PROCESS FOR PRODUCING A SOLID / LIQUID EXTRACTION SOLVENT

Abstract

The present invention relates to a cost-effective process for producing a solvent comprising 2-methyloxolane and water for the production of crude oil and a desolventized oilcake from a biological substrate. Abstract figure: Figure 3

Description

Title of the invention: METHOD FOR PRODUCING A SOLID / LIQUID EXTRACTION SOLVENT Technical field

[0001] The present disclosure relates to the field of the production of oils and oilseed cakes from a biological substrate by a solid-liquid extraction process using 2-methyloxolane. Previous technique

[0002] There are two main known categories of oil and oilcake production processes: the mechanical process which makes it possible to obtain virgin oil and the solid / liquid extraction process which makes it possible to produce oil from a solid substrate.

[0003] Conventionally, the solid / liquid extraction process comprises a solid / liquid extraction step involving a solvent to obtain a solvated press cake and a liquid fraction comprising an oil and the solvent. The two processes, mechanical and solid / liquid extraction, can be combined, namely a first mechanical process followed by a solid / liquid extraction, the solid being constituted by the solid residue from the mechanical process.

[0004] Oils hold an important place in the food, pharmaceutical, nutraceutical and cosmetic industries.

[0005] Oilcakes, which are the desolventized solid residues from the solid / liquid extraction step, are mainly used in animal feed, and increasingly in human food, primarily as a protein supplement, but also as a source of metabolizable energy.

[0006] Currently, hexane is the most widely used solvent in the solid / liquid extraction process because it offers advantageous properties. Hexane allows for high-yield oil extraction (>97%) and leaves less than 3% residual oil in the solid substrate, thus preventing it from becoming rancid. Hexane is easy to separate from the extracted oil, has a suitable boiling point (i.e., high enough to limit losses during extraction but low enough to limit energy consumption during its separation from the extracted oil and during its recycling), is stable, and exhibits good lipid selectivity.

[0007] However, hexane has significant drawbacks. It is petroleum-derived, neurotoxic, and classified as a category 2 reproductive toxicant. It is classified as a suspected endocrine disruptor by ANSES. It is also a category 2 aquatic environment toxicant.

[0008] Alternative solvents to hexane have therefore been tested at laboratory and pilot scale. For example, EP 11 701 288.0 describes the solid / liquid extraction of dehydrated avocados with anhydrous 2-methyloxolane. EP 19 842 832.3 describes the solid / liquid extraction of soybeans, rapeseed, corn, cotton, and sunflower seeds with a binary mixture of 2-methyloxolane and water.

[0009] 2-Methyloxolane is not classified as toxic to the environment and is of bio-based origin because its raw material is typically derived from sugar cane bagasse or corn cobs.

[0010] Furthermore, 2-methyloxolane is non-toxic when ingested at the quantities considered. Indeed, a published 3-month ingestion test on rats showed a no-observed-adverse-effect limit (NOAEL) of 250 mg / kg body weight / day compared to 23 mg / kg body weight / day for hexane (Parris et al. Regulatory Toxicology and Pharmacology 87 (2017) 54-63 and Opinion of the European Scientific Committee on Food published on June 17, 1994). Furthermore, in March 2022 EFSA published a positive opinion for the use of 2-methyloxolane for food extraction (EFSA CEP Panel (EFSA Panel on Food Contact Materials, Enzymes and Processing Aids), Lambre C, Barat Baviera JM, Bolognesi C, Chesson A, Cocconcelli PS, Crebelli R, GottDM, Grob K, Lampi E, Mengelers M, Mortensen A, Riviere G, Steffensen IL, Tlustos C, Van Loveren H, Vernis L, Zorn H, Bignami M, F€urst P, Tard A and Van Haver E, 2022).Scientific Opinion on the safety assessment of 2-methyloxolane as a food extraction solvent. EFSA Journal 2022; 20(3):7138, 23 pp.). .

[0011] The process for producing crude oil and oilcake by solid / liquid extraction using anhydrous 2-methyloxolane is adapted from the conventional process using hexane. In this process, illustrated in [Fig. 1], a biological substrate 1 and anhydrous 2-methyloxolane 2 are introduced into a solid / liquid extractor to undergo a solid / liquid extraction step 3 to obtain separately: - a solvated crude oil 4, also called miscella, comprising 2-methyloxolane and water from the biological substrate 1, and - a solvated oilcake 5, also called pomace, comprising 2-methyloxolane and water from the biological substrate 1.

[0012] The solvated cake is then used in a cake desolvation and solvent recovery step 9, which can, according to a particular embodiment, involve live steam injection, allowing to obtain separately: from the cake 10, a single-phase solvent mixture 11ms, a two-phase mixture of 2-methyloxolane and water 11b, and an aqueous single-phase mixture of 2-methyloxolane and water lima.

[0013] The solvated crude oil is used in an oil desolvation and solvent recovery step 6, which may, according to a particular embodiment, involve live steam injection, allowing to obtain separately: crude oil 7, a single-phase organic mixture of 2-methyloxolane and water 8ms, a second two-phase mixture of 2-methyloxolane and water 8b, and a single-phase aqueous mixture of 2-methyloxolane and water 8ma.

[0014] As illustrated in [Fig. 1], in this process, organic single-phase mixtures, two-phase mixtures, and aqueous single-phase mixtures are combined in a liquid / liquid separation step 12 in a settling tank. Following this liquid / liquid separation step, the following are recovered separately: - a single-phase organic mixture of 2-methyloxolane and water 13, the mass percentage of which is approximately 4.5% water, and - a single-phase aqueous mixture of 2-methyloxolane and water 17 of which the mass percentage of water is approximately 92% at 50°C.

[0015] As illustrated in [Fig.2], the organic monophasic mixture 113 can be reused directly in the solid / liquid extraction step in a process using water-saturated 2-methyloxolane. Alternatively, it can be implemented in a solvent dehydration step 14 to obtain anhydrous 2-methyloxolane or 2-methyloxolane with a water content of less than 4.5% 15 before being reused in the solid / liquid extraction step 3. The vapor condensate from the solvent dehydration forms the stream 16 which joins the liquid / liquid separator 12. The aqueous single-phase mixture 17 from the liquid / liquid separation 12 is implemented in a distillation / condensation step 18 to obtain desolventized wastewater 19 which is discharged or recycled and a two-phase mixture of 2-methyloxolane and water 20b containing about 10.4% water by weight and 89.6% 2-methyloxolane.

[0016] The same process can be adapted to a binary mixture of 2-methyloxolane and water.

