[go: up one dir, main page]

US2597204A - Process for treating petroleum emulsions - Google Patents

Process for treating petroleum emulsions Download PDF

Info

Publication number
US2597204A
US2597204A US216474A US21647451A US2597204A US 2597204 A US2597204 A US 2597204A US 216474 A US216474 A US 216474A US 21647451 A US21647451 A US 21647451A US 2597204 A US2597204 A US 2597204A
Authority
US
United States
Prior art keywords
oxyalkylated
fatty acid
polyhydroxy compound
pounds
emulsion
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.)
Expired - Lifetime
Application number
US216474A
Inventor
Raymond W Todd
Fritz E Fuchs
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.)
Aquaness Corp
Original Assignee
Aquaness Corp
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 Aquaness Corp filed Critical Aquaness Corp
Priority to US216474A priority Critical patent/US2597204A/en
Application granted granted Critical
Publication of US2597204A publication Critical patent/US2597204A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

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

Definitions

  • This invention relates to the treatment of emulsions of mineral oil and water, particularly water-in-oil petroleum emulsions, for the purpose of separating the oil from the water.
  • An object of this invention is to provide an improved process for breaking or separating petroleum emulsions by subjecting such emulsions to the action of a novel demulsifying composition to be described in greater detail hereinafter.
  • Another object is the provision of a novel demulsifier composition which is highly effective for breaking or separating petroleum emulsions.
  • the new demulsifier in accordance with this invention comprises a class of esterification products obtained by the reaction of a fatty acid with a particular type of hydroxylated compound.
  • the hydroxylated compounds employed as the intermediates in forming the final esterification product are of a specific character obtained by the reaction of an alkyl polyhydroxy compound initially containing three or more free hydroxyl groups with an oxyalkylating material consisting essentially of mixtures of ethylene oxide and propylene oxide in particular proportions.
  • the aklyl polyhydroxy compounds which are particularly adapted for preparation of the intermediate materials employed in making the final demulsifier composition are best exemplified by the class consisting of glycerol, polyglycerol, pentaerythritol, sorbitol, mannitol and the like.
  • Polyglycerol is a polymer of glycerol, having in its simplest form, four free hydroxyl groups and a single ether linkage connecting two glyceryl residues as may be illustrated by the following formula:
  • the fatty acids employed in making the final ester product may be any of the well known long chain, soap-forming fatty acids having 8 to 18 carbon atoms in the chain, such as stearic, oleic, ricinoleic, soya bean fatty acids, tall oil, linseed oil fatty acids, cocoa-nut fatty acids, and the like.
  • the molal proportion of fatty acid to the oxyalkylated intermediate compounds may be varied to form either partial esters or fully esterified compounds or mixtures thereof.
  • the mono-, dior tri-ester compounds appear generally to be the more effective compounds.
  • the final ester compounds are all clear, moderately viscous liquids which are completely soluble or miscible with water in all proportions.
  • the procedure for oxyalkylating the polyhydroxy compounds is generally in accordance with well known procedures except that in every case the ethylene and propylene oxides are intermixed and reacted in mixed condition with the polyhydroxy material.
  • the resulting oxyalkylated polyhydroxy intermediates are then reacted in appropriate proportions with the selected fatty acid to. produce the desired ester products.
  • This esterifying reaction is conducted in accordance with well known procedures for efiecting esterification between a hydroxy compound and an acid.
  • OXYALKYLATED POLYHYDROXY INTERMEDIATE 46 pounds /2 mol) of glycerol, to which may be added about 4 pounds of sodium methylate as a catalyst, are placed in a Water-jacketed pressure chamber and heated to about 250 F. The chamber is purged with natural gas or methane and an atmosphere of such gas at a pressure of about 50 pounds per square inch is maintained in the chamber. 1250 pounds of ethylene oxide and 1250 pounds of propylene oxide are then pumped into the chamber, the oxides being intermixed as they are fed into the chamber. The oxides react with the glycerol and the resulting reaction tends to raise the temperature and pressure sharply.
  • External heating is cut off and by circulation of cooling water the temperature is maintained within a range of from about 270 to about 350 F.
  • the pressure is held to a range of from about to pounds per 3 square inch.
  • the pressure drops to about that of the blanketing gas, about 50 pounds per square inch, when the reaction is completed. About 3 to 4 hours is required to complete the reaction.
  • the proportions of materials used in-this' example will produce an oxyalkylated product having an average molecular weight of about 5000 and this product is a light colored, relatively lowviscosity liquid which is completely soluble-in cold water.
  • Example 2 About 187 pounds each of ethylene and'propylene oxides are used instead of 1250 pounds each as in Example 1, and will produce an oxyalkylated glycerol product having a molecular weight of about 7500.
  • Example 3 About 625 pounds each of ethylene and propylene oxides are used instead of the amounts'stated in the previous examples to produce an 'oxyalkylated product having a molecular weight of about 2500.
  • Example 4 83 pounds of polyglycerol are substitutedfor the 46 pounds of glycerol in each of Examples 1, 2 and 3, above.
