# US 10,308,532 B2 · Method to treat flushing liquor systems in coke plants

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- Number: US 10,308,532 B2
- Document ID: US10308532B2
- Status: Granted
- Kind: B2
- Application number: 14/394,272
- Filed: 2012-04-18
- Published: 2015-02-26
- Granted: 2019-06-04
- Earliest claimed: 2012-04-18
- Assignees: Bl Technologies, Inc.
- Applicants: Guixi Zhang; Jason Zhao
- Inventors: Guixi Zhang; Jason Zhao
- Web page: https://patentgrep.com/patent/US10308532B2

## CPC

- C08F 220/34: Esters containing nitrogen {, e.g. N,N-dimethylaminoethyl (meth)acrylate}
- B01D 17/047: {with separation aids}
- C02F 1/5272: {using specific organic precipitants}
- C02F 1/547: {Tensides}
- C10G 9/005: {Coking (in order to produce liquid products mainly)}
- C10G 33/04: with chemical means
- C02F 2101/32: Hydrocarbons, e.g. oil
- C02F 2103/365: {from petrochemical industry (e.g. refineries)}
- C02F 2305/00: Use of specific compounds during water treatment
- C08F 220/56: Acrylamide; Methacrylamide
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- 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)
- C02F: TREATMENT OF WATER, WASTE WATER, SEWAGE, OR SLUDGE (separation in general B01D; special arrangements on waterborne vessels of installations for treating water, waste water or sewage, e.g. for producing fresh water, B63J; adding materials to water to prevent corrosion C23F; treating radioactively-contaminated liquids G21F9/04; regeneration of reactants for recirculation into processes, see the relevant places for the processes)
- 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

## Abstract

Methods are disclosed for reducing oil in water emulsions in coking processes. One exemplary method comprises: providing an aqueous stream with an oil in water emulsion; providing a treatment composition, wherein the treatment composition comprises at least one cationic polyacrylamide; and contacting the aqueous stream with the treatment composition.

## Claims

### Claim 1

A method of demulsifying an oil in water emulsion present in an aqueous stream of a coking process comprising:
passing said aqueous stream comprising an oil in water emulsion from an upstream to downstream direction to and through a decanter, wherein said oil in water emulsion comprises tars and other contaminants formed in a coking process; and
contacting said aqueous stream with a treatment composition prior to introducing said aqueous stream into the decanter of said coking process, said treatment composition comprising a cationic polyacrylamide copolymer and downstream from said decanter, contacting said aqueous stream with an ethoxylated surfactant in addition to, or instead of any surfactant present in said treatment composition, wherein said ethoxylated surfactant comprises at least one ethoxylated compound having the formula:
R—O—(CH2CH2O)n—H
where n is equal to or greater than about 20; and R is at least one chain of a branched alkyl phenol, a branched or linear fatty alcohol, a fatty acid alkanolamide, or a fatty acid, and
said cationic polyacrylamide copolymer comprising repeat units (x) and (y) of the formula
wherein R1 and R2 are the same or different and are chosen from H and CH3; Q is —C(O)O—, or —OC(O)—, or —C(O)NH—; R3 is branched or linear C1-C4 alkyl; R4, R5, and R6 are independently chosen from H, C1-C4 linear or branched alkyl, or a C5-C8 aromatic or alkylaromatic group; A is an anion selected from Cl−, Br−, HSO4−, or MeOSO3− wherein the molar ratio of repeat units (x):repeat units (y) is about 10:90 to about 40:60.

### Claim 2 (depends on 1)

The method of claim 1, wherein said repeat unit (y) comprises at least one member selected from the group consisting of dimethylaminoethyl (meth)acrylate methyl chloride quaternary salt, dimethylaminoethyl (meth)acrylate methyl sulfate quaternary salt, dimethylaminoethyl (meth)acrylate benzyl chloride quaternary salt, acrylamidopropyl trimethylammonium chloride, dimethylaminopropyl (meth)acrylamide methyl sulfate quaternary salt, diallyldiethylammonium chloride, and diallyldimethyl ammonium chloride.