[0017] Depending on the mass percentage of water in the binary mixture of 2- Methyloxolane and water, like hexane, can be a single-phase aqueous phase, a single-phase organic phase, or a two-phase phase. Specifically, at equilibrium, the single-phase organic phase contains 4.1 to 4.5% water, and the single-phase aqueous phase typically contains 6 to 21% 2-methyloxolane, depending on its temperature. Unlike hexane, which is only slightly soluble in water, it is therefore not possible to obtain anhydrous 2-methyloxolane after the liquid / liquid separation step in the settling tank, as stream 13 contains approximately 4.5% water, nor is it possible to obtain desolventized wastewater that can be discharged, as the mixture A single-phase aqueous solution 17 still contains 6 to 21% of the single-phase aqueous mixture. It is possible to reuse the organic phase containing approximately 4.5% water directly for the solid / liquid extraction 3, but it may be advantageous to reuse an anhydrous solvent or one with less than 4.5% water. A distillation / condensation step 14 is necessary to obtain anhydrous or less water-rich 2-methyloxolane, which can then be reused in the solid / liquid extraction step 3. These distillation / condensation steps are particularly energy-intensive. The Applicant has calculated that, to obtain anhydrous 2-methyloxolane, these steps consume 314 kWh of heat per tonne of raw material used (the entire calculation is based on soybeans) and 288.5 kWh of cooling per tonne of raw material used in extraction.The wastewater desolventization step consumes an additional 32.1 kWh of heat per ton of raw material used in extraction and 7.85 kWh of cooling per ton of raw material used in extraction. Using a binary mixture containing non-anhydrous but unsaturated 2-methyloxolane (typically containing 3.5% or 4% water instead of 4.5%) reduces the energy consumption associated with these distillation / condensation steps, but it remains significant. Thus, for a mixture of 2-methyloxolane and 1% water by mass, the energy consumption of these steps is 136.8 kWh of heat per ton of raw material used in extraction and 112.9 kWh of cooling per ton of raw material used in extraction. The wastewater desolventization stage consumes an additional 31.7 kWh of heat per tonne of raw material used in extraction and 7.7 kWh of cold per tonne of raw material used in extraction.Using a solvent that is not saturated with water is advantageous for process stability because it remains single-phase. A water-saturated solvent can very easily become two-phase depending on slight temperature variations.

[0018] There is therefore a need to optimize the energy consumption of recycling a solvent comprising 2-methyloxolane intended for the production, by solid / liquid extraction, of a crude oil and a cake.

[0019] Surprisingly, the Applicant has developed a process that meets this need. Summary

[0020] A process for producing a solvent comprising 2-methyloxolane is proposed, said process comprising the following steps: a) collecting a first organic monophasic stream of 2-methyloxolane and water to form a second organic monophasic stream of 2-methyloxolane and water, b) collecting a biphasic stream of 2-methyloxolane and water, c) liquid / liquid separation of the biphasic stream of 2-methyloxolane and water collected in step b) to obtain separately: - a third organic monophasic stream of 2-methyloxolane and water, and - an aqueous monophasic stream of 2-methyloxolane and water, d) mixing of the first organic monophasic stream of 2-methyloxolane and water and the second organic monophasic stream of 2-methyloxolane and water to produce the solvent comprising 2-methyloxolane.

[0021] According to one embodiment, the process according to the invention further comprises a step e) of crude oil desolvation and a step f) of oilcake desolvation upstream of steps a) and b); the step e) of crude oil desolvation producing, from a miscella, a single-phase organic flow of 2-methyloxolane and water and / or a two-phase flow of 2-methyloxolane and water and crude oil; the step f) of oilcake desolvation producing, from a pomace, a single-phase organic flow of 2-methyloxolane and water and / or a two-phase flow of 2-methyloxolane and water and oilcake;the first organic monophasic flow of 2-methyloxolane and water from step a) being a flow produced in step e), a flow produced in step f) or mixtures thereof, preferably a flow produced in step e), and the biphasic flow of 2-methyloxolane and water is a flow produced in step e), a flow produced in step f), or mixtures thereof, preferably a flow produced in step f). ;

[0022] According to one embodiment, the process according to the invention further comprises a step g) of solid / liquid extraction of a biological substrate with a solvent comprising 2-methyloxolane producing the miscella and the marc.

[0023] According to one embodiment, the process according to the invention further comprises a step h) of collecting a second single-phase aqueous stream of 2-methyloxolane and water producing an aqueous phase and a step i) of desolvation of the aqueous phase producing a two-phase stream of 2-methyloxolane and water, the two-phase stream of 2-methyloxolane and water being collected during step b).

[0024] According to one embodiment, the second aqueous monophasic flow of 2-methyloxolane and water is the aqueous monophasic flow of 2-methyloxolane and water obtained in step c), a flow produced during step e) of desolvation of the crude oil, a flow produced during step f) of desolvation of the cake, in particular the aqueous monophasic flow of 2-methyloxolane and water obtained in step c).

[0025] According to one embodiment, step e) of desolvating the miscella comprises the following substeps: el) concentration of crude oil from the miscella to obtain separately - a concentrated miscella, and - the organic monophasic flow of 2-methyloxolane and water, e2) steam stripping of the concentrated miscella to obtain separately: - a solvated crude oil, and - the biphasic flow of 2-methyloxolane and water, e3) purification of the solvated crude oil to obtain the crude oil.

[0026] According to one embodiment, step f) of desolvating the pomace comprises the following substeps: fl) reduction of the solvent content in a pomace to obtain separately: - a partially desolventized marc, and - the biphasic flow of 2-methyloxolane and water or the organic monophasic flow of 2-methyloxolane and water f2) purification of the partially desolventized pomace to obtain the press cake.

[0027] According to one embodiment, step i) of desolvation of the aqueous phase is carried out by distillation of said aqueous phase to obtain separately - the biphasic flow of 2-methyloxolane and water, and - water.

[0028] According to one embodiment, the process according to the invention further comprising a step j) of drying the solvent comprising 2-methyloxolane to obtain anhydrous 2-methyloxolane.

[0029] According to one embodiment, the solvent used in step g) is the solvent comprising 2-methyloxolane obtained in mixing step d), the anhydrous 2-methyloxolane obtained in drying step j), or mixtures thereof, in particular the solvent comprising 2-methyloxolane obtained in mixing step d). Definitions

[0030] For the purposes of this invention, "liquid / liquid separation" means the separation of a two-phase mixture into two distinct phases by means of a static tool, for example, a decanter, or a dynamic tool, for example, a centrifuge.

[0031] For the purposes of the present invention, "solid / liquid extraction" means obtaining a liquid fraction and a press cake, also called a solid residue, from a solid biological substrate using a liquid solvent as the extraction solvent. A liquid / liquid extraction step is not a solid / liquid extraction step within the meaning of the present invention because it does not involve a solid biological substrate; moreover, the physicochemical characteristics involved in a solid / liquid extraction step and in a liquid / liquid extraction step are different.