  • Example 2 7500 pounds and 2500 pounds, respectively,of the Oxyalkylated Polyhydroxy Intermediates, Example 1 and Example 2, are substituted forthe 5000 pounds of Oxyalkylated Polyhydroxy Intel?- mediate, Example 1 in Final 'Ester Product, Example 1 above, to produce the corresponding mono-esters.
  • Example 3 564 pounds 2 mols) of oleic acid issubstituted for the 282 pounds in Final Ester Products, Examples l and 2, above, to produce the corresponding di-esters.
  • Example '4 350 pounds of tall oil are used in place of the 282 pounds of oleic acid in each or the Final-Ester Products, Examples 1 and 2 above,to produce the corresponding tall oil esters.
  • Example 5 700 pounds of tall oil are substituted in each case for the 564 pounds of oleic acid in Example 3 above.
  • soya bean fatty acids, stearic acid, or ricinoleic acid may be substituted for theoleic acid'an'dtall oil in each of the Final Ester ProductsfExa'mples 1, 2, 3, 4 and 5 above.
  • the demulsifier compositions employed in accordance with the present invention are fatty acid esters of a specific class of oxyalkylated polyhydroxy compounds, namely, aliphatic polyhydroxy compounds initially'having three0r more free hydroxyl groups whichhave been oxyalkylated with mixtures of ethylene and propylene oxides in the relative proportions stated above to produce compounds within the particular --ran'g'es of molecular weight above specified.
  • the emulsion to be treated may be brought in contactwith the emulsion to be treated in any of the numerous ways now-employed in the treatment of petroleum emulsions with chemical demulsifying agents, such, for example, as by introducing the treating agent into the well in which the emulsion-is produced, introducing the treating I agent into a conduit through which the emulsion is flowing, introducing the treating agent into a tank in which the emulsion is stored, *or introducing thetreat- 'ing agent into a container that holds a. sludge 'obtained from the bottom 'of an oil storage tank.
  • chemical demulsifying agents such, for example, as by introducing the treating agent into the well in which the emulsion-is produced, introducing the treating I agent into a conduit through which the emulsion is flowing, introducing the treating agent into a tank in which the emulsion is stored, *or introducing thetreat- 'ing agent into a container that holds a. sludge
  • the treating agent into a producing-well in such a way that it will b'ecom'e'mixed with water and oil that are emerging from the surrounding strata, before said water and oil enter the barrel of the well pump or the tubing up through which said water and oil fiow to the surface of-the ground.
  • the emulsion is allowed to stand in a quiescent state, usually in a settling tank, at a temperature varying from atmospheric temperatur 'to about 200 it, so as to .permit'the wateror brine to separate from the oil, it being preferable to keep the temperature low enough so as to prevent the valuable'constituents-of the oil from volatilizing.
  • the "treated emulsion- may be acted upon biyone or the other of various kinds of apparatus now used 'in the operation of breaking petroleum emulsions, such 'as hoinogenizers, hay tanks, gun barrels, filters, centrifuges, or electrical dehydrator's.
  • the amount of treating agent onthe anhydrous basis that is required to break the emulsion may vary from approximately 1 part of treating agent to 500 parts of emulsion, up to a ratio of 1 part of treating agent to 20,000 parts of emulsion, depending upon the type or kind of emulsion being treated.
  • the minimum ratio above referred to is often necessary, but in treating fresh emulsions, i. e., emulsions that willyield readily to the action of chemical d'emulsifyin'g agents, the maximum ratioabove mentioned "will frequently produce-highly satisfactory results.
  • For the average petroleum emulsion of-the water 'in-oil type -a ratio of l part of treatihgagen't'to 10,000 partsof emulsion will usually be found toproduce com'm'ercially satisfactory results.
  • Patent 1 A process for breaking petroleum emulsions of the water-in-oil type, which consists in subjecting the emulsion to the action of a demulsiiying agent consisting essentially of the fatty acid esters of an oxyalkylated polyhydroxy compound derived by the reaction of an alkyl polyhydroxy compound initially having three or more free hydroxyl groups with a mixture of ethylene and propylene oxides in which the proportion of propylene oxide is in the range of from about 15% to about 60% by weight of the mixture, and wherein the proportions of the mixed oxides to the alkyl polyhydroxy compound are such as to produce said oxyalkylated polyhydroxy compound having an average molecular weight ranging from about 2500 to about 7500, and wherein the fatty acid employed in forming said esters is a long-chain detergent forming fatty acid having 8 to 18 carbon atoms in the chain.
  • a demulsiiying agent consisting essentially of the fatty acid esters of an oxyalkylated polyhydroxy compound
  • esters are formed by reacting at least one mol of the fatty acid to each mol of said oxyalkylated polyhydroxy compound.
  • alkyl polyhydroxy compound is a member of the class consisting of glycerol and polyglycerol.
  • a process for breaking petroleum emulsions of the water-in-oil type which consists in subjecting the emulsion to the action of a demulsifying agent consisting essentially of the oleic acid esters of oxyalkylated glycerol derived by reacting glycerol with a mixture of ethylene and propylene oxides in equal proportions by weight, and in an amount sufficient to produce an oxyalkylated glycerol having a molecular weight of about 5000.
  • a demulsifying agent consisting essentially of the oleic acid esters of oxyalkylated glycerol derived by reacting glycerol with a mixture of ethylene and propylene oxides in equal proportions by weight, and in an amount sufficient to produce an oxyalkylated glycerol having a molecular weight of about 5000.
