CN109289695B - Carboxylic acid surfactant and preparation method and application thereof - Google Patents
Carboxylic acid surfactant and preparation method and application thereof Download PDFInfo
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- CN109289695B CN109289695B CN201811123709.5A CN201811123709A CN109289695B CN 109289695 B CN109289695 B CN 109289695B CN 201811123709 A CN201811123709 A CN 201811123709A CN 109289695 B CN109289695 B CN 109289695B
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- carboxylic acid
- acid surfactant
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- polyethylene glycol
- maleic anhydride
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- 239000004094 surface-active agent Substances 0.000 title claims abstract description 40
- 150000001732 carboxylic acid derivatives Chemical class 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title abstract description 8
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 230000032683 aging Effects 0.000 claims abstract description 24
- 239000004576 sand Substances 0.000 claims abstract description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 19
- 239000002202 Polyethylene glycol Substances 0.000 claims abstract description 19
- 229920001223 polyethylene glycol Polymers 0.000 claims abstract description 19
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000243 solution Substances 0.000 claims abstract description 18
- 229910001870 ammonium persulfate Inorganic materials 0.000 claims abstract description 16
- JHUFGBSGINLPOW-UHFFFAOYSA-N 3-chloro-4-(trifluoromethoxy)benzoyl cyanide Chemical compound FC(F)(F)OC1=CC=C(C(=O)C#N)C=C1Cl JHUFGBSGINLPOW-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000000178 monomer Substances 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 12
- 239000011259 mixed solution Substances 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 6
- 238000004519 manufacturing process Methods 0.000 claims abstract description 6
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- 238000001816 cooling Methods 0.000 claims abstract description 4
- 230000003472 neutralizing effect Effects 0.000 claims abstract description 4
- 238000004321 preservation Methods 0.000 claims abstract description 4
- 239000007864 aqueous solution Substances 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- 229910001873 dinitrogen Inorganic materials 0.000 claims 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 1
- 238000011534 incubation Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000001012 protector Effects 0.000 claims 1
- 239000003921 oil Substances 0.000 description 24
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004927 clay Substances 0.000 description 3
- 239000013043 chemical agent Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000005411 Van der Waals force Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000012496 blank sample Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- BWYYYTVSBPRQCN-UHFFFAOYSA-M sodium;ethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=C BWYYYTVSBPRQCN-UHFFFAOYSA-M 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/065—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to unsaturated polyethers, polyoxymethylenes or polyacetals
-
- 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
- C10G29/00—Refining of hydrocarbon oils, in the absence of hydrogen, with other chemicals
- C10G29/20—Organic compounds not containing metal atoms
- C10G29/28—Organic compounds not containing metal atoms containing sulfur as the only hetero atom, e.g. mercaptans, or sulfur and oxygen as the only hetero atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Materials Engineering (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a carboxylic acid surfactant and a preparation method and application thereof, wherein the preparation of the carboxylic acid surfactant comprises the following steps: under the conditions of heating, stirring and inert gas protection, uniformly dropwise adding a mixed solution of allyl polyethylene glycol and maleic anhydride monomer while uniformly dropwise adding an initiator ammonium persulfate solution in an sodium allylsulfonate solution, after dropwise adding is completed, carrying out heat preservation reaction for a period of time, cooling, and then neutralizing the pH value to 7 to obtain the carboxylic acid surfactant. When the carboxylic acid surfactant is applied, the carboxylic acid surfactant is added into the aging oil to remove sand and dewater. The fine sand in the aging oil is separated out through chemical reaction, the separated sand can be discharged to a water treatment system along with water, the treated production water is directly discharged, the post-treatment is relatively simple, and the treated aging oil contains less water and meets the requirement of external transportation.
Description
Technical Field
The invention belongs to the technical field of oilfield chemistry, and particularly relates to a carboxylic acid surfactant, and a preparation method and application thereof.
Background
In the production process of offshore oil fields, the long-term exploitation may cause the failure of the underground sand control device, so that the produced crude oil contains sand or clay, the oil-water separation effect can be seriously influenced by the sand, and the crude oil which is difficult to treat can become sand-containing aging oil which is difficult to treat after being stored in a storage tank for a long time. The common method for treating aging oil in oil field at present is mechanical method-cyclone centrifugal method, which removes sand in crude oil through density difference of crude oil and sand.
