CN117070245B - Reverse demulsifier and preparation method thereof - Google Patents
Reverse demulsifier and preparation method thereof Download PDFInfo
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- CN117070245B CN117070245B CN202311332602.2A CN202311332602A CN117070245B CN 117070245 B CN117070245 B CN 117070245B CN 202311332602 A CN202311332602 A CN 202311332602A CN 117070245 B CN117070245 B CN 117070245B
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- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 64
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical class O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 claims abstract description 42
- 229920000058 polyacrylate Polymers 0.000 claims abstract description 31
- 229920005610 lignin Polymers 0.000 claims abstract description 30
- 239000004094 surface-active agent Substances 0.000 claims abstract description 30
- 150000001412 amines Chemical class 0.000 claims abstract description 19
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 19
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims abstract description 18
- 229940051841 polyoxyethylene ether Drugs 0.000 claims abstract description 18
- 229920000056 polyoxyethylene ether Polymers 0.000 claims abstract description 18
- 239000002994 raw material Substances 0.000 claims abstract description 17
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 claims abstract description 13
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 claims abstract description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 9
- 238000003756 stirring Methods 0.000 claims description 75
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 40
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 40
- 238000002156 mixing Methods 0.000 claims description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 32
- 238000006243 chemical reaction Methods 0.000 claims description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- ONCZQWJXONKSMM-UHFFFAOYSA-N dialuminum;disodium;oxygen(2-);silicon(4+);hydrate Chemical compound O.[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Na+].[Na+].[Al+3].[Al+3].[Si+4].[Si+4].[Si+4].[Si+4] ONCZQWJXONKSMM-UHFFFAOYSA-N 0.000 claims description 20
- 229940080314 sodium bentonite Drugs 0.000 claims description 20
- 229910000280 sodium bentonite Inorganic materials 0.000 claims description 20
- 239000000243 solution Substances 0.000 claims description 20
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 claims description 18
- JRWNODXPDGNUPO-UHFFFAOYSA-N oxolane;prop-2-enoic acid Chemical compound C1CCOC1.OC(=O)C=C JRWNODXPDGNUPO-UHFFFAOYSA-N 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- 238000010438 heat treatment Methods 0.000 claims description 15
- 238000005406 washing Methods 0.000 claims description 15
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 claims description 10
- -1 dodecyl dimethyl tertiary amine Chemical class 0.000 claims description 10
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 claims description 10
- 239000000047 product Substances 0.000 claims description 10
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 claims description 10
- 230000020477 pH reduction Effects 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- VBHDMJVUPJVYJZ-UHFFFAOYSA-N 2-nonylphenol;prop-2-enoic acid Chemical compound OC(=O)C=C.CCCCCCCCCC1=CC=CC=C1O VBHDMJVUPJVYJZ-UHFFFAOYSA-N 0.000 claims description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 5
- 238000007599 discharging Methods 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 5
- 230000007935 neutral effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000007873 sieving Methods 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 239000000758 substrate Substances 0.000 claims description 5
- 238000000967 suction filtration Methods 0.000 claims description 5
- 239000006228 supernatant Substances 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 230000008569 process Effects 0.000 abstract description 3
- 238000011031 large-scale manufacturing process Methods 0.000 abstract description 2
- 239000003921 oil Substances 0.000 description 24
- 230000000052 comparative effect Effects 0.000 description 14
- 239000000839 emulsion Substances 0.000 description 10
- 229940092782 bentonite Drugs 0.000 description 4
- 229910000278 bentonite Inorganic materials 0.000 description 4
- 239000000440 bentonite Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000005189 flocculation Methods 0.000 description 4
- 230000016615 flocculation Effects 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- 150000003512 tertiary amines Chemical class 0.000 description 4
- 239000010779 crude oil Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000010802 sludge Substances 0.000 description 3
- 238000001179 sorption measurement Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 230000009471 action Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004581 coalescence Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000007764 o/w emulsion Substances 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 238000004062 sedimentation Methods 0.000 description 2
- 239000010865 sewage Substances 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
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
- C10G2300/00—Aspects relating to hydrocarbon processing covered by groups C10G1/00 - C10G99/00
- C10G2300/10—Feedstock materials
- C10G2300/1033—Oil well production fluids
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Separation Of Suspended Particles By Flocculating Agents (AREA)
Abstract
The invention belongs to the technical field of reverse demulsifiers, and particularly relates to a reverse demulsifier and a preparation method thereof. The reverse demulsifier consists of the following raw materials in percentage by mass: 21-23% of polyacrylate reverse demulsifier, 15-17% of modified bentonite, 11-12% of modified lignin surfactant, 5-8% of nonylphenol polyoxyethylene ether acrylate, 6-9% of cetyltrimethylammonium bromide, 4-7% of polyvinyl amine and the balance of water. The preparation method of the reverse demulsifier has the characteristics of low consumption, high demulsification speed, high oil-water separation capacity and high demulsification capacity, and is simple in process, easy to control preparation parameters and easy to realize large-scale production.
