CN116410704A - Antiwear synergist and preparation method thereof, lubricant composition and application - Google Patents
Antiwear synergist and preparation method thereof, lubricant composition and application Download PDFInfo
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- CN116410704A CN116410704A CN202111649677.4A CN202111649677A CN116410704A CN 116410704 A CN116410704 A CN 116410704A CN 202111649677 A CN202111649677 A CN 202111649677A CN 116410704 A CN116410704 A CN 116410704A
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- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000000314 lubricant Substances 0.000 title claims description 53
- 239000000203 mixture Substances 0.000 title claims description 12
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229940106681 chloroacetic acid Drugs 0.000 claims abstract description 18
- -1 nitrogenous heterocyclic compound Chemical class 0.000 claims abstract description 11
- 238000005553 drilling Methods 0.000 claims description 53
- 239000012530 fluid Substances 0.000 claims description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 24
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 16
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 12
- 239000008158 vegetable oil Substances 0.000 claims description 12
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 10
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- NQXWGWZJXJUMQB-UHFFFAOYSA-K iron trichloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].Cl[Fe+]Cl NQXWGWZJXJUMQB-UHFFFAOYSA-K 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 8
- 229940044631 ferric chloride hexahydrate Drugs 0.000 claims description 7
- 239000003995 emulsifying agent Substances 0.000 claims description 6
- 238000005886 esterification reaction Methods 0.000 claims description 6
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 claims description 5
- 239000003921 oil Substances 0.000 claims description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 239000002199 base oil Substances 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 235000019198 oils Nutrition 0.000 claims description 4
- 230000035484 reaction time Effects 0.000 claims description 4
- 235000010446 mineral oil Nutrition 0.000 claims description 3
- 239000002480 mineral oil Substances 0.000 claims description 3
- 229920001214 Polysorbate 60 Polymers 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052751 metal Inorganic materials 0.000 abstract description 7
- 239000002184 metal Substances 0.000 abstract description 7
- 238000001179 sorption measurement Methods 0.000 abstract description 7
- 125000004429 atom Chemical group 0.000 abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 239000002002 slurry Substances 0.000 description 24
- 238000001914 filtration Methods 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 15
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 238000001035 drying Methods 0.000 description 10
- 238000005461 lubrication Methods 0.000 description 10
- 239000012074 organic phase Substances 0.000 description 10
- 238000002390 rotary evaporation Methods 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- 238000010992 reflux Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 230000001050 lubricating effect Effects 0.000 description 7
- 150000002391 heterocyclic compounds Chemical class 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- MQRJBSHKWOFOGF-UHFFFAOYSA-L disodium;carbonate;hydrate Chemical compound O.[Na+].[Na+].[O-]C([O-])=O MQRJBSHKWOFOGF-UHFFFAOYSA-L 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000012467 final product Substances 0.000 description 5
- 239000008213 purified water Substances 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000012847 fine chemical Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000015784 hyperosmotic salinity response Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
Classifications
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- 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
- C09K8/00—Compositions for drilling of boreholes or wells; Compositions for treating boreholes or wells, e.g. for completion or for remedial operations
- C09K8/02—Well-drilling compositions
- C09K8/03—Specific additives for general use in well-drilling compositions
- C09K8/035—Organic additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/28—Friction or drag reducing additives
-
- 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
- C09K2208/00—Aspects relating to compositions of drilling or well treatment fluids
- C09K2208/34—Lubricant additives
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Lubricants (AREA)
Abstract
The invention provides an antiwear synergist, a preparation method and application thereof, wherein the antiwear synergist is prepared by reacting chloroacetic acid, 1, 4-butanediol and a nitrogenous heterocyclic compound as raw materials, and the antiwear synergist can form a stable surface adsorption film with metal surface atoms based on nitrogen atoms in the nitrogenous heterocyclic compound structure.
Description
Technical Field
The invention relates to the technical field of oilfield drilling fluid, in particular to an antiwear synergist and a preparation method and application thereof.