Disclosure of Invention
The invention aims to provide a carboxylic acid surfactant, and a preparation method and application thereof. The invention adopts a chemical desanding method, adds a small amount of chemical agent into the aging oil, separates out fine sand in the aging oil through chemical reaction, the separated sand can be discharged to a water treatment system along with water, and the treated production water is directly discharged, the post-treatment is relatively simple, and the treated aging oil contains less water, thereby meeting the requirement of external transportation.
In order to solve the problems, the invention adopts the following technical scheme:
a carboxylic acid surfactant characterized by the structural formula:
wherein: n is 6 to 7; a is 56-58, b is 163-245, and c is 83-139.
The invention also provides a preparation method of the carboxylic acid surfactant, which comprises the following steps: under the conditions of heating, stirring and inert gas protection, uniformly dropwise adding a mixed solution of allyl polyethylene glycol and maleic anhydride monomer while uniformly dropwise adding an initiator ammonium persulfate solution in an sodium allylsulfonate solution, after dropwise adding is completed, carrying out heat preservation reaction for a period of time, cooling, and then neutralizing the pH value to 7 to obtain the carboxylic acid surfactant.
Further, the addition amounts of the respective substances were as follows: allyl polyethylene glycol monomer: allyl polyethylene glycol: maleic anhydride: sodium allyl sulfonate: the mass ratio of ammonium persulfate is as follows: 1:1: 0.8-1.2: 0.6-1.0: 0.06-0.12.
Further, the concentration of the sodium allylsulfonate solution and the concentration of the ammonium persulfate solution are both 20wt% aqueous solutions; the mixed solution of the allyl polyethylene glycol and the maleic anhydride monomer is a mixed solution of 20wt% of allyl polyethylene glycol aqueous solution and 20wt% of maleic anhydride monomer aqueous solution.
Further, the heating temperature is 85 ℃; the stirring speed is 150r/min, and the inert gas is nitrogen.
Further, the time for uniformly dripping is 4 hours, and the time for heat preservation reaction is 3 hours.
Further, the pH was neutralized to 7 with 40% NaOH solution.
Further, the prepared sodium allylsulfonate aqueous solution is placed in a four-neck flask, a thermometer, a stirrer, a condensing device, a dropping funnel and a nitrogen protection device are arranged, stirring is continuously carried out, the temperature is raised to 85 ℃, and while dropping the mixed solution of allyl polyethylene glycol and maleic anhydride monomer, a solution of initiator ammonium persulfate is dropped.
The invention also provides application of the carboxylic acid surfactant, which is characterized in that the carboxylic acid surfactant is added into aging oil to remove sand and dewater.
Further, the carboxylic acid surfactant was added in an amount of 40ppm in the aging oil.
The invention principle is as follows:
the sand removing principle of the surfactant is as follows: part of polar groups carried by the carboxylic acid surfactant, such as ester groups, -OH, -COO-and the like, are tightly adsorbed on the surfaces of the fine sand particles with strong polarity through ionic bonds, covalent bonds, hydrogen bonds, van der Waals force and other interactions, and the rest polar groups, -SO3-, -COO-and the like show extremely strong hydrophilicity, SO that the fine sand particles are favorably separated from the oil phase and enter the water phase. In brief, the carboxylic acid water reducing agent can maintain the stability of a dispersion system through a steric repulsive force. The carboxylic acid surfactant mainly takes the clay or silt in the oil into the water phase through the chemical bond effect, so that the effect of removing the clay or silt in the oil is achieved, and the action mode and the action principle of the carboxylic acid surfactant are different.
Advantageous effects
The invention adopts allyl polyethylene glycol (AEO), maleic anhydride and sodium vinylsulfonate as polymerization monomers, and aqueous solution free radical polymerization is carried out to synthesize a series of polycarboxylic acid surfactants. The chemical desanding method is adopted, the chemical agent is added into the aging oil, the sand in the aging oil is separated out through chemical reaction, the separated sand can be discharged to a water treatment system directly, the post-treatment operation is simple, the water content of the treated aging oil is low, and the aging oil can reach the output standard.
