Phosphono paraffins

Patent metadata

Field	Value
Publication number	US-10557101-B2
Application number	US-201816171165-A
Country	US
Kind code	B2
Filing date	Oct 25, 2018
Priority date	Jan 11, 2017
Publication date	Feb 11, 2020
Grant date	Feb 11, 2020

Abstract

Aspects described herein generally relate to methods of making a phosphono paraffin comprising forming a reaction mixture by mixing a haloparaffin, a phosphite, and sodium iodide. Methods comprise heating the reaction mixture to form the phosphono paraffin. Aspects described herein further relate to a phosphono paraffin represented by formula (I):

wherein each instance of R 1 is independently —H or

wherein each instance of R 2 and R 3 is independently linear or branched C 1-20 alkyl, C 1-20 cycloalkyl, or aryl; the number of instances where R 1 is

of formula (I) is between about 2 and about 8; and n is an integer between 4 and 22.

First claim

What is claimed is:

1. A method of making a secondary phosphono paraffin, comprising:
mixing
(i) a secondary haloparaffin,
(ii) a phosphite, wherein a molar ratio of phosphite to secondary haloparaffin is from about 1:1 to about 10:1, and
(iii) one or more of sodium iodide, potassium iodide, or potassium bromide to form a reaction mixture, wherein a molar ratio of the sodium iodide, potassium iodide, or potassium bromide to secondary haloparaffin is from 1:1 to about 10:1; and

heating the reaction mixture to form a secondary phosphono paraffin at an overall yield of from about 20% to about 80%.

2. The method of claim 1 , wherein the secondary haloparaffin is a chloroparaffin.

3. The method of claim 1 , wherein the secondary haloparaffin has one or more secondary halogen moieties.

4. The method of claim 1 , further comprising isolating the secondary phosphono paraffin at an overall yield of from about 40% to about 60%.

5. The method of claim 1 , wherein the phosphite is represented by the formula

wherein each of R 1 , R 2 , and R 3 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl.

6. The method of claim 5 , wherein each of R 1 , R 2 , and R 3 is independently C 1-5 alkyl or cycloalkyl of C 6 or less.

7. The method of claim 5 , wherein the phosphite comprises triethyl phosphite, tributyl phosphite, tripentyl phosphite, trihexyl phosphite, triheptyl phosphite, trioctyl phosphite, trinonyl phosphite, tridecyl phosphite, or mixtures thereof.

8. The method of claim 1 , wherein heating is performed at a temperature from about 120° C. to about 200° C.

9. The method of claim 1 , further comprising mixing a solvent with the secondary haloparaffin, the phosphite, and sodium iodide, wherein the solvent comprises dimethylsulfoxide, dimethylformamide, chlorobenzene, N-methyl-2-pyrrolidinone, xylenes, or mixtures thereof.

10. The method of claim 1 , wherein a molar ratio of phosphite:secondary haloparaffin is from about 2:1 to about 6:1.

11. The method of claim 1 , wherein mixing comprises mixing the secondary haloparaffin and the phosphite with sodium iodide.

12. The method of claim 11 , wherein a molar ratio of sodium iodide:secondary haloparaffin is from about 2:1 to about 6:1.

13. The method of claim 1 , further comprising cooling the reaction product and isolating the secondary phosphono paraffin from a sodium halide byproduct.

14. The method of claim 1 , wherein the phosphono paraffin is represented by formula (I):

wherein:
each instance of R 1 is independently —H or

each instance of R 2 and R 3 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl;
n is an integer from 4 to 22;
and the number of instances where R 1 is

of formula (I) is from about 2 to about 8.

15. The method of claim 14 , wherein each of R 2 and R 3 is independently C 1-5 alkyl or cycloalkyl of C 6 or less.

16. The method of claim 14 , wherein the number of instances where R 1 is

of formula (I) is from about 3 to about 6.

17. The method of claim 14 , wherein n is an integer from about 10 to about 16.

18. The method of claim 14 , wherein each of R 2 and R 3 is independently linear C 1-20 alkyl.

19. The method of claim 18 , wherein each of R 2 and R 3 is independently C 1-5 alkyl or cycloalkyl of C 6 or less.

20. The method of claim 14 , wherein each of R 2 and R 3 are the same.

21. The method of claim 14 , wherein the secondary phosphono paraffin comprises:

wherein each of R 1 and R 2 is independently C 1-20 alkyl, cycloalkyl of C 20 or less, or aryl.

22. The method of claim 21 , wherein each of R 1 and R 2 are independently linear C 1-20 alkyl.

23. The method of claim 21 , wherein each of R 1 and R 2 is independently C 1-5 alkyl or cycloalkyl of C 6 or less.

24. The method of claim 22 , wherein each of R 1 and R 2 are the same.

25. The method of claim 22 , wherein each of R 1 and R 2 are independently isopropyl, butyl, or phenyl.

26. The method of claim 14 , wherein the secondary phosphono paraffin comprises:

27. The method of claim 14 , wherein the secondary phosphono paraffin comprises:

and mixtures thereof.

28. The method of claim 14 , wherein the secondary phosphono paraffin comprises:

and mixtures thereof.

29. The method of claim 14 , wherein the secondary phosphono paraffin comprises:

and mixtures thereof.

Assignees

• Boeing Co

Inventors

• Ballard Mathew John
• Casey Philip Stephen
• Holmes Susan Wan-Yi
• Way Cameron David

Classifications

• C10N2040/08

  Hydraulic fluids, e.g. brake-fluids · CPC title

• C10N2030/12

  Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives · CPC title

• C10N2030/10

  Inhibition of oxidation, e.g. anti-oxidants · CPC title

• C10M2207/042

  Epoxides · CPC title

• C10M2223/0603

  used as base material · CPC title