  • oleic acid esters are formed by reacting at least one mol of oleic acid to each mol of said oxyalkylated glycerol.
  • oleic acid esters are formed by reacting two mole of oleic acid to each mol of said oxyalkylated glycerol.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented May 20, 1952 PROCESS FOR TREAT 11 2c PETROLEUM EMULSIO S Raymond W. Todd and Fritz E. Fuchs, Houston, Tex., assignors to Aquaness Corporation, Houston, Tex., a corporation of Texas No Drawing. Application March 19, 1951, Serial No. 216,474
11 Claims. (01. 252-342) This invention relates to the treatment of emulsions of mineral oil and water, particularly water-in-oil petroleum emulsions, for the purpose of separating the oil from the water.
An object of this invention is to provide an improved process for breaking or separating petroleum emulsions by subjecting such emulsions to the action of a novel demulsifying composition to be described in greater detail hereinafter.
Another object is the provision of a novel demulsifier composition which is highly effective for breaking or separating petroleum emulsions.
The new demulsifier in accordance with this invention comprises a class of esterification products obtained by the reaction of a fatty acid with a particular type of hydroxylated compound.
The hydroxylated compounds employed as the intermediates in forming the final esterification product are of a specific character obtained by the reaction of an alkyl polyhydroxy compound initially containing three or more free hydroxyl groups with an oxyalkylating material consisting essentially of mixtures of ethylene oxide and propylene oxide in particular proportions.
The aklyl polyhydroxy compounds which are particularly adapted for preparation of the intermediate materials employed in making the final demulsifier composition are best exemplified by the class consisting of glycerol, polyglycerol, pentaerythritol, sorbitol, mannitol and the like. Polyglycerol is a polymer of glycerol, having in its simplest form, four free hydroxyl groups and a single ether linkage connecting two glyceryl residues as may be illustrated by the following formula:
Home omoH liquids completely soluble in water in all pro portions.
The fatty acids employed in making the final ester product may be any of the well known long chain, soap-forming fatty acids having 8 to 18 carbon atoms in the chain, such as stearic, oleic, ricinoleic, soya bean fatty acids, tall oil, linseed oil fatty acids, cocoa-nut fatty acids, and the like. The molal proportion of fatty acid to the oxyalkylated intermediate compounds may be varied to form either partial esters or fully esterified compounds or mixtures thereof. The mono-, dior tri-ester compounds appear generally to be the more effective compounds. The final ester compounds are all clear, moderately viscous liquids which are completely soluble or miscible with water in all proportions.
The procedure for oxyalkylating the polyhydroxy compounds is generally in accordance with well known procedures except that in every case the ethylene and propylene oxides are intermixed and reacted in mixed condition with the polyhydroxy material.
The resulting oxyalkylated polyhydroxy intermediates are then reacted in appropriate proportions with the selected fatty acid to. produce the desired ester products. This esterifying reaction is conducted in accordance with well known procedures for efiecting esterification between a hydroxy compound and an acid.
Following are several examples of the method of manufacture of the oxyalkylated polyhydroxy intermediate compounds and the final ester compounds employed in the process in accordance with the present invention:
OXYALKYLATED POLYHYDROXY INTERMEDIATE Example 1 46 pounds /2 mol) of glycerol, to which may be added about 4 pounds of sodium methylate as a catalyst, are placed in a Water-jacketed pressure chamber and heated to about 250 F. The chamber is purged with natural gas or methane and an atmosphere of such gas at a pressure of about 50 pounds per square inch is maintained in the chamber. 1250 pounds of ethylene oxide and 1250 pounds of propylene oxide are then pumped into the chamber, the oxides being intermixed as they are fed into the chamber. The oxides react with the glycerol and the resulting reaction tends to raise the temperature and pressure sharply. External heating is cut off and by circulation of cooling water the temperature is maintained within a range of from about 270 to about 350 F. The pressure is held to a range of from about to pounds per 3 square inch. As the reaction proceeds and the oxides are used up, the pressure drops to about that of the blanketing gas, about 50 pounds per square inch, when the reaction is completed. About 3 to 4 hours is required to complete the reaction.
The proportions of materials used in-this' example will produce an oxyalkylated product having an average molecular weight of about 5000 and this product is a light colored, relatively lowviscosity liquid which is completely soluble-in cold water.
Example 2 About 187 pounds each of ethylene and'propylene oxides are used instead of 1250 pounds each as in Example 1, and will produce an oxyalkylated glycerol product having a molecular weight of about 7500.
Example 3 About 625 pounds each of ethylene and propylene oxides are used instead of the amounts'stated in the previous examples to produce an 'oxyalkylated product having a molecular weight of about 2500.
Example 4 83 pounds of polyglycerol are substitutedfor the 46 pounds of glycerol in each of Examples 1, 2 and 3, above.
FINAL ESTER PRODUCT Example 1 Example 2 7500 pounds and 2500 pounds, respectively,of the Oxyalkylated Polyhydroxy Intermediates, Example 1 and Example 2, are substituted forthe 5000 pounds of Oxyalkylated Polyhydroxy Intel?- mediate, Example 1 in Final 'Ester Product, Example 1 above, to produce the corresponding mono-esters.
Example 3 564 pounds 2 mols) of oleic acid issubstituted for the 282 pounds in Final Ester Products, Examples l and 2, above, to produce the corresponding di-esters.