The carboxylic acid surfactant disclosed by the invention is simple in preparation process and low in production cost.
Detailed Description
The invention will be further illustrated with reference to specific embodiments. It should be understood that these examples are for illustrative purposes only and are not intended to limit the scope of the present invention. Further, it should be understood that various changes or modifications of the present invention may be made by those skilled in the art after reading the teaching of the present invention, and such equivalents may fall within the scope of the present invention as defined in the appended claims.
Example 1
Preparing 20g of allyl polyethylene glycol, 20g of maleic anhydride, 16g of sodium allylsulfonate and 1.8g of initiator ammonium persulfate into 20% aqueous solution by using distilled water respectively; placing the prepared sodium allylsulfonate into a 500ml four-neck flask, installing a thermometer, a stirrer, a condensing device, a dropping funnel and a nitrogen protection device, continuously stirring and heating to 85 ℃, dropwise adding a mixed solution of allyl polyethylene glycol and a maleic anhydride monomer while dropwise adding an initiator ammonium persulfate solution, uniformly dropwise adding the initiator ammonium persulfate solution for 4 hours, preserving the temperature for 3 hours, cooling, and neutralizing the pH value to 7 with a 40% NaOH solution to obtain the carboxylic acid surfactant CS-01.
Wherein: n is approximately equal to 7; a is approximately equal to 57; b ≈ 204; c ≈ 111
Synthesizing carboxylic acid surfactants with different molecular weights and different branched chain structures by adjusting the mass ratio of allyl polyethylene glycol, maleic anhydride, sodium allylsulfonate and initiator ammonium persulfate:
when the mass ratio of allyl polyethylene glycol, maleic anhydride, sodium allyl sulfonate and initiator ammonium persulfate is 1.0: 0.8: 1.0: at 0.06, the prepared carboxylic acid surfactant is CS-02;
wherein: n is approximately equal to 6; a is approximately equal to 58; b ≈ 163; c ≈ 139
When the mass ratio of allyl polyethylene glycol, maleic anhydride, sodium allyl sulfonate and initiator ammonium persulfate is 1.0: 1.2: 0.6: when 0.09, the prepared carboxylic acid surfactant is CS-03;
wherein: n is approximately equal to 7; a is approximately equal to 57; b is approximately equal to 245; c is approximately equal to 83
When the mass ratio of allyl polyethylene glycol, maleic anhydride, sodium allyl sulfonate and initiator ammonium persulfate is 1.0: 1.0: 0.6: at 0.12, CS-04 was the carboxylic acid surfactant prepared.
Wherein: n is approximately equal to 7; a is approximately equal to 57; b ≈ 204; c is approximately equal to 83
Example 2:
the carboxylic acid surfactants with different molecular weights and different branched chain structures prepared in example 1 were subjected to aging oil desanding and dehydrating experiments, and compared with a blank sample without a medicament, wherein the experiment temperature is 80 ℃, the sand content of the aging oil used in the experiments is 1.2%, the comprehensive water content is 2.5%, and the experimental results are as follows:
the experiments prove that the prepared carboxylic acid surfactants CS-01, CS-02, CS-03 and CS-04 have good degritting and dehydrating effects on the aging oil, when the dosing concentration is not less than 30ppm, the degritting rate of the aging oil is not less than 87.5%, the water content of the aging oil after the experiments is not more than 0.5%, and the water content of the aging oil is qualified; the CS-01 has the best effect under the same medicament adding concentration, when the adding concentration is 40ppm, the sand removal rate of the aging oil is 95.8%, and the water content of the aging oil after the experiment is 0.3%.
Claims (10)
1. A carboxylic acid surfactant characterized by the structural formula:
wherein: n is 6 to 7; a is 56-58, b is 163-245, and c is 83-139.