Background
The lubricant is one of core treatment agents of drilling fluid, can obviously reduce friction between a drilling tool and a well wall, reduce drilling torque and tripping friction, can effectively improve drilling speed and greatly improve working efficiency. With the development of oil and gas exploration, horizontal wells, directional wells, long open hole deep wells and complex structure wells are adopted in drilling engineering, the contact area between a drill column and a well wall is obviously increased during operation, and friction resistance is increased, so that the modern drilling operation has higher requirements on extreme pressure wear resistance and lubricating performance of water-based drilling fluid. At present, most of conventional lubricants used on site are mineral oil or white oil, vegetable oil and synthetic lipid which are the best in biodegradability and the worst in biodegradability, and are easy to pollute the ecological environment. Vegetable oil lubricants are relatively environmentally friendly and have good lubricating effects at normal temperature, but have relatively poor temperature resistance and salt tolerance, and the extreme pressure antiwear properties of vegetable oil and synthetic lipid lubricants need to be improved.
In the underground drilling environment with high speed, high temperature, high load and other severe working conditions, the antiwear synergist is an important component of water-base drilling fluid lubricant. The existing extreme pressure antiwear agent is mainly of the S type, the P type, the Cl type, the Mo type, the N type, the B type, the organic metal type, the rare earth compound type and the nanoparticle type, wherein the S type, the P type and the Cl type extreme pressure antiwear agent belong to the traditional type, mainly react with metal to generate a compound film, can be used in a compounding way, has a certain synergistic effect, but has poor environmental protection. Mo type, N type, B type belong to novel environment-friendly extreme pressure antiwear agent, which can generate chemical adsorption film on metal surface in chemical bond form, but is used less in drilling fluid lubricant at present, and can be used as key research direction for improving water-based drilling fluid antiwear and drag reduction performance.
With the development of petroleum engineering and the improvement of energy green and efficient development requirements, the performance requirements on the water-based drilling fluid lubricant are also higher and higher. Therefore, a treating agent which has excellent performance and is environment-friendly and can improve the wear resistance and drag reduction performance of the water-based drilling fluid is developed, and the treating agent has important practical significance for accelerating the efficient and green development of oil gas in China.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides an antiwear synergist and a preparation method and application thereof.
In a first aspect, the present invention provides an antiwear synergist having the structural formula:
in the formula 1, R is
The antiwear synergist is based on the fact that N atoms in the structure of the nitrogen-containing heterocyclic compounds can form stable coordination bonds with Fe atoms on the metal surface, the nitrogen-containing heterocyclic compounds are adsorbed on the steel surface in a chemical bond mode, and a stable adsorption film is formed on the steel surface, so that the antiwear and drag reduction performance of the antiwear agent can be effectively improved.
In a second aspect, the invention provides a method for preparing an antiwear synergist, comprising the following steps:
s1: taking ferric chloride hexahydrate as a catalyst, and carrying out esterification reaction on butanediol and chloroacetic acid to obtain an intermediate;
s2: and (2) taking sodium bicarbonate as an alkaline catalyst, and reacting the intermediate obtained in the step (S1) with a nitrogenous heterocyclic compound to obtain the antiwear synergist.
In the step S1, the molar ratio of the butanediol to the chloroacetic acid is 1:2-4, preferably 1:2.2.
In the step S1, the esterification reaction temperature is 70 to 90 ℃; the esterification reaction time is 8-12 h.
In a specific embodiment of the present invention, in the step S1, the intermediate has a structural formula:
as a specific embodiment of the present invention, in the step S2, the nitrogen-containing heterocyclic compound is piperazine and a derivative thereof; the piperazine and its derivatives are preferably piperazine, N-methylpiperazine.
The molar ratio of the intermediate to the nitrogen-containing heterocyclic compound is 1:1-3, preferably 1:1.4.
In the step S2, the reaction temperature is 60 to 80 ℃; the reaction time is 4-8 h.
As a specific embodiment of the present invention, the reactions in step S1 and step S2 are performed in the presence of a solvent; preferably, the solvents are each independently selected from cyclohexane and tetrahydrofuran.