Description
Technical Field
The invention belongs to the technical field of reverse demulsifiers, and particularly relates to a reverse demulsifier and a preparation method thereof.
Background
The produced liquid of the oil field contains two different types of emulsions of water-in-oil (W/O) and oil-in-water (O/W), which causes difficult separation of oil and water. With the development of the petroleum industry in recent years, the water content of crude oil emulsions has increased significantly, particularly due to the application of enhanced water injection oil recovery techniques, especially thermal recovery techniques. In the prior art, various production increasing measures such as acidification, fracturing, water shutoff and profile control are implemented in the later and tertiary oil recovery stages of secondary oil recovery, injection of various chemical flooding and improvement of thick oil proportion are also more and more complicated, and the problems of oil-water separation and sewage oil removal of O/W type emulsion in the produced liquid are increasingly outstanding due to the application of various pumps in the process of exploitation and transportation.
The crude oil demulsifier adopted in the past is a demulsifier of the W/O emulsion, has no demulsification effect on the O/W emulsion, or has very low efficiency. Such demulsifiers for crude oil are commonly referred to as conventional demulsifiers. The reverse demulsifier is an oil-in-water emulsion demulsifier, and has high demulsification speed and high efficiency. The existing reverse demulsifier mainly comprises polyquaternary amine salts, polydicyanides, dendrimers PAM-AM, polyacrylamides, fatty alcohol-polyoxyethylene, phenolic resin blocks, PO-EO block modification and the like, but when high oil-water content is treated, the interfacial activity in water is limited, so that the dosage of the reverse demulsifier is large, the treatment time is long, and the treated water is difficult to reach standards.
Therefore, it is necessary to explore a novel reverse demulsifier.
Disclosure of Invention
The purpose of the invention is that: an inverse emulsion breaker is provided. The reverse demulsifier has the characteristics of small dosage, strong oil-water separation capability and high demulsification speed; the invention also provides a preparation method thereof.
The reverse demulsifier provided by the invention comprises the following raw materials in percentage by mass: 21-23% of polyacrylate reverse demulsifier, 15-17% of modified bentonite, 11-12% of modified lignin surfactant, 5-8% of nonylphenol polyoxyethylene ether acrylate, 6-9% of cetyltrimethylammonium bromide, 4-7% of polyvinyl amine and the balance of water.
Preferably, the reverse demulsifier provided by the invention comprises the following raw materials in percentage by mass: 22% of polyacrylate reverse demulsifier, 16% of modified bentonite, 12% of modified lignin surfactant, 7% of nonylphenol polyoxyethylene ether acrylate, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
Wherein:
the preparation method of the polyacrylate reverse demulsifier comprises the following steps: adding water, sodium dodecyl benzene sulfonate and potassium persulfate into a reaction kettle, introducing nitrogen, heating to 73-75 ℃ and stirring for 1.3-1.5h, adding styrene and stirring for reaction for 30-35min, then adding butyl methacrylate and continuously stirring for reaction for 30-35min, then adding methacrylic acid and stirring for reaction for 30-35min, finally adding tetrahydrofuran acrylate, reacting for 6.5-7h at 73-75 ℃, cooling, and discharging to obtain the polyacrylate reverse-phase demulsifier.
Wherein:
the mass sum of water, styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate is 100%, wherein the water accounts for 90%, the styrene accounts for 1.2%, the butyl methacrylate accounts for 2.3%, the methacrylic acid accounts for 5%, and the tetrahydrofuran acrylate accounts for 1.5%.
The mass of the potassium persulfate accounts for 0.8 percent of the sum of the mass of styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate; the mass of the sodium dodecyl benzene sulfonate accounts for 0.2 percent of the mass of the water.
The preparation method of the modified lignin surfactant comprises the following steps:
(1) Dripping dodecyl dimethyl tertiary amine into epoxy chloropropane, reacting for 10-10.5 hours at 18-20 ℃, performing reduced pressure distillation to remove redundant epoxy chloropropane after the reaction is finished, washing a product with anhydrous diethyl ether for 3-4 times, performing centrifugal separation, and then performing vacuum drying at 22-25 ℃ for 12-14 hours to prepare an intermediate;
(2) Adding sodium lignin sulfonate into acetone, heating to 45-48 ℃, dropwise adding sodium hydroxide solution to adjust the pH value of a reaction system to 11-12, preserving heat for 25-30min, heating to 53-55 ℃, adding the intermediate prepared in the step (1), stirring and reacting for 3.3-3.5h, and carrying out suction filtration, water washing and drying on the product after the reaction is finished to obtain the modified lignin surfactant.