Example '4 350 pounds of tall oil are used in place of the 282 pounds of oleic acid in each or the Final-Ester Products, Examples 1 and 2 above,to produce the corresponding tall oil esters.
Example 5 700 pounds of tall oil are substituted in each case for the 564 pounds of oleic acid in Example 3 above.
Example 6 Molecular equivalents of cocoanut fatty acids.
soya bean fatty acids, stearic acid, or ricinoleic acid may be substituted for theoleic acid'an'dtall oil in each of the Final Ester ProductsfExa'mples 1, 2, 3, 4 and 5 above.
From the foregoing it will be understood that the demulsifier compositions employed in accordance with the present invention are fatty acid esters of a specific class of oxyalkylated polyhydroxy compounds, namely, aliphatic polyhydroxy compounds initially'having three0r more free hydroxyl groups whichhave been oxyalkylated with mixtures of ethylene and propylene oxides in the relative proportions stated above to produce compounds within the particular --ran'g'es of molecular weight above specified.
This specific group of compounds have been found to be exceptionally effective for breaking w-ater-in-oil petroleum emulsions.
may be brought in contactwith the emulsion to be treated in any of the numerous ways now-employed in the treatment of petroleum emulsions with chemical demulsifying agents, such, for example, as by introducing the treating agent into the well in which the emulsion-is produced, introducing the treating I agent into a conduit through which the emulsion is flowing, introducing the treating agent into a tank in which the emulsion is stored, *or introducing thetreat- 'ing agent into a container that holds a. sludge 'obtained from the bottom 'of an oil storage tank. -In some instances, it'may be advisable to introduce the treating agent into a producing-well in such a way that it will b'ecom'e'mixed with water and oil that are emerging from the surrounding strata, before said water and oil enter the barrel of the well pump or the tubing up through which said water and oil fiow to the surface of-the ground. 'After treatment the emulsion is allowed to stand in a quiescent state, usually in a settling tank, at a temperature varying from atmospheric temperatur 'to about 200 it, so as to .permit'the wateror brine to separate from the oil, it being preferable to keep the temperature low enough so as to prevent the valuable'constituents-of the oil from volatilizing. If desired, the "treated emulsion-may be acted upon biyone or the other of various kinds of apparatus now used 'in the operation of breaking petroleum emulsions, such 'as hoinogenizers, hay tanks, gun barrels, filters, centrifuges, or electrical dehydrator's.
The amount of treating agent onthe anhydrous basis that is required to break the emulsion may vary from approximately 1 part of treating agent to 500 parts of emulsion, up to a ratio of 1 part of treating agent to 20,000 parts of emulsion, depending upon the type or kind of emulsion being treated. In treating exceptionally refractory emulsions of the kind commonly'referred to as tank bottoms or residual pit oils," the minimum ratio above referred to is often necessary, but in treating fresh emulsions, i. e., emulsions that willyield readily to the action of chemical d'emulsifyin'g agents, the maximum ratioabove mentioned "will frequently produce-highly satisfactory results. For the average petroleum emulsion of-the water 'in-oil type -a ratio of l part of treatihgagen't'to 10,000 partsof emulsion will usually be found toproduce com'm'ercially satisfactory results.
Patent 1. A process for breaking petroleum emulsions of the water-in-oil type, which consists in subjecting the emulsion to the action of a demulsiiying agent consisting essentially of the fatty acid esters of an oxyalkylated polyhydroxy compound derived by the reaction of an alkyl polyhydroxy compound initially having three or more free hydroxyl groups with a mixture of ethylene and propylene oxides in which the proportion of propylene oxide is in the range of from about 15% to about 60% by weight of the mixture, and wherein the proportions of the mixed oxides to the alkyl polyhydroxy compound are such as to produce said oxyalkylated polyhydroxy compound having an average molecular weight ranging from about 2500 to about 7500, and wherein the fatty acid employed in forming said esters is a long-chain detergent forming fatty acid having 8 to 18 carbon atoms in the chain.
2. A process according to claim 1, wherein said esters are formed by reacting at least one mol of the fatty acid to each mol of said oxyalkylated polyhydroxy compound.
3. A process according to claim 1 wherein said alkyl polyhydroxy compound is a member of the class consisting of glycerol and polyglycerol.
4. A process according to claim 1 wherein said fatty acid is oleic acid.
5. A process according to claim 1 wherein said fatty acid is tall oil. Y
6. A process according to claim 1 wherein said 9. A process for breaking petroleum emulsions of the water-in-oil type, which consists in subjecting the emulsion to the action of a demulsifying agent consisting essentially of the oleic acid esters of oxyalkylated glycerol derived by reacting glycerol with a mixture of ethylene and propylene oxides in equal proportions by weight, and in an amount sufficient to produce an oxyalkylated glycerol having a molecular weight of about 5000.
10. A process according to claim 9 wherein the oleic acid esters are formed by reacting at least one mol of oleic acid to each mol of said oxyalkylated glycerol.
11. A process according to claim 9 wherein the oleic acid esters are formed by reacting two mole of oleic acid to each mol of said oxyalkylated glycerol.
RAYMOND W. TODD. FRITZ E. FUCHS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,312,732 Salathiel Mar. 12, 1943 2,454,808 Kirkpatrick -1 Nov. 30, 1948 2,500,349 De Groote Mar. 14, 1950 2,540,437 Fuchs Feb. 6, 1951 2,549,434 De Groote Apr. 17, 1951