In a third aspect, the present invention provides a lubricant composition comprising 6 to 11% antiwear agent, 85 to 90% base oil, 4 to 9% emulsifier.
As a specific embodiment of the present invention, the base oil is at least one of mineral oil, vegetable oil, and synthetic oil.
As a specific embodiment of the invention, the emulsifier is at least one of span 80, OP-10 and Tween 60.
In a fourth aspect, the invention provides the use of a lubricant comprising the antiwear package in a water-based drilling fluid.
As a specific embodiment of the present invention, the lubricant composition has a mass fraction of 1.0% to 3.0% in the water-based drilling fluid.
The above-mentioned raw materials in the present invention are all self-made or commercially available, and the present invention is not particularly limited thereto.
Compared with the prior art, the invention has the beneficial effects that:
1. the antiwear synergist is a nitrogenous treatment agent prepared by taking chloroacetic acid, 1, 4-butanediol and nitrogenous heterocyclic compounds as raw materials to react, and the antiwear synergist can form a stable surface adsorption film with metal surface atoms based on nitrogen atoms in the nitrogenous heterocyclic compound structure, and the chemical adsorption film can effectively improve the antiwear and drag reduction performances of the antiwear agent. The antiwear agent disclosed by the invention is added into a water-based drilling fluid lubricant, so that the antiwear and drag reduction performances of the water-based drilling fluid lubricant can be obviously improved.
2. According to the embodiment of the invention, the lubricant containing the antiwear synergist is used for the water-based drilling fluid, so that the friction resistance of the drilling fluid can be obviously reduced, and the reduction rate of the lubrication coefficient can reach more than 80%.
3. The antiwear synergist can obviously improve the antiwear and drag reduction effects of the lubricant with lower addition, and the preparation method is simple, can be widely applied and has good market prospect.
Detailed Description
The invention is further illustrated below in connection with specific examples, which are not to be construed as limiting the invention in any way.
In the various embodiments of the invention, the reagents used were:
chloroacetic acid, chemically pure, manufacturer is the company of Miou chemical reagent, inc. of Tianjin;
1, 4-butanediol, analytically pure, manufacturer is Tianjin, denko Europe chemical reagent Co., ltd;
ferric trichloride hexahydrate, analytically pure, manufacturer is available from Tianjin, denko chemical industries, ltd;
cyclohexane, chemically pure, manufacturer is the company of Miou chemical reagent, inc. of Tianjin;
sodium carbonate, chemically pure, manufacturer is the company of Tianjin chemical reagent Co., ltd;
sodium chloride, chemically pure, manufacturer is the company of Miou chemical reagent, inc. of Tianjin;
dichloromethane, chemical purity, manufacturer is MIEuro chemical reagent Co., ltd;
piperazine, industrial grade, manufacturer is Tianjin city fine chemical industry limited company;
tetrahydrofuran, chemically pure, manufacturer is Miou chemical reagent Co., ltd;
n-methylpiperazine, industrial grade, manufacturer is the new chemical industry Co., ltd;
cottonseed oil, industrial grade, manufacturer is Jinan Boao chemical Co., ltd;
span 80, industrial grade, manufacturer is Shandong polymer chemical Co.
Example 1
The invention provides an antiwear synergist and a preparation method thereof, and the specific details are as follows:
s1: 42g of chloroacetic acid, 18g of 1, 4-butanediol and 3.6g of ferric chloride hexahydrate are sequentially added into a three-necked flask, cyclohexane is used as a solvent, reflux reaction is carried out for 10 hours at 80 ℃, and water in a water separator reaches a theoretical value, so that the reaction is stopped. Cooling to room temperature, removing solvent by rotary evaporation, washing with sodium carbonate water solution and saturated saline water for three times, extracting with dichloromethane, drying organic phase, and filtering to obtain intermediate.
S2: 29g of the intermediate obtained in the step S1 and 24g of piperazine are added into a three-necked flask, tetrahydrofuran is used as a solvent, and reflux reaction is carried out for 4 hours at 70 ℃. After the reaction is finished, filtering, removing the solvent by rotary evaporation, washing with saturated saline water for three times, extracting with dichloromethane, drying an organic phase, and filtering to obtain the final product of the antiwear synergist.
