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CN117701318A - Process for preparing diesel antiwear agent by mixing oleic acid - Google Patents

Process for preparing diesel antiwear agent by mixing oleic acid Download PDF

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Publication number
CN117701318A
CN117701318A CN202311838298.9A CN202311838298A CN117701318A CN 117701318 A CN117701318 A CN 117701318A CN 202311838298 A CN202311838298 A CN 202311838298A CN 117701318 A CN117701318 A CN 117701318A
Authority
CN
China
Prior art keywords
oleic acid
acid
antiwear agent
mixing
diesel
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
CN202311838298.9A
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Chinese (zh)
Inventor
吴中敢
饶宇华
贾海军
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Jiangxi Runda New Material Co ltd
Original Assignee
Jiangxi Runda New Material Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Jiangxi Runda New Material Co ltd filed Critical Jiangxi Runda New Material Co ltd
Priority to CN202311838298.9A priority Critical patent/CN117701318A/en
Publication of CN117701318A publication Critical patent/CN117701318A/en
Pending legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L10/00Use of additives to fuels or fires for particular purposes
    • C10L10/08Use of additives to fuels or fires for particular purposes for improving lubricity; for reducing wear
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • CCHEMISTRY; METALLURGY
    • C10PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10LFUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
    • C10L1/00Liquid carbonaceous fuels
    • C10L1/10Liquid carbonaceous fuels containing additives
    • C10L1/14Organic compounds
    • C10L1/18Organic compounds containing oxygen
    • C10L1/188Carboxylic acids; metal salts thereof

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  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Combustion & Propulsion (AREA)
  • Lubricants (AREA)

Abstract

The invention discloses a process for preparing a diesel antiwear agent by mixing oleic acid, which comprises the steps of heating and refluxing oleic acid, ethanol and phosphoric acid for reaction, wherein the ethanol is used as a reaction solvent and an esterification raw material, the phosphoric acid is used as a catalyst and an esterification raw material, and the prepared mixed oleic acid is a mixture of various substances such as oleic acid, ethyl oleate, oleic acid phosphate and the like, so that the acid value is reduced, and the mixed oleic acid is not easy to emulsify with water.

Description

Process for preparing diesel antiwear agent by mixing oleic acid
Technical Field
The invention relates to the technical field of preparing a diesel antiwear agent from oleic acid, in particular to a process for preparing the diesel antiwear agent from mixed oleic acid.
Background
With the increasing strictness of environmental protection requirements, the diesel oil for vehicles is developed towards high quality and cleanliness, in order to reduce the sulfur content, the diesel oil is hydrofined, and the diesel oil is hydrofined and desulfurized while the lubricity of the diesel oil is reduced, so that the fuel pump in the diesel engine is worn or even damaged. For this reason, the addition of diesel antiwear agents to diesel is a major approach to improving the lubricity of diesel.
In the prior art, the diesel antiwear agent mainly comprises two types of fatty acid type and fatty acid ester type. The fatty acid type diesel antiwear agent is mainly a long-chain unsaturated fatty acid compound, and has the defects of high acid value and corrosion to the metal surface of an engine; the fatty acid ester type antiwear agent has the characteristics of low acid value, low condensation point, good antiwear performance and the like, but has high production cost, easy emulsification when meeting water and long demulsification time, and influences the quality of diesel products.
Disclosure of Invention
The invention discloses a process for preparing a diesel antiwear agent by mixing oleic acid, which adopts oleic acid, ethanol and phosphoric acid to carry out heating reflux reaction, so that the diesel antiwear agent with good lubricating effect and self-demulsification can be prepared.
A process for preparing a diesel antiwear agent by mixing oleic acid comprises the following steps:
(1) Taking a certain amount of oleic acid, adding the oleic acid into a reaction kettle, adding absolute ethyl alcohol with the same molar amount as the oleic acid, adding phosphoric acid with the mass of 1% -3% of the oleic acid, heating to 80-90 ℃ under the protection of nitrogen, carrying out reflux reaction for 2-5 hours, stopping the reaction, distilling the ethanol, and adding a drying agent for dehydration to obtain mixed oleic acid;
(2) Mixing the mixed oleic acid with low freezing point oleic acid, uniformly mixing, and filtering to obtain the diesel antiwear agent.
Further, the end point of the reflux reaction in the step (1) is 1/3 to 1/2 of the original acid value.
Further, the drying agent is anhydrous magnesium sulfate.
Further, in the step (2), oleic acid is mixed, and the mass ratio of the oleic acid with a low freezing point to the oleic acid is 1-2:1.
The invention has the advantages that:
1. according to the invention, through heating reflux reaction of oleic acid, ethanol and phosphoric acid, wherein the ethanol is used as a reaction solvent and an esterification raw material, the phosphoric acid is used as a catalyst and an esterification raw material, and the prepared mixed oleic acid is a mixture of various substances such as oleic acid, ethyl oleate, oleic acid phosphate and the like, so that the acid value is reduced, the mixed oleic acid is not easy to emulsify with water, and the prepared diesel antiwear agent has the advantages of both fatty acid type diesel antiwear agents and fatty acid ester type diesel antiwear agents.
2. Phosphoric acid is added as a catalyst and an esterification raw material to prepare the phosphorylated mixed oleic acid and diesel antiwear agent, which has lower friction coefficient and the function of strengthening engine metal.
Detailed Description
Example 1
A process for preparing a diesel antiwear agent by mixing oleic acid comprises the following steps:
(1) Taking a certain amount of oleic acid, adding the oleic acid into a reaction kettle, adding absolute ethyl alcohol with the same molar amount as the oleic acid, adding phosphoric acid with the mass of 1.2% of the oleic acid, heating to 85 ℃ under the protection of nitrogen, carrying out reflux reaction until the acid value is reduced to 1/2 of the original acid value, stopping the reaction, distilling the ethanol, and then adding anhydrous magnesium sulfate for dehydration to obtain mixed oleic acid;
(2) Mixing the mixed oleic acid with low-freezing-point oleic acid, wherein the mass ratio of the mixed oleic acid to the low-freezing-point oleic acid is 1.5:1, uniformly mixing, and filtering to obtain the diesel antiwear agent.
Comparative example 1
Low freezing point oleic acid is used as the diesel antiwear agent.
Comparative example 2
Ethyl oleate is used as a diesel antiwear agent.
And (3) testing:
the diesel antiwear agent of the above examples and comparative examples was added to diesel oil at a ratio of 200mg/kg, and compared with diesel oil without the diesel antiwear agent, and the diesel oil was coated on a steel plate, and friction weight reduction experiments were performed under a pressure of 10kg, and after 10 ten thousand times of friction, weight reduction was obtained.
10% by mass of water was added to the diesel oil, homogenized and emulsified, and the layering time was observed.
Friction weight loss test Example 1 Comparative example 1 Comparative example 2 Diesel oil
Weight reduction (mg) 129 205 161 512
Layering time(s) 295 287 1223 209
Compared with pure oleic acid, the acid value of the diesel antiwear agent prepared by the invention is reduced by 30% -40%, and the corrosion to metal can be effectively reduced; and after being added into diesel oil, the water-emulsified diesel oil is basically consistent with the layering time after being emulsified by water.
Finally: the foregoing description of the preferred embodiments of the invention is not intended to limit the invention to the precise form disclosed, and any such modifications, equivalents, and alternatives falling within the spirit and principles of the invention are intended to be included within the scope of the invention.

