / or until the desired content decrease of free fatty acids has been achieved. It is further preferred that the reaction proceeds under mixing e.g. stirring.
  • the separated second heavy phase 28 can be further processed.
  • the second heavy phase 28 includes an alcohol, it may be separated from the glycerine-rich phase.
  • a convenient way of separation is by means of thermal separation, in particular rectification.
  • the separated alcohol may further be recovered and / or recycled to the esterification reaction 30 in step c) and / or to the transesterification reaction 40 in step e).
  • the reaction mixture 33 is allowed to settle in order to allow the light phase and the heavy phase to separate from each other.
  • the reaction mixture 33 can be transferred into a third settling tank 34.
  • Phase separation preferably occurs by sedimentation. Usual sedimentation times are 1 to 72 h, preferably 5 - 10 h.
  • the sedimentation temperature is preferably between 0 to 100 °C, preferably 30 to 60 °C, more preferably 40 to 50 °C.
  • Phase separation results in formation of the third light phase 36 and the third heavy phase 38.
  • fatty acid esters are enriched. It may further contain up to about 5 % (w/w), preferably up to about 2 % (w/w), free fatty acids.
  • the alcohol is enriched. It may further contain the acid catalyst and water.
  • step d) the third light phase 36 and the third heavy phase 38 are separated and the separated third light phase 36 is recycled 60 to the neutralization reaction 10 of step a). Due to the recycling step 60, it is possible to add the crude feedstock to the esterification reaction 30 in step c) and, thus, to process crude feedstocks with an increased free fatty acid content.
  • fatty acid alkyl esters are formed by catalytic transesterification 40 of the triglycerides contained in the separated first light phase 16.
  • Transesterification is to be understood as an alcoholysis of triglycerides, that is to say a reaction with alcohols, preferably alkyl alcohols, in particular methanol and ethanol, whereby monoesters of fatty acids and glycerol are formed via di- and monoglycerides as intermediates.
  • the fatty acids are not miscible with glycerin and therefore separate from the glycerin phase as a separate phase.
  • the process comprises the step: f) recycling 50 the separated third heavy phase 38 to the acidification 20 in step b).
  • the separated third light phase 36 is not recycled to step e).
  • the separated third light phase is not recycled to steps e) and b). More preferably, the separated third light phase is only recycled to the neutralization reaction of step a).
  • the advantages achieved by this embodiment include the possibility to save the fatty acid esters contained in the separated third light phase 36, and to further reduce the fatty acid content in order to not waste transesterification catalyst by neutralization.
  • the catalyst used in step e) is selected from the group of alkaline catalysts.
  • the catalyst is selected from the group of metal hydroxides, metal alcoholates and combinations thereof.
  • the metals used in this group are preferably selected from the first to third main groups of the periodic system.
  • the catalyst is selected from the group of sodium hydroxide, potassium hydroxide, sodium alcoholates, potassium alcoholates, such as sodium methylate, sodium ethylate, sodium butylate, potassium methylate, potassium ethylate, potassium butylate, and combinations thereof.
  • Most preferred is a process, wherein the catalyst comprises or is potassium methylate.
  • the advantages associated with potassium methylate include lower reaction temperatures, less side reactions and a higher solubility of K-soaps in glycerine.
  • step e) comprises:
  • the triglycerides contained in the separated first light phase 16 is mixed with a base as transesterification catalyst and an alkyl alcohol to carry out transesterification 40 of the triglycerides to fatty acid alkyl esters.
  • the required components may be added to and mixed in a fourth stirred tank reactor 42.
  • the total amount of alkyl alcohol used for the transesterification reaction 40 may be distributed among several transesterification stages, for instance 1 to 5 stages, preferably 2 stages. In total, about 1.05 to 2 mol, preferably 1.2 to 1.4 mol, alkyl alcohol per mol of bound fatty acid function may be used in this step. In a two-stage process (as further described below), 40 to 99%, preferably 90 to 95%, are used in the first stage and 0 to 60%, preferably 0 to 10%, in the second stage.
  • alkyl alcohol that can be employed in step e) is not limited. However, linear, branched or cyclic alkyl alcohols with 1 to 10 carbon atoms, in particular 1 to 4 carbon atoms, are preferred; methanol is particularly preferred.
  • the base can be dissolved in alcohol and added as an alcoholic solution.
  • the total amount of base (transesterification catalyst) added in this process step depends, on one hand, on the further process steps (e.g. the further transesterification stages) and, on the other hand, on the nature (i.e. composition) of the crude feedstock.
  • the total amount of base is used in this single stage, whereas in the case of a two-stage transesterification, only 20 to 95%, and preferably 80 to 90%, of the total quantity is used in the first stage.
  • the minimum amount of base at low free fatty acid content is primarily determined by the transesterification reaction 40.
  • the amount of free fatty acids to be neutralized primarily determines the required catalyst amount.
  • the required amounts can be routinely determined by a person skilled in the art, for example by the method disclosed in EP 1 183 225 B1 .
  • 0,088 mol base / 1000 g oil ensures an acceptable reaction rate.
  • 0,084 mol base / 1000 g oil is available for the neutralization reaction 10 of free fatty acids.
  • the transesterification 40 is performed at 40 to 65°C, preferably 45 to 60°C, more preferably 50 to 55°C and/or the transesterification 40 is performed for 10 to 100 min, preferably 30 to 80 min, more preferably 35 to 60°C, most preferably 40 to 50 min.
