# US 10,308,593 B2 · Additives for fuel oils

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- Number: US 10,308,593 B2
- Document ID: US10308593B2
- Status: Granted
- Kind: B2
- Application number: 12/634,796
- Filed: 2009-12-10
- Published: 2010-09-23
- Granted: 2019-06-04
- Earliest claimed: 2009-03-18
- Assignees: Infineum International Limited
- Applicants: Graham Jackson
- Inventors: Graham Jackson
- Web page: https://patentgrep.com/patent/US10308593B2

## CPC

- C07C 237/08: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C 229/12: to carbon atoms of acyclic carbon skeletons
- C07C 229/24: having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
- C07C 237/06: having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C 237/10: having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
- C10L 1/143: {mixtures of organic macromolecular compounds with organic non-macromolecular compounds}
- C10L 1/221: {compounds of uncertain formula; reaction products where mixtures of compounds are obtained}
- 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 10/00: Use of additives to fuels or fires for particular purposes (additives for liquid carbonaceous fuels characterised by their chemical nature C10L1/10; using binders for briquetting solid fuels C10L5/10; using additives to improve the combustion of solid fuels C10L9/10)
- C10L 10/14: for improving low temperature properties
- C10L 10/18: use of detergents or dispersants for purposes not provided for in groups C10L10/02 - C10L10/16
- C10L 1/1658: {from compounds containing conjugated dienes}
- C10L 1/19: Esters {ester radical containing compounds; ester ethers; carbonic acid esters (C10L1/1802, C10L1/1805, C10L1/1808, C10L1/1811, C10L1/1814, C10L1/1817 take precedence)}
- C10L 1/1973: {mono-carboxylic}
- C10L 1/1976: {poly-carboxylic}
- C10L 1/1981: {Condensation polymers of aldehydes or ketones}
- C10L 1/2225: {hydroxy containing (C10L1/221 takes precedence)}
- C10L 1/223: having at least one amino group bound to an aromatic carbon atom {(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)}
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- 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

## Abstract

A fuel oil composition comprising a major amount of a fuel oil and a minor amount of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more α,β-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms. The fuel oil composition has improved low temperature properties.

## Claims

### Claim 1

A fuel oil composition comprising (a) a major amount of a fuel oil; and (b) 10-500 ppm by weight based on the weight of the fuel oil of a compound being the product of the 1,4-addition reaction of (i) ammonia, a primary or secondary hydrocarbyl-substituted amine or a mixture thereof to (ii) a species containing one or more α,β-unsaturated carbonyl groups, wherein the compound includes at least one hydrocarbyl group containing at least 10 carbon atoms; and
wherein species (ii) is of formula A-B,
wherein A comprises a moiety of general formula I which is bonded to B via the carbonyl group:
wherein R3 represents hydrogen, C1 to C8 hydrocarbyl group, or C(O)OR5,
wherein R4 represents C1 to C8 hydrocarbyl group, or —C(O)OR5, where R5 represents a hydrocarbyl group, containing from 1 to 40 carbon atoms,
wherein B independently represents —NR6R7 or —OR8,
wherein R6 and R7 each independently represent hydrogen or a hydrocarbyl group, containing up to 40 carbon atoms which group is optionally substituted or terminated with one or more substituents selected from —OR9, —NR10R11, or a combination thereof, and/or interrupted by one or more oxygen atoms and/or —N(R12)— groups, where R9, R10, R11 and R12 each independently represent hydrogen, a hydrocarbyl group containing up to 20 carbon atoms, or a moiety of general formula I; and,
wherein R8 independently represents hydrogen or a hydrocarbyl group, containing up to 40 carbon atoms which group is optionally substituted or terminated with one or more substituents of —NR14R15, and/or interrupted by one or more —N(R16)— groups, where R14, R15 and R16 each independently represent hydrogen, a hydrocarbyl group containing up to 20 carbon atoms, or a moiety of general formula I as defined herein.

### Claim 2 (depends on 1)

The fuel oil composition according to claim 1 wherein species (ii) comprises an α,β-unsaturated amide or, an α,β-unsaturated ester.

### Claim 3 (depends on 2)

The fuel oil composition according to claim 2 wherein species (ii) comprises an acrylamide, a methacrylamide, an acrylic acid ester, a methacrylic acid ester, a crotonoic acid ester, a fumaric acid ester or a maleic acid ester.

### Claim 4 (depends on 1)

The fuel oil composition according to claim 1 wherein species (ii) contains two or more α,β-unsaturated carbonyl groups.

### Claim 5 (depends on 1)

The fuel oil composition according to claim 1 wherein (i) is of the formula NHR1R2, where R1 independently represents a hydrocarbyl group containing from 8 to 40 carbon atoms, and R2 independently represents hydrogen or a hydrocarbyl group containing up to 40 carbon atoms.

### Claim 6 (depends on 1)

The fuel oil composition wherein the compound according to claim 1 is reacted with (iii) a hydrocarbyl compound containing one or more hydroxy, primary or secondary amino functional groups.

### Claim 7 (depends on 1)

The fuel oil composition according to claim 1 further comprising one or more of an ethylene-unsaturated ester copolymer, a comb polymer, an alkyl-phenol formaldehyde condensate, a hydroxy-benzoate formaldehyde condensate and a hydrocarbon polymer.

### Claim 8 (depends on 1)

An additive composition comprising a compound as defined in claim 1 and a compatible solvent therefor.

### Claim 9 (depends on 1)

The fuel oil composition according to claim 1 further comprising a fuel oil detergent.

### Claim 10 (depends on 1)

The fuel oil composition according to claim 1 wherein R5 represents an alkyl group.

### Claim 11 (depends on 1)

The fuel oil composition according to claim 1 wherein R6 and R7 each independently represent hydrogen or an alkyl group.

### Claim 12 (depends on 1)

The fuel oil composition according to claim 1 wherein R8 independently represents hydrogen or an alkyl group.

### Claim 13 (depends on 5)

The fuel oil composition according to claim 5 wherein R1 independently represents an alkyl group.

### Claim 14 (depends on 5)

The fuel oil composition according to claim 5 wherein R2 independently represents hydrogen or an alkyl group.

### Claim 15

A fuel oil composition comprising (a) a major amount of a fuel oil; and (b) 10-500 ppm by weight based on the weight of the fuel oil of a compound being the product of the 1,4-addition reaction of (i) an amine represented by the formula NHR1R2, where R1 and R2 each independently represent hydrogen or a hydrocarbyl group which group is optionally terminated with one or more substituents selected from —OH or —NH2 and/or interrupted by one or more oxygen atoms or —N(H)— groups to (ii) a species represented by general formula Ill
wherein R3 represents hydrogen or a C1 to C8 hydrocarbyl group, wherein R4 represents —C(O)OR5, where R5 and R8 independently represent a hydrocarbyl group containing from 1 to 40 carbon atoms.