Polymerized vegetable oils and method of making the same

Abstract

Various aspects provide a method for making a polymerized vegetable oil. The method includes a) passing air through a heated starting vegetable oil. The starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C to form a blown polymerized vegetable oil having a viscosity higher than a viscosity of the starting vegetable oil. The method further includes b) stripping the blown polymerized vegetable oil of a) with steam or a mixture comprising nitrogen (N2) and steam, the steam or mixture of steam and nitrogen, the blown polymerized vegetable oil being at a temperature in a range of from 220 °C to 260 °C to form a stripped polymerized vegetable oil having a flash point, fire point, or both that are each higher than a flash point, fire point, or both of the blown polymerized vegetable oil at a).

Description

POLYMERIZED VEGETABLE OILS AND METHOD OF MAKING THE SAMECROSS-REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of U.S. Provisional Application No. 63 / 650,032, filed May 21, 2024. which is hereby incorporated by reference in its entirety.BACKGROUND

[0002] Oil production from vegetables has increased in recent years. The vegetable is typically ground and processed to include residual solids and other liquids. The other liquids include water, monoglycerides, diglycerides, triglycerides, glycerin, and free fatty acids. The other liquids can include free fatty acids and other liquids that can have detrimental effects such as contributing to undesirable flash point values, undesirable fire point values, or both of a polymerized vegetable oil.SUMMARY OF THE INVENTION

[0003] Various aspects provide a method for making a polymerized vegetable oil. The method includes a) passing air through a heated starting vegetable oil. The starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C (for example, from 105 °C to 150 °C, from 110 °C to 135 °C, or from 110 °C to 120 °C) to form a blown polymerized vegetable oil having a viscosity higher than a viscosity’ of the starting vegetable oil. The method further includes b) stripping the blown polymerized vegetable oil of a) with steam or a mixture comprising nitrogen (N2) and steam, the steam or mixture of steam and nitrogen, the blown polymerized vegetable oil being at a temperature in a range of from 220 °C to 260 °C (for example, from 225 °C to 255 °C, from 225 °C to 245 °C, or from 225 °C to 235 °C) to form a stripped polymerized vegetable oil having a flash point, fire point, or both that are each higher than a flash point, fire point, or both of the blown polymerized vegetable oil at a). The method can further include c) optionally introducing glycerol during b) or before b) to form a scavenged polymerized vegetable oil.

[0004] Various aspects provide a polymerized vegetable oil. The polymerized vegetable oil is produced according to a method that includes a) passing air through a heated starting vegetable oil. The starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C (for example, from 105 °C to 150 °C, from 110 °C to 135 °C, or from 110 °C to 120 °C) to form a blown polymerized vegetable oil having a viscosity' higher than a viscosity of the starting vegetable oil. The method further includes b) stripping the blown polymerized vegetable oil of a)with steam or a mixture comprising nitrogen (N2) and steam, the steam or mixture of steam and nitrogen, the blown polymerized vegetable oil being at a temperature in a range of from 220 °C to 260 °C (for example, from 225 °C to 255 °C, from 225 °C to 245 °C, or from 225 °C to 235 °C) to form a stripped polymerized vegetable oil having a flash point, fire point, or both that are each higher than a flash point, fire point, or both of the blown polymerized vegetable oil at a). The method can further include c) optionally introducing glycerol during b) or before b) to form a scavenged polymerized vegetable oil.DETAILED DESCRIPTION OF THE INVENTION

[0005] Reference will now be made in detail to certain embodiments of the disclosed subject matter. 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.

[0006] In this document, the terms “a,’7“an,” or “the7’ are used to include one or more than one unless the context clearly dictates otherwise. The term “or” is used to refer to a nonexclusive “or” unless otherwise indicated. The statement “at least one of A and B” has the same meaning as “A, B, or A and B.” In addition, it is to be understood that the phraseology or terminology employed herein, and not otherwise defined, is for the purpose of description only and not of limitation. Any use of section headings is intended to aid reading of the document and is not to be interpreted as limiting; information that is relevant to a section heading may occur within or outside of that particular section.

[0007] The term “substantially” as used herein refers to a majority of, or mostly, as in at least about 90%, 95%, 99.5%, or 100%. The term “substantially free of’ as used herein can mean having none or having a trivial amount of, such that the amount of material present does not affect the material properties of the composition including the material, such that about 0 wt% to about 5 wt% of the composition is the material, or about 0 wt% to about 1 wt%, or about 5 wt% or less, or about 0 wt%.

[0008] The term “weight-average molecular weight” as used herein refers to Mw, which is equal to SMi2n, / SMin,. where m is the number of molecules of molecular weight Mi. In various examples, the weight-average molecular weight can be determined using light scattering, small angle neutron scattering. X-ray scattering, and sedimentation velocity.

[0009] The term "Acid Value” is a measure of the residual carboxylic acid groups present in a compound and is reported in units of mg KOH / gram material. The acid number is measured according to the method of AOCS Cd 3d-63.

[0010] The term ‘‘Flash Point” or “Flash Point Temperature” is a measure of the minimum temperature at which a material will initially flash with a brief flame. It is measured according to the method of ASTM D-92 using a Cleveland Open Cup and is reported in degrees Celsius °C.

[0011] The term “Iodine Value” (IV) is defined as the number of grams of iodine that will react with 100 grams of material being measured. Iodine value is a measure of the unsaturation (carbon-carbon double bonds and carbon-carbon triple bonds) present in a material. Iodine Value is reported in units of grams iodine (I2) per 100 grams material and is determined using the procedure of AOCS Cd Id-92.

[0012] “Hydroxyl Value” is a measure of the hydroxyl (-OH) groups present in a material.It is determined using the procedure of AOCS Cd 13-60.

[0013] The term “saponification value” (SAP) is defined as the number of milligrams of potassium hydroxide needed to neutralize the fatty acids obtained by complete hydrolysis of 1 gram of an oil sample.

