Method for determining parameters of a naturally occurring composition in order to determine the most suitable treatment for removing heteroatoms from said composition

Abstract

The present invention relates to a method for determining parameters representative of the quality of a composition of natural origin, which make it possible to determine the most suitable heteroatom removal treatment for processing said composition, in particular with hydroprocessing for the production of renewable fuels in mind.The present invention also relates to a method for reducing the heteroatom content of compositions of this type, in particular for the production of renewable fuels.

Description

[Technical field]

[0001] The present invention relates to a method for determining parameters representative of the quality of a composition of natural origin, which makes it possible to determine the most suitable treatment for the removal of heteroatoms for the treatment of the composition, in particular with a view to its treatment to produce renewable fuels, in particular renewable fuels of diesel fuel type and / or aviation fuel type, in particular SAF (Sustainable Aviation Fuel).The present invention also relates to a series of methods for the treatment of compositions of said type, in particular to produce renewable fuels. [Background technology]

[0002] A wide variety of renewable fuels are currently available, including biodiesel and fuels derived from the hydroprocessing of naturally occurring oils.

[0003] Biodiesel is currently produced by the transesterification of triglycerides with methanol to produce methyl esters and glycerol in the presence of homogeneous or heterogeneous basic catalysts. Triglycerides are obtained from naturally occurring oils.

[0004] Other renewable fuels are produced by hydrodeoxygenation of naturally occurring oils, usually followed by an isomerization step, which can improve the low temperature properties of the fuel, and optionally a fractionation step, the hydrodeoxygenation and isomerization steps also being carried out in the presence of a catalyst.

[0005] The naturally occurring oils typically used to produce renewable fuels are animal fats and oils, various seed oils, soybean oil, rapeseed oil, palm oil, seed oils collected after being used to cook food (commonly called used cooking oil (UCO)), or algae oils, or oils obtained from nut shells (especially cashew nut shell oil).

[0006] However, these oils and fats contain large amounts of contaminants (phospholipids, phosphates, gums, metals, sulfur, ash, water, pigments, and other undesirable materials) that can have adverse effects on downstream processing, such as catalyst deactivation, corrosion, and fouling, and therefore require pretreatment to remove all or part of these deleterious effects.

[0007] Therefore, before being converted into renewable fuels, naturally occurring fats and oils and UCOs are usually pre-treated by well-known chemical and physical methods similar to those carried out in the processing of edible oils, such as degumming, neutralization with alkaline (usually NaOH) or acidic solutions (e.g., citric acid), bleaching, finishing or polishing, steam treatment, etc.

[0008] US2019338219 describes a method for producing biodiesel that includes a pretreatment step before esterification. This pretreatment is selected depending on the fatty acid content of the feedstock. It can be chemical refining with the addition of a basic compound, centrifugation, bleaching and polishing, or degumming with the addition of a basic compound, centrifugation, bleaching and polishing, or bleaching and polishing only. The centrifugation step allows the removal of the aqueous phase, polar or hydratable compounds, and solids. The bleaching step (heating or addition of bleaching agents) allows the removal of solids, residual soap, moisture, and other impurities. The polishing step allows the removal of residual solids by filtration. Any fatty acids still remaining can be removed by stripping (or deacidification) or converted by esterification before the transesterification reaction. The biodiesel produced is then refined again by filtration.

[0009] A refining method that allows for a significant reduction in sulfur, metals and other impurities in renewable oil is also known from US Patent Application Publication No. 2019031964. First, the oil is mixed with an aqueous citric acid solution at 60 ° C, then centrifuged to remove gums, and finally treated with a mixture containing water, hydrotreated long-chain ester compounds and phosphoric acid derivatives at at least 100 ° C for 10 minutes, then the temperature is increased to 120-130 ° C for 30-90 minutes. The mixture is then cooled and centrifuged again. [Prior art documents] [Patent documents]

[0010] [Patent Document 1] US Patent Application Publication No. 2019338219 [Patent Document 2] US Patent Application Publication No. 2019031964 Summary of the Invention [Problem to be solved by the invention]

[0011] However, these well-known methods consume chemicals, generate waste products, and can be energy intensive, especially if heating is required. Furthermore, due to the complexity of oils, it is difficult to remove all gums, which is made even more difficult because in most cases mixtures of fats and oils of different origins are used and their relative proportions can vary significantly over time. Therefore, there is a need for flexible and robust methods to adequately remove phospholipids, nitrogen compounds, and metals from complex mixtures of fats and oils of different origins and varying composition.

[0012] However, the removal of phospholipids and nitrogen compounds by conventional pretreatment methods remains difficult and almost unpredictable, so currently only complex mixtures of fats and oils with a certain phosphorus content are accepted as input for these pretreatments, limiting the choice of usable raw materials. Thus, currently, the total phosphorus content of the processed mixtures is below a certain threshold. However, some of these raw materials are difficult to process even if their phosphorus content is below this threshold.

[0013] Thus, there is a need for more efficient and less costly processing of naturally occurring compositions that contain lipids and heteroatoms, particularly at least one heteroatom selected from nitrogen and phosphorus, which heteroatoms are usually in the form of organic compounds.

[0014] The applicant has surprisingly discovered that the total content of heteroatoms present in the compounds capable of hydration at neutral pH and the ratio of this total heteroatom content (especially when the heteroatom is phosphorus or nitrogen) makes it possible to characterize the quality of a naturally occurring composition comprising lipids (especially its suitability for efficient processing by a heteroatom removal treatment).

[0015] The object of the present invention is to propose a method for determining parameters representative of the quality of a composition of natural origin containing lipids, making it possible to determine the suitability of a process for removing heteroatoms in an efficient and cost-effective manner in order to reach a target content of heteroatoms or below a target value.

[0016] This parameter can be used to determine which heteroatom removal treatments can be applied to a composition of naturally occurring oils containing lipids in order to achieve a target content of heteroatoms (especially phosphorus and / or nitrogen).

[0017] This parameter can also be used in methods for reducing the heteroatom content of naturally occurring compositions, including lipids, particularly in methods for reducing the heteroatom content. [Means for solving the problem]

[0018] Method for determining parameters representative of the quality of a composition of natural origin A first object of the present invention relates to a method for determining a parameter representative of the quality of a composition of natural origin comprising heteroatoms and lipids, chosen from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters and / or mixtures of two or more of these compounds, comprising: (A) determining the total content of at least one heteroatom selected from phosphorus and nitrogen in the composition; (B) identifying said at least one heteroatom compound hydratable at neutral pH and determining the total content of said heteroatoms present in said identified heteroatom compound hydratable at neutral pH; (C) determining the ratio of the total content of said at least one type of heteroatom present in said compounds of said heteroatoms hydratable at a specified neutral pH to the total content of said heteroatoms in said composition as a parameter representative of the quality of the composition (this ratio being determined for phosphorus, nitrogen or each of these two types of heteroatoms).

