WO2009018291A1 - Processing mixtures of hydrocarbons and water - Google Patents
Processing mixtures of hydrocarbons and water Download PDFInfo
- Publication number
- WO2009018291A1 WO2009018291A1 PCT/US2008/071509 US2008071509W WO2009018291A1 WO 2009018291 A1 WO2009018291 A1 WO 2009018291A1 US 2008071509 W US2008071509 W US 2008071509W WO 2009018291 A1 WO2009018291 A1 WO 2009018291A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- sludge
- mixture
- water
- hydrocarbons
- carbon atoms
- Prior art date
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Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B08—CLEANING
- B08B—CLEANING IN GENERAL; PREVENTION OF FOULING IN GENERAL
- B08B9/00—Cleaning hollow articles by methods or apparatus specially adapted thereto
- B08B9/08—Cleaning containers, e.g. tanks
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/004—Surface-active compounds containing F
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/06—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using emulsions
Definitions
- Crude oil sludge contamination of oil tankers is one such occurrence. Such contamination is a problem, particularly where such oil tankers need to undergo repairs and other servicing activity usually involving high temperatures at ship yards.
- the presence of residual crude oil sludge can cause a number of problems during such cleaning (e.g., the presence of the cargo vapour, high disposal cost of the sludge and the difficulty in ensuring that the cleansing operation is fully effective).
- tar sands processing plants spots of tar sand contaminate the equipment. Tar sands are mixtures of hydrocarbons, water, and typically sand or clay. Cleaning of such spots has proven to be difficult.
- above-ground equipment e.g., vehicles and heavy equipment
- Use of strong acids such as hydrochloric and hydrofluoric acid is commonly necessary, which can cause corrosion of the equipment.
- this disclosure provides a method of facilitating separation of hydrocarbon from a mixture comprising hydrocarbons and water, the method comprising: exposing the mixture to a composition comprising a first polymeric surfactant such that at least a portion of the hydrocarbons forms a separate layer from the remaining portion of the mixture, the first polymeric surfactant comprising at least one first divalent unit selected from the group consisting of formulae: and
- R and R 2 are each independently hydrogen or alkyl of 1 to 4 carbon atoms; n is an integer from 2 to 10; and m is an integer from 1 to 5.
- this disclosure provides a use of a composition comprising a first polymeric surfactant as defined above to at least partially separate a mixture comprising hydrocarbons and water such that at least a portion of the hydrocarbons forms a separate layer from the remaining portion of the mixture.
- At least 10%, 20%, 30%, 40%, 50%, 60%, 70%, or even at least 80% by volume of the hydrocarbons forms a separate layer from the remaining portion of the mixture.
- the method and/or use further comprises removing at least a portion of the hydrocarbon from the separate hydrocarbon layer.
- the mixture comprising hydrocarbons and water is a sludge comprising petroleum and water (e.g., a crude oil sludge).
- the mixture is tar sand.
- the mixture is an emulsion comprising at least the hydrocarbons and the water.
- this disclosure provides a method of removing a sludge comprising a mixture of petroleum and water from a surface, the method comprising treating the sludge with an amount of a composition comprising a first polymeric surfactant as defined above effective to remove the sludge from the surface.
- this disclosure provides a use of a composition comprising a first polymeric surfactant as defined above to remove a sludge comprising a mixture of petroleum and water from a surface.
- the sludge is a contaminant in at least one of a crude oil storage container (e.g., an oil tanker) or a crude oil transport container.
- a crude oil storage container e.g., an oil tanker
- a crude oil transport container e.g., a crude oil transport container
- the first polymeric surfactant comprises at least one second divalent unit selected from the group consisting of formulae:
- Ri and R 2 are each independently hydrogen or alkyl of 1 to 4 carbon atoms;
- the composition comprises a mixture of at least two (e.g., two, three, four, five, or more) different polymeric surfactants, wherein each such surfactant comprises a first divalent unit selected from the group consisting of formulae (I) and (II) and a second divalent unit selected from the group consisting of formulae (III), (IV), and (V),
- Methods and/or uses of the present disclosure typically allow easy cleaning of surfaces (e.g., on tankers and other equipment) contaminated with mixtures comprising hydrocarbons and water (e.g., sludge).