Claims (1)

1. A PROCESS FOR BREAKING PETROLEUM EMULSIONS OF THE WATER-IN-OIL TYPE, WHICH CONSISTS IN SUBJECTING THE EMULSION TO THE ACTION OF A DEMULSIFYING AGENT CONSISTING ESSENTIALLY OF THE FATTY ACID ESTERS OF AN OXYALKYLATED POLYHYDROXY COMPOUND DERIVED BY THE REACTION OF AN ALKYL POLYHYDROXY COMPOUND INITIALLY HAVING THREE OR MORE FREE HYDROXYL GROUPS WITH A MIXTURE OF ETHYLENE AND PROPYLENE OXIDES IN WHICH THE PROPORTION OF PROPYLENE OXIDE IS IN THE RANGE OF FROM ABOUT 15% TO ABOUT 60% BY WEIGHT OF THE MIXTURE, AND WHEREIN THE PROPORTIONS OF THE MIXED OXIDES TO THE ALKYL POLYHYDROXY COMPOUND ARE SUCH AS TO PRODUCE SAID OXYALKYLATED POLYHYDROXY COMPOUND HAVING AN AVERAGE MOLECULAR WEIGHT RANGING FROM ABOUT 2500 TO ABOUT 7500, AND WHEREIN THE FATTY ACID EMPLOYED IN FORMING SAID ESTERS IS A LONG-CHAIN DETERGENT FORMING FATTY ACID HAVING 8 TO 18 CARBON ATOMS IN THE CHAIN.
US216474A 1951-03-19 1951-03-19 Process for treating petroleum emulsions Expired - Lifetime US2597204A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US216474A US2597204A (en) 1951-03-19 1951-03-19 Process for treating petroleum emulsions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US216474A US2597204A (en) 1951-03-19 1951-03-19 Process for treating petroleum emulsions

