Amino and imino propionic acids, process of preparation and use

Patent metadata

Field	Value
Publication number	US-10167249-B2
Application number	US-201414563234-A
Country	US
Kind code	B2
Filing date	Dec 8, 2014
Priority date	Jun 3, 2010
Publication date	Jan 1, 2019
Grant date	Jan 1, 2019

Abstract

N-alkyl, N-alkenyl, N-cycloalkyl, N-aryl amino or imino propionic acids with an alkyl chain ranging from 6 to 18 carbons, or alkenyl chain from 8 to 30 carbons, are obtained from a reaction process in the absence of solvent at a temperature range from 30 to 180° C. and a time of 1 to 10 hours at atmospheric pressure. Formulations composed of N-alkyl or N-alkenyl or N-cycloalkyl or N-aryl amino or imino propionic acids, polyethers derived from propylene oxide or ethylene oxide or copolymer thereof and a solvent consisting of aromatic compounds such as toluene or xylene, diesel or gasoline or alcohols such as isopropanol and ethanol, or mixtures thereof, are obtained inhibit ferrous metal corrosion of pipelines and storage tanks and transport crude oil and liquid fuels. A method inhibiting corrosion of ferrous metals adds an effective amount of the corrosion inhibitor to a petroleum based material such as crude oil and liquid fuels such as gasoline, diesel fuel, and aviation fuel.

First claim

What is claimed is:

1. A corrosion inhibiting composition including a corrosion inhibiting compound consisting of N-alkenyl amine or imino propionic acid of structural formula:

where R is a linear or branched alkenyl chain having 1 to 30 carbon atoms, R1 is a radical represented by —H or —CH3 and R2 is —H.

2. A composition adapted for inhibiting corrosion of ferrous metals, said composition containing at least one N-alkenyl amino or imino propionic acid, wherein said amino or imino propionic acids are produced by a reaction process in the absence of solvent, in the absence of a base, and at atmospheric pressure, said process comprising reacting an alkyl, alkenyl, cycloalkyl or aromatic amine of formula I with an alpha-beta unsaturated carboxylic acid of formula II according to the following synthesis scheme (3) in the absence of a solvent and in the absence of a base to obtain the compounds of formula III and/or IV

the reaction being carried out at a temperature range of 50 to 180° C. and a reaction time between 1 and 10 hours, where R is a linear or branched alkyl or alkylene group having 1 to 30 carbon atoms, R1 is H or —CH3 and R2 is H.

3. The composition according to claim 2 , wherein the compound of formula II is an alpha-beta unsaturated carboxylic acid selected from the group consisting of acrylic acid and methacrylic acid.

4. The composition according to claim 2 , wherein the compound II is acrylic acid.

5. The composition according to claim 2 , wherein the amine-acid molar ratio is 0.5:3 to 3:0.5.

6. The composition according to claim 2 , wherein the reaction is carried out at a temperature range of 30° C. to 180° C.

7. The process composition to claim 2 , wherein the reaction time is between 1 and 10 hours.

8. The composition according to claim 2 , wherein the resulting amino or imino propionic acids are purified by extracting with a hydrocarbon solvent.

9. The composition according to claim 8 , where the hydrocarbon solvent is hexane.

10. A corrosion inhibiting formulation consisting essentially of:
a) N-alkenyl amino or imino propionic acids having the formula

where R is an alkenyl chain having 1 to 30 carbon atoms, R1 is a radical represented by —H or —CH3 and R2 is —H;
b) a polyether derived from propylene oxide or ethylene oxide or copolymer thereof in an amount of not more than 40% by weight based on the weight of the amino or imino propionic acid, and
c) a solvent consisting of aromatic compounds selected from the group consisting of toluene and xylene, and an alcohol selected from the group consisting of methanol, ethanol and isopropanol, gasoline, diesel, and mixtures thereof.

11. The corrosion inhibiting formulation according to claim 10 , where the concentration of N-alkenyl amino or imino propionic acids is in the range of 10% to 90% by weight.

12. The corrosion inhibiting formulation according to claim 10 , wherein the concentration of solvent used is in the range of 10% to 90% by weight based on the weight of the amine or imino propionic acid.

13. The corrosion inhibiting formulation according to claim 10 , wherein the solvent is xylene.

14. The formulation of claim 10 , wherein the weight average molecular weight polyether derived from propylene oxide or ethylene oxide or copolymer thereof is 100-3000 g/mol.

15. A corrosion inhibiting composition comprising:
at least one component selected from the group consisting of gasoline, jet fuel, MTBE, diesel fuel and alcohol; and
a corrosion inhibiting compound consisting of a compound of formula III or formula IV in an amount of 1 to 200 ppm to inhibit corrosion of ferrous metals in contact with said composition, wherein said compound is an N-alkenyl amino or imino propionic acid of structural formula:

where R is an alkenyl chain having 1 to 30 carbon atoms, R 1 is a radical represented by —H or —CH 3 and R 2 is H; and
a polyether derived from propylene oxide or ethylene oxide.

16. The composition of claim 15 , wherein
the compound of formula III or formula IV is present in an amount of 5 to 25 ppm.

17. The composition of claim 15 , wherein
the compound of formula III or formula IV is present in an amount of 25 to 100 ppm.

18. The composition of claim 15 , including a mixture of said compound of formula III and compound of formula IV.

19. The composition of claim 18 , wherein
said compound of formula IV and compound of formula III are present in a ratio of 90:10 by weight.

20. The composition of claim 19 , wherein
said compound of formula IV is 3,3′-(octadec-9 enylazanediyl) dipropionic acid and said compound of formula III is 3-(octadec-9-enylaminio) propionic acid.

21. The composition of claim 15 , wherein
said compound of formula III is selected from the group consisting of an N-alkenyl-amino propionic acid having an alkenyl group with 8-30 carbon atoms.

22. The composition of claim 15 , wherein
said compound of formula IV and is selected from the group consisting of N-alkenyl-imino propionic acid having an alkyl or alkenyl chain of 8-30 carbons.

23. The composition of claim 15 , wherein
said at least one corrosion inhibiting compound is selected from the group consisting of an N-alkenyl-amino propionic acid having an alkenyl group with 8-30 carbon atoms; and
at least one selected from the group consisting of an N-alkenyl-imino propionic acid having an alkenyl group with 8-30 carbon atoms.

24. The composition of claim 15 , wherein said amino or imino propionic acid is selected from the group consisting of 3,3′-(octadec-9 enylazanediyl)dipropanoic acid, 3-(octadec-9-enylamino)propanoic acid, 3,3′-(octadec-9 enylazanediyl)dipropanoic acid and 10% of the 3-(octadec-9-enylamino)propanoic acid, 3-(dodecylamino)propanoic acid, and mixtures thereof.

Assignees

• Mexicano Inst Petrol

Inventors

• Hernandez Altamirano Raul
• Zamudio Rivera Luis Silvestre
• Mena Cervantes Violeta Yasmin
• Beltran Conde Hiram Isaac
• Dominguez Aguilar Marco Antonio
• Martinez Viramontes Jaquelin
• Estrada Buendia Aristeo

Classifications

• C23F11/144 Primary

  Aminocarboxylic acids · CPC title

• C10L2200/0423

  Gasoline · CPC title

• C10L2230/14

  for improving storage or transport of the fuel · CPC title

• C10L1/223

  having at least one amino group bound to an aromatic carbon atom {(C10L1/221, C10L1/2227 take precedence)} · CPC title

• C10L2270/026

  for diesel engines, e.g. automobiles, stationary, marine · CPC title