- methods of the present disclosure allow recovery of at least some of the hydrocarbons (e.g., crude oil) present in these mixtures, which may provide economic and/or environmental advantages.
- hydrocarbons e.g., crude oil
- Alkyl group and the prefix “alk-” are inclusive of both straight chain and branched chain groups and of cyclic groups. Cyclic groups can be monocyclic or polycyclic and, in some embodiments, have from 3 to 10 ring carbon atoms.
- fluoroalkyl group includes linear, branched, and/or cyclic alkyl groups in which all C-H bonds are replaced by C-F bonds as well as groups in which hydrogen or chlorine atoms are present instead of fluorine atoms provided that up to one atom of either hydrogen or chlorine is present for every two carbon atoms.
- fluoroalkyl groups when at least one hydrogen or chlorine is present, the fluoroalkyl group includes at least one trifluoromethyl group.
- hydrocarbon refers to compounds consisting of carbon and hydrogen and includes linear, branched, and cyclic groups which may be saturated or unsaturated.
- sludge refers to a viscous mixture comprising petroleum and water.
- a sludge may contain other components (e.g., mud, clay, sand, and other solids).
- sludge as used herein includes tar sand.
- Crude oil includes light, intermediate, and heavy crude oil.
- mixtures of hydrocarbons and water that are separated by the methods disclosed herein do not include materials where the hydrocarbons and water already exist in layers.
- a sludge comprising petroleum and water (e.g., a crude oil sludge).
- the sludge may be present, for example, as a contaminant in a crude oil transport container (such as an oil tanker) or in a crude oil storage container.
- a crude oil transport container such as an oil tanker
- the sludge typically needs to be removed before the servicing work can be undertaken (e.g., at a ship yard).
- the sludge present in such containers is typically dense, viscous, and like cake dough in texture and usually contains paraffmic waxes, asphaltenes, salt water, mud and other residual solids, scale and organic acids.
- methods and/or uses of this disclosure can be used to process a crude oil contaminant spot (e.g., a spot of crude oil sludge) on above-ground equipment (e.g., vehicles, drilling equipment, oil rig components, pipelines, railroad tanker cars, storage silos, and other heavy equipment) in an oil field.
- a crude oil contaminant spot e.g., a spot of crude oil sludge
- above-ground equipment e.g., vehicles, drilling equipment, oil rig components, pipelines, railroad tanker cars, storage silos, and other heavy equipment
- Such crude oil contaminant spots may result from normal use of the equipment or may result from an unexpected discharge (e.g., from a well or holding container).
- methods and/or uses according to the present disclosure can be used to process tar sand (i.e., oil sand). Spot contamination of tar sand may collect, for example, on above-ground equipment used in tar sands mines and processing plants.
- tar sand i.e., oil sand
- compositions comprising a first polymeric surfactant
- containers e.g., oil tankers and storage containers
- spot contamination e.g., crude oil or tar sand
- the composition can be applied by wetting a cleaning cloth with the composition and manually rubbing the sludge or spot contamination.
- a suitable implement such as a scraper
- the composition can be applied to the container or equipment bearing the sludge or spot by spraying (e.g., with a high-pressure hose).
- methods and/or uses of the present disclosure are useful in enabling the recovery of at least some of the hydrocarbon (e.g., crude oil) present in mixtures of hydrocarbon and water (e.g., sludge and tar sand) to reduce the impact on the environment.
- Cleaning waste that is recovered, for example, after carrying out separation or surface treatment methods disclosed herein typically will segregate into layers in which at least a portion of the hydrocarbons forms a separate layer from the remaining portion of the mixture.