The antiwear synergist obtained in example 1 has the structural formula:
example 2
The invention provides an antiwear synergist and a preparation method thereof, and the specific details are as follows:
s1: 42g of chloroacetic acid, 18g of 1, 4-butanediol and 3.6g of ferric chloride hexahydrate are sequentially added into a three-necked flask, cyclohexane is used as a solvent, reflux reaction is carried out for 10 hours at 80 ℃, and water in a water separator reaches a theoretical value, so that the reaction is stopped. Cooling to room temperature, removing solvent by rotary evaporation, washing with sodium carbonate water solution and saturated saline water for three times, extracting with dichloromethane, drying organic phase, and filtering to obtain intermediate.
S2: 29g of the intermediate obtained in the step S1 and 28g of N-methylpiperazine are added into a three-necked flask, tetrahydrofuran is used as a solvent, and reflux reaction is carried out for 4 hours at 70 ℃. After the reaction is finished, filtering, removing the solvent by rotary evaporation, washing with saturated saline water for three times, extracting with dichloromethane, drying an organic phase, and filtering to obtain a final product, namely the grinding synergist.
The antiwear synergist obtained in example 2 has the structural formula:
example 3
The invention provides an antiwear synergist and a preparation method thereof, and the specific details are as follows:
s1: 57g of chloroacetic acid, 18g of 1, 4-butanediol and 3.6g of ferric chloride hexahydrate are sequentially added into a three-necked flask, cyclohexane is used as a solvent, reflux reaction is carried out for 10 hours at 80 ℃, and water in a water separator reaches a theoretical value, so that the reaction is stopped. Cooling to room temperature, removing solvent by rotary evaporation, washing with sodium carbonate water solution and saturated saline water for three times, extracting with dichloromethane, drying organic phase, and filtering to obtain intermediate.
S2: 29g of the intermediate obtained in the step S1 and 24g of piperazine are added into a three-necked flask, tetrahydrofuran is used as a solvent, and reflux reaction is carried out for 4 hours at 70 ℃. After the reaction is finished, filtering, removing the solvent by rotary evaporation, washing with saturated saline water for three times, extracting with dichloromethane, drying an organic phase, and filtering to obtain the final product of the antiwear synergist.
The antiwear synergist obtained in example 3 has the structural formula:
example 4
The invention provides an antiwear synergist and a preparation method thereof, and the specific details are as follows:
s1: 57g of chloroacetic acid, 18g of 1, 4-butanediol and 3.6g of ferric chloride hexahydrate are sequentially added into a three-necked flask, cyclohexane is used as a solvent, reflux reaction is carried out for 10 hours at 80 ℃, and water in a water separator reaches a theoretical value, so that the reaction is stopped. Cooling to room temperature, removing solvent by rotary evaporation, washing with sodium carbonate water solution and saturated saline water for three times, extracting with dichloromethane, drying organic phase, and filtering to obtain intermediate.
S2: 29g of the intermediate obtained in the step S1 and 39g of N-methylpiperazine were added to a three-necked flask, and the mixture was refluxed at 70℃for 4 hours with tetrahydrofuran as a solvent. After the reaction is finished, filtering, removing the solvent by rotary evaporation, washing with saturated saline water for three times, extracting with dichloromethane, drying an organic phase, and filtering to obtain the final product of the antiwear synergist.
The antiwear synergist obtained in example 4 has the structural formula:
example 5
The invention provides an antiwear synergist and a preparation method thereof, and the specific details are as follows:
s1: 42g of chloroacetic acid, 18g of 1, 4-butanediol and 3.6g of ferric chloride hexahydrate are sequentially added into a three-necked flask, cyclohexane is used as a solvent, reflux reaction is carried out for 10 hours at 80 ℃, and water in a water separator reaches a theoretical value, so that the reaction is stopped. Cooling to room temperature, removing solvent by rotary evaporation, washing with sodium carbonate water solution and saturated saline water for three times, extracting with dichloromethane, drying organic phase, and filtering to obtain intermediate.