Wherein:
the ratio of the amount of epichlorohydrin to the amount of dodecyldimethyl tertiary amine in the step (1) was 4.5:1.
The ratio of sodium lignin sulfonate in the step (2) to the amount of the substance of the intermediate prepared in the step (1) is 1:1.
In the step (2), the mass ratio of the sodium lignin sulfonate to the acetone is 1:3.
The preparation method of the modified bentonite comprises the following steps:
(1) adding hydrochloric acid into sodium bentonite for acidizing treatment, washing with water until the pH value of the filtrate is neutral after the treatment is finished, and then drying at 100-105 ℃ for 1.5-1.8h;
(2) adding aluminum sulfate solution into acidified sodium bentonite, stirring at constant temperature for 3-3.2h, standing for 48-50h, removing supernatant, drying substrate at 105-110deg.C for 3-3.2h, grinding, and sieving with 200 mesh sieve to obtain modified bentonite.
Wherein:
the temperature of the acidification treatment in the step (1) is 105-108 ℃ and the time is 4.5-5h; the concentration of hydrochloric acid is 0.02mol/L; the liquid-solid ratio of hydrochloric acid to sodium bentonite is 8:1.
After acidification treatment, sodium ions in the bentonite structure are exchanged by hydrogen ions in hydrochloric acid to partially form a molecular sieve, so that the adsorption performance of bentonite is improved.
The concentration of the aluminum sulfate solution in the step (2) is 0.1mol/L, and the mass ratio of the aluminum sulfate solution to the sodium bentonite is 2.5-2.6:1.
The preparation method of the reverse demulsifier provided by the invention comprises the following steps:
(1) Adding the modified lignin surfactant into water, stirring for 25-30min at 25-30 ℃, then adding the modified bentonite, and stirring and mixing uniformly;
(2) Stirring and mixing the polyacrylate reverse demulsifier, the acrylic acid nonylphenol polyoxyethylene ether ester, the cetyl trimethyl ammonium bromide and the polyvinyl amine uniformly;
(3) And (3) adding the mixed solution prepared in the step (2) into the step (1), and uniformly stirring and mixing to prepare the reverse demulsifier.
Wherein:
and (3) adding the modified bentonite into the step (1) and stirring and mixing for 40-45min.
In the step (2), the stirring and mixing temperature is 45-50 ℃, and the stirring and mixing time is 35-40min.
In the step (3), the stirring and mixing temperature is 20-25 ℃, and the stirring and mixing time is 55-60min.
Compared with the prior art, the invention has the following beneficial effects:
(1) The reverse demulsifier disclosed by the invention takes polyacrylate reverse demulsifier, modified bentonite and modified lignin surfactant as main reverse demulsifiers, and takes nonylphenol polyoxyethylene ether acrylate, cetyltrimethylammonium bromide and polyvinyl amine as auxiliary materials, so that the reverse demulsifier achieves a demulsification effect by compounding six raw materials. By adding a large amount of polyacrylate reverse demulsifier, because the polyacrylate reverse demulsifier contains lipophilic groups, hydrophilic-OH groups and the like, the hydrophilic groups and the lipophilic groups can adhere to the oil-water interface of the emulsion, the strength of the interface film is reduced, so that the interface film is destroyed, and then small oil drops in dirty oil water are aggregated and enlarged through bridging action, electric neutralization and flocculation aggregation, and are separated from the emulsion, so that the rapid demulsification is realized. However, if only the polyacrylate reverse demulsifier is used, a large amount of oil sludge is generated so as to adhere to a pipeline, so that the modified bentonite is necessary to be compounded, the modified bentonite is used as the reverse demulsifier and the flocculant to be compounded with other raw materials, the bentonite is modified through aluminum sulfate, high-valence cations in the aluminum sulfate are adsorbed on the surface of the bentonite to form a compression double electric layer, and oil drops in the dirty water are gathered through the action of the compression double electric layer, thereby realizing demulsification and deoiling. In addition, the modified bentonite also has flocculation effect, and the adsorption performance of the bentonite is enhanced through the modification treatment of aluminum sulfate, so that the produced oil sludge can be adsorbed, the sedimentation speed of the oil sludge is accelerated, and the floccules are firm. The modified lignin surfactant has strong dispersion capability, has good solubility in any pH value range, widens the application range of the prepared reverse demulsifier, ensures the use stability of the prepared reverse demulsifier, has certain foamability, can shorten the time for destroying the O/W emulsion oil-water interfacial film, reduces the strength of the oil drop interfacial film, and promotes the aggregation of oil drops.
