Use of specific derivatives of quaternized nitrogen compounds as additives in fuels and lubricants

Patent metadata

Field	Value
Publication number	US-10370610-B2
Application number	US-201415022681-A
Country	US
Kind code	B2
Filing date	Sep 19, 2014
Priority date	Sep 20, 2013
Publication date	Aug 6, 2019
Grant date	Aug 6, 2019

Abstract

The invention relates to the use of specific quaternized nitrogen compounds which are also subjected to specific transesterification or amidation, as a fuel and lubricant additive or kerosene additive, such as in particular as a detergent additive, for decreasing or preventing deposits in the injection systems of direct-injection diesel engines, in particular in common rail injection systems, for decreasing the fuel consumption of direct-injection diesel engines, in particular of diesel engines having common rail injection systems, and for minimizing the power loss in direct-injection diesel engines, in particular in diesel engines having common rail injection systems. The invention further relates to the use as an additive for petrol, in particular for operation of DISI engines.

First claim

The invention claimed is:

1. A process, comprising operating a direct injection diesel engine with a fuel comprising an additive comprising a quaternized nitrogen compound, wherein presence of the additive reduces fuel consumption, minimizes power loss, or both,
wherein the quaternized nitrogen compound is obtained by:
a) reacting a quaternizable nitrogen compound comprising a quaternizable amino group with a quaternizing agent which converts the quaternizable amino group to a quaternary ammonium group, the quaternizing agent being a C 1 -C 4 -alkyl ester of an aliphatic, cycloaromatic or cycloaliphatic polycarboxylic acid, to obtain a quaternization product; and
b) transesterifying or amidating a remaining ester group of the quaternization product,
wherein:
the quaternizing agent is an alkyl ester of an aliphatic, cycloaromatic or cycloaliphatic polycarboxylic acid;
the transesterifying occurs with
a saturated or unsaturated, linear, branched or cyclic, aliphatic C 5 -C 28 mono-alcohol or polyol,
a partly esterified polyol having at least one free hydroxyl group, or
a polyisobutylene alcohol obtained by hydroformylating and reducing a polyisobutene, having a molecular mass ranging from 150 to 5000, found by gel permeation chromatography (THF solvent, polystyrene standard) of the polyisobutylene alcohol,

or
the transesterifying occurs by replacing a methyl or ethyl group in the remaining ester group of the quaternization product with a hydrocarbyl radical having 5 to 50 carbon atoms from a long-chain alcohol; and
the amidating occurs with
a saturated or unsaturated, linear, branched or cyclic, aliphatic, primary or secondary aliphatic C 5 -C 28 mono- or polyamine, or
a polyisobutyleneamine.

2. A process, comprising operating a diesel engine with a fuel comprising an additive comprising a quaternized nitrogen compound, wherein presence of the additive reduces, prevents, or both, deposits in the intake system of the diesel engine,
wherein the quaternized nitrogen compound is obtained by:
a) reacting a quaternizable nitrogen compound comprising a quaternizable amino group with a quaternizing agent which converts the quaternizable amino group to a quaternary ammonium group, the quaternizing agent being a C 1 -C 4 -alkyl ester of an aliphatic, cycloaromatic or cycloaliphatic polycarboxylic acid, to obtain a quaternization product; and
b) transesterifying or amidating a remaining ester group of the quaternization product,
wherein:
the quaternizing agent is an alkyl ester of an aliphatic, cycloaromatic or cycloaliphatic polycarboxylic acid;
the transesterifying occurs with
a saturated or unsaturated, linear, branched or cyclic, aliphatic C 1 -C 28 mono-alcohol or polyol,
a partly esterified polyol having at least one free hydroxyl group, or
a polyisobutylene alcohol obtained by hydroformylating and reducing a polyisobutene, having a molecular mass ranging from 150 to 5000, found by gel permeation chromatography (THF solvent, polystyrene standard) of the polyisobutylene alcohol,

or
the transesterifying occurs by replacing a methyl or ethyl group in the remaining ester group of the quaternization product with a hydrocarbyl radical having 5 to 50 carbon atoms from a long-chain alcohol; and
the amidating occurs with
a saturated or unsaturated linear, branched or cyclic, aliphatic, primary or secondary aliphatic C 5 -C 28 mono- or polyamine, or
a polyisobutyleneamine.

