Oxazolidines derived from polyalkyl or polyalkenyl n-hydroxyalkyl succinimides, obtainment process and use

Patent metadata

Field	Value
Publication number	US-9981958-B2
Application number	US-59606208-A
Country	US
Kind code	B2
Filing date	Apr 15, 2008
Priority date	Apr 18, 2007
Publication date	May 29, 2018
Grant date	May 29, 2018

Abstract

Oxazolidines, a process for producing the oxazolidines, and use as additives for fuels to prevent and control deposits in internal combustion engines are disclosed. The oxazolidines are derived from polyalkyl or polyalkenyl N-hydroxyalkyl succinimides and have the structural formula

wherein:
R is a polyakyl or polyalkenyl group having an average molecular weight ranging from 450 to 5000 daltons; m is an integer between 1 and 5; n is an integer between 0 and 1; and R 1 , R 2 , R 3 , and R 4 are independent radicals, represented by the groups: —H, —CH 2 (CH 2 ) A B, —C 6 H 3 DE or —C 10 H 4 FG; wherein:
A is an integer between 0 and 8, B is a group selected among —H, —NH 2 , —OH, —COOH, and D, E, F, and G are independent radicals, selected among the groups: —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 (CH 2 ) 2 CH 3 , —(CH 3 ) 3 , C 6 H 5 , —NH 2 , —OH, —OCH 3 , OCH 2 CH 2 OH, OCH(CH 3 )CH 2 OH, OC 6 H 5 —COOH, and —SO 3 .

First claim

That which is claimed is:

1. An ash less detergent/dispersant additive formulation comprising an oxazolidine derived from polyalkenyl N-hydroxyalkyl succinimides as a main active component, and an inert organic solvent, said oxazolidine having the formula:

wherein:
R is a polyalkenyl group having an average molecular weight ranging from 450 to 5000 daltons;
m is an integer between 1 and 5;
n is an integer between 0 and 1; and
R 1 , R 2 are H, R 3 , and R 4 are independent radicals, represented by the groups: —H, —CH 2 (CH 2 ) A B, —C 6 H 3 DE or —C 10 H 4 FG; wherein:
A is an integer between 0 and 8,
B is a group selected among —H, —NH 2 , —OH, —COOH, and
D, E, F, and G are independent radicals selected among the groups: —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 (CH 2 ) 2 CH 3 , —(CH 3 ) 3 , C 6 H 5 , —NH 2 , —OH, —OCH 3 , OCH 2 CH 2 OH, OCH(CH 3 )CH 2 OH, OC 6 H 5 —COOH, —SO 3 ,
wherein said additive formulation inhibits precipitation and disperses heavy organic compounds in gasoline.

2. The ash less detergent/dispersant additive formulation derived from polyalkenyl N-hydroxyalkyl succinimides according to claim 1 , wherein group R is a polyisobutylene derivative having an average molecular weight ranging from 450 to 5000 daltons.

3. The ash less detergent/dispersant additive formulation derived from polyalkenyl N-hydroxyalkyl succinimides according to claim 1 , wherein the substituents R 3 and R 4 are derived from a 2-(aminoalkylamino)-2,3-disubstituted-alcohol.

4. The ash less detergent/dispersant additive formulation derived from polyalkenyl N-hydroxyalkyl succinimides according to claim 1 , wherein the sum of m and n is an even number.

5. A process to obtain the oxazolidines derived from polyalkenyl N-hydroxyalkyl succinimides and paraformaldehyde from claim 1 , represented by the following synthesis pathway:

which consists of two reaction stages:
1) The first reaction stage comprises reacting a polyalkylene succinic anhydride having the formula I with a 2-(aminoalkylamino)-2,3-disubstituted-alcohol having the formula II to obtain the corresponding polyalkenyl N-hydroxyalkyl succinimide having the structural formula III,
II) The second reaction stage comprises reacting the corresponding polyalkenyl N-hydroxyalkyl succinimides of formula III with paraformaldehyde to obtain the corresponding oxazolidines derived from polyalkenyl N-hydroxyalkyl succinimides having the structural formula V.

6. A process of synthesis according to claim 5 , where, the polyalkyl or polyalkenyl N-hydroxyalkyl succinimide to paraformaldehyde molar ratio is 1:1.

