2-mercaptobenzimidazole derivatives as corrosion inhibitors

• US 10,457,817 B2
• Filed: 05/02/2017
• Issued: 10/29/2019
• Est. Priority Date: 05/02/2016
• Status: Active Grant

• Current Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Original Assignee: Ecolab USA Incorporated (Ecolab, Inc.)
• Inventors: Ekoue-Kovi, Kekeli, Tomar, Neetu, Jadhav, Deepak, Peyton, Kim B., Sorrells, Jennifer L., Jones, Ian Michael
• Primary Examiner(s): Godenschwager, Peter F
• Assistant Examiner(s): Oyer, Andrew J.
• Application Number:
  US15/584,489
• Publication Number:
  US 20170313891A1
• Time in Patent Office: 910 Days
• CPC Class Codes: C07D 235/28 Sulfur atoms
• CPC Class Codes: C09D 5/086 Organic or non-macromolecular compounds
• CPC Class Codes: C09D 7/63 organic
• CPC Class Codes: C10L 1/2443 heterocyclic compounds
• CPC Class Codes: C10L 1/2456 sulfur with oxygen and/or nitrogen in the ring, e.g. thiazoles
• CPC Class Codes: C10L 10/04 for minimising corrosion or incrustation
• CPC Class Codes: C10L 2200/0423 Gasoline
• CPC Class Codes: C10L 2200/0446 Diesel
• CPC Class Codes: C10L 2270/023 for gasoline engines
• CPC Class Codes: C10L 2270/026 for diesel engines, e.g. automobiles, stationary, marine
• CPC Class Codes: C23F 11/10 using organic inhibitors
• CPC Class Codes: C23F 11/16 Sulfur-containing compounds
• CPC Class Codes: C23F 11/165 Heterocyclic compounds containing sulfur as hetero atom

Abstract

The present invention generally relates to methods and compounds for preventing metal corrosion. More specifically, the method comprises contacting a hydrocarbon-containing liquid with a composition in an effective amount to prevent metal corrosion.

Claims

1. A method for preventing metal corrosion, the method comprising contacting an effective amount of an anticorrosion composition with a hydrocarbon-containing liquid, the hydrocarbon-containing liquid being in contact with a metal, the anticorrosion composition comprising a solvent and a compound of Formulae I or II:

2. The method of claim 1, wherein R⁵ is other than hydrogen.

3. The method of claim 1, wherein the metal is silver, copper, or a combination thereof.

4. The method of claim 1, wherein R¹, R², and R⁴ are independently substituted alkyl wherein one or more of the —

CH₂—

groups is replaced with a —

C(O)—

, or —

O—

, or one or more of the carbon atoms of the alkyl group is substituted with an amine group.

5. The method of claim 4, wherein R¹, R², and R⁴ are independently —

(CHR²²)_n—

NR²⁰R²¹, wherein n is an integer from 1 to 4, R²⁰ and R²¹ are independently alkyl, and R²² is hydrogen or hydroxy.

6. The method of claim 5, wherein R²⁰ and R²¹ are independently butyl, pentyl, hexyl, heptyl, octyl, isopropyl, 2-ethyl hexyl, sec-butyl, or sec-pentyl.

8. The method of claim 1, wherein the compound of Formulae I or II is selected from the group consisting of:

9. The method of claim 1, wherein the solvent comprises an aromatic solvent, an aliphatic solvent, a nitrogen-containing solvent, a glycol solvent, or a combination thereof.

10. The method of claim 9, wherein the aromatic solvent comprises heavy aromatic naphtha, toluene, kerosene, diesel, gasoline, reformate, or a combination thereof;

the aliphatic solvent comprises hexane, heptane, octane, or a combination thereof;

the nitrogen-containing solvent comprises N,N-dimethylformamide, 2-ethylhexylamine, or a combination thereof; and

the glycol solvent comprises triglyme, diglyme, hexylene glycol, or a combination thereof.

11. The method of claim 1, wherein the anticorrosion composition further comprises a compound of Formulae III or IV:

12. The method of claim 11, wherein R¹¹ is

13. The method of claim 11, wherein the compound of Formulae III or IV is selected from the group consisting of:

14. The method of claim 11, wherein a compound of Formulae I or II and a compound of Formulae III or IV are present in the anticorrosion composition at a concentration of from 5 to 30 wt. %, and 30 to 5 wt. % respectively, based on the total weight of the formulation.

15. The method of claim 11, wherein the anticorrosion composition is contacted to the hydrocarbon-containing liquid at a concentration from about 1 ppm to about 100 ppm.

16. The method of claim 1, wherein the hydrocarbon-containing liquid comprises gasoline, diesel, naphtha, jet fuel, kerosene, or a combination thereof.

7. The method of 1, wherein R³ and R⁵ are independently hydrogen or unsubstituted C₁ to C₆ alkyl.

17. A method for preventing metal corrosion, the method comprising contacting an effective amount of an anticorrosion composition with a hydrocarbon-containing liquid, the hydrocarbon-containing liquid being in contact with a metal, the anticorrosion composition comprising a solvent and a compound of Formula IIA:

18. The method of claim 17, wherein R⁷ and R⁸ are independently hydrogen or unsubstituted C₁ to C₆ alkyl.

19. The method of claim 17, wherein R⁷ and R⁸ are hydrogen.