[0032] For the purposes of the present invention, the term "organic monophasic mixture of 2-methyloxolane and water" means a liquid mixture of 2-methyloxolane and water containing mainly solvent and in which the percentage of water is less than the solubility limit of water in the solvent. This mixture is also referred to as "organic monophasic mixture" in this application.

[0033] For the purposes of the present invention, the term "aqueous monophasic mixture of 2-methyloxolane and water" means a liquid mixture of 2-methyloxolane and water containing primarily water and in which the percentage of solvent is less than the solubility limit of the solvent in water. This mixture is also referred to as "aqueous monophasic mixture" in this application.

[0034] For the purposes of the present invention, a "biphasic mixture of 2-methyloxolane and water" means a liquid mixture of 2-methyloxolane and water comprising an immiscible organic phase and an aqueous phase. This mixture is also referred to as a "biphasic mixture" in this application.

[0035] For the purposes of the present invention, "2-methyloxolane anhydrous" means a methyloxolane comprising less than 3000 mg / kg of water.

[0036] For the purposes of the present invention, "miscella" means a solution of crude oil in a solvent comprising 2-methyloxolane obtained during a solid / liquid extraction step. A miscella comprises 60 to 98%, preferably 70 to 95%, preferably 75 to 93% by weight of solvent comprising 2-methyloxolane relative to the total weight of the miscella and 2 to 40%, preferably 5 to 30%, preferably 7 to 25%, by weight of crude oil relative to the total weight of the miscella. This miscella is also referred to as "solvated crude oil" in the present application.

[0037] For the purposes of the present invention, "concentrated miscella" means a crude oil solution containing 2 to 30%, preferably 5 to 25% by weight of solvent comprising 2-methyloxolane relative to the total weight of the concentrated miscella and 70 to 98%, preferably 75 to 95% by weight of crude oil relative to the total weight of the concentrated miscella.

[0038] For the purposes of the present invention, "desolvent crude oil" means a crude oil solution containing less than 1.5%, preferably less than 1%, preferably less than 0.5%, by mass of residual solvent relative to the total weight of the desolvent crude oil.

[0039] For the purposes of the present invention, "crude oil" means a crude oil solution containing a maximum of 50 mg / kg, preferably a maximum of 10 mg / kg, preferably a maximum of 1 mg / kg of residual solvent relative to the weight of the crude oil.

[0040] For the purposes of the present invention, "pomace" means the solvated solid residue from a solid / liquid extraction comprising 15 to 65%, preferably 20 to 55%, of volatiles by weight relative to the total weight of the pomace and less than 5% residual oil on a dry matter basis. This pomace is also referred to as "solvated press cake" in this application.

[0041] For the purposes of the present invention, "partially desolventized pomace" means the solid residue from a solid / liquid extraction containing less than 5000 mg / kg of residual solvent relative to the total weight of the partially desolventized pomace.

[0042] For the purposes of the present invention, "solvent cake" means the solid residue from a solid / liquid extraction containing less than 1000 mg / kg of residual solvent relative to the total weight of the solvent cake.

[0043] For the purposes of the present invention, "oilcake" means the solid residue from a solid / liquid extraction containing less than 500 mg / kg, preferably less than 100 mg / kg, preferably less than 30 mg / kg of residual solvent relative to the total weight of the oilcake.

[0044] For the purposes of the present invention, "concentration" of the miscella means heating the latter to evaporate most of the solvent it contains and increase its oil content in one or more sub-steps.

[0045] For the purposes of the present invention, "stripping" means an injection of hot gas (for example, live steam) into the concentrated miscella or desolventized oil to heat the liquid and evaporate the residual solvent.

[0046] For the purposes of the present invention, "vacuum drying" means a thermal separation process that removes moisture from a substance at a temperature below 100°C using a vacuum.

[0047] For the purposes of the present invention, "volatiles" means water, solvent or a solvent and water mixture.

[0048] For the purposes of the present invention, "collection" means the storage or gathering of several streams into a single stream. Brief description of the drawings

[0049] Other features, details and advantages will become apparent upon reading the detailed description below, and upon analysis of the accompanying drawings, on which:

[0050] [Fig.1] schematically illustrates the treatment of anhydrous 2-methyloxolane implemented in the prior art solid / liquid extraction process using anhydrous 2-methyloxolane.

[0051] [Fig.2] schematically illustrates the treatment of water-saturated 2-methyloxolane (approximately 4.5% water) implemented in the prior art solid / liquid extraction process using water-saturated 2-methyloxolane (approximately 4.5% water).

[0052] [Fig.3] schematically illustrates one embodiment of the invention.

[0053] [Fig.4] schematically illustrates another embodiment of the invention allowing the production of an anhydrous solvent.

[0054] [Fig.5] represents an equilibrium diagram of the binary liquid mixture of 2-methyloxolane and water. Detailed description of the implementation methods

[0055] The process of the present disclosure is described with reference to [Fig. 3] and [Fig. 4].

[0056] A process for producing a solvent comprising 2-methyloxolane 215 is proposed, said process comprising the following steps: a) collection of a first organic monophasic stream of 2-methyloxolane and water 208ms, 211ms, b) collection of a biphasic stream of 2-methyloxolane and water 208b, 211b, c) liquid / liquid separation of the biphasic stream of 2-methyloxolane and water collected in step b) to obtain separately: - a second organic monophasic stream of 2-methyloxolane and water 213, and - a first aqueous monophasic stream of 2-methyloxolane and water 220, d) mixing of the first organic monophasic stream of 2-methyloxolane and water 227 from the collection of step a) and the second organic monophasic stream of 2-methyloxolane and water 213 from step c) to produce the solvent comprising 2-methyloxolane 215.

[0057] According to one embodiment, the process according to the invention further comprises a step e) of crude oil desolvation and a step f) of oilcake desolvation. The step e) of crude oil desolvation produces, from a miscella 204, a single-phase organic flow of 2-methyloxolane and water 208ms and / or a two-phase flow of 2-methyloxolane and water 208b and crude oil 207. The step f) of oilcake desolvation produces, from a pomace 205, a single-phase organic flow of 2-methyloxolane and water 208ms and / or a two-phase flow of 2-methyloxolane and water 211b and oilcake 210.

