CN-118724721-B - Fuel lubricity improver and preparation method and application thereof

Abstract

A fuel oil lubricity improver and application thereof, wherein the fuel oil lubricity improver comprises a dicarboxylic acid monoether ester compound shown in a structural formula (I), R 1 is a single bond, a substituted or unsubstituted C 1‑18 divalent chain alkyl group or a divalent alkenyl group of C 2‑6 , or a group with a-R 4 -R 5 -R 6 -structure, R 2 is CH 2 、CH 2 CH 2 、CH(CH 3 )CH 2 、CH 2 CH(CH 3 ), n is an integer of 1-12, R 3 is a substituted or unsubstituted C 1‑40 alkyl group, R 4 and R 6 are respectively a single bond or a substituted or unsubstituted C 1‑3 divalent alkyl group, and R 5 is a substituted or unsubstituted C 3‑12 divalent alicyclic group.

Inventors

• LIN JIANMIN
• XIA XIN
• YANG HE
• LI YAN
• LI BAOSHI

Assignees

• 中国石油化工股份有限公司
• 中石化石油化工科学研究院有限公司

Dates

Publication Date

20260505

Application Date

20230329

Claims (10)

1. 1. A fuel composition comprising a fuel and a lubricity improver comprising a dicarboxylic acid monoether ester compound represented by structural formula (I): (I) Wherein R 1 is a single bond, a substituted or unsubstituted C 1-18 divalent chain alkyl group or a divalent alkenyl group of C 2-6 , or a group having a-R 4 -R 5 -R 6 -structure, and R 4 and R 6 are each independently a single bond, a substituted or unsubstituted C 1-3 divalent alkyl group, R 5 is a substituted or unsubstituted C 3-12 divalent alicyclic group, R 2 is a methylene group, an ethylene group, an isopropylidene group, n is an integer of 1 to 3, R 3 is a substituted or unsubstituted C 1-18 hydrocarbon group, and the content of the dicarboxylic acid monoether ester compound is 5 to 400 ppm based on 100% by mass of the fuel oil.
2. 2. The fuel composition according to claim 1, wherein in the structural formula (I), R 1 is a single bond, a substituted or unsubstituted C 2-8 divalent alkylene group or a divalent alkenyl group of C 2-4 , or a group having a-R 4 -R 5 -R 6 -structure, and R 4 and R 6 are each independently a single bond or a methylene group, R 5 is a substituted or unsubstituted divalent alicyclic group of C 3-8 , n is an integer of 1 to 3, and R 3 is a substituted or unsubstituted C 1-12 hydrocarbon group.
3. 3. The fuel composition of claim 1, wherein the dicarboxylic acid mono-alcohol ether ester compound is selected from the group consisting of maleic acid mono-alcohol ether esters, fumaric acid mono-alcohol ether esters, itaconic acid mono-alcohol ether esters, methyl maleic acid mono-alcohol ether esters, methyl fumaric acid mono-alcohol ether esters, 2, 3-dimethyl maleic acid mono-alcohol ether esters, ethyl maleic acid mono-alcohol ether esters, pentenoic acid mono-alcohol ether esters, succinic acid mono-alcohol ether esters, glutaric acid mono-alcohol ether esters, or any combination thereof.
4. 4. The fuel composition of claim 1, wherein the dicarboxylic acid mono-alcohol ether ester compound is selected from the group consisting of 1, 2-cyclohexanedicarboxylic acid mono-alcohol ether esters, tetrahydrophthalic acid mono-alcohol ether esters, phthalic acid mono-alcohol ether esters, methyl hexahydrophthalic acid mono-alcohol ether esters, methyl tetrahydrophthalic acid mono-alcohol ether esters.
5. 5. The fuel composition according to claim 1, wherein the dicarboxylic acid mono-alcohol ether ester compound is one or more selected from the group consisting of mono (ethylene glycol monobutyl ether) maleate, mono (ethylene glycol monoisoamyl ether) maleate, mono (ethylene glycol monoisooctyl ether) maleate, mono (diethylene glycol monobutyl ether) maleate, mono (ethylene glycol monobutyl ether) succinate, mono (ethylene glycol monomethyl ether) succinate, mono (ethylene glycol monoisooctyl ether) succinate, mono (ethylene glycol monomethyl ether) methylhexahydrophthalate, mono (diethylene glycol monomethyl ether) methylhexahydrophthalate, and mono (diethylene glycol monoisooctyl ether) methylhexahydrophthalate.
6. 6. The fuel composition according to claim 1, wherein the content of the dicarboxylic acid monoether ester compound is 10 to 300 ppm based on 100% by mass of the fuel.
7. 7. The fuel composition of claim 1, wherein the fuel is selected from one or more of diesel, gasoline, and aviation fuel.
8. 8. The fuel composition of claim 7, wherein the diesel fuel is selected from low sulfur diesel fuels.
9. 9. The fuel oil composition according to claim 7, wherein the diesel oil is one or more selected from the group consisting of second generation biodiesel, third generation biodiesel, and coal liquefaction diesel oil.
10. 10. Use of a dicarboxylic acid monoether ester compound as a fuel lubricity improver, wherein the dicarboxylic acid monoether ester compound is represented by structural formula (I): (I) Wherein R 1 is a single bond, a substituted or unsubstituted C 1-18 divalent chain alkyl group or a divalent alkenyl group of C 2-6 , or a group having a-R 4 -R 5 -R 6 -structure, and R 4 and R 6 are each independently a single bond, a substituted or unsubstituted C 1-3 divalent alkyl group, R 5 is a substituted or unsubstituted C 3-12 divalent alicyclic group, R 2 is a methylene group, an ethylene group, an isopropylidene group, n is an integer of 1 to 3, and R 3 is a substituted or unsubstituted C 1-18 hydrocarbon group.

