Reduction of glucosinolate antinutrionals in oilseed meal

Abstract

A process of reducing the glucosinolate content in oilseed meal is disclosed. The oilseed meal is derived from Camelina sativa. The oilseeds are conditioned to degrade some of the glucosinolates. The conditioned oilseeds are pressed to expel oil from the seeds. The press cake fraction of the oilseed is extracted with hexane, desolventized and toasted to reduce the glucosinolate content. Defatted meals with low glucosinolate content made by the process are also described.

Description

Docket No.: PT-2225-WO-PCTREDUCTION OF GLUCOSINOLATE ANTINUTRIONALS IN OILSEED MEALCROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of U.S. Provisional Application No.63 / 736,770, filed December 20. 2024, which is incorporated by reference herein in its entirety. %BACKGROUND

[0002] The development of new oilseed feedstock crop for biofuels (e.g. ethanol, biodiesel, bio-jet fuel), bio-industrial uses (e.g., bioplastics, lubricants) and specialty fatty acids (e.g., erucic acid) has been an area of interest. The members of the Brassicaceae family are of interest not only because of their potential for providing a high-quality feedstock oil but also because of their ability' to be grown sustainably in many regions of the world. The dry oilseeds are crushed, and oil is extracted, providing meals that can be used in animal feeds. The meals from oilseeds can be modified to alter the composition of some antinutritional factors.

[0003] Camelina sativa (camelina) is a flowering plant in the family Brassicaceae usually known as camelina, gold-of-pleasure, or false flax, but also occasionally as wild flax, linseed dodder, German sesame, or Siberian oilseed. It is native to Europe and areas of Central Asia, but cultivated as an oilseed crop mainly in Europe and in North America. Camelina products are used as animal feed, functional food, biodiesel, and pharmaceuticals. Camelina seed, oil, and defatted meal have been widely used for different applications and are, therefore, critical crop commodities for many industries.

[0004] Camelina has been approved as a cattle feed supplement in the US, as well as an ingredient (up to 10% of the ration) in broiler chicken feed and laying hen feed. Camelina meal, the byproduct of camelina when the oil has been extracted, has a significant crude protein content. Feeding camelina meal can significantly increase omega-3 -fatty' acid concentration in both breast and thigh meat of turkeys. Camelina oil has also been investigated as a spring lipid source to fully replace fish oil in diets for farmed Atlantic salmon, rainbow trout, and Atlantic cod.

[0005] However, various antinutritional factors are present in camelina oil meal and can affect its use as livestock feed. The use of camelina meal for animal feed is limited by the presence of glucosinolates. Camelina seeds contain glucosinolates (GSL), phytates, tannins and sinapine, in addition to non-starch polysaccharides and oligosaccharides. These minor components need to be below a certain threshold in order to use the defatted meal in feed.Docket No.: PT-2225-WO-PCTSUMMARY

[0006] The present disclosure provides a process for producing a oilseed meal with low levels of glucosinolates. The process contains conditioning oilseed material at a temperature of at least 60°C. The oilseed material comprises oilseeds and / or oilseed flakes from the Brassicaceae family. The conditioning inactivates the myrosinase enzyme in the oilseed material and degrades a portion of glucosinolates in the oilseed material. The process further comprises pressing the conditioned oilseed material to separate the oilseed material into an oil fraction and a cake fraction. The process further includes treating the cake fraction with a solvent comprising hexane to extract residual oil and generate a defatted cake. The process further comprises desolventizing-toasting (DT) the defatted cake to remove residual hexane and generate a defatted meal. The DT step further degrades the glucosinolates. The defatted meal comprises a total glucosinolate content of less than 25 pmol per gram of meal by dry weight. The oilseeds may be from Camelina saliva.

[0007] The conditioning may further comprise adding moisture to the oilseed material. The conditioning may be conducted for a duration of 10 minutes and 50 minutes. The conditioning and pressing reduces the glucosinolate content, wherein the glucosinolate content of the cake fraction may be reduced by between about 5% and about 25% relative to the glucosinolate content in the oilseed material prior to conditioning. The total glucosinolate content of the defatted meal may be less than 25 pmol per g of defatted meal. The moisture content of the defatted meal may be 20% or less. The oilseed material may be conditioned at a temperature in the range of 75°C to 100°C. The DT step may be performed at a temperature of at least 70°C. The DT step is performed at a temperature between 75°C to 115°C. The DT reduces the glucosinolate content by at least 20wt% relative to the glucosinolate content in the defatted cake prior to DT. The DT step comprises a period of greater than 40 minutes. The glucosinolate content of the defatted meal is 10% or less relative to the glucosinolate content of the oilseeds. The level of hexane in the defatted meal is less than 200ppm. The process may further comprise flaking the oilseeds to produce oilseed flakes prior to conditioning. The process may further comprise diying / cooling the defatted meal to a moisture content of 12% or less, wherein the defatted meal comprises a total glucosinolate content of less than 25 pmol per gram of meal.

[0008] The disclosure also provides a defatted meal of Camelina saliva oilseed.

[0009] The disclosure also provides an animal feed additive comprising a defatted meal produced from Camelina saliva oilseed, wherein the defatted meal comprises less than 25 pmol total glucosinolates per gram of meal with a moisture content less than 12wt% and an oil content of less than 5wt%, dry weight, and a protein content of less than 45wt%, dry weight. The defattedDocket No.: PT-2225-WO-PCT meal may comprise less than 25 pmol of total glucosinates per gram of meal with a moisture content less than 12wt% and an oil content of less than 5wt%, dry weight, and a protein content of less than 50wt%, dry weight.

[0010] The present disclosure provides a process for producing a meal from oilseeds with low crude fiber content. The process contains conditioning oilseed material at a temperature of at least 60°C. The oilseed material comprises oilseeds and / or oilseed flakes from the Brassicaceae family. The conditioning inactivates the myrosinase enzyme in the oilseed material and degrades a portion of crude fiber content in the oilseed material. The process further comprises pressing the conditioned oilseed material to separate the oilseed material into an oil fraction and a cake fraction. The process includes further treating the cake fraction with a solvent comprising hexane to extract residual oil and generate a defatted cake. The process further comprises desolventizing-toasting (DT) the defatted cake to remove residual hexane and generate a defatted meal. The DT step further degrades the crude fiber content. The defatted meal comprises a crude fiber content of less than 20wt% of the defatted meal. The oilseeds may be from Camelina saliva.

[0011] The conditioning may further comprise adding moisture to the oilseed material. The conditioning may be conducted for a duration of 10 minutes and 50 minutes. The conditioning and pressing reduces the crude fiber content, wherein the crude fiber content of the cake fraction is reduced by at least about 10wt% relative to the crude fiber content in the oilseed material prior to conditioning. The total crude fiber content of the defatted meal is less than 20wt% of the defatted meal after drying and cooling the defatted meal. The moisture content of the defatted meal may be 15wt% or less. The oilseed material may be conditioned at a temperature in the range of 75° C. to 100° C. The DT step may be performed at a temperature of at least 70°C. The DT step is performed at a temperature between 75° C to l l5° C. The DT reduces the crude fiber content by at least 20wt% relative to the crude fiber content in the defatted cake prior to DT. The DT step comprises a period of greater than 40 minutes. The crude fiber content of the defatted meal is 30% or less relative to the crude fiber content of the oilseeds. The level of hexane in the defatted meal is less than 200ppm. The process may further comprise flaking the oilseeds to produce oilseed flakes prior to conditioning. The process may further comprise drying / cooling the defatted meal to a moisture content of 12% or less, wherein the defatted meal comprises a crude fiber content of less than 15wt% of the defatted meal after dry ing and cooling.

[0012] The disclosure also provides an animal feed additive comprising a defatted meal produced from Camelina saliva oilseed, wherein the defatted meal comprises less than 15wt% of total crude fiber with a moisture content less than 12wt% and an oil content of less than 5wt%,Docket No.: PT-2225-WO-PCT dry weight, and a protein content of at least 30wt%, dry weight. The defatted meal may comprise a crude fiber content of less than 12wt% of the defatted meal after drying and cooling, with a moisture content less than 12wt% and an oil content of less than 5wt%, dry weight, and a protein content of less than 50wt%, dry weight.

[0013] The disclosure also provides for a feed ration comprising the animal feed additive. The feed ration may be suitable for ruminant livestock, monogastric livestock, or poultry livestock. The feed ration may be formulated to maximize weight gain and meat quality of beef cattle in the feed lot, or to maximize milk production of lactating dairy cattle.BRIEF DESCRIPTION OF THE DRAWINGS

[0014] The drawings illustrate generally, by way of example, but not by way of limitation, various aspects discussed herein.

[0015] FIG. 1 shows a schematic diagram of an exemplary’ process for generating the Camelina saliva meal with low glucosinolate levels.