[0058] According to one embodiment, the process according to the invention further comprises a step g) of solid / liquid extraction of a biological substrate 201 with a solvent comprising 2-methyloxolane 215 allowing to obtain the miscella 204 and the marc 205

[0059] According to one embodiment, the process according to the invention further comprises a step h) of collecting the aqueous single-phase streams. According to one embodiment, the process according to the invention further comprises a step i) of desolvating the aqueous phase. According to one embodiment, the process according to the invention further comprises a step j) of desolvating the vapors produced by the process. According to one embodiment, the process according to the invention further comprises a step k) of drying the solvent single-phase streams.

[0060] The process according to the invention uses the surprising ability of methyloxolane to release or absorb water upon contact with solid matter in the solid extraction step / The liquid and its miscibility with water decrease as it becomes saturated with oil. Thus, 2-methyloxolane containing 0 to 4.5% water, when placed in the presence of a biological substrate 201 containing 10% water in a countercurrent extractor, can generate a miscella with 20% oil and 1.5 to 2% water. Oil-saturated methyloxolane has lower miscibility with water than 2-methyloxolane not mixed with oil. Any water released by the solvent is absorbed by the biological substrate 201 during extraction. Furthermore, in the case of anhydrous solvent, methyloxolane, while absorbing oil, seeks to absorb moisture to reach 1.5 to 2% water in the miscella. In this case, the solvent then captures some of the free water from the biological substrate 201 to reach its ideal water content.

[0061] The state of the mixture of 2-methyloxolane and water depends on the mass percentage of water in the mixture and the temperature of the mixture.

[0062] A person skilled in the art will be able to determine the state of the binary mixture of 2-methyloxolane and water because the equilibrium diagram of the binary mixture of 2-methyloxolane and water is known (see [Fig. 5]). Different mass percentage values ​​of water delimiting the different states of the binary mixture of 2-methyloxolane and water are also presented in Table 1 below.

[0063] [Tables 1] Temperature | Water Mass Percentage | State of Mixture | 0°C | Greater than or equal to 80% | Aqueous monophasic mixture | Between 4% and 80% | Biphasic mixture | Less than or equal to 4% | Organic monophasic mixture | 9.5°C | Greater than or equal to 82.2% | Aqueous monophasic mixture | Between 4.1% and 82.2% | Biphasic mixture | Less than or equal to 4.1% | Organic monophasic mixture | 19.3°C | Greater than or equal to 85.6% | Aqueous monophasic mixture | Between 4.1% and 85.6% | Biphasic mixture | Less than or equal to 4.1% | Organic monophasic mixture | 29.5°C | Greater than or equal to 88.6% | Aqueous monophasic mixture | Between 4.2% and 88.6% | Biphasic mixture | Less than or equal to 4.2% | Organic monophasic mixture 39.6°C Greater than or equal to 90.8% aqueous single-phase mixture Between 4.3% and 90.8% two-phase mixture Less than or equal to 4.3% organic single-phase mixture 50.1°C Greater than or equal to 92.2% aqueous monophasic mixture Between 4.4% and 92.2% biphasic mixture Less than or equal to 4.4% organic monophasic mixture 60.7°C Greater than or equal to 93.4% aqueous monophasic mixture Between 4.6% and 93.4% biphasic mixture Less than or equal to 4.6% organic monophasic mixture 70.6°C Greater than or equal to 94% aqueous monophasic mixture Between 5% and 94% biphasic mixture Less than or equal to 5% organic monophasic mixture above Boiling point of the azeotrope 2-methyloxolane / water

[0064] According to one embodiment, the mixture of 2-methyloxolane and water used in the process of the present invention is binary, which does not exclude the presence of impurities in the mixture. Solid-liquid extraction

[0065] According to one embodiment, the biological substrate 201 used in step g) is a solid material selected from a plant, an alga, a microorganism, and mixtures thereof, in particular a plant. In a preferred embodiment, the plant, alga, and / or microorganism are recognized as being of food grade or recognized as GRAS (Generally Recognized as Safe).

[0066] When the biological substrate is a plant, then the crude oil obtained according to the process of the invention is called crude vegetable oil.

[0067] For example, the plant may be an oilseed, a protein crop, or a mixture thereof. Examples of oilseeds include rapeseed, sunflower, soybean, peanut, sesame, walnut, almond, cotton, flax, or mixtures thereof, particularly rapeseed, sunflower, soybean, or mixtures thereof. Examples of protein crops include peas (such as the chickpea (Cicer arietinum) or the common pea (Pisum sativum)), broad beans, lupin (genus Lupinus), and mixtures thereof.

[0068] Typically, the biological substrate can be a plant chosen from among almond, amaranth, peanut, argan, sea buckthorn, cashew, avocado, oat, borage, safflower, camelina, carrot, turmeric, chili pepper, annatto, cocoa, cashew, hemp, rapeseed, copra, squash, cotton, croton, rosehip, fig, prickly pear, pomegranate, hops, illipe, jojoba, shea, flax, lupin (genus Lupinus), maize, hazelnut, walnut, coconut, carnation, the marigold, poppy, olive, evening primrose, palm kernel, paprika, pecan, pistachio, pepper, castor bean, rice, rosehip, sesame, soybean, marigold, sunflower, Calophyllum inophyllum, madhuca, Queensland nut, raspberry, blackcurrant, melon, grape, tomato, baobab, babassu, cranberry, chia, pumpkin, mustard, neem, Nigella sativa, niger, poppy, perilla, Plukenetia volubili, pumpkin, annatto, Taramira, apricot, plum, peach, wheat, citrus fruits (such as orange, bergamot, mandarin, grapefruit, lime or lemon), marshmallow, coffee, beetroot, spinach, the bamboo, turmeric, ginkgo, ginseng, matcha tea, milk thistle, moringa, pineapple, broccoli rabe, broccoli, red radish, rosehip, guarana, rosemary, sage, lemongrass, tarragon, thyme, mint, basil, oregano, ajwain or Ajowan, angelica, vetiver,iris, anise, asafoetida or fetid ase, caraway, celery, cardamom, tonka, vanilla, mace, chervil, coriander, cumin, juniper, dill, fennel, dandelion, parsley, Florida palm, grapevine, parsnip and seaweed (Eryngium maritimum), silphium, lettuce, alfalfa, fenugreek (Trigonella foenum-graecum), lentil (Lens culinaris), yerba mate (Ilex paraguariensis), endive, nettle (Urtica dioica), garlic, shallot, leek, chives, Chinese onion, onions, scallions and mixtures thereof, especially soy, rapeseed, sunflower, baobab, corn, peanut, Coconut palm, palm kernel, cotton, especially soybeans, rapeseed, sunflower, baobab, vermicia and mixtures thereof.

