Mannich detergents for hydrocarbon fuels

Patent metadata

Field	Value
Publication number	US-9783752-B2
Application number	US-63920006-A
Country	US
Kind code	B2
Filing date	Dec 15, 2006
Priority date	Dec 15, 2006
Publication date	Oct 10, 2017
Grant date	Oct 10, 2017

Abstract

New, highly effective substantially pure Mannich detergents for use in hydrocarbon fuels reduce engine deposits in spark and compression ignition internal combustion engines. The Mannich condensation reaction products are obtainable by reacting: (i) a polyamine having primary amino groups, (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted at in a molar ratio of (i):(ii):(iii) of approximately 1:2:3. The Mannich detergent compounds may be dispersed in a liquid carrier to provide a fuel additive concentrate for hydrocarbon engine fuels which effectively control engine deposit formation in intake valves, port fuel injectors and combustion chambers.

First claim

What is claimed is:

1. A fuel additive composition, comprising
(a) a substantially pure Mannich reaction product obtained by reacting (i) 1,2-diaminocyclohexane (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted using a molar ratio of (i):(ii):(iii) of approximately 1:2:3 to provide the substantially pure Mannich reaction product having a purity of at least about 80%; and
(b) a liquid carrier.

2. The fuel additive composition according to claim 1 , wherein the hydrocarbyl-substituted hydroxyaromatic compound comprises ortho-cresol, or phenol, or mixture of o-cresol and phenol, having an aliphatic hydrocarbyl substituent derived from a polyolefin having an average molecular weight in the range of about 300 to about 2000.

3. The fuel additive composition according to claim 2 , wherein the aliphatic hydrocarbyl substituent comprises polyisobutylene.

4. The fuel additive composition according to claim 1 , wherein the carrier is selected from the group consisting of liquid poly-a-olefin oligomers, liquid polyalkene hydrocarbons, liquid hydrotreated polyalkene hydrocarbons, mineral oils, liquid poly(oxyalkylene) compounds, and any mixture thereof.

5. A fuel additive composition, comprising
(a) a Mannich reaction product obtained by reacting (i) 1,2-diaminocyclohexane (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted using a molar ratio of (i):(ii):(iii) of approximately 1:2:3 such that said polyamine (i) is reactable with said hydrocarbyl-substituted hydroxyaromatic compound (ii) so as to obtain said substantially pure intermediate, said intermediate being reactable with said aldehyde (iii) to obtain said Mannich reaction product as a substantially pure product having a purity of at least about 80%;
(b) a liquid carrier.

6. A substantially pure Mannich reaction product obtained by reacting (i) 1,2-diaminoocyclohexane (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted using a molar ratio of (i):(ii):(iii) of approximately 1:2:3 such that said polyamine (i) is reactable with said hydrocarbyl-substituted hydroxyaromatic compound (ii) so as to obtain said substantially pure intermediate, said substantially pure intermediate being reactable with said aldehyde (iii) to obtain said substantially pure Mannich reaction product having a purity of at least about 80%.

7. The substantially pure Mannich reaction product according to claim 6 , wherein the hydrocarbyl-substituted hydroxyaromatic compound comprises ortho-cresol, or phenol, or mixture of o-cresol and phenol, having an aliphatic hydrocarbyl substituent derived from a polyolefin having an average molecular weight in the range of about 300 to about 2000.

8. The substantially pure Mannich reaction product according to claim 6 , wherein said aldehyde is selected from the group consisting of furfural, thiophene aldehyde, paraformaldehyde, and formalin.

9. A fuel composition for an internal combustion engine comprising (a) in a major amount, a spark-ignitable combustible hydrocarbon fuel; and a minor amount of a fuel additive containing a Mannich reaction product according to claim 6 in a carrier fluid.

10. A fuel composition for an internal combustion engine, comprising
(a) in major amount, a spark-ignitable combustible hydrocarbon fuel; and
(b) in minor amount, a fuel additive composition comprising a substantially pure Mannich reaction product obtained by reacting (i) 1,2-diamino cyclohexane, (ii) a hydrocarbyl-substituted hydroxyaromatic compound, and (iii) an aldehyde, wherein the reaction is conducted using a molar ratio of (i):(ii):(iii) of approximately 1:2:3 to provide the substantially pure Mannich reaction product having a purity of at least about 80%; and wherein the Mannich reaction product is present in an amount sufficient to reduce the weight amount of engine deposits in an internal combustion engine operated on the fuel composition.

11. The fuel composition of claim 10 , comprising the fuel additive composition in an amount ranging from about 100 to about 1,000 ppm.

12. The fuel composition of claim 10 , further comprising at least one additive selected from the group consisting of antioxidants, carrier fluid, demulsifying agents, rust or corrosion inhibitors, metal deactivators, combustion modifiers, alcohol co-solvents, octane improvers, emission reducers, friction modifiers, lubricity additives, ancillary detergent/dispersant additives, biocides, antistatic additives, drag reducing agents, dehazers, anti-knock additives, anti-icing agents, anti-valve seat recession additives, combustion improvers, markers, and dyes.

13. A method of controlling engine deposits in an internal combustion engine comprising operating said engine with said fuel composition of claim 9 .

14. The fuel additive composition according to claim 1 , wherein the substantially pure Mannich reaction product has a purity of at least about 90%.

15. The fuel additive composition according to claim 14 , wherein the substantially pure Mannich reaction product has a purity of at least about 95%.

16. The fuel additive composition according to claim 5 , wherein the substantially pure product has a purity of at least about 90%.

17. The fuel additive composition according to claim 16 , wherein the substantially pure product has a purity of at least about 95%.

18. The substantially pure Mannich reaction product according to claim 6 , wherein the purity is at least about 90%.

19. The substantially pure Mannich reaction product according to claim 18 , wherein the purity is at least about 95%.

20. The fuel composition according to claim 10 , wherein the substantially pure Mannich reaction product has a purity of at least about 90%.

21. The fuel composition according to claim 20 , wherein the substantially pure Mannich reaction product has a purity of at least about 95%.

22. The fuel additive composition according to claim 1 , wherein the substantially pure Mannich reaction product includes a tertiary amine.

23. The method of controlling engine deposits in an internal combustion engine according to claim 13 , wherein the substantially pure Mannich reaction product provides improved intake valve deposit performance and improved port fuel injector performance when used in the fuel composition compared to a fuel composition which does not contain the substantially pure Mannich reaction product.

Assignees

• Malfer Dennis J
• Thomas May D
• Afton Chemical Corp

Inventors

• Malfer Dennis J
• Thomas May D

Classifications

• C10L1/1985

  polyethers, e.g. di- polygylcols and derivatives; ethers - esters · CPC title

• C10L1/2475

  obtained otherwise than by reactions only involving unsaturated carbon to carbon bonds · CPC title

• C10L1/221

  compounds of uncertain formula; reaction products where mixtures of compounds are obtained · CPC title

• C10L1/143 Primary

  mixtures of organic macromolecular compounds with organic non-macromolecular compounds · CPC title

• C10L1/238

  obtained otherwise than by reactions involving only carbon-to-carbon unsaturated bonds {(C10L1/221 takes precedence)} · CPC title