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WO2025184584A1 - Désémulsifiants pour charges renouvelables - Google Patents

Désémulsifiants pour charges renouvelables

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Publication number
WO2025184584A1
WO2025184584A1 PCT/US2025/017962 US2025017962W WO2025184584A1 WO 2025184584 A1 WO2025184584 A1 WO 2025184584A1 US 2025017962 W US2025017962 W US 2025017962W WO 2025184584 A1 WO2025184584 A1 WO 2025184584A1
Authority
WO
WIPO (PCT)
Prior art keywords
reaction products
ppma
derivative
sulfonate
sulfonic acid
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
PCT/US2025/017962
Other languages
English (en)
Inventor
Roberto Gutierrez
Hitesh Bagaria
Nimeshkumar PATEL
Jenee ZARAGOZA
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BL Technologies Inc
Original Assignee
BL Technologies Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BL Technologies Inc filed Critical BL Technologies Inc
Publication of WO2025184584A1 publication Critical patent/WO2025184584A1/fr
Pending legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G33/00—Dewatering or demulsification of hydrocarbon oils
    • C10G33/04—Dewatering or demulsification of hydrocarbon oils with chemical means
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D17/00—Separation of liquids, not provided for elsewhere, e.g. by thermal diffusion
    • B01D17/02—Separation of non-miscible liquids
    • B01D17/04—Breaking emulsions
    • B01D17/047—Breaking emulsions with separation aids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10G—CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION; RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
    • C10G31/00—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for
    • C10G31/08—Refining of hydrocarbon oils, in the absence of hydrogen, by methods not otherwise provided for by treating with water