[0014] According to various examples described herein a method is disclosed for making a polymerized vegetable oil. Unless otherwise stated herein, vegetable oil, and oil as used herein (and derivatives thereof) is a com stillage oil or a blend of com stillage oil and another vegetable oil, (such as a blend of com stillage oil and canola oil, rapeseed oil, soybean oil, palm oil, sunflower oil, linseed oil (or a mixture thereol)). The com stillage oil is typically an oil that is recovered from ground com stillage following a fermentation process. Typically, the com stillage oil makes up from about 50 to 100 percent by weight of the starting oil, preferably from about 60 to 100 percent by weight of the starting oil, and more preferably from 65 to 100 percent by weight of the starting oil (for example from 80 to 100 percent by weight of the starting oil, and in many instances, at least 90 to 100 percent by weight of the starting oil, or at least 95 to 100 percent by weight of the starting oil). The polymerized vegetable oil produced according to the instantly claimed method can have advantageous properties relating to its viscosity (which is indicative of its weight-average molecular weight), the free fatty' acid (FA) content, the fatty7acid ethyl ester (FAEE) content, or a mixture thereof of the polymerized vegetable oil.

[0015] The viscosity for this disclosure is measured according to the method of ASTM D445. In this method, oil (e.g., a starting vegetable oil, a blown polymerized vegetable oil, a stripped polymerized vegetable oil, a scavenged vegetable oil, or a polymerized vegetable oil) tobe tested is placed in a calibrated glass capillary viscometer, which is then placed into a constant temperature bath at the temperature specified. Once thermal equilibrium is reached, the oil is drawn up into the reservoir of the capillary tube. As the fluid drains, it passes the top mark on the tube and a timer is started. When the oil passes the lower mark, the timer is stopped and the flow7time is recorded. The recorded flow time is multiplied by a factor which is specific to each viscometer tube. The resultant product of the flow' time multiplied by the factor is reported as viscosity in cSt at the test temperature.

[0016] The polymerized vegetable oil is produced first by passing air through a heated starting vegetable oil. The air is understood to primarily include oxygen and nitrogen. On a dry7basis, oxygen typically ranges from 18 vol% to 25 vol% oxygen (for example from 20 vol% to 22 vol%) and nitrogen ranges from 76 vol% to 82 vol% (for example from 78 vol% to 80 vol%).

[0017] The rate that air is delivered for a ty pical 15,000 to 40,000 pounds of oil being blown typically ranges of from 100 Ibs / hr to 500 Ibs / hr (for example, from 150 Ibs / hr to 400 Ibs / hr, 200 Ibs / hr to 350 Ibs / hr, or 200 Ibs / hr to 250 Ibs / hr). The starting vegetable oil is typically a low weight-average molecular w eight vegetable oil. An example of the starting vegetable oil utilized (e.g., a com stillage oil and / or a com stillage oil blended with another vegetable oil, such as soybean oil) is described in US Patents Number 8,779,172, 8,765,985, 8,580.988, and 8,980.807. A free fatty7acid content of the starting vegetable oil is in a range of from 0 wt% to 25 wt% (for example, from 5 wt% to 25 wt%, 10 wt% to 20 wt% or from 10 wt% to 15 wt%). It has been discovered that at least some com stillage oils comprise a fatty acid ethyl ester in a range of from 0.5 wt% to 10 wt% (for example, from 1 wt% to 10 wt% or from 3 wt% to 6 wt%).

[0018] The aforementioned rates can be affected by the volume of the vessels in which each reaction occurs (and the mass of the vegetable oil contained in the vessel). For example, an actual volume of the vessel used for the blowing step can be in a range of 8,000 liters to 100,000 liters, 10,000 liters to 40,000 liters, or 18,000 liters to 33,000 liters. A working volume of the vessel used for the blowing step typically is from fifty percent (50%) to ninety five percent (95%), preferably from sixty percent (60%) to ninety three percent (93%), and most preferably from eighty five percent (85%) to eighty eight percent (88%) of the total reactor volume. For second polymerization / stripping step reactors, the reactors utilized are ty pically similarly sized to the reactors used for the blowing step. For example, in some instances, the total size of the stripping reactor is from 18.000 to 33,000 liters and the working volume is from 20,000 to 30.000 liters, w ith a mass typically of from 30,000 pounds to 60,000 pounds for the starting vegetable oil before blow ing and stripping.

[0019] In addition to the rate that the air is delivered, the mechanism of distributing the air can be impactful. For example, distribution can include the use of a distribution system such as a plate, ring, pipe, impeller or the like. The plate ring, pipe, impeller, or the like ty pically includes a number of holes distributed about the system to allow air to pass therethrough. In some examples, the impeller is immobilized meaning that it does not spin and is a static structure through which the air passes.

[0020] The starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C (for example, from 105 °C to 150 °C, from 110 °C to 135 °C, or from 110 °C to 120 °C). The starting vegetable oil can be brought to this temperature before the air is passed therethrough or after the air is passed therethrough. The step of passing the air through the starting vegetable oil (e.g., blowing or sparging) produces a blown polymerized vegetable oil. The blown polymerized vegetable oil has a viscosity7higher than a viscosity7of the starting vegetable oil. For example, the viscosity of the starting vegetable oil of a) is in a range of from 30 to 60 cSt at 40 °C (for example, from 30 to 50 cSt at 40 °C, or from 30 to 40 cSt at 40 °C) and a viscosity of the blown polymerized vegetable oil produced at a) is in a range of from 100 to 300 cSt at 40 °C (for example, from 150 to 280 cSt at 40 °C, or from 180 to 260 cSt at 40 °C).

[0021] The increase in viscosity is indicative of the polymerization of the starting vegetable oil to form the blown polymerized vegetable oil, which has a higher weight-average molecular weight than the starting vegetable oil. The air is delivered at a rate of from 0.05 cubic feet per kilogram of flow per minute (ft3(kg-1min'1)) to 0.23 ft3(kg'1min'1), from 0.1 ft3(kg'1min'J) to 0.2 ft3(kg'1min'1), or even from 0.15 ft3(kg'1min'1) to 0.18 ft3(kg'1min'1). The rate is measured at a pressure of 1 atm.

[0022] The reactions that occur during the blowing of the starting vegetable oil increase the molecular weight of the starting vegetable oil, which tends to increase the viscosity of the blown polymerized vegetable oil versus the unblown starting vegetable oil. These viscosity7building reactions include epoxidation and subsequent ether formations. Additionally, the blowing process introduces hydroxyl functionality onto the resulting blown polymerized vegetable oil, which also tends to increase the viscosity of the blown polymerized vegetable oil relative to the starting vegetable oil. The higher viscosity' (especially at higher temperature) provides the blown polymerized vegetable oil with better hydrodynamic lubrication properties.

