Multiple charged ionic compounds derived from polyamines and compositions thereof and use thereof as reverse emulsion breakers in oil and gas operations

Patent metadata

Field	Value
Publication number	US-11685709-B2
Application number	US-201916554935-A
Country	US
Kind code	B2
Filing date	Aug 29, 2019
Priority date	Aug 29, 2018
Publication date	Jun 27, 2023
Grant date	Jun 27, 2023

Abstract

Disclosed herein is a novel class of multiple charged cationic or anionic compounds that are derived from an aza-Michael Addition reaction between a polyamine (Michael donor) and an activated olefin (Michael acceptor), methods of making the same, and use thereof. Also disclosed herein are the methods of using multiple charged cationic or anionic compounds disclosed herein in a reverse emulsion breaker composition to break reverse emulsion commonly found in a produced fluid in oil and gas operations. The disclosed REB methods or compositions are found to be more effective than those methods or compositions including commonly used for oil/solid and water separation.

First claim

What is claimed is:

1. A method of synthesizing a multiple charged cationic compound, comprising:
contacting a polyamine with an activated olefin having an ionic group to generate a compound;
wherein the polyamine is diethylenetriamine, triethylenetetramine, pentaethylenehexamine, hexaethyleneheptamine, tris(2-aminoethyl)amine, tetraethylenepentamine, polyethyleneeimine, or a combination thereof,
wherein the activated olefin is (3-acrylamidopropyl)trimethylammonium chloride (APTAC), [3-(methacryloylamino)propyl]trimethylammonium chloride (MAPTAC), 2-(acryloyloxy)-N,N,N-trimethylethanaminium chloride (DMAEA-MCQ), N,N-dimethylaminoethyl acrylate benzyl chloride quaternary salt (DMAEA-BCQ), or 2-(methacryloyloxy)-N,N,N-trimethylethan-1-aminium methyl sulfate (DMAEA-MSQ), or a combination thereof,
wherein the polyamine and activated olefin undergo an aza-Michael addition reaction; and
wherein the multiple charged cationic compound is a compound according to the structures:

wherein k is an integer of 1-1000; wherein l, m, n, o, or p are each an integer of 0-100 provided that at least one of l, m, n, o, or p is an integer of at least 1; X is NH or O; R 2 is H, CH 3 , or an unsubstituted, linear or branched C 2 -C 10 alkyl group; R 3 is absent or an unsubstituted, linear or branched C 1 -C 30 alkylene group; Y is —NR 4 R 5 R 6(+) or a salt thereof; R 4 , R 5 , and R 6 are independently a C 1 -C 10 alkyl group or benzyl group.

2. The method according to claim 1 , wherein the contacting step is done in the presence of a reaction solvent, of a reaction solvent and alkalinity source, of a reaction solvent and acid, or of a reaction solvent and a catalyst.

3. The method according to claim 2 , wherein the reaction solvent is water, methanol, ethanol, propanol, glycol, PEG, or a mixture thereof.

4. The method according to claim 1 , wherein the contacting step is done in the presence of a reaction solvent and in the absence of an alkalinity source, an acid, and a catalyst.

5. The method according to claim 1 , wherein the multiple charged cationic compound is one or more of;

6. The method of claim 2 , wherein the catalyst comprises an amidine, guanidine, ionic liquid, or a combination thereof.

7. The method of claim 1 , wherein the contacting of the polyamine and the activated olefin occurs at room temperature.

8. The method of claim 7 , further comprising a step of increasing the temperature to between 80° C. and 140° C.

9. The method of claim 8 , wherein the increasing of the temperature results in >98% consumption of the activated olefin.

10. The method of claim 1 , wherein a composition comprising the multiple charged cationic compound does not experience precipitation or phase separation for a period of between about 1 hour to about 2 years.

11. The method of claim 1 , wherein the multiple charged cationic compound is:

wherein k=1-1000.

Assignees

• Ecolab Usa Inc

Inventors

• Dhawan Ashish
• Monk Keith A
• Silvernail Carter M

Classifications

• C07C237/10 Primary

  having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups · CPC title

• C07C231/12

  by reactions not involving the formation of carboxamide groups · CPC title

• C09K8/584

  characterised by the use of specific surfactants · CPC title

• C07C229/16

  to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids · CPC title

• C07C227/04

  Formation of amino groups in compounds containing carboxyl groups · CPC title