### Claim 3 (depends on 2)

The method of claim 2, wherein:
said repeat unit (y) comprises dimethylaminoethyl (meth)acrylate methyl chloride quaternary salt; and
said repeat unit (x) comprises acrylamide.

### Claim 4 (depends on 3)

The method of claim 3, wherein a molar ratio of repeat units (x):repeat units (y) is about 20:80.

### Claim 5 (depends on 1)

The method of claim 1, wherein said treatment composition comprises about 0.01 ppm to about 1000 ppm by volume of said aqueous stream.

### Claim 6 (depends on 5)

The method of claim 5, wherein said treatment composition comprises from about 0.5 ppm to about 500 ppm by volume of said aqueous stream.

### Claim 7 (depends on 6)

The method of claim 6, wherein said treatment composition comprises from about 1 ppm to about 10 ppm by volume of said aqueous stream.

### Claim 8 (depends on 7)

The method of claim 7, wherein a concentration ratio in ppm of said ethoxylated surfactant to said cationic polyacrylamide copolymer in said treatment composition ranges from about 4:1 to about 1:4.

### Claim 9 (depends on 1)

The method of claim 1, wherein a concentration ratio in ppm of said ethoxylated surfactant to said cationic polyacrylamide copolymer in said treatment composition is about 2:1.5.

### Claim 10 (depends on 1)

The method of claim 1, wherein a concentration ratio in ppm of said ethoxylated surfactant to said cationic polyacrylamide copolymer in said treatment composition is about 2:1.

### Claim 11 (depends on 1)

The method as recited in claim 1, wherein said contaminants comprise ammonia, hydrophobic compounds, coal powder, coke powder, solids, or a combination thereof.

### Claim 12

A method of demulsifying an oil in water emulsion present in an aqueous stream of a coking process comprising:
passing said aqueous stream comprising an oil in water emulsion from an upstream to downstream direction to and through a decanter, wherein said oil in water emulsion comprises tars and other contaminants formed in a coking process; and
contacting said aqueous stream with a treatment composition prior to introducing said aqueous stream into the decanter of said coking process, said treatment composition comprising a cationic acrylamide copolymer and downstream from said decanter, contacting said aqueous stream with an ethoxylated surfactant in addition to, or instead of any surfactant present in said treatment composition, wherein said ethoxylated surfactant comprises at least one ethoxylated compound having the formula:
R—O—(CH2CH2O)n—H
where n is equal to or greater than about 20; and R is at least one chain of a branched alkyl phenol, a branched or linear fatty alcohol, a fatty acid alkanolamide, or a fatty acid, and
said cationic acrylamide copolymer comprising repeat units of (x) (meth)acrylamide and (y) quaternary ammonium salt; wherein said repeat unit (y) of said cationic acrylamide copolymer comprises a member selected from the group consisting of:
a) dimethylaminoethyl (meth)acrylate methyl chloride;
b) dimethylaminoethyl (meth)acrylate methyl sulfate;
c) dimethylaminoethyl (meth)acrylate benzyl chloride;
d) acrylamidopropyl trimethylammonium chloride;
e) dimethylaminopropyl (meth)acrylamide methyl sulfate;
f) diallyldiethyl ammonium chloride; and
g) diallyldimethylammonium chloride.

### Claim 13 (depends on 12)

The method as recited in claim 12, wherein said repeat unit (y) is dimethylaminoethyl (meth)acrylate quaternary ammonium salt and wherein the molar ratio of repeat units (x):repeat units (y) is from about 10:90 to about 40:60.

### Claim 14 (depends on 13)

The method as recited in claim 13, wherein said repeat unit (y) is dimethylaminoethyl (meth)acrylate methyl chloride.

### Claim 15 (depends on 14)

The method as recited in claim 14, wherein said molar ratio of repeat units (x):repeat units (y) is about 20:80.

### Claim 16 (depends on 15)

The method as recited in claim 15, further comprising contacting said aqueous stream with a sorbitan mono-oleate surfactant.

### Claim 17 (depends on 12)

The method as recited in claim 12, wherein said contaminants comprise ammonia, hydrophobic compounds, coal powder, coke powder, solids, or a combination thereof.