Amidoamine synthesis, methods to track the reaction process

1. A method of formulating a wellbore fluid, the method comprising:

quantifying the concentration of residual free amine and/or free carboxylic acid in a product mixture prepared from a reaction of a multireactive species and a fatty reactant, wherein the reaction of a multireactive species and a fatty reactant comprises an amide- or imine-forming reaction;

verifying that the concentration for the free amine and/or free acid in the product mixture is within an acceptable threshold; and

combining the product mixture with one or more wellbore fluid components to generate the wellbore fluid;

wherein quantifying the concentration of the residual free amine and/or free carboxylic acid comprises nonaqueous titration.

2. The method of claim 1 , wherein quantifying the concentration of the residual free amine and/or free carboxylic acid comprises:

reacting the product mixture with a silylating agent to convert the residual free amine and/or free carboxylic acid to a respective silylated amine and/or silylated carboxylic acid;

quantifying the concentration of the silylated amine and/or silylated carboxylic acid; and

converting the concentration of the silylated amine and/or silylated carboxylic acid to the concentration of residual free amine and/or free carboxylic acid.

3. The method of claim 2 , wherein quantifying the concentration the silylated amine and/or silylated carboxylic acid comprises measuring the concentration by gas chromatography (GC).

4. The method of claim 2 , wherein quantifying the concentration the silylated amine and/or silylated carboxylic acid comprises measuring the concentration by gas chromatography/mass spectroscopy (GC-MS).

5. The method of claim 2 , wherein the silylating agent is one or more selected from a group consisting of N,O-bis(trimethylsilyl)acetamide (BSA), N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA), N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide (MTBSTFA), and pentafluorophenyldimethylsilyl (flophemesyl), N-Methyl-N-trimethylsilylacetamide (MSA), N,O-bis(trimethylsilyl)carbamate (BSC), N,N-bis(trimethylsilyl)formamide, (BSF), N,N′-bis(trimethylsilyl)urea (BSU), N-Methyl-N-trimethylsilylheptafluorobutyramide (MSHFBA), and hexamethlydisilazane (HMDS).

6. The method of claim 1 , further comprising adjusting the concentration of the free carboxylic acid in the wellbore to a concentration within the range of 0 ppb to 10 ppb (pounds per barrel).

7. The method of claim 1 , wherein the product mixture is further reacted with a second reactant prior to combining the product mixture with one or more wellbore fluid components to generate the wellbore fluid.

8. The method of claim 1 , wherein the nonaqueous titration is performed by mixing a portion of the product mixture with glacial acetic acid and titrating with perchloric acid to determine the concentration of the residual free amine.

9. The method of claim 1 , the product mixture comprises an emulsifier and wherein quantifying the concentration of residual free amine and/or free carboxylic acid comprises:

measuring a first viscosity of a fluid composition containing the emulsifier;

heat aging the fluid; and

measuring a second viscosity of the fluid composition, wherein a difference between the first viscosity and the second viscosity is indicative of the presence of free amines.

10. A method of formulating a wellbore fluid, the method comprising:

quantifying, by nonaqueous titration, the concentration of residual free amine in a product mixture prepared from a reaction of a multireactive species and a fatty reactant, wherein the reaction of a multireactive species and a fatty reactant comprises an amide- or imine-forming reaction;

verifying that the concentration for the residual free amine in the product mixture is within an acceptable threshold; and

combining the product mixture with one or more wellbore fluid components to generate the wellbore fluid;

further comprising determining the concentration of free carboxylic acid in the product mixture, and adjusting the concentration of the free carboxylic acid in the wellbore to a concentration within the range of 0 ppb to 10 ppb.

11. The method of claim 10 , wherein the nonaqueous titration is performed by mixing a portion of the product mixture with glacial acetic acid and titrating with perchloric acid to determine the concentration of the residual free amine.

12. The method of claim 10 , wherein the acceptable threshold of residual free amine is an amine number of 0.

13. The method of claim 10 , wherein the acceptable threshold of residual free amine is an amine number in the range of 0 to 30.

14. The method of claim 10 , further comprising reacting the product mixture with a second reactant prior to combining the product mixture with one or more wellbore fluid components to generate the wellbore fluid.

15. The method of claim 10 , wherein if a product mixture is determined to contain a concentration of residual free amine outside of an acceptable threshold, the method further comprises heating the mixture to further react the product mixture.

16. The method of claim 10 , wherein the wellbore fluid is a water-in-oil emulsion.

17. The method of claim 10 , wherein the nonaqueous titration comprises measuring the product mixture using a pH electrode.

18. The method of claim 10 , wherein the product mixture comprises an amidoamine.

19. A method of monitoring the conversion of a multireactive species, the method comprising:

reacting the multireactive species and a fatty reactant to generate a product mixture, wherein reacting the multireactive species and a fatty reactant comprises an amide- or imine-forming reaction;

quantifying the concentration of residual free amine and/or free carboxylic acid in the product mixture;

verifying that the concentration for the free amine and/or free acid in the product mixture is within an acceptable threshold; and

collecting the product mixture.

20. The method of claim 19 , wherein quantifying the concentration of the residual free amine and/or free carboxylic acid comprises:

reacting the product mixture with a silylating agent to convert the residual free amine and/or free carboxylic acid to a respective silylated amine and/or silylated carboxylic acid;

quantifying the concentration of the silylated amine and/or silylated carboxylic acid; and

converting the concentration of the silylated amine and/or silylated carboxylic acid to the concentration of residual free amine and/or free carboxylic acid.

21. The method of claim 20 , wherein quantifying the concentration the silylated amine and/or silylated carboxylic acid comprises measuring the concentration by gas chromatography (GC).

22. The method of claim 20 , wherein quantifying the concentration the silylated amine and/or silylated carboxylic acid comprises measuring the concentration by gas chromatography/mass spectroscopy (GC-MS).

23. The method of claim 20 , wherein the silylating agent is one or more selected from a group consisting of N,O-bis(trimethylsilyl)acetamide (BSA), N,O-bis(trimethylsilyl)trifluoroacetamide (BSTFA), N-methyl-N-(tert-butyldimethylsilyl)trifluoroacetamide (MTBSTFA), and pentafluorophenyldimethylsilyl (flophemesyl), N-Methyl-N-trimethylsilylacetamide (MSA), N,O-bis(trimethylsilyl)carbamate (BSC), N,N-bis(trimethylsilyl)formamide, (BSF), N,N′-bis(trimethylsilyl)urea (BSU), N-Methyl-N-trimethylsilylheptafluorobutyramide (MSHFBA), and hexamethlydisilazane (HMDS).

24. The method of claim 19 , further comprising adjusting the concentration of the free carboxylic acid in the wellbore to a concentration within the range of 0 ppb to 10 ppb.

25. The method of claim 19 , wherein the product mixture is further reacted with a second reactant prior to combining the product mixture with one or more wellbore fluid components to generate the wellbore fluid.

26. The method of claim 19 , wherein quantifying the concentration of the residual free amine and/or free carboxylic acid comprises nonaqueous titration.

27. The method of claim 26 , wherein the nonaqueous titration is performed by mixing a portion of the product mixture with glacial acetic acid and titrating with perchloric acid to determine the concentration of the residual free amine.

28. The method of claim 19 , the product mixture comprises an emulsifier and wherein quantifying the concentration of residual free amine and/or free carboxylic acid comprises:

measuring a first viscosity of a fluid composition containing the emulsifier;

heat aging the fluid; and

measuring a second viscosity of the fluid composition, wherein a difference between the first viscosity and the second viscosity is indicative of the presence of free amines.