[0019] In particular, step (B) may be carried out by an analytical technique selected from NMR, mass spectroscopy, ion chromatography, liquid chromatography coupled with mass spectrometry (LC-MS), high performance thin layer chromatography (HPTLC).

[0020] Rin 31 ( 31 P), or nitrogen 15 ( 15 N) NMR can be used.

[0021] The measurements carried out in step (A) can be carried out by elemental analysis, typically X-ray fluorescence (XRF) or ICP (in particular according to standard UOP 389), although other methods (NMR, HPTLC, etc.) can also be considered.

[0022] The total content may be a weight content (eg expressed in ppm) or a concentration (eg molar concentration, etc.).

[0023] The aforementioned analytical techniques are well known to those skilled in the art who know how to carry them out, in particular how to prepare samples, in order to identify compounds hydratable at neutral pH and to quantify the phosphorus and / or nitrogen present in this composition.

[0024] for example, 31 For P NMR, the sample is washed with a chelating agent (e.g., EDTA type) of appropriate pH (e.g., pH 7), then the organic and aqueous phases are separated and each phase is collected. 31 Carry out analysis by P NMR.

[0025] Typically, the nitrogen or phosphorus compounds hydratable at neutral pH that one wishes to identify and quantify the P and / or N content are compounds whose structure and potential presence are known, e.g. following a prior analysis of their composition.

[0026] [Naturally derived compositions] The naturally occurring composition used in the present invention is a composition comprising a heteroatom and a lipid selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters, and / or mixtures of two or more of these compounds.

[0027] The composition may comprise or consist of a naturally occurring oil or mixture of natural oils.

[0028] Naturally derived oils are defined as oils that do not contain mineral oils of fossil origin.

[0029] The composition according to the present invention can comprise one or more naturally occurring oils selected from vegetable oils, animal fats and oils, used oils, oils produced by microorganisms, esters obtained by transesterification of fatty acid esters contained in one or more of these oils, and mixtures thereof.

[0030] Typically, naturally occurring oils contain phenolic lipids, fatty acids, and / or fatty acid esters (monoglycerides, diglycerides, triglycerides, fatty acid ethyl esters, fatty acid methyl esters) at a concentration of 50% or more, 60% or more, and preferably 70% or more.

[0031] Naturally derived oils contain fatty acid esters (monoglycerides, diglycerides, triglycerides, fatty acid ethyl esters, fatty acid methyl esters) and / or fatty acids at a concentration of 50%m or more, preferably 60%m or more, and preferably 70%m or more.

[0032] In one embodiment, the naturally occurring oil or mixture of naturally occurring oils can include fatty acid esters and free fatty acids containing 1-3 saturated or unsaturated C8-C24 acyl groups. When multiple acyl groups are present, they can be the same or different.

[0033] Compositions resulting from transesterification of fatty acid esters contained in these oils (such as compositions containing fatty acid methyl esters or fatty acid ethyl esters and containing impurities derived from the oil) may also be part of the naturally occurring compositions considered (treated) in the present invention.

[0034] Oils of natural origin may contain phenolic lipids in an amount of at least 50% m, preferably at least 60% m, preferably at least 70% m. These phenolic lipids include in particular compounds of the following chemical formula: [ka]

[0035] where R is a C10-C30 linear alkyl group, optionally C12-C20, e.g., C15, saturated or unsaturated, and substituted or unsubstituted with a heteroatom selected from O, N, or S. 1 is hydrogen or a hydroxyl group, R 2 is hydrogen, a carboxyl group, or an ester; R 3is hydrogen.

[0036] The oils of natural origin may in particular contain one or more of the following phenolic lipids: - alkylated phenols, in which the alkyl group is C10-C30 linear, optionally C12-C20, for example C15, saturated or unsaturated, and substituted or unsubstituted with heteroatoms selected from O, N or S; - alkylresorcinols, in which the alkyl group is C10-C30 linear, optionally C12-C20, for example C15, saturated or unsaturated, and substituted or not by heteroatoms selected from O, N or S; - anacardic acids, in which the alkyl group is C10-C30 linear, optionally C12-C20, for example C15, saturated or unsaturated, substituted or unsubstituted by heteroatoms selected from O, N or S.

[0037] The vegetable oil may be selected from pine oil, rapeseed oil, sunflower oil, castor oil, groundnut oil, linseed oil, babassu oil, hemp oil, linola oil, jatropha oil, peanut oil, rice bran oil, mustard oil, carinata oil, coconut oil, copra oil, olive oil, palm oil, cotton oil, corn oil, palm kernel oil, soybean oil, mallow oil, grape seed oil, argan oil, jojoba oil, sesame oil, walnut oil, hazelnut oil, tung oil, rice oil, safflower oil, algae oil, used oil, nut shell oil (especially cashew nut shell oil), and any combination thereof.

[0038] Used oils include used cooking oils (used edible oils) and oils recovered from residual water (greases recovered from traps and drains, gutter oils, sewage oils recovered from water treatment plants, used oils and fats recovered from food factories, etc.).

[0039] The animal fats may be selected from beef tallow, lard, fats (yellow and brown), fish oils and dairy fats.

[0040] Naturally occurring oils may be oils produced by natural or genetically modified microorganisms such as bacteria, yeasts (especially oleaginous yeasts), algae, prokaryotes, or eukaryotes, and in particular, these oils may be recovered by well-known mechanical or chemical extraction methods.

[0041] The aforementioned oils of natural origin are mostly rich in triglycerides or phenolic lipids, and also contain free fatty acids, monoglycerides, diglycerides and / or many other organic and inorganic components, in particular phospholipids, sterols, tocopherols, tocotrienols, hydrocarbons, pigments (gossypol, chlorophyll), vitamins (carotenoids), sterol glycosides, glycolipids, protein fragments, traces of pesticides and metals, as well as resinous and mucilaginous substances. Among the latter components, certain compounds, in particular those containing heteroatoms, are contaminants that are desirable to at least partially remove before further processing.

[0042] Thus, the renewable oil compositions of the present invention typically contain heteroatoms, including especially phosphorus and / or nitrogen, generally in the form of organic compounds, especially lipids.

[0043] The phosphorus content of the naturally occurring composition may be, for example, 20 ppm or more, or 50 ppm or more, for example, 50 ppm to 1500 ppm, or 200 ppm to 1200 ppm, as measured by X-ray fluorescence or ICP by UOP389 method.

[0044] The nitrogen content of the naturally occurring composition can be 50 ppm or more, such as 50 ppm to 1200 ppm, or 200 ppm to 2000 ppm, as measured, for example, by X-ray fluorescence.

[0045] The naturally occurring composition may further contain one or more other heteroatoms, such as alkali metals, especially potassium, alkaline earth metals, chlorine, etc. The content of these heteroatoms may vary depending on the composition of the composition. This can be measured by elemental analysis of the X-ray fluorescence type or by ICP.

[0046] In the naturally occurring compositions contemplated by the present invention, phosphorus can be present especially in the form of phosphatides, the most common of which are phosphatidic acid, phosphatidylethanolamine, phosphatidylcholine, phosphatidylinositol and phosphates. These compounds are often charged due to their low (phosphate group) or high (amino group) pKa and can therefore contain alkali and alkaline earth elements or absorb metallic cations such as copper and iron.

