Quaternary ammonium compound and fuel composition

Patent metadata

Field	Value
Publication number	US-11566197-B2
Application number	US-201917277975-A
Country	US
Kind code	B2
Filing date	Sep 12, 2019
Priority date	Sep 19, 2018
Publication date	Jan 31, 2023
Grant date	Jan 31, 2023

Abstract

A quaternary ammonium compound of formula (I): wherein R0, R1, R2 and R3 is each independently an optionally substituted hydrocarbyl group; X is a linking group; R4 is an optionally substituted alkylene group; n is a positive integer; W is O− or OH; b is 1 when W is OH, and b is 2 when W is O−.

First claim

The invention claimed is:

1. A method of preparing a quaternary ammonium compound, the method comprising reacting (a) a tertiary amine of formula R 1 R 2 R 3 N with (b) an epoxide; in the presence of (c) a compound of formula (IIB):

wherein R 1 , R 2 , and R 3 is each independently an optionally substituted hydrocarbyl group; R 4 is an optionally substituted alkylene group; n is 0 or a positive integer; c is at least 1; and each X is CH 2 CHR or CHCH 2 R wherein R is an optionally substituted hydrocarbyl group.

2. A composition comprising a quaternary ammonium compound of formula (I):

wherein R 0 , R 1 , R 2 and R 3 is each independently an optionally substituted hydrocarbyl group; X is a linking group; R 4 is an optionally substituted alkylene group; n is a positive integer; c is at least 1; W is O − or OH; b is 1 when W is OH, and b is 2 when W is O − ; and a fuel or lubricating oil.

3. An additive composition for a fuel or lubricating oil comprising a quaternary ammonium compound of formula (I):

wherein R 0 , R 1 , R 2 and R 3 is each independently an optionally substituted hydrocarbyl group; each X is CH 2 CHR or CHCH 2 R wherein R is an optionally substituted hydrocarbyl group; R 4 is an optionally substituted alkylene group; n is a positive integer; c is at least 1; W is O − or OH; b is 1 when W is OH, and bis 2 when W is O − ; and a diluent or carrier.

4. A method of improving the performance of an engine, the method comprising combusting in the engine a fuel composition comprising as an additive a quaternary ammonium compound of formula (I):

wherein R 0 , R 1 , R 2 and R 3 is each independently an optionally substituted hydrocarbyl group; X is a linking group; R 4 is an optionally substituted alkylene group; n is a positive integer; c is at least 1; W is O − or OH; b is 1 when W is OH, and b is 2 when W is O − .

5. The method according to claim 1 wherein the compound of formula (JIB) is derived from a hydrocarbyl substituted succinic acid or a hydrocarbyl substituted succinic anhydride.

6. The composition according to claim 2 wherein each X is a moiety CH 2 CHR or CRHCH 2 in which R is an alkyl or alkenyl group having 6 to 36 carbon atoms.

7. The composition according to claim 2 wherein each R 4 is ethylene or propylene.

8. The composition according to claim 2 wherein n is from 1 to 20.

9. The composition according to claim 2 wherein each of R 1 and R 2 is independently an optionally substituted alkyl group having from 1 to 12 carbon atoms.

10. The composition according to claim 2 wherein R 3 is an alkyl group having 1 to 24 carbon atoms.

11. The composition according to claim 2 wherein R 3 is selected from benzyl, or a hydroxyalkyl or hydroxyalkoxyalkyl group having 2 to 20 carbon atoms.

12. The composition according to claim 2 wherein R 3 is selected from:
(1) a polyisobutenyl group having a number average molecular weight of from 100 to 5000;
(2) an optionally substituted alkylene phenol moiety of formula (A) or (B)

wherein n is 0 to 4, R x is an optionally substituted hydrocarbyl group, R y is an optionally substituted alkyl, alkenyl or aryl group; and L is a linking group; and
(3) a succinimide moiety of formula:

wherein R z is an optionally substituted hydrocarbyl group and L is a linking group.

13. The composition according to claim 2 wherein R 0 as is a group of formula:

wherein each of R 9 , R 10 , R 11 , R 12 is independently selected from hydrogen or an optionally substituted alkyl, alkenyl or aryl group.

14. The composition according to claim 2 wherein the composition is a diesel fuel composition.

15. The composition according to claim 14 wherein the diesel fuel composition comprises one or more further detergents selected from:
(i) a quaternary ammonium salt additive;
(ii) the product of a Mannich reaction between an aldehyde, an amine and an optionally substituted phenol;
(iii) the reaction product of a carboxylic acid-derived acylating agent and an amine;
(iv) the reaction product of a carboxylic acid-derived acylating agent and hydrazine;
(v) a salt formed by the reaction of a carboxylic acid with di-n-butylamine or tri-n-butylamine;
(vi) the reaction product of a hydrocarbyl-substituted dicarboxylic acid or anhydride and an amine compound or salt which product comprises at least one amino triazole group; and
(vii) a substituted polyaromatic detergent additive.

16. The composition according to claim 14 wherein the diesel fuel composition comprises a mixture of two or more quarternary ammonium compounds.

17. The method according to claim 4 wherein the additive is effective as a detergent to combat deposits in a diesel fuel composition in a diesel engine.

18. The method according to claim 4 which is carried out in a diesel engine having a high pressure fuel system of more than 1350 bar.

19. The method according to claim 4 which achieves “keep clean” performance.

20. The method according to claim 4 which achieves “clean up” performance.

21. The method according to claim 17 wherein the deposits are injector deposits.

22. The method according to claim 21 wherein the deposits are internal diesel injector deposits.

23. The method according to claim 4 which achieves an improvement in performance when compared to a method of combusting a fuel composition identical to the claimed composition but free of the compound of formula (I) selected from one or more of:
a reduction in power loss of the engine;
a reduction in external diesel injector deposits;
a reduction in internal diesel injector deposits;
an improvement in fuel economy;
a reduction in fuel filter deposits;
a reduction in emissions; and
an increase in maintenance intervals.

24. The method according to claim 23 which provides an improvement in performance in diesel engines having a high pressure fuel system of more than 1350 bar.

25. The composition according to claim 2 which further comprises one or more further additives selected from lubricity improvers, corrosion inhibitors and cold flow improvers.

26. The composition according to claim 7 wherein each R 4 is —CH 2 CH 2 — or —CH(CH 3 )CH 2 —.

27. The composition according to claim 7 wherein each R 4 is —CH(CH 3 )CH 2 —.

28. The composition according to claim 12 wherein the polyisobutenyl group has a number average molecular weight of from 450 to 2500.

29. The composition according to claim 12 wherein n is 1.

Assignees

• Innospec Ltd

Inventors

• Ross Alan Norman
• Petts Matthew

Classifications

• C10L10/06

  for facilitating soot removal · CPC title

• C07C69/34 Primary

  Esters of acyclic saturated polycarboxylic acids having an esterified carboxyl group bound to an acyclic carbon atom · CPC title

• C10L1/191

  of di- or polyhydroxyalcohols · CPC title

• C10L2270/026

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

• C07C67/08

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