[0069] The biological substrate can also be chosen from among rose flowers (Rosa Plathyrhodon, Rosa Hesperhodos, Rosa Hulthemia and Rosa Eurosa, and more particularly Rosa Centifolia and Rosa Damascus), jasmine flowers (jasminum, and more particularly Jasminum grandiflorum and Jasminum sambac), lavender flowers, lavandin flowers (Lavandin stoechas, Lavandula hybrida, Lavandula angustifolia formerly officinalis and Lavandula latifolia, and more particularly Lavandula hybrida abrial, Lavandula hybrida grosso, Lavandula hybrida reydovan, Lavandula hybrida sumian and Lavandula hybrida super), orange blossoms (Citrus sinensis or bitter orange, Citrus aurantium L.), tuberose flowers (Agave polianthes or Polianthes tuberosa), ylang-ylang flowers (Cananga odorata), violet flowers (Viola odorata var.Victoria), et les fleurs de mimosa (fleur d'Acacia dealbata, Acacia decurrens), les tiges et les feuilles de géranium (Pélargonium avec notamment Cicconium, Magnipetala, Parvulipetala, Paucisignata et plus particulièrement Pélargonium graveolens), les tiges et les feuilles de patchouli (Pogostemon cablin et Pogostemon heyanus) et les tiges et les feuilles de petit grain (Citrus aurantium plus particulièrement Citrus aurantium ssp. amara , ou Citrus var. bigaradia , ou Citrus aurantium ssp. Aurantium), les bois de santal (Santalum et plus . particularly Santalum album, Santalum ellipticum, Santalum spicatum), rosewood (Aniba Rosaeodora), cedar rosewood (Cedrus, particularly Cedrus Atlantica and Cedrus Juniperus) and guaiacwood (Bulnesia Sarmienti, Guaiacum officinale and Guaiacum sanctum), spruce needles and twigs, fir spruce needles and twigs (Abies and particularly Abies alba), rosemary spruce needles and twigs (Salvia rosmarinus formerly Romarinus Officinalis), and pine spruce needles and twigs (Pinus and particularly Pinus Sylvestris), resins and balms derived from galbanum (Ferula Galbaniflua or Ferula gummosa), elemi (Canarium and particularly Canarium Commune, Canarium luzonicum, and Canarium indicum), benzoin (Styrax and particularly Styrax Tonkiniensis and Styrax Benzoin), myrrh (Commiphora Myrrha or Commiphora molmol and Commiphora opobalsamum),and frankincense (Boswellia, more specifically Boswellia sacra) and mixtures thereof.

[0070] In the case where the biological substrate is a plant, the solid / liquid extraction step g) can be carried out from the whole plant or from one or more parts of the plant, and in particular a part chosen from the root, stem, bark, flower, seed, germ, leaf, bran, fruit, nut, pips, kernel.

[0071] Depending on the plant, a person skilled in the art will know which part to choose.

[0072] Typically, the biological substrate can be chosen from oat bran, raspberry seeds, blackcurrant seeds, pomegranate seeds, melon seeds, grape seeds, tomato seeds, baobab seeds, babassu seeds, cranberry seeds, chia seeds, corn seeds, cottonseed, peanut seeds, rapeseed, pumpkin seeds, madhuca seeds, mustard seeds, neem seeds, Nigella Sativa seeds, niger seeds, poppy seeds, Perilla seeds, Plukenetia volubili seeds, pumpkin seeds, annatto seeds, rice bran, soybean seeds, Taramira seeds, sunflower seeds, apricot kernels, plum kernels, peach kernels, Calophyllum inophyllum fruit, walnut, Cashew nuts, macadamia nuts, coconut, pecan nuts, and especially soybeans,Rapeseed, sunflower seeds, baobab seeds and mixtures thereof.

[0073] According to a very particular embodiment, the biological substrate is chosen from soybean seeds, rapeseed seeds, sunflower seeds and mixtures thereof.

[0074] When the biological substrate is an alga, it can be chosen from the genera Arthrospira, Haematococcus, Dunaliella (such as Dunaliella salina), Chlorella (such as Chlorella vulgaris, Chlorella sorokiniana, Chlorella zofingensis), Nannochloropsis, Schizochytrium, Crypthecodinium, Culindrotheca, Isochrysis, Nannochloris, Nitzchia, Phaeodactylum, Chaetoceros, Chysophyceae, Xantophyceae, Baccilariophyceae, Dinophyceae, Rodophyceae, Phaeophyceae, Chlorophyceae, Prasinophyceae, Cryptophyceae, Cylindrothec, Botrycoccus, Euglena gracilis, Tetraselmis, Neochloris, Chlorobotrys, Eustigmatos, Phaeodactylum, Porphyridium, Pseudostaurastrum, Tetraselmis, Vischeria, Monodopsis, Ellipsoidion, Pseudocharaciopsis Ascophyllum nodosum; Fucus serratus, F. vesiculosus, Himanthalia elongata, Undaria pinnatifida, Laminaria digitata, L. saccharina, L. japonica, Alaria esculenta, Palmaria palmata (dulse), Porphyra umbilicalis; P. tenera, P. yezoensis, P. dioica, P. purpurea, P. laciniata, P. leucostica, Chondrus crispus; Gracilaria verrucosa, Lithothamnium calcareum, Enteromorpha spp., Ulva spp and their mixtures.

[0075] When the biological substrate is a microorganism, it can be selected from a yeast, a mold, a bacterium, a fungus, or a mixture thereof. The yeast can typically be selected from the genera Cryptococcus, Candida, Lipomyces, Rhodotorula, Saccharomyces, Trichosporon, Yarrowia, and mixtures thereof. The bacterium can be selected from the genera Spirulina (such as Spirulina platensis, Spirulina maxima, also called Arthrospira platensis or Arthrospira maxima), Limnospira (Limnospira platensis), Synechocystis, Nostoc, Cyanothece, Aphanizomenon (such as Aphanizomenon flosaquae), Klamath algae (Aphanizomenon flosaquae), and mixtures thereof.

[0076] According to one embodiment, the biological substrate may have undergone a preliminary preparation step before step g) of solid / liquid extraction. This preparation step may be, for example, flattening, also called flaking, to obtain a flake, grinding, mechanical extraction to obtain a scale, pressing, centrifugation, cooking, freeze-drying, enzymatic lysis, mechanical lysis, maceration, trituration to obtain a cake, ultrasonic treatment, microwave treatment, drying, or any combination of said preparations. Desolvation of crude oil

[0077] According to one embodiment, the process may include a step e) of desolvation of the crude oil aimed at separating the solvent from the crude oil.

[0078] Step e) of desolvating the crude oil can be carried out in several substeps. Each of the described substeps can be carried out in one or more substeps.