Claims (4)

1.一种混合油酸制备柴油抗磨剂的工艺,其特征在于:所述工艺具体如下:1. A process for preparing diesel antiwear agent by mixing oleic acid, which is characterized in that: the process is as follows: (1)取一定量的油酸,加入反应釜,然后加入与油酸等摩尔量的无水乙醇,然后加入油酸质量1%-3%的磷酸,在氮气保护下加热至80℃-90℃,回流反应2h-5h后,停止反应,蒸馏出乙醇,然后加入干燥剂脱水,制得混合油酸;(1) Take a certain amount of oleic acid, add it to the reaction kettle, then add anhydrous ethanol in an equal molar amount to the oleic acid, then add 1%-3% phosphoric acid by mass of oleic acid, and heat to 80°C-90°C under nitrogen protection ℃, after 2h-5h of reflux reaction, stop the reaction, distill out the ethanol, and then add a desiccant for dehydration to prepare mixed oleic acid; (2)取上述混合油酸,与低冻点油酸混合,混合均匀后过滤,制得柴油抗磨剂。(2) Take the above mixed oleic acid, mix it with low freezing point oleic acid, mix it evenly and then filter it to prepare a diesel anti-wear agent. 2.根据权利要求1所述混合油酸制备柴油抗磨剂的工艺,其特征在于:第(1)步回流反应的终点为酸值降低至原酸值的1/3-1/2。2. The process for preparing diesel antiwear agent by mixing oleic acid according to claim 1, characterized in that: the end point of the reflux reaction in step (1) is when the acid value is reduced to 1/3-1/2 of the original acid value. 3.根据权利要求1所述混合油酸制备柴油抗磨剂的工艺,其特征在于:所述干燥剂为无水硫酸镁。3. The process for preparing diesel anti-wear agent by mixing oleic acid according to claim 1, characterized in that: the desiccant is anhydrous magnesium sulfate. 4.根据权利要求1所述混合油酸制备柴油抗磨剂的工艺,其特征在于:第(2)步混合油酸:低冻点油酸质量比为1-2:1。4. The process for preparing diesel antiwear agent by mixing oleic acid according to claim 1, characterized in that: the mass ratio of mixing oleic acid in step (2): low freezing point oleic acid is 1-2:1.
CN202311838298.9A 2023-12-28 2023-12-28 Process for preparing diesel antiwear agent by mixing oleic acid Pending CN117701318A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202311838298.9A CN117701318A (en) 2023-12-28 2023-12-28 Process for preparing diesel antiwear agent by mixing oleic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202311838298.9A CN117701318A (en) 2023-12-28 2023-12-28 Process for preparing diesel antiwear agent by mixing oleic acid

Publications (1)

Publication Number Publication Date
CN117701318A true CN117701318A (en) 2024-03-15

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Family Applications (1)

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Country Status (1)

Country Link
CN (1) CN117701318A (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986006371A1 (en) * 1985-04-25 1986-11-06 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates, lubricating oils, and metal working lubricants containing same
WO2006081644A2 (en) * 2005-02-02 2006-08-10 Universidade Federal Do Rio De Janeiro-Ufrj Catalytic process for the esterification of fatty acids
CN113462442A (en) * 2020-03-30 2021-10-01 中国石油化工股份有限公司 Diesel antiwear agent composition, preparation method thereof and diesel composition

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1986006371A1 (en) * 1985-04-25 1986-11-06 The Lubrizol Corporation Sulfur-containing compositions, and additive concentrates, lubricating oils, and metal working lubricants containing same
WO2006081644A2 (en) * 2005-02-02 2006-08-10 Universidade Federal Do Rio De Janeiro-Ufrj Catalytic process for the esterification of fatty acids
CN113462442A (en) * 2020-03-30 2021-10-01 中国石油化工股份有限公司 Diesel antiwear agent composition, preparation method thereof and diesel composition

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
颜志光: "《润滑材料与润滑技术》", 31 January 2000, 中国石化出版社, pages: 60 *

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