Mild steel corrosion inhibitor compounds

Patent metadata

Field	Value
Publication number	US-9758878-B2
Application number	US-201414525513-A
Country	US
Kind code	B2
Filing date	Oct 28, 2014
Priority date	Oct 28, 2014
Publication date	Sep 12, 2017
Grant date	Sep 12, 2017

Abstract

Compounds and methods of inhibiting corrosion of mild steel. Compounds disclosed herein are cationic and contain multiple functional motifs such as propargyl, cinnamaldehyde, isoxazolidine and hydrophobe. These compounds are found to be effective in inhibiting mild steel corrosion in HCl, H 2 SO 4 , NaCl and CO 2 -saturated environments.

First claim

The invention claimed is:

1. A compound for inhibiting corrosion of mild steel having the following Formulas I or II:

wherein:
R 1 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 haloalkyl, substituted or unsubstituted C 2-12 alkenyl, substituted or unsubstituted C 2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted heterocycloalkyl;
R 2 is selected from the group consisting of substituted or unsubstituted, branched or linear, C 1-22 alkyl, substituted or unsubstituted C 1-22 haloalkyl, substituted or unsubstituted C 2-22 alkenyl and substituted or unsubstituted C 2-22 alkynyl;
R 3 is selected from the group consisting of substituted or unsubstituted C 1-12 aldehyde, substituted or unsubstituted acrylic acid, substituted or unsubstituted propanol and substituted or unsubstituted propenal;
R 4 is selected from the group consisting of substituted or unsubstituted, branched or linear, C 2-22 alkynyl; and
X is selected from the group consisting of fluoride, chloride, bromide and iodide.

2. The compound of claim 1 , wherein the compound is selected from the group consisting of:
p-9-(2-methylisoxazolidin-5-yl)undec-1-yloxybenzaldehyde;
p-9-(2-methylisoxazolidin-5-yl)non-1-yloxycinnamaldehyde; and
p-9-[2-methyl-2-(2-popyn-1-yl) isoxazolidinium-5-yl]non-1-yloxycinnamaldehyde chloride.

3. The compound of claim 1 , wherein the compound is prepared with a method comprising the following steps:
(a) alkylating an arylaldehyde with a haloalkene to form a haloaryl alkene; and
(b) cycloadding a nitrone to the haloaryl alkene to form an isoxazolidine.

4. The compound of claim 3 , wherein the method further comprises the following steps:
(c) contacting isoxazolidine with an acid to form an acid derivative; and
(d) reducing then oxidizing the acid derivative to form a substituted cinnamaldehyde.

5. The compound of claim 4 , wherein the method further comprises the following step:
(e) quaternizing a nitrogen atom in the substituted cinnamaldehyde with a haloalkyne to form a quaternary salt.

6. The compound of claim 1 , wherein the compound is effective in inhibiting corrosion of mild steel surrounded by an environment containing at least one acidic fluid, at least one neutral salt or combinations thereof.

7. The compound of claim 6 , wherein the acidic fluid is selected from the group consisting of HCl, H 2 SO 4 , HNO 3 , CO 2 and HS.

8. The compound of claim 6 , wherein the acidic fluid is present at a saturated concentration.

9. The compound of claim 1 , wherein the compound is effective in inhibiting corrosion of mild steel at concentrations of 10 to 1000 parts by the total weight of fluids that are in contact with the mild steel.

10. A composition for inhibiting corrosion of mild steel comprising a compound having the following Formulas I or II and at least one other additive:

wherein:
R 1 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 haloalkyl, substituted or unsubstituted C 2-12 alkenyl, substituted or unsubstituted C 2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted heterocycloalkyl;
R 2 is selected from the group consisting of substituted or unsubstituted, branched or linear, C 1-22 alkyl, substituted or unsubstituted C 1-22 haloalkyl, substituted or unsubstituted C 2-22 alkenyl and substituted or unsubstituted C 2-22 alkynyl;
R 3 is selected from the group consisting of substituted or unsubstituted C 1-12 aldehyde, substituted or unsubstituted acrylic acid, substituted or unsubstituted propanol and substituted or unsubstituted propenal;
R 4 is selected from the group consisting substituted or unsubstituted, branched or linear, C 2-22 alkynyl; and
X is selected from the group consisting of fluoride, chloride, bromide and iodide.

11. The composition of claim 10 , wherein the compound is selected from the group consisting of:
p-9-(2-methylisoxazolidin-5-yl)undec-1-yloxybenzaldehyde;
p-9-(2-methylisoxazolidin-5-yl)non-1-yloxycinnamaldehyde; and
p-9-[2-methyl-2-(2-popyn-1-yl) isoxazolidinium-5-yl]non-1-yloxycinnamaldehyde chloride.

12. The composition of claim 10 , wherein the compound is effective in inhibiting corrosion of mild steel surrounded by an environment containing at least one acidic fluid, at least one neutral salt or combinations thereof.

13. The composition of claim 10 , wherein the acidic fluid is selected from the group consisting of HCl, H 2 SO 4 , HNO 3 , CO 2 and H 2 S.

14. The composition of claim 10 , wherein the acidic fluid is present at a saturated concentration.

15. The composition of claim 10 , wherein the compound is effective in inhibiting corrosion of mild steel at concentrations of 10 to 1000 parts by the total weight of fluids that are in contact with the mild steel.

16. A method of inhibiting the corrosion of mild steel, comprising contacting the mild steel with a composition comprising a compound having the following Formulas I or II and at least one other additive:

wherein:
R 1 is selected from the group consisting of hydrogen, substituted or unsubstituted C 1-12 alkyl, substituted or unsubstituted C 1-12 haloalkyl, substituted or unsubstituted C 2-12 alkenyl, substituted or unsubstituted C 2-12 alkynyl, substituted or unsubstituted aryl, substituted or unsubstituted cycloalkyl, substituted or unsubstituted heteroaryl, substituted or unsubstituted heterocycloalkyl, substituted or unsubstituted arylalkyl, substituted or unsubstituted heteroarylalkyl, substituted or unsubstituted cycloalkyl, and substituted or unsubstituted heterocycloalkyl;
R 2 is selected from the group consisting of substituted or unsubstituted, branched or linear C 1-22 alkyl, substituted or unsubstituted C 1-22 haloalkyl, substituted or unsubstituted C 2-22 alkenyl and substituted or unsubstituted C 2-22 alkynyl;
R 3 is selected from the group consisting of substituted or unsubstituted C 1-12 aldehyde, substituted or unsubstituted acrylic acid, substituted or unsubstituted propanol and substituted or unsubstituted propenal;
R 4 is selected from the group consisting of substituted or unsubstituted, branched or linear, C 2-22 alkynyl; and
X is selected from the group consisting of fluoride, chloride, bromide and iodide.

17. The method of claim 16 , wherein the compound is selected from the group consisting of:
p-9-(2-methylisoxazolidin-5-yl)undec-1-yloxybenzaldehyde;
p-9-(2-methylisoxazolidin-5-yl)non-1-yloxycinnamaldehyde; and
p-9-[2-meth

Assignees

• Univ King Fahd Pet & Minerals

Inventors

• Ali Shaikh Asrof
• Jafar Mazumder Mohammad Abu
• Al-Muallem Hasan Ali

Classifications

• C23F11/04 Primary

  in markedly acid liquids · CPC title

• C07D261/02

  not condensed with other rings · CPC title

• C07C45/71

  being hydroxy groups · CPC title

• C23F11/141

  Amines; Quaternary ammonium compounds · CPC title

• C23F11/149

  Heterocyclic compounds containing nitrogen as hetero atom · CPC title