Filterability of fuel blends containing biodiesel

Abstract

A method for reducing filter blocking tendency of a fuel composition is described. The fuel composition includes biodiesel component and renewable diesel component or petroleum diesel component. The method involves dosing the fuel composition with imidazoline or diamine with hydrocarbyl ether substituent additive.

Description

[0001] FILTERABILITY OF FUEL BLENDS CONTAINING BIODIESEL

[0002] CROSS-REFERENCE TO RELATED APPLICATION

[0003]

[0001] This application claims the benefit of U.S. Provisional Patent Application No. 63 / 708,581, filed October 17, 2024, which is incorporated by reference herein in its entirety.

[0004] FIELD OF DISCLOSURE

[0005]

[0002] This disclosure relates to biodiesel fuel compositions and methods of using the same. More specifically, this disclosure relates to biodiesel fuel compositions blended to reduce filter blocking tendency.

[0006] BACKGROUND

[0007]

[0003] Biodiesel, either as the sole fuel component or in a blend with petroleum diesel or paraffinic diesel component such as Hydro-processed Vegetable Oils (HVO) or Gas-To-Liquids (GTL) diesel, is often touted to reduce greenhouse emissions compared to conventional fuels.

[0008]

[0004] However, the use of biodiesel is not without challenges. For example, finished biodiesels can contain contaminants such as saturated monoglycerides (SMGs), or sterol glucosides (SGs), and others, that can precipitate from the finished blend and cause premature blocking or plugging of dispenser filters or vehicle fuel filters. The concentrations of these contaminants can depend on the particulars of the manufacturing process and the type of triglyceride feedstock used. Thus, the filter blocking tendency of biodiesel -containing fuels can vary considerably depending on where the biodiesel was sourced.

[0009] - 1 -

[0010] EMF US 86880356vl

[0005] Additionally, the fdter blocking can be exacerbated when biodiesel is blended with paraffinic components such as HVO, due to relatively poor solvent strength of the paraffinic component compared to biodiesel or petroleum diesel.

[0011]

[0006] A blocked vehicle filter will limit or stop fuel from reaching an engine. This can cause problems with starting the engine and a loss of power. In some cases, a blocked filter can cause an engine to shut down completely until the filter has been changed. A blocked dispenser filter can result in loss of revenue for a retailer by interrupting fuel sales, and increased frequency of filter replacement due to plugging by biodiesel contaminants increases maintenance expenditure.

[0012] SUMMARY OF THE INVENTION

[0013]

[0007] In one aspect, there is provided a method for reducing filter blocking tendency of a fuel composition comprising: biodiesel component; renewable diesel component or petroleum diesel component; wherein the method comprising dosing the fuel composition with imidazoline or diamine with hydrocarbyl ether substituent additive.

[0014]

[0008] In another aspect, there is provided the use of at least one imidazoline additive to reduce filter blocking tendency of fuel composition comprising biodiesel component and renewable biodiesel component.

[0015] DETAILED DESCRIPTION

[0016] Description

[0009] The present disclosure relates to blended fuel compositions that contain components of renewable diesel and biodiesel. The blended fuel composition includes at least one imidazoline compound which reduces the fdter blocking tendency of the blended fuel composition.

[0017]

[0010] In one aspect, the present disclosure relates to a method of reducing filter blocking tendency of a fuel which comprises a biodiesel component and a renewable diesel component. The method comprises the step of dosing at least one imidazoline additive to the fuel.

[0018] [Oi l] In another aspect, the present disclosure relates to the use of at least one imidazoline compound in a blended fuel composition which includes components of renewable diesel and biodiesel to reduce the filter blocking tendency of the blended fuel composition.

[0019]

[0012] In some embodiments, the fuel composition may include conventional diesel (or “petroleum diesel”) or conventional diesel components. In some embodiments, the fuel composition may include synthetic diesel or synthetic diesel components.

[0020] Biodiesel Components

[0021]

[0013] The fuel composition of the present disclosure includes at least one component of biodiesel.

[0022]

[0014] Biodiesel is a diesel fuel that has been derived from biological sources such as vegetable oils or animal fats. Biodiesel is produced by transesterification process which converts organic fats and oils into fatty acid alkyl esters by reacting them with alcohols and catalysts.

[0023]

[0015] The compositional make up of diesel can vary depending on the source. Generally speaking, commonly found components of biodiesel include, but are not limited to, fatty acid ester(s), along with minor amounts of impurities such as glycerol, soap(s), alcohol(s), and the like.

[0016] Typically, fatty acid ester(s) is the main or most abundant component of biodiesel. The fatty acid group of the fatty acid ester can vary. Examples of fatty acid groups include the following: dodecanoic acid; tetradecanoic acid; cis-9-tetradecanoic acid; hexadecenoic acid; cis- 9-hexadecanoic acid; octadecanoic acid; cis-9-octadecaoic acid; cis,cis-9,12-octadecadienoic acid; cis,cis,cis-9,12,15-octadecatrienoic acid; eicosanoic acid; cis-11-eicosenoic acid; docosanoic acid; cis-13-docosenoic acid; and the like.

