Diesel fuel compositions

Patent metadata

Field	Value
Publication number	US-9932535-B2
Application number	US-201214236759-A
Country	US
Kind code	B2
Filing date	Aug 2, 2012
Priority date	Aug 3, 2011
Publication date	Apr 3, 2018
Grant date	Apr 3, 2018

Abstract

A diesel fuel composition comprising a first additive (i) comprising a quaternary ammonium salt and a second additive (ii) comprising a Mannich reaction product; wherein the quaternary ammonium salt additive (i) is formed by the reaction of a compound of formula (A): R O O R1 10 (A) and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2): 15 N X R3 R2 NHR4 N X R3 R2 [O(CH2)m]nOH (B1) (B2) wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R1 is a C1 to C22 alkyl, aryl or alkylaryl group; wherein R2 and R3 are the same or different alkyl, alkenyl or aryl groups having from 1 to 22 carbon atoms; X is a bond or alkylene group having from 1 to 20 20 carbon atoms; n is from 0 to 20; m is from 1 to 5; and R4 is hydrogen or a C1 to C22 alkyl group; and wherein the Mannich reaction product additive (ii) is the product of a Mannich reaction between: (d) an aldehyde; (e) an amine; and25 (f) a substituted phenol; wherein the phenol is substituted with at least one branched hydrocarbyl group having a molecular weight of between 200 and 3000.

First claim

The invention claimed is:

1. A diesel fuel composition comprising a first additive (i) comprising a quaternary ammonium salt and a second additive (ii) comprising a Mannich reaction product;
wherein the quaternary ammonium salt additive (i) is formed by the reaction of a compound of formula (A):

wherein the compound of formula (A) is an ester of a carboxylic acid selected from the group consisting of a substituted aromatic carboxylic acid and a polycarboxylic acid,
and a compound formed by the reaction of a hydrocarbyl-substituted acylating agent and an amine of formula (B1) or (B2):

wherein R is an optionally substituted alkyl, alkenyl, aryl or alkylaryl group; R 1 is a C 1 to C 22 alkyl, aryl or alkylaryl group; wherein R 2 and R 3 are the same or different alkyl, alkenyl or aryl groups having from 1 to 22 carbon atoms; X is a bond or alkylene group having from 1 to 20carbon atoms; n is from 0 to 20; m is from 1 to 5; and R 4 is hydrogen or a C 1 to C 22 alkyl group; and wherein the Mannich reaction product additive (ii) is the product of a Mannich reaction between:
(a) an aldehyde;
(b) an amine; and
(c) a substituted phenol;

wherein the phenol is substituted with at least one branched hydrocarbyl group having a molecular weight of between 400 and 3000.

2. The diesel fuel composition according to claim 1 wherein the compound of formula (A) is selected from dimethyl oxalate, methyl 2-nitrobenzoate and methyl salicylate.

3. The diesel fuel composition according to claim 1 wherein the hydrocarbyl substituted acylating agent is reacted with a diamine compound of formula (B1).

4. The diesel fuel composition according to claim 1 wherein additive (i) is a salt of tertiary amine prepared from dimethylaminopropylamine and a polyisobutylene-substituted succinic anhydride.

5. The diesel fuel composition according to claim 1 wherein component (a) used to prepare additive (ii) is formaldehyde.

6. The diesel fuel composition according to claim 1 wherein component (b) used to prepare additive (ii) is a (poly)ethylene polyamine.

7. The diesel fuel composition according to claim 1 wherein component (c) used to prepare additive (ii) is a polyisobutylene-substituted phenol.

8. The diesel fuel composition according to claim 1 wherein in the Mannich reaction used to form additive (ii) the molar ratio of component (a) to component (b) is 2.2-1.01:1; the molar ratio of component (a) to component (c) is 1.99-1.01:1 and the molar ratio of component (b) to component (c) is 1:1.01-1.99.

9. The diesel fuel composition according to claim 8 wherein in the reaction used to make the Mannich additive the molar ratio of component (a) to component (b) is 2-1.4:1, the molar ratio of component (a) to component (c) is 1.7-1.1:1 and the molar ratio of component (b) to component (c) is 1:1.1-1.7.

10. The diesel fuel composition according to claim 1 wherein the diesel fuel comprises a Fischer Tropsch fuel and/or biodiesel.

11. The diesel fuel composition according to claim 1 which further comprises a fuel-borne catalyst which includes a metal selected from iron, cerium, group I and group II metals, platinum, manganese and mixtures thereof.

12. An additive package which upon addition to a diesel fuel provides a composition as claimed in claim 1 .

13. A method of operating a diesel engine, the method comprising combusting in the engine a composition as claimed in claim 1 .

Assignees

• Reid Jacqueline
• Innospec Ltd

Inventors

• Reid Jacqueline

Classifications

• C10L1/2387

  Polyoxyalkyleneamines {(poly)oxyalkylene amines and derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} · CPC title

• C10L2270/026

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

• C10L1/2383

  Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)} · CPC title

• C10L10/18

  use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16 · CPC title

• C10L1/238

  obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} · CPC title