Definitions

  • the disclosed technology relates to demulsifier compositions and methods of use thereof.
  • the disclosed technology relates to demulsifier compositions comprising one or more dispersants, and methods of use thereof.
  • renewable feedstocks used in the fuel production industry, contain high amounts of metals and other contaminants. Removal of metals from these renewable feedstocks is a major concern. These metals poison the catalyst of hydrotreaters and lower run times. To remove these metals, pretreatment processes where the renewable feedstock is washed with low pH water ( ⁇ 2 pH) is traditionally done to remove these contaminants. This “washing” step is done by mixing both water and feed with high shear rates resulting in an emulsion that is difficult to resolve. Since these renewable feedstocks are different in nature than conventional crude oils, standard demulsifiers such as resin alkoxylates work poorly. Additionally, since these renewable feedstocks do not have the standard emulsion stabilizing surfactants found in crude oil, different types of demulsifiers are needed.
  • the disclosed technology provides for demulsifier compositions for resolving emulsions in renewable feedstocks used in renewable fuel production processes, the demulsifier compositions comprising one or more dispersants.
  • Various aspects of the disclosure relate to a demulsifier composition for resolving emulsions in a renewable feedstock, the demulsifier composition comprising one or more dispersants.
  • Various aspects of the disclosure additionally relate to a method of resolving emulsions in a renewable feedstock, the method comprising adding to the renewable feedstock a demulsifier composition comprising one or more dispersants.
  • Various aspects of the disclosure further relate to a method of removing contaminants from a renewable feedstock, the method comprising treating the renewable feedstock with a low pH water to create an emulsion; and adding to the emulsion a demulsifier composition comprising one or more dispersants.
  • FIG. 1 illustrates the improved water content of a renewable vegetable feedstock after treatment with embodiments of the demulsifier composition of the disclosure, wherein the demulsifier compositions includes a sulfonate derivative or a combination of a sulfonate derivative and a succinic acid derivative, as compared to untreated example renewable feedstock.
  • FIG. 2 illustrates the improved water content of a renewable vegetable feedstock after treatment with an embodiment of the demulsifier composition of the disclosure, wherein the demulsifier composition includes a sulfonate derivative, as compared to untreated example renewable feedstock, and example renewable feedstock treated with other demulsifiers known in the art.
  • FIG. 3 illustrates the improved water content of a renewable vegetable/tallow feedstock after treatment with an embodiment of the demulsifier composition of the disclosure, wherein the demulsifier composition includes a succinic acid derivative, as compared to untreated example renewable feedstock, and example renewable feedstock treated with other demulsifiers known in the art.
  • FIG. 4 illustrates the improved free water content of a renewable tallow feedstock emulsion with a wash water treated with an embodiment of the demulsifier composition of the disclosure, wherein the demulsifier composition includes a sulfonate derivative, as compared to an untreated sample and demulsifiers known in the art.
  • “Optional” or “optionally” means that the subsequently described event or circumstance may or may not occur, or that the subsequently identified material may or may not be present, and that the description includes instances where the event or circumstance occurs or where the material is present, and instances where the event or circumstance does not occur or the material is not present.
  • the disclosed technology provides for demulsifier compositions for resolving emulsions in renewable feedstocks used in renewable fuel production processes comprising one or more dispersants.
  • compositions and methods disclosed herein have been found to be effective in resolving emulsions and lowering the water content in renewable feedstocks. More specifically, it was found that dispersants, for example those that include sulfonate chemistries, succinic acid-based chemistries and combinations thereof, effectively lowered the water content in the effluent feed after mixing.
  • the term “demulsifier” refers to a chemical substance or formulation used to break down and separate emulsions.
  • emulsion refers to a mixture of two immiscible liquids, such as oil and water, stabilized by an emulsifying agent.
  • renewable feedstock refers to raw materials or substances derived from sustainable, replenishable sources that can be used as inputs for various industrial processes.
  • the demulsifier composition may include one or more dispersants.
  • the one or more dispersants may be selected from a sulfonate derivative; a sulfonic acid derivative, including, but not limited to a hydrocarbyl derivative of sulfonic acid; a sulfo-alkanoate; a sulfo succinate; a sulfate derivative; a succinic acid derivative, alkenyl thiopho sphonic acid and its reaction products with polyhydric alcohols; alkenyl phosphonate; reaction products of fatty acids and polyamine; reaction products of fatty acids, formaldehyde and polyamine; reaction products of fatty acid and hydroxylated amine; reaction products of alkylphenol and formaldehyde; reaction products of alkylphenol, formaldehyde and polyamine;
  • a hydrocarbyl derivative of sulfonic acid includes, but is not limited to, an alkyl derivative of sulfonic acid, a cycloalkyl derivative of sulfonic acid, or an aryl derivative of sulfonic acid.