[0016] FIG. 2 shows a schematic diagram of desolventizing / toasting apparatus.DETAILED DESCRIPTION

[0017] Reference will now be made in detail to certain aspects of the disclosed subject matter, examples of which are illustrated in part in the accompanying drawings. While the disclosed subject matter will be described in conjunction with the enumerated claims, it will be understood that the exemplified subject matter is not intended to limit the claims to the disclosed subject matter.

[0018] This disclosure relates to an animal feed additive compnsing a defatted meal with low levels of total glucosinolates (GSL). The total GSL can be less than 25umol, or less than 20umol, or less than 15umol, or less than lOumol of total GSL per gram of the meal. The defatted meal also comprises a crude fiber content of at most about 20wt%, or at most about 18wt%, or at most about 16wt%. The defatted meal is produced from oilseeds. The oilseeds can be from the Brassicaceae family. In one aspect, the defatted meal is produced from Camelina saliva. This disclosure also relates to a process for producing a defatted meal from oilseeds, e.g. Camelina saliva, having a low content of GSL and low crude fiber. The method can include a step of conditioning and expelling oil from the seeds. The method also includes a step of extracting oilseed material with hexane and desolventizing-toasting (DT) the resulting oilseed material. TheDocket No.: PT-2225-WO-PCT conditioning step and the DT step can reduce the GSL content and the crude fiber content in the defatted meal.

[0019] The term “animal feed” as used herein refers to processed formulations that are fed to livestock, e.g., cattle, poultry', fish and the like. Animal feeds may be formulated to provide optimum nutrition for applications, e.g., maximizing weight gain and meat quality of beef cattle in the feed lot, maximizing milk production of lactating dairy cattle and the like.

[0020] The term “oilseed” as used herein refers to any crop species where oil is extracted from the seeds of these grains for food or industrial purposes, and includes Brassicaceae oilseeds such as canola, and non-Brassicaceae oilseeds, such as flaxseed, soybean, safflower, and sunflower. An example of a crop species that is used primarily in the production of industrial feedstock oil is Camelina sativa.

[0021] The term “oilseed material” as used herein refers to oilseeds and / or oilseed flakes.

[0022] The term “cake” or “pressed cake” or “full-fat cake” as used herein refers to the remaining fraction of the seed content after it has gone through the flaking and cooking / conditioning stage and has been mechanically pressed to extrude the bulk of the oil. The term refers to the physical character of the meal at this stage, which has been compressed into a cake-like mass rich in protein and can still contain appreciable residual oil. For the present invention, the cake can be derived from any process that extracts oil from oilseeds, leaving the cake. These terms will be used interchangeably.

[0023] The term “defatted cake” as used herein refers to a solvent extracted full-fat cake. The full fat cake is solvent extracted, e.g., with hexane, to remove residual oil.

[0024] The term “meal” or “defatted meal” as used herein refers to defatted cake after it has been treated in the desolventizer / toaster. These terms will be used interchangeably.

[0025] The term “glucosinolates” or “GSL” as used herein refers to P-thioglucoside N- hydroxy sulfates with a variable side chain (R) and a sulfur-linked 0-d-glucopyranose moiety. They represent a large and heterogeneous family of naturally occurring compounds. Glucosinolates have the following chemical structure:

[0027] The R groups are classified as aliphatic, aromatic, -methylthioalkyl, and heterocyclic (indole). Tissue compartmentalization has evolutionarily separated the chemicallyDocket No.: PT-2225-WO-PCT and thermally stable glucosinolates and their hydrolytic enzyme myrosinase, a beta thioglucosidase.

[0028] In Camelina sativa, the glucosinolate profile has been examined, and the main glucosinolates are found to be the following aliphatic glucosinolates: 9-(Methylsulfinyl)nonyl glucosinolate (also known as glucoarabin or GS9), 10-(Methylsulfmyl)decyl glucosinolate (also known as glucocamelinin or GS10), and 1 l-(Methylsulfinyl)undecyl glucosinolate (also known as homoglucocamelinin or GS11). Upon tissue disruption during mechanical processing, myrosinase can immediately react with glucosinolates. The hydrolytic degradants from glucosinolates are isothiocyanates (ITCs), which have the potential to induce anticarcinogenic effects by enhancing antioxidant potential and can ameliorate nonalcoholic fatty liver diseases by decreasing the level of lipid peroxidation in cells and tissues. Glucosinolates taste bitter and pungent to humans, chicken, fish, and pigs and can reduce feed intake and lead to growth retardation in finishing pigs when their content is higher than 15 umol / g in canola meal.

[0029] The term "crude fiber content” as used herein refers to the indigestible fiber present in the sample, fraction and / or defatted meal. The crude fiber content is the indigestible carbohydrate in the meal. The crude fiber content includes mainly cellulose and can also include hemicellulose and lignin.

[0030] The term "‘anti-nutritional factors” or “ANF” refers to a number of compounds found in oilseed meals that reduce the nutritional benefit of animal feed products in which the meal is used as an additive. Glucosinolates and isothiocyanates are classified as ANFs since they can impart a bitter and pungent taste to the feed ration w hen present in high enough concentrations resulting in reduced palatability and reduced intake of the meal.

[0031] Method for processing oilseeds

[0032] In one aspect, the present description relates to a method for producing a defatted meal with low levels of glucosinolates (GSL). The method can also produce a defatted meal with a low level of crude fiber. The defatted meal can be derived from a variety of oilseeds. The oilseeds can be from oilseed feedstock crop for biofuels (e.g. ethanol, biodiesel, bio-jet fuel), bio-industrial uses (e.g., bioplastics, lubricants) and specialty fatty acids (e.g., erucic acid). The oilseeds can be from crops from the members of the Brassicaceae family, for example, mustard seeds, rapeseeds and the like. The members of the Brassicaceae family can include, for example, members from the genus Brassica. Camelina, Crambe, Thlaspi, Sinapis, Raphanus and the like. The oilseeds used in the methods described herein can include oilseeds from, for example, Brassica carinata (Ethiopian mustard), Brassica napus (canola), Brassica juncea, Camelina sativa (FalseDocket No.: PT-2225-WO-PCT flax), Thlaspi arvense (pennycress), Crambe abyssinica (Crambe), Sinapis alba, Brassica rapa, Raphamis sativus (radish) and the like. Crops that provide a high-quality feedstock oil and have the ability7to be grow n sustainably may be used to produce the defatted meal described herein.

[0033] In one aspect, the oilseeds are from Camelina sativa, referred to herein as Camelina oilseeds. The present method will be described in the context of Camelina oilseeds and producing Camelina defatted meal, but it will be understood that other oilseeds can be used in the methods described herein to produce defatted meals with low GSL.

[0034] In one aspect, the method can include cleaning the oilseeds. Generally , oilseeds are harvested from the Camelina crops and cleaned. Cleaning may include separating weed seeds, grain seeds, leaves, dust, sand, earth pieces, stones, prods, sticks, metal, and other extraneous impurities from the oilseeds before storing. The oilseeds, preferably, enter the crushing plant with no more than 5wt%, preferably no more than 4wt%, preferably no more than 3wt%, preferably no more than 2wt%, preferably no more than 1.8wt% foreign materials in the oilseeds. The cleaning process may include removing dust and light material, for example, by aspiration, sieving and the like. The amounts of pods, fines, loose hulls can be minimized in the oilseeds.

[0035] In one aspect, the method comprises maximizing the removal of the pods from the oilseeds. The removal of pods from the oilseeds can be increased using finer screens to remove more of the pods. The pods contain high levels of crude fiber and minimizing the pods content in the oilseeds can reduce the crude fiber content in the oilseeds that are processed and thus, the defatted meal generated using the methods described herein. The oilseeds, preferably, enter the crushing plant w ith no more than 5wt%, preferably no more than 4wt%, preferably no more than 3wt%. preferably no more than 2wt%, preferably no more than 1.8wt% of pods in the oilseeds.

[0036] In one aspect, the oilseed matenal may be preheated prior to other processing steps. Preheating may be performed to heat the oilseeds to between about 30°C and about 90°C, or between about 30°C and about 80°C, or between about 30°C and about 70°C, or between about 30°C and about 60°C, or between about 30°C and about 50°C, or between about 30°C and about 40°C. The preheating can be performed for less than 10 minutes, or less than 5 minutes, or less than 4 minutes, or less than 3 minutes, or less than 2 minutes. The preheated seeds are more easily pliable and thus less probable to shatter during the flaking and / or conditioning steps. Preheating may be conducted, for example, in bed heaters using w arm air or direct steam. Externally heated rotary kilns may also be used for seed heating. Other methods of heating may be used and are also within the scope of this description.Docket No.: PT-2225-WO-PCT

[0037] In one aspect, the method may, optionally, include generating oilseed flakes from oilseeds in a flaker. The oilseeds may be flaked after preheating as described above. The oilseeds may be flaked prior to or after conditioning as described herein. The oilseeds may be flaked if the oilseeds are larger, e.g. greater than about 2mm. Oilseeds seeds larger than 2mm, or larger than 4mm, or larger than 5mm, may be flaked in a flaker. The method may include preheating the cleaned oilseeds prior to processing the oilseeds through a flaker to generate Camelina flakes.

