Stabilized trifluoroiodomethane compositions

• US 20060033072A1
• Filed: 04/18/2005
• Published: 02/16/2006
• Est. Priority Date: 04/16/2004
• Status: Abandoned Application

• Current Assignee: Honeywell International Inc.
• Original Assignee: Honeywell International Inc.
• Inventors: Singh, Rajiv R., Thomas, Raymond H., Wilson, David P.
• Application Number:
  US11/109,575
• Publication Number:
  US 20060033072A1
• Time in Patent Office: Days
• US Class Current: 252/67
• CPC Class Codes: C09K 2205/122 Halogenated hydrocarbons
• CPC Class Codes: C09K 2205/126 Unsaturated fluorinated hydrocarbons
• CPC Class Codes: C09K 3/30 for aerosols aerosol containers B65D83/14
• CPC Class Codes: C09K 5/045 containing only fluorine as halogen
• CPC Class Codes: C10M 171/008 Lubricant compositions compatible with refrigerants
• CPC Class Codes: C10M 2207/042 Epoxides
• CPC Class Codes: C10N 2020/101 Containing Hydrofluorocarbons

Abstract

Provided are novel compositions comprising trifluoroiodomethane and an effective amount of a stabilizer preferably comprising at least one phenol compound and optionally at least one epoxide selected from the group consisting of aromatic epoxides, alkyl epoxides, alkenyl epoxides, multisubstituted epoxides, and combinations of two or more thereof. Also provided are methods of stabilizing a composition comprising trifluoroiodomethane by providing a composition comprising trifluoroiodomethane and introducing to the provided composition an effective amount of a stabilizer comprising at least one phenol compound and optionally at least one epoxide selected from the group consisting of aromatic epoxides, alkyl epoxides, alkenyl epoxides, and combinations of two or more thereof.

Claims

1. A composition comprising trifluoroiodomethane and an effective amount of a stabilizer comprising at least one phenol compound.

2. The composition of claim 1 wherein said stabilizer further comprises at least one epoxide selected from the group consisting of aromatic epoxides, alkyl epoxides, alkenyl epoxides, multisubstituted epoxides, and combinations of two or more thereof.

3. The composition of claim 1 wherein said at least one phenol compound is selected from the group consisting of 4,4′

-methylenebis(2,6-di-tert-butylphenol);

4,4′

-bis(2,6-di-tert-butylphenol);

2,2-biphenyldiols, 4,4-biphenyldiols;

derivatives of 2,2- and 4,4-biphenyldiols;

2,2′

-methylenebis(4-ethyl-6-tertbutylpheol);

2,2′

-methylenebis(4-methyl-6-tert-butylphenol);

4,4,-butylidenebis(3-methyl-6-tert-butylphenol);

4,4,-isopropylidenebis(2,6-di-tert-butylphenol);

2,2′

-methylenebis(4-methyl-6-nonylphenol);

2,2′

-isobutylidenebis(4,6-dimethylphenol);

2,2′

-methylenebis(4-methyl-6-cyclohexylphenol);

2,6-di-tert-butyl-4-methylphenol;

BHT;

2,6-di-tert-butyl-4-ethylphenol;

2,4-dimethyl-6-tert-butylphenol;

2,6-di-tert-.alpha.-dimethylamino-p-cresol;

2,6-di-tert-butyl-4(N,N′

-dimethylaminomethylphenol);

4,4′

-thiobis (2-methyl-6-tert-butylphenol);

4,4′

-thiobis (3-methyl-6-tert-butylphenol);

2,2′

-thiobis (4-methyl-6-tert-butylphenol);

bis(3-methyl-4-hydroxy-5-tert-butylbenzyl) sulfide;

bis(3,5-di-tert-butyl-4-hydroxybenzyl)sulfide;

tocopherol;

hydroquinone;

t-butyl hydroquinone;

derivatives of hydroquinone; and

combinations of two or more thereof.

4. The composition of claim 3 wherein said at least one phenol comprises tocopherol.

5. The composition of claim 2 wherein said at least one epoxide comprises an aromatic epoxide defined by the formula I:

wherein;

R is hydrogen, alkyl, fluoroalkyl, aryl, fluoroaryl, or

Ar is a substituted or unsubstituted phenylene or napthylene moiety.

