Lubricity modifier for fuels and application thereof

Patent metadata

Field	Value
Publication number	US-12139679-B2
Application number	US-202117995222-A
Country	US
Kind code	B2
Filing date	Mar 30, 2021
Priority date	Mar 30, 2020
Publication date	Nov 12, 2024
Grant date	Nov 12, 2024

Abstract

A lubricity modifier for fuels contain a dicarboxylic acid monoester compound represented by formula (I). In formula (I), R 1 represents a single bond, a substituted or unsubstituted C 2-6 divalent alkenyl group, or a group having a structure of —R 3 —R 4 —R 5 —; R 2 represents a substituted or unsubstituted C 1-40 hydrocarbyl group; R 3 and R 5 each independently represents a single bond, or a substituted or unsubstituted C 1-3 divalent alkyl group; and R 4 represents a substituted or unsubstituted C 3-12 divalent alicyclic group.

First claim

The invention claimed is:

1. A fuel composition, comprising a fuel component and a lubricity modifier comprising a dicarboxylic acid monoester compound of formula (I):

wherein R 1 represents a unsubstituted C 2-6 divalent alkenyl group or a group of formula —R 3 —R 4 —R 5 —;
R 2 represents a substituted or unsubstituted C 1-40 hydrocarbyl group;
R 3 and R 5 each independently represents a single bond, or a substituted or unsubstituted C 1-3 divalent alkyl group; and
R 4 represents a substituted or unsubstituted C 3-12 divalent alicyclic group,
wherein the term “substituted” means substituted with at least one C 1-4 linear or branched hydrocarbyl group, and
wherein the dicarboxylic acid monoester compound is selected from the group of maleic acid monoester, citraconic acid monoester, glutaconic acid monoester, 1,2-cyclopentanedicarboxylic acid monoester, 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, and combinations thereof.

2. The fuel composition according to claim 1 , wherein R 1 represents the unsubstituted C 2-4 divalent alkenyl group or the group having a structure of —R 3 —R 4 —R 5 —;
R 2 represents a substituted or unsubstituted C 1-18 hydrocarbyl group;
R 3 and R 5 each independently represents a single bond or methylene; and
R 4 represents a substituted or unsubstituted C 3-10 divalent alicyclic group.

3. The fuel composition according to claim 1 , wherein R 2 is selected from the group consisting of C 1-18 linear or branched hydrocarbyl groups, C 4-18 alicyclic hydrocarbyl groups, C 7-18 aryl-substituted hydrocarbyl groups, and C 7-18 hydrocarbyl-substituted aryl groups.

4. The fuel composition according to claim 1 , wherein the dicarboxylic acid monoester compound has a concentration of 5 to 400 ppm, relative to a total mass of the fuel.

5. The fuel composition according to claim 1 , wherein the dicarboxylic acid monoester compound is selected from the group consisting of monomethyl maleate, monoethyl maleate, mono-n-propyl maleate, mono-n-butyl maleate, mono-n-octyl maleate, mono-n-nonyl maleate, mono-n-decyl maleate, mono-n-dodecyl maleate, monoisopropyl maleate, monoisobutyl maleate, mono-sec-butyl maleate, mono-tert-butyl maleate, monoisooctyl maleate (mono-2-ethylhexyl maleate), monoisononyl maleate, monoisodecyl maleate, monoisoundecyl maleate, monoisotridecyl maleate, mono-p-nonylphenyl maleate, monobenzyl maleate, and combinations thereof.

6. The fuel composition according to claim 1 , wherein the dicarboxylic acid monoester compound is selected from the group consisting of 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, and combinations thereof.

