Amino and imino propionic acids, process of preparation and use

Patent metadata

Field	Value
Publication number	US-10207983-B2
Application number	US-201414581778-A
Country	US
Kind code	B2
Filing date	Dec 23, 2014
Priority date	Jun 3, 2010
Publication date	Feb 19, 2019
Grant date	Feb 19, 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 process for producing N-alkenyl amino or imino propionic acids to obtain a corrosion inhibiting compound consisting of N-alkenyl amino or imino propionic acids having the formula III and IV from a reaction that takes place 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 an alkali metal or organic base in an amine-acid ratio of 0.5:3 to 3:0.5 to obtain the N-alkenyl amino or imino propionic acids of formula III and/or IV

the reaction being carried out at a temperature range of 90 to 100° C. and a reaction time between 1 and 10 hours by adding said compound of formula II in the absence of a solvent, in the absence of a base, and at atmospheric pressure, and then increasing the reaction temperature up to 160° C., where R is an alkenyl group having 1 to 30 carbon atoms, R 1 is H or —CH 3 and R 2 is H; and
removing unreacted amines by extraction with a hydrocarbon solvent to obtain said compounds III and IV.

2. The process according to claim 1 , wherein the compound of formula I is a linear or branched alkenyl amine selected from the group consisting of linoleylamine, eurocylamine, behenylamine and taloylamine.

3. The process according to claim 1 , wherein the compound of formula II is an alpha-beta unsaturated carboxylic acid is acrylic acid.

4. The process according to claim 1 , wherein the compound II is acrylic acid.

5. The process according to claim 1 , wherein the reaction time is between 2 to 8 hours.

6. The process according to claim 1 , where the hydrocarbon solvent is hexane.

7. The process of claim 1 , wherein said amine-acid-molar ratio is in the range of 1:2 to 2:1.

8. The process of claim 1 , wherein said process obtains a mixture of said compound of formula III and said compound of formula IV.

9. The process of claim 8 , wherein said process obtains a reaction product of 90% of said compound of formula III and 10% of said compound of formula IV.

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

• C10L2200/0446

  Diesel · CPC title

• C10L2200/043

  Kerosene, jet fuel · CPC title

• C10L2200/0423

  Gasoline · CPC title

• C10L10/04

  for minimising corrosion or incrustation · CPC title