Quaternary ammonium compounds as fuel or lubricant additives

Patent metadata

Field	Value
Publication number	US-11066617-B2
Application number	US-201916450362-A
Country	US
Kind code	B2
Filing date	Jun 24, 2019
Priority date	Jul 26, 2013
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

A quaternary ammonium compound of formula (X):

wherein R 0 , R 1 , R 2 and R 3 is each individually an optionally substituted alkyl, alkenyl or aryl group and R includes an optionally substituted hydrocarbyl moiety having at least 5 carbon atoms.

First claim

The invention claimed is:

1. A method of preparing a fuel composition, said method comprising: preparing a quaternary ammonium compound by reacting:
(a) a tertiary amine of formula R 1 R 2 R 3 N with;
(b) an epoxide; in the presence of
(c) a monoester of a diacid including an optionally substituted hydrocarbyl moiety having at least 5 carbon atoms;
wherein R 1 , R 2 and R 3 are each independently selected from an optionally substituted alkyl, alkenyl or aryl group; and mixing the quaternary ammonium compound into a fuel;
and wherein the quaternary ammonium compound has the formula (Y):

wherein R 1 , R 2 and R 3 are each independently selected from an optionally substituted alkyl, alkenyl or aryl group; R 4 , R 5 , R 6 and R 7 are each independently selected from hydrogen or an optionally substituted alkyl, alkenyl or aryl group; and R includes an optionally substituted alkyl or alkenyl moiety having at least 6 carbon atoms; and wherein RCOO − is the residue of a monoester of a diacid.

2. The method according to claim 1 wherein each of R 1 and R 2 is independently alkyl, alkenyl or aryl group having from 1 to 50 carbon atoms optionally substituted with one or more groups selected from halo, hydroxy, alkoxy, keto, acyl, cyano, mercapto, alkylmercapto, dialkylamino, nitro, nitroso, and sulphoxy.

3. The method according to claim 1 wherein R 3 is an alkyl or alkenyl group having from 1 to 50 carbon atoms optionally substituted with one or more substituents selected from halo, hydroxy, alkoxy, keto, acyl, cyano, mercapto, alkylmercapto, amino, alkylamino, nitro, nitroso, sulphoxy, amido, alkyamido, imido and alkylimido.

4. The method according to claim 1 wherein R 3 is an alkyl or alkenyl group optionally substituted with alkoxy or hydroxy groups.

5. The method according to claim 1 wherein each of R 1 and R 2 is an unsubstituted alkyl group or a hydroxy substituted alkyl group.

6. The method according to claim 1 wherein R 3 is selected from:
(x) an optionally substituted alkylene phenol moiety of formula (A) or (B)

wherein n is 0 to 4, preferably 1, R is an optionally substituted hydrocarbyl group, R′ is an optionally substituted alkyl, alkenyl or aryl group; and L is a linking group;
(y) a succinimide moiety of formula:

wherein R is an optionally substituted hydrocarbyl group and L is a linking group; and
(z) a polyisobutenyl group having a molecular weight of from 100 to 5000.

7. The method according to claim 1 wherein each of R 1 , R 2 and R 3 is selected from an alkyl or hydroxyl alkyl group having 1 to 10 carbon atoms.

8. The method according to claim 1 wherein epoxide (b) is selected from styrene oxide, ethylene oxide, propylene oxide, butylene oxide, epoxyhexane, octene oxide, stilbene oxide, other alkyl and alkenyl oxides having 2 to 50 carbon atoms, glycidyl ethers and glycidyl esters.

9. The method according to claim 1 wherein the fuel is diesel fuel and optionally further comprises one or more detergents selected from:
(i) an additional quaternary ammonium salt additive which is not a quaternary ammonium compound of claim 1 ;
(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.

10. The method according to claim 1 wherein the fuel is gasoline fuel and optionally comprises one or more gasoline detergents selected from:
(p) hydrocarbyl-substituted polyoxyalkylene amines or polyetheramines;
(q) acylated nitrogen compounds which are the reaction product of a carboxylic acid-derived acylating agent and an amine;
(r) hydrocarbyl-substituted amines wherein the hydrocarbyl substituent is substantially aliphatic and contains at least 8 carbon atoms;
(s) Mannich base additives comprising nitrogen-containing condensates of a phenol, aldehyde and primary or secondary amine;
(t) aromatic esters of a polyalkylphenoxyalkanol;
(u) an additional quaternary ammonium salt additive which is not a quaternary ammonium compound of claim 1 ; and
(v) tertiary hydrocarbyl amines having a maximum of 30 carbon atoms.

11. A method of improving the performance of an engine, the method comprising: preparing a fuel composition according to the method of claim 1 ; and combusting said fuel composition in the engine.

12. The method according to claim 11 wherein the engine is a gasoline engine and the fuel is gasoline.

13. The method according to claim 11 wherein the engine is a diesel engine having a fuel injection system which comprises a high pressure fuel injection (HPFI) system with fuel pressure greater than 1350 bar.

14. The method according to claim 11 wherein improvement in performance is achieved by combating deposits in the engine.

15. The method according to claim 11 which combats internal diesel injector deposits.

16. The method according to claim 11 which combats external diesel injector deposits, including injector nozzle deposits and injector tip deposits.

17. The method according to claim 11 which combats fuel filter deposits.

18. The method according to claim 11 which achieves “keep clean” performance.

19. The method according to claim 11 which achieves “clean up” performance.

20. The method according to claim 2 wherein said halo is chloro or fluoro.

21. The method according to claim 3 wherein said halo is chloro or fluoro.

22. The method according to claim 6 wherein said polyisobutenyl group having a molecular weight of from 500 to 2000.

Assignees

• Innospec Ltd

Inventors

• Reid Jacqueline
• Cook Stephen L

Classifications

• C10L1/232

  containing nitrogen in a heterocyclic ring {(C10L1/221 takes precedence)} · CPC title

• C07C213/08

  by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups · CPC title

• C11D1/62

  Quaternary ammonium compounds · CPC title

• C10M2217/043

  Mannich bases · CPC title

• C10M2215/04

  having amino groups bound to acyclic or cycloaliphatic carbon atoms · CPC title