6. The composition of claim 5 wherein said aromatic epoxide of Formula I is selected from the group consisting of butylphenylglycidyl ether;

pentylphenylglycidyl ether;

hexylphenylglycidyl ether;

heptylphenylglycidyl ether;

octylphenylglycidyl ether;

nonylphenylglycidyl ether;

decylphenylglycidyl ether;

glycidyl methyl phenyl ether;

1,4-diglycidyl phenyl diether and derivatives thereof;

1,4-diglycidyl naphthyl diether and derivatives thereof;

2,2′

[[[5-heptadecafluorooctyl]1,3phenylene]bis[[2,2,2trifluoromethyl]ethylidene]oxymethylene]bisoxirane;

naphthyl glycidyl ether;

4-methoxyphenyl glycidyl ether;

derivatives of naphthyl glycidyl ether; and

combinations of two or more thereof.

7. The composition of claim 1 wherein said at least one epoxide comprises an alkyl or alkenyl epoxide defined by the formula II:

wherein Ralk is a substituted or unsubstituted alkyl or alkenyl group.

8. The composition of claim 7 wherein Ralk is a substituted alkyl, unsubstituted alkyl, substituted alkenyl, or unsubstituted alkenyl group having from about 1 to about 10 carbon atoms.

9. The composition of claim 7 wherein said epoxide of Formula II is selected from the group consisting of n-butyl glycidyl ether, isobutyl glycidyl ether, hexanediol diglycidyl ether, allyl glycidyl ether, polypropylene glycol diglycidyl ether, and combinations of two or more thereof.

10. The composition of claim 9 wherein said at least one epoxide comprises allyl glycidyl ether.

11. The composition of claim 4 wherein said at least one epoxide comprises allyl glycidyl ether.

12. The composition of claim 1 further comprising a fluid selected from the group consisting of HFCs, and combinations of two or more thereof.

13. The composition of claim 12 wherein said fluid comprises HFO-1234ze.

14. The composition of claim 12 wherein said fluid comprises HFO-1234yf.

15. The composition of claim 12 wherein said fluid comprises HFC-32.

16. The composition of claim 12 wherein said fluid comprises HFC-152a.

17. The composition of claim 12 wherein said fluid comprises at least one isomer of HFO-1225.

18. The composition of claim 1 further comprising a hydrocarbon selected from the group consisting of propane, isomers of butane, isomers of pentane, and combinations thereof.

19. The composition of claim 1 further comprising a lubricant.

20. The composition of claim 19 wherein said lubricant is selected from the group consisting of mineral oil, silicone oil, polyalkyl benzenes (PABs), polyol esters (POEs), polyalkylene glycols (PAGs), polyalkylene glycol esters (PAG esters), polyvinyl ethers (PVEs), poly(alpha-olefins) (PAOs) and combinations of two or more thereof.

21. The composition of claim 20 wherein said lubricant comprises mineral oil.

22. The composition of claim 1 further comprising an additive selected from the group consisting of metal passivators, extreme pressure additives, corrosion inhibitors, and combinations of two or more thereof.

23. A method of stabilizing a composition comprising trifluoroiodomethane comprising providing a composition comprising trifluoroiodomethane and introducing to the provided composition an effective amount of a stabilizer comprising at least one phenol compound and optionally at least one epoxide selected from the group consisting of aromatic epoxides, alkyl epoxides, alkenyl epoxides, and combinations of two or more thereof.

24. The method of claim 23 wherein said provided composition further comprises a fluid selected from the group consisting of HFCs, and combinations of two or more thereof.

25. The method of claim 24 wherein said fluid comprises HFO-1234ze.

26. The method of claim 24 wherein said fluid comprises HFO-1234yf.

27. The method of claim 24 wherein said fluid comprises HFC-32.

28. The method of claim 24 wherein said fluid comprises HFC-152a.

29. The method of claim 23 wherein said introducing step comprises introducing a lubricant comprising said effective amount of said stabilizer to said composition comprising trifluoroiodomethane.

30. The method of claim 29 wherein said lubricant is selected from the group consisting of mineral oils, