# US 12,179,129 B2 · Synergetic solvent for crude oil emulsion breakers > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 12,179,129 B2 - Document ID: US12179129B2 - Status: Granted - Kind: B2 - Application number: 17/550,804 - Filed: 2021-12-14 - Published: 2023-09-21 - Granted: 2024-12-31 - Earliest claimed: 2021-12-14 - Assignees: Saudi Arabian Oil Company - Applicants: Saudi Arabian Oil Company - Inventors: Guillaume Robert Jean-Francois Raynel; Mustafa Al-Talaq - Web page: https://patentgrep.com/patent/US12179129B2 ## CPC - B01D 17/047: {with separation aids} - C08G 61/02: Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes - C10G 33/04: with chemical means - C10L 10/00: Use of additives to fuels or fires for particular purposes (additives for liquid carbonaceous fuels characterised by their chemical nature C10L1/10; using binders for briquetting solid fuels C10L5/10; using additives to improve the combustion of solid fuels C10L9/10) - C08G 2261/1412: Saturated aliphatic units - C08G 2261/1424: containing ether groups, including alkoxy - C08G 2261/90: Applications - C10G 31/08: by treating with water - C10L 2300/00: Mixture of two or more additives covered by the same group of C10L1/00 - C10L1/308 - B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28) - C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS - C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES - C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS ## Abstract This disclosure relates to demulsifier compositions containing one or more demulsifying polymers and an alkyl carboxylic acid solvent, and methods of using the compositions for separating water-in-oil emulsions. ## Claims ### Claim 1 A demulsifier composition, comprising: about 25 wt % to about 45 wt % of a demulsifying polymer; and about 30 wt % to about 60 wt % of a solvent, wherein the solvent is an alkyl carboxylic acid having an alkyl chain of 1 to 8 carbon atoms, a pKa of about 2 to about 7, and a Kow greater than about 0.1. ### Claim 2 (depends on 1) The demulsifier composition of claim 1, wherein the demulsifying polymer is an alkoxylated phenolic polymer or an alkoxylated polyalcohol. ### Claim 3 (depends on 2) The demulsifier composition of claim 2, wherein the alkoxylated phenolic polymer is para-substituted with a saturated hydrocarbon chain. ### Claim 4 (depends on 3) The demulsifier composition of claim 3, wherein the saturated hydrocarbon chain is selected from para-tertiary-alkyl, para-secondary-alkyl, para-iso-alkyl, para-cycloalkyl, and para-n-alkyl. ### Claim 5 (depends on 3) The demulsifier composition of claim 3, wherein the saturated hydrocarbon chain is selected from para-tertiary-butylphenol, para-tertiary-amylphenol, para-tertiary-hexylphenol, and para-tertiary-heptylphenol. ### Claim 6 (depends on 2) The demulsifier composition of claim 2, wherein the alkoxylated phenolic polymer has the structure: wherein: R is a saturated hydrocarbon chain having between 1 and 8 carbons; R′ and R″ are each independently selected from H and C1-C2 alkyl; wherein the total number of carbon atoms in R, R′, and R″ is between 3 and 8; PPO is polypropylene oxide having the formula: PEO is polyethylene oxide having the formula: x is an integer between 0 and 10; y is an integer between 0 and 10; and n is an integer between 3 and 10. ### Claim 7 (depends on 6) The demulsifier composition of claim 6, wherein the demulsifying polymer has the structure: ### Claim 8 (depends on 1) The demulsifier composition of claim 1, wherein the demulsifying polymer has the structure: ### Claim 9 (depends on 1) The demulsifier composition of claim 1, wherein the demulsifier composition comprises about 30 wt % to about 40 wt % demulsifying polymer. ### Claim 10 (depends on 1) The demulsifier composition of claim 1, wherein the demulsifier composition comprises about 45 wt % to about 55 wt % solvent. ### Claim 11 (depends on 1) The demulsifier composition of claim 1, wherein the alkyl chain of the alkyl carboxylic acid is linear or branched. ### Claim 12 (depends on 1) The demulsifier composition of claim 1, wherein the pKa of the solvent is about 3 to about 6. ### Claim 13 (depends on 1) The demulsifier composition of claim 1, wherein the alkyl carboxylic acid has a melting point of about 15° C. or lower. ### Claim 14 (depends on 1) The demulsifier composition of claim 1, wherein the alkyl carboxylic acid has a melting point of about 10° C. or lower. ### Claim 15 (depends on 1) The demulsifier composition of claim 1, wherein the alkyl carboxylic acid has a boiling point of about 80° C. or higher. ### Claim 16 (depends on 1) The demulsifier composition of claim 1, wherein the alkyl carboxylic acid has a boiling point of about 90° C. or higher. ### Claim 17 (depends on 1) The demulsifier composition of claim 1, wherein the solvent is an alkyl carboxylic acid having an alkyl chain of 1 to 8 carbon atoms, a pKa between about 2 and about 7, a Kow greater than about 0.1, a melting point of about 15° C. or lower, and a boiling point of about 80° C. or higher. ### Claim 18 (depends on 1) The demulsifier composition of claim 1, wherein the solvent is an alkyl carboxylic acid having an alkyl chain of 1 to 8 carbon atoms, a pKa between about 3 and about 6, a Kow greater than about 0.1, a melting point of about 10° C. or lower, and a boiling point of about 90° C. or higher. ### Claim 19 (depends on 1) The demulsifier composition of claim 1, further comprising a clarifier. ### Claim 20 (depends on 19) The demulsifier composition of claim 19, wherein the clarifier is selected from 1,2,4-trimethylbenzene, naphthalene, and combinations thereof. ### Claim 21 (depends on 19) The demulsifier composition of claim 19, wherein the clarifier comprises about 0.1 wt % to about 10 wt % of the demulsifier composition. ### Claim 22 (depends on 1) A method of dewatering a water-in-oil emulsion, comprising adding the demulsifier composition according to claim 1 to a water-in-oil emulsion and separating the water from the emulsion. ### Claim 23 (depends on 22) The method of claim 22, wherein the water-in-oil emulsion is a crude oil emulsion. ### Claim 24 (depends on 23) The method of claim 23, wherein the crude oil emulsion is a refinery desalting emulsion. ### Claim 25 (depends on 23) The method of claim 23, wherein the crude oil emulsion is a crude oil production emulsion. ### Claim 26 (depends on 1) A method of treating produced petroleum comprising an emulsion, the method comprising contacting the produced petroleum comprising the emulsion with the demulsifier composition according to claim 1 to reduce or eliminate the emulsion.