# US 7,612,117 B2 · Emulsion breaking process > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 7,612,117 B2 - Document ID: US7612117B2 - Status: Granted - Kind: B2 - Application number: 11/281,532 - Filed: 2005-11-17 - Published: 2007-05-17 - Granted: 2009-11-03 - Earliest claimed: 2005-11-17 - Assignees: General Electric Company - Inventors: Cato R. McDaniel; Alan E. Goliaszewski; David Birenbaum Engel - Web page: https://patentgrep.com/patent/US7612117B2 ## CPC - C10G 33/04: with chemical means - 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 ## Abstract The invention pertains to the use of a class of acetylenic surfactants to resolve or break water and oil emulsions. The surfactants are of particular advantage in resolving crude oil emulsions of the type encountered in desalter and similar apparatus designed to extract brines from the crude as they partition to the aqueous phase in the desalter. ## Claims ### Claim 1 A method of resolving a crude oil containing emulsion that includes an oil phase and an aqueous phase comprising contacting said crude oil emulsion with an amount of between about 1 to 1,000 ppm of an acetylenic surfactant compound or compounds selected from the groups Ia and Ib, wherein said Group Ia has the formula and wherein said Group Ib has the formula wherein R is —(CH2—CH2)—; R5 is —(CH2(CH3)CH)—or —(CH2—CH2—CH2)—; R1 and R4 are a straight or a branched chain alkyl having from about 3 to 10 C atoms or an aryl group; R2 and R3 are H, an alkyl chain having 1 to 5 C atoms or aryl group, and m, n, p, and q are numbers that range from about 0 to about 30, said method further comprising contacting said crude oil emulsion with another surfactant (II) wherein said surfactant (II) is a polyol having the formula wherein the moieties x, y, and z are each at least 1 and are such as to provide the compound with a molecular weight of about 500 or higher. ### Claim 2 (depends on 1) Method as recited in claim 1 wherein said emulsion is formed in a desalting apparatus. ### Claim 3 (depends on 1) Method as recited in claim 1 wherein said emulsion is a bitumen emulsion. ### Claim 4 (depends on 1) Method as recited in claim 1 wherein said emulsion is a slop oil emulsion. ### Claim 5 (depends on 1) Method as recited in claim 1 wherein said emulsion comprises water, oil, and sand. ### Claim 6 (depends on 1) Method as recited in claim 1 wherein said emulsion is located in a heater treater apparatus, free water knockout apparatus, inclined plate separator apparatus, or a water separator apparatus. ### Claim 7 (depends on 1) Method as recited in claim 1 wherein said emulsion is located in hydrocyclone or centrifuge. ### Claim 8 (depends on 1) Method as recited in claim 1 wherein said emulsion is a drilling mud emulsion. ### Claim 9 (depends on 8) Method as recited in claim 8 wherein said drilling mud emulsion is an inverted slop oil drilling mud emulsion. ### Claim 10 (depends on 8) Method as recited in claim 8 wherein said drilling mud emulsion results from leakage of drilling mud into produced crude oil. ### Claim 11 (depends on 1) Method as recited in claim 1 wherein said emulsion is a refinery slop oil emulsion. ### Claim 12 (depends on 1) Method as recited in claim 1 wherein said surfactant compound or compounds are chosen from the group consisting of a) 2, 4, 7, 9-tetramethyl-5-decyne-4,7-diol (TMDD-5) and b) 2, 5, 8, 11-tetramethyl-6-dodecyne-5,8-diol (TMDD-6) and ethoxylates and propylene oxide derivations of a) and b). ### Claim 13 (depends on 12) Method as recited in claim 12 wherein said surfactant compound is a). ### Claim 14 (depends on 12) Method as recited in claim 12 wherein said surfactant compound is an ethoxylate or propylene oxide capped ethoxylate of a). ### Claim 15 (depends on 1) Method as recited in claim 1 wherein said additional surfactant (II) has a molecular weight of from about 500 to about 30,000. ### Claim 16 (depends on 15) Method as recited in claim 15 wherein said x and z moieties of said additional surfactant (II) comprise about 20%-80% by weight of said additional surfactant. ### Claim 17 (depends on 16) Method as recited in claim 16 wherein said x and z moieties comprise about 40 percent by weight of said additional surfactant and said additional surfactant has a molecular weight of about 4,000. ### Claim 18 (depends on 1) Method as recited in claim 1 wherein said surfactant Ia, Ib, and II is brought into contact with said emulsion in a combined amount of 1 to 1,000 ppm based upon one million parts of said emulsion, and wherein said surfactant Ia, Ib is present in an amount of about 1-90 wt % based on the total weight of La, Ib, and II. ### Claim 19 A method of breaking a bitumen emulsion comprising contacting said bitumen emulsion with an effective amount of between about 1 about 500 ppm of an acetylenic surfactant compound or compounds selected from the groups Ia and Ib, wherein said Group Ia has the formula and wherein said Group lb has the formula wherein R is —(CH2—CH2)—; R5 is —(CH2(CH3)CH)— or —(CH2CH2CH2)—; R1 and R4 are a straight or a branched chain alkyl having from about 3 to 10 C atoms or an aryl group; R2 and R3 are H, an alkyl chain having 1 to 5 C atoms or aryl group, and m, n, p, and q are numbers that range from about 0 to about 30, and an additional surfactant II comprising a polyol having the formula wherein the moieties x, y, and z are each at least 1 and are such as to provide the compound with a molecular weight of about 500 or higher, said I and II in combination, being present in an amount of from about 1 to 1,000 ppm based upon one million parts of said emulsion. ### Claim 20 (depends on 19) Method as recited in claim 19 wherein said surfactant compound or compounds Ia or lb are chosen from the group consisting of a) 2, 4, 7, 9-tetramethyl-5-decyne-4,7-diol (TMDD-5) and b) 2, 5, 8, 11-tetramethyl-6-dodecyne-5,8-diol (TMDD-6) and ethoxylates and propylene oxide derivations of a) and b), and wherein said surfactant II has a molecular weight of from about 500 to about 30,000. ### Claim 21 (depends on 20) Method as recited in claim 20 wherein said x and z moieties of said additional surfactant (II) comprise about 20%-80% by weight of said additional surfactant. ### Claim 22 (depends on 21) Method as recited in claim 21 wherein said x and z moieties comprise about 40 percent by weight of said additional surfactant and said additional surfactant has a molecular weight of about 4,000.