(2) According to the reverse demulsifier disclosed by the invention, the addition of the nonylphenol polyoxyethylene ether acrylate ensures that oil drops have better fluidity, the viscosity of formed floccules is greatly reduced, the linear alkyl in the cetyltrimethylammonium bromide enters the inside of emulsified oil drops, the strength of an interface film and the stability of emulsion are reduced, and the coalescence among the oil drops is easier. The cationic charge density of the polyvinyl amine is high, and the negative charge on the surfaces of oil drops of oily sewage can be neutralized, so that flocculation and coalescence of the oil drops are promoted, and in addition, the polyvinyl amine can generate more stretching molecular chains in water, so that flocculation adsorption and bridging capacity of suspended particles are improved, sedimentation rate is accelerated, and floc size is increased.
(3) The preparation method of the reverse demulsifier has the characteristics of low consumption, high demulsification speed, high oil-water separation capacity and high demulsification capacity, and is simple in process, easy to control preparation parameters and easy to realize large-scale production.
Detailed Description
The invention is further described below with reference to examples.
Example 1
The reverse demulsifier of the embodiment 1 comprises the following raw materials in percentage by mass: 22% of polyacrylate reverse demulsifier, 16% of modified bentonite, 12% of modified lignin surfactant, 7% of nonylphenol polyoxyethylene ether acrylate, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
Wherein:
the preparation method of the polyacrylate reverse demulsifier comprises the following steps: adding water, sodium dodecyl benzene sulfonate and potassium persulfate into a reaction kettle, introducing nitrogen, heating to 74 ℃ and stirring for 1.4 hours, adding styrene and stirring for reaction for 33 minutes, then adding butyl methacrylate and continuously stirring for reaction for 33 minutes, then adding methacrylic acid and stirring for reaction for 33 minutes, finally adding tetrahydrofuran acrylate, reacting for 6.8 hours at 74 ℃, cooling, and discharging to obtain the polyacrylate reverse-phase demulsifier.
Wherein:
the mass sum of water, styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate is 100%, wherein the water accounts for 90%, the styrene accounts for 1.2%, the butyl methacrylate accounts for 2.3%, the methacrylic acid accounts for 5%, and the tetrahydrofuran acrylate accounts for 1.5%.
The mass of the potassium persulfate accounts for 0.8 percent of the sum of the mass of styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate; the mass of the sodium dodecyl benzene sulfonate accounts for 0.2 percent of the mass of the water.
The preparation method of the modified lignin surfactant comprises the following steps:
(1) Dropwise adding dodecyl dimethyl tertiary amine into epoxy chloropropane, reacting at 19 ℃ for 10.3 hours, performing reduced pressure distillation to remove redundant epoxy chloropropane after the reaction is finished, washing a product with anhydrous diethyl ether for 3 times, performing centrifugal separation, and then performing vacuum drying at 23 ℃ for 13 hours to prepare an intermediate;
(2) Adding sodium lignin sulfonate into acetone, heating to 47 ℃, dropwise adding sodium hydroxide solution to adjust the pH value of a reaction system to 11, preserving heat for 27min, heating to 54 ℃, adding the intermediate prepared in the step (1), stirring and reacting for 3.4h, and carrying out suction filtration, water washing and drying on the product after the reaction is finished to prepare the modified lignin surfactant.
Wherein:
the ratio of the amount of epichlorohydrin to the amount of dodecyldimethyl tertiary amine in the step (1) was 4.5:1.
The ratio of sodium lignin sulfonate in the step (2) to the amount of the substance of the intermediate prepared in the step (1) is 1:1.
In the step (2), the mass ratio of the sodium lignin sulfonate to the acetone is 1:3.
The preparation method of the modified bentonite comprises the following steps:
(1) adding hydrochloric acid into sodium bentonite for acidizing treatment, washing with water until the pH value of the filtrate is neutral after the treatment is finished, and then drying at 103 ℃ for 1.7h;
(2) adding the aluminum sulfate solution into the acidified sodium bentonite, stirring for 3.1h at constant temperature, standing for 49h, removing supernatant, drying the substrate at 108 ℃ for 3.1h, grinding, and sieving with a 200-mesh sieve to obtain the modified bentonite.
Wherein:
the temperature of the acidification treatment in the step (1) is 107 ℃ and the time is 4.7h; the concentration of hydrochloric acid is 0.02mol/L; the liquid-solid ratio of hydrochloric acid to sodium bentonite is 8:1.
The concentration of the aluminum sulfate solution in the step (2) is 0.1mol/L, and the mass ratio of the aluminum sulfate solution to the sodium bentonite is 2.55:1.
The preparation method of the reverse demulsifier of the embodiment 1 comprises the following steps:
(1) Adding the modified lignin surfactant into water, stirring for 28min at 28 ℃, then adding the modified bentonite, and stirring and mixing uniformly;
(2) Stirring and mixing the polyacrylate reverse demulsifier, the acrylic acid nonylphenol polyoxyethylene ether ester, the cetyl trimethyl ammonium bromide and the polyvinyl amine uniformly;
(3) And (3) adding the mixed solution prepared in the step (2) into the step (1), and uniformly stirring and mixing to prepare the reverse demulsifier.