- the recovered sludge can be exposed to a composition comprising a first polymeric surfactant according to methods disclosed herein.
- the recovered sludge can be converted into three readily separable layers, namely a first hydrocarbon containing upper layer; a second, middle phase of clear liquid, hydrocarbon- containing solids, and surfactant; and a third, lower phase which contains clear liquid, hydrocarbon-containing solids, and surfactant.
- hydrocarbon-containing solids are primarily located in the middle layer.
- at least a portion of the hydrocarbon can be removed from the other layers using known techniques (e.g., decanting and draining).
- the hydrocarbon-containing solids can be separated by known techniques (e.g., decanting and filtering).
- methods and/or uses of the present disclosure can be used when the mixture of hydrocarbons and water is an emulsion comprising at least the hydrocarbons and the water (e.g., an emulsion of at least the hydrocarbons in the water, an emulsion of least the water in the hydrocarbons, and a bicontinuous emulsion).
- the emulsion may be a naturally occurring form of crude oil as it is extracted from a well.
- the emulsion may be crude oil waste resulting, for example, from cleaning or other processing.
- at least of portion of the hydrocarbons form a separate layer from the remaining portion of the mixture (i.e., the emulsion is cracked).
- methods disclosed herein can be used to recover useable crude oil effectively (e.g., in a recycling operation of crude oil waste) by separating at least of portion of the hydrocarbon from the hydrocarbon layer.
- Methods and/or uses according to the present disclosure can typically be carried out at a temperature up to 60 °C (in some embodiments, up to 55, 50, 45, 40, 35, 30, or even up to 25 °C).
- methods and/or uses according to the present disclosure typically can be carried out at ambient temperature (e.g., external heating is typically not needed to facilitate separation of hydrocarbon from a mixture of hydrocarbons and water).
- compositions useful in practicing the methods and/or uses disclosed herein comprise a first polymeric surfactant, which comprises a compound having at least one first divalent unit selected from the group consisting of formulae (I) and (II); and at least one second divalent unit selected from the group consisting of formulae (III), (IV), and (V).
- first divalent unit is represented by formula (I).
- the first divalent unit is represented by formula (II).
- the group Rf is selected from the group consisting of perfluoromethyl, perfhioroethyl, perfluoropropyl, perfluorobutyl, (such as perfluoro-n-butyl or perfluoro-sec-butyl) perfluoropentyl, and perfluorohexyl.
- R f represents a fluoroalkyl group having from 2 to 5 (in some embodiments, 3 to 5) carbon atoms.
- R f is perfluorobutyl (such as perfluoro-n-butyl or perfluoro-sec-butyl).
- Each of the groups R, Ri and R 2 are independently hydrogen or alkyl of 1 to 4 carbon atoms, for example, methyl, ethyl, n-propyl, isopropyl, butyl, isobutyl, or t-butyl.
- R is methyl or ethyl.
- R 2 is hydrogen or methyl.
- n is 2 to 8 (in some embodiments, 2 to 6 or even 2 to 4). In formula (I), n may be 2, 3, 4, 5, 6, 7, 8, 9, or 10.
- m is 1 to 2.
- m may be 1 , 2, 3, 4, or 5.
- Each q can independently be an integer from 0 to about 55, generally in a range of 1 to 55.
- the ratio p/q is within a range from 0.15 to 5, in other embodiments, in a range from 0.3 to 5, 0.15 to 4, 0.15 to 3, 0.15 to 2.7, or even from 0.15 to 2.5. In some other embodiments the ratio p/q is within a range from 0.75 to 4, 0.75 to 3, 0.75 to 2.7, or even from 0.75 to 2.5. In some further embodiments the ratio p/q is within a range from 1 to 4, 1 to 3, 1 to 2.7, or even from 1 to 2.5. In some other embodiments the ratio p/q is within a range from 1.5 to 4, 1.5 to 3, 1.5 to 2.7 or even from 1.5 to 2.5.
