Back to results
US 7,517,447 B2Granted
Sterically hindered N-methylsecondary and tertiary amine sulfur scavengers and methods for making and using same
AssigneeClearwater International, LLC
InventorLarry W. Gatlin
Life of this patent
Estimating the term…
Abstract
An new class of oil-soluble, sulfur scavengers or converts are disclosed where the scavengers include substantially monomeric aldehyde-amine adducts from the reaction of at least one sterically hindered primary or secondary amine and a molar excess of at least one aldehyde. Methods are also disclosed for reducing, reducing below a given level or eliminating noxious sulfur species from fluids using the inventive scavengers and for making the inventive scavengers.
Claims33
A method comprising the step of:
- contacting a fluid including noxious sulfur-containing species with an effective amount of a sulfur scavenging composition comprising substantially monomeric aldehyde-amine adducts formed from a reaction of a molar excess of at least one aldehyde or aldehyde donor and at least one secondary amine or a primary amine having at least one sterically bulk substituent so that the adducts are substantially compounds derived from the reaction of a single aldehyde and a single amine so that the resulting adducts comprise amines bonded to three different groups where two of the groups can be a part of a ring structure and characterized by compounds of formulas (I), (II) or mixtures thereof:
- CH2R—NR1R2 (I)
- CH2R—R4NR3NR5—CH2R (II)
- where R is a hydrogen atom (H) or a carbon-containing group, R1 and R2 are the same or different, at least one being a sterically hindered carbon-containing group having between 3 and about 24 carbon atoms or R1 and R2 can form a ring system, R3 is a divalent sterically hindered carbon-containing group, R4 and R5 are the same or different and are H or a CH2R group, provided that both R4 and R5 are not H and where one or more of the carbon atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by oxygen atoms in the form of ether moieties, nitrogen groups in the form of tertiary amine or amide moieties or mixtures thereof, and where one or more hydrogen atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by fluorine atoms, chlorine atoms or mixtures thereof,
- where the CH2R groups are derived from the at least one aldehyde of the formula R—CHO used in the reaction and where the effective amount is sufficient to reduce, to reduce below a target level or to substantially eliminate the noxious sulfur-containing species in the fluid.
2 more elements
A method comprising the step of:
- adding, to a fluid including noxious sulfur-containing compounds, an effective amount of a sulfur scavenging composition comprising substantially monomeric aldehyde-amine adducts formed from a reaction of a molar excess of an aldehyde or aldehyde donor and a secondary amine or a primary amine having at least one sterically bulk substituent so that the adducts are substantially compounds derived from the reaction of a single aldehyde and a single amine so that the resulting adducts comprise amines bonded to three different groups where two of the groups can be a part of a ring structure and are characterized by compounds of formulas (I), (II) or mixtures thereof:
- CH2R—NR1R2 (I)
- CH2R—R4NR3NR5—CH2R (II)
- where R is a hydrogen atom (H) or a carbon-containing group, R1 and R2 are the same or different, at least one being a sterically hindered carbon-containing group having between about 3 and about 24 carbon atoms or R1 and R2 can form a ring system, R3 is a divalent sterically hindered carbon-containing group, R4 and R5 are the same or different and are H or a CH2R group, provided that both R4 and R5 are not H and where one or more of the carbon atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by oxygen atoms in the form of ether moieties, nitrogen groups in the form of tertiary amine or amide moieties or mixtures thereof, and where one or more hydrogen atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by fluorine atoms, chlorine atoms or mixtures thereof,
- where the CH2R groups are derived from the at least one aldehyde of the formula R—CHO used in the reaction and where the effective amount is sufficient to reduce, to reduce below a target level or to substantially eliminate the noxious sulfur-containing species in the fluid.
2 more elements
A method comprising the step of:
- adding a fluid into a container;
- adding, prior to, after or concurrently, an effective amount of a sulfur scavenging composition comprising substantially monomeric aldehyde-amine adducts of a molar excess of at least one aldehyde or aldehyde donor with at least one secondary amine or a primary amine having at least one sterically bulk substituent so that the adducts are substantially compounds derived from the reaction of a single aldehyde and a single amine so that the resulting adducts comprise amines bonded to three different groups where two of the groups can be a part of a ring structure;
- and are characterized by compounds of formulas (I), (II) or mixtures thereof:
- CH2R—NR1 R2 (I)
- CH2R—R4NR3NR5—CH2R (II)
- where R is a hydrogen atom (H) or a carbon-containing group, R1 and R2 are the same or different, at least one being a sterically hindered carbon-containing group having between about 3 and about 24 carbon atoms or R1 and R2 can form a ring system, R3 is a divalent sterically hindered carbon-containing group, R4 and R5 are the same or different and are H or a CH2R group, provided that both R4 and R5 are not H and where one or more of the carbon atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by oxygen atoms in the form of ether moieties, nitrogen groups in the form of tertiary amine or amide moieties or mixtures thereof, and where one or more hydrogen atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by fluorine atoms, chlorine atoms or mixtures thereof,
- where the CH2R groups are derived from the at least one aldehyde of the formula R—CHO used in the reaction, and
- where amount is sufficient to reduce, reduce below a target level or substantially eliminating noxious sulfur-containing species in fluid.
5 more elements
A method comprising the step of:
- introducing into a downhole fluid an effective amount of a sulfur scavenging composition comprising substantially monomeric aldehyde-amine adducts of a molar excess of at least one aldehyde or aldehyde donor with at least one secondary amine or a primary amine having at least one sterically bulk substituent so that the adducts are substantially compounds derived from the reaction of a single aldehyde and a single amine so that the resulting adducts comprise amines bonded to three different groups where two of the groups can be a part of a ring structure;
- and are characterized by compounds of formulas (I), (II) or mixtures thereof:
- CH2R—NR1 R2 (I)
- CH2R—R4NR3NR5 —CH2R (II)
- where R is a hydrogen atom (H) or a carbon-containing group, R1 and R2 are the same or different, at least one being a sterically hindered carbon-containing group having between about 3 and about 24 carbon atoms or R1 and R2 can form a ring system, R3 is a divalent sterically hindered carbon-containing group, R4 and R5 are the same or different and are H or a CH2R group, provided that both R4 and R5 are not H and where one or more of the carbon atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by oxygen atoms in the form of ether moieties, nitrogen groups in the form of tertiary amine or amide moieties or mixtures thereof, and where one or more hydrogen atoms of R, R1, R2, R3, R4, R5 or mixtures thereof can be replaced by fluorine atoms, chlorine atoms or mixtures thereof,
- where the CH2R groups are derived from the at least one aldehyde of the formula R—CHO used in the reaction, and
- where amount is sufficient to reduce, reduce below a target level or substantially eliminating noxious sulfur-containing species in fluid.
4 more elements
Dependencies are inferred from the claim text.