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US 2019/0382360 A1Published application
Carboxy alkyl-ester anti-agglomerants for the control of natural gas hydrates
AssigneeEcolab USA Inc.
InventorsJeff Michael Servesko, Jeremy Wayne Bartels, Regan Andrew Jones, Corbin Metoyer
Life of this patent
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Abstract
This disclosure relates to anti-agglomerant low dosage hydrate inhibitors that can inhibit the formation of hydrate agglomerants and/or plugs. Thus, provided herein are carboxy alkyl ester compounds that can be used in hydrate inhibitor compositions and methods of inhibiting formation of hydrate agglomerants in a fluid comprising water, a gas, and optionally a liquid hydrocarbon. Also provided herein are methods of making the carboxy alkyl ester compound.
Claims56
A compound of formula (I), or an acid, a free base, a zwitterion, or a salt thereof having the following structure:
- wherein
- RA and RB are independently a bond or a C1-C4 alkylene group;
- R1 and R5 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or alkylaryl wherein each group can optionally be substituted with an amine, an ester, an alkoxy, a hydroxyl, a halo, or a carboxyl group, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or alkylaryl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, an ether, an amide, or an ester group;
- R2 and R3 are independently hydrogen, alkyl, alkenyl, or alkynyl, wherein each group can optionally be substituted with an amine, a hydroxyl, or a carboxyl, and wherein each alkyl, alkenyl, or alkynyl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, an ether, an amide, or an ester group, or R2 and R3 together with the nitrogen they are attached to form a ring;
- R4 is hydrogen or alkyl;
- provided that at least one of R1 and R5 is hydrogen when the other is other than hydrogen, and when R2 and R3 together with the nitrogen they are attached to do not form a ring, at least one of R2 or R3 is a straight or branched alkyl or alkenyl group, wherein at least one of the —CH2— groups is replaced by an amine or an ether group.
3 more elements
A method of making a compound of formula (I):
- the method comprising contacting an alcohol corresponding in structure to formula (II):
- R1—OH Formula (II)
- or
- R5—OH Formula (II′)
- with an acid anhydride of formula (III) to produce an intermediate:
- and contacting the intermediate with an amine corresponding in structure to formula (IV):
- to produce a compound corresponding in structure to formula (I), wherein
- RA is a bond or a C1-C4 alkylene group;
- RB is a bond, a double bond, or a C1-C4 alkylene group;
- R1 and R5 are independently hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, or alkylaryl, wherein each group can optionally be substituted with an amine, a hydroxyl, or a carboxyl, and wherein each alkyl, alkenyl, alkynyl, cycloalkyl, or alkylaryl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, an ether, an amide, or an ester group;
- R2 and R3 are independently hydrogen, alkyl, alkenyl, or alkynyl, wherein each alkyl, alkenyl, or alkynyl group can optionally be substituted with an amine, a hydroxyl, or a carboxyl, and wherein each alkyl, alkenyl, or alkynyl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, an ether, an amide, or an ester group;
- or R2 and R3 together with the nitrogen they are attached to form a ring;
- and
- R4 is hydrogen, alkyl, alkenyl, or alkynyl;
- provided that at least one of R1 and R5 is hydrogen when the other is other than hydrogen and when R2 and R3 together with the nitrogen they are attached to do not form a ring, at least one of R1, R2, R3, and R5 is a straight or branched alkyl or alkenyl group, wherein at least one of the —CH2— groups is replaced by an amine or an ether group.
12 more elements
A compound having a structure corresponding to formula (V):
- wherein
- R2 and R3 are independently alkyl, alkenyl, or alkynyl, wherein each alkyl, alkenyl, or alkynyl group can optionally be substituted with an amine, a hydroxyl, or a carboxyl, and wherein each alkyl, alkenyl, or alkynyl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, or an ether group;
- R4 is hydrogen or alkyl;
- and
- R8 is alkyl or alkenyl, wherein each group can optionally be substituted with an amine, a hydroxyl, or a carboxyl, and wherein each alkyl or alkenyl group can optionally have one or more —CH2— groups replaced with an amine, a carbonyl, an ether, an amide, or an ester group;
- and
- n is an integer from 0 to 10.
4 more elements
Dependencies are inferred from the claim text.