[0023] The blowing process can occur for a predetermined amount of time or until a predetermined event occurs such as the viscosity of the polymerized vegetable oil reaching a threshold value or a w'eight-average molecular weight of the vegetable oil reaching apredetermined value. Typically, the air is dispersed evenly in the vessel to maximize surface area exposure. The vessel preferably will have a distribution ring or spoke-like header to create small volume bubbles evenly within the oil.

[0024] For large size reactors, for example, reactors ty pically are able to blow at least 15,000 pounds, preferably at least 20,000 pounds, more preferably at least 30,000 pounds, and most preferably at least 40,000 pounds, and in some instances at least 100,000 pounds (for example, at least 150,000 pounds) of starting vegetable oil, even with good dispersion and small volume air bubbles, it may typically take longer (from 20 to 60 hours) to blow the oil to the desired viscosity. Longer sparging times typically will be necessary’ if the air is not evenly dispersed within the oil and / or the volume of the air bubbles are relatively larger.

[0025] The bl own polymerized vegetable oil is stripped after the blowing process outlined herein above. Stripping is utilized to strip the blown polymerized vegetable oil of unwanted volatile compounds. The stripping will also lower the content of free fatty’ acids in the oil.

[0026] Stripping the blown polymerized vegetable oil includes contacting and sparging the blown polymerized vegetable oil with either steam (the vapor into which water is converted when heated, forming a white mist of water droplets in the air) or a mixture of nitrogen (N2) and steam. Where a mixture of steam and nitrogen are used, the ratio (volume: volume as measured at STP) of nitrogen to steam is in a range of from 99: 1 to 1 :99 (for example from 70: 1 to 1 :70, 60: 1 to 1 :60, or 21: 1 to 1:2). In some examples, there is a greater volume of steam present than the volume of nitrogen present, w hen there is a mixture. Nitrogen can be introduced at a constant or variable rate. Similarly, steam can be introduced at a constant or variable rate. Nitrogen can be used in addition to the steam to assist in the removal of volatiles. It is shown that using a combination of steam and nitrogen and steam does not negatively impact the increase in viscosity.

[0027] In some examples, steam alone is used to strip (e.g., nitrogen is not used except optionally to quickly purge air from the vessel prior to introducing steam). In some examples w hen a mixture of steam and nitrogen is used, the stripping includes one cycle of introducing nitrogen first followed by introducing steam. During stripping, the blown polymerized vegetable oil is at a temperature in a range of from 220 °C to 260 °C (for example, from 225 °C to 255 °C, from 225 °C to 245 °C, or from 225 °C to 235 °C). At these temperatures, the oil’s viscosity’ during the stripping ty pically will be increased, lighter species react with each other and heavier species. Additionally, some lighter species (such as, fatty acids and fatty’ acid ethyl esters) will also be removed during the stripping step. The overall effect is that during the stripping step the average molecular weight of the oil tends to increase, and the viscosity’ tends to increase. Typically, atemperature lower than 220 °C results in the stripping process being too slow and a temperature above 260 °C creates too many breakdown products (e.g., fragmented) of the blown polymerized vegetable oil.

[0028] The viscosity of the stripped polymerized vegetable oil at the end of stripping typically is from 130 to 800 cSt at 40 °C (for example, from 300 to 750 cSt at 40 °C. or from 300 to 600 cSt at 40 °C).

[0029] The amount of steam delivered, typically is in a range of from 0. 1 to 5 wt% steam ((weight steam + w eight of oil)'1hour_1)(for example, from 0.2 to 4 wt% steam ((w eight steam + weight of oil)1hour1), from 0.3 to 3 wt% steam ((weight steam + weight of oil)1hour1), from 0.4 to 2 wt% steam ((w eight steam + weight of oil)'1hour'1), or from 0.4 to 1 wt% steam ((weight steam + weight of oil)'1hour'1).

[0030] Stripping includes controlling the pressure in the environment (e g., reaction vessel). For example, stripping is conducted at a pressure of less than 50 Torr (for example, less than 40 Torr, less than 30 Torr, or less than 22.8 Torr) or in a range of from 15 Torr to 45 Torr (for example from about 20 Torr to about 30 Torr). If the pressure utilized for stripping is not low enough, undesired materials such as the free fatty' acid and fatty acid ethyl ester will not be sufficiently removed. The low pressures utilized can result in the stripping process being labeled as a vacuum stripping process. The low pressure in conjunction with the high temperature and use of steam at least partially during stripping produces a resulting stripped polymerized vegetable oil having a higher flash point, fire point, or both. The higher flash point, fire point, or both is attributed to the stripping step’s ability to lower the free fatty acid content, fatty acid ethyl ester content, or both of the blown polymerized vegetable oil to form the stripped polymerized vegetable oil.

[0031] The stripped polymerized vegetable oil has a viscosity higher than a viscosity of the blown polymerized vegetable oil. Surprisingly and unexpectedly, it w as found that introducing steam during stripping did not reduce the viscosity of the resulting stripped polymerized vegetable oil. nor appreciably reduce the rate at which the viscosity of vegetable oil increases during stripping.

[0032] “Flash Point” is a measure of the minimum temperature at which a material will initially flash w ith a brief flame. It is measured according to the method of ASTM D92 (published in 2018) using a Cleveland Open Cup and is reported in degrees Celsius (°C). “Fire Point” is the measure of the low est temperature at which a fuel continues to bum for a short time period after initiation of ignition. The fire point is also measured according to the method of ASTM D92.

[0033] The higher flash point, fire point, or both of the stripped polymerized vegetable oil stripped according to the method herein described (including, at least partially using steam to strip the oil), compared to the blown polymerized vegetable oil that has been stripped without the use of steam, is attributable to the lowering of free fatty acid content and the fatty acid ethyl ester content, more effectively than stripping without the use of steam during the stripping (with steam introduced at the rates described herein above). The fatty acid ethyl ester content of the stripped polymerized vegetable oil of b) is less than 2.0 wt%, less than 1.5 wt%, less than 1.0 wt%, less than 0.75 wt%, or in a range of from 0.001 wt% to 2.0 wt% (for example, from 0.01 wt% to 1 wt% or from 0. 1 wt% to 0.75 wt%).