S2: 29g of the intermediate obtained in the step S1 and 39g of N-methylpiperazine were added to a three-necked flask, and the mixture was refluxed at 70℃for 4 hours with tetrahydrofuran as a solvent. After the reaction is finished, filtering, removing the solvent by rotary evaporation, washing with saturated saline water for three times, extracting with dichloromethane, drying an organic phase, and filtering to obtain the final product of the antiwear synergist.
The antiwear synergist obtained in example 5 has the structural formula:
example 6
The antiwear synergist prepared in examples 1-5 was combined into drilling fluid lubricant according to the following lubricant formulation ratio to obtain water-based drilling fluid lubricant 1-5.
The lubricant comprises the following components: 89% of vegetable oil, 6% of antiwear drag reducing additive and 5% of span 80 emulsifier.
Example 7
The antiwear synergist prepared in examples 1-5 is compounded into drilling fluid lubricant in certain proportion to obtain water base drilling fluid lubricant 6-10.
The lubricant comprises the following components: 85% of vegetable oil, 10% of antiwear drag reducing additive and 5% of span 80 emulsifier.
Test example 1
Evaluation of performance: the 10 water-based drilling fluid lubricants prepared in examples 6 and 7 were tested for rheological properties, fluid loss, and coefficient of lubrication in drilling fluids.
Rheological properties and fluid loss of drilling fluids according to GB/T16783.1-2014 "petroleum and gas industry drilling fluid field test part 1: water-based drilling fluid "measurements".
Drilling fluid lubricating properties were tested using a Fann extreme pressure lubricator. The operation steps are as follows: the lubrication instrument is checked by purified water, the torque handle is adjusted to 150 inch-points to run for 5min under the rotating speed condition of 60rpm, and the reading of the purified water is tested to be between 28 and 42. And (3) replacing purified water with the slurry to be measured, and measuring the lubrication coefficient of the slurry to be measured. The machine was checked with purified water before each test.
The lubrication coefficient calculation formula: (slurry to be measured reading/100) × (34/purified water reading)
In the above test, the test samples were drilling fluid base slurry (A0), sample slurries (A1 to a 10) in which the lubricants 1 to 10 prepared in examples 6 and 7 were mixed with the base slurry, and comparative sample slurry (B1) in which the vegetable oil type lubricants were mixed with the base slurry.
The preparation method of the drilling fluid base slurry comprises the following steps: 5% of the slurry is prepared by hydration of bentonite, 0.3% of anhydrous sodium carbonate and the balance of water for 24 hours at room temperature.
The test results are shown in table 1:
table 1 test data comparison of drilling fluid base slurry (A0), sample slurries (A1 to a 10) obtained by mixing lubricants 1 to 10 prepared in examples 5 and 6 with the base slurry, and comparative sample slurry (B1) obtained by mixing vegetable oil type lubricant with the base slurry
As can be seen from the data in Table 1, the lubrication coefficients of the drilling fluids to be tested are all 0.029-0.048 at normal temperature, which shows that the drilling fluids have good lubrication performance and can effectively reduce friction and torque of drilling construction, wherein the lubrication coefficient of the drilling fluid prepared by the lubricant added with the antiwear synergist is obviously lower than that of the drilling fluid prepared by the lubricant without the additive. Meanwhile, the API filtration loss of the drilling fluid with the lubricant is obviously reduced, and the rheological property of the drilling fluid is not obviously influenced.
The drilling fluid base slurry and the sample slurry added with the lubricant of the embodiment are aged for 16 hours at 140 ℃ in a roller heating furnace, and the rheological property, the filtration loss and the lubrication coefficient of the drilling fluid base slurry and the sample slurry are tested. The test results are shown in table 2:
table 2 test data comparison after aging of drilling fluid base slurry (A0), sample slurries (A1 to a 10) obtained by mixing lubricants 1 to 10 prepared in examples 6 and 7 with the base slurry, and comparative sample slurry (B1) obtained by mixing vegetable oil type lubricant with the base slurry
As can be seen from the data in Table 2, the lubricating coefficient of the drilling fluid prepared by the lubricant added with the treating agent in the invention after high-temperature aging at 140 ℃ is still kept between 0.036 and 0.057, and the API fluid loss is kept low. However, the lubricating coefficient of the drilling fluid added with the conventional vegetable oil type lubricant reaches 0.097, and the API fluid loss is obviously increased. The invention shows that the antiwear synergist has good heat resistance, can still ensure that the lubricant maintains excellent lubrication friction reduction performance after being aged at a high temperature of 140 ℃, and can effectively improve the antiwear and drag reduction performance of the water-based drilling fluid lubricant.