[0038] A variety of methods are known in the art for generating oilseed flakes from oilseeds and all are within the scope of this description. The method can comprise generating oilseed flakes by introducing the oilseeds into a flaking apparatus (flaker). The oilseeds may or may not be conditioned prior to flaking. Flaking can be applied to rupture the seed coat and to flatten the cotyledons. Flaking can enhance the oil output during processing. Flakers are known in the art. A process for flaking, crushing and refining oilseeds is described, for example, by Unger, E.H. “Processing" in Canola Chemistry, Production, Processing, and Utilization, p. 163- 188, 2011. The cleaned and optionally, conditioned, oilseeds can be crushed, for example, in a roller mill to generate flakes. The flakes can be, for example, between about 0.2 and 0.5mm in thickness, or between about 0.25 and 0.45, or betw een about 0.3-0.4mm, or between about 0.3 and 0.38 mm in thickness. The pressure to obtain the flakes can be, for example, between 500 and 750psi.

[0039] In one aspect, the oilseed material comprises fine oilseeds. Fine oilseeds may be used in the methods described herein without flaking. The oilseeds can be conditioned and further processed as described herein without being subject to a flaking step. If the cleaned seeds are fine oilseeds, the flaking step can be eliminated, and the cleaned fine oilseeds can be conditioned as described herein. Fine oilseeds are oilseeds that are less than or 3 mm, or less than 2 mm, or less than 1 mm may be conditioned as oilseeds. The method may not include a flaking step if the oilseeds are about 2mm or less. In one aspect, a flaking step may be eliminated prior to conditioning and / or pressing.

[0040] In one aspect, the amount of moisture in the incoming oilseed material, e.g., the oilseed entering the process described herein, can vary and may be based on plant configurations and the level of dr ing prior to processing. The seed moisture content may be at least 2wt%, or at least 5wt%, or at least 7wt% by controlling the airflow. The seed moisture content can be less than 15wt%, or less than 12wt%, or less than 10wt% by controlling the airflow. The seed moisture content can be between about 2wt% and 15wt%, or between 5wt% and about 10wt%, or between about 7wt% and l lwt%, or between about 7wt% and 10wt% by controlling the airflow. In oneDocket No.: PT-2225-WO-PCT aspect, the seed moisture can be in a range of 7.0 to 9.0 wt% when entering a flaking and / or conditioning step. Other moisture ranges are also within the scope of this description.

[0041] In one aspect, the method comprises conditioning the oilseed material. “Conditioning” as used herein refers to treating the oilseed material to optimize expelling the oil from the oilseed material in the expeller. Conditioning the oilseed material can include, for example, heating the oilseed material to a selected temperature for a duration of time. The moisture content of the oilseed material may be adjusted during conditioning / heating. Conditioning the oilseed material can also include adding moisture to the oilseed material in the conditioner. Moisture can include the addition of water and / or steam.

[0042] In one aspect, the method can include conditioning the oilseed material in the presence of added moisture in the conditioner. The method can include adding water and / or steam to the oilseed material in the conditioner to a desired moisture. The moisture content in the conditioner can be at least 2wt%, or at least 5wt%, or at least 7wt% by weight of the oilseeds. The moisture content in the conditioner can be less than 15wt%, or less than 12wt%. or less than 10wt% by weight of the oilseeds. The moisture content in the conditioner can be between about 5wt% and I 5wt%. or between 5 t% and about 10wt%, or between about 7wt% and I 5wt%. or between about 7wt% and 10wt% by weight of the oilseeds. In one aspect, the moisture content in the conditioner can be in a range of 7.0 to 9.0 wt% when entering a flaking and / or conditioning step. Other moisture ranges are also within the scope of this description.

[0043] The method can further comprise conditioning the oilseed material by heating. The heating may use direct heating and / or indirect heating. Preferably, the oilseed material is indirectly- heated in cookers. Indirect heating can include, for example, contacting the oilseed material with a hot surface. In one aspect, indirect heated can include the use of steam-heated tubes packed around the internal wall of the drum inside the conditioner as the conditioner heats the oilseed material.

[0044] In one aspect, the oilseed material can be conveyed to a heated drum where the oilseed material is conditioned by cooking at elevated temperatures. The oilseed material may- be heated, for example, to at least about 50°C, or at least 60°C, or at least 70°C, or at least 75°C. The oilseed material may be heated to no more than 150°C, or no more than 125°C, or no more than 110°C, or no more than 105°C, or no more than 100°C. The oilseed material may be heated to between about 50°C and about 150°C, or between about 60°C and about 110°C, or between about 50°C and about 100°C, or between about 80°C and about 95°C, or between 80°C and 100°C, or between about 85°C and about 95°C, or between 85°C and 100°C, or between 90°C and 100°C, orDocket No.: PT-2225-WO-PCT between about 90°C and about 95°C. The oilseed material can be indirectly heated to reduce or control the moisture content of the flake or seeds to pressing. In one aspect, the oilseed material is heated to temperature greater than 50°C to inactivate the myrosinase activity. Preferably, the oilseed material is heated quickly through the temperature range between 40°C and 50°C, the active temperature range for myrosinase.

[0045] The oilseed material may be conditioned for at least 5 min, or at least 10 min, or at least 15 min, or at least 20 minutes. The oilseed material may be conditioned for up to 60 minutes, or up to 40 min, or up to 30 minutes, or up to 25 minutes. The oilseed material may be conditioned for between 5 and 60 min, or between 10 and 50 minutes, or 10 and 40 minutes, or between 10 and 30 minutes, or between 15 and 50 minutes, or between 15 and 40 minutes, or between 15 and 30 minutes, or between 15 and 25min, or between 15 and about 20 minutes, or between 20 and 50 minutes, or between 20 and 40 minutes.

[0046] Without being bound by any theory, it is thought that heating the oilseed material in the conditioner can reduce oil viscosity bound to the seeds thereby promoting coalescence of oil droplets. This can increase the diffusion rate of hexane solvent into the pressed cake during the solvent extraction process. Heating can also contribute to the inactivation of enzymes such as myrosinase and lipase. The conditioning can include treating the oilseed material at the conditioning parameters, e.g.. moisture, heat. time, as described herein to inactivate the enzymes, e.g., myrosinase.

[0047] In one aspect, the oilseed material is conditioned to substantially or completely inactivate the myrosinase enzyme activity. By substantially, it is meant that at least 70% of the myrosinase activity, or at least 80%, or at least 90%, or at least 95%, or at least 98%, or at least 99% of the myrosinase enzyme activity' is eliminated compared to the myrosinase activity in the oilseed material prior to conditioning.

[0048] In one aspect, the oilseed material is conditioned to substantially or completely inactivate the lipase activity. By substantially, it is meant that at least 70% of the lipase activity, or at least 80%. or at least 90%, or at least 95%, or at least 98%, or at least 99% of the lipase activity is eliminated compared to the lipase activity in the oilseed material prior to conditioning.

[0049] In one aspect, the conditioning of the oilseed material can reduce the GSL content in the oilseed material. The GSL content of the oilseed material can be reduced by at least about 2%, or at least about 5%, or at least about 10%, or at least about 15%, or at least about 20% relative to the GSL content in the oilseed material prior to conditioning. The GSL content of the oilseed material can be reduced by at most 20%, or at most 15%, or at most 10%, or at most 5% relativeDocket No.: PT-2225-WO-PCT to the GSL content in the oilseed material prior to conditioning. The GSL content of the oilseed material can be reduced by between about 2% and about 25%, or between about 2% and about 20%, or between about 5% and about 25%, or between about 5% and about 20%, or between about 5% and about 15%, or between about 5% and about 10%, or between about 10% and about 15% relative to the GSL content in the oilseed material prior to conditioning.

[0050] In one aspect, the conditioning of the oilseed material can reduce the crude fiber content in the oilseed material. The crude fiber content of the oilseed material can be reduced by at least about 5%, or at least about 10%, or at least about 15%, or at least about 20% relative to the crude fiber content in the oilseed material prior to conditioning. The crude fiber content of the oilseed material can be reduced by at most 50%, or at most 30%, or at most 20%, or at most 10% relative to the crude fiber content in the oilseed material prior to conditioning. The crude fiber content of the oilseed material can be reduced by between about 5% and about 40%, or between about 5% and about 30%, or between about 10% and about 40%, or between about 10% and about 30%, or between about 15% and about 40%, or between about 15% and about 30% relative to the crude fiber content in the oilseed material prior to conditioning.

