Amine salts for use in gasoline engines

Patent metadata

Field	Value
Publication number	US-11208603-B2
Application number	US-201816643346-A
Country	US
Kind code	B2
Filing date	Mar 5, 2018
Priority date	Mar 6, 2017
Publication date	Dec 28, 2021
Grant date	Dec 28, 2021

Abstract

Fuel compositions comprising at least 10 ppm by weight of a succinic ester acid amine salt or a succinamide acid amine salt (both “amine salt(s)”). The amine salt is the product of (a) and (b), wherein: (a) is an amine with (i) at least one tertiary nitrogen and (ii) at least one hydroxy alkyl functional group and/or at least one secondary amine functionality; and (b) is a hydrocarbyl-substituted succinic acid/or anhydride. The molar ratio of (a) to (b) may range from 3:1 to 1:3. The fuel composition may comprise gasoline, oxygenate, or mixtures thereof. Methods and uses for reducing carbonaceous deposits in an engine comprising operating the engine using the fuel composition having an amine salt therein.

First claim

What is claimed is:

1. A fuel composition comprising gasoline, oxygenate, or mixtures thereof and a succinic ester acid amine salt or a succinamide acid amine salt (both “amine salt(s)”) that is the product of (a) and (b), wherein:
(a) is an amine with (i) at least one tertiary nitrogen and (ii) at least one hydroxy alkyl functionality and/or at least one secondary amine functionality;
(b) is a hydrocarbyl-substituted succinic acid and/or anhydride; and

wherein said amine salt has a concentration of at least 10 ppm by weight, based on a total weight of said fuel composition; and
wherein at least a portion of the amine salt has the formula:

wherein R 1 is hydrogen or a C 1 to C 50 linear or branched hydrocarbyl group; R 4 is a C 1 to C 5 linear or branched hydrocarbyl group; and R 5 and R 6 , are independently a C 1 to C 22 linear or branched hydrocarbyl group, or are moieties which, when taken together, form a 5-, 6-, or 7-membered ring and/or

wherein R 1 is hydrogen or a C 1 to C 50 linear or branched hydrocarbyl group; R 4 and R 7 are independently a C 1 to C 5 linear or branched hydrocarbyl group; and R 5 , R 6 , are independently a C 1 to C 22 linear or branched hydrocarbyl group, or are moieties which, when taken together, form a 5-, 6-, or 7-membered ring, n is 0 or 1, and R 8 and R 9 are independently hydrogen or a C 1 to C 22 linear or branched hydrocarbyl group, or are moieties which, when taken together, form a 5-, 6-, or 7-membered ring.

2. The fuel composition of claim 1 , wherein the molar ratio of (a) to (b) ranges from 3:1 to 1:3.

3. The fuel composition of claim 1 , wherein R 1 is a C 8 to C 25 or C 12 to C 16 hydrocarbyl group.

4. The fuel composition of claim 1 , wherein the amine salt has the formula (I) and is the product of N-methyldiethanolamine and hexadecenylsuccinic anhydride.

5. The fuel composition of claim 1 , wherein the amine salt has the formula (II) and is the product of N1-(3-(dimethylamino)propyl)-N3,N3-dimethylpropane-1,3-diamine and hexadecenylsuccinic anhydride.

6. The fuel composition of claim 1 , wherein the amine is an alkoxylated fatty amine.

7. The fuel composition of claim 1 , further comprising an alkoxylated fatty amine in addition to the amine used to make the reaction product of the amine salt.

8. The fuel composition of claim 6 or 7 , wherein said alkoxylated fatty amine has the formula (III):

wherein R is a C 4 to C 30 hydrocarbyl group; A 1 and A 2 are individually a C 1 to C 10 alkylene group; and the sum of x and y is an integer of at least 1.

9. The fuel composition of claim 1 , wherein said amine salt has a concentration of at least 12 ppm, 25 ppm, or 50 ppm, based on a total weight of said fuel composition.

10. The fuel composition of claim 1 , wherein said fuel composition comprises 0.1 vol % to 100 vol % oxygenate, based on a total volume of said fuel composition.

11. The fuel composition of claim 1 , wherein said fuel composition comprises 0.1 vol % to 100 vol % gasoline, based on a total volume of said fuel composition.

12. The fuel composition of claim 10 , wherein said oxygenate is ethanol.

13. A method of reducing carbonaceous deposits in an engine, said method comprising operating said engine using the fuel composition of claim 1 .

14. The method of claim 13 , wherein said amine salt is present in an amount of at least 20 ppm to 100 ppm (keep clean), or at least 100 ppm to 500 ppm (clean-up).

15. The method of claim 13 , wherein said engine is an internal combustion gasoline engine.

16. The method of claim 15 , wherein said internal combustion gasoline engine, is a gasoline direct injection (“GDI”) engine, a port fuel injection (“PFI”) engine, a homogeneous charge compression ignition (“HCCI”) engine, or a combination thereof.

17. The method of claim 13 , wherein said amine salt is added to said fuel using an onboard dosing system.

18. The fuel composition of claim 1 , wherein the amine salt has the formula (I) and is the product of N,N-dimethylethanolamine and hexadecenylsuccinic anhydride.

Assignees

• Lubrizol Corp

Inventors

• Bartley Stuart L
• Nyce Matthew

Classifications

• C10L1/1905 Primary

  of di- or polycarboxylic acids · CPC title

• C10L2200/0423

  Gasoline · CPC title

• C10L1/1824

  mono-hydroxy · CPC title

• C10L1/2387

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

• C10L1/1616

  fractions, e.g. lubricants, solvents, naphta, bitumen, tars, terpentine · CPC title