[0047] Figure 3 shows the different forms of phospholipids in water as a function of pH, where the R group represents diglyceride. Note that phosphatidylcholine (denoted PC) and phosphatidylinositol (denoted PI) are hydratable regardless of pH, phosphatidylethanolamine (denoted PE) is hydratable at pH 2-3, whereas phosphatidic acid (denoted PA) is hydratable above pH 4 if it is not chelated by cations present in the mixture, in which case it remains in the organic phase.

[0048] The term "hydratable compound" refers to a compound that is at least partially soluble in water, the solubility of which may be dependent on pH, as discussed above.

[0049] In the present invention, compounds hydratable at neutral pH (pH=7) are considered to be compounds which are at least partially soluble or completely soluble in water at neutral pH at the temperature conditions of the treatment carried out. In particular, a component is considered to be at least partially soluble in water at neutral pH if at least 40% of the component is dissolved at the temperature conditions of the treatment carried out. The treatment conditions carried out are in particular the conditions of washing with water at neutral pH described below.

[0050] Phosphorus compounds that are hydratable at neutral pH include, inter alia, hydratable phosphates, phosphatidylcholines, phosphatidylinositols, and, to a lesser extent, phosphatidylglycerols.

[0051] Nitrogen is present in phosphatidylcholine and phosphatidylethanolamine, and may also be present in naturally occurring compositions in the form of chlorophyll, protein residues, and fatty amines.

[0052] Nitrogen compounds hydratable at neutral pH include, inter alia, phosphatidylcholine and, to a lesser extent, phosphatidylinositol.

[0053] However, the present invention is not limited to these compounds and in particular can take into consideration all compounds that are hydratable at a specifiable neutral pH.

[0054] In particular, analyses can be carried out on the composition to be treated to identify and quantify compounds that are hydratable at neutral pH, to identify organic compounds containing phosphorus and / or nitrogen, to separate these compounds and to proceed with solubility tests in water, particularly at different pH levels at the temperature conditions of the treatment carried out. Identification of the compounds can be carried out using, in particular, the techniques mentioned above (NMR, mass spectroscopy, ion chromatography, liquid chromatography combined with mass spectrometry and high performance thin layer chromatography).

[0055] [Method of determining removal treatment] Another object of the present invention relates to a method for determining the heteroatom removal treatment to be applied to a composition of naturally occurring oils containing heteroatoms and lipids (chosen from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters and / or mixtures of two or more of these compounds) in order to achieve a target content of heteroatoms (in particular phosphorus and / or nitrogen).

[0056] The method according to the present invention comprises the following steps: (a) determining at least one parameter representative of the quality of a composition using the determination method of the present invention; (b) estimating, using said parameters, the residual content of at least one heteroatom selected from phosphorus and nitrogen, which corresponds to the content of at least one heteroatom after removal of compounds hydratable at pH=7 containing said heteroatom, (c) determining the treatment to be applied to said composition in order to reach a target content of at least one heteroatom, in particular chosen from phosphorus and / or nitrogen, at the output of the treatment, by choosing from: (i) washing with water of neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) Washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds. wherein said residual content is compared with a target content, and if the residual content is less than or equal to the target content, process (i) is selected, otherwise a database or model configured to provide an estimate of the content of at least one heteroatom at the output of each of processes (ii)-(iv) is used based on the content of this heteroatom at the input of the process being equal to the residual content, and the process whose estimated content at the output is less than or equal to the target content and optionally has the fewest number of processing steps is selected.

[0057] It is therefore possible to determine a process, in particular one with the fewest steps, which allows to obtain a target content of heteroatoms, in particular P and / or N, which makes it possible to reach this target content, regardless of the initial phosphorus and / or nitrogen content of the composition.

[0058] In particular, the processes that allow reaching the target content for phosphorus, nitrogen or both can be selected. Then, in step (a), a parameter representative of the quality of the composition for phosphorus, a parameter representative of the quality of the composition for nitrogen or a parameter for both is determined. The database or model used in step (c) is configured to provide an estimate of the phosphorus content, the nitrogen content or both at the output of each of the processes (ii) to (iv) depending on the content of this heteroatom at the input of the process being equal to the residual content.

[0059] In the step (c), a situation may occur in which the estimated content at the time of output does not become equal to or less than the target content. In this case, the steps (a) to (c) can be advantageously repeated by diluting the naturally derived composition with another naturally derived composition, in particular a composition having a larger parameter representing quality than the naturally derived composition (e.g., a composition previously determined by the determination method of the present invention).

[0060] This allows the use of feedstocks where conventional treatments for removing heteroatoms have not been effective enough (where the amount of heteroatoms, particularly phosphorus and / or nitrogen, has not been sufficiently reduced to reach the target specifications).

[0061] Advantageously, the database and / or model can be configured to provide an estimate of the content of at least one heteroatom at the output of each process (i) to (iv) obtained for different operating conditions of said processes, and in step (c) the process and operating conditions of this process can be selected which result in an estimated content at the output equal to or less than the target content, and optionally the process and operating conditions of this process which result in a minimum number of processing steps and / or which result in a minimum amount of reagents used. It is thus possible to optimize the processing conditions for each raw material, in particular to reduce the amount of reagents used and thus to reduce costs.

[0062] The determination method according to the invention can in particular be used for compositions of natural origin as defined above.

[0063] The database or model used in the method is configured to provide estimates of the heteroatom content (at least P and / or N) at the output of the treatment. These can be established in advance by tests on naturally occurring compositions in each of the treatments (i) to (iv). Thus, for each test and for each treatment type, and optionally for the different operating conditions of each treatment, it is possible to determine: - the total content in each composition of at least one heteroatom selected from phosphorus and nitrogen before and after treatment; - the total content of at least one heteroatom in said heteroatom compounds that are hydratable at neutral pH in each composition.

[0064] The determination procedure according to the invention may further comprise a step (d) of processing the composition, which is subjected to the treatment selected in step (c) to recover a naturally occurring composition having a reduced content of at least one heteroatom, in particular at least one heteroatom selected from phosphorus and nitrogen, and advantageously at least one other heteroatom selected in particular from metals, alkali metals, alkaline earth metals and chlorine.

[0065] The composition thus treated is then subjected to a hydrotreatment step (optionally mixed with hydrocarbons of fossil origin) and then advantageously to an isomerization step to produce renewable fuels (in particular of diesel type).

[0066] Alternatively, the composition so treated may be subjected to a transesterification or esterification step to produce a biodiesel type fuel.

[0067] The removal treatment steps (i)-(iv), as well as the hydrotreating step, can be as described below in connection with the method for reducing the heteroatom content of a naturally occurring composition of the invention.

[0068] Methods for reducing heteroatom content The present invention is also directed to a method for reducing the heteroatom content in a naturally occurring composition comprising heteroatoms and lipids, the heteroatoms being selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters, and / or mixtures of two or more of these compounds, in particular as defined above.