[0051] In one aspect, the method further comprises pressing the conditioned oilseed material in an expeller. The conditioned oilseed material may be pressed in a large screw press expeller. In one aspect, the pressing can remove oil from the oilseed material to generate an oil fraction and a cake fraction. Cake fraction may also be referred to herein as pressed cake or full fat cake. In one aspect, the pressing can remove at least about 30wt% of the oil, or at least about 40wt% of the oil, or at least about 50wt% of the oil, or at least about 60wt% of the oil in the oilseed material. The pressing may remove between about 30wt% to 80 wt%, or between about 30wt% to 70 wt%, or between about 40wt% to 70 wt%, or between about 50wt% to 70wt% of the oil content in oilseed material.

[0052] In one aspect, the expeller / press may, for example, contain a screw that is enclosed in a cage formed by longitudinal bars, held by a heavy frame. The screw can squeeze the oilseed material across bars. The bars can be separated by metallic spacers to allow the oil to flow between the bars while the squeezed cake or pressed cake can be discharged to the extraction plant. Pressed oil will have some footing that may be extruded with the oil while pressing. These footings may be separated by setting and centrifuge. The heavy phase can be returned and mixed back with the feed of the press while the high phase (clarified pressed oil) can go to storage.

[0053] In one aspect, the method further comprises treating the press cake fraction with hexane in a solvent extractor. The cake fraction can be treated with hexane as the solvent to extractDocket No.: PT-2225-WO-PCT residual oil from the cake fraction. A variety of solvent extractors are known in the art and can be used to treat the cake fraction with hexane. The extractor can be, for example, a continuous belt extractor that can move the cake fraction and the mixture (hexane plus oil) in opposite directions to achieve a continuous counter current extraction. Series of pumps move the mixture over the cake, so that the mixture with the highest concentration in oil is used to extract the entering cake fraction with the highest concentration in oil. At the opposite extremity of the extractor, pure hexane washes the cake fraction w ith the lowest concentration of oil.

[0054] In one aspect, the cake fraction is extracted with solvent that can range between pure hexane and a mixture comprising hexane and oil. The mixture can comprise between about 10 and 40wt% of oil, or between about 20 to 30wt% of oil, or between about 20 and 25wt% of oil. Solvent / mixture percolates through the cake or submerges it, allowing the diffusion of the oil contained in the cake into the liquid phase. After leaving the solvent extractor, the resulting end cake is a defatted cake.

[0055] The defatted cake can include about 3wt% oil or less, 2wt% oil or less, or lwt% oil or less, 0.8wt% or less, or 0.6wt% oil or less, or 0.5wt% oil or less, or 0.4wt% oil or less. The defatted cake can include between about 0.5 and 3wt% oil, or between about 0.5wt% and 2.5 wt% oil, or between about 0.5wt% and 2wt% oil, or between about 1.0wt% and 3wt% oil, or between about l.Owt % and 2.5wt% oil, or between about l.Owt % and 2.0wt% oil.

[0056] The residual mixture (hexane / oil) separated from the defatted cake can include at least about 10wt% oil, or at least about 15 4% oil, or at least about 20wt% oil, or at least about 25wt% oil, or at least about 30wt% oil. The residual mixture (hexane / oil) separated from the defatted cake can include about 90wt% hexane or less, or 85 wt% hexane or less, or about 80wt% hexane or less, or about 75wt% hexane or less, or about 70wt% hexane or less. The residual mixture (hexane / oil) separated from the defatted cake can include 10-20wt% oil and 90-80wt% hexane, 15-25wt% oil and 85 to 75wt% hexane, or 20-30 wt% oil and 80 to 70 wt% hexane. The hexane can be removed by evaporation and stripping from the oil in the residual mixture to make extracted oil. This extracted oil can be mixed with the pressed oil to make a crude oil that is a combination of pressed and extracted oil.

[0057] In one aspect, the method further comprises desolventizing-toasting (DT) the defatted cake to remove the residual hexane and generate a defatted meal. The DT of the defatted cake can degrade the GSL and result in reducing and / or eliminating the GSL in the defatted material. In one aspect, the DT step of the defatted cake can degrade the crude fiber and result in reducing and / or eliminating the crude fiber content in the defatted material.Docket No.: PT-2225-WO-PCT

[0058] After the solvent extraction, the defatted cake can be transferred to a desolventizer- toaster, where it is heated. The DT step can remove remaining hexane, reduce GSL content and reduce the moisture content of the defatted cake. Most of the solvent is removed by heating the defatted cake on steam-heated plates. Removal of the final traces of solvent is carried out by injecting steam through the defatted cake. Injecting steam through the defatted cake can also toast the defatted cake.

[0059] DT can be conducted in an apparatus having a variety of configurations and all are within the scope of this description. Desolventization in the DT can remove the solvent held in the extracted cake by means of evaporation and steam stripping. In one aspect, the DT apparatus can be a closed vessel with two or more zones. The zones can include a pre-desolventization zone, high desolventization zone(s), toasting zone, stripping zone, cooling zone and the like. Other zones may also be present in the DT apparatus that enhance the DT process.

[0060] In one aspect, the DT apparatus can include a vertical stack of cylindrical gas-tight pans that can be steam heated from the base. FIG. 2 is one exemplary DT apparatus configuration. Other DT apparatus with other configurations may also be used and are within the scope of this description. Starting from the top of the DT, the extracted defatted cake can be spread on tray one where it is equally distributed by means of a sweep arm. From there, the cake can be moved continuously from tray to tray through tray openings. Each of the toasting trays can have hollow punches for venting vapors from one tray to the next. Direct steam is sparged in the DT by the bottom tray and moved upward from tray-to-tray resulting in stripping hexane from the cake.

[0061] The main trays can be used for toasting the product. Main trays are perforated trays that can provide the steam. They are designed to provide both indirect heating and direct steam contact to remove the bulk of the solvent from the defatted extracted cake. The added steam can carry the evaporated hexane and get condensed in external condenser and returned to the hexane / water separator to separate the hexane from water. The hexane phase may be recycled and reused back in the extractor.

[0062] Desolventizing and toasting generates a defatted meal with the hexane solvent reduced and / or eliminated. The DT step also lowers the moisture content in the defatted meal exiting the DT step. In one aspect, DT step can be conducted at a temperature of at least 80°C, or at least 90°C, or at least 100°C, or at least 105°C. The DT step can be conducted at a temperature between about 80°C and about 110°C, or between about 80°C and about 105°C, or between 80°C and 100°C, or between 85°C and I I0°C, or between 85°C and 105°C, or between 85°C and I00°C, or between about 90°C and 110°C, or between 90°C and 105°C, or between 90°C and about 100°C,Docket No.: PT-2225-WO-PCT or between 95°C and about 110°C, or between 95°C and about 105°C, or between 95°C and about 100°C, or between 100°C and about 110°C, or between about 100°C and 105°C.

[0063] The DT step can be conducted for at least 30 minutes, or at least 35 minutes, or at least 40 minutes, or at least 45 minutes, or at least 60 minutes. The DT step can be conducted for at most 120 minutes, or at most 90 minutes, or at most 60minutes, or at most 55 minutes, or at most 50 minutes, or at most 45 minutes. The DT step can be conducted for between about 30 minutes and about 120 minutes, or about 30 minutes and about 90 minutes, or between about 30 minutes and about 80 minutes, or between about 30 minutes and about 70 minutes, or about 30 minutes and 60 minutes, or between about 45 minutes and 90 minutes, or between about 45 minutes and about 80 minutes, or between about 45 minutes and 70 minutes, or between about 45 minutes and 65 minutes, or between about 45 minutes and 60 minutes, or between about 50 minutes and 90 minutes, or between about 50 minutes and 80 minutes, or between about 50 minutes and 70 minutes, between about 55 minutes and 65 minutes.

[0064] In one aspect, the DT may also include adding gum and / or soap stock out of an oil refining process to the extracted defatted cake prior to or in the DT. The soap stock may be added to add calories and / or to increase the nutritional value of the defatted meal to the health of the animal. In one aspect, the soap stock may be camelina soap stock, a byproduct of refining camelina oil. The content of the gum (out of degumming process) and / or soap stock (out of the caustic refining process) can be about 50 % oil and about 50 % concentrated phospholipids or soap of fatty7acid. The composition of the soap stock can be, for example, 20 % oil, 20 % soap / gums, and 60 % water. Soap stock with other composition may also be used. The DT step can also dry the defatted cake to further remove the hexane and moisture form a defatted meal.