[0034] In some examples the blown polymerized vegetable oil, the stripped polymerized vegetable oil, or both can be scavenged. Scavenging is accomplished by introducing a polyol (meaning an organic compound containing multiple hydroxyl groups) to the blow'll polymerized vegetable oil, stripped polymerized vegetable oil, or both. Scavenging can help to reduce the free fatty acid content, fatty acid ethyl ester content, or both of the blown polymerized vegetable oil, stripped polymerized vegetable oil, or both. In some examples scavenging the blown polymerized vegetable oil prior to stripping can help the blown polymerized vegetable oil be more readily stripped.

[0035] The added polyol preferably has a molecular weight of at least 80 Daltons (more preferably at least 85 Daltons, and more preferably at least 90 Daltons). In order to aid in the reaction of the polyol with the free fatty acids, the polyol preferably has a hydroxyl number of at least 200 mg KOH / gram (more preferably at least 1000 mg KOH / gram). Preferably, the polyol has at least two hydroxyl groups per molecule, and more preferably at least 3 hydroxyl groups per molecule. The polyol preferably has a boiling point of at least 250 °C, more preferably at least 270 °C (more preferably at least 285 °C). Any reference to boiling point herein means the boiling point at a pressure of 760 mm Hg. Due to its relatively high molecular weight (92 Daltons), relatively high boiling point (290 °C), high number of hydroxyl groups per molecule (3), and ready commercial availability, glycerin is the preferred polyol to utilize in the invention.

[0036] Examples of other polyols that may be utilized include, but are not limited to, trimethylol propane (“TMP”), polyethylene glycol (“PEG’’), pentaerythritol, sorbitol, erythritol, maltitol, and glycerol. In preferred examples, the polyol is glycerol.

[0037] In certain preferred aspects of the invention, the polyol (e.g., glycerol) contains less than 500 ppm chloride ions. In certain aspects, the polyol contains less than 300 ppm, less than 200 ppm, less than 100 ppm, less than 70 ppm, or less than 50 ppm chloride ions. Reduced chlorideion concentrations may minimize corrosion concerns in products that are manufactured utilizing a blown, stripped polymerized vegetable oil of the present invention. In one particularly preferred aspect, the polyol comprises technical grade or USP glycerol, typically having less than 30 ppm chloride ions and preferably less than 20 ppm chloride ions (for example less than 10 ppm chloride ions).

[0038] In operation, any of the blowing and stripping procedures can be performed in the same reaction vessel. However, more typically, the blowing and stripping procedures are performed in separate reaction vessels. If glycerol is used to scavenge the blown polymerized vegetable oil or stripped polymerized vegetable oil. the glycerol can be added to whichever, reaction vessel is used to perform the blowing procedure, stripping procedure, or both.

[0039] The flash point of the stripped polymerized vegetable oil ty pically is at least 300 °C, preferably at least 303 °C, more preferably at least 304 °C and in some instances at least 308 °C (for example, at least 310 °C) by Cleveland open cup. The inventors discovered that these high flash points can surprisingly be reached and be reached more efficiently and effectively through the use of steam during the stripping step. Additionally, heavily blowing and stripping the vegetable oil using heat results in a stripped polymerized vegetable oil with molecular weights and viscosities sufficiently high to be able to be used effectively in end-use applications requiring such high flash points.

[0040] The combined final concentration of fatty acid and fatty acid ethyl esters in the stripped polymerized vegetable oil typically is 2.5 wt% or less, more preferably 2.0 wt% or less, and in some instances 1.8 wt% or less.

[0041] The high flash point of the stripped polymerized vegetable oils of the invention will help minimize the chances of sparking and / or explosions in high flash point environments.

[0042] Typically, the high-flash point stripped polymerized vegetable oils of the invention also exhibits a pour point of lower than 0 °C, preferably lower than negative 5 °C. “Pour Point'’ or “Pour Point Temperature'’ is a measure of the lowest temperature at which a fluid will flow. It is measured according to the method of ASTM D-97 and is reported in degrees Celsius (°C). This provides an oil that remains flowable at relatively low temperatures, while still exhibiting good viscosity and lubrication at high temperatures and a high flash point, as described above.

[0043] Examples of additional end-use applications that require such high flash points oils include, but are not limited to. asphalt modification, metal forging lubricants, fluids for stabilization of sand molds utilized in metal casting, and high temperature bearing lubricants. Examples of applications where the polymerized oil of this invention are advantageous includeapplications where high temperature De-dusting fluids are utilized, such as in the manufacture of fiberglass insulation and stone wool insulation applications.EXAMPLES

[0044] Various embodiments of the present invention can be better understood by reference to the following Examples which are offered by way of illustration. The present invention is not limited to the Examples given herein.Table 1: Materials

[0045] Com stillage oil (version 1) is formed by exposing fermented com mash to temperatures of about 82.2° C under a vacuum from about 50 Torr to about 300 Torr to distill off ethanol. The com stillage oil is recovered by centrifuging the materials remaining after the distillation to recover the vacuum distilled com stillage oil. The properties of the vacuum distilled com stillage oil is set forth below in Table 2. While not measured, the vacuum distilled com stillage oil is believed to contain from about 5 to about 12 percent by weight titre.Table 2.

[0046] Com Stillage oil (version 2) is formed by exposing fermented com mash to temperatures of about 112 °C to 121 °C at pressures of from about 51 Torr to about 775 Torr to distill off ethanol. The pressure distilled com stillage oil is recovered by centrifuging the material remaining after the distillation to recover the pressure distilled com stillage oil. The properties of the pressure distilled com stillage oil is set forth below in Table 3. While not measured, the pressure distilled com stillage oil is believed to contain from about 5 to about 12 percent by weight titre.Table 3.Example 1 - Manufacture of OIL 1:

[0047] Oil 1 is made starting with com stillage oil (version 1) set out above. The com stillage oil is blown and stripped, as follows: The blowing step includes 45,000 pounds of com stillage oil is charged into a 30,000-liter reactor vessel equipped with an impeller with blades that have outlets to sparge air through the reactor vessel. The com stillage oil is heated to a temperature of 110 °C. Air is sparged through the oil as it is heated at a rate of 14,000 cubic feet per minute. The viscosity of the oil increases over time, reaching a viscosity of two hundred centistokes at forty degrees Celsius (200 cSt at 40 °C), at which point the air sparge is ceased. The blown oil is allowed to cool and then charged into a stripping reactor. Glycerol (0.3 percent by weight based on the overall weight of the oil present) is added to the stripping reactor. In the stripping reactor the blown com stillage oil is heated and sparged with nitrogen at atmospheric pressure. The temperature of the stripping reactor is raised to 230 °C and maintained at that temperature under the nitrogen sparge until the desired viscosity, acid value, and flash point set forth below are reached. It takes approximately 15 hours to carry out the stripping step. During the nitrogen sparging the molecular weight of the oil is increasing and free fatty acids and other low molecular weight components are stripped out of the oil. The oil within the reactor is periodically tested for acid value and flash point. Typically, the desired viscosity (370 centistokes at forty degrees Celsius (370 cSt at 40 °C)) and acid value (less than 3 mg KOH / gram oil) are reached, before the desired flash point 289 °C is reached. After the nitrogen sparge (stripping) is ceased, the blown, stripped com stillage oil is allowed to cool to ambient temperature. The properties of Oil 1 are listed below Table 4.Example 2 - Manufacture of OIL 2:

[0048] Oil 2 is produced starting with com stillage oil (version 1) as described above. The com stillage oil undergoes a blowing and stripping process. In the blowing step, 45,000 pounds of com stillage oil is charged into a 30,000-liter reactor vessel equipped with an impeller with blades that have outlets to sparge air through the vessel. The oil is heated to 1 10°C, and air is sparged through the oil at a rate of 14,000 cubic feet per minute as it is heated. The viscosity of the oil increases over time, reaching 200 centistokes at 40°C (200 cSt at 40°C), at which point theair sparging is ceased, and the blown oil is allowed to cool. The cooled blown oil is then charged into a 2-liter round bottom reactor, where glycerol (1.5% by weight based on the overall weight of the oil present) is added. The oil is heated and sparged with nitrogen at 15 liters per hour. The temperature is raised to 230 °C and maintained under the nitrogen sparge until the desired viscosity, acid value, and flash point (as set forth in Table 8) are reached, which takes approximately 19 hours. During nitrogen sparging, the molecular weight of the oil increases, and free fatty acids and other low molecular weight components are stripped out. The oil is periodically tested for acid value and flash point. Typically, the desired viscosity (370 centistokes at 40 °C (370 cSt at 40 °C)) is reached, with a flash point of 269°C reported for this batch. After the nitrogen sparging is ceased, the blown, stripped com stillage oil is allowed to cool to ambient temperature. The properties of OIL 2 are listed below in Table 8.Example 3 - Manufacture of OIL 3:

[0049] Oil 1 is charged into a round bottom flask and installed into a distillation reactor setup. Agitation and a nitrogen and steam sparge is applied. The reactor is then heated to increase the temperature of Oil 1 to 230 °C and the pressure is reduced to 20 Torr. Two and a half weight percent (2.5 wt%) of the charged OIL l ’s weight in water is converted to steam and sparged through the oil at a rate of 0.5 to 1.5 wt% per hour to strip remaining volatiles from OIL 1. The reactor is slowly cooled under vacuum after the steam sparge is completed to dry the oil. A 98.9% yield of Oil 3 from Oil 1 is observed from the steam sparge of OIL 1. Some material and water are observed in the condenser and receiving flask.

[0050] Data relating to the blown and steam sparged com stillage oil (Oil 3) is set forth in Table 4.Wet Chemical Analysis of OIL 1 and OIL 3:Table 4: Wet chemical analysis of OIL 1 and steam sparge OIL 1 (OIL 3)

[0051] As can be seen from Table 4, steam stripping a polymerized vegetable oil that was previously stripped using nitrogen alone, removes further undesirable volatile species, such as fatty acid ethyl esters that are difficult to remove without the use of steam sparging and higher vacuum as described herein (e.g., a pressure during steam sparging of less than 50 Torr). Additionally, it is believed that using steam sparging at low pressure during stripping of a blown vegetable oil instead of or in addition to nitrogen sparging will provide materials with higher flash point and lower concentrations of fatty acids and / or fatty acid ethyl esters than nitrogen sparging alone; and, for equivalent values of flash point, fatty acid and / or fatty acid ethyl ester concentration, steam stripping at a low pressure can more quickly and efficiently reach the desired values than nitrogen stripping alone.

[0052] As can be seen in Table 4, the steam stripping did not significantly change with makeup of the final stripped material with regard to monomers and polymers.Flash and Fire Point Definitions:• Cleveland Open Cup flash point: Determined according to ASTM D92.• Fire point: Determined according to ASTM D92.Example 4 - Manufacture of steam sparged and high vacuum stripped polymerized vegetable oil (OIL 4):

[0053] Oil 4 is made starting with com stillage oil (version 1) set out above. The com stillage oil is blown and stripped, as follows: in the blowing step 45.000 pounds of com stillage oil is charged into a 30,0004iter reactor vessel equipped with an impeller with blades that have outlets to sparge air through the reactor vessel. The com stillage oil is heated to a temperature of 110 °C. Air is sparged through the oil as it is heated at a rate of 14,000 cubic feet per minute. The viscosity of the oil increases over time, reaching a viscosity of two hundred centistokes at forty’ degrees Celsius (200 cSt at 40 °C), at which point the air sparge is ceased. The blown oil is allow ed to cool and then charged into a stripping reactor. Glycerol (0.3 percent by weight based on the overall weight of the oil present) is added to the stripping reactor. In the stripping reactor the blown com stillage oil is heated and sparged with steam at a pressure of less than 50 Torr. Thetemperature of the stripping reactor is raised to 230 °C and maintained at that temperature under the steam sparge at a pressure of less than 50 Torr until the desired viscosity, acid value, fatty acid ethyl ester content, and flash point set forth below are reached. The rate of steam introduction during the stripping is from 0. 1 to 5 wt% steam ((weight steam + weight of oil)’1hour’1). The total mass of steam introduced typically is from 1.5 wt% to 2.5 wt% of the overall mass of the oil being stripped. It takes from approximately 2 hours to 25 hours (preferably from 12 to 20 hours) to carry out the steam stripping step, depending on the steam introduction rate. During the steam sparging the molecular weight of the oil increases and free fatty' acids and fatty' acid ethyl esters and other low molecular weight components are stripped out of the oil. The oil within the reactor is periodically tested for acid value, flash point, and optionally fatty acid ethyl ester content. Typically the desired viscosity (370 centistokes at forty7degrees Celsius (370 cSt at 40 °C)), acid value (less than 3 mg KOH / gram oil), fatty' acid ethyl ester content (2.0 wt% or less), the sum of fatty acid and fatty acid ethyl ester percent by weight less than 2.5 wt%, and flash point of at least 300 °C (preferably at least 303 °C) are reached within from about 2 to 25 hours (preferably from 12 to 20 hours), depending on the steam introduction rate. Once the desired flash point and acid value have been attained, and the desired amount of steam has been introduced, the steam sparge is stopped, the pressure is allowed to raise to atmospheric pressure (or nitrogen is introduced to raise the pressure to atmospheric), and the stripped polymerized vegetable oil is allowed to cool to ambient temperature. In one alternate embodiment, the stripped polymerized vegetable oil is held under vacuum to reduce the moisture content of the oil, prior to removing the vacuum. The properties of Oil 4 are listed below Table 5.Table 5: Wet chemical analysis of OIL 4