[0069] In a first embodiment, the method includes: (E1) determining a heteroatom removal treatment to be applied to the naturally occurring composition by the method of the present invention to reach a target content of at least one heteroatom; and (E2) subjecting the naturally occurring composition to the treatment determined in step (E1).

[0070] In a second embodiment, the method includes: (E'2) A heteroatom removal step in which the naturally occurring composition is subjected to a treatment selected from the following: (i) washing with water of neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) Washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds. Here, the naturally occurring composition has a parameter representative of the quality of the composition, previously determined using the determination method of the present invention, and this parameter is equal to or greater than a threshold at which the effectiveness of the removal step is sufficient to reduce the heteroatom content of the composition to below the target content.

[0071] This allows for the selection of naturally occurring compositions that can be processed to achieve specific specifications upstream of the removal step, particularly optimizing the operation of existing processing equipment.

[0072] These parameter thresholds can be pre-determined, for example, by statistical processing of the base data and / or by models as described above, using the same database as described above.

[0073] Each of the four contemplated processes (i)-(iv) includes a step of washing with water at neutral pH, which, depending on the process, may be followed by a step of removing compounds that are hydratable at a pH other than neutral pH, each of which is described in more detail below.

[0074] In each embodiment, the process for reducing the heteroatom content may further comprise a step (E3) of hydrotreating the product obtained directly from step (E2) or (E'2).

[0075] [Step of washing with neutral pH water] Washing the naturally occurring composition with water at neutral pH makes it possible to significantly reduce the heteroatom content (in particular the content of heteroatoms selected from phosphorus, nitrogen, chlorine, alkali metals and alkaline earth metals), and in particular to remove nitrogen and / or phosphorus compounds contained in nitrogen and / or phosphorus compounds that are hydratable at neutral pH.

[0076] This water washing step is carried out using water with neutral pH, in other words without the addition of chemicals (acids or bases) aimed at modifying the pH. This is usually a pure water wash. This wash is usually carried out with agitation to promote contact between the water and the oil.

[0077] If the residual heteroatom content (especially P and / or N) estimated from the quality parameters is lower than the target content, this washing may be sufficient to remove all or almost all of these heteroatoms without carrying out other treatments to remove them (such as the additional steps for removal provided in steps (ii) to (iv)).

[0078] Typically, this water wash is carried out at atmospheric pressure and at a temperature ranging from ambient temperature to the temperature at which the composition becomes liquid, which can be determined depending on the pour point of the composition, and can be above 50°C, for example between 50 and 100°C.

[0079] This washing step is typically carried out by contacting the composition with water at neutral pH, followed by separation of the oil and water phases, with the recovered oil phase forming a composition having a reduced content of compounds hydratable at neutral pH. This contacting can be repeated one or more times. After each contact, the oil and water phases are separated, and the separated oil phase is again contacted with water at neutral pH or recovered. This separation can be carried out by conventional separation techniques.

[0080] This washing can in particular be carried out by contacting the composition with water at neutral pH, preferably with stirring, for a time sufficient to mix the two phases, for example from 15 minutes to 1 hour.

[0081] Advantageously, during the washing step, the water / composition mass ratio can be between 1:99 and 10:90. A small amount of water is sufficient to significantly reduce the heteroatom content.

[0082] This washing step can be carried out in a specific chamber dedicated to this step, for example a chamber equipped with a water / oil mixing device (recirculation pump with water injection upstream of the pump, stirring device, etc.).

[0083] However, advantageously, the washing step can also be carried out in a chamber chosen from storage trays, desalting capacities, tanks, in particular separation tanks of the water / oil type. The washing can advantageously be carried out in an existing chamber of the treatment unit.

[0084] The product from the washing step is usually recovered by water / oil separation techniques (e.g. centrifugation and / or sedimentation and / or water / oil separation techniques using applied electric fields). If separation is carried out by sedimentation, it can be carried out in the same chamber as that used for washing.

[0085] In particular, the product recovered at the end of this washing step may constitute a refined composition, in particular a refined oil (which may subsequently be subjected directly to a hydrotreating step), or a partially refined oil (which may subsequently be subjected directly to a step of removing hydratable compounds at a pH other than neutral pH and then to a step of removing non-hydratable compounds, or which may subsequently be subjected directly to only a step of removing non-hydratable compounds, prior to a subsequent step such as hydrotreating).

[0086] [Step of removing compounds that can be hydrated at a pH other than neutral pH (basic pH or acidic pH)] This step generally makes it possible to remove some of the chlorine and especially hydratable compounds of phosphorus, nitrogen, metals, etc. that were not removed in the neutral pH water washing step.

[0087] This removal step may include one or more treatments selected from, for example, degumming in an acidic or basic medium and treatment by cavitation, each of which is followed by a step of separating the oil and aqueous phases, the recovered oil phase having a reduced content of compounds capable of hydrating at a pH other than neutral pH. This separation may be carried out by any conventional separation technique.

[0088] In particular, it is possible to carry out multiple degumming treatments in acidic and basic media to remove compounds that are hydratable at acidic and basic pH, respectively.

[0089] The degumming process can be a water degumming process, in which the oil to be treated is usually heated to 60-70°C, water with added basic compounds (e.g. NaOH) or acidic compounds (e.g. citric acid or phosphoric acid) is added and mixed for about 30 minutes. The hydrated gums are then separated by centrifugation and the degummed oil is dried in vacuum. This method may require the addition of live steam to the treatment for a short period of time. The correct amount of water usually corresponds to about 75% by weight of the phospholipid content of the oil to be treated. Insufficient water produces a dark viscous gum, while too much water results in excessive oil loss by hydrolysis. Water degummed oils usually still contain phospholipids (50-200 ppm by weight).

[0090] Acids can be used for degumming, and the oil to be treated is usually heated to 60-70°C, a mixture of water and acid is added, and mixed for about 30 minutes. Usually, phosphoric acid or citric acid is used.

[0091] The degumming process can be an enzymatic degumming process, in which an enzyme (e.g., the modern degumming enzyme phospholipase A1) converts phospholipids into lysophospholipids and free fatty acids. This process involves three main steps: (1) Adjustment of pH with a buffer solution, (2) Enzyme reactions in the reservoir; (3) Separation of sludge and oil.

[0092] The oil which is enzymatically degummed in this manner can be unrefined oil or one which has previously been water degummed.

[0093] The Lipid Manual (Frank D. Gunstone, John L. Harwood, and Albert J. Dykstra, eds.) describes many variations and details of the degumming process.

[0094] The treatment may be by cavitation (in particular hydrodynamic cavitation) of the oil treated in the presence of water under conditions effective to generate cavitational properties and to transfer at least a portion of the impurities contained in the oil to the aqueous phase.

[0095] Cavitation is the formation of vapor bubbles in a liquid flowing through a region where the pressure of the liquid is lower than its vapor pressure at the temperature of interest.