[0065] The DT step performed on the defatted cake can generate a defatted meal. The defatted meal can have a moisture content of less than 20wt% of moisture in the defatted meal, or less than 15wt%, or less than 13wt%, or less than 10wt%, or less than 81x4% of moisture in the defatted meal. The defatted meal can have a moisture content of between about 5wt% and about 25wt%, or between about 5wt% and about 20wt%, or between about 10wt% and about 25wt% or between about 10wt% and about 20wt%.

[0066] The defatted meal can have a hexane content of lOOOppm or less, or 800ppm or less, or 600ppm or less, 500ppm or less, 400ppm or less, 300ppm or less, 200 ppm or less, or lOOppm or less. The defatted meal can have a hexane content of between lOOppm and lOOOppm, or between lOOppm and 800ppm, or between lOOppm and 600ppm, or between lOOppm and 500ppm, or between 200ppm and lOOOppm, or between 200ppm and 800ppm, or between 200ppmDocket No.: PT-2225-WO-PCT and 600ppm, or between 200ppm and 500ppm, or between 300ppm and lOOOppm, or between 300ppm and 800ppm, or between 300ppm and 600ppm, or between 300ppm and 500ppm, or between 400ppm and lOOOppm, or between 400ppm and 800ppm, or between 400ppm and 600ppm, or between 400ppm and 500ppm.

[0067] The GSL content and the crude fiber content in the defatted cake can be further degraded during the DT step to generate defatted meal with lower GSL content and lower crude fiber content. The DT step can reduce the GSL content in the defatted meal by at least 20%, or at least 30%, or at least 40%, or at least 50% relative to the GSL content in the whole oilseed. The DT step can reduce the GSL content in the defatted meal by between 20% and 80%, or between 20% and 70%, or between 20% and 60%, or between 30% and 80%, or between 30% and 70%, or between 30% and 60%, or between 40% and 80%, or between 40% and 70%, or between 40% and 60% relative to the GSL content in the whole oilseed.

[0068] The DT step can further reduce the crude fiber content in the defatted meal relative to the whole oilseed. The DT step can reduce the crude fiber content in the defatted meal by at least 10%, or at least 15%, or at least 20%, or at least 25% relative to the crude fiber content in the whole oilseed. The DT step can reduce the crude fiber content in the defatted meal by between 10% and 50%, or between 15% and 50%, or between 15% and 40%, or between 15% and 30%, or between 20% and 50%, or between 20% and 40%, or between 20% and 30%, relative to the crude fiber content in the whole oilseed.

[0069] The DT step may further comprise cooling the defatted meal. The temperature of the defatted meal exiting the DT can be about 80°C or lower, or about 70°C or lower, or about 65°C or lower. The temperature of the defatted meal exiting the DT can be between about 50°C and about 80°C, or between about 50°C and about 75°C, or between about 50°C and about 65°C, or between about 50°C and about 60°C, or between about 55°C and about 75°C, or between about 55°C and about 65°C, or between about 60°C and about 70°C.

[0070] The defatted meal exiting the DT can be further cooled and dried in a drier / cooler. The moisture content of the defatted meal can be reduced after the drying and cooling. The defatted meal after the drying and cooling may be cooled to temperature of less than 40°C, or less than 35°C, or less than 30°C. The defatted meal may be cooled to a temperature of between 20 and 40°C, or between 20 and 35°C, or between 20 and 30°C, or between 25 and 4-°C, or between 25 and 35°C after the drying and cooling. The moisture content of the defatted meal after drying and cooling can be less than 20wt%, or less than 18wt%, or less than 15wt%, or less than 12wt% based on the weight of the defatted meal. The moisture content of the defatted meal after dryingDocket No.: PT-2225-WO-PCT and cooling can be between about 10wt% and 20wt%, or between about 10wt% and 18wt%, or between about 10wt% and 15wt%, or between about 10wt% and 12wt%, or between about 5wt% and 15\\ t%. or between about 5wt% and 12wt%, or between about 5wt% and 10wt% based on the weight of the defatted meal.

[0071] The defatted meal generated after the drying and cooling step can include a total GSL content of less than 22umol / gm of defatted meal, or less than 20umol / gm, or less than 15umol / gm, or less than 10 umol / gm, or less than 5umol / gm of meal. The defatted meal generated after the DT step can include a total GSL content of between 2 and 22 umol / gm of defatted meal, or between 2 and 20 umol / gm, or between 2 and 15 umol / gm. or between 2 and 10 umol / gm, or between 5 and 20 umol / gm, or between 5 and 15 umol / gm, or between 5 and 10 umol / gm.

[0072] The defatted meal generated after the dry i ng and cooling step can include a crude fiber content of less than 25wt%, or less than 20wt%, or less than 17wt%, or less than I5wt%. or less than 12wt%. The defatted meal generated after the drying and cooling step can include a crude fiber content of between 10wt% and 25wt%, or between 10wt% and 20wt%, or between 10wt% and 15\\t%.

[0073] During the dr ing and cooling step, further residual hexane can be removed to lower the concentration of the hexane in the defatted meal. The concentration of the hexane can be less than 200ppm, or less than 150 ppm. or less than 100 ppm, or less than 50ppm, or less than 25ppm. The dried and cooled defatted meal can have a hexane content of between lOppm and 200ppm, or between lOppm and 150ppm, or between lOppm and lOOppm, or between lOppm and 75ppm, or between lOppm and 50 ppm, or between lOppm and 25ppm, or between 25ppm and 200ppm, or between 25ppm and lOOppm, or between 25ppm and 75ppm, or between 25ppm and 50ppm.

[0074] The moisture content in the dried meal can also be reduced to less than 20wt%, or less than 15 vvt%. or less than 12wt%, or less than 10wt%. The moisture content in the dried meal can be between 5wt% and 20wt%, or between 5wt% and 15wt%, or between 5wt% and 10wt%, or between 10wt% and 20wt%. or between 10wt% and 15wt%, or between 10wt% and 12wt%.

[0075] In one aspect, the methods described herein for generating the defatted meal do not include the use of exogenous myrosinase enzyme. The GSL content in the defatted meal is not significantly or at all reduced by the activity' of the myrosinase enzyme.

[0076] The methods described herein reduce the GSL content during more than one step. In one aspect, the GSL content in the oilseeds is reduced during the conditioning step and the DT step. The defatted meal generated by methods described herein can have reduced GSL contentDocket No.: PT-2225-WO-PCT compared to the GSL content in the whole oilseeds due to the advantageous degradation of the GSL in the conditioning and the DT step. The method can reduce the GSL content in the defatted meal by at least 20%, or at least 30%, or at least 40%, or at least 50%, or at least 60%, or at least 70%, or at least 80%. or at least 90% compared to the GSL content in the whole oilseed. The method can reduce the GSL content in the defatted meal by at between 20% and 90%, or between 20% and 80%, or between 20% and 70%, or between 20% and 60%, or between 30% and 90%, or between 30% and 80%, or between 30% and 70%, or between 30% and 60%, or between 40% and 90%, or between 40% and 80%, or between 40% and 70%, or between 40% and 60%, or between 50% and 90%, or between 50% and 80%, or between 50% and 70%, or between 50% and 60%, or between 60% and 90%, or between 60% and 80%, or between 60% and 70% compared to the GSL content in the whole oilseed.

[0077] The methods described herein reduce the crude fiber content during more than one step. In one aspect, the crude fiber content in the oilseeds is reduced during the conditioning step and the DT step. The defatted meal generated by methods described herein can have reduced crude fiber content compared to the crude fiber content in the whole oilseeds due to the advantageous degradation of the crude fiber content in the conditioning and the DT step. The method can reduce the crude fiber content in the defatted meal by at least 20%, or at least 30%, or at least 40%. or at least 50%. or at least 60%, compared to the crude fiber content in the whole oilseed. The method can reduce the crude fiber content in the defatted meal by at between 20% and 80%, or between 20% and 70%, or between 20% and 60%, or between 30% and 80%, or between 30% and 70%, or between 30% and 60%, or between 40% and 80%, or between 40% and 70%, or between 40% and 60%, or between 50% and 80%, or between 50% and 70%, or between 50% and 60%, or between 60% and 80%, or between 60% and 70% compared to the GSL content in the whole oilseed.

