Corrosion inhibiting compositions including bis-imidazoline compounds derived from enriched linear tetramines

Patent metadata

Field	Value
Publication number	US-2016333484-A1
Application number	US-201415107741-A
Country	US
Kind code	A1
Filing date	Dec 12, 2014
Priority date	Dec 27, 2013
Publication date	Nov 17, 2016
Grant date	—

Abstract

The present invention provides corrosion inhibiting compositions that incorporate at least one bis-imidazoline compound. In the practice of the present invention, a tetramine admixture enriched with respect to linear tetramine is used to prepare the bis-imidazoline compound. “Enriched” means at least 70 weight percent and up to 100% of the tetramine species included in the admixture includes a linear tetramine such as L-TETA.

First claim

What is claimed is:

1 . A method of inhibiting corrosion of a substrate comprising a ferrous metal, the method comprising a step of contacting the ferrous metal with composition comprising a compound having the following structure:

wherein:
each Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 independently is H; a hydrocarbyl of 1 to 10 carbon atoms; and/or at least first and second of the Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 moieties are linked to each other in a manner effective to form a divalent moiety that attaches to the corresponding imidazoline ring(s) at two attachment sites; and
each R H independently is a hydrophobic, aliphatic, monovalent moiety comprising 6 to 50 carbon atoms.

2 . The method of claim 1 , wherein the composition further comprises at least one nonionic surfactant.

3 . The method of claim 2 , wherein the nonionic surfactant comprises (a) one or more hydrophilic polyalkylene oxide chains containing on average 2 to 100 alkylene oxide repeating units, and (b) one or more aromatic hydrophobic moieties.

4 . The method of claim 2 , wherein the nonionic surfactant has the structure

wherein R H is one or more hydrophobic, aliphatic moieties; R′ is a divalent alkylene moiety of 1 to 6 carbon atoms; and n is 2 to 100 on average.

5 . The method of claim 2 , wherein the nonionic surfactant is derived from one or more seed oils.

6 . The method of claim 2 , wherein the nonionic surfactant comprises one or more hydrophobic, branched, secondary alcohols that are functionalized with one or more hydrophilic alkylene oxide chains.

7 . The method of claim 1 , wherein each Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 is H.

8 . The method of claim 1 , wherein R H is unsaturated.

9 . The method of claim 1 , wherein the bis-imidazoline has the structure

10 . The method of claim 1 , wherein the linear tetramine is L-TETA.

11 . The method of claim 1 , wherein at least 95 weight percent of the at least one tetramine comprises the linear tetramine.

12 . A method of making a bis-imidazoline, comprising the steps of:
(a) providing an amine admixture comprising at least one tetramine, wherein at least 70 weight percent of the at least one tetramine comprises a linear tetraamine according to the following structure having first and second primary amine moieties and first and second secondary amine moieties:

(b) reacting the linear tetraamine with at least one co-reactive reactant according to the following structure that is monofunctional with respect to carboxylate functionality and that is co-reactive with a primary amine functionality to form an amide linkage:

said reacting occurring under conditions effective to form a bis-amide according to the following structure:

and
(c) causing ingredients comprising at least the bis-amide to form a bis-imidazoline according to the following structure:

wherein:
each Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 independently is H; a hydrocarbyl of 1 to 10 carbon atoms; and/or at least first and second of the Z 1 , Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 moieties are linked to each other in a manner effective to form a divalent moiety that attaches to the corresponding imidazoline ring(s) at two attachment sites;
M is a moiety such that the —COOM functionality of the co-reactive reactant is co-reactive with a primary amine functionality of the linear tetramine to form an amide linkage; and
each R H independently is a hydrophobic, aliphatic, monovalent moiety comprising 6 to 50 carbon atoms.

13 . The method of claim 12 , wherein step (c) occurs at a temperature in the range from 180° C. to 250° C. at a pressure below normal atmosphere.

14 . The method of claim 12 , wherein step (c) occurs at a temperature in the range from 180° C. to 250° C. at a pressure below 500 millibar.

15 . The method of claim 12 , wherein step (c) occurs at a temperature in the range from 180° C. to 250° C. at a pressure below 100 millibar.

Assignees

• Dow Global Technologies Llc

Inventors

• Gulabani Ritesh
• King Stephen W
• Tatake Prashant

Classifications

• C07D233/10

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring nitrogen atoms · CPC title

• C09D7/125

  Chemistry & Metallurgy · mapped topic

• C23F11/04

  in markedly acid liquids · CPC title

• C09D5/086

  Organic or non-macromolecular compounds · CPC title

• C23F11/149 Primary

  Heterocyclic compounds containing nitrogen as hetero atom · CPC title