[0079] According to one embodiment, step e) of desolvation of the crude oil includes a substep e) of crude oil concentration of the miscella 204. According to one embodiment, substep e) of crude oil concentration of the miscella 204, consisting of at least one concentration stage. According to one embodiment, substep e) of crude oil concentration of the miscella 204, consisting of one concentration stage. According to one embodiment, substep e) of crude oil concentration of the miscella 204, consisting of at least two concentration stages. According to one embodiment, substep e1) of crude oil concentration of miscella 204 consists of two concentration stages. According to one embodiment, substep e1) of crude oil concentration of miscella 204 brings the concentrated miscella to a residual solvent level of 2 to 30% by mass. According to one embodiment, substep e1) of crude oil concentration of miscella 204 brings the concentrated miscella to a residual solvent level of 5 to 25% by mass. According to one embodiment, substep e1) of crude oil concentration of miscella 204 brings the concentrated miscella to a residual solvent level of 1 to 20% by mass.

[0080] In one embodiment, the concentration operation is carried out in a single step, i.e., using a single heat exchange column. In another embodiment, the concentration operation is carried out in two substeps, i.e., using two successive heat exchange columns. In one embodiment, the heat exchange column is an evaporation column. In another embodiment, when two successive heat exchange columns are used, the first column reduces the residual solvent in the concentrated miscella to less than 30% by mass, preferably 25% by mass, preferably 20% by mass, and the second column reduces the residual solvent content in the concentrated miscella from 1% to 5% by mass, preferably to 1% by mass.

[0081] According to one embodiment, step e) of desolvating the crude oil includes a substep e2) consisting of at least one stripping with live steam injection. Substep e2) reduces the amount of residual solvent in the crude oil to less than 1.5% by mass, preferably less than 1%, preferably less than 0.5%. According to an alternative embodiment, step e) of desolvating the crude oil includes a substep e2') consisting of at least one stripping with strong steam injection. Substep e'2) reduces the amount of residual solvent in the wet crude oil to less than 1.5% by mass, preferably less than 1%, preferably less than 0.5%.

[0082] According to one embodiment, step e) of desolvating the crude oil includes a substep e3) consisting of at least one vacuum drying step to reduce the amount of residual water in the crude oil to less than 1000 mg / kg, preferably less than 500 mg / kg, preferably less than 200 mg / kg. According to another embodiment, step e) of desolvating the crude oil includes a substep e3) consisting of at least two vacuum drying steps to reduce the amount of residual water in the crude oil to less than 1000 mg / kg, preferably less than 500 mg / kg, preferably less than 200 mg / kg.

[0083] According to one embodiment, step e) of desolvation of the crude oil may comprise the following substeps: el) concentration of crude oil from miscella 204 by heating and then condensation of the solvent vapors to obtain separately - a concentrated miscella, and - the organic single-phase flow of 2-methyloxolane and water 208ms, e2) live steam stripping of the concentrated miscella to obtain separately: - a desolventized crude oil, and - the biphasic flow of 2-methyloxolane and water 208b, e3) Vacuum drying of the crude oil to obtain crude oil 207 and stream 208b.

[0084] According to one embodiment, the miscella 204 contains from 2 to 40% by mass of oil, preferably from 5% to 30%, preferably from 7 to 25%. According to one embodiment, the concentrated miscella contains from 70% to 98%, preferably from 70% to 95%, preferably from 75% to 95% by mass of oil. According to one embodiment, the desolventized crude oil contains less than 1.5% by mass of residual solvent, preferably less than 1%, preferably less than 0.5%. According to one embodiment, the crude oil contains a maximum of 50 mg / kg of residual solvent, preferably a maximum of 10 mg / kg, preferably a maximum of 1 mg / kg, and a maximum of 1000 mg / kg, preferably a maximum of 500 mg / kg, preferably a maximum of 200 mg / kg of water.

[0085] According to an alternative embodiment, step e2) can be replaced by step e2') described below.

[0086] e2') Steam stripping of the concentrated miscella with strong steam injection for obtain separately: - a moist crude oil, and - the single-phase aqueous flow 208mA,

[0087] According to one embodiment, the wet crude oil contains less than 50 mg / kg, preferably less than 10 mg / kg, preferably less than 1 mg / kg of residual solvent relative to the total weight of the wet crude oil.

[0088] Step e) of desolvation of a crude oil produces a single-phase organic stream of 2-methyloxolane and water 208ms and / or a two-phase stream of 2-methyloxolane and water 208b and crude oil 207. Desolvation of the oilseed cake

[0089] According to one embodiment, the process may include a step f) of desolvation of the cake aimed at separating the solvent from the solid residue (also called cake) 10. According to a particular embodiment, step f) may include cooking the cake (toasting) and adjusting its water content.

[0090] According to one embodiment, step f) of desolvating the oilseed cake can be carried out in a DT-DC (Desolvator-Toaster-Dryer-Cooler), one or more tower-shaped tools fed with oilseed cake at the top, discharged at the bottom, and composed of superimposed chambers heated indirectly in certain chambers of the tool. According to one embodiment, the superimposed chambers are heated indirectly by injecting steam counter-currently to the oilseed cake.

[0091] According to an alternative embodiment, step f) of desolvation of the cake can be carried out in two steps: a desolvation step with superheated solvent followed by a vacuum drying step with or without live steam injection. According to one embodiment, the desolvation step with superheated solvent is carried out in a tool called a flash desolventizer.

[0092] According to one embodiment, step f) of desolvating the oilseed cake may include the following substeps: fl) reduction of the solvent content in a pomace 205, to obtain separately: - a partially desolventized pomace, and - a biphasic flow of 2-methyloxolane and water 211b or a monophasic organic flow of 2-methyloxolane and water 211ms; f2) purification of the partially desolventized pomace to obtain the press cake.

[0093] When the desolvation of a cake involves the injection of live steam, the condensed vapors form the biphasic stream of 2-methyloxolane and water 211b. When the desolvation of a cake is carried out without the addition of live steam, the vapors, once condensed, form a monophasic organic stream of 2-methyloxolane and water 211ms.

[0094] According to one embodiment, the partially desolventized pomace obtained at the end of step fl) contains less than 5000 mg / kg of residual solvent.

[0095] According to one embodiment, step f2) of purifying the partially desolventized pomace consists of a drying step to adjust the moisture content of the press cake and a cooling step to obtain the press cake. According to one embodiment, step f2 can generate a single-phase aqueous flow 211ma.

[0096] According to an alternative embodiment, step f) of desolvation of the cake may comprise the following substeps: fl') reduction of the solvent content in a 205 marc, by indirect heating to obtain separately: - a partially desolventized marc, and - vapors which, once condensed, form a single-phase solvent flow of 2-methyloxolane and water 211ms; f2') A desolvation and toasting step with indirect heating and live steam injection to obtain a desolvated cake and vapors forming after condensation a single-phase aqueous flow 211ma or a two-phase flow 211b depending on the quantity of steam injected;

[0097] f3') a drying step;

[0098] f4') optionally, a cooling step.