The effect of the lubricants 6-10 prepared by the formula of the example 7 is better than that of the lubricants 1-5 prepared by the formula of the example 6, the effect is obviously better than that of the vegetable oil type lubricant B1 without the antiwear synergist, and the antiwear synergist in the lubricant is helpful for improving the extreme pressure and antiwear performance of the lubricant.
In example 1, the molar ratio of butanediol to chloroacetic acid is 1:2.2, piperazine is used in the second reaction step, and the molar ratio of the intermediate to the heterocyclic compound is 1:1.4; in example 2, the molar ratio of butanediol to chloroacetic acid was 1:2.2, and in the second step N-methylpiperazine was used, the molar ratio of intermediate to heterocyclic compound was 1:1.4; in example 3, the molar ratio of butanediol to chloroacetic acid was 1:3, piperazine was used in the second reaction step, and the molar ratio of intermediate to heterocyclic compound was 1:1.4; in example 4, the molar ratio of butanediol to chloroacetic acid was 1:3, and in the second step N-methylpiperazine was used, the molar ratio of intermediate to heterocyclic compound was 1:2; in example 5, the molar ratio of butanediol to chloroacetic acid was 1:2.2, and in the second step N-methylpiperazine was used, the molar ratio of intermediate to heterocyclic compound was 1:2. As can be seen from the test example data, the molar ratio of butanediol to chloroacetic acid is optimally 1:2.2, and the molar ratio of the intermediate to the heterocyclic compound is optimally 1:1.4. Therefore, the antiwear synergist obtained in the examples 1 and 2 has the optimal effect, the lubricant composed of the antiwear synergist synthesized according to the formula proportion of the examples 1 and 2 has the optimal application effect in the water-based drilling fluid, and the performance of A6 and A7 is better than that of A1 and A2, so that the antiwear synergist can effectively improve the lubricating performance of the lubricant after high-temperature aging.
In summary, the antiwear synergist is a nitrogenous treatment agent, and the antiwear synergist can form a stable surface adsorption film with metal surface atoms based on nitrogen atoms in a nitrogenous heterocyclic compound structure, and the chemical adsorption film can effectively improve the antiwear and drag reduction performance of the antiwear agent. The antiwear agent disclosed by the invention is added into a water-based drilling fluid lubricant, so that the antiwear and drag reduction performances of the water-based drilling fluid lubricant can be obviously improved. The lubricant containing the antiwear synergist is used in water-base drilling fluid, so that the friction resistance of the drilling fluid can be obviously reduced, and the reduction rate of the lubricating coefficient can reach more than 80%.
Any numerical value recited in this disclosure includes all values incremented by one unit from the lowest value to the highest value if there is only a two unit interval between any lowest value and any highest value. For example, if the amount of one component, or the value of a process variable such as temperature, pressure, time, etc., is stated to be 50-90, it is meant in this specification that values such as 51-89, 52-88 … …, and 69-71, and 70-71 are specifically recited. For non-integer values, 0.1, 0.01, 0.001 or 0.0001 units may be considered as appropriate. This is only a few examples of the specific designations. In a similar manner, all possible combinations of numerical values between the lowest value and the highest value enumerated are to be considered to be disclosed in this application.