[0024]

[0017] Biodiesel may include contaminants or impurities which can lead to filter blocking. Two major families of such contaminants or impurities include saturated monoglycerides (SMGs), or sterol glucosides (SGs), though other types of contaminants found in biodiesel may contribute to filter blocking, including proteins, fatty acids, wax esters, and others.

[0025]

[0018] Non-limiting examples of SMGs include 1 -monopalmitoylglycerol, 2- monopalmitoylglycerol, 1-mono-stearoylglycerol, and the like. Non-limiting examples of SGs include b-sitosteryl glucoside, campesteryl glucoside, and the like.

[0026] Renewable Diesel Components

[0027]

[0019] The fuel composition of this disclosure includes one or more renewable diesel components. Renewable diesel is a fuel made from a biological source such as fats and oils (e.g., soybean or canola oil) and is processed to be equivalent or nearly equivalent to petroleum diesel in its application.

[0028]

[0020] Renewable diesel is sometimes referred to as hydro-processed vegetable oil (HVO) or green diesel and can be produced via one of several production processes. These processes can include hydroprocessing or hydrotreating.

[0021] "Hydroprocessing" or "hydrotreating" refers to processes or treatments that react a carbon-based material with hydrogen, typically underpressure and with a catalyst. Such processes include, but are not limited to, hydrodeoxygenation (of oxygenated species), hydrotreatment, hydrocracking, and hydroisomerization. For examples of such processes, see Cash et al., U.S. Patent 6,630,066; and El omari, United States Patent 6,841,063. The embodiments of the present invention utilize such hydroprocessing to convert triglycerides to paraffins.

[0029] Petroleum Diesel and Synthetic Diesel

[0030]

[0022] The biodiesel fuel of this disclosure may be blended with petroleum diesel. Petroleum diesel (sometimes referred to as petrodiesel, fossil diesel, or mineral diesel) contain hydrocarbons that boil between approximately 150 °C and 350 °C at atmospheric pressure, and originate from crude oil or processed derivatives thereof, containing a distribution of carbon atoms predominantly ranging from approximately 10 to 28 carbon atoms per molecule.

[0031]

[0023] The biodiesel fuel of this disclosure may be blended with synthetic diesel. Synthetic diesel is typically produced form carbonaceous materials such as biomass, biogas, natural gas, coal, and the like, wherein the raw material is gasified into synthesis gas and converted to synthetic diesel via, for example, Fischer-Tropsch process.

[0032] Imidazoline Compound

[0033]

[0024] The additive composition includes at least one imidazoline compound. The at least one imidazoline compound may be present in about 50 ppmw to about 50,000 ppmw based on the total fuel composition, such as from 50 ppmw to 25,000 ppmw, 50 ppmw to 10,000 ppmw, 100 ppmw to 50,000 ppmw, 100 ppmw to 25,000 ppmw, 100 ppmw to 10,000 ppmw, and the like.

[0025] The imidazoline compound can be represented by the following generalized structure:

[0034] Structure I wherein R1is saturated or unsaturated hydrocarbyl group having 10 to 30 carbon atoms and R2is an aminoalkyl, poly aminoalkyl, or aminoether group having 2 to 40 carbon atoms.

[0035]

[0026] The imidazolines can be obtained by any compatible means. For example, imidazolines can be formed by cyclic condensation of a carboxylic acid with substituted 1,2- diaminoethanes. Suitable carboxylic acids useful in preparing the imidazoline include oleic acid, stearic acid, isostearic acid, or mixtures of fatty acids derived from a natural oil such as tall oil, and the like. Suitable 1,2-diaminoethane compounds may have the following generalized structure:

[0036] R— NH— C2H4— NH2where R is a hydrocarbyl group or a substituted hydrocarbyl group

[0037]

[0027] Specific non-limiting examples of imidazoline compound include the following:

[0038]

[0039] Structure IV

[0040]

[0028] The following examples are presented to exemplify embodiments but are not intended to limit the application to the specific embodiments set forth.

[0041] Other Additives

[0042]

[0029] The fuel composition may comprise other generally known fuel additives. Suitable examples include, but are not limited to, antioxidants, metal deactivators, demulsifiers, oxygenates, cetane improvers, dispersants, and detergents. In diesel fuel, other well-known additives can be employed such as pour point depressants, flow improvers, and the like.

[0043]

[0030] Each of the foregoing additives, when used, is used at a functionally effective amount to impart the desired properties to the fuel composition. Generally, the concentration of each of these additives, when used, may range, unless otherwise specified, from about 50 ppmw to about 20 wt. %, such as about 0.01 to about 10 wt. %.

[0044] EXAMPLES

[0045]

[0031] The following examples are intended for illustrative purposes only and do not limit in any way the scope. Description of the examples and their test results are provided below.

[0032] The examples include biodiesel blended with HVO (20% biodiesel) and dosed imidazoline compound(s).

[0046]

[0033] Example 1 includes a mixture obtained by the reaction of isostearic acid and tetraethylenepentamine (TEPA) in 3.15: 1 molar ratio. The mixture includes the imidazoline compound shown as Structure II above, among others.