[0099] According to one embodiment, the drying step f3') allows the moisture content to be adjusted to approximately 10% by mass.

[0100] According to one embodiment, the cooling step f4') makes it possible to obtain the cake with less than 500 mg / kg of solvent, preferably less than 100 mg / kg, preferably less than 30 mg / kg, and approximately 10% moisture and less than 40°C in temperature. This step can generate a single-phase aqueous flow 211 mA.

[0101] According to the process of the invention, step f) of desolvation of cake produces a single-phase organic flow of 2-methyloxolane and water 211ms and / or a two-phase flow of 2-methyloxolane and water 211b and cake 210. Collections

[0102] According to the process of the invention, organic single-phase mixtures, two-phase mixtures and aqueous single-phase mixtures are not implemented in a single settling tank for phase separation.

[0103] According to the process of the invention, the organic single-phase mixtures are directed towards the collection 223 and the two-phase mixtures are directed towards a collection 224. According to one embodiment, the aqueous single-phase mixtures are directed towards a collection 225.

[0104] The process according to the invention comprises a step a) of collecting a first single-phase organic stream of 2-methyloxolane and water 208ms, 211ms

[0105] According to one embodiment, the first organic single-phase stream of 2-methyloxolane and water is a 208ms stream produced during step e) of desolvation of a crude oil, a 211ms stream produced during step f) of desolvation of a cake, or mixtures thereof. According to another embodiment, the first organic single-phase stream of 2-methyloxolane and water may be a 208ms stream produced during step e) of desolvation of a crude oil, a 211ms stream produced during step f) of desolvation of a cake, a 222ms stream produced during step j) of desolvation of the other vapors of the process, or mixtures thereof. According to a preferred embodiment, the first organic single-phase flow of 2-methyloxolane and water is a 208ms flow produced during step e) of desolvation of a crude oil.

[0106] The process according to the invention includes a step b) of collecting a biphasic stream of 2-methyloxolane and water 208b, 211b.

[0107] According to one embodiment, the two-phase flow of 2-methyloxolane and water collected in step b) is a flow 208b produced during step e) of desolvation of a crude oil, a flow 211b produced during step f) of desolvation of a cake, a flow 222b produced during step g) of desolvation of other vapors of the process, a flow 220b produced during step h) of desolvation of an aqueous phase or mixtures thereof. According to one embodiment, the biphasic flow of 2-methyloxolane and water is a flow 208b produced during the desolvation step e) of a crude oil, a flow 211b produced during the desolvation step f) of a cake, a flow 220b produced during the desolvation step h) of an aqueous phase or mixtures thereof.According to one embodiment, the biphasic flow of 2-methyloxolane and water is a flow 208b produced during the desolvation step e) of a crude oil, a flow 211b produced during the desolvation step f) of a meal, or mixtures thereof. According to one embodiment, the biphasic flow of 2-methyloxolane and water is a flow 211b produced during the desolvation step f) of a meal.

[0108] The process according to the invention includes a step h) of collecting a single-phase aqueous stream of 2-methyloxolane and water.

[0109] The aqueous single-phase flow of 2-methyloxolane and water (220, 208ma, 211ma, 222ma) can be the aqueous single-phase flow of 2-methyloxolane and water 220 obtained in step c), a 208ma flow produced during step e) of desolvation of crude oil, a 211ma flow produced during step f) of desolvation of oilcake, a 222ma flow produced during step j) of desolvation of other vapors of the process, in particular the aqueous single-phase flow of 2-methyloxolane and water 220 obtained in step c). The liquid / liquid separation steps c), substep e2) of stripping the solvated oil 208ma and the desolvation of the vapors 222ma can also generate single-phase aqueous flows which can feed the collection 225. The impact of these flows in the process of the present invention is negligible.

[0110] According to one embodiment, the aqueous phase 226 contains from 1 to 8% by mass of solvent, depending on the process organization, preferably from 1 to 5%. Liquid / liquid separation

[0111] The process according to the invention comprises a step c) of liquid / liquid separation of the biphasic stream of 2-methyloxolane and water collected in step b) to obtain separately a second organic monophasic stream of 2-methyloxolane and water 213, and a first aqueous monophasic stream of 2-methyloxolane and water 220. According to one embodiment, the aqueous monophasic phase from the liquid / liquid separation step is directed towards the collection 225.

[0112] The process according to the invention also includes a step d) of mixing the first organic monophasic stream of 2-methyloxolane and water 227 from the collection of step a) and the second organic monophasic stream of 2-methyloxolane and water 213 from step c) to produce the solvent comprising 2-methyloxolane 215. Desolvation of the aqueous phase

[0113] According to one embodiment, the process may further include a step i) of desolvation of an aqueous phase 226 having the objective of recovering the solvent and purifying the aqueous effluent before discharge or recycling said effluent into the process.

[0114] According to one embodiment, the aqueous single-phase mixtures from the collection 225 are sent to a desolvation step of the aqueous phase i) via the stream 226. According to one embodiment, the desolvation step of the aqueous phase i) can be carried out in an aqueous effluent distillation column.

[0115] Step i) of desolvation of the aqueous phase 226 can be carried out by distillation of said aqueous phase 226 to obtain separately, after condensation of the distillation vapor, a two-phase stream of 2-methyloxolane and water 220b, and water 219. Desolvation of the other vapors of the process

[0116] According to one embodiment, the process may further include a step j) of desolvation of the other vapors of the process having the objective of recovering the solvent still contained in these vapors and the purification of the gaseous effluents before their release into the atmosphere.

[0117] In one embodiment, the tools (e.g., extractors, condensers, etc.) to be kept under negative pressure are connected to a vapor desolvation device 221 before release into the atmosphere. In one embodiment, this device consists of a scrubbing tower into which the vapors are injected at the bottom of the column and encounter a liquid counter-current which, in the case of 2-methyloxolane, may be composed, for example, of oil or water. In one embodiment, the liquid counter-current is composed of oil. In another embodiment, the liquid counter-current is composed of water.

[0118] Step j) can be carried out in various embodiments.

[0119] According to one embodiment, step j) of desolvation of the remaining vapors from the process can be carried out using an oil scrubber. The oil can be injected counter-currently with the vapors to become saturated with solvent. It can then be heated to evaporate the solvent, which can then be condensed for recovery. According to one embodiment, step j) uses a gas scrubber tower employing mineral oil. The mineral oil is injected counter-currently with the gas and captures the solvent. The oil is then heated to evaporate the solvent, which, once condensed, generates a 222ms flow. The oil can then be cooled and recycled in the scrubbing tower.