2. The process for producing a carboxylic acid surfactant as claimed in claim 1, which comprises the steps of: under the conditions of heating, stirring and inert gas protection, uniformly dropwise adding a mixed solution of allyl polyethylene glycol and maleic anhydride monomer while uniformly dropwise adding an initiator ammonium persulfate solution in an sodium allylsulfonate solution, after dropwise adding is completed, carrying out heat preservation reaction for a period of time, cooling, and then neutralizing the pH value to 7 to obtain the carboxylic acid surfactant.
3. The process for producing a carboxylic acid surfactant as claimed in claim 2, wherein the following are added: allyl polyethylene glycol monomer: allyl polyethylene glycol: maleic anhydride: sodium allyl sulfonate: the mass ratio of ammonium persulfate is as follows: 1:1: 0.8-1.2: 0.6-1.0: 0.06-0.12.
4. The method for preparing carboxylic acid surfactant according to claim 3, wherein the sodium allylsulfonate solution and the ammonium persulfate solution are both 20wt% aqueous solutions; the mixed solution of the allyl polyethylene glycol and the maleic anhydride monomer is a mixed solution of 20wt% of allyl polyethylene glycol aqueous solution and 20wt% of maleic anhydride monomer aqueous solution.
5. The method for producing a carboxylic acid surfactant according to claim 2, wherein the heating temperature is 85 ℃; the stirring speed is 150r/min, and the inert gas is nitrogen.
6. The method for producing a carboxylic acid surfactant as claimed in claim 2, wherein the time for the uniform dropwise addition is 4 hours, and the time for the incubation reaction is 3 hours.
7. The method of claim 2, wherein the pH is neutralized to 7 with 40% NaOH solution.
8. A process for producing a carboxylic acid surfactant as claimed in claim 3, wherein the aqueous solution of sodium allylsulfonate is placed in a four-neck flask, and a thermometer, a stirrer, a condenser, a dropping funnel and a nitrogen gas protector are installed, and the temperature is raised to 85 ℃ while stirring, and a solution of a mixture of allylpolyethylene glycol and maleic anhydride monomer is added dropwise while a solution of initiator ammonium persulfate is added dropwise.
9. The use of a carboxylic acid surfactant as claimed in claim 1, wherein said carboxylic acid surfactant is added to a aging oil to remove sand and water.
10. The use of a carboxylic acid surfactant as claimed in claim 8, wherein said carboxylic acid surfactant is added in an amount of 40ppm in the aging oil.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201811123709.5A CN109289695B (en) | 2018-09-26 | 2018-09-26 | Carboxylic acid surfactant and preparation method and application thereof |
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| CN201811123709.5A CN109289695B (en) | 2018-09-26 | 2018-09-26 | Carboxylic acid surfactant and preparation method and application thereof |
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| CN109289695B true CN109289695B (en) | 2020-12-18 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2535702A1 (en) * | 2003-09-22 | 2005-03-31 | The Governors Of The University Of Alberta | Processing aids for enhanced hydrocarbon recovery from oil sands, oil shale and other petroleum residues |
| CN105542093A (en) * | 2016-03-15 | 2016-05-04 | 苏州市兴邦化学建材有限公司 | Synthesis process of polyether type polycarboxylate water reducers with high water reduction property |
| CN107664675A (en) * | 2016-07-29 | 2018-02-06 | 中国石油化工股份有限公司 | Based on thickening type emulsification surfactants washing oil rate analysis method |
| CN107859507A (en) * | 2016-09-22 | 2018-03-30 | 中国石油化工股份有限公司 | Improve the method for increasing of oil well single well productivity |
| CN107177367A (en) * | 2017-05-09 | 2017-09-19 | 常州大学 | Oil-sand cavitation process technique |
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Non-Patent Citations (3)
| Title |
|---|
| 老化油脱水工艺研究;王启华;《中国优秀硕士学位论文全文数据库工程科技I辑》;20130115;全文 * |
| 聚羧酸系减水剂结构模型与高性能化分子设计;李崇智等人;《建筑材料学报》;20040630;第7卷(第3期);第194-195页 * |
| 聚羧酸系高效减水剂的研究进展;周志威等人;《化学建材》;20060720;第22卷(第4期);全文 * |
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