[0096] Cavitation is the phenomenon of nucleation, growth and implosion (collapse) of vapour- or gas-filled cavities and can be obtained by the passage of ultrasound (acoustic cavitation), lasers, the injection of vapour into a cold fluid, or by changes in flow and pressure (hydrodynamic cavitation).

[0097] Hydrodynamic cavitation can be produced by passing the mixture to be treated through one or more cavitation devices.

[0098] Thus, the hydrodynamic cavitation method may include the following steps: The oil to be treated is pumped into the cavitation device, It creates cavitation properties to remove impurities.

[0099] For example, the cavitation devices disclosed in International Publication No. 201098783, U.S. Patent No. 8,911,808, U.S. Patent No. 7,762,715, and U.S. Patent No. 8,042,989 are suitable for the present invention and can be used.

[0100] For example, a cavitation device such as that disclosed in U.S. Patent No. 8,911,808, which has a flow path through which a fluid is pumped and in which a predetermined pump pressure is applied, preferably in the range of 340 kPa to 34 MPA, is suitable for the present invention.

[0101] In the process by hydrodynamic cavitation, the phospholipids are hydrated into gums which are insoluble in oil and can be easily separated by settling, filtration, centrifugation, etc. in the form of a sludge which forms an aqueous phase.

[0102] In one embodiment, the treatment by cavitation, in particular hydrodynamic cavitation, can be carried out in the presence of a degumming agent, which can be selected from water, steam, acids, complexing agents and mixtures thereof.

[0103] The acid is, for example, a strong acid, especially an inorganic acid (phosphoric acid, sulfuric acid, etc.).

[0104] The complexing agent is, for example, a weak organic acid (or its corresponding anhydride), such as acetic acid, citric acid, oxalic acid, tartaric acid, malic acid, maleic acid, fumaric acid, aspartic acid amino acid, ethylenediaminetetraacetic acid (EDTA), and the like.

[0105] Preferably, the degumming agent comprises water, steam, phosphoric acid, acetic acid, citric acid, oxalic acid, tartaric acid, malic acid, fumaric acid, aspartic acid, ethylenediaminetetraacetic acid, a base, a salt, a chelating agent, a crown ether, or maleic anhydride.

[0106] Cavitational treatment can be carried out at temperatures close to or below ambient temperature, for example at 15-25° C. Hydrodynamic cavitation, however, can be carried out at temperatures between 10 and 90° C., preferably between 25 and 75° C., more preferably between 30 and 60° C.

[0107] For example, it is possible to proceed as described in WO2019229035.

[0108] The product resulting from this removal step can be separated by one or more of the known techniques such as settling, centrifugation, filtration, distillation, extraction or washing, preferably settling, centrifugation, filtration. The product recovered after separation of the aqueous water is the oil phase, which constitutes the partially refined composition or oil, which is then subjected to a non-hydratable compound removal step.

[0109] [Step of Removing Non-hydratable Compounds] This step typically removes non-hydratable compounds not removed in the neutral pH water washing step and the optional step of removing compounds that are hydratable at other than neutral pH, particularly non-hydratable compounds such as phosphorus, nitrogen, etc. (such as non-hydratable phospholipids (such as calcium and magnesium salts of phosphatidic acid and phosphatidylethanolamine)), as well as non-hydratable compounds of other elements (such as sulfur), and / or a portion of the residual organic chlorines.

[0110] This step typically includes one or more treatments selected from the group consisting of bleaching, contacting the treated material with an absorbent, contacting the treated material with an ion exchange resin, weak acid washing, treatment with a guard bed, filtration, and extraction with a solvent, each of which is followed by a step of separating the oil and aqueous phases, with the recovered oil phase forming a composition having a reduced content of non-hydratable compounds. This separation can be carried out by any separation technique.

[0111] Bleaching is a known technique and is commonly used to decolorize and refine chemically or physically refined oils. In general, bleaching removes soaps, residual phospholipids, trace metals, and certain oxidation products. Bleaching catalyzes the removal of carotenes, and absorbents also catalyze the decomposition of peroxides. Another function is the removal of peroxides and secondary oxidation products.

[0112] This treatment involves contacting the product to be treated with an absorbent such as absorbent clay, synthetic amorphous silica, activated carbon, etc. Optionally, prior to this contacting, the product can be mixed with an acid to break down metal ion / phospholipid complexes.

[0113] The important parameters of the bleaching process are absorbent type and dosage, temperature, time, humidity, and filtration, as described in "Handbook of Lipids" edited by Frank D. Gunstone, John L. Harwood, and Albert J. Dykstra (3rd ed., Chapter 3.7) or "A Practical Guide to Vegetable Oil Processing" 2nd ed. by Monoy K. Gupta.

[0114] Another possible treatment is with an ion exchange resin, which involves contacting the feedstock with an ion exchange resin in a pretreatment zone at pretreatment conditions, for example an acidic ion exchange resin such as Amberlyst™-15, which can be used as a bed in a reactor through which the feedstock flows upstream or downstream.

[0115] Another possible treatment is washing with a weak acid. This treatment is carried out by contacting the product with an acid such as sulfuric acid, nitric acid, phosphoric acid or hydrochloric acid in a reactor. The product acid can be contacted in a discontinuous or continuous process. Contacting is usually carried out with a dilute acid solution at ambient temperature and atmospheric pressure. If contacting is carried out continuously, it is usually carried out in countercurrent.

[0116] Another possible treatment is the use of guard beds, which are well known in the art. These can be guard beds containing alumina, with or without demetallization catalysts such as nickel, cobalt, and / or molybdenum.

[0117] Filtration and solvent extraction techniques are other options that can be used.

[0118] The recovered product, particularly at the end (particularly immediately after) of the step of removing the non-hydratable compounds, constitutes a refined composition or oil, which is then subjected to a step of conversion, preferably by hydroprocessing, into a naturally occurring fuel.

[0119] [Hydrogenation step] The process for reducing the heteroatom content of a renewable oil composition according to the invention may further comprise, either at the end of step (E2) or immediately at the end of step (E'2), a step (E3) of hydrotreating the product.

[0120] The composition treated in this hydrotreating step is therefore a purified composition, preferably obtainable directly from any of processes (i) to (iv).

[0121] The purified composition typically has at least one, and preferably all, of the following characteristics: - phosphorus content less than 200 ppm, preferably less than 100 ppm or less than 50 ppm, more preferably less than 3 ppm Nitrogen content less than 200 ppm, preferably less than 100 ppm, more preferably less than 50 ppm - Chlorine content less than 50 ppm, preferably less than 20 ppm, more preferably less than 5 ppm - Metal content less than 50ppm, preferably less than 10ppm

[0122] In one embodiment, the refined composition can be mixed with one or more mineral hydrocarbon fractions and hydrotreated. The mineral hydrocarbon fractions can be naphtha, kerosene, or diesel type. The mineral hydrocarbon fractions can be added in an amount ranging from 1 to 98% by weight, or from 1 to 95% by weight, or at any interval defined by any two of these limits. The mineral hydrocarbon fractions generally contain organic sulfur compounds, which provide the sulfur necessary to maintain the catalytic activity of the catalysts containing cobalt, nickel, tungsten, and molybdenum. At the same time, the mineral hydrocarbon fractions are at least partially desulfurized.