[0054] As can be seen from Table 5, the flash point for Oil 4 is higher than the flash point of Oil 1 (i.e., stripped with nitrogen sparge); and the acid value (AV), fatty acid content, and fatty acid ethyl ester content are lower for Oil 4 than Oil 1. Showing the improved properties that can readily and effectively be obtained by the use of a stripping step that utilizes steam sparging together with a relatively low pressure.Example 5 - Manufacture of nitrogen and steam sparged and high vacuum stripped polymerized vegetable oil (OIL 5):

[0055] Oil 5 is made starting with com stillage oil (version 1) set out above. The com stillage oil is blown and stripped, as follows: the blowing step includes 45,000 pounds of com stillage oil is charged into a 30,000-liter reactor vessel equipped with an impeller with blades that have outlets to sparge air through the reactor vessel. The com stillage oil is heated to a temperature of 110 °C. Air is sparged through the oil as it is heated at a rate of 14,000 cubic feet per minute. The viscosity of the oil increases over time, reaching a viscosity of two hundred centistokes at forty degrees Celsius (200 cSt at 40 °C), at which point the air sparge is ceased. The blown oil is allowed to cool and then charged into a stripping reactor. Glycerol (0.3 percent by weight based on the overall weight of the oil present) is added to the stripping reactor. In the stripping reactor the blown com stillage oil is heated to a temperature of 230 °C and sparged with nitrogen to strip volatiles from the reactor. Once the oil reaches a desired acid value (typically less than 10 mg KOH / gram, preferably less than 5 mg KOH / gram), a steam sparge is commenced and the pressure is reduced to 50 Torr. The temperature of the stripping reactor is maintained at 230 °C under the steam sparge at a pressure of less than 50 Torr until the desired viscosity, acid value, fatty acid ethyl ester content, and flash point set forth below are reached. The rate of steam introduction during the stripping is from 0.1 to 5 \\1% steam ((weight steam + weight of oil)'1hour'1). The amount of steam introduced during the steam sparge is from 1.5 to 2.5 wt% of the oil being stripped. It takes approximately 2 to 25 hours (preferably from 12 to 20 hours) of nitrogen stripping and steam stripping to carry out the stripping step. During the steam sparging the molecular weight of the oil increases and free fatty acids and fatty acid ethyl esters and other low molecular weight components are stripped out of the oil. The oil within the reactor is periodically tested for acid value, flash point, and optionally fatty acid ethyl ester content. Typically, the desired viscosity (370 centistokes at forty degrees Celsius (370 cSt at 40 °C)) acid value (less than 3 gm KOH / gram oil), fatty acid ethyl ester content (2.0 wt% or less), the sum of fatty acid and fatty acid ethyl ester percent by weight less than 2.5 wt%, and flash point of at least 300 °C(preferably at least 303 °C) are reached within about 2 to 25 hours (preferably from 12 to 20 hours) of the stripping step commencing. In this example, the steam sparging typically makes up 2 to 4 hours of the total time for the stripping step. The preferred steam introduction rate during the steam stripping is from 1 to 1.5 wt% steam ((weight steam = weight of oil)'1hour'1) for a time period of 1 to 2.5 hours. Once the desired acid value and flash point are reached (and the desired amount of steam has been introduced), the steam sparge is stopped, the pressure is allowed to raise to atmospheric pressure, and the stripped polymerized vegetable oil is allowed to cool to ambient temperature. In one alternate embodiment, the stripped polymerized vegetable oil is held under vacuum to reduce the moisture content of the oil. prior to removing the vacuum. The properties of Oil 5 are listed below Table 6.Table 6: Wet chemical analysis of OIL 5

[0056] As can be seen from Table 6, the flash point for Oil 5 is higher than the flash point of Oil 1 (i.e., stripped with nitrogen sparge); and the acid value (AV), fatty acid content, and fatty’ acid ethyl ester content are lower for Oil 5 than Oil 1 . Showing the improved properties that can readily and effectively be obtained by the use of a nitrogen sparge followed by a steam stripping step that utilizes steam sparging together with a relatively low pressure.Example 6 - Manufacture of nitrogen and steam sparged and high vacuum stripped polymerized vegetable oil (OIL 6):