[0078] In one aspect, Fig. 1 shows a schematic flow diagram for a process of generating defatted meal with low total GSL levels and low crude fiber content. The process comprises cleaning the oilseeds. The oilseeds may be flaked in a flaker as described above. The oilseeds and / or the flakes may be conditioned. Conditioning can include injection of steam and / or water. Conditioning can include heating the oilseed material. The conditioned oilseed material can be transferred to an expeller. The expeller can separate the oil fraction from the cake fraction. The oil fraction can be further processed to separate any solids from the oil. The oil can be transferred to storage and any solids may be reintroduced into the expeller.Docket No.: PT-2225-WO-PCT

[0079] The cake fraction can be transferred to an extractor to remove the residual oil in the cake. Hexane can be introduced into the extractor and the cake can be permeated with the hexane as described above. The hexane / oil mixture can be removed from the extractor and further separated by distillation into hexane and oil. The extracted and now defatted cake can be transferred to a DT apparatus. Steam, and optionally gum or soap stock, can be added to the DT apparatus to reduce and / or remove the hexane in the defatted cake. The DT apparatus can also reduce the moisture content in the defatted cake to form a defatted meal. The defatted meal can be further processed by transferring to a dryer / cooler to further remove hexane traces and reduce the moisture content. The dried meal may be further ground and / or sifted prior to storage.

[0080] In one aspect, the present disclosure relates to a process for producing a meal from oilseeds comprising: a. conditioning oilseed material by cooking the oilseed material to a temperature of at least 60°C, wherein the oilseed material comprises oilseed flakes and fine oilseeds and wherein the conditioning inactivates the myrosinase enzyme and wherein the conditioning degrades a portion of glucosinolates in the oilseed material; b. pressing the oilseed material to remove oil from the oilseed material and producing an oil fraction and a cake fraction; c. treating the cake fraction with a solvent comprising hexane to extract residual oil to generate a defatted cake fraction; and d. desolventizing-toasting (DT) the defatted cake fraction to remove residual hexane and further degrade the glucosinolates and generate a defatted meal, wherein the defatted meal comprises a moisture content of 20% or less and a total glucosinolate content of less than 25 pmol per gram of meal, wherein the oilseeds are from the Brassicaceae family.

[0081] In one aspect, the present disclosure relates to a process for producing a meal from oilseeds comprising:

[0082] a. conditioning oilseed material at a temperature of at least 60°C, wherein the oilseed material comprises oilseeds and / or oilseed flakes, wherein the conditioning inactivates the myrosinase enzyme in the oilseed material and degrades a portion of the crude fiber content in the oilseeds;

[0083] b. pressing the conditioned oilseed material to separate the oilseed material into an oil fraction and a cake fraction;

[0084] c. treating the cake fraction with a solvent comprising hexane to extract residual oil and generate a defatted cake; andDocket No.: PT-2225-WO-PCT

[0085] d. desolventizing-toasting (DT) the defatted cake to remove residual hexane and generate a defatted meal, wherein the DT further degrades the crude fiber content and wherein the defatted meal comprises a total crude fiber content of less than 15% by weight;

[0086] wherein the oilseeds are from the Brassicaceae family.

[0087] In one aspect, the methods described herein do not include the addition of exogenous myrosinase enzyme. The degradation of the glucosinolates by myrosinase is minimized or eliminated in the methods described herein.

[0088] In one aspect, the methods described herein can degrade glucosinolates. The glucosinolates can include 9-(Methylsulfinyl) nonyl glucosinolate (GS9), 10-(Methylsulfmyl)decyl glucosinolate (GS10), l l-(Methylsulfinyl)undecyl glucosinolate (GS11) and the like. The methods may degrade at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%, or at least 95% of the GS9 present in the oilseeds. The methods may degrade at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%, or at least 95% of the GS 10 present in the oilseeds. The methods may degrade at least 50%, or at least 60%, or at least 70%, or at least 80%, or at least 90%, or at least 95% of the GS11 present in the oilseeds. Composition of Defatted Meal

[0089] In one aspect, the present description comprises an animal feed additive, wherein the animal feed additive comprises the defatted meal. The defatted meal can be derived from oilseeds.

[0090] Preferably, the defatted meal is from oilseeds from the members of the Brassicaceae family , for example, mustard seeds, rapeseeds and the like. The members of the Brassicaceae family can include, for example, members from the genus Brassica, Camelina, Crambe. Thlaspi, Sinapis, Raphanus and the like. The members of the Brassicaceae family can include, for example, Brassica carinata (Ethiopian mustard), Brassica napus (canola), Brassica juncea, Camelina sativa (False flax), Thlaspi arvense (pennycress), Crambe abyssinica (Crambe), Sinapis alba, Brassica rapa, Raphanus sativus (radish) and the like.

[0091] The GSL content in the oilseeds used to produce the defatted meal can be less than 30umol of GSL / g of oilseed, or less than 28umol of GSL / g of oilseed, or less than 25umol of GSL / g of oilseed. The GSL content of the oilseeds can be greater than 22umol / g of oilseed, or greater than 24umol / g of oilseeds.

[0092] The defatted meal, after drying and cooling, can have a moisture content of less than 20wt% of the meal, or less than 15wt% of the meal, or less than 10wt% of the meal, or less than 8wt% of the meal. The defatted meal has moisture content of between about 5wt% andDocket No.: PT-2225-WO-PCT20wt%, or 6wt% and 15wt%, or 6wt% and 13wt% of the meal, or between 8wt% and 15wt%, or between 8wt% and 12wt%.

[0093] The defatted meal produced according to the methods described herein advantageously has a low GSL content. By low, it is meant that the GSL content is less than 25umol / g of defatted meal, dry weight. Preferably, the GSL content of the defatted meal is less than about 20umol / g of defatted meal, or less than 15umol / g of the defatted meal, or less than lOumol / g of the defatted meal, or less than 9umol / g, or less than 8umol / g, or less than 7umol / g, or less than 6 umol / g, dry weight. The GSL content of the defatted meal can be between 2 and 20 umol / gm, or between 2 and 15 umol / gm, or between 2 and 10 umol / gm, or between 5 and 20 umol / gm, or between 5 and 15 umol / gm, or between 5 and 10 umol / gm.

[0094] The defatted meal, after drying and cooling, produced according to the method described herein comprises a crude fiber content of less than 25wt%, or less than 20wt%, or less than 17wt%, or less than 15wt%, or less than 12wt%. The defatted meal can include a crude fiber content of between 10wt% and 25wt%, or between 10wt% and 20wt%, or between 10wt% and 15wt%.

[0095] The defatted meal, after dry ing and cooling, produced according to the methods described herein comprises oil content of less than 5wt%, dry weight, or less than 4wt%, or less than 3.5wt%, or less than 3wt%, or less than 2wt%, dry weight. The defatted meal produced according to the method described herein comprise oil content of between about lwt% and about 5wt%, or between lwt% and about 4wt%, or between lwt% and 4wt%, or between 2wt% and 4wt%, or between about lwt% and about 3.5wt%, dry7weight.

[0096] The defatted meal, after drying and cooling, produced according to the method described herein comprises protein content of at least 30wt%, or at least 35wt%, or at least 40wt%, dry weight. The defatted meal produced according to the method described herein comprises protein content of between 30wt% and 50wt%, or between 35 \\t% and 45wt%, or between 40wt% and 43wt%.

[0097] In one aspect, the present description relates to a feed ration comprising an animal feed additive, wherein the animal feed additive includes the defatted meal described herein. The feed ration can be suitable for ruminant livestock, monogastric livestock, fish and / or poultry livestock. The ruminant livestock can be cattle. The feed ration can be formulated to maximize weight gain and meat quality of beef cattle in the feed lot and / or to maximize milk production of lactating dairy cattle. The monogastric livestock can be swine.Docket No.: PT-2225-WO-PCT

[0098] In one aspect, the feed ration can further comprise the defatted meal. The feed ration comprises the defatted meal at an amount of at least 5wt% of the feed ration, or at least 6wt%, or at least 7wt%, or at least 8wt%, or at least 9wt%, or at least 10wt%.

[0099] Representative features of the present invention are set out in the following clauses, which stand alone or may be combined, in any combination, with one or more features disclosed in the text of the Specification.

[0100] The present invention is as set out in the following clauses:

[0101] Clause 1. A process for producing a meal from oilseeds comprising: a. conditioning oilseed material at a temperature of at least 60°C, wherein the oilseed material comprises oilseeds and / or oilseed flakes, wherein the conditioning inactivates the myrosinase enzyme in the oilseed material; b. pressing the conditioned oilseed material to separate the oilseed material into an oil fraction and a cake fraction; c. treating the cake fraction with a solvent comprising hexane to extract residual oil and generate a defatted cake; and d. desolventizing-toasting (DT) the defatted cake to remove residual hexane and generate a defatted meal; wherein the process degrades a portion of glucosinolates in the oilseed material and wherein the oilseeds are from the Brassicaceae family.

[0102] Clause 2. The process of clause 1, wherein the defatted meal comprises a total glucosinolate content of less than 25 pmol per gram of meal by dry weight.

[0103] Clause 3. The process of any of the preceding clauses, wherein the oilseeds are from Camelina sativa.