- the second divalent unit is represented by formula III, wherein p is an integer from 5 to 15 (in some embodiments, from 9 to 13 or even 11), and wherein q is an integer from 15 to 25 (in some embodiments, 19 to 23 or even 21).
- the polymeric surfactant useful in practicing the present disclosure is a reaction product formed by copolymerisation of: a first reactant which is at least one compound selected from the group consisting of:
- a second reactant which is at least one compound selected from the group consisting of compounds represented by formulae:
- the polymeric surfactants described above can be prepared, for example, by techniques known in the art (e.g., by free radical initiated copolymerization of a fluoroalkyl group-containing acrylate with a poly(alkyleneoxy) acrylate (e.g., monoacrylate or diacrylate or mixtures thereof). Adjusting the concentration and activity of the initiator, the concentration of monomers, the temperature, and the chain-transfer agents can control the molecular weight of the polyacrylate copolymer. The description of the preparation of such polyacrylates is described, for example, in U.S. Pat. No. 3,787,351 (Olson), the disclosure of which is incorporated herein by reference.
- nonafluorobutanesulfonamido acrylate monomers are described, for example, in U.S. Pat. No. 2,803,615 (Ahlbrecht et al.), the disclosure of which is incorporated herein by reference.
- the methods described for making nonafluorobutylsulfonamido group- containing structures can be also used to make heptafluoropropylsulfonamido groups by starting with heptafluoropropylsulfonyl fluoride, which can be made, for example, by the methods described in Examples 2 and 3 of U.S. Pat. No. 2,732,398 (Brice et al.), the disclosure of which is incorporated herein by reference.
- Examples of fluoroaliphatic polymeric esters and their preparation are described, for example, in U.S. Pat. No. 6,664,354 (Savu et al.), the disclosure of which is incorporated herein by reference.
- MeFBSEA N-methylperfluorobutanesulfonamidoethyl acrylate
- the weight ratio of the first and second reactants can be varied, for example, from 10:90 (in some embodiments from 15:85, 20:80, 25:75, 30:70, or even from 35:65) up to 50:50 (in some embodiments, 60:40, 65:35, 70:30, or even up to 75:25).
- the weight ratio of the first reactant (in some embodiments, Formula (VI) to the second reactant (in some embodiments, Formula (VIII) is in a range from about 20:80 to about 50:50.
- the ratio of MeFBSEA to the second reactant can be about 20:80, 23:77, 25:75, 28:72, 30:70, 33:67, 35:65, 38:62, 40:60, 43:57, 45:55, 48:52, or even about 50:50.
- polymeric surfactants useful in practicing the present disclosure include at least one anionic group.
- anionic groups include sulfonates (e.g., - SO 3 M), sulfates (e.g., -OSO 3 M), and carboxylates (e.g., -C(O)OM), wherein M is hydrogen, a metal cation such as an alkali or alkaline earth metal cation (e.g., sodium, potassium, calcium or magnesium, and the like), or a nitrogen-based cation, such as ammonium or a protonated tertiary amine (e.g., (HOCH 2 CH 2 ) 2 N ⁇ HCH 3 ).
- anionic groups can be incorporated into polymeric surfactants useful in practicing the methods disclosed herein, for example, by using appropriate monomers in the polymerization reaction.
- Useful monomers that contain anionic groups include acrylic acid, methacrylic acid, 2-carboxyethyl acrylate, 2-carboxyethyl methacryate, and 2-acrylamido-2 -methyl- 1- propane sulfonic acid (AMPS).
- AMPS 2-acrylamido-2 -methyl- 1- propane sulfonic acid
- Useful amounts of these monomers in the preparation of anionic polymeric surfactants are described, for example, in U.S. Pat. No. 6,664,354 (Savu et al.).
