Low pH metal-free preparation of aminated organic acid

Patent metadata

Field	Value
Publication number	US-9676706-B2
Application number	US-201414779703-A
Country	US
Kind code	B2
Filing date	Oct 17, 2014
Priority date	Oct 17, 2014
Publication date	Jun 13, 2017
Grant date	Jun 13, 2017

Abstract

The invention provides a process for making compounds according to Formula I:

where R 1 , R 1a , R 2 , R 2a , R 3 and R 3a are defined as set forth in the specification. Formula I compounds are useful as chelants and stabilizers of cations in aqueous media and the invention therefore provides a method for using the compounds in the treatment of subterranean formations, such as in acidizing operations.

First claim

We claim:

1. A method of treating a subterranean formation, the method comprising placing into the subterranean formation a composition comprising a compound according to Formula I:

that is prepared by a process comprising contacting a compound of Formula A:

with a compound of Formula B:

wherein
R 1 , R 1a , R 2 , R 2a , R 3 and R 3a are independently selected from the group consisting of H, —OH, halo, straight or branched (C 1 -C 6 )alkyl, straight or branched (C 2 -C 6 )alkenyl, straight or branched (C 2 -C 6 )alkynyl, (C 3 -C 14 )aryl, (C 3 -C 14 )-cycloalkyl, (C 3 -C 14 )aryl(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl-(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl, (C 3 -C 14 )heterocycloalkyl, (C 3 -C 14 )heterocycloalkyl-(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl-(C 3 -C 6 )heterocycloalkylene-, (C 3 -C 14 )aryl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )-aryl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )heteroaryl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )heterocycloalkyl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-.

2. The method according to claim 1 , wherein the placing comprises placing the composition in at least one of a fracture and flow path in the subterranean formation.

3. The method according to claim 2 , wherein the fracture is present in the subterranean formation at the time when the composition is placed into the subterranean formation.

4. The method according to claim 2 , wherein the method further comprises forming the fracture or flow path.

5. The method according to claim 1 , wherein the placing comprises gravel packing.

6. The method according to claim 1 , further comprising fracturing the subterranean formation to form at least one fracture in the subterranean formation.

7. The method according to claim 1 , wherein the composition further comprises a carrier fluid.

8. The method according to claim 1 , further comprising combining the composition with an aqueous or oil-based fluid comprising a fracturing fluid, spotting fluid, clean-up fluid, completion fluid, remedial treatment fluid, abandonment fluid, pill, packer fluid, or a combination thereof.

9. A system for performing the method of claim 1 , the system comprising:
a tubular disposed in the subterranean formation; and
a pump configured to pump the composition in the subterranean formation through the tubular.

10. A process for synthesizing a compound according to Formula I:

comprising contacting a compound of Formula A:

with a compound of Formula B:

wherein
R 1 , R 1a , R 2 , R 2a , R 3 and R 3a are independently selected from the group consisting of H, —OH, halo, straight or branched (C 1 -C 6 )alkyl, straight or branched (C 2 -C 6 )alkenyl, straight or branched (C 2 -C 6 )alkynyl, (C 3 -C 14 )aryl, (C 3 -C 14 )-cycloalkyl, (C 3 -C 14 )aryl(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl-(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl, (C 3 -C 14 )heterocycloalkyl, (C 3 -C 14 )heterocycloalkyl-(C 1 -C 6 )alkylene-, (C 3 -C 14 )heteroaryl-(C 3 -C 6 )heterocycloalkylene-, (C 3 -C 14 )aryl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )-aryl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )heteroaryl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-, (C 3 -C 14 )heterocycloalkyl-(C 1 -C 6 )alkyl-(C 3 -C 14 )heterocycloalkylene-.

11. The process according to claim 10 , wherein R 1 , R 1a , R 2 , R 2a , R 3 and R 3a are independently selected from the group consisting of H and straight or branched (C 1 -C 6 )alkyl, straight or branched (C 2 -C 6 )alkenyl, straight or branched (C 2 -C 6 )alkynyl, (C 3 -C 14 )aryl, and (C 3 -C 14 )-cycloalkyl.

12. The process according to claim 11 , wherein R 1 , R 1a , R 2 , R 2a , R 3 and R 3a are independently selected from the group consisting of H and straight or branched (C 1 -C 6 )alkyl.

13. The process according to claim 12 , wherein the compound according to Formula I is:

the compound according to Formula A is

and
the compound according to Formula B is:

14. The process according to claim 10 , wherein the contacting is performed in an aqueous medium.

15. The process according to claim 14 , wherein the pH of the aqueous medium is less than about 6.

16. The process according to claim 15 , wherein the pH of the aqueous medium is less than about 3.

17. The process according to claim 16 , wherein the pH of the aqueous medium is less than about 2.

18. The process according to claim 17 , wherein the pH of the aqueous medium is less than about 1.

19. The process according to claim 14 , wherein the aqueous medium is substantially free of inorganic bases.

20. The process according to claim 10 , wherein the contacting occurs at a temperature between about 50° C. and about 100° C.

21. The process according to claim 20 , wherein the temperature is between about 60° C. and about 80° C.

22. The process according to claim 21 , wherein the temperature is about 70° C.

Assignees

• Halliburton Energy Services Inc

Inventors

• Recio Iii Antonio
• Reyes Enrique Antonio

Classifications

• C09K8/86 Primary

  containing organic compounds · CPC title

• C09K8/50

  Compositions for plastering borehole walls, i.e. compositions for temporary consolidation of borehole walls (compositions for consolidating loose sand or the like around wells C09K8/56) · CPC title

• C09K8/035

  Organic additives · CPC title

• E21B43/26

  by forming crevices or fractures · CPC title

• C09K8/84

  Compositions based on water or polar solvents (C09K8/66, C09K8/82 take precedence) · CPC title