Wherein:
and (3) adding the modified bentonite into the step (1), and stirring and mixing for 43min.
In the step (2), the stirring and mixing temperature is 47 ℃, and the stirring and mixing time is 38min.
In the step (3), the stirring and mixing temperature is 20 ℃, and the stirring and mixing time is 60 minutes.
Example 2
The reverse demulsifier of the embodiment 2 comprises the following raw materials in percentage by mass: 21% of polyacrylate reverse demulsifier, 15% of modified bentonite, 11% of modified lignin surfactant, 5% of nonylphenol polyoxyethylene ether acrylate, 9% of cetyltrimethylammonium bromide, 7% of polyvinyl amine and the balance of water.
Wherein:
the preparation method of the polyacrylate reverse demulsifier comprises the following steps: adding water, sodium dodecyl benzene sulfonate and potassium persulfate into a reaction kettle, introducing nitrogen, heating to 73 ℃, stirring for 1.5h, adding styrene, stirring and reacting for 35min, then adding butyl methacrylate, continuously stirring and reacting for 35min, then adding methacrylic acid, stirring and reacting for 35min, finally adding tetrahydrofuran acrylate, reacting for 7h at 73 ℃, cooling, and discharging to obtain the polyacrylate reverse-phase demulsifier.
Wherein:
the mass sum of water, styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate is 100%, wherein the water accounts for 90%, the styrene accounts for 1.2%, the butyl methacrylate accounts for 2.3%, the methacrylic acid accounts for 5%, and the tetrahydrofuran acrylate accounts for 1.5%.
The mass of the potassium persulfate accounts for 0.8 percent of the sum of the mass of styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate; the mass of the sodium dodecyl benzene sulfonate accounts for 0.2 percent of the mass of the water.
The preparation method of the modified lignin surfactant comprises the following steps:
(1) Dropwise adding dodecyl dimethyl tertiary amine into epoxy chloropropane, reacting at 18 ℃ for 10.5 hours, performing reduced pressure distillation to remove redundant epoxy chloropropane after the reaction is finished, washing a product with anhydrous diethyl ether for 3 times, performing centrifugal separation, and then performing vacuum drying at 22 ℃ for 12 hours to prepare an intermediate;
(2) Adding sodium lignin sulfonate into acetone, heating to 45 ℃, dropwise adding sodium hydroxide solution to adjust the pH value of a reaction system to 12, preserving heat for 25min, heating to 53 ℃, adding the intermediate prepared in the step (1), stirring and reacting for 3.3h, and carrying out suction filtration, water washing and drying on the product after the reaction is finished to prepare the modified lignin surfactant.
Wherein:
the ratio of the amount of epichlorohydrin to the amount of dodecyldimethyl tertiary amine in the step (1) was 4.5:1.
The ratio of sodium lignin sulfonate in the step (2) to the amount of the substance of the intermediate prepared in the step (1) is 1:1.
In the step (2), the mass ratio of the sodium lignin sulfonate to the acetone is 1:3.
The preparation method of the modified bentonite comprises the following steps:
(1) adding hydrochloric acid into sodium bentonite for acidizing treatment, washing with water until the pH value of the filtrate is neutral after the treatment is finished, and then drying at 100 ℃ for 1.8h;
(2) adding the aluminum sulfate solution into the acidified sodium bentonite, stirring for 3 hours at constant temperature, standing for 50 hours, removing supernatant, drying a substrate at 105 ℃ for 3.2 hours, grinding and sieving with a 200-mesh sieve to prepare the modified bentonite.
Wherein:
the temperature of the acidification treatment in the step (1) is 105 ℃ and the time is 4.5h; the concentration of hydrochloric acid is 0.02mol/L; the liquid-solid ratio of hydrochloric acid to sodium bentonite is 8:1.
The concentration of the aluminum sulfate solution in the step (2) is 0.1mol/L, and the mass ratio of the aluminum sulfate solution to the sodium bentonite is 2.5:1.
The preparation method of the reverse demulsifier described in the embodiment 2 comprises the following steps:
(1) Adding the modified lignin surfactant into water, stirring for 30min at 30 ℃, then adding the modified bentonite, and stirring and mixing uniformly;
(2) Stirring and mixing the polyacrylate reverse demulsifier, the acrylic acid nonylphenol polyoxyethylene ether ester, the cetyl trimethyl ammonium bromide and the polyvinyl amine uniformly;
(3) And (3) adding the mixed solution prepared in the step (2) into the step (1), and uniformly stirring and mixing to prepare the reverse demulsifier.
Wherein:
and (3) adding the modified bentonite into the step (1) and stirring and mixing for 40min.
In the step (2), the stirring and mixing temperature is 45 ℃, and the stirring and mixing time is 40min.