  • the hydrocarbyl derivative of sulfonic acid is a naphthyl derivative of sulfonic acid.
  • the demulsifier composition may comprise a mixture of a sulfonate derivative and a succinic acid derivative.
  • suitable sulfonate derivatives may include any sulfonate derivative capable of resolving emulsions generated during processing of renewable feedstocks.
  • suitable sulfonate derivatives may include metal, ammonium or amine salts of alkyl sulfonate; metal, ammonium or amine salts of aryl sulfonate; hydrocarbyl sulfonates; and mixtures thereof.
  • suitable succinic acid derivatives may include any succinic acid derivative capable of resolving emulsions generated during processing of renewable feedstocks.
  • suitable succinic acid derivatives may include alkenyl succinic acids or anhydride; alkenyl succinic acid or anhydride reaction products with polyamines; alkenyl succinic acid reaction products with polyhydric alcohols; reaction products of alkene, maleic anhydride and polyamines; reaction products of alkene, maleic anhydride and polyols; reaction products of alkene, maleic anhydride and alkanolamines; and mixtures thereof.
  • the succinic acid derivative includes a polyisobutylene succinimide.
  • the dispersant includes dodecylbenzenesulfonic acid, sodium 2-ethyl hexyl sulfate, sodium (Cio-Ci3)-alkyl benzene sulfonate, sodium (Cu-Cie)- olefin sulfonate, alkyl aryl sulfonic acid, alkyl cylcoalkyl sulfonic acid, ammonium alcohol (Ce-Cio) ether sulfonate, or polyisobutylene succinimide.
  • the alkyl aryl sulfonic acid includes a dialkyl aryl sulfonic acid.
  • the “aryl” group in the alkyl aryl sulfonic acid is benzene.
  • the alkyl aryl sulfonic acid is a (C3-C3o)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a (C3-Ci6)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a (C6-Ci6)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a di-(C3-C3o)-alkyl aryl sulfonic acid. In another embodiment, the alkyl aryl sulfonic acid is a di-(C3-Ci6)-alkyl aryl sulfonic acid. In another embodiment, the alkyl aryl sulfonic acid is a di-(C6-Ci6)-alkyl aryl sulfonic acid. In one embodiment, the alkyl aryl sulfonic acid is a dodecyl benzene sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid includes a dialkyl cycloalkyl sulfonic acid.
  • the “cycloalkyl” group in the alkyl cycloalkyl sulfonic acid is naphthalene.
  • the alkyl cycloalkyl sulfonic acid is a (C3- C3o)-alkyl cycloalkyl sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid is a (C3-Ci6)-alkyl cycloalkyl sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid is a (C6-Ci6)-alkyl cycloalkyl sulfonic acid. In one embodiment, the alkyl cycloalkyl sulfonic acid is a di-(C3-C3o)-alkyl cycloalkyl sulfonic acid. In another embodiment, the alkyl cycloalkyl sulfonic acid is a di-(C3-Ci6)-alkyl cycloalkyl sulfonic acid. In one embodiment, the alkyl cycloalkyl sulfonic acid is diisopropyl naphthalene sulfonic acid.
  • the demulsifier composition includes a dodecylbenzenesulfonic acid and a polyisobutylene succinimide.
  • the one or more dispersants may be present in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 10 pp
  • the dispersants may be present in an amount of about 10 ppmA to about 200 ppmA. In another embodiment, the dispersants may be present in an amount of about 20 ppmA to about 160 ppmA. In another embodiment, the dispersants may be present in an amount of about 10 ppmA to about 50 ppmA.
  • the sulfonate derivative may be present in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 1
  • the sulfonate derivative may be present in an amount of about 1 ppmA to about 60 ppmA. In another embodiment, the sulfonate derivative may be present in an amount of about 10 ppmA to about 60 ppmA. In another embodiment, the sulfonate derivative may be present in an amount of about 10 ppmA to about 50 ppmA.
  • the succinic acid derivative may be present in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 5000 pp
  • the demulsifier compositions of the disclosed technology may further comprise one or more resin alkoxylates.
  • suitable resin alkoxylates may include polyetheramine-based resin alkoxylates, polyol-based resin alkoxylates, epoxy-based resin alkoxylates, polyamine-based resin alkoxylates, and the like, or mixtures thereof.
  • the demulsifier compositions of the disclosed technology may further comprise a suitable carrier solvent.
  • Example carrier solvents may include nonaromatic carrier solvents such as terpenes, water, renewable naphtha, renewable diesel, dimethyl ester (e.g. DME-100), and the like, or mixtures thereof.
  • the demulsifier compositions of the disclosed technology may be used in a method of resolving emulsions in renewable feedstocks used in renewable fuel production processes. In other aspects, the demulsifier compositions of the disclosed technology may be used in a method of lowering the water content of renewable feedstocks used in renewable fuel production processes.
  • the methods may comprise adding to the renewable feedstock a demulsifier composition comprising one or more dispersants.
  • the one or more dispersants may be selected from a sulfonate derivative; a sulfonic acid derivative, including, but not limited to a hydrocarbyl derivative of sulfonic acid; a sulfo-alkanoate; a sulfosuccinate; a sulfate derivative; a succinic acid derivative, alkenyl thiopho sphonic acid and its reaction products with polyhydric alcohols; alkenyl phosphonate; reaction products of fatty acids and polyamine; reaction products of fatty acids, formaldehyde and polyamine; reaction products of fatty acid and hydroxylated amine; reaction products of alkylphenol and formaldehyde; reaction products of alkylphenol, formaldehyde and polyamine; and mixtures thereof.
