Demulsifier for quaternary ammonium salt containing fuels

Patent metadata

Field	Value
Publication number	US-11008526-B2
Application number	US-201916519910-A
Country	US
Kind code	B2
Filing date	Jul 23, 2019
Priority date	Jul 23, 2019
Publication date	May 18, 2021
Grant date	May 18, 2021

Abstract

Described herein are fuel performance additives, fuels including such additive, methods of improving the demulsiliblity of fuels using fuel performance additives, and the use of a fuel performance additive to improve the demulsiliblity of fuel where such fuels are gasoline or diesel and further include a quaternary ammonium salt obtained from at least the reaction of a nitrogen containing compound having at least a tertiary amino group and a quaternizing agent.

First claim

What is claimed is:

1. A fuel performance additive comprising:
(a) a quaternary ammonium salt obtained from the reaction of a nitrogen containing compound having at least a tertiary amino group and a quaternizing agent; and
(b) a demulsifier component including a blend of (i) at least two alkoxylated phenol formaldehyde polymers including (i-1) a first alkoxylated phenol formaldehyde polymer having a relative solubility number of 18 to 22 and (i-2) a second alkoxylated phenol formaldehyde polymer having a relative solubility number of 12 to 16; (ii) an alkoxylated fatty acid polymer having a relative solubility number of 12 to 16; and (iii) an alkoxylated polyimine polymer having a relative solubility number of less than 10.

2. The fuel performance additive of claim 1 , wherein the first alkoxylated phenol formaldehyde polymer is an ethoxylated phenol formaldehyde polymer having about 25 to about 75 moles of ethylene oxide.

3. The fuel performance additive of claim 1 , wherein the second alkoxylated phenol formaldehyde polymer is an ethoxylated and propoxylated phenol formaldehyde polymer having about 5 to 30 moles of ethylene oxide and propylene oxide combined.

4. The fuel performance additive of claim 1 , wherein the alkoxylated fatty acid polymer is derived from a dimer fatty diacid, a trimer fatty triacid, a dimer fatty diol and/or a trimer fatty triol and at least one alkylene oxide derived groups and has about 5 to about 30 total moles of alkoxylation.

5. The fuel performance additive of claim 1 , wherein the alkoxylated polyimine has about 10 to about 50 moles of alkoxylation.

6. The fuel performance additive of claim 1 , wherein the demulsifier component includes a blend of about 10 to about 50 weight percent of the first alkoxylated phenol formaldehyde, about 10 to about 50 weight percent of the second alkoxylated phenol formaldehyde polymer, about 10 to about 50 weight percent of the alkoxylated fatty acid polymer, and about 1 to about 15 weight percent of the alkoxylated polyimine.

7. The fuel performance additive of claim 1 , further including a weight ratio of the quaternary ammonium salt to the demulsifier component of about 5:1 to about 1:1.

8. The fuel performance additive of claim 1 , further including about 45 to about 190 total moles of alkoxylation provided by blend of (i), (ii), and (iii).

9. The fuel performance additive of claim 1 , wherein the nitrogen containing compound of the quaternary ammonium salt is the reaction product of a hydrocarbyl-substituted acylating agent and a compound having an oxygen or nitrogen atom capable of condensing with the hydrocarbyl-substituted acylating agent and including the tertiary amino group.

10. The fuel performance additive of claim 9 , wherein the nitrogen containing compound is a polyamine including the tertiary amino group and a primary amine, a secondary amine, or combinations thereof.

11. The fuel performance additive of claim 9 , wherein the hydrocarbyl-substituted acylating agent is a hydrocarbyl substituted succinic acid, ester, anhydride, mono-acid/mono-ester, or diacid.

12. The fuel performance additive of claim 1 , wherein the quaternizing agent is selected from the group consisting of hydrocarbyl substituted carboxylates, carbonates, cyclic carbonates, phenates, epoxides, carbamates, halides, sulfates, sulfites, sulfides, sulfonates, phosphates, phosphonates, salicylates, oxalates, or mixtures thereof.