7. A method for improving the lubricity of a fuel, comprising the step of adding a lubricity modifier to the fuel, wherein the lubricity modifier comprises a dicarboxylic acid monoester compound of formula (I):

wherein R 1 represents a unsubstituted C 2-6 divalent alkenyl group or a group of formula —R 3 —R 4 —R 5 —;
R 2 represents a substituted or unsubstituted C 1-40 aliphatic hydrocarbyl group;
R 3 and R 5 each independently represents a single bond, or a substituted or unsubstituted C 1-3 divalent alkyl group;
R 4 represents a substituted or unsubstituted C 3-12 divalent alicyclic group,
wherein the term “substituted” means substituted with at least one C 1-4 linear or branched hydrocarbyl group, and wherein the dicarboxylic acid monoester compound is selected from the group of maleic acid monoester, citraconic acid monoester, glutaconic acid monoester, 1,2-cyclopentanedicarboxylic acid monoester, 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, and combinations thereof.

8. The method according to claim 7 , wherein, in dicarboxylic acid monoester compound of formula (I),
R 1 represents the unsubstituted C 2-4 divalent alkenyl group or the group of formula —R 3 —R 4 —R 5 —;
R 2 represents a substituted or unsubstituted C 1-18 saturated aliphatic hydrocarbyl group, alicyclic hydrocarbyl group or aryl group;
R 3 and R 5 each independently represents a single bond or methylene; and
R 4 represents a substituted or unsubstituted C 3-10 divalent alicyclic group.

9. The method according to claim 7 , wherein, in dicarboxylic acid monoester compound of formula (I), R 2 is selected from the group consisting of C 1-18 linear or branched saturated aliphatic hydrocarbyl groups, C 4-18 alicyclic hydrocarbyl groups, C 7-18 aryl-substituted hydrocarbyl groups, and C 7-18 hydrocarbyl-substituted aryl groups.

10. The method according to claim 7 , wherein the dicarboxylic acid monoester compound is selected from the group consisting of monomethyl maleate, monoethyl maleate, mono-n-propyl maleate, mono-n-butyl maleate, mono-n-octyl maleate, mono-n-nonyl maleate, mono-n-decyl maleate, mono-n-dodecyl maleate, monoisopropyl maleate, monoisobutyl maleate, mono-sec-butyl maleate, mono-tert-butyl maleate, monoisooctyl maleate (mono-2-ethylhexyl maleate), monoisononyl maleate, monoisodecyl maleate, monoisoundecyl maleate, monoisotridecyl maleate, monocyclohexyl maleate, mono-p-nonylphenyl maleate, monobenzyl maleate, and combinations thereof.

11. The method according to claim 7 , wherein the dicarboxylic acid monoester compound is selected from the group consisting of 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, and combinations thereof.

12. The method according to claim 7 , wherein the concentration of the dicarboxylic acid monoester compound is 5 to 400 ppm, relative to a total mass of the fuel.

13. A dicarboxylic acid monoester compound of formula (I)

wherein R 1 represents a unsubstituted C 2-6 divalent alkenyl group or a group of formula —R 3 —R 4 —R 5 —;
R 2 represents a substituted or unsubstituted C 5-14 linear or branched alkyl group;
R 3 and R 5 each independently represents a single bond, or a substituted or unsubstituted C 1-3 divalent alkyl group; and
R 4 represents a substituted or unsubstituted C 3-6 divalent alicyclic group,
wherein the term “substituted” means substituted with at least one C 1-4 linear or branched hydrocarbyl group.

14. The dicarboxylic acid monoester compound according to claim 13 , selected from the group consisting of monoisononyl maleate (mono-7-methyl-1-octyl maleate), monoisoundecyl maleate, monoisotridecyl maleate, monoisononyl cyclohexanedicarboxylate, monoisononyl hexahydrophthalate, and monoisononyl methylhexahydrophthalate.

Assignees

• China Petroleum & Chem Corp
• Sinopec Res Inst Petroleum

Inventors

• Lin Jianmin
• Xia Xin
• Li Baoshi
• Li Yan

Classifications

• C10L10/08 Primary

  for improving lubricity; for reducing wear · CPC title

• C10L1/1905

  of di- or polycarboxylic acids · CPC title

• C07C69/60 Primary

  Maleic acid esters; Fumaric acid esters · CPC title

• C10L2270/026

  for diesel engines, e.g. automobiles, stationary, marine · CPC title

• C10L2270/023

  for gasoline engines · CPC title