[0123] This hydrotreating step is usually carried out in the presence of dihydrogen and at least one catalyst, and is included in the product obtained directly from any of the processes (i) to (iv). The fatty acid esters and free fatty acids are converted to linear or substantially linear paraffins. Hydrotreating can be carried out in the presence of dihydrogen at pressures ranging from 0.01 to 10 MPa and at temperatures between 100° C. and 550° C. The dihydrogen to feed ratio can range from 100 to 2000 Nl / l.

[0124] This hydrotreating may include one or more steps selected from hydrodeoxygenation, decarboxylation, and decarbonylation.

[0125] The hydrodeoxygenation is preferably carried out in a continuous fixed bed reactor, a reactor with a continuous stirred tank or a slurry type reactor containing as catalytic phase a solid catalyst which may be selected from oxides of Ni, Mo, W, Co or mixtures of NiW, NiMo, CoMo, NiCoW, NiCoMo, NiMoW, CoMoW, etc., or sulfur, preferably supported on carbon, alumina, silica, titanium oxide or zirconia.

[0126] The hydrodeoxygenation can be carried out at a temperature of 200-500°C, preferably 220-400°C, under a pressure of 1 MPa to 10 MPa (10-100 bar), e.g. 6 MPa, with a dihydrogen / oil ratio of 100-2000, preferably 350-1500, e.g. 800 Nl H2 per litre of oil.

[0127] The decarboxylation and / or decarbonylation is preferably carried out in a discontinuous tank reactor, a continuous fixed bed reactor, a continuous stirred tank reactor or a sludge reactor in the presence of a solid catalyst. The decarboxylation and / or decarbonylation can be carried out directly on the glycerides, any esters or free fatty acids.

[0128] The catalyst can be selected from: - oxides or sulfides of Ni, Mo, W, Co, NiW, NiMo, CoMo, NiCoW, NiCoMo, NiMoW and CoMoW as catalytic phase, preferably supported on carbon, alumina, silica, titanium oxide or zirconia, - Mixtures of Group 10 (Ni, Pt, and Pd) and Group 11 (Cu and Ag) metals or alloys supported on carbon, magnesia, zinc oxide, spinel (Mg2Al2O4, ZnAl2O4), perovskites (BaTiO3, ZnTiO3), calcium silicates (such as xonotlite), alumina, silica, silica-alumina, or mixtures thereof.

[0129] For optimal performance and continued stable operation, it is preferred that the active metal components of the catalyst, be they Ni, Mo, W, Co, or mixtures, be in the form of sulfides. Therefore, it is preferred that trace amounts of decomposable sulfur compounds (thermal or catalytic) be present in the feedstock or be added spontaneously to keep the metal sulfides in the sulfide state. By way of example, these sulfur compounds include H2S, COS, CS2, mercaptans (e.g., methyl sulfide), thioethers (e.g., dimethyl sulfide), disulfides (e.g., dimethyl disulfide), thiophene compounds, and tetrahydrothiophene compounds.

[0130] Decarbonation and / or decarbonylation can also be carried out on basic oxides such as alkali metal oxides, alkaline earth oxides, lanthanide oxides, zinc oxide, spinels (Mg2Al2O4, ZnAl2O4), perovskites (BaTiO3, ZnTiO3), calcium silicates (such as xonotlite), in bulk or dispersed on neutral or basic supports, on basic zeolites (such as alkali or alkaline earth zeolites with low silica / alumina content obtained by exchange or impregnation).

[0131] Although dihydrogen is not required for the decarboxylation and / or decarbonylation reactions, it is preferred to carry out the decarboxylation and / or decarbonylation reactions in the presence of dihydrogen. In the presence of dihydrogen, highly adsorbed unsaturated species (e.g., when decarbonylation is the predominant reaction pathway) are removed from the catalyst surface by hydrogenation reactions, stabilizing catalyst activity. The presence of dihydrogen hydrogenates the double bonds in the acyl moieties of the fatty acids, resulting in paraffinic reaction products from the decarboxylation process.

[0132] The decarbonation and / or decarbonylation steps may be carried out in the presence of dihydrogen at a pressure between 0.01 and 10 MPa and at temperatures between 100 and 550° C. The ratio of dihydrogen to feedstock may be between 100 and 2000 Nl / l.

[0133] [System for determining heteroatom removal treatment] The present invention is also directed to a system for determining a heteroatom removal treatment to be applied to a composition of natural origin in order to reach a target content of at least one type of heteroatom, the system being configured (in particular programmed) to carry out steps (a) to (c) of the method for determining according to the present invention.

[0134] The determination system typically comprises one or more processors, such as a microprocessor, a microcontroller, etc. The system can be configured to receive the total content of at least one heteroatom selected from phosphorus and nitrogen in the composition, and the total content of hydratable compounds of the at least one heteroatom in the composition.

[0135] It usually includes an output or input / output interface, which can be a wireless communication interface (Bluetooth, WIFI, etc.) or a connector (network port, USB port, serial port, Firewire port, SCSI port, etc.). These input and / or output interfaces form a communication means (optionally bidirectional) between the determination system and, for example, a user interface, and in particular enable the determination system to receive the content associated with said composition.

[0136] The determination system may also include storage means such as a random access memory (RAM), an electrically erasable programmable read only memory (EEPROM), a flash memory, an external memory, etc. These storage means may store received data, measurements, calculations, databases and / or models, one or more computer programs, etc.

[0137] Thus, the decision system may include at least one processor configured as follows. (a) receiving the total content of at least one heteroatom selected from phosphorus and nitrogen in the composition, receiving the total content of hydratable compounds of the at least one heteroatom in the composition, and determining, as a parameter representative of the quality of the composition, the ratio between the total content of the at least one heteroatom present in the compounds hydratable at neutral pH of the identified heteroatom and the total content of the heteroatom in the composition (this ratio is determined for phosphorus, for nitrogen or for each of these two heteroatoms), (b) estimating, using said parameters, the residual content of at least one heteroatom selected from phosphorus and nitrogen, said residual content corresponding to the content of said at least one heteroatom after removal of the compounds hydratable at pH=7 containing said heteroatom, (c) determining a treatment to be applied to said composition to reach a target content of said at least one heteroatom at the output of said treatment, selected from: (i) washing with water of neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) Washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds. At least one processor Comparing the residual content to a target content; If the residual content is equal to or less than the target content, select treatment (i); Otherwise, the method is configured to use a database or model configured to provide an estimate of the content of at least one type of heteroatom at the output of each of processes (ii) to (iv) based on the content of this heteroatom at the input of the process being equal to the residual content, and to select the process whose estimated content at output is less than or equal to the target content and optionally has the fewest number of processing steps.