  • a hydrocarbyl derivative of sulfonic acid includes, but is not limited to, an alkyl derivative of sulfonic acid, a cycloalkyl derivative of sulfonic acid, or an aryl derivative of sulfonic acid.
  • the hydrocarbyl derivative of sulfonic acid is a naphthyl derivative of sulfonic acid.
  • the demulsifier composition may comprise a mixture of a sulfonate derivative and a succinic acid derivative.
  • suitable sulfonate derivatives may include any sulfonate derivative capable of resolving emulsions generated during processing of renewable feedstocks.
  • suitable sulfonate derivatives may include metal, ammonium or amine salts of alkyl sulfonate; metal, ammonium or amine salts of aryl sulfonate; hydrocarbyl sulfonates; and mixtures thereof.
  • suitable succinic acid derivatives may include any succinic acid derivative capable of resolving emulsions generated during processing of renewable feedstocks.
  • suitable succinic acid derivatives may include alkenyl succinic acids or anhydride; alkenyl succinic acid or anhydride reaction products with polyamines; alkenyl succinic acid reaction products with polyhydric alcohols; reaction products of alkene, maleic anhydride and polyamines; reaction products of alkene, maleic anhydride and polyols; reaction products of alkene, maleic anhydride and alkanolamines; and mixtures thereof.
  • the succinic acid derivative includes a polyisobutylene succinimide.
  • the dispersant includes dodecylbenzenesulfonic acid, sodium 2-ethyl hexyl sulfate, sodium (Cio-Ci3)-alkyl benzene sulfonate, sodium (Cu-Cie)- olefin sulfonate, alkyl aryl sulfonic acid, alkyl cylcoalkyl sulfonic acid, ammonium alcohol (Ce-Cio) ether sulfonate, or polyisobutylene succinimide.
  • the alkyl aryl sulfonic acid includes a dialkyl aryl sulfonic acid.
  • the “aryl” group in the alkyl aryl sulfonic acid is benzene.
  • the alkyl aryl sulfonic acid is a (C3-C3o)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a (C3-Ci6)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a (C6-Ci6)-alkyl aryl sulfonic acid.
  • the alkyl aryl sulfonic acid is a di-(C3-C3o)-alkyl aryl sulfonic acid. In another embodiment, the alkyl aryl sulfonic acid is a di-(C3-Ci6)-alkyl aryl sulfonic acid. In another embodiment, the alkyl aryl sulfonic acid is a di-(C6-Ci6)-alkyl aryl sulfonic acid. In one embodiment, the alkyl aryl sulfonic acid is a dodecyl benzene sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid includes a dialkyl cycloalkyl sulfonic acid.
  • the “cycloalkyl” group in the alkyl cycloalkyl sulfonic acid is naphthalene.
  • the alkyl cycloalkyl sulfonic acid is a (C3- C3o)-alkyl cycloalkyl sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid is a (C3-Ci6)-alkyl cycloalkyl sulfonic acid.
  • the alkyl cycloalkyl sulfonic acid is a (C6-Ci6)-alkyl cycloalkyl sulfonic acid. In one embodiment, the alkyl cycloalkyl sulfonic acid is a di-(C3-C3o)-alkyl cycloalkyl sulfonic acid. In another embodiment, the alkyl cycloalkyl sulfonic acid is a di-(C3-Ci6)-alkyl cycloalkyl sulfonic acid. In one embodiment, the alkyl cycloalkyl sulfonic acid is diisopropyl naphthalene sulfonic acid.
  • the demulsifier composition includes a dodecylbenzenesulfonic acid and a polyisobutylene succinimide.
  • the one or more dispersants may be added in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 10 pp
  • the dispersants may be present in an amount of about 10 ppmA to about 200 ppmA. In another embodiment, the dispersants may be present in an amount of about 20 ppmA to about 160 ppmA. In another embodiment, the dispersants may be present in an amount of about 10 ppmA to about 50 ppmA.
  • the sulfonate derivative may be present in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 1
  • the sulfonate derivative may be present in an amount of about 1 ppmA to about 60 ppmA. In another embodiment, the sulfonate derivative may be present in an amount of about 10 ppmA to about 60 ppmA. In another embodiment, the sulfonate derivative may be present in an amount of about 10 ppmA to about 50 ppmA.
  • the succinic acid derivative may be added in an amount of between about 0.1 ppmA to about 5000 ppmA, or about 0.1, 0.5, 1, 10, 50, 100, 200, 300, 400, 500, 600, 700, 800, 900, 1000, 1100, 1200, 1300, 1400, 1500, 1600, 1700, 1800, 1900, 2000, 2100, 2200, 2300, 2400, 2500, 2600, 2700, 2800, 2900, 3000, 3100, 3200, 3300, 3400, 3500, 3600, 3700, 3800, 3900, 4000, 4100, 4200, 4300, 4400, 4500, 4600, 4700, 4800, 4900, or 5000 ppmA, or about 1 ppmA to about 1000 ppmA or about 1 ppmA to about 500 ppmA, or about 10 ppmA to about 100 ppmA or about 100 ppmA to about 1000 ppmA or about 1 ppmA, or about 5000 pp
  • the demulsifier compositions of the disclosed technology may be used in a method of removing contaminants from a renewable feedstock, the method comprising treating the renewable feedstock with a low pH water to produce an emulsion; and adding to the emulsion a demulsifier composition comprising a sulfonate derivative, a succinic acid derivative, or mixtures thereof.
  • treating the renewable feedstock may comprise mixing the renewable feedstock with water, such as a low pH water.
  • the low pH water may be characterized by a pH of less than 7, or less than 6, less than 5, less than 4, less than 3, or less than 2.
  • treating the renewable feedstock may comprise mixing the renewable feedstock with water at a high shear rate.
  • the methods of the disclosure may be used to resolve emulsions in any type of renewable feedstock.
  • the methods may be used to resolve emulsions in renewable feedstocks that include plant or animal materials, such as plant oils or animal-based oils, or combinations thereof.
  • plant oils may include vegetable oils such as soybean oil, com oil, palm oil, or the like.