In the step (3), the stirring and mixing temperature is 25 ℃, and the stirring and mixing time is 55min.
Example 3
The reverse demulsifier described in the embodiment 3 comprises the following raw materials in percentage by mass: 23% of polyacrylate reverse demulsifier, 17% of modified bentonite, 11% of modified lignin surfactant, 8% of nonylphenol polyoxyethylene ether acrylate, 6% of cetyltrimethylammonium bromide, 4% of polyvinyl amine and the balance of water.
Wherein:
the preparation method of the polyacrylate reverse demulsifier comprises the following steps: adding water, sodium dodecyl benzene sulfonate and potassium persulfate into a reaction kettle, introducing nitrogen, heating to 75 ℃, stirring for 1.3 hours, adding styrene, stirring and reacting for 30 minutes, then adding butyl methacrylate, continuously stirring and reacting for 30 minutes, then adding methacrylic acid, stirring and reacting for 30 minutes, finally adding tetrahydrofuran acrylate, reacting for 6.5 hours at 75 ℃, cooling, and discharging to obtain the polyacrylate reverse-phase demulsifier.
Wherein:
the mass sum of water, styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate is 100%, wherein the water accounts for 90%, the styrene accounts for 1.2%, the butyl methacrylate accounts for 2.3%, the methacrylic acid accounts for 5%, and the tetrahydrofuran acrylate accounts for 1.5%.
The mass of the potassium persulfate accounts for 0.8 percent of the sum of the mass of styrene, butyl methacrylate, methacrylic acid and tetrahydrofuran acrylate; the mass of the sodium dodecyl benzene sulfonate accounts for 0.2 percent of the mass of the water.
The preparation method of the modified lignin surfactant comprises the following steps:
(1) Dropwise adding dodecyl dimethyl tertiary amine into epoxy chloropropane, reacting for 10 hours at 20 ℃, performing reduced pressure distillation to remove redundant epoxy chloropropane after the reaction is finished, washing a product with anhydrous diethyl ether for 4 times, performing centrifugal separation, and then performing vacuum drying for 14 hours at 25 ℃ to prepare an intermediate;
(2) Adding sodium lignin sulfonate into acetone, heating to 48 ℃, dropwise adding sodium hydroxide solution to adjust the pH value of a reaction system to 11, preserving heat for 30min, heating to 55 ℃, adding the intermediate prepared in the step (1), stirring and reacting for 3.5h, and carrying out suction filtration, water washing and drying on the product after the reaction is finished to prepare the modified lignin surfactant.
Wherein:
the ratio of the amount of epichlorohydrin to the amount of dodecyldimethyl tertiary amine in the step (1) was 4.5:1.
The ratio of sodium lignin sulfonate in the step (2) to the amount of the substance of the intermediate prepared in the step (1) is 1:1.
In the step (2), the mass ratio of the sodium lignin sulfonate to the acetone is 1:3.
The preparation method of the modified bentonite comprises the following steps:
(1) adding hydrochloric acid into sodium bentonite for acidizing treatment, washing with water until the pH value of the filtrate is neutral after the treatment is finished, and then drying at 105 ℃ for 1.5h;
(2) adding the aluminum sulfate solution into the acidified sodium bentonite, stirring for 3.2 hours at constant temperature, standing for 48 hours, removing supernatant, drying a substrate at 110 ℃ for 3 hours, grinding and sieving with a 200-mesh sieve to prepare the modified bentonite.
Wherein:
the temperature of the acidification treatment in the step (1) is 108 ℃ and the time is 4.5h; the concentration of hydrochloric acid is 0.02mol/L; the liquid-solid ratio of hydrochloric acid to sodium bentonite is 8:1.
The concentration of the aluminum sulfate solution in the step (2) is 0.1mol/L, and the mass ratio of the aluminum sulfate solution to the sodium bentonite is 2.6:1.
The preparation method of the reverse demulsifier in the embodiment 3 comprises the following steps:
(1) Adding the modified lignin surfactant into water, stirring for 25min at 25 ℃, then adding the modified bentonite, and stirring and mixing uniformly;
(2) Stirring and mixing the polyacrylate reverse demulsifier, the acrylic acid nonylphenol polyoxyethylene ether ester, the cetyl trimethyl ammonium bromide and the polyvinyl amine uniformly;
(3) And (3) adding the mixed solution prepared in the step (2) into the step (1), and uniformly stirring and mixing to prepare the reverse demulsifier.
Wherein:
and (3) adding the modified bentonite into the step (1), and stirring and mixing for 45min.
In the step (2), the stirring and mixing temperature is 50 ℃, and the stirring and mixing time is 35min.
In the step (3), the stirring and mixing temperature is 23 ℃, and the stirring and mixing time is 58min.