[0104] Clause 4. The process of any of the preceding claims, wherein the oilseed material is conditioned at a temperature in the range of 75° C to 100° C.

[0105] Clause 5. The process of any of the preceding clauses, wherein the conditioning step reduces the glucosinolate content, preferably the glucosinolate content of the cake fraction is reduced by at least about 5% relative to the glucosinolate content in the oilseed material prior to conditioning.

[0106] Clause 6. The process of any of the preceding clauses, wherein the DT step is performed at a temperature of at least 75°C, preferably between 75° C to 115° C.Docket No.: PT-2225-WO-PCT

[0107] Clause 7. The process of any of the preceding claims, wherein the DT step reduces the glucosinolate content, preferably the glucosinolate content is reduced by at least about 20wt% relative to the glucosinolate content in the defatted cake prior to the DT step.

[0108] Clause 8. The process of any of the preceding clauses, wherein the glucosinolate content of the defatted meal is at least 10% less, preferably at least 25% less, relative to the glucosinolate content of the oilseeds.

[0109] Clause 9. The process of any of the preceding clauses, wherein the level of hexane in the defatted meal is less than 200ppm.

[0110] Clause 10. The process of any of the preceding clauses, further comprising flaking the oilseeds to produce oilseed flakes prior to conditioning.[OHl] Clause 11. The process of any of the preceding clauses, further comprising dry ing / cooling the defatted meal after the DT step to a moisture content of 12% or less, wherein the defatted meal comprises a total glucosinolate content of 25 pmol or less per gram of meal.

[0112] Clause 12. A defatted meal of Camelina sativa oilseed produced by the process of anyone of clauses 1-11.

[0113] Clause 13. An animal feed additive comprising a defatted meal produced from Camelina sativa oilseed, wherein the defatted meal comprises less than 25 pmol total glucosinolates per gram of meal with a moisture content less than 12wt% and an oil content of less than 5wt%. dry weight, and a protein content of less than 50wt%, dry weight.

[0114] Clause 14. The animal feed additive of clause 13, wherein the defatted meal comprises less than 20 pmol of total glucosinates per gram of meal.

[0115] Clause 15. A feed ration comprising the animal feed additive of any of clauses 13-14.

[0116] Clause 16. The feed ration of clause 15, wherein the feed ration is suitable for ruminant livestock, monogastric livestock, or poultry' livestock.

[0117] Clause 17. The feed ration of any of clauses 15-16, wherein the feed ration is formulated to maximize weight gain and meat quality of beef cattle in the feed lot, or to maximize milk production of lactating dairy' cattle.EXAMPLES

[0118] The invention is further described in detail by reference to the following experimental examples. These examples are provided for purposes of illustration only and are not intended to be limiting unless otherwise specified. Thus, the invention should in no way beDocket No.: PT-2225-WO-PCT construed as being limited to the following examples, but rather should be construed to encompass any and all variations which become evident as a result of the teaching provided herein.

[0119] Example 1. Reduction of glucosinolates through processing of camelina meal at pilot scale.

[0120] Camelina grain from the commercially available variety Joelle was used for a pilot crush and extraction. The camelina was grown from September to July.

[0121] Prior to crush, the seed was found to have 24. 12pmol / g glucosinolates specific to camelina using the method described in Meza et al. (2022), incorporated herein by reference. Camelina glucosinolates in this example were calculated based on a moisture and oil free state to provide a more accurate comparison between stages of processing.

[0122] The oilseeds ware flaked as described in Unger, E.H. “Processing” in Canola Chemistry, Production, Processing, and Utilization, p. 163-188, 2011, incorporated herein by reference.

[0123] The flaked oilseeds were conditioned for 15 minutes at about 90°C. Depending on tier of the conditioner the temperature could vary from 75°C to 105°C. The flaked, conditioned seeds then entered the screw press. The oil and the full fat press cake were separated during this process. The full fat press cake containing all camelina meal components was flushed with nitrogen and stored at -20°C overnight.

[0124] In the next step, the remaining oil from the full fat press cake was extracted using solvent, hexane, extraction. Initial extraction occurred for 45 mins at 60°C followed by three additions of clean hexanes. Sparge steam was added to the extraction vessel to a temperature of 80°C and held for one hour to desolventize the cake. There was no control of moisture. Defatted meal (after extraction and desolventization) was removed from the extractor and placed onto trays to further dry overnight.Docket No.: PT-2225-WO-PCT

[0125] The results are shown in Table 1.Table 1

[0126] The defatted meal contained 22.05pmol / g glucosinolates, indicating a decrease in a range between 10 and 23% in glucosinolates from pre-extraction full fat cake to post-extraction defatted meal in an oil free and moisture free basis as shown in Table 1. These pilot scale results demonstrated that the glucosinolates can be reduced. The temperature and moisture were difficult to control in the protocols at pilot scale.

[0127] Example 2. Reduction of glucosinolates and crude fiber content through processing of camelina meal at commercial scale

[0128] Camelina grain was grown either in the winter (winter seeds) or in spring (spring seeds). The grain was produced on at least 10 farms in the northern United States and was subsampled to determine starting glucosinolate content using the previously described method (Meza et al. 2022). The grain was subjected to the crush and refining process at a softseed crush and refining facility.

[0129] Conditioning

[0130] Oilseeds were cleaned and conditioned. In the conditioning step, the oilseeds were indirectly heated in cookers at 75-100 °C, at 10-30% moisture, for 20-40 minutes. The fine clean seeds were indirectly heated to reduce or control the moisture content of the seeds to pressing.

[0131] Pressing

[0132] After conditioning, the oilseeds w ere pre-pressed in a large screw press to remove about 50 to 60 % of their oil content. The press contained a screw that w as enclosed in a cage formed by longitudinal bars, held by a heavy frame. The screw squeezed the seeds across bars. The bars were separated by metallic spacers to allow the oil to flow between the bars while the squeezed cake was discharged to the extraction plant. Pressed oil had some footing that wasDocket No.: PT-2225-WO-PCT extruded with the oil while pressing, these footing was separated by setting and centrifuge. The heavy phase was returned and mixed back with the feed of the press while the high phase (clarified pressed oil) went to storage.

[0133] Solvent extraction

[0134] The second step of oil removal took place in a solvent extractor to remove most of the residual oil in pressed cake with hexane as solvent. A continuous belt extractor moved the pressed cake and the miscell a (hexane plus oil) in opposite directions to achieve a continuous counter current extraction. Series of pumps moved the miscella over the cake, so that the miscella with the highest concentration in oil was used to extract the entering pressed cake with the highest concentration in oil and, at the opposite extremity of the extractor, pure hexane washed the lowest concentrated extracted cake. Solvent / miscella percolated through the cake or submerged it, allowing the diffusion of the oil contained in the cake into the liquid phase.

[0135] The residual miscella (hexane / oil) contained generally 20-30 % oil and 70 to 80 % hexane. The hexane was removed by distillation from the oil to make extracted oil. This extracted oil was mixed with the pressed oil to make a crude oil that was a combination of pressed and extracted oil.

[0136] Desolventizing / toasting (DT) step

[0137] Desolventization in the DT was aimed at removing all the solvent held in the extracted cake by means of evaporation and steam stripping. DT was performed at a temperature between 80-105°C, for 40-60 minutes.

[0138] The DT was a closed vessel consisting of a vertical stack of cylindrical gas-tight pans, which are steam heated from the base. Starting from the top of the DT. the extracted cake was spread on tray one where it is equally distributed by means of a sweep arm. From there, the cake moved continuously from tray to tray through tray openings. Each of the toasting trays had hollow punches for venting vapors from one tray to the next. Direct steam was sparged in the DT by the bottom tray and moved upward from tray-to-tray stripping hexane from the cake.

[0139] The main trays were used for toasting the product. They were designed to provide both indirect heating and direct steam contact to remove the bulk of the solvent from the de-fated extracted cake. The added steam carried the evaporated hexane and get condensed in external condenser and returned to the hexane / water separator to separate the hexane from water. The hexane phase was recycled and reused back in the extractor.

[0140] Gum or soap stock out of the refining process was added to the extracted cake and feed the DT. The content of the gum (out of degumming process) or soap stock (out of the causticDocket No.: PT-2225-WO-PCT refining process) is 17 % oil and 23 % soap and 60% moisture. Combined feed was dried in the DT to remove hexane from the extracted cake and moisture from both cake and gum and soap stock stream.

[0141] The dried meal exiting the DT went through a dryer cooler to further dry and cool the meal to cool the meal to a temperature of between 50 and 80°C. During this process more hexane was removed to lower its concentration in the meal to less than 100 ppm. The cooled dried meal was then grinded and sifted to produce flowable product that went to storage.