- Polymeric surfactants useful in practicing the present disclosure typically have a number average molecular weight in a range of from 1000 to 100,000 (in some embodiments from 1000 to 50,000, 1000 to 40,000, 1000 to 30,000, 1000 to 20,000, or even 1000 to 10,000) grams/mole although higher and lower molecular weights may also be useful.
- polymeric surfactants useful in practicing the present disclosure have a number average molecular weight of less than 100,000 grams/mole (in some embodiments, up to 100,000 grams/mole).
- the polymeric surfactants have number average molecular weights of at least 1000 grams/mole.
- the polymeric surfactants typically have a distribution of molecular weights and compositions. Number average molecular weights can be measured, for example, by gel permeation chromatography (i.e., size exclusion chromatography) using techniques known in the art.
- polymeric surfactants useful in practicing the present disclosure can, in some embodiments, be free of hydro lyzable silane groups. This may be advantageous, for example, by prolonging the storage-life of the composition.
- compositions useful in practicing the present disclosure include the polymeric surfactant(s) in an amount sufficient to cause at least a portion of the hydrocarbon to form a separate layer from the remaining portion of the mixture. In some embodiments, compositions useful in practicing the methods disclosed herein include the polymeric surfactant(s) in an amount effective to remove at least a portion of the sludge from the surface.
- the amount of polymeric surfactant in the composition will be at least 0.1% (in some embodiments, at least 0.2%, 0.3%, 0.4%, 0.5%, 0.6%, 0.7%, 0.8%, 0.9%, 1%, 1.5%, 2%, 2.5%, 3%, 3.5%, 4%, 4.5%, or even at least 5%) by weight, based on the total weight of the composition.
- the polymeric surfactant(s) may be present in a range from 0.1% to 10% (in some embodiments, 0.5% to 10%, 1% to 10%, 1% to 6%, or even 0.1% to 6%) by weight, based on the total weight of the composition.
- the composition comprises at least one of water or an organic solvent (e.g., hydrocarbon liquid).
- an organic solvent e.g., hydrocarbon liquid.
- the amount of water is greater than that of the organic solvent.
- the organic solvent is a hydrocarbon liquid such as C 6 to C 10 alkane, in some embodiments, at least one of hexane or a C 9 or C 1O alkane.
- the organic solvent is an ether having up to 10 carbon atoms. Suitable ethers include glycol ethers available from Dow Chemical Co., Midland, Michigan under the trade designation "DOWANOL".
- the organic solvent is 2- methoxymethylethoxypropanol.
- the composition comprises both a hydrocarbon liquid and an ether having up to 10 carbon atoms.
- the amount of water is less than about 96% by weight and the amount of organic solvent is at least about 4% by weight, based on the total weight of the composition.
- the ratio of water to hydrocarbon liquid can be varied to achieve the most effective result.
- compositions useful in practicing the present disclosure comprise l-methyl-2- pyrrolidinone.
- the other materials may have some useful function as well.
- a second, different surfactant can be added.
- Useful second surfactants include silicone-based surfactants, polymeric surfactants, and surfactants available, for example, from Air Products and Chemicals, Inc., Allentown, PA, under the trade designation "SURFYNOL".
- SURFYNOL Air Products and Chemicals, Inc., Allentown, PA
- methods and uses disclosed herein can be carried out without using a second, different surfactant (e.g., a non-fluorinated surfactant).
- compositions useful in practicing the present disclosure can be prepared using conventional techniques such as stirring (e.g., by mechanical or magnetic methods), shaking, or homogenizing, for example, a mixture of polymeric surfactant(s), at least one of water or organic solvent, and optionally other materials (e.g., inert materials and a second, different surfactants).
- the components of the compositions can be combined in any order.
- the composition comprises a hydrocarbon liquid and water
- the hydrocarbon liquid is added to a mixture of polymeric surfactant(s) and water.
- the polymeric surfactant(s) is added to a mixture of hydrocarbon liquid and water.