13. The fuel performance additive of claim 1 , wherein the quaternary ammonium salt is a hydrocarbyl soluble quaternary ammonium carboxylate derived from a reaction of a quaternary ammonium carbonate with an organic acid.

14. The fuel performance additive of claim 13 , wherein the quaternary ammonium carbonate is formed by reacting a carbonic acid diester with a tertiary amido amine compound.

15. The fuel performance additive of claim 13 , wherein the quaternary ammonium carbonate is selected from the group consisting of succinimidoalkyl trialkyl ammonium carbonates, succinamido/succinyl ester ammonium carbonates and amidoalkyl trialkyl ammonium carbonates.

16. The fuel performance additive of claim 13 , wherein the organic acid is selected from the group consisting of stearic acid, nonadecanoic acid, arachidic acid, tuberculostearic acid, tuzuic acid, petroselinic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, polyalkyl or polyalkenyl succinic ester acid, amide acid, imide acid, hexadecane diacid, heptadecane diacid, octadecane diacid, noncadecane diacid, eicosane diacid, 3-hexyl-4-decene-1,2-dicarboxylic acid, 3-hexyl-1,12-decanedicarboxylic acid, 6-ethylene-9-hexadecene-1,16-dicarboxylic acid, 6-ethyl-1,16-hexadecanedicarboxylic acid, 6-phenyl-1,12-dodecane dicarboxylic acid, 7,12-dimeth-y-7,1-octadecanediene-1,18-dicarboxylic acid, 7,12-dimeth-yl-1,18-octadecanedicarboxylic acid, 6,8-diphenyl-1,14-tetradecanedicarboxylic acid, and polyalkyl or polyalkenyl succinic diacids.

17. The fuel performance additive of claim 1 , wherein the quaternary ammonium salt is derived from an amido amine containing at least one tertiary amino group and an epoxide in the presence of a proton donor selected from a carboxylic acid and an alkyl phenol.

18. The fuel performance additive of claim 17 , wherein the amido amine is in a reaction medium substantially devoid of an acylating agent.

19. The fuel performance additive of claim 17 , wherein the proton donor is a carboxylic acid selected from the group consisting of fatty acids, formic acid, acetic acid, propionic acid, butyric acid, polyisobutenyl succinic acid, amide/acid, or acid/ester, and polymeric acids, and mixtures thereof.

20. A fuel composition including a major amount of a fuel and a fuel performance additive of claim 1 .

21. The fuel composition of claim 20 , wherein the fuel is selected from gasoline or diesel.

22. A method of improving the demulsibility of an additive-containing fuel, the method comprising:
combining a major amount of fuel with (a) a quaternary ammonium salt fuel performance additive and (b) a demulsifier component including a blend of (i) at least two alkoxylated phenol formaldehyde polymers including (i-1) a first alkoxylated phenol formaldehyde polymer having a relative solubility number of 18 to 22 and (i-2) a second alkoxylated phenol formaldehyde polymer having a relative solubility number of 12 to 16; (ii) an alkoxylated fatty acid polymer having a relative solubility number of 12 to 16; and (iii) an alkoxylated polyimine polymer having a relative solubility number of less than 10.

23. The method of claim 22 , wherein the fuel is selected from gasoline or diesel.

24. The method of claim 22 , wherein the improved demulsibility is measured per one of ASTM D1094, ASTM D7451, or combinations thereof.

25. The fuel performance additive of claim 1 , wherein the alkoxylated polyimine polymer is obtained from polyalkylene imines reacted with alkylene oxides selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide, cyclohexane oxide, or combinations thereof.

26. The method of claim 1 , wherein the alkoxylated polyimine polymer is obtained from polyalkylene imines reacted with alkylene oxides selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide, cyclohexane oxide, or combinations thereof.

Assignees

• Afton Chemical Corp
• Croda Inc

Inventors

• Taylor Daniel
• Tabibi Makaye

Classifications

• Y02E50/10

  Biofuels, e.g. bio-diesel · CPC title

• C10L2200/0446

  Diesel · CPC title

• C10L2200/0423

  Gasoline · CPC title

• C10L10/18 Primary

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