[0138] The at least one processor may be further configured as follows. (c) if none of the estimated contents in the output is equal to or less than the target content, diluting the naturally derived composition with another naturally derived composition (optionally with a composition having a parameter representing the quality of the composition higher than the parameter representing the quality of the composition), and then repeating steps (a) to (c); and / or (c) selecting the process having an estimated content at output less than or equal to the target content, optionally the process having the fewest number of process steps and / or the least amount of reagents used, and the operating conditions of this process, and the database or model is configured to provide, for each process (ii) to (iv), an estimate of the content of the at least one heteroatom at output of the process, obtained for the different operating conditions of processes (i) to (iv).

[0139] In either case, the at least one processor may receive data via one or more input interfaces, or input and output interfaces, particularly of the type described above, and may store the database or the model in a storage means, particularly of the type described above.

[0140] Other characteristics and advantages of the invention will become apparent on reading the following description of particular embodiments of the invention, given for informational and non-limiting purposes, with reference to the attached drawings, in which: [Brief description of the drawings]

[0141] [Figure 1] FIG. 1 shows diagrammatically an exemplary embodiment of the processing method according to the invention. [Diagram 2] FIG. 2 shows a schematic of the washing chamber. [Diagram 3] FIG. 3 is a table showing the chemical formulas of phospholipids in water as a function of pH, with the R group representing diglycerides. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0142] FIG. 1 shows a schematic of a method for reducing the heteroatom content of naturally occurring composition H.

[0143] The naturally occurring composition H to be treated is first subjected to a step (a) of determining a parameter Q representative of its quality (here a parameter related to the phosphorus content).

[0144] This parameter Q can be expressed as follows (Equation 1).

number

[0145] In step (b), the residual phosphorus content is estimated from the parameter Q and is denoted [P]r. This residual content corresponds to the total phosphorus content minus the phosphorus content present in hydratable phosphorus compounds at neutral pH and can be calculated as follows (Equation 2):

number

[0146] In step (c), this residual content [P]r is compared with a desired target content (denoted as [P]c) and one of the treatments (i) to (iv) is selected as described above, and the composition is subjected to the retained treatment to obtain a purified composition.

[0147] Therefore, as shown in Figure 1, If [P]r<[P]c, only the step E1(a) of washing with water at neutral pH is carried out before the hydrotreatment step E3; If [P]r>[P]c, steps E1(a) and E1(c) (removal of non-hydratable compounds) can be carried out in succession, or steps E1(a) and E1(b) (removal of compounds hydratable at a pH other than neutral pH) can be carried out in succession, or steps E1(a), E1(b) and E1(c) can be carried out in succession, prior to the hydrotreatment step E3.

[0148] Figure 2 shows a chamber 1, for example a storage tray or a desalting capacity, containing a composition H. This chamber 1 is equipped with a recirculation circuit 2 with a pump 3. Upstream of the pump 3 with respect to the circulation direction of the circulation circuit 2, water can be injected into the circuit 2 by a duct 4. A tapping duct 5, located at the bottom of the chamber 1, allows the recovery of the oil after washing with water. EXAMPLES

[0149] Analysis of phosphorus content of various compositions of natural origin Table 1 shows the analytical results of the organic and aqueous phases recovered after liquid / liquid extraction of various compositions with aqueous solutions containing EDTA at pH = 7.

[0150] In the organic phase 31 P NMR measurements were carried out in deuterated chloroform (CDCl3), while measurements in aqueous phase were carried out in mixtures of deuterated water (DO) and methyl alcohol (MeOH), for example according to the protocol described below.

[0151] A precise amount of the renewable oil sample is taken in a vial and a precise amount of the phosphorus standard that dissolves in the organic phase and the aqueous phase is added to it. The sample is then dissolved in deuterated chloroform. A 0.2 M EDTA solution in MeOH / D2O at pH 7 is then added to maximize the analytical resolution, as described in the following literature articles: "Phosphorus-31 Nuclear Magnetic Resonance Studies of Biological Polyphosphates" by T. Groneck, M. Lande, M. Mudgett, and T. C. Meiers (1971) (Archives of Biochemistry and Biophysics, Vol. 142, pp. 508-513); "Phosphorus-31 Nuclear Magnetic Resonance Spectroscopy of Phospholipids" by T. O. Henderson, T. Groneck, and T. C. Meiers (1974) (Biochemistry, Vol. 13, No. 3, pp. 623-628). The aqueous and organic phases are then separated by leaving the mixture to stand overnight. 31Species are identified by chemical shift in comparison with standards of equivalent structure, and quantification is performed by the intensity of the standard soluble in the same phase initially introduced into the sample. 31 The ratio of P signal intensities is used.

[0152] Composition C1 is poultry fat, composition C2 is a mixture of fats from several animals, and composition C3 is pork fat. [Table 1]

[0153] The data in Table 1 make it possible to calculate the total content of phosphorus hydratable at pH 7 (corresponding to the sum of the P content from PC and PI and the P content from the aqueous phase; in Table 1, the added values ​​are shown in bold) and a parameter Q that expresses the quality of each composition, calculated by dividing the total content of P present in P compounds hydratable at pH 7 by the total content of P in the composition measured by XRF. EXAMPLES

[0154] [Washing with neutral pH water] Composition C3 of Example 1 was washed with water at neutral pH with water / fat ratios of 4, 8 and 12. Before measuring the phosphorus content of the oil phase, the water and fat were separated by centrifugation at 4800 g.

[0155] Table 2 shows the phosphorus content of the oil phase as determined by XRF for the various ratios tested. [Table 2]

[0156] It is noted that washing with 4% m water results in a significant reduction in phosphorus. Thus, for fat composition C3, with a composition quality parameter of 0.65, the water washing step makes it possible to remove almost all of the phosphorus present in the composition, which may then be directly processed in a hydrotreater to produce a fuel according to the phosphorus specification of the feed entering said hydrotreater.

Claims

1. 1. A method for determining a parameter representative of the quality of a naturally occurring composition comprising heteroatoms and lipids selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters and / or mixtures of two or more of these compounds, comprising: (A) determining a total content of at least one heteroatom selected from phosphorus and nitrogen in the composition; (B) identifying a compound of the at least one heteroatom that is hydratable at neutral pH and determining the total content of the at least one heteroatom of the composition that is present in the identified compound of the at least one heteroatom that is hydratable at neutral pH; (C) determining, as a parameter representative of the quality of the composition, the ratio of the total content of said at least one type of heteroatom present in the compounds of said heteroatom that are hydratable at a specified neutral pH to the total content of said heteroatom in said composition, for phosphorus, nitrogen or each of these two heteroatoms; A method for determining a parameter, comprising:

2. 2. The method for determining a parameter according to claim 1, wherein step (B) is carried out using an analytical technique selected from NMR, mass spectroscopy, ion chromatography, liquid chromatography combined with mass spectrometry, and high performance thin layer chromatography.

3. 3. The method for determining a parameter according to claim 1 or 2, wherein the naturally occurring composition comprises one or more oils selected from vegetable oils, animal fats and oils, used oils, oils produced by microorganisms, esters obtained by transesterification of fatty acid esters contained in one or more of these oils, and mixtures thereof.