  • animal materials or animal-based oils may include animal fats, such as tallow, or animal wastes.
  • the renewable feedstock is a blend of soybean oil and tallow.
  • Other example feedstocks may include materials derived from industrial, agricultural, or municipal waste streams that can be repurposed as feedstocks.
  • Example 1 simulates a dewater process and resolve of a renewable feedstock and wash water in a vessel.
  • An example vegetable oil feedstock emulsion (25% by volume wash water) was prepared by blending the vegetable oil feedstock and wash water in a high speed blender at temperature and pressure.
  • the emulsion was treated with various embodiments of the demulsifier compositions of the disclosure, namely, (A) a blend of 40 ppmA of polyisobutylene succinimide (PIBSI) and 40 ppmA of dodecylbenzenesulfonic acid (DDBSA); (B) a blend of 40 ppmA of PIBSI and 60 ppmA of DDBSA; and (C) 20 ppmA of DDBSA.
  • PIBSI polyisobutylene succinimide
  • DBSA dodecylbenzenesulfonic acid
  • FIG. 1 illustrates that the demulsifier chemistries of the disclosure were effective in lowering the water content of the feedstock to less than 0.1% by volume.
  • Example 2 simulates a dewater process and resolve of a renewable feedstock and wash water in a vessel.
  • An example vegetable oil feedstock emulsion (25% by volume wash water) was prepared by blending the vegetable oil feedstock and wash water in a high speed blender at temperature and pressure. The emulsion was treated with various resin alkoxylate demulsifiers (comparative samples 1-6) at a dosage of 20 ppmA each, as shown in FIG. 2.
  • Resin Alkoxylate #1 is nonyl phenol resin ethoxylate and amyl resin ethoxylate
  • Resin Alkoxylate #2 is nonyl phenol resin ethoxylate
  • Resin Alkoxylate #3 is amyl resin ethoxylate
  • Resin Alkoxylate #4 is nonyl phenol resin ethoxylate and amyl resin ethoxylate
  • Resin Alkoxylate #5 is nonyl phenol resin ethoxylate
  • Resin Alkoxylate #6 is nonyl phenol resin ethoxylate and amyl resin ethoxylate.
  • Sample DDBSA is 20 ppmA of a sulfonate-based chemistry, Dodecylbenzenesulfonic acid, of the disclosure.
  • FIG. 2 illustrates that the sulfonate-based chemistry was the only demulsifier effective in lowering the water content of the feedstock to less than 0.1% by volume.
  • Example 3 simulates a dewater process and resolve of a renewable feedstock and wash water in a vessel.
  • An example vegetable oil and tallow blend feedstock emulsion (20% by volume wash water with a pH of 3) was prepared by blending the vegetable oil and tallow blend feedstock and wash water in a high speed blender at temperature and pressure.
  • the emulsion was treated with various comparative demulsifiers, including 15 ppmA of alkyl diol and 15 ppmA of a polyamine-based chemistry (Polyamine #2), as shown in FIG. 3, as well as 15 ppmA of a succinic acid-based chemistry, Polyisobutylene succinimide (PIBSI), of the disclosure.
  • PIBSI Polyisobutylene succinimide
  • FIG. 3 illustrates that the succinic acid-based chemistry was the most effective in lowering the water content of the feedstock as compared to the other demulsifiers tested.
  • a BTEX analysis was conducted for a sulfonate-based demulsifier of the disclosure. As shown in Table 1 below, the sulfonate-based demulsifier was also effective in removing hydrocarbons from the water phase of an example renewable feedstock.
  • Example 5 simulates a dewater process and resolve of a renewable feedstock and wash water in a vessel.
  • a soybean oil and tallow blend renewable feedstock emulsion was prepared by blending the soybean oil and tallow blend feedstock and wash water in a high speed blender at temperature and pressure.
  • the emulsion was treated with various embodiments of demulsifier compositions of the disclosure as shown in Table 2.
  • the renewable feedstock emulsion was left at temperature to resolve and the water content (volume %) remaining in the renewable feedstock for each sample, including a Blank, was measured. Results are shown in Table 2.
  • Example 6 simulates a dewater process and resolve of a renewable feedstock and wash water in a vessel.
  • a soybean oil renewable feedstock emulsion was prepared by blending the soybean oil and tallow blend feedstock and wash water in a high speed blender at temperature and pressure.
  • the emulsion was treated with various embodiments of demulsifier compositions of the disclosure as shown in Table 3.
  • the renewable feedstock emulsion was left at temperature to resolve and the water content (volume %) remaining in the renewable feedstock for each sample, including a Blank, was measured. Results are shown in Table 3.
  • a tallow renewable feedstock emulsion was prepared by blending the tallow feedstock and wash water having a pH of 4.2 in a high speed blender at temperature and pressure.
  • the emulsion was treated with an exemplary demulsifier, dodecylbenzenesulfonic acid (DDBSA) at a dosage amount of 50 ppmA.
  • the emulsion was also treated with resin alkoxylate demulsifiers (comparative samples 7 and 8) as provided in Example 2 at a dosage of 50 ppmA each.
  • Resin Alkoxylate #7 is butyl/nonyl phenol resin ethoxylate and nonyl resin ethoxylate and Resin Alkoxylate #8 is nonyl phenol resin ethoxylate, butyl phenol propoxylate/ethoxylate and nonyl/amyl resin ethoxylate.
  • the % volume of free water was measured in each emulsion sample, including a blank sample, and the data is shown in FIG. 4.
  • FIG. 4 shows that the DDBSA sample exhibited the highest % of free water compared with the comparative samples and the blank. Higher levels of free water in an emulsion are a measure of how well the emulsion will resolve and separate out the water from the feedstock.

