Multiple hydrophilic head hydrate inhibitors

Patent metadata

Field	Value
Publication number	US-9796906-B2
Application number	US-201414765460-A
Country	US
Kind code	B2
Filing date	May 5, 2014
Priority date	May 5, 2014
Publication date	Oct 24, 2017
Grant date	Oct 24, 2017

Abstract

Compounds comprising multiple hydrophilic heads and a lipophilic tail may be employed into fluids to inhibit agglomeration of hydrates, among other things. Suitable hydrophilic heads may include secondary, tertiary, and/or quaternary ammonium cation moieties, phosphonium cation moieties, and combinations thereof. Such LDHI compounds may provide enhanced interactivity with hydrate crystals and/or hydrate-forming molecules. These compounds may be employed in fluids in various environments, such as a conduit penetrating a subterranean formation, or a conduit carrying fluid in an industrial setting.

First claim

What is claimed is:

1. A method comprising:
introducing a composition into a fluid comprising (i) water and (ii) one of gas, liquid hydrocarbon, and combinations thereof;
wherein the composition comprises a low dosage hydrate inhibitor (LDHI) compound or a salt thereof, the LDHI compound comprising multiple cationic hydrophilic heads comprising a moiety having the chemical formula R 1 R 2 R 3 M + , wherein each of R 1 , R 2 , and R 3 is a C 2 to C 8 hydrocarbon chain independently selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, and combinations thereof, and wherein M is either nitrogen or phosphorous; a lipophilic tail comprising more carbon atoms than each one of R 1 , R 2 , and R 3 ; and a linking group, wherein the LDHI compound comprises two cationic hydrophilic heads for every one lipophilic tail of the compound and wherein the LDHI compound comprises the reaction product of a reaction process that comprises (i) a first reaction between a long-chain primary amine and an epihalohydrin, and (ii) a second reaction between the product of the first reaction with a secondary or tertiary amine.

2. The method of claim 1 , wherein the lipophilic tail is a C 8 to C 18 hydrocarbon chain.

3. The method of claim 1 , wherein each of R 1 , R 2 , and R 3 is C 3 H 7 , and wherein the lipophilic tail is a C 12 to C 16 hydrocarbon chain.

4. A method comprising:
introducing a composition into a fluid comprising (i) water and (ii) one of gas, liquid hydrocarbon, and combinations thereof;
wherein the composition comprises a low dosage hydrate inhibitor (LDHI) compound, the LDHI compound having the structural formula:

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of: hydrogen, a C 1 to C 12 hydrocarbon chain, and combinations thereof;
wherein M is selected from the group consisting of nitrogen and phosphorous;
wherein X is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof;
wherein each of L and L′ independently has the structural formula:

wherein Z of each of L and L′ is independently selected from the group consisting of: hydrogen, R 7 (CO)—, (CH 2 CH 2 O) n , (CH 2 CH(CH 3 )O) n , R 7 SO 2 —, R 7 (SO 2 )O—, R 7 , and combinations thereof; wherein R 7 is a C 1 to C 20 hydrocarbon chain; and further wherein n ranges from 1 to 10;

wherein T is selected from the group consisting of compounds having the following structural formulas:

wherein R is a C 1 to C 20 hydrocarbon chain;
wherein J is selected from the group consisting of hydrogen, a C 1 to C 6 hydrocarbon chain, and combinations thereof;
wherein X″ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof;
wherein M′ is selected from the group consisting of nitrogen and phosphorous; and

wherein Q has the structural formula:

wherein each of L and L′ independently has the structural formula:

wherein Z of each of L and L′ is independently selected from the group consisting of: hydrogen, R 7 (CO)—, (CH 2 CH 2 O) n , (CH 2 CH(CH 3 )O) n , R 7 SO 2 —, R 7 (SO 2 )O—, R 7 , and combination thereof; wherein R 7 is a C 1 to C 20 hydrocarbon chain; and further wherein a ranges from 1 to 10;
wherein M″ is selected from the group consisting of nitrogen and phosphorous;
wherein X′ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof; and
wherein each of R 4 , R 5 , and R 6 is independently selected from the group consisting of: hydrogen, a C 1 to C 12 hydrocarbon chain, and combinations thereof.

5. A method comprising:
introducing a composition into a fluid comprising (i) water and (ii) one of gas, liquid hydrocarbon, and combinations thereof;
wherein the composition comprises a low dosage hydrate inhibitor (LDHI) compound, the LDHI compound having the structural formula:

wherein each of R 1 , R 2 , and R 3 is independently selected from the group consisting of: hydrogen, a C 1 to C 12 hydrocarbon chain, and combinations thereof;
wherein M is selected from the group consisting of nitrogen and phosphorous;
wherein X is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof;
wherein L is a substituted C 1 to C 20 hydrocarbon chain; and
wherein T is selected from the group consisting of compounds having the following structural formulas:

wherein R is an unsubstituted C 8 to C 20 hydrocarbon chain;
wherein J is selected from the group consisting of hydrogen, a C 1 to C 6 hydrocarbon chain, and combinations thereof;
wherein X″ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof;
wherein M′ is selected from the group consisting of nitrogen and phosphorous; and
wherein Q has the structural formula:

wherein L′ is a substituted C 1 to C 20 hydrocarbon chain;
wherein M″ is selected from the group consisting of nitrogen and phosphorous;
wherein X′ is an anion selected from the group consisting of halide, carboxylate, sulfate, organic sulfonate, hydroxide, and combinations thereof; and
wherein each of R 4 , R 5 , and R 6 is independently selected from the group consisting of: hydrogen, a C 1 to C 12 hydrocarbon chain, and combinations thereof.

6. The method of claim 5 , wherein each of L and L′ independently has the structural formula:

wherein Z of each of L and L′ is independently selected from the group consisting of: hydrogen, R 7 (CO)—, (CH 2 CH 2 O) n , (CH 2 CH(CH 3 )O) n , R 7 SO 2 − , R 7 (SO 2 )O—, R 7 , and combinations thereof; wherein R 7 is a C 1 to C 20 hydrocarbon chain, and further wherein n ranges from 1 to 10.

7. The method of claim 6 , wherein L has the same structure as L′.

8. The method of claim 7 , wherein the LDHI compound has the structural formula:

9. The method of claim 8 , wherein each of R 1 , R 2 , and R 3 is a C 2 to C 8 hydrocarbon chain, and further wherein R is an unsubstituted C 8 to C 18 hydrocarbon chain.

10. The method of claim 9 , wherein each of R 1 , R 2 , and R 3 is linear C 3 H 7 , and further wherein

Assignees

• Multi Chem Group Llc

Inventors

• Qu Liangwei
• Sun Yangqiu
• Zhao Funian
• Conkle Curtis
• Acosta Erick J

Classifications

• C09K8/52 Primary

  Compositions for preventing, limiting or eliminating depositions, e.g. for cleaning · CPC title

• C09K8/524 Primary

  organic depositions, e.g. paraffins or asphaltenes · CPC title

• C10L3/107

  Limiting or prohibiting hydrate formation · CPC title

• C09K2208/22

  Hydrates inhibition by using well treatment fluids containing inhibitors of hydrate formers · CPC title