[0142] RESULTS

[0143] Table 2 shows the results from the analysis of the content of the winter seeds and spring oil seeds.Table 2

[0144] Winter grown seeds had higher moisture and oil content than spring oil seeds. Winter grown seeds had much lower glucosinolates than spring oil seeds. Spring oil seeds had higher protein content than winter grown seeds. Spring seeds had higher chlorophyll content than winter grown seeds. This impacted the final color of the RB oil. Received winter grown seeds had higher Pods Inclusion (FM) than received spring oil seeds.

[0145] The Tables 3-9 below show the analysis of the contents after each of the steps in the process. The calculations are based on the mass balance. Table 3 shows the results of the analysis of incoming seeds. Table 4 shows the results after seeds cleaning. Table 5 shows the results after conditioning and the expeller. Table 6 show s the results after the extracting step. Table 7 show s the results after the DT step. Table 9 shows the results after the drver / cooler. Table 10 compares the content of camelina meal with canola.Docket No.: PT-2225-WO-PCTTable 3-Incoming seedsTable 4- Seeds cleaningDocket No.: PT-2225-WO-PCTTable 5-ExpellerTable 6-ExtractorDocket No.: PT-2225-WO-PCTTable 7-DTTable 9-Dryer coolerTable 10Docket No.: PT-2225-WO-PCT

[0146] Glucosinolates in winter grown seeds & meal was lower than spring oil seeds and meal. Table 10 shows the characteristics of the winter and spring meals. Most degradation of glucosinolates took place at the DT. High percent pods in the incoming seeds for processing and plant efficiency in removing the pods resulted in meal with high crude fiber content (around 16%). Crude fiber in the defatted meal can be reduced by reducing the pods in the incoming oilseeds by using finer sieves. Crude fiber was reduced / degraded during conditioning / expelling and DT. Protein concentration in winter grown meal was lower than spring oil meal (35.9% vs 39.9%). Small amount of protein degradation took place in the DT around 6%.

[0147] Example 3. Reduction of glucosinolates and crude fiber content through processing of camelina meal at different operating conditions

[0148] Camelina grain was grown in the in spring (spring seeds). The grain was produced on at least 10 farms in the northern United States and was subsampled to determine starting glucosinolate content using the previously described method (Meza et al. 2022). The grain was subjected to the crush and refining process at a softseed crush and refining facility.

[0149] Oilseeds were cleaned, conditioned and processed under two different conditions as indicated below (Run #1 and Run #2). In the conditioning step, the oilseeds were indirectly heated in cookers at 195°F (90.6°C) or at 205°F (96. 1°C), at 6-9% moisture, for 20-40 minutes. About 2.5 gallons per minute of water was added to the conditioner for a target moisture content between 6 to 7%. The fine clean seeds were indirectly heated to reduce or control the moisture content of the seeds to pressing.

[0150] Run #1 -conditioning at 195°F(90.6°C), DT at 175°F(79.4°C) and Dryer / cooler at 195°F(90.6°C)

[0151] Run #2-conditiomng at 205°F(96. 1°C), DT at 190°F(87.8°C) and Dryer / cooler at 205°F (96.1°C)

[0152] During DT, the temperature at dome of DT was 170°F up to 190°F .

[0153] The remaining process was conducted as described in Example 2.

[0154] RESULTS

[0155] The Tables 1 1 -17 below' show the analysis of the contents after each of the steps in the tw o runs of the process that w ere conducted at different temperatures as described above. The calculations are based on the mass balance. Table 11 shows the results of the analysis of incoming seeds. Table 12 shows the results after seeds cleaning. Table 13 shows the results after conditioning and the expeller. Table 14 shows the results after the extracting step. Table 15 showsDocket No.: PT-2225-WO-PCT the results after the DT step. Table 16 shows the results after the dryer / cooler. Table 17 compares the content of camelina meal with canola.Table 11 -Incoming seedsTable 12- Seeds cleaningDocket No.: PT-2225-WO-PCTTable 13-Conditioner / ExpellerTable 14-ExtractorDocket No.: PT-2225-WO-PCTTable 15-DTTable 16-Dry er coolerTable 17

[0156] Crude fiber degradation increased as the conditioning temperature increased. Crude fiber was degraded at an average of about 60%. A temperature of 175°F was sufficient for fiber breakdown.

[0157] In this document, the terms “a,” ’‘an,” or “the” are used to include one or more than one unless the context clearly dictates otherw ise. The term “or” is used to refer to a nonexclusiveDocket No.: PT-2225-WO-PCT“or” unless otherwise indicated. All publications, patents, and patent documents referred to in this document are incorporated by reference herein in their entirety, as though individually incorporated by reference. In the event of inconsistent usages between this document and those documents so incorporated by reference, the usage in the incorporated reference should be considered supplementary to that of this document; for irreconcilable inconsistencies, the usage in this document controls.

[0158] Values expressed in a range format should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range were explicitly recited. For example, a range of “about 0.1% to about 5%” or “about 0.1% to 5%” should be interpreted to include not just about 0.1% to about 5%, but also the individual values (e.g., 1%, 2%, 3%, and 4%) and the sub-ranges (e.g., 0.1% to 0.5%, 1. 1% to 2.2%, 3.3% to 4.4%) within the indicated range. The statement “about X to Y” has the same meaning as “about X to about Y,” unless indicated otherwise. Likewise, the statement “about X, Y, or about Z” has the same meaning as “about X, about Y, or about Z,” unless indicated otherwise.

[0159] Unless expressly stated, ppm (parts per million), percentage, and ratios are on a by weight basis. Percentage on a by weight basis is also referred to as wt% or % (wt) below.

Claims

Docket No.: PT-2225-WO-PCTCLAIMSWhat is claimed is:

1. A process for producing a meal from oilseeds comprising: a. conditioning oilseed material at a temperature of at least 60°C, wherein the oilseed material comprises oilseeds and / or oilseed flakes, wherein the conditioning inactivates the myrosinase enzyme in the oilseed material; b. pressing the conditioned oilseed material to separate the oilseed material into an oil fraction and a cake fraction; c. treating the cake fraction with a solvent comprising hexane to extract residual oil and generate a defatted cake; and d. desolventizing-toasting (DT) the defatted cake to remove residual hexane and generate a defatted meal; wherein the process degrades a portion of glucosinolates in the oilseed material and wherein the oilseeds are from the Brassicaceae family.

2. The process of claim 1, wherein the defatted meal comprises a total glucosinolate content of less than 25 pmol per gram of meal by dry weight.

3. The process of any of the preceding claims, wherein the oilseeds are from Camelina sativa.

4. The process of any of the preceding claims, wherein the oilseed material is conditioned at a temperature in the range of 75° C to 100° C.

5. The process of any of the preceding claims, wherein the conditioning step reduces the glucosinolate content, preferably the glucosinolate content of the cake fraction is reduced by at least about 5% relative to the glucosinolate content in the oilseed material prior to conditioning.

6. The process of any of the preceding claims, wherein the DT step is performed at a temperature of at least 75°C, preferably between 75° C to 115° C.Docket No.: PT-2225-WO-PCT7. The process of any of the preceding claims, wherein the DT step reduces the glucosinolate content, preferably the glucosinolate content is reduced by at least about 20wt% relative to the glucosinolate content in the defatted cake prior to the DT step.

8. The process of any of the preceding claims, wherein the glucosinolate content of the defatted meal is at least 10% less, preferably at least 25% less, relative to the glucosinolate content of the oilseeds.

9. The process of any of the preceding claims, wherein the level of hexane in the defatted meal is less than 200ppm.

10. The process of any of the preceding claims, further comprising flaking the oilseeds to produce oilseed flakes prior to conditioning.

11. The process of any of the preceding claims, further comprising drying / cooling the defatted meal after the DT step to a moisture content of 12% or less, wherein the defatted meal comprises a total glucosinolate content of 25 pmol or less per gram of meal.

12. A defatted meal of Camelina saliva oilseed produced by any of the process of claims 1- 11.

13. An animal feed additive comprising a defatted meal produced from Camelina saliva oilseed, wherein the defatted meal comprises less than 25 pmol total glucosinolates per gram of meal with a moisture content less than 12wt% and an oil content of less than 5wt%, dr ' weight, and a protein content of less than 50wt%, dry' weight.

14. The animal feed additive of claim 13. wherein the defatted meal comprises less than 20 pmol of total glucosinates per gram of meal.

15. A feed ration comprising the animal feed additive of any of claims 13-14.

16. The feed ration of claim 15, wherein the feed ration is suitable for ruminant livestock, monogastric livestock, or poultry livestock.Docket No.: PT-2225-WO-PCT17. The feed ration of any of claims 15-16, wherein the feed ration is formulated to maximize weight gain and meat quality of beef cattle in the feed lot, or to maximize milk production of lactating daily' cattle.

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