# US 10,767,119 B1 · Amphiphilic asphaltene ionic liquids as demulsifiers for heavy petroleum crude oil-water emulsions

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- Number: US 10,767,119 B1
- Document ID: US10767119B1
- Status: Granted
- Kind: B1
- Application number: 16/750,041
- Filed: 2020-01-23
- Granted: 2020-09-08
- Earliest claimed: 2020-01-23
- Assignees: King Abdulaziz University
- Applicants: King Abdulaziz University
- Inventors: Ali Issa Ismail; Ayman Mohamady Atta; Mohamed Hassan El-Newehy; Mohamed E. El-Hefnawy
- Web page: https://patentgrep.com/patent/US10767119B1

## CPC

- C10G 33/04: with chemical means
- B01D 11/0292: {Treatment of the solvent}
- B01D 17/047: {with separation aids}
- C07C 7/20: Use of additives, e.g. for stabilisation
- C07D 495/22: in which the condensed system contains four or more hetero rings
- C10G 2300/206: Asphaltenes
- C10G: CRACKING HYDROCARBON OILS; PRODUCTION OF LIQUID HYDROCARBON MIXTURES, e.g. BY DESTRUCTIVE HYDROGENATION, OLIGOMERISATION, POLYMERISATION (cracking to hydrogen or synthesis gas C01B; cracking or pyrolysis of hydrocarbon gases to individual hydrocarbons or mixtures thereof of definite or specified constitution C07C; cracking to cokes C10B); RECOVERY OF HYDROCARBON OILS FROM OIL-SHALE, OIL-SAND, OR GASES; REFINING MIXTURES MAINLY CONSISTING OF HYDROCARBONS; REFORMING OF NAPHTHA; MINERAL WAXES
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Provided herein are amphiphilic asphaltene ionic liquids and methods of making and using the amphiphilic asphaltene ionic liquids, e.g. as demulsifiers for petroleum crude oil-water emulsions.

## Claims

### Claim 1

A method of demulsifying a petroleum crude oil-water emulsion, comprising
combining a first petroleum crude oil-water emulsion with a quantity of an amphiphilic asphaltene ionic liquid sufficient to demulsify the first petroleum crude oil-water emulsion,
wherein the amphililic asphaltene ionic liquid is or comprises an asphaltene quaternary alkylaminopyridinium cation with one or more different organic anionic salts, and
wherein the amphililic asphaltene ionic liquid is made by either
a) oxidizing one or more alkyl chains on a periphery of asphaltene molecules to form asphaltene carboxylic acids (ACA),
converting carboxylic acid groups to acid chlorides forming asphaltene acid chlorides (As—COCl), and
reacting the As—COCl with one or more quaternized ethoxylated alkyl pyridinium salts,
or
b) reacting the asphaltene with malic anhydride to form asphaltene malic anhydride adducts (AMA) which have one or more carboxylic acids on a periphery of the AMA molecules,
converting carboxylic acid groups to acid chlorides forming asphaltene acid chlorides (As—COCl), and
reacting the As—COCl with one or more quaternized ethoxylated alkyl pyridinium salts,
or
c) reacting the asphaltene with malic anhydride to form asphaltene malic anhydride adducts (AMA) which have one or more carboxylic acids on a periphery of the AMA molecules, and
reacting the AMA molecules with one or more quaternized ethoxylated alkyl pyridinium salts.

### Claim 2 (depends on 1)

The method of claim 1 wherein the one or more quaternized ethoxylated alkyl pyridininum salt is or comprises a quaternized ethoxylated alkyl pyridinium cation and an anion selected from Br, CH3COO, OCN, (H2PO4), HSO4, SCN, NO3, PF6, BF4, HCO3 and (CF3SO2)2N anions.

### Claim 3 (depends on 1)

The method of claim 1 wherein the one or more quaternized ethoxylated alkyl pyridininum salt is or comprises a quaternized ethoxylated alkyl pyridinium bromide (QEAP).

### Claim 4 (depends on 1)

The method of claim 1 wherein the process of a) or b) is used and the converting step is performed with thionyl chloride (SOCl2).

### Claim 5 (depends on 1)

The method of claim 1 wherein the process of c) is used and the reacting the AMA molecules comprises one or more of esterification or amidation being performed with a carbodiimide crosslinking reagent.

### Claim 6 (depends on 5)

The method of claim 5 wherein the carbodiimide crosslinking reagent is 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC).

### Claim 7 (depends on 1)

The method of claim 1, further comprising using the amphiphilic asphaltene ionic liquid from the first petroleum crude oil-water emulsion to demulsify a second petroleum crude oil-water emulsion.