- a polymeric surfactant was prepared as described in Example 4 of U. S. Pat. No. 6,664,354 (Savu et al.), the disclosure of which example is incorporated herein by reference, except using JV-methylperfluorobutanesulfonamidoethyl acrylate (MeFBSEA) and the acrylate prepared from a block copolymer of ethylene oxide and propylene oxide obtained from BASF Corporation, Ludwigshafen, Germany, under the trade designation "PLURONIC” in a weight ratio of 38:62 and using 15.6 grams (g) of 50/50 mineral spirits/organic peroxide initiator (tert-butyl peroxy-2-ethylhexanoate obtained from Akzo Nobel, Arnhem, The Netherlands under the trade designation "TRIGONOX-21-C50”) in place of 2,2'-azobisisobutyronitrile, and with 9.9 g of l-methyl-2-pyrrolidinone added to the charges.
- MeFBSEA JV-
- Sample 1 was prepared by dissolving a portion of the upper layer, contained in Jar 1, in acetone.
- Sample 3 was prepared using the method described for Sample 2 except the extraction procedure used heptanes instead of dichloromethane.
- Sample 4 was prepared using the method described for Sample 2 except the extraction procedure used 1 mL of the clear liquid from Jar 3 instead of from Jar 2.
- Sample 5 was prepared using the method described for Sample 2 except the extraction procedure used 1 mL of the clear liquid from Jar 3 instead of from Jar 2, and the extraction procedure used heptanes instead of dichloromethane.
- Sample 6 was prepared by dissolving a portion of the black solid from Jar 2 in acetone.
- Sample 7 was prepared by dissolving a portion of the black solid from Jar 3 in acetone.
- GC/MS gas chromatography/mass spectroscopy
- the final temperature was held for 17 minutes.
- Helium at a flow velocity of approximately 40 cm/second, was used as the carrier gas, and the injector was maintained at a temperature of 250 0 C.
- the MSD was operated in the electron impact ionization mode using 70 eV electrons for ionization. Data were collected by scanning the MSD over the mass range of 29-550 Daltons at a scan rate of approximately one scan per second.
- the polymeric surfactant prepared as described in Example 1 was diluted with 2- methoxymethylethoxypropanol to prepare a 25% by weight of the polymeric surfactant.
- the polymeric surfactant solution (2.4 mL) was mixed with 192 mL of de-ionized water and 8 mL of decane to provide a 0.3% by weight solution of surfactant.
- a sample of crude oil sludge was applied on a square, aluminum coupon (2 inches (5.1 cm) by 2 inches (5.1 cm)) in a thin layer.
- a 200-microliter portion of the prepared surfactant solution was used to clean the coupon using the following procedure. The time was noted, and two drops of the surfactant solution were placed onto the sludge-treated coupon and wiped off with a clean paper towel. This step was repeated three more times, at which point the full 200 microliters of surfactant solution were used.
- Example 3 was prepared according to the Surfactant Solution Preparation procedure described in Example 2, except 0.6 mL of a 100% active nonionic polymeric surfactant obtained from Mason Chemical, Arlington Heights, IL, under the trade designation "MASURF FS-2000" was used instead of the 25% by weight polymeric surfactant solution.
- a 100% active nonionic polymeric surfactant obtained from Mason Chemical, Arlington Heights, IL, under the trade designation "MASURF FS-2000" was used instead of the 25% by weight polymeric surfactant solution.
- a aluminium coupon was treated with a sample of crude oil sludge using the procedure of Example 2.
