# US 2019/0375979 A1 · Hydroxyalkylurethane Kinetic Hydrate Inhibitors

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- Number: US 2019/0375979 A1
- Document ID: US20190375979A1
- Status: Published application
- Kind: A1
- Application number: 16/340,699
- Filed: 2018-01-30
- Published: 2019-12-12
- Earliest claimed: 2017-02-28
- Assignees: Huntsman Petrochemical Corporation
- Applicants: Huntsman Petrochemical LLC
- Inventors: John H. Clements; Marek Pakulski; David C. Lewis
- Web page: https://patentgrep.com/patent/US20190375979A1

## CPC

- C09K 8/52: Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning
- C09K 8/524: organic depositions, e.g. paraffins or asphaltenes
- C07D 319/06: not condensed with other rings
- C09K 2208/22: Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present disclosure generally relates to hydroxyalkylurethanes obtained from the reaction of amines and alkylene carbonates and their use in gas hydrate inhibitor compositions to effectively inhibit gas hydrate formation in a crude hydrocarbon stream.

## Claims

### Claim 1

A composition comprising water, a crude hydrocarbon stream and a gas hydrate inhibitor composition comprising a hydroxyalkylurethane.

### Claim 2 (depends on 1)

The composition of claim 1, wherein the hydroxyalkylurethane is obtained by the reaction of an amine and an alkylene carbonate.

### Claim 3 (depends on 2)

The composition of claim 2, wherein the amine is a compound having the formula R0—(NH2)n where R0 is a linear or branched C2-C20 alkyl group or a polyoxyalkylene chain derived from ethylene oxide, propylene oxide, butylene oxide or a mixture thereof, and n is an integer from 1 to 3.

### Claim 4 (depends on 2)

The composition of claim 2, wherein the alkylene carbonate is a compound having a formula (9) or (10):
where R2, R3, R4, R5, R6 and R7 are the same or different and are selected from hydrogen, a C1-C6 alkyl and a C1-C6 hydroxyalkyl.

### Claim 5 (depends on 1)

The composition of claim 1, wherein the hydroxyalkylurethane is obtained by the reaction of
where R0 is a linear or branched C2-C20 alkyl group or a polyoxyalkylene chain derived from ethylene oxide, propylene oxide, butylene oxide or a mixture thereof,
R2, R3, R4, R5, R6, R7 are the same or different and are selected from hydrogen, a C1-C6 alkyl and a C1-C6 hydroxyalkyl,
n is an integer from 1 to 3 and
r and s are integers from 1 to 3 with the proviso that r+s=n.

### Claim 6 (depends on 1)

The composition of claim 1, wherein the crude hydrocarbon stream is a crude natural gas stream.

### Claim 7 (depends on 1)

The composition of claim 1, wherein the crude hydrocarbon stream is a crude petroleum stream.

### Claim 8 (depends on 1)

The composition of claim 1, wherein the gas hydrate inhibitor composition further comprises a second hydrate inhibitor or a solvent or an additive included for purposes other than gas hydrate inhibition.

### Claim 9 (depends on 1)

The composition of claim 1, wherein the hydroxyalkylurethane is present in an amount of from about 0.005% by weight to about 8% by weight, based on the total weight of water in the composition.

### Claim 10

A method for inhibiting formation of gas hydrates comprising contacting a crude hydrocarbon stream comprising water and one or more lower hydrocarbons or other hydrate forming compound with a gas hydrate inhibitor composition comprising a hydroxyalkylurethane.

### Claim 11 (depends on 10)

The method of claim 10, wherein the hydroxyalkylurethane is obtained by the reaction of an amine and an alkylene carbonate.

### Claim 12 (depends on 11)

The method of claim 11, wherein the amine is a compound having the formula R0—(NH2), where R0 is a linear or branched C2-C20 alkyl group or a polyoxyalkylene chain derived from ethylene oxide, propylene oxide, butylene oxide or a mixture thereof, and n is an integer from 1 to 3.

### Claim 13 (depends on 12)

The method of claim 12, wherein the alkylene carbonate is a compound having a formula (9) or (10):
where R2, R3, R4, R5, R6 and R7 are the same or different and are selected from hydrogen, a C1-C6 alkyl and a C1-C6 hydroxyalkyl.

### Claim 14 (depends on 10)

The method of claim 10, wherein the contacting occurs by injection or mixing with a static mixer.

### Claim 15 (depends on 10)

The method of claim 10, wherein the crude hydrocarbon stream and gas hydrate inhibitor composition are contacted at a pressure at or greater than atmospheric pressure.

### Claim 16 (depends on 15)

The method of claim 15, wherein the crude hydrocarbon stream and gas hydrate inhibitor composition are contacted at a temperature at or lower than ambient temperature.

### Claim 17

A gas hydrate inhibitor composition comprising a kinetic hydrate inhibitor wherein the kinetic hydrate inhibitor is a hydroxyalkylurethane.

### Claim 18 (depends on 17)

The gas hydrate inhibitor composition of claim 17, further comprising a second hydrate inhibitor or a solvent or an additive included for purposes other than gas hydrate inhibition.

### Claim 19 (depends on 18)

The gas hydrate inhibitor composition of claim 18, wherein the second hydrate inhibitor is selected from the group consisting of: a thermodynamic inhibitor, a kinetic hydrate inhibitor, an agglomeration inhibitor and a mixture thereof.