Comparative example 1
The preparation method of the reverse demulsifier according to the comparative example 1 is the same as that of example 1, except that the raw material composition of the reverse demulsifier is different. The reverse demulsifier of the comparative example 1 comprises the following raw materials in percentage by mass: 22% of polyacrylate reverse demulsifier, 12% of modified lignin surfactant, 7% of nonylphenol polyoxyethylene ether acrylate, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
Comparative example 2
The preparation method of the reverse demulsifier according to the comparative example 2 is the same as that of example 1, except that the raw material composition of the reverse demulsifier is different. The reverse demulsifier of the comparative example 2 comprises the following raw materials in percentage by mass: 22% of polyacrylate reverse demulsifier, 16% of modified bentonite, 7% of acrylic nonylphenol polyoxyethylene ether ester, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
Comparative example 3
The reverse demulsifier of comparative example 3 was prepared in the same manner as in example 1, except that the reverse demulsifier was different in the composition of the raw materials. The reverse demulsifier of the comparative example 3 comprises the following raw materials in percentage by mass: 16% of modified bentonite, 12% of modified lignin surfactant, 7% of nonylphenol polyoxyethylene ether acrylate, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
Referring to China oil and gas industry standard SY/T5797-93 "method for evaluating the use performance of oil-in-water emulsion demulsifier", the reverse demulsifier prepared in examples 1-3 and comparative examples 1-3 was subjected to performance test by taking a polymer flooding produced liquid of a winning oil field as a test medium, wherein the oil content was 2365mg/L, the test temperature was 50 ℃, the standing time was 10min, and the test results are shown in the following Table 1:
TABLE 1 results of Performance test of examples 1-3 and comparative examples 1-3
As can be seen from the above Table 1, the reverse demulsifiers prepared in examples 1 to 3 were significantly superior in performance to the reverse demulsifiers prepared in comparative examples 1 to 3; comparative example 1 and comparative examples 1-3 show that there is a synergistic relationship between the polyacrylate reverse demulsifier, the modified bentonite, and the modified lignin surfactant. Therefore, the reverse demulsifier raw materials have synergistic effect, so that the prepared reverse demulsifier has the characteristics of small dosage, high demulsification speed, high oil-water separation capability and strong demulsification capability.
Claims (7)
1. An inverse demulsifier, characterized in that: the material consists of the following raw materials in percentage by mass: 21-23% of polyacrylate reverse demulsifier, 15-17% of modified bentonite, 11-12% of modified lignin surfactant, 5-8% of nonylphenol polyoxyethylene ether acrylate, 6-9% of cetyltrimethylammonium bromide, 4-7% of polyvinyl amine and the balance of water;
wherein:
the preparation method of the polyacrylate reverse demulsifier comprises the following steps: adding water, sodium dodecyl benzene sulfonate and potassium persulfate into a reaction kettle, introducing nitrogen, heating to 73-75 ℃ and stirring for 1.3-1.5h, adding styrene and stirring for reacting for 30-35min, then adding butyl methacrylate and continuously stirring for reacting for 30-35min, then adding methacrylic acid and stirring for reacting for 30-35min, finally adding tetrahydrofuran acrylate, reacting for 6.5-7h at 73-75 ℃, cooling, discharging, and preparing the polyacrylate reverse-phase demulsifier;
the preparation method of the modified lignin surfactant comprises the following steps:
(1) Dripping dodecyl dimethyl tertiary amine into epoxy chloropropane, reacting for 10-10.5 hours at 18-20 ℃, performing reduced pressure distillation to remove redundant epoxy chloropropane after the reaction is finished, washing a product with anhydrous diethyl ether for 3-4 times, performing centrifugal separation, and then performing vacuum drying at 22-25 ℃ for 12-14 hours to prepare an intermediate;
(2) Adding sodium lignin sulfonate into acetone, heating to 45-48 ℃, dropwise adding sodium hydroxide solution to adjust the pH value of a reaction system to 11-12, preserving heat for 25-30min, heating to 53-55 ℃, adding the intermediate prepared in the step (1), stirring and reacting for 3.3-3.5h, and carrying out suction filtration, water washing and drying on a product after the reaction is finished to prepare the modified lignin surfactant;
the preparation method of the modified bentonite comprises the following steps:
(1) adding hydrochloric acid into sodium bentonite for acidizing treatment, washing with water until the pH value of the filtrate is neutral after the treatment is finished, and then drying at 100-105 ℃ for 1.5-1.8h;
(2) adding aluminum sulfate solution into acidified sodium bentonite, stirring at constant temperature for 3-3.2h, standing for 48-50h, removing supernatant, drying substrate at 105-110deg.C for 3-3.2h, grinding, and sieving with 200 mesh sieve to obtain modified bentonite.