- the coupon of Example 3 was cleaned using the method of Example 2 except that 200 microliters of the Illustrative Example surfactant solution were used for the test instead of 200 microliters of the 25% by weight polymeric surfactant solution.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12/671,601 US20110284427A1 (en) | 2007-08-01 | 2008-07-30 | Processing mixtures of hydrocarbons and water |
CN200880102727A CN101835519A (en) | 2007-08-01 | 2008-07-30 | The processing of the mixture of hydrocarbon and water |
EP08796801A EP2180929A1 (en) | 2007-08-01 | 2008-07-30 | Processing mixtures of hydrocarbons and water |
CA2695180A CA2695180A1 (en) | 2007-08-01 | 2008-07-30 | Processing mixtures of hydrocarbons and water |
JP2010520139A JP2010535101A (en) | 2007-08-01 | 2008-07-30 | Treatment of hydrocarbon and water mixtures |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
MYPI20071269 | 2007-08-01 | ||
MYPI20071269 | 2007-08-01 |
Publications (1)
Publication Number | Publication Date |
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WO2009018291A1 true WO2009018291A1 (en) | 2009-02-05 |
Family
ID=39863069
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/US2008/071509 WO2009018291A1 (en) | 2007-08-01 | 2008-07-30 | Processing mixtures of hydrocarbons and water |
Country Status (7)
Country | Link |
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US (1) | US20110284427A1 (en) |
EP (1) | EP2180929A1 (en) |
JP (1) | JP2010535101A (en) |
KR (1) | KR20100043262A (en) |
CN (1) | CN101835519A (en) |
CA (1) | CA2695180A1 (en) |
WO (1) | WO2009018291A1 (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3787351A (en) * | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
JPS53111569A (en) * | 1977-03-10 | 1978-09-29 | Dainippon Ink & Chemicals | Method of separating oil and water |
JPS5465180A (en) * | 1977-11-01 | 1979-05-25 | Daikin Ind Ltd | Separating method for oil from oil-in-water type emulsion |
US5350795A (en) * | 1991-07-10 | 1994-09-27 | Minnesota Mining And Manufacturing Company | Aqueous oil and water repellent compositions which cure at ambient temperature |
US20030139550A1 (en) * | 1999-10-27 | 2003-07-24 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
-
2008
- 2008-07-30 US US12/671,601 patent/US20110284427A1/en not_active Abandoned
- 2008-07-30 CA CA2695180A patent/CA2695180A1/en not_active Abandoned
- 2008-07-30 CN CN200880102727A patent/CN101835519A/en active Pending
- 2008-07-30 EP EP08796801A patent/EP2180929A1/en not_active Withdrawn
- 2008-07-30 WO PCT/US2008/071509 patent/WO2009018291A1/en active Application Filing
- 2008-07-30 JP JP2010520139A patent/JP2010535101A/en active Pending
- 2008-07-30 KR KR1020107004155A patent/KR20100043262A/en not_active Application Discontinuation
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3787351A (en) * | 1972-02-28 | 1974-01-22 | Minnesota Mining & Mfg | Use of soluble fluoroaliphatic oligomers in resin composite articles |
JPS53111569A (en) * | 1977-03-10 | 1978-09-29 | Dainippon Ink & Chemicals | Method of separating oil and water |
JPS5465180A (en) * | 1977-11-01 | 1979-05-25 | Daikin Ind Ltd | Separating method for oil from oil-in-water type emulsion |
US5350795A (en) * | 1991-07-10 | 1994-09-27 | Minnesota Mining And Manufacturing Company | Aqueous oil and water repellent compositions which cure at ambient temperature |
US20030139550A1 (en) * | 1999-10-27 | 2003-07-24 | 3M Innovative Properties Company | Fluorochemical sulfonamide surfactants |
Non-Patent Citations (1)
Title |
---|
DATABASE WPI Week 197845, Derwent World Patents Index; AN 1978-80638A, XP002501782 * |
Also Published As
Publication number | Publication date |
---|---|
CA2695180A1 (en) | 2009-02-05 |
JP2010535101A (en) | 2010-11-18 |
KR20100043262A (en) | 2010-04-28 |
CN101835519A (en) | 2010-09-15 |
EP2180929A1 (en) | 2010-05-05 |
US20110284427A1 (en) | 2011-11-24 |
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