[0120] According to an alternative embodiment, the washing tower uses water. The solvent-laden water generates a 222ma flow which joins the collection of aqueous single-phase flows 225. The aqueous single-phase flows 225 can then be sent to step i) of aqueous phase desolvation via flow 226. Step j) of desolvation of the remaining vapors can be carried out using a water scrubber. Water can be injected counter-currently to the vapors to become solvent-laden. In this case, the recovered 222ma flow can be directed directly or via the collector 225 to the aqueous phase desolvation step i). Solvent drying

[0121] According to [Fig.4], the process according to the invention may further include a step k) of drying the solvent comprising 2-methyloxolane 215 to obtain anhydrous 2-methyloxolane 228.

[0122] The solvent drying step 215 can be carried out, for example, by distillation. In this case, a new two-phase flow is generated after vapor condensation, 227b, which is directed towards the separator 225.

[0123] In the process according to the invention, the solvent used in step g) can be the solvent comprising 2-methyloxolane 215 obtained in step d) of mixing, the anhydrous 2-methyloxolane 228 obtained in step k) of drying, preferably the solvent comprising 2-methyloxolane 215 obtained in step d) of mixing. Examples

[0124] The ChemCad® process simulator version 7.1.8. (Chemstations, 2019) was used for the comparative simulations.

[0125] Example 1 according to the invention.

[0126] A process simulation was performed using ChemCad® software version 7.1.8 (Chemstations, 2019). The process flow diagrams that were simulated are those described in [Fig. 1] (without the flow separation invention) and in [Fig. 3] (with flow separation according to the invention). Both simulations assume continuous extraction and a process without thermal integration. The results are given for the following raw material: 1 tonne of soybeans with 20% oil. The solvent / raw material ratio is 1:1. [Tables 2 Target water percentage in recycled solvent: 0.03% 1% 3.16% Without the invention With the invention Gain Without the invention With the invention Gain Without the invention With the invention Gain Thermal consumption (kW / T soybean) without thermal integration: 567, 511 (10%), 392, 344 (12%), 323, 282 (13%). Cooling requirement (kW / T soybean) without thermal integration: -581, -523 (10%), -407, -357 (12%), -337, -295 (12%).

Claims

Demands

1. A process for producing a solvent comprising 2-methyloxolane (215), said process comprising the following steps: a) collecting a first organic monophasic stream of 2-methyloxolane and water (208ms, 211ms), b) collecting a biphasic stream of 2-methyloxolane and water (208b, 211b), c) liquid / liquid separation of the biphasic stream of 2-methyloxolane and water collected in step b) to obtain separately: - a second organic single-phase flow of 2-methyloxolane and water (213), and - a first single-phase aqueous flow of 2-methyloxolane and water (220), d) mixing the organic monophasic stream of 2-methyloxolane and water (227) from the collection in step a) and the second organic monophasic stream of 2-methyloxolane and water (213) from step c) to produce the solvent comprising 2-methyloxolane (215).

2. A process according to claim 1, further comprising a step e) of crude oil desolvation and a step f) of oilcake desolvation upstream of steps a) and b), step e) of crude oil desolvation producing, from a miscella (204), a single-phase organic stream of 2-methyloxolane and water (208ms) and / or a two-phase stream of 2-methyloxolane and water (208b) and crude oil (207); step f) of desolvation of oilseed cake producing, from a pomace (205), a single-phase organic flow of 2-methyloxolane and water (208ms) and / or a two-phase flow of 2-methyloxolane and water (211b) and oilseed cake (210); the first organic monophasic flow of 2-methyloxolane and water (208ms, 211ms) of step a) being a flow produced during step e), a flow produced during step f) or mixtures thereof, preferably a flow produced during step e), and the biphasic flow of 2-methyloxolane and water (208b, 211b) is a flow produced during step e), a flow produced during step f), or mixtures thereof, preferably a flow produced during step f).

3. A process according to claim 2, further comprising a step g) of solid / liquid extraction of a biological substrate (201) with a solvent comprising 2-methyloxolane (215) producing miscella (204) and marc (205).

4. A method according to any one of claims 2 and 3 further comprising a step h) of collecting a second single-phase aqueous stream of 2-methyloxolane and water (220, 208ma, 21 Ima) producing an aqueous phase (226) and a step i) of desolvation of the aqueous phase (226) producing a two-phase stream of 2-methyloxolane and water (220b), the two-phase stream of 2-methyloxolane and water (220b) being collected during step b).

5. A process according to claim 4 wherein the second aqueous single-phase stream of 2-methyloxolane and water (220, 208ma, 21 Ima) is the aqueous single-phase stream of 2-methyloxolane and water (220) obtained in step c), a stream (208ma) produced during step e) of desolvation of the crude oil, a stream (21 Ima) produced during step f) of desolvation of the cake, in particular the aqueous single-phase stream of 2-methyloxolane and water (220) obtained in step c).

6. A process according to any one of claims 2 to 5 wherein the step e) of desolvating the miscella comprises the substeps: e1) crude oil concentration of the miscella (204) to obtain separately - a concentrated miscella, and - the organic monophasic stream of 2-methyloxolane and water (208ms), e2) steam stripping of the concentrated miscella to obtain separately: - a solvated crude oil, and - the biphasic stream of 2-methyloxolane and water (208b), e3) purification of the solvated crude oil to obtain the crude oil.

7. A process according to any one of claims 2 to 6 wherein step f) of desolvating the pomace comprises the substeps: fl) reducing the solvent content in a pomace (205) to obtain separately: - a partially desolvated pomace, and - the biphasic flow of 2-methyloxolane and water (211b) or the organic monophasic flow of 2-methyloxolane and water (211ms), f2) purification of the partially desolventized pomace to obtain the press cake.

8. A process according to any one of claims 4 to 7 wherein step i) of desolvation of the aqueous phase (226) is carried out by distillation of said aqueous phase (226) to obtain separately - the biphasic stream of 2-methyloxolane and water (220b), and - water (219).

9. A process according to any one of claims 1 to 8 further comprising a step j) of drying the solvent comprising 2-methyloxolane (215) to obtain anhydrous 2-methyloxolane (228).

10. A process according to claim 9 wherein the solvent used in step g) is the solvent comprising 2-methyloxolane (215) obtained in step d) of mixing, the anhydrous 2-methyloxolane (228) obtained in step j) of drying, or mixtures thereof, in particular the solvent comprising 2-methyloxolane (215) obtained in step d) of mixing.

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