4. The present invention is applied to compositions of natural origin comprising heteroatoms and lipids selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters, and / or mixtures of two or more of these compounds, (a) determining at least one parameter representative of the quality of the composition by a method for determining a parameter according to any one of claims 1 to 3, (b) estimating from the quality-representative parameters the residual content of at least one heteroatom selected from phosphorus and nitrogen, said residual content corresponding to the content of at least one heteroatom after removal of the compounds hydratable at pH=7 which contain said heteroatom; (c) determining, at the output of the treatment, a treatment to be applied to said composition in order to reach a target content of at least one heteroatom by selecting from the following: (i) washing with water at neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds; Including, The residual content is compared to a target content; If the residual content is equal to or less than the target content, treatment (i) is selected; Otherwise, a database or model configured to provide an estimate of the content of at least one heteroatom at the output of each of the processes (ii) to (iv) is used based on the content of this heteroatom at the input of the process being equal to the residual content, and if the estimated content at the output is less than or equal to the target content, optionally the process having the fewest number of processing steps is selected.

5. A method for determining a heteroatom removal treatment as described in claim 4, wherein in step (c), if the estimated content at the time of output is not equal to or less than the target content, steps (a) to (c) are repeated by diluting the naturally occurring composition with another naturally occurring composition, optionally by diluting with a composition whose parameter representing the quality of the composition is greater than the parameter representing the quality of the composition.

6. 6. A method for determining a heteroatom removal process according to claim 4 or 5, wherein the database or model is configured to provide, for each process (ii) to (iv), an estimate of the content of at least one heteroatom at the output of said process, obtained for different operating conditions of processes (i) and (iv), and in step (c) a process and operating conditions of said process are selected whose estimated content at the output is less than or equal to the target content, and optionally which has a minimum number of process steps and / or which uses a minimum amount of reagents.

7. The method for determining the removal treatment of heteroatoms according to any one of claims 4 to 6, wherein the naturally derived composition comprises one or more oils selected from vegetable oils, animal fats, used oils, oils produced by microorganisms, esters obtained by transesterification of fatty acid esters contained in one or more of these oils, and mixtures thereof.

8. 1. A method for reducing the heteroatom content of a naturally occurring composition comprising heteroatoms and lipids selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters, and / or mixtures of two or more of these compounds, comprising: (E1) determining a heteroatom removal treatment to be applied to the naturally occurring composition to reach a target content of at least one heteroatom by the method for determining a heteroatom removal treatment according to any one of claims 4 to 7; and (E2) subjecting the naturally derived composition to the treatment determined in step (E1); A method for reducing heteroatom content, comprising:

9. 1. A method for reducing the heteroatom content of a naturally occurring composition comprising heteroatoms and lipids selected from phenolic lipids, fatty acids, triglycerides, diglycerides, monoglycerides, phospholipids, fatty acid esters, and / or mixtures of two or more of these compounds, comprising: (E'2) A heteroatom removal step in which the naturally occurring composition is subjected to a treatment selected from the following: (i) washing with water at neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds; Including, A method for reducing the heteroatom content, wherein a naturally occurring composition has a parameter indicative of the quality of the composition, previously determined by the determination method of any one of claims 1 to 3, the parameter being equal to or greater than a threshold value such that the effectiveness of the removal step is sufficient to reduce the heteroatom content of the composition to or below a target content.

10. 10. A process for reducing the heteroatom content according to claim 8 or 9, further comprising a hydrotreatment step (E3) of the product obtained directly from step (E2) or step (E'2).

11. The method for reducing the heteroatom content according to any one of claims 8 to 10, wherein the naturally derived composition comprises one or more oils selected from vegetable oils, animal fats, used oils, oils produced by microorganisms, esters obtained by transesterification of fatty acid esters contained in one or more of these oils, and mixtures thereof.

12. The method for reducing the heteroatom content according to any one of claims 8 to 11, wherein the washing with water having a neutral pH in each of the treatments (i) to (iv) in step (E2) or step (E'2) is carried out in a water / composition mass ratio of 1:99 to 10:

90.

13. 13. The method for reducing the heteroatom content according to any one of claims 8 to 12, wherein the washing with neutral pH water of each of the treatments (i) to (iv) in step (E2) or step (E'2) is carried out in a chamber selected from a storage tray, a desalting capacity, a tank.

14. A system for determining a heteroatom removal treatment to be applied to a naturally occurring composition in order to reach a target content of at least one type of heteroatom, the system being configured to carry out steps (a) to (c) of the method for determining a heteroatom removal treatment according to any one of claims 4 to 6, comprising at least one processor configured as follows: (a) a processor for receiving the total content of at least one heteroatom selected from phosphorus and nitrogen in the composition, receiving the total content of hydratable compounds of the at least one heteroatom in the composition, and determining, as a parameter representative of the quality of the composition, a ratio of the total content of the at least one heteroatom present in compounds hydratable at neutral pH of the identified heteroatom to the total content of the heteroatom in the composition, for phosphorus, for nitrogen, or for each of these two heteroatoms; (b) a processor that uses the parameters to estimate a residual content of at least one heteroatom selected from phosphorus and nitrogen, the residual content corresponding to the content of the at least one heteroatom after removal of compounds hydratable at pH=7 that contain the heteroatom; (c) a processor for determining a treatment to be applied to the composition to reach a target content of at least one heteroatom at the output of the treatment, selected from the following: (i) washing with water at neutral pH; (ii) washing with water at neutral pH followed by removal of non-hydratable compounds; (iii) washing with water at neutral pH followed by removal of compounds that are hydratable at a pH other than neutral pH; (iv) washing with water at neutral pH, followed by removal of hydratable compounds at a pH other than neutral pH, and then removal of non-hydratable compounds; Including, At least one processor Comparing the residual content to a target content; If the residual content is equal to or less than the target content, select treatment (i); Otherwise, the system for determining heteroatom removal processes is configured to use a database or model configured to provide an estimate of the content of at least one heteroatom at the output of each process (ii) to (iv) based on the content of this heteroatom at the input of the process being equal to the residual content, and to select the process whose estimated content at the output is less than or equal to the target content and, optionally, which has the fewest number of process steps.

15. The at least one processor further comprises: (c) if the estimated content at the output is not equal to or less than the target content, steps (a) to (c) are repeated by diluting the naturally derived composition with another naturally derived composition, optionally with a composition whose parameter representing the quality of the composition is greater than the parameter representing the quality of the composition; and / or (c) the database or model is configured to provide, for each process (ii) to (iv), an estimate of the content of said at least one heteroatom at the output of said process, obtained for different operating conditions of the processes (i) to (iv), and selecting the process whose estimated content at the output is less than or equal to the target content, optionally the process having the fewest number of process steps and / or using the least amount of reagents, and the operating conditions of this process; The system for determining a heteroatom removal process according to claim 14, configured to:

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