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Production Of Liquid Hydrocarbon Mixture For Refining Petroleum (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)

Abstract

L'invention concerne une composition de désémulsifiant pour résoudre des émulsions dans des charges d'alimentation renouvelables. La composition de désémulsifiant comprend un ou plusieurs dispersants. L'invention concerne également un procédé d'abaissement de la teneur en eau dans une charge d'alimentation renouvelable et un procédé d'élimination de contaminants dans une charge d'alimentation renouvelable.
PCT/US2025/017962 2024-02-28 2025-02-28 Désémulsifiants pour charges renouvelables Pending WO2025184584A1 (fr)

Applications Claiming Priority (2)

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US202463558763P 2024-02-28 2024-02-28
US63/558,763 2024-02-28

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WO2025184584A1 true WO2025184584A1 (fr) 2025-09-04

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011065955A1 (fr) * 2009-11-30 2011-06-03 Momentive Performance Materials Inc. Compositions désémulsifiantes et procédés pour séparer des émulsions utilisant celles-ci
WO2013174631A1 (fr) * 2012-05-25 2013-11-28 Basf Se Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts
US20230295519A1 (en) * 2022-03-16 2023-09-21 Phillips 66 Company Methods for modifying desalter alkalinity capacity and uses thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011065955A1 (fr) * 2009-11-30 2011-06-03 Momentive Performance Materials Inc. Compositions désémulsifiantes et procédés pour séparer des émulsions utilisant celles-ci
WO2013174631A1 (fr) * 2012-05-25 2013-11-28 Basf Se Utilisation d'un produit réactionnel d'acides carboxyliques avec des polyamines aliphatiques pour l'amélioration ou l'augmentation de la séparation d'eau et de mazouts
US20230295519A1 (en) * 2022-03-16 2023-09-21 Phillips 66 Company Methods for modifying desalter alkalinity capacity and uses thereof

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