Low ph metal-free preparation of aminated organic acid

Patent metadata

Field	Value
Publication number	US-2016229797-A1
Application number	US-201414779703-A
Country	US
Kind code	A1
Filing date	Oct 17, 2014
Priority date	Oct 17, 2014
Publication date	Aug 11, 2016
Grant date	—

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 )heterocyclo alkylene-, (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 4 )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 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 )heterocyclo alkylene-, (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-.

10 . The process according to claim 9 , 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.

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.

12 . The process according to claim 11 , wherein the compound according to Formula I is:

the compound according to Formula A is

and
the compound according to Formula B is:

13 . The process according to claim 9 , wherein the contacting is performed in an aqueous medium.

14 . The process according to claim 13 , wherein the pH of the aqueous medium is less than about 6.

15 . The process according to claim 14 , wherein the pH of the aqueous medium is less than about 3.

16 . The process according to claim 15 , wherein the pH of the aqueous medium is less than about 2.

17 . The process according to claim 16 , wherein the pH of the aqueous medium is less than about 1.

18 . The process according to claim 13 , wherein the aqueous medium is substantially free of inorganic bases.

19 . The process according to claim 9 , wherein the contacting occurs at a temperature between about 50° C. and about 100° C.

20 . The process according to claim 19 , wherein the temperature is between about 60° C. and about 80° C.

21 . The process according to claim 20 , wherein the temperature is about 70° C.

22 . 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.

Assignees

• Halliburton Energy Services Inc

Inventors

• Recio Iii Antonio
• Reyes Enrique Antonio

Classifications

• C09K8/86 Primary

  containing organic compounds · CPC title

• E21B43/16

  Enhanced recovery methods for obtaining hydrocarbons · CPC title

• E21B43/26

  by forming crevices or fractures · CPC title

• C09K8/52

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

• C07C303/04 Primary

  by substitution of hydrogen atoms by sulfo or halosulfonyl groups · CPC title