3. The process of claim 1 , wherein the quaternizable nitrogen compound is selected from the group consisting of:
a) at least one alkylamine of formula (3):
R a R b R c N  (3),

wherein
at least one of the R a , R b and R c radicals is a straight-chain or branched, saturated or unsaturated C 8 -C 40 -hydrocarbyl radical and the other radicals are identical or different, straight-chain or branched, saturated or unsaturated C 1 -C 6 -hydrocarbyl radicals, or
all the R a , R b and R c radicals are identical or different, straight-chain or branched, saturated or unsaturated C 8 -C 40 -hydrocarbyl radicals;
b) at least one polyalkene-substituted amine comprising at least one quaternizable amino group;
c) at least one polyether-substituted amine comprising at least one quaternizable amino group;
d) at least one reaction product of a hydrocarbyl-substituted acylating agent and a compound comprising a nitrogen or oxygen atom and additionally comprising at least one quaternizable amino group; and
e) mixtures thereof.

4. The process of claim 1 , wherein the quaternizing agent is a compound of formula (2):
R 1 OC(O)-A-C(O)OR 1a   (2),

wherein:
R 1 and R 1a are each independently a lower alkyl radical; and
A is a chemical bond or an optionally mono- or polysubstituted hydrocarbylene, or an optionally substituted monocyclic arylene or cycloalkylene radical.

5. The process of claim 1 , wherein the transesterifying occurs by reaction with at least one saturated or unsaturated linear, branched or cyclic aliphatic mono-alcohol or polyol; or
the amidating occurs by reaction with at least one saturated or unsaturated linear, branched or cyclic aliphatic primary or secondary mono-amine or polyamine.

6. The process of claim 3 , wherein the quaternizable nitrogen compound is a compound of the formula (3), wherein at least two of the R a , R b and R c radicals are the same or different and are each a straight-chain or branched C 10 -C 20 -alkyl radical and the other radical is C 1 -C 4 -alkyl.

7. The process of claim 1 , wherein the quaternizing agent is selected from the group consisting of a di-C 1 -C 4 -alkyl phthalate and a di-C 1 -C 4 -alkyl oxalate.

8. The process of claim 2 , wherein the quaternizable nitrogen compound is selected from the group consisting of:
a) at least one alkylamine of formula (3):
R a R b R c N  (3),

wherein
at least one of the R a , R b and R c radicals is a straight-chain or branched, saturated or unsaturated C 8 -C 40 -hydrocarbyl radical and the other radicals are identical or different, straight-chain or branched, saturated or unsaturated C 1 -C 6 -hydrocarbyl radicals, or
all the R a , R b and R c radicals are identical or different, straight-chain or branched, saturated or unsaturated C 8 -C 40 -hydrocarbyl radicals;
b) at least one polyalkene-substituted amine comprising at least one quaternizable amino group;
c) at least one polyether-substituted amine comprising at least one quaternizable amino group;
d) at least one reaction product of a hydrocarbyl-substituted acylating agent and a compound comprising a nitrogen or oxygen atom and additionally comprising at least one quaternizable amino group; and
e) mixtures thereof.

9. The process of claim 2 , wherein the quaternizing agent is a compound of formula (2):
R 1 OC(O)-A-C(O)OR 1a ,  (2),

wherein:
R 1 and R 1a are each independently a lower alkyl radical; and
A is a chemical bond or an optionally mono- or polysubstituted hydrocarbylene, or an optionally substituted monocyclic arylene or cycloalkylene radical.

10. The process of claim 2 , wherein the transesterifying occurs by reaction with at least one saturated or unsaturated linear, branched or cyclic aliphatic mono-alcohol or polyol; or
the amidating occurs by reaction with at least one saturated or unsaturated linear, branched or cyclic aliphatic primary or secondary mono-amine or polyamine.

11. The process of claim 8 , wherein the quaternizable nitrogen compound is a compound of the formula (3), wherein at least two of the R a , R b and R c radicals are the same or different and are each a straight-chain or branched C 10 -C 20 -alkyl radical and the other radical is C 1 -C 4 -alkyl.

12

Assignees

• Basf Se

Inventors

• Hansch Markus
• Boehnke Harald
• Grabarse Wolfgang
• Voelkel Ludwig
• Peretolchin Maxim

Classifications

• C10N2070/02

  Concentrating of additives · CPC title

• C10N2040/253

  Small diesel engines · CPC title

• C10N2040/25

  Internal-combustion engines · CPC title

• C10N2030/70

  Soluble oils · CPC title

• C10N2030/08

  Resistance to extreme temperature · CPC title