IP Library Granted Patent US 11,124,693
Granted Patent B2
US 11,124,693 · App. 16/340,699 · Granted Sep 21, 2021

Hydroxyalkylurethane kinetic hydrate inhibitors

Inventors: John H. Clements (The Woodlands, TX); Marek Pakulski (The Woodlands, TX); David C. Lewis (The Woodlands, TX)
Assignee: Indorama Ventures Oxides LLC
C09K8/524C07D319/06
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Quick Facts
Patent No.
US 11,124,693
App. No.
16/340,699
Granted
Sep 21, 2021
Kind
B2
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 (20)

1. A composition comprising water, a crude hydrocarbon stream and a gas hydrate inhibitor composition comprising at least 99.5% by weight, based on the total weight of the gas hydrate inhibitor composition, of a hydroxyalkylurethane obtained by the reaction of an amine and an alkylene carbonate.

2. The composition of claim 1 , wherein the amine is a compound having the formula R 0 —(NH 2 ) n where R 0 is a linear or branched C 2 -C 20 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.

3. The composition of claim 1 , wherein the alkylene carbonate is a compound having a formula (9) or (10):

where R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are the same or different and are selected from hydrogen, a C 1 -C 6 alkyl and a C 1 -C 6 hydroxyalkyl.

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

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

6. 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.

7. 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.

8. A gas hydrate inhibitor composition comprising a kinetic hydrate inhibitor wherein the kinetic hydrate inhibitor is a hydroxyalkylurethane obtained by the reaction of

where R 0 is a linear or branched C 2 -C 20 alkyl group or a polyoxyalkylene chain derived from ethylene oxide, propylene oxide, butylene oxide or a mixture thereof,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different and are selected from hydrogen, a C 1 -C 6 alkyl and a C 1 -C 6 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.

9. The gas hydrate inhibitor composition of claim 8 , further comprising a second hydrate inhibitor or a solvent or an additive included for purposes other than gas hydrate inhibition.

10. The gas hydrate inhibitor composition of claim 9 , 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.

11. A composition comprising water, a crude hydrocarbon stream and a gas hydrate inhibitor composition comprising a hydroxyalkylurethane obtained by the reaction of

where R 0 is a linear or branched C 2 -C 20 alkyl group or a polyoxyalkylene chain derived from ethylene oxide, propylene oxide, butylene oxide or a mixture thereof,

R 2 , R 3 , R 4 , R 5 , R 6 , R 7 are the same or different and are selected from hydrogen, a C 1 -C 6 alkyl and a C 1 -C 6 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.

Assignments (2)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jan 20, 2020
From: HUNTSMAN PETROCHEMICAL LLC
To: INDORAMA VENTURES OXIDES LLC
Reel/Frame 051649/0173 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 22, 2019
From: CLEMENTS, JOHN H.; PAKULSKI, MAREK; LEWIS, DAVID C.
To: HUNTSMAN PETROCHEMICAL LLC
Reel/Frame 050136/0709 →