Description

Fuel lubricity improver and preparation method and application thereof Technical Field The application relates to the field of fuel additives, in particular to an ester fuel lubricity improver, a preparation method and application thereof. Background Low sulfur diesel and ultra low sulfur diesel are typically treated with lubricity improvers (also known as lubricity additives or antiwear agents) to improve their lubricity due to their poor lubricity. The method has the advantages of low cost, flexible production, less pollution and the like, and is widely valued in industry. The existing low-sulfur diesel antiwear agents used in industry mainly comprise an acid type and an ester type, wherein the main components of the acid type antiwear agents are long-chain unsaturated fatty acids such as oleic acid, linoleic acid, linolenic acid and the like, and typical products are derived from refined tall oil fatty acids. The ester type antiwear agent is the esterification reaction product of the above fatty acid and a polyol. The fatty acid type antiwear agent solves the problem of diesel oil lubricity, but the problems of exceeding diesel oil acidity, increasing corrosiveness risk and the like caused by the large consumption of the diesel oil with the upgrading of the diesel oil emission standard and the deterioration of the lubricity are solved. The fatty acid ester type antiwear agent is used in small amount, but has high cost and the additive diesel oil is emulsified and muddy when meeting water. CN106929112a discloses the use of alkenyl succinic acid monoester as low sulfur diesel antiwear agent, CN113462443a discloses the use of monoester produced by the reaction of unsaturated diacid/anhydride and fatty alcohol or phenol as diesel antiwear agent, CN113462441a discloses the use of cyclic dicarboxylic acid monoester as diesel antiwear agent. The condensation point of the existing diesel antiwear agent is generally as low as about-20 ℃, for example, the condensation point of the fatty acid type antiwear agent is not higher than-12 ℃ and the condensation point of the fatty acid ester type antiwear agent is not higher than-16 ℃ in the used medium petrochemical group antiwear agent standard Q/SHCG-2017. When the antiwear agent with higher solidifying point is used for preparing the ultralow solidifying point diesel oil, additive precipitation can occur under the condition of extremely low temperature, so that the lubricating property of the diesel oil is poor, and the engine filter screen is blocked, so that the oil supply is not smooth. Therefore, the development of low-freezing point antiwear agent products required for ultra-low freezing point diesel oil in alpine regions is also a technical problem to be solved urgently. Gasoline is the lightest, and also the worst lubricity, liquid fuel compared to other fuels. The lubricating effect of the main components of the gasoline is very prominent because of the extremely low content of natural antiwear impurities. Moreover, the new formulation gasoline also contains considerable amounts of oxygen-containing blends (e.g., lower alcohols, etc.) that are readily water-absorbing and readily oxidizable olefins, which can adversely affect the lubricity of the gasoline. The improvement of the lubricity of the gasoline not only means the alleviation of the abrasion of the fuel injection pump and the prolongation of the service life of the engine, but also brings benefits of the improvement of the energy utilization efficiency and the reduction of the fuel consumption rate. Similar to solving the lubricity problems of aviation fuels and diesel oils, an effective method for improving the lubricating properties of gasoline is to add antiwear agents to the gasoline. The prior gasoline antiwear agent mostly uses fatty amine or ether amine as raw materials, the preparation cost is higher, in addition, the prepared lubricity additive is a nitrogen-containing compound, and nitrogen oxides can be generated in the combustion use process of gasoline to cause emission pollution, which is contrary to the use principle of clean fuel. Thus, there remains a significant need in the art for fuel lubricity improvers that are capable of significantly improving fuel lubricity and which are low in cost, low in congeal point, and cleaner to use. Disclosure of Invention The first aspect of the application is to provide a low-freezing-point fuel lubricity improver which not only can remarkably improve the lubricity of fuel, but also has a lower freezing point, does not contain nitrogen, and can be applied to alpine regions. In a second aspect, the present application provides a method of preparing a fuel lubricity improver. A third aspect of the present application is to provide a fuel composition. A fourth aspect of the application is to provide a method of improving lubricity of fuel. In a fifth aspect, the present application provides the use of a dicarboxylic acid monoether ester compound. The s