2. The reverse demulsifier of claim 1, wherein: the material consists of the following raw materials in percentage by mass: 22% of polyacrylate reverse demulsifier, 16% of modified bentonite, 12% of modified lignin surfactant, 7% of nonylphenol polyoxyethylene ether acrylate, 8% of cetyltrimethylammonium bromide, 5% of polyvinyl amine and the balance of water.
3. The reverse demulsifier of claim 1, wherein: the mass sum of water, styrene, butyl methacrylate, methacrylic acid and acrylic acid tetrahydrofuran ester is 100%, wherein the water accounts for 90%, the styrene accounts for 1.2%, the butyl methacrylate accounts for 2.3%, the methacrylic acid accounts for 5%, and the acrylic acid tetrahydrofuran ester accounts for 1.5%;
in the preparation method of the polyacrylate reverse demulsifier, the mass of potassium persulfate accounts for 0.8% of the sum of the mass of styrene, butyl methacrylate, methacrylic acid and acrylic acid tetrahydrofuranyl; the mass of the sodium dodecyl benzene sulfonate accounts for 0.2 percent of the mass of the water.
4. The reverse demulsifier of claim 1, wherein: the ratio of the mass of the epichlorohydrin to the dodecyl dimethyl tertiary amine in the step (1) of the preparation method of the modified lignin surfactant is 4.5:1;
the ratio of the sodium lignin sulfonate in the step (2) to the substances of the intermediate prepared in the step (1) is 1:1;
in the step (2) of the preparation method of the modified lignin surfactant, the mass ratio of sodium lignin sulfonate to acetone is 1:3.
5. The reverse demulsifier of claim 1, wherein: the acidification treatment temperature in the step (1) of the preparation method of the modified bentonite is 105-108 ℃ and the time is 4.5-5h; the concentration of hydrochloric acid is 0.02mol/L; the liquid-solid ratio of hydrochloric acid to sodium bentonite is 8:1;
the concentration of the aluminum sulfate solution in the step (2) of the preparation method of the modified bentonite is 0.1mol/L, and the mass ratio of the aluminum sulfate solution to the sodium bentonite is 2.5-2.6:1.
6. A method for preparing the reverse demulsifier as defined in claim 1, which is characterized in that: the method comprises the following steps:
(1) Adding the modified lignin surfactant into water, stirring for 25-30min at 25-30 ℃, then adding the modified bentonite, and stirring and mixing uniformly;
(2) Stirring and mixing the polyacrylate reverse demulsifier, the acrylic acid nonylphenol polyoxyethylene ether ester, the cetyl trimethyl ammonium bromide and the polyvinyl amine uniformly;
(3) And (3) adding the mixed solution prepared in the step (2) into the step (1), and uniformly stirring and mixing to prepare the reverse demulsifier.
7. The method for preparing the reverse demulsifier according to claim 6, wherein: adding modified bentonite into the step (1), and stirring and mixing for 40-45min;
in the step (2), stirring and mixing temperature is 45-50 ℃, and stirring and mixing time is 35-40min;
in the step (3), the stirring and mixing temperature is 20-25 ℃, and the stirring and mixing time is 55-60min.
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|---|---|---|---|---|
| GB1065972A (en) * | 1963-08-03 | 1967-04-19 | Basf Ag | Production of polymerised tetrahydrofuryl compounds |
| CN101838370A (en) * | 2010-02-12 | 2010-09-22 | 长兴化学工业(中国)有限公司 | Aqueous concoction, aqueous polymer emulsion prepared from same and application thereof |
| CN114891151A (en) * | 2022-05-18 | 2022-08-12 | 中海油(天津)油田化工有限公司 | Organic silicon modified polyacrylate emulsion type reverse demulsifier and preparation method thereof |
| CN115466360A (en) * | 2022-11-15 | 2022-12-13 | 山东东临新材料股份有限公司 | Preparation method of SiO2/ACR nano composite material |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US7413583B2 (en) * | 2003-08-22 | 2008-08-19 | The Lubrizol Corporation | Emulsified fuels and engine oil synergy |
| US7309684B2 (en) * | 2005-05-12 | 2007-12-18 | The Lubrizol Corporation | Oil-in-water emulsified remover comprising an ethoxylated alcohol surfactant |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1065972A (en) * | 1963-08-03 | 1967-04-19 | Basf Ag | Production of polymerised tetrahydrofuryl compounds |
| CN101838370A (en) * | 2010-02-12 | 2010-09-22 | 长兴化学工业(中国)有限公司 | Aqueous concoction, aqueous polymer emulsion prepared from same and application thereof |
| CN114891151A (en) * | 2022-05-18 | 2022-08-12 | 中海油(天津)油田化工有限公司 | Organic silicon modified polyacrylate emulsion type reverse demulsifier and preparation method thereof |
| CN115466360A (en) * | 2022-11-15 | 2022-12-13 | 山东东临新材料股份有限公司 | Preparation method of SiO2/ACR nano composite material |
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