It should be noted that the above-described embodiments are only for explaining the present invention and do not constitute any limitation of the present invention. The invention has been described with reference to exemplary embodiments, but it is understood that the words which have been used are words of description and illustration, rather than words of limitation. Modifications may be made to the invention as defined in the appended claims, and the invention may be modified without departing from the scope and spirit of the invention. Although the invention is described herein with reference to particular means, materials and embodiments, the invention is not intended to be limited to the particulars disclosed herein, as the invention extends to all other means and applications which perform the same function.
Claims (13)
1. The antiwear synergist is characterized by having the structural formula:
in the formula 1, R is
2. The method for preparing the antiwear synergist as defined in claim 1, comprising the following steps:
s1: taking ferric chloride hexahydrate as a catalyst, and carrying out esterification reaction on butanediol and chloroacetic acid to obtain an intermediate;
s2: and (2) taking sodium bicarbonate as an alkaline catalyst, and reacting the intermediate obtained in the step (S1) with a nitrogenous heterocyclic compound to obtain the antiwear synergist.
3. The method according to claim 2, wherein in step S1, the molar ratio of butanediol to chloroacetic acid is 1:2-4, preferably 1:2.2.
4. The method according to claim 2 or 3, wherein in the step S1, the esterification reaction temperature is 70 to 90 ℃; the esterification reaction time is 8-12 h.
5. The method according to any one of claims 2 to 4, wherein in the step S1, the intermediate has a structural formula:
6. the method according to any one of claims 2 to 5, wherein in step S2, the nitrogen-containing heterocyclic compound is piperazine or a derivative thereof; the piperazine and its derivatives are preferably piperazine, N-methylpiperazine; and/or
The molar ratio of the intermediate to the nitrogen-containing heterocyclic compound is 1:1-3, preferably 1:1.4.
7. The method according to any one of claims 2 to 6, wherein in step S2, the reaction temperature is 60 to 80 ℃; the reaction time is 4-8 h.
8. The preparation method according to any one of claims 2 to 7, wherein the reactions in step S1 and step S2 are carried out in the presence of a solvent; preferably, the solvents are each independently selected from cyclohexane and tetrahydrofuran.
9. A lubricant composition comprising 6 to 11 mass percent of the antiwear synergist of claim 1 or the antiwear synergist prepared by the preparation method of any one of claims 2 to 8, 85 to 90 mass percent of base oil, and 4 to 9 mass percent of emulsifier.
10. The lubricant composition of claim 9, wherein the base oil is at least one of a mineral oil, a vegetable oil, and a synthetic oil.
11. The lubricant composition according to claim 9 or 10, wherein the emulsifier is at least one of span 80, OP-10, tween 60.
12. Use of the antiwear potentiator of claim 1, the antiwear potentiator prepared by the method of any one of claims 2 to 8 or the lubricant composition of any one of claims 9 to 11 in a water-based drilling fluid.
13. The use according to claim 12, wherein the lubricant composition is present in the drilling fluid in a mass fraction of 1.0% to 3.0%.
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| CN117986243A (en) * | 2024-04-03 | 2024-05-07 | 湖南浩润科技有限公司 | Diesel antiwear agent containing heterocyclic compound and preparation method thereof |
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| CN107417555A (en) * | 2017-06-06 | 2017-12-01 | 东莞理工学院 | A kind of butanediol two (2 glycine) ester derivative lube oil additive and preparation method thereof |
| CN109504354A (en) * | 2019-01-14 | 2019-03-22 | 中海石油(中国)有限公司上海分公司 | A kind of lubricant, drilling fluid and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107417555A (en) * | 2017-06-06 | 2017-12-01 | 东莞理工学院 | A kind of butanediol two (2 glycine) ester derivative lube oil additive and preparation method thereof |
| CN109504354A (en) * | 2019-01-14 | 2019-03-22 | 中海石油(中国)有限公司上海分公司 | A kind of lubricant, drilling fluid and its application |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN117986243A (en) * | 2024-04-03 | 2024-05-07 | 湖南浩润科技有限公司 | Diesel antiwear agent containing heterocyclic compound and preparation method thereof |
| CN117986243B (en) * | 2024-04-03 | 2024-05-31 | 湖南浩润科技有限公司 | Diesel antiwear agent containing heterocyclic compound and preparation method thereof |
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