Publications (1)

Publication Number Publication Date
US2597204A true US2597204A (en) 1952-05-20

Family

ID=22807216

Family Applications (1)

Application Number Title Priority Date Filing Date
US216474A Expired - Lifetime US2597204A (en) 1951-03-19 1951-03-19 Process for treating petroleum emulsions

Country Status (1)

Country Link
US (1) US2597204A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2695886A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2695882A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2695885A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2819221A (en) * 1954-08-06 1958-01-07 Petrolite Corp Process for breaking petroleum emulsions employing certain carboxybutane esters
US2911434A (en) * 1956-04-24 1959-11-03 Visco Products Co Surface active dicarboxylic acid esters of polyalkylene oxides
US2987490A (en) * 1956-09-17 1961-06-06 Visco Products Co Surface-active esters of polymerized polyethenoid fatty acids
US3062671A (en) * 1962-11-06 Hard ester waxes and process for
US3124602A (en) * 1964-03-10 Aliphatic esters of unsaturated
US3451936A (en) * 1965-04-24 1969-06-24 Ledoga Spa Surfactant compositions from active hydrogen organic compounds,fatty acid esters and alkylene oxides,and related manufacturing process
US3637523A (en) * 1968-09-12 1972-01-25 Scm Corp Esters of glycerol and polyhydric alcohol copolymers useful as emulsifying agents and process for their production