[0057] Oil 6 is produced starting with com stillage oil (version 1) as described above. The com stillage oil undergoes a blowing and stripping process, detailed as follows: In the blowing step, 45,000 pounds of com stillage oil is charged into a 30,000-liter reactor vessel equipped withan impeller with blades that have outlets to sparge air through the vessel. The oil is heated to 1 10°C, and air is sparged through the oil at a rate of 14,000 cubic feet per minute as it heats. The viscosity of the oil increases over time, reaching 200 centistokes at 40 °C (200 cSt at 40 °C), at which point the air sparging is ceased. The blown oil is allowed to cool and then charged into a stripping reactor. In the stripping step, glycerol (0.7% by weight based on the overall weight of the oil) is added to the stripping reactor. The blown com stillage oil is heated and sparged with steam at a pressure of less than 50 Torr. The temperature is raised to 230 °C and maintained under steam sparging at less than 50 Torr until the desired viscosity, acid value, fatty acid ethyl ester content, and flash point are reached. The rate of steam introduction during stripping is from 0.1 to 5 wt% steam ((weight steam + weight of oil)-l hour-1). The total mass of steam introduced ty pically ranges from 1.5 wt% to 2.5 wt% of the overall mass of the oil being stripped. The steam stripping step takes approximately 2 to 25 hours (preferably 12 to 20 hours), depending on the steam introduction rate. During steam sparging, the molecular weight of the oil increases, and free fatty acids, fatty acid ethyl esters, and other low molecular weight components are stripped out. The oil within the reactor is periodically tested for acid value, flash point, and optionally fatty acid ethyl ester content. Typically, the desired viscosity7(370 centistokes at 40 °C (370 cSt at 40 °C)), acid value (less than 3 mg KOH / gram oil), fatty acid ethyl ester content (2.0 wt% or less), the sum of fatty acid and fatty acid ethyl ester percent by weight (less than 2.5 wt%), and flash point (at least 300 °C, preferably at least 303 °C) are reached within 2 to 25 hours (preferably 12 to 20 hours), depending on the steam introduction rate. Once the desired flash point and acid value are attained, and the desired amount of steam has been introduced, the steam sparging is stopped. The pressure is allowed to rise to atmospheric pressure (or nitrogen is introduced to raise the pressure to atmospheric), and the stripped polymerized vegetable oil is allowed to cool to ambient temperature. In one alternate embodiment, the stripped polymerized vegetable oil may be held under vacuum to reduce the moisture content before removing the vacuum.Table 7: Wet chemical analysis of OIL 6

[0058] As shown in Table 7, the flash point for Oil 6 is higher than that of Oil 1 (stripped with nitrogen sparging). The acid value (AV), fatty' acid content, and fatty acid ethyl ester content are lower for Oil 6 than Oil 1, demonstrating the improved properties obtained through steam sparging at relatively low pressure.Example 7 - Manufacture of nitrogen and steam sparged and high vacuum stripped polymerized vegetable oil (OIL 7):

[0059] Oil 2 is charged into a round-bottom flask and installed into a distillation reactor setup. Agitation and nitrogen are applied. The reactor is then heated to increase the temperature of Oil 2 to 230°C, and the pressure is reduced to 25 Torr. Approximately 4.0 wt% of the charged Oil 2's weight in water is converted to steam and sparged through the oil at a rate of 1.0 wt% per hour to strip remaining volatiles from Oil 2. The temperature of the stripping reactor is maintained at 230°C under the steam sparge at a pressure of less or equal to 25 Torr until the desired viscosity, acid value, fatty7acid ethyl ester content, and flash point are reached. During the steam sparging, the molecular weight of the oil increases, and free fatty' acids, fatty acid ethyl esters, and other low molecular weight components are stripped out of the oil. The oil within the reactor is periodically tested for acid value, flash point, and optionally fatty acid ethyl ester content. Once the desired acid value and flash point are reached, as shown in the table, the steam sparge is stopped, the pressure is allowed to rise to atmospheric pressure, and the stripped polymerized vegetable oil is allowed to cool to ambient temperature. After the steam sparge is completed, the reactor is slowly cooled under vacuum to dry the oil. Some material and water are observed in the condenser and receiving flask.Wet Chemical Analysis of OIL 2 and OIL 7 :Table 8: Wet chemical analysis of OIL 2 and steam sparge of Oil 2 (OIL 7)

[0060] As shown in Table 8, the flash point for Oil 7 is significantly higher than that of Oil 2 (stripped with nitrogen sparging). The acid value (AV), fatty acid content, and fatty7acid ethyl ester content are lower for Oil 7 than Oil 2, demonstrating the improved properties obtained through steam sparging.

[0061] The terms and expressions that have been employed are used as terms of description and not of limitation, and there is no intention in the use of such terms and expressions of excluding any equivalents of the features shown and described or portions thereof, but it is recognized that various modifications are possible within the scope of the embodiments of the present invention. Thus, it should be understood that although the present invention has been specifically disclosed by specific embodiments and optional features, modification and variation of the concepts herein disclosed may be resorted to by those of ordinary skill in the art, and that such modifications and variations are considered to be w ithin the scope of embodiments of the present invention.

Claims

CLAIMSWhat is claimed is:

1. A method for making a polymerized vegetable oil, the method comprising: a) passing air through at least 15,000 pounds to 150.000 pounds of a heated starting vegetable oil, wherein the starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C (for example, from 105 °C to 150 °C, from 110 °C to 135 °C, or from 110 °C to 120 °C) to form a blown polymerized vegetable oil having a viscosity higher than a viscosity of the starting vegetable oil; b) stripping the blown polymerized vegetable oil of a) with steam or a mixture comprising nitrogen (N2) and steam, the steam or mixture of steam and nitrogen, the blown polymerized vegetable oil being at a temperature in a range of from 220 °C to 260 °C (for example, from 225 °C to 255 °C, from 225 °C to 245 °C, or from 225 °C to 235 °C) to form a stripped polymerized vegetable oil having a flash point of at least 300 °C (for example, at least 303 °C, at least 304 °C, at least 308 °C, or at least 310 °C); and c) optionally introducing glycerol during b) or before b) to form a scavenged polymerized vegetable oil, wherein stripping the blown polymerized vegetable oil of b) is conducted at a pressure of 50 Torr or less (for example, 40 Torr or less, or 30 Torr or less).

2. The method of claim 1, wherein a free fatty7acid content of the starting vegetable oil of a) is in a range of from 0 wt% to 25 wt% (for example, from 5 wt% to 25 wt%, 10 wt% to 20 wt% or from 10 wt% to 15 wt%).

3. The method of any one of claims 1 or 2, wherein a fatty7acid ethyl ester content of the starting vegetable oil of a) is in a range of from 0.5 wt% to 10 wt%, 1 wt% to 10 wt% (for example, from 2 wt% to 8 wt% or from 3 wt% to 6 wt%).

4. The method of any one of claims 1-3, wherein the starting vegetable oil comprises a blend of com stillage oil and an unsaturated vegetable oil.

5. The method of any one of claims 1-4, wherein the unsaturated vegetable oil comprises canola oil, rape seed oil, sunflower oil, soybean oil, a linseed oil, or a mixture thereof.

6. The method of any one of claims 1-5, wherein the viscosity of the starting vegetable oil of a) is in a range of from 30 to 60 cSt at 40 °C (for example, from 30 to 50 cSt at 40 °C, or from 30 to 40 cSt at 40 °C).

