# US 9,518,231 B2 · Demulsifying and dehydrating formulations for heavy crude oils based on block copolymers bifunctionalized with amines

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- Number: US 9,518,231 B2
- Document ID: US9518231B2
- Status: Granted
- Kind: B2
- Application number: 14/338,941
- Filed: 2014-07-23
- Published: 2014-11-13
- Granted: 2016-12-13
- Earliest claimed: 2008-12-10
- Assignees: Instituto Mexicano Del Petroleo
- Applicants: Instituto Mexicano Del Petroleo
- Inventors: Gabriel Cendejas Santana; Eugenio Alejandro Flores Oropeza; Laura Veronica Castro Sotelo; Aristeo Estrada Buendia; Marcelo Lozada y Cassou; Flavio Salvador Vazquez Moreno
- Web page: https://patentgrep.com/patent/US9518231B2

## CPC

- C10G 33/04: with chemical means
- C08G 65/2624: {containing aliphatic amine groups}
- C08G 65/2627: {containing aromatic or arylaliphatic amine groups}
- C08G 65/263: {containing heterocyclic amine groups}
- C08G 65/33306: {acyclic}
- C08G 65/33317: {heterocyclic}
- C08L 71/02: Polyalkylene oxides
- C08G 2650/50: containing nitrogen, e.g. polyetheramines or Jeffamines(r)
- C08G 2650/58: Ethylene oxide or propylene oxide copolymers, e.g. pluronics
- 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
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

The present invention relates to demulsifying and dehydrating formulations of heavy crude oil based block copolymers amine bifunctionalized with low polydispersities. These formulations can contain solvents whose boiling point is in the range from 35 to 200° C., preferably: dichloromethane, chloroform, toluene, xylenes, turbosine, naphtha or mixtures thereof.

## Claims

### Claim 1

An amine bifunctionalized block copolymer of the formula 5a and 5b, having a molecular weight within the average range between 800 and 4000 Daltons
where
w and y numbers are in the range of 10 to 60;
R1 and R2 radicals are independently selected from the group consisting of
—H; —CH2(CH2)AH; —CEGJ; —CH2CHL(OH); —CH2(CH2)QOH;
where A is a number between 1 and 9,
E, G and J are independently a radical selected from the group consisting of: —H, methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl,
L is a radical represented by methyl or ethyl,
Q is a number between 1 and 5, T is selected from the group consisting of —H, methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl, NO2, Cl, F and Br, and
where:
U is a number between 1 and 2;
X is represented by atoms of oxygen and nitrogen, when X is nitrogen then V is represented by, -methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl phenyl, cyclohexyl, cyclopentyl, benzyl;
Z is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl, benzyl and hydroxyl.

### Claim 2 (depends on 1)

The amine bifunctionalized block copolymer according to claim 1, having a polydispersity in the range from 1.02 to 1.50.

### Claim 3 (depends on 1)

The amine bifunctionalized block copolymer according to claim 1, wherein R1 and R2 of formula (5a) are independently a linear or branched aliphatic group, or a mono or disubstituted aromatic group.

### Claim 4 (depends on 1)

The amine bifunctionalized block copolymer according to claim 1, wherein the amine groups of formula (5a) and formula (5b) are 5 or 6 cyclic groups which contain an oxygen or nitrogen and have 1 or 2 substituents in any position.

### Claim 5 (depends on 1)

The amine bifunctionalized block copolymer according to claim 1, wherein the amine group of formula (5a) and formula (5b) is selected from the group consisting of 2-alkyl-amino-alcohol and a mono or disubstituted aromatic group.

### Claim 6

A formulation comprising at least one amine bifunctionalized block copolymer formula 5a or 5b at a concentration of 5 to 50% by weight, in a solvent having a boiling point of 35 to 200° C., wherein said amine bifunctionalized block copolymer has the formula 5a and 5b, and has an average molecular weight within the range between 800 and 4000 Daltons
where:
w and y are an independent integer in the range of 10 to 60 to provide an average molecular weight of 800 to 4000 Daltons;
R1 and R2 are radicals independently selected from the group consisting of
—H; —CH2(CH2)AH; —CEGJ; —CH2CHL(OH); —CH2(CH2)QOH;
where A is an integer between 1 and 9,
E, G and J are independently a radical selected from the group consisting of: —H, methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl,
L is a radical selected from the group consisting of methyl or ethyl,
Q is an integer between 1 and 5, T is selected from the group consisting of —H, methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl, NO2, Cl, F and Br,
where:
U is a number between 1 and 2,
X is an atom selected from the group consisting of oxygen and nitrogen, when X is nitrogen then V is selected from the group consisting of -methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl phenyl, cyclohexyl, cyclopentyl, and benzyl, and
Z is selected from the group consisting of methyl, ethyl, n-propyl, iso-propyl, sec-butyl, iso-butyl, tert-butyl, n-butyl, phenyl, cyclohexyl, cyclopentyl, benzyl and hydroxyl.

### Claim 7 (depends on 6)

The formulation of claim 6, wherein the formulation includes said copolymer in an amount of 5 to 40% by weight.

### Claim 8 (depends on 6)

The formulation of claim 6, wherein said solvent is selected from the group consisting of dichloromethane, chloroform, benzene, toluene, xylenes, turbosine, naphtha, and mixtures thereof.