7. A process of synthesis according to claim 6 , wherein the reaction is carried out in the bulk substance without a solvent.

8. A process of synthesis according to claim 6 , wherein the time of reaction is one half hour.

9. A process of synthesis according to claim 6 , wherein the reaction temperature 140° C.

10. A process of synthesis according to claim 6 , wherein the pressure at which the reaction is carried out is 585 mmHg.

11. A method of preventing or reducing build-up of organic deposits in an internal combustion engine using gasoline, said method comprising adding an oxazolidine to the gasoline at concentrations ranging from 50 to 2000 ppm, wherein said oxazolidines is derived from polyalkenyl N-hydroxyalkyl succinimides and paraformaldehyde and has the structural formula:

wherein:
R is a polyalkenyl group having an average molecular weight ranging from 450 to 5000 daltons;
m is an integer between 1 and 5;
n is an integer between 0 and 1; and
R 1 , R 2 are H, R 3 , and R 4 are independent radicals, represented by the groups: —H, —CH 2 (CH 2 ) A B, —C 6 H 3 DE or —C 10 H 4 FG; wherein:
A is an integer between 0 and 8,
B is a group selected among —H, —NH 2 , —OH, —COOH, and
D, E, F and G are independent radicals selected from the group consisting of —H, —CH 3 , —CH 2 CH 3 , —CH 2 CH 2 CH 3 , —CH 2 (CH 2 ) 2 CH 3 , —(CH 3 ) 3 , —C 6 H 5 , —NH 2 , —OH, —OCH 3 , OCH 2 CH 2 OH, —OCH(CH 3 )CH 2 OH, —OC 6 H 5 —COOH and —SO 3 .

12. The method according to claim 11 , wherein said oxazolidines are added to the gasoline as a concentrate in inert organic solvents having a boiling within the range of 75 to 200° C., selected from the group consisting of mixtures of xylenes, o-xylene, m-xylene, and p-xylene, branched and non-branched aliphatic alcohols containing from 3 to 10 carbon atoms and mixtures of aromatic solvents with branched and non-branched aliphatic alcohols, where said concentrate contains 10 to 90 wt. % of said oxazolidine.

13. The method according to claim 11 , wherein said gasoline further contains polyether compounds having fluidizing properties.

14. The method according to claim 13 , wherein the fluidizing compounds are used in the hydrocarbon fuel at concentrations ranging from 10 to 1,000 ppm.

15. The method according to claim 14 , wherein the ratio of fluidizing compounds to oxazolidines ranges from 1:10 to 10:1.

16. The process according to claim 5 , wherein the reactions are carried out in the bulk substance without a solvent.

17. The process according to claim 5 , wherein the time of reaction ranges from 0.5 to 1 hour.

18. The process according to claim 5 , wherein the reaction temperature ranges from 140° C.

19. The oxazolidines of claim 1 , wherein R is a polyisobutylene derivative having an average molecular weight of 450 to 2300 Daltons.

20. The oxazolidines of claim 1 , wherein R 3 is C 6 H 3 DE or C 10 H 4 FG.

21. The oxazolidines of claim 1 , wherein R 4 is C 6 H 3 DE or C 10 H 4 FG.

22. The method of claim 11 , wherein said oxazolidine is added in an amount of 75 to 500 ppm based on the amount of the gasoline.

Assignees

• Zamudio Rivera Luis Silvestre
• Flores Oropeza Eugenio Alejandro
• Lozada Y Cassou Marcelo
• Beltran Conde Hiram Isaac
• Buenrostro Gonzalez Eduardo
• Douda Youri
• Guzman Vega Mario Alberto
• Morales Pacheco Adela
• Mena Cervantes Violeta Yasmin
• Hernandez Altamirano Raul
• Mexicano Inst Petrol

Inventors

• Zamudio Rivera Luis Silvestre
• Flores Oropeza Eugenio Alejandro
• Lozada Y Cassou Marcelo
• Beltran Conde Hiram Isaac
• Buenrostro Gonzalez Eduardo
• Douda Youri
• Morales Pacheco Adela
• Mena Cervantes Violeta Yasmin
• Hernandez Altamirano Raul

Classifications

• C10L10/04

  for minimising corrosion or incrustation · 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

• C07D413/06 Primary

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title