[0047]

[0034] Example 2 includes a mixture obtained by the reaction of tall oil fatty acid and diethylene triamine. The mixture includes the fatty acid imidazolines shown as Structure III (derived from oleic acid) and Structure IV (derived from linoleic acid), among others.

[0048] Biodiesel Filterability Data

[0049]

[0035] The samples were cold soaked following a Cold Soak Filter Blocking Tendency Test procedure (CAN / CGSB-3.0 no. 142.0-2019), wherein the samples were cold soaked for about 16 hours at ~1°C and then brought to ambient temperature prior to fdterability testing. Cold soaking can cause undesirable components (e.g., saturated monoglycerides or sterol glucosides) to precipitate.

[0050]

[0036] The Filter Blocking Tendency (FBT) was then determined according to ASTM D2068 using Procedure B (Whatman Puradisc™ -13 mm diameter GF / A -1.6 mm glass microfibre syringe filter). Test results are summarized in the table below.

[0051] A reduced score indicates improvement of filterability (less severe filter plugging), with 1.00 being the best possible score (no measurable filter plugging).

[0052]

[0037] It will be understood that various modifications may be made to the embodiments disclosed herein. Therefore, the above description should not be construed as limiting, but merely as exemplifications of embodiments of the invention. For example, the functions described above and implemented for operating are for illustration purposes only. Other arrangements and methods may be implemented by those skilled in the art without departing from the scope and spirit of this application. Moreover, those skilled in the art will envision other modifications within the scope and spirit of the claims appended hereto.

Claims

CLAIMS1. A method for reducing filter blocking tendency of a fuel composition comprising: biodiesel component; renewable diesel component or petroleum diesel component; wherein the method comprising dosing the fuel composition with imidazoline or diamine with hydrocarbyl ether substituent additive.

2. The method of claim 1, wherein the petroleum diesel component includes hydrocarbons from crude oil or processed derivatives thereof, wherein the hydrocarbon boils from about 150 °C to 350 °C at atmospheric pressure and wherein majority of the hydrocarbons includes carbon atoms ranging from approximately 10 to 28 carbon atoms per molecule.

3. The method of claim 1, wherein the biodiesel component is a fatty acid ester.

4. The method of claim 3, wherein the fatty acid ester is derived from methanol, ethanol, propanol, isopropanol, or butanol.

5. The method of claim 3, wherein the fatty acid group of the fatty acid ester comprises dodecanoic acid; tetradecanoic acid; cis-9-tetradecanoic acid; hexadecenoic acid; cis-9- hexadecanoic acid; octadecanoic acid; cis-9-octadecaoic acid; cis-9,12-octadecadienoic acid; cis- 9,12,15-octadecatrienoic acid; eicosanoic acid; cis-11-eicosenoic acid; docosanoic acid; or cis-13- docosenoic acid.

6. The method of claim 1, wherein the imidazoline additive is present in about 50 ppmw to about 5.0 wt.% based on the total fuel composition.

7. The method of claim 1, wherein the imidazoline additive is represented by the following generalized structure:wherein R1is saturated or unsaturated hydrocarbyl group having 10 to 30 carbon atoms and R2is a aminohydrocarbyl, polyaminohydrocarbyl, hydroxy hydrocarbyl, hydroxy ether, or aminoether having 2 to 40 carbon atoms8. The method of claim 1, wherein the fuel composition further comprises a saturated monoglyceride (SMGs), sterol glucoside (SGs), protein, glycerol, soap, wax ester, or alcohol.

7. The method of claim 6, wherein the saturated monoglyceride is 1 -monopalmitoylglycerol, 2-monopalmitoylglycerol, or 1-mono-stearoylglycerol.

8. The method of claim 6, wherein the sterol glucoside is > -sitosteryl glucoside or campesteryl glucoside.

9. The method of claim 1, wherein the renewable diesel component is hydro-processed vegetable oil.

10. The method of claim 9, wherein the hydro-processed vegetable oil comprises octadecane, 2-methylheptadecane, 3 -methylheptadecane, 2,14-dimethylhexadecane, 2,15- dimethylhexadecane, 3,14-dimethylhexadecane, heptadecane, 2-methylhexadecane, 3- methylhexadecane, 2, 13 -dimethylpentadecane, 2,14-dimethylpentadecane, 3,13- dimethylpentadecane, hexadecane, 2-methylpentadecane, 3-methylpentadecane, 2,12- dimethyltetradecane, 2, 13 -dimethyltetradecane, 3,12-dimethyltetradecane, petadecane, 2- methyltetradecane, 3-methyltetradecane, 2,11 -dimethyltridecane, 2,12-dimethyltridecane, or 3,11- di m ethy 1 tri decane .

10. The method of claim 1, wherein the fuel composition further comprises synthetic diesel.

11. The method of claim 10, wherein the synthetic diesel comprises a hydrocarbon mixture produced from synthesis gas via the Fischer-Tropsch process.

12. The method of claim 10, wherein the synthetic diesel has been isomerized, hydrocracked, hydrotreated, or fractionated.

13. The use of at least one imidazoline additive to reduce fdter blocking tendency of fuel composition comprising biodiesel component and renewable biodiesel component.

Images