  • the reaction mixture 43 can be worked up in a suitable manner, whereas phase separation has proven to be particularly advantageous.
  • the obtained reaction mixture 43 may be fed into a fourth settling tank 44.
  • the reaction mixture 43 is allowed to settle in order to allow the light phase and the heavy phase to separate from each other.
  • Phase separation preferably occurs by sedimentation. Usual sedimentation times are 1 to 72 h, preferably 5 to 10 h.
  • the sedimentation temperature is preferably between 0 to 100 °C, preferably 45 to 60 °C, more preferably 47 to 55 °C.
  • Phase separation results in formation of the fourth light phase 46 and the fourth heavy phase 48.
  • fatty acid alkyl esters are enriched.
  • the fourth heavy phase 48 is rich in glycerine. It may further contain the base catalyst and the transesterification alcohol.
  • a fourth light phase 46 rich in fatty acid alkyl esters can be withdrawn.
  • the fourth light phase 46 is further processed by conventional methods or subjected to a second transesterification stage.
  • step e-2) further comprises:
  • a further (second) transesterification stage is particularly advantageous, if the first light phase 16 contains a relatively high amount of mono-, di- and/or triglycerides and a single transesterification stage is expected to be not sufficient to achieve the desired degree of conversion into fatty acid alkyl esters.
  • the separated fourth light phase 46 can be transferred to a fifth stirred tank reactor in which a second transesterification stage is carried out.
  • the second transesterification stage can be performed under the same reaction conditions as the first transesterification stage.
  • alkyl alcohol and base should be added to the second transesterification stage.
  • the alkyl alcohol and / or base may be added directly to the fifth stirred tank reactor and / or may be first mixed with each other and then fed into the fifth stirred tank reactor.
  • the base catalyst the same substance can be conveniently used as in the first transesterification stage. In terms of handling, an alcoholic solution containing 25 to 50 % (w/w) base is preferred.
  • the further (second) transesterification in step e-3 comprises mixing for at least 1 minute, preferably for at least 2 minutes, more preferably at least 3 minutes, even more preferably at least 4 minutes and most preferably at least 5 minutes and/or mixing less than 15 minutes, preferably less than 14 minutes, more preferably less than 13 minutes, even more preferably less than 12 minutes, even more preferably less than 11 minutes and most preferably less than 10 minutes.
  • reaction mixture obtained after the second transesterification stage can be worked up, whereby a phase separation carried out in the manner described above has proved advantageous.
  • the process may further comprise step h) washing the fourth light phase.
  • step h) washing the fourth light phase After the final phase separation, one or more washing steps may be carried out, wherein the fourth light phase is washed with at least 5 % (w/w) water, relative to the weight of the light phase.
  • Low-boiling components may be removed from the light phase rich in fatty acid alkyl esters. Removal may be achieved by evaporation. For instance, the light phase may be heated to 90 to 140 °C by passing over a heated surface. Thereby, the low-boiling components are evaporated and can be removed.
  • the process further comprises the step: g) recycling 70 the separated fourth heavy phase 48, and / or the separated fifth heavy phase, if present, to the neutralization reaction 10 in step a).
  • the glycerine, alcohol and base catalyst can be reused.
  • the base catalyst coming from the transesterification 40 can thus be used for neutralizing free fatty acids in the neutralization reaction 10 of step a).
  • steps a), b), d) and e) are performed continuously. More preferably, steps a), b), d) and e) as well as step f), if present, are performed continuously. Most preferably, steps a), b), d) and e) as well as steps f) and g), if present, are performed continuously.
  • first, second, third, fourth and / or fifth settling tank(s) may be dimensioned larger than the respective first, second, third, fourth and / or fifth stirred tank reactor(s).
  • the advantage of an increased dimension is that the settling tank(s) can be used as a reservoir, which means that, on the one hand, the settling times can be longer than the time required for the respective reaction and, on the other hand, a continuous withdrawal of the separated phase(s) is possible.
  • the settling tanks should also be designed in such a way that the light phase and the heavy phase can be removed separately from each other through outlets that are located at suitable heights of the settling tanks. It has proved to be advantageous to feed the respective reaction mixture to the settling tanks close to the interface, and to remove the respective phases remote from the interface. In this way, the phase separation can be performed efficiently.
  • the process comprises the steps:
  • step(s) a), b), c) and / or d) are preferably carried out as specified above or in the claims. This does also apply to one, some or all components employed in step(s) a), b), c) and / or d).

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EP21167432.0A 2021-04-08 2021-04-08 Verfahren zur herstellung von fettsäurealkylestern Pending EP4071226A1 (de)

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EP21167432.0A EP4071226A1 (de) 2021-04-08 2021-04-08 Verfahren zur herstellung von fettsäurealkylestern

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2024223722A1 (en) 2023-04-27 2024-10-31 Novozymes A/S Fatty acid esterification pretreatment process

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AT397966B (de) 1993-01-25 1994-08-25 Wimmer Theodor Verfahren zur herstellung von fettsäureestern niederer einwertiger alkohole
EP1183225A1 (de) 1999-06-07 2002-03-06 AT Agrar-Technik GmbH Verfahren zur herstellung von fettsäureestern einwertiger alkylalkohole und deren verwendung
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