7. The method of any one of claims 1-6, wherein a viscosity of the blown polymerized vegetable oil produced at a) is in a range of from 100 to 300 cSt at 40 °C (for example, from 150 to 280 cSt at 40 °C, or from 180 to 260 cSt at 40 °C); and / or wherein a viscosity of the stripped, polymerized vegetable oil produced at b) is from 130 to 800 cSt at 40 °C (for example, from 300 to 750 cSt at 40 °C, or from 300 to 600 cSt at 40 °C ) .

8. The method of any one of claims 1-7, wherein the heated starting vegetable oil at a) is at a temperature in a range 110 °C to 135 °C.

9. The method of any one of claims 1-8, wherein the air and is delivered at a rate in a range of 0.05 ft3(kg-1min'1) to 0.23 ft3(kg'1min'1).

10. The method of any one of claims 1-9, wherein the air and is delivered at a rate in a range of 0. 1 ft3(kg'1min'1) to 0.2 ft3(kg'1min'1) (for example, from 0. 15 ft3(kg'1min'1) to 0. 18 ft3(kg'1min'1).

11. The method of any one of claims 1-10, wherein step b) is performed in a different reaction vessel from a reaction vessel used to pass the air through the starting vegetable oil at a).

12. The method of any one of claims 1-11, wherein stripping the blown polymerized vegetable oil at b) is conducted at a pressure of less than 40 Torr (for example, less than 30 Torr, less than 25 Torr, or less than 22.8 Torr).

13. The method of any one of claims 1-12, wherein stripping the blown polymerized vegetable oil at b) is conducted at a pressure in a range of from 15 Torr to 45 Torr (for example from about 20 Torr to about 30 Torr).

14. The method of any one of claims 12 or 13, wherein the pressure is varied during stripping.

15. The method of any one of claims 12 or 13. wherein the pressure is constant during stripping.

16. The method of any one of claims 1-15, wherein at b), steam is introduced and no nitrogen is introduced.

17. The method of any one of claims 1-16, wherein at b), a ratio of nitrogen to steam is in a range of from 99: 1 to 1 :99 (for example from about 70: 1 to about 1 :70).

18. The method of any one of claims 1-17, wherein the nitrogen and steam are introduced at b) simultaneously, or introduction of nitrogen is followed by introduction of steam at b).

19. The method of any one of claims 1-18, wherein the nitrogen is introduced at a constant rate at b).

20. The method of any one of claims 1-19, wherein the nitrogen is introduced at a variable rate at b).

21. The method of any one of claims 18-20, wherein at b) a single cycle of nitrogen introduction followed by introduction of steam is performed.

22. The method of any one of claims 1-21, wherein at b), steam used to strip the blown polymerized vegetable oil is delivered at a constant rate of addition during b).

23. The method of any one of claims 1-22, wherein at b), steam used to strip the blown polymerized vegetable oil is delivered at a variable rate amount during b).

24. The method of any one of claims 1-23, wherein at b), steam used to strip the blown polymerized vegetable oil is introduced at a rate of from 0. 1 to 5 wt% steam ((weight steam +weight of oil)'1hour’1) (for example, from 0.2 to 4 wt% steam ((weight steam + weight of oil)’1hour’1), 0.3 to 3 wt% steam ((weight steam + weight of oil)’1hour’1), 0.4 to 2 wt% steam ((weight steam + weight of oil)’1hour’1), or 0.4 to 1 wt% steam ((weight steam + weight of oil)’1hour’1).

25. The method of any one of claims 1-24, wherein the sum of the free fatty acid content and the fatty acid ethyl ester content of the stripped polymerized vegetable oil is less than 2.5 wt% (for example, less than 2.0 wt% or less than 1.8 wt%).

26. The method of any one of claims 1-25, wherein a fatty acid ethyl ester content of the stripped polymerized vegetable oil of b) is less than 2.0 wt%, less than 1.5 wt%, less than 1.0 wt%, or less than 0.75 wt%.

27. The method of any one of claims 1-26, wherein the air comprises 18 vol% to 25 vol% oxygen on a dry basis (for example from 20 vol% to 22 vol%).

28. The method of any one of claims 1-27, wherein the stripped polymerized vegetable oil of b) has a viscosity higher than a viscosity of the blown polymerized vegetable oil of a).

29. A method for making a polymerized vegetable oil, the method comprising: a) passing air through at least 15,000 pounds to 150,000 pounds of a heated starting vegetable oil comprising com stillage oil, wherein the starting vegetable oil is heated to a temperature in a range of from 100 °C to 200 °C (for example, from 105 °C to 150 °C, from 110 °C to 135 °C, or from 110 °C to 120 °C) to form a blown polymerized vegetable oil having a viscosity higher than a viscosity7of the starting vegetable oil; b) stripping the blown polymerized vegetable oil of a) w ith steam or a mixture comprising nitrogen (N2) and steam, the steam or mixture of steam and nitrogen, the blown polymerized vegetable oil being at a temperature in a range of from 220 °C to 260 °C (for example, from 225 °C to 255 °C, from 225 °C to 245 °C, or from 225 °C to 235 °C) to form a stripped polymerized vegetable oil having a flash point, fire point, or both that are each higher than a flash point, fire point, or both of the blown polymerized vegetable oil at a); andc) introducing glycerol during b) or before b) to form a scavenged polymerized vegetable oil, wherein a flash point of the stripped polymerized vegetable oil is at least 300 °C (for example, at least 303 °C, at least 304 °C, at least 308 °C, at least 310 °C, wherein stripping the blown polymerized vegetable oil at b) is conducted at a pressure of less than 50 Torr (for example, less than 40 Torr, or less than 30 Torr).

30. The method of any of claims 1-29, wherein the starting vegetable oil comprises from about 1.0 wt% to about 10 wt% fatty acid ethyl esters.

31. The method of claim 30, wherein the starting vegetable oil comprises at least fifty percent by weight (50 wt%) com stillage oil.

32. The method of any of claims 30 and 31, wherein the starting vegetable oil comprises from 2.0 wt% to 9.5 wt% fatty acid ethyl esters (for example from 2.0 to 7.0 wt% fatty acid ethyl esters).

33. The method of any of claims 1-32, wherein the amount of steam introduced during the steam sparge is from 1.0 to 10.0 wt% (for example from 1.0 to 5 wt% or from 1.5 to 2.5 wt%) of the oil being stripped.

34. A polymerized vegetable oil formed according to any of the methods of claims 1-33.

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