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2312732A (en) * 1938-10-19 1943-03-02 Standard Oil Dev Co Process and agent for breaking petroleum emulsions
US2454808A (en) * 1946-02-23 1948-11-30 Visco Products Co Reagent and process for resolving emulsions
US2500349A (en) * 1948-04-17 1950-03-14 Petrolite Corp Process for breaking petroleum emulsions
US2540437A (en) * 1948-04-27 1951-02-06 Aquanox Corp Treatment of emulsions
US2549434A (en) * 1949-08-11 1951-04-17 Petrolite Corp Processes for breaking petroleum emulsions

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2312732A (en) * 1938-10-19 1943-03-02 Standard Oil Dev Co Process and agent for breaking petroleum emulsions
US2454808A (en) * 1946-02-23 1948-11-30 Visco Products Co Reagent and process for resolving emulsions
US2500349A (en) * 1948-04-17 1950-03-14 Petrolite Corp Process for breaking petroleum emulsions
US2540437A (en) * 1948-04-27 1951-02-06 Aquanox Corp Treatment of emulsions
US2549434A (en) * 1949-08-11 1951-04-17 Petrolite Corp Processes for breaking petroleum emulsions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3062671A (en) * 1962-11-06 Hard ester waxes and process for
US3124602A (en) * 1964-03-10 Aliphatic esters of unsaturated
US2695886A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2695882A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2695885A (en) * 1952-01-21 1954-11-30 Petrolite Corp Process for breaking petroleum emulsions
US2819221A (en) * 1954-08-06 1958-01-07 Petrolite Corp Process for breaking petroleum emulsions employing certain carboxybutane esters
US2911434A (en) * 1956-04-24 1959-11-03 Visco Products Co Surface active dicarboxylic acid esters of polyalkylene oxides
US2987490A (en) * 1956-09-17 1961-06-06 Visco Products Co Surface-active esters of polymerized polyethenoid fatty acids
US3451936A (en) * 1965-04-24 1969-06-24 Ledoga Spa Surfactant compositions from active hydrogen organic compounds,fatty acid esters and alkylene oxides,and related manufacturing process
US3637523A (en) * 1968-09-12 1972-01-25 Scm Corp Esters of glycerol and polyhydric alcohol copolymers useful as emulsifying agents and process for their production

Similar Documents

Publication Publication Date Title
US2626907A (en) Process for breaking petroleum emulsions
US2597204A (en) Process for treating petroleum emulsions
US2950313A (en) Surface active polyoxypropylene esters
US2950299A (en) Surface active substances of ether ester class
US2507560A (en) Process for breaking petroleum emulsions
US2454808A (en) Reagent and process for resolving emulsions
US2312731A (en) Process and agent for breaking petroleum emulsions
US2911434A (en) Surface active dicarboxylic acid esters of polyalkylene oxides
US2312732A (en) Process and agent for breaking petroleum emulsions
US1977089A (en) Process for breaking petroleum emulsions
US2401966A (en) Process and agent for breaking petroleum emulsions
US1977146A (en) Process for breaking petroleum emulsions
US2423364A (en) Process for breaking petroleum emulsions
US2324491A (en) Process for breaking petroleum emulsions
US2369818A (en) Water-soluble high molal oxyalkylated esters, and method of making same
US2000717A (en) Process for breaking petroleum emulsions
US2599538A (en) Process of demulsifying
US2422177A (en) Process for breaking petroleum emulsions
US2602064A (en) Process for breaking petroleum emulsions
RU2722481C1 (en) Method of producing emulsifier for drilling muds on hydrocarbon base
US2050923A (en) Process for breaking petroleum emulsions
US2492473A (en) Demulsifier composition
US2943061A (en) Demulsifying compositions and process
US2324488A (en) Process for breaking petroleum emulsions
US1976602A (en) Process for breaking petroleum emulsions