Reaction products of alkenyl succinimides with ethylenediamine carboxy acids as fuel detergents

• US 4,971,598 A
• Filed: 03/22/1990
• Issued: 11/20/1990
• Est. Priority Date: 08/30/1988
• Status: Expired due to Term

• Current Assignee: Mobil Oil Corporation (Exxon Mobil Corporation)
• Original Assignee: Mobil Oil Corporation (Exxon Mobil Corporation)
• Inventors: Ashjian, Henry H., Hills, Frederick J., Andress, Harry J.
• Primary Examiner(s): Chaudhuri, Olik
• Assistant Examiner(s): McAvoy, Ellen
• Application Number:
  US07/497,368
• Time in Patent Office: 243 Days
• Field of Search: 44/71, 44/57, 548/546, 548/547
• US Class Current: 44/330
• CPC Class Codes: C10L 1/221 compounds of uncertain formula; reaction products where mixtures of compounds are obtained
• CPC Class Codes: F02B 3/06 with compression ignition compression ignition engines using air or gas for blowing fuel into compressed air in cylinder F02B13/02

Abstract

An additive for fuel compositions. The additive comprises the reaction product of an alkenyl succinimide selected from the group consisting of mono-succinimides, bis-succinimides, and mixtures thereof, with iminodiacetic acid or an ethylenediamine carboxy acid. The reaction product finds particular utility as a fuel detergent.

Claims

1. An additive for diesel fuel compositions comprising the reaction product of an alkenyl succinimide selected from the group consisting of mono-succinimides of the structural formula:

##STR5## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, bis-succinimides of the structural formula;

##STR6## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, and mixtures thereof, with iminodiacetic acid or an ethylenediamine carboxylic acid having the structural formula;

##STR7## wherein R², R³, R⁴, R⁵, are each a a ##STR8## group where R⁶ is 0 to 3 carbon atoms in number, said reaction product formed by reacting between about 1 mole and about 30 moles of said alkenyl succinimide with 1 mole of said ethylene diamine carboxylic acid or imino-diacetic acid at a temperature of between about 100°

C. and about 250°

C. and at a pressure from about atmospheric to about 100 psig.

2. The reaction product of claim 1 wherein R¹ is derived from a mixture of alpha olefins.

3. The reaction product of claim 1 wherein R¹ is derived from polybutenyl olefins.

4. The reaction product of claim 1 wherein the ethylenediamine carboxylic acid is ethylenediaminetetraacetic acid and the ratio of alkenyl succinimide reactant to ethylenediaminetetraacetic acid is between about 1 to about 10 moles of alkenyl succinimide reactant to one mole of ethylenediaminetetraacetic acid.

6. The reaction product of claim 1 wherein the duration of the reaction is between about 1 and 6 hours.

5. An additive for diesel fuel compositions comprising the reaction product of an alkenyl succinimide selected from the group consisting of mono-succinimides of the structural formula:

##STR9## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, bis-succinimides of the structural formula;

##STR10## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, and mixtures thereof, with an ethylenediamine carboxylic acid selected from the group consisting of ethylenediaminetriacetic acid and ethylenediaminetetraacetic acid, said reaction product formed by reacting between about 1 mole and about 30 moles of said alkenyl succinimide with 1 mole of said ethylenediamine carboxylic acid at a temperature of between about 100°

C. and about 250°

C. and at a pressure from about atmospheric to about 100 psig.

7. The diesel fuel additive of claim 5 wherein R¹ is derived from a mixture of alpha olefins.

8. The diesel fuel additive of claim 5 wherein R¹ is derived from polybutenyl olefins.

9. The diesel fuel additive of claim 5 wherein the ethylenediamine carboxylic acid is ethylenediaminetetraacetic acid.

10. The diesel fuel additive of claim 5 wherein the duration of the reaction is between about 1 and 6 hours.

11. A diesel fuel composition comprising a diesel fuel and between about 10 and about 300 pounds per 1000 barrels of diesel fuel of an additive for diesel fuel compositions comprising the reaction product of an alkenyl succinimide selected from the group consisting of mono-succinimides of the structural formula:

##STR11## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, bis-succinimides of the structural formula;

##STR12## wherein the number of carbon atoms in R¹ is from between about 12 to about 50, R is an alkylene containing 1 to 5 carbon atoms and n is from 1 to 10, with an ethylenediamine carboxylic acid selected from the group consisting of ethylenediaminetriacetic acid and ethylenediaminetetraacetic acid, said product formed by reacting between about 1 mole and about 30 moles of said alkenyl succinimide with 1 mole of said ethylenediamine carboxylic acid at a temperature of between about 100°

C. and about 250°

C. and at a pressure from about atmospheric to about 100 psig.

12. The diesel fuel composition of claim 11 wherein R¹ is derived from a mixture of alpha olefins.

13. The diesel fuel composition of claim 11 wherein R¹ is derived from polybutenyl olefins.

14. The diesel fuel composition of claim 11 wherein the ethylenediamine carboxylic acid is ethylenediaminetetraacetic acid.

15. The diesel fuel composition of claim 11 wherein the duration of the reaction is between about 1 and 6 hours.