IP Library Granted Patent US 10,876,033
Granted Patent B2
US 10,876,033 · App. 15/571,444 · Granted Dec 29, 2020

Nitrogen-containing anti-agglomerants for preserving the fluidity of fluids containing gas hydrates

Inventors: Hans Oskarsson (Stenungsund, SE); Ingemar Uneback (Svenshogen, SE)
Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
C09K8/52C09K8/54C10L3/107F17D1/17F17D3/12C09K2208/22
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Quick Facts
Patent No.
US 10,876,033
App. No.
15/571,444
Granted
Dec 29, 2020
Kind
B2
Abstract

The present invention relates to the use of a specific group of acylated nitrogen-containing compounds as anti-agglomerants for gas hydrates. The anti-agglomerants are surface active nitrogen-containing compounds with 1-7 nitrogen atoms, which compounds have at least two hydrophobic groups with 6-24 carbon atoms, and where the hydrophobic groups are connected to the remainder of the molecule by an amine moiety or an amide moiety, and which compounds have at least one C2-C5 acyl group; or a salt thereof. The invention also relates to a method for inhibiting the agglomeration of gas hydrates in a conduit, and compositions comprising the gas hydrate anti-agglomerant, a corrosion inhibitor and/or a paraffin deposition inhibitor.

Claims (10)

1. A method for inhibiting agglomeration of gas hydrates formed in a mixture including hydrocarbons and water, the method comprising:

preparing a surface-active nitrogen-containing compound having the following general formula I

wherein R is H or a hydrocarbyl group having 2-24 carbon atoms, G is a hydrocarbyl group having 6-24 carbon atoms or E, whereby R and G are selected such that the compound has at least one hydrocarbyl group with 6-24 carbon atoms connected to a nitrogen atom; each E is independently H, CH3, —CH2CH3 or an acyl group —C(═O)Ri, wherein each —C(═O)R 1 is independently the acyl group having 2-24 carbon atoms; provided that at least one of the —C(═O)R 1 groups is the acyl group having 2-5 carbon atoms, and at least one —C(═O)R 1 is an acyl group having 6-24 carbon atoms; and provided that when both R is H, then there are at least two of —C(═O)R 1 that are the acyl group having 6-24 carbon atoms; m is 2 or 3; and a is a number from 1 to 3;

whereby in formula I E is selected such that the compound contains 2-7 amide groups, as an anti-agglomerant for gas hydrates; and

adding the surface-active nitrogen-containing compound to the mixture to inhibit agglomeration of the gas hydrates.

2. The method according to claim 1 wherein the anti-agglomerant has formula I, wherein a=2, m=2 and R=H; the groups, and wherein two of the groups E are the acyl groups having 6-24 carbon atoms and one E is the acyl group having 4 carbon atoms.

3. The method according to claim 1 wherein the anti-agglomerant has formula I, wherein a=3, m=2 and R=H; the group, and wherein two of the groups E are the acyl groups having 6-24 carbon atoms, one E is the acyl group having 2 carbon atoms and one E is the acyl group having 4 carbon atoms.

4. The method according to claim 1 wherein the anti-agglomerant has formula I, wherein a=1, m=3 and one R is the hydrocarbyl group having 8-24 carbon atoms; wherein G is E, and wherein one of E is the acyl group having 6-24 carbon atoms, one of E is the acyl group having 4 carbon atoms and one of E is the acyl group having 2 carbon atoms.

5. The method according to claim 1 wherein the anti-agglomerant has formula I, wherein a=1, m=3 and one R is the hydrocarbyl group having 8-24 carbon atoms; wherein G is E, and wherein one of E is the acyl group having 6-24 carbon atoms and two of E are the acyl groups having 4 carbon atoms.

6. The method according to claim 1 wherein the anti-agglomerant has formula I, wherein a=2, m=3 and one R is the hydrocarbyl group having 8-24 carbon atoms; wherein G is the hydrocarbyl group having 8-24 carbon atoms, and wherein G and R are situated on the same carbon atom; and two of E are the acyl groups having 4 carbon atoms and one of E is the acyl group having 2 carbon atoms.

Assignments (3)
CHANGE OF NAME Recorded Sep 18, 2019
From: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: NOURYON CHEMICALS INTERNATIONAL B.V.
Reel/Frame 050426/0671 →
SECURITY INTEREST Recorded Oct 1, 2018
From: STARFRUIT US MERGER SUB 1 LLC; STARFRUIT US MERGER SUB 2 LLC; AKZO NOBEL SURFACE CHEMISTRY LLC; AKZO NOBEL CHEMICALS B.V.; AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
To: WILMINGTON TRUST (LONDON) LIMITED, AS COLLATERAL AGENT
Reel/Frame 047231/0001 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 6, 2017
From: OSKARSSON, HANS; UNEBACK, INGEMAR
To: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
Reel/Frame 044036/0409 →
Priority Claims (1)
EP 15167153 · May 11, 2015 · regional
Continuity (1)
Related Publication 20190119553A1 · Apr 25, 2019