# US 10,479,950 B2 · Quaternary ammonium amide and/or ester salts

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- Number: US 10,479,950 B2
- Document ID: US10479950B2
- Status: Granted
- Kind: B2
- Application number: 15/660,306
- Filed: 2017-07-26
- Published: 2017-11-09
- Granted: 2019-11-19
- Earliest claimed: 2009-05-15
- Assignees: The Lubrizol Corporation
- Applicants: The Lubrizol Corporation
- Inventors: Paul R. Stevenson; James C. Ray; David J. Moreton; James H. Bush
- Web page: https://patentgrep.com/patent/US10479950B2

## CPC

- C10L 1/2381: {polyamides; polyamide-esters; polyurethane, polyureas (C10L1/221 takes precedence)}
- C08F 8/44: Preparation of metal salts or ammonium salts
- C08F 8/46: Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation
- C08F 110/10: Isobutene
- C10L 1/2222: {(cyclo)aliphatic amines; polyamines (no macromolecular substituent 30C); quaternair ammonium compounds; carbamates (C10L1/221 takes precedence)}
- C10L 1/224: Amides; Imides {carboxylic acid amides, imides (C10L1/221, C10L1/2227 take precedence)}
- C10L 1/2383: Polyamines or polyimines, or derivatives thereof {(poly)amines and imines; derivatives thereof (substituted by a macromolecular group containing 30C) (C10L1/221 takes precedence)}
- C10L 10/02: for reducing smoke development
- C10L 10/04: for minimising corrosion or incrustation
- C10L 10/18: use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
- F02B 43/02: Engines characterised by means for increasing operating efficiency
- F02B 77/04: Cleaning of, preventing corrosion or erosion in, or preventing unwanted deposits in, combustion engines
- F23J 7/00: Arrangement of devices for supplying chemicals to fire
- C10L 2200/0259: Nitrogen containing compounds
- C10L 2200/0423: Gasoline
- C10L 2230/14: for improving storage or transport of the fuel
- C10L 2250/04: Additive or component is a polymer
- C10L 2270/02: for internal combustion engines
- C10L 2270/023: for gasoline engines
- C10L: FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G OR C10K; LIQUIFIED PETROLEUM GAS; USE OF ADDITIVES TO FUELS OR FIRES; FIRE-LIGHTERS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- F02B: INTERNAL-COMBUSTION PISTON ENGINES; COMBUSTION ENGINES IN GENERAL (gas-turbine plants F02C; hot-gas or combustion-product positive-displacement engine plants F02G)
- F23J: REMOVAL OR TREATMENT OF COMBUSTION PRODUCTS OR COMBUSTION RESIDUES; FLUES (combustion apparatus for consuming smoke or fumes, e.g. exhaust gases, F23G7/06)

## Abstract

The invention relates to quaternary ammonium amide and/or ester salts and their use as additives, including their use in fuels, such as diesel fuel. The invention particularly relates to the use of quaternary ammonium amide and/or ester salts as detergents in diesel fuels.

## Claims

### Claim 1

A composition comprising a quaternary ammonium salt detergent containing an amide group, where the quaternized detergent comprises the reaction product of:
(a) a non-quaternized detergent containing an amide group, where the detergent has a tertiary amine functionality; and
(b) a quaternizing agent;
and wherein the reaction of (a) and (b) is essentially free of any additional acid component other than an acid group present in the structure of the detergent; and wherein (b) the quaternizing agent comprises ethylene oxide, propylene oxide, butylene oxide, styrene oxide, or combinations thereof.

### Claim 2 (depends on 1)

The composition of claim 1, wherein a protic solvent is present during the reaction of (a) and (b).

### Claim 3 (depends on 2)

The composition of claim 2, wherein the protic solvent comprises a linear or branched alcohol containing 1 to 10 carbon atoms.

### Claim 4 (depends on 1)

The composition of claim 1, wherein (a) the non-quaternized detergent comprises the product of a hydrocarbyl-substituted acylating agent and a compound having a nitrogen atom capable of reacting with the acylating agent and further having at least one tertiary amino group.

### Claim 5 (depends on 4)

The composition of claim 4, wherein the hydrocarbyl-substituted acylating agent comprises polyisobutylene succinic anhydride.

### Claim 6 (depends on 4)

The composition of claim 4, wherein the compound having a nitrogen atom capable of reacting with the acylating agent comprises 1-aminopiperidine, 1-(2-aminoethyl)piperidine, 1-(3-aminopropyl)-2-pipecoline, 1-methyl-(4-methylamino)piperidine, 4-(1-pyrrolidinyl)piperidine, 1-(2-aminoethyl)pyrrolidine, 2-(2-aminoethyl)-1-methylpyrrolidine, N,N-diethylethylenediamine, N,N-dimethylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethyl-1,3-diaminopropane, N,N-diethyl-1,3-diaminopropane, N,N-dibutyl-1,3-diaminopropane, N,N,N′-trimethylethylenediamine, N,N-dimethyl-N′-ethylethylenediamine, N,N-diethyl-N′-methylethylenediamine, N,N,N′-triethylethylenediamine, N,N,N′-trimethyl-1,3-propanediamine, N,N,2,2-tetramethyl-1,3-propanediamine, 2-amino-5-diethylaminopentane, N,N,N′,N′-tetraethyldiethylenetriamine, 3,3′-diamino-N-methyldipropylamine, 3,3′-iminobis(N,N-dimethylpropylamine), or combinations thereof.

### Claim 7 (depends on 4)

The composition of claim 4, wherein the compound having a nitrogen atom capable of reacting with the acylating agent comprises N,N-diethylethylenediamine, N,N-dimethylethylenediamine, N,N-dibutylethylenediamine, N,N-dimethyl-1,3-diaminopropane, N,N-diethyl-1,3-diaminopropane, or combinations thereof.

### Claim 8 (depends on 1)

A fuel composition comprising the composition of claim 1 and further comprising a fuel.

### Claim 9 (depends on 8)

The fuel composition of claim 8, further comprising one or more fuel additives other than the quaternary ammonium salt detergent.

### Claim 10 (depends on 8)

A method of operating an internal combustion engine or open flame burner comprising supplying to the engine or burner the fuel composition of claim 8.

### Claim 11

A process of making a quaternary ammonium salt detergent comprising:
I. reacting (a) a non-quaternized detergent containing an amide group, where the detergent has a tertiary amine functionality with (b) a quaternizing agent;
thereby obtaining a quaternized detergent;
wherein a protic solvent is present during the reaction of (a) and (b) and wherein the reaction of (a) and (b) is free of any additional acid component other than an acid group present in the structure of the detergent; and
wherein (b) the quaternizing agent comprises ethylene oxide, propylene oxide, butylene oxide, styrene oxide, or combinations thereof.

### Claim 12 (depends on 11)

The process of claim 11, wherein the protic solvent comprises a linear or branched alcohol containing 1 to 10 carbon atoms.

### Claim 13 (depends on 12)

The process of claim 12, wherein (a) the non-quaternized detergent comprises the product of a hydrocarbyl-substituted acylating agent and a compound having a nitrogen atom capable of reacting with the acylating agent and further having at least one tertiary amino group.

### Claim 14 (depends on 11)

A quaternized detergent made by the process of claim 11.

### Claim 15 (depends on 9)

The fuel composition of claim 9, wherein the fuel composition comprises at least one lubricity agent that is a fatty carboxylic acid.