Lubricity modifier for fuels and application thereof

Patent metadata

Field	Value
Publication number	US-2023151290-A1
Application number	US-202117995222-A
Country	US
Kind code	A1
Filing date	Mar 30, 2021
Priority date	Mar 30, 2020
Publication date	May 18, 2023
Grant date	—

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

1 . A lubricity modifier for fuels, comprising a dicarboxylic acid monoester compound represented by the formula (I):

wherein 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;
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.

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

3 . The lubricity modifier 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, and C 7-18 aryl-substituted hydrocarbyl groups or hydrocarbyl-substituted aryl groups.

4 . The lubricity modifier according to claim 1 , wherein
the dicarboxylic acid monoester compound is selected from the group of maleic acid monoester, fumaric acid monoester, itaconic acid monoester, citraconic acid monoester, methyl fumaric acid monoester, 2,3-dimethyl maleic acid monoester, glutaconic acid monoester, or any combination thereof.

5 . The lubricity modifier according to claim 1 , wherein
the dicarboxylic acid monoester compound is selected from the group consisting of 1,2-cyclopentanedicarboxylic acid monoester, 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, methylhexahydrophthalic acid monoester, methyltetrahydrophthalic acid monoester, 1-methyl-1,2-cyclohexanedicarboxylic acid monoester, 4-methyl-1,2-cyclohexanedicarboxylic acid monoester, 3-methyl-1,2-cyclohexanedicarboxylic acid monoester, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid monoester, 3-methyl-4-cyclohexene-1,2-dicarboxylic acid monoester, or any combination thereof.

6 . A fuel composition, comprising a fuel component and the lubricity modifier according to claim 1 , wherein the dicarboxylic acid monoester compound is present at an amount of 5 to 400 ppm, relative to the mass of the fuel as 100%.

7 . A method for improving the lubricity of a fuel, comprising the step of adding the lubricity modifier according to claim 1 to the fuel, wherein the dicarboxylic acid monoester compound is used in an amount of 5 to 400 ppm, relative to the mass of the fuel as 100%.

8 - 9 . (canceled)

10 . A dicarboxylic acid monoester compound of formula (I) suitable for use as a lubricity modifier for fuels:

wherein R 1 represents 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 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;
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.

11 . The dicarboxylic acid monoester compound according to claim 10 , selected from the group consisting of: monoisononyl maleate (mono-7-methyl-1-octyl maleate), monoisoundecyl maleate, monoisotridecyl maleate, monoisoamyl itaconate, monoisononyl itaconate (mono-3,5,5-trimethylhexyl itaconate), mono-7-methyloctyl itaconate, monoisodecyl itaconate, monoisoundecyl itaconate, monoisotridecyl itaconate, monoisononyl cyclohexanedicarboxylate, monoisononyl hexahydrophthalate, and monoisononyl methylhexahydrophthalate.

12 . The lubricity modifier 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, monomethyl itaconate, monoethyl itaconate, mono-n-propyl itaconate, mono-n-butyl itaconate, mono-n-octyl itaconate, mono-n-decyl itaconate, mono-n-dodecyl itaconate, 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, monoisopropyl itaconate, monoisobutyl itaconate, monoisooctyl itaconate, monoisononyl itaconate, monoisodecyl itaconate, monoisoundecyl itaconate, monoisotridecyl itaconate, mono-3-hexen-1-yl maleate, monooleyl maleate, mono-3-hexen-1-yl itaconate, monooleyl itaconate, monocyclohexyl maleate, monocyclohexyl itaconate, mono-p-nonylphenyl maleate, mono-p-nonylphenyl itaconate, monobenzyl maleate, monobenzyl itaconate, or any combination thereof.

13 . The lubricity modifier 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, methylhexahydrophthalic acid monoester, methyltetrahydrophthalic acid monoester, or any combination thereof.

14 . The fuel composition according to claim 6 , wherein, in dicarboxylic acid monoester compound represented by the formula (I),
R 1 represents a single bond, a substituted or unsubstituted C 2-4 divalent alkenyl group, or a group having a structure of —R 3 —R 4 —R 5 —; R 2 represents a substituted or unsubstituted C 1-18 hydrocarbyl group; R 3 and R 5 each independently represents a single bond or methylene; R 4 represents a substituted or unsubstituted C 3-10 divalent alicyclic group.

15 . The fuel composition according to claim 6 , wherein, in dicarboxylic acid monoester compound represented by the formula (I), R 2 is selected from the group consisting of C 1-18 linear or branched hydrocarbyl groups, C 4-18 alicyclic hydrocarbyl groups, and C 7-18 aryl-substituted hydrocarbyl groups or hydrocarbyl-substituted aryl groups.

16 . The fuel composition according to claim 6 , wherein the dicarboxylic acid monoester compound is selected from the group of maleic acid monoester, fumaric acid monoester, itaconic acid monoester, citraconic acid monoester, methyl fumaric acid monoester, 2,3-dimethyl maleic acid monoester, glutaconic acid monoester, or any combination thereof.

17 . The fuel composition according to claim 6 , wherein the dicarboxylic acid monoester compound is selected from the group consisting of 1,2-cyclopentanedicarboxylic acid monoester, 1,2-cyclohexanedicarboxylic acid monoester, tetrahydrophthalic acid monoester, methylhexahydrophthalic acid monoester, methyltetrahydrophthalic acid monoester, 1-methyl-1,2-cyclohexanedicarboxylic acid monoester, 4-methyl-1,2-cyclohexanedicarboxylic acid monoester, 3-methyl-1,2-cyclohexanedicarboxylic acid monoester, 4-methyl-4-cyclohexene-1,2-dicarboxylic acid monoester, 3-methyl-4-cyclohexene

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

• C07C67/08

  by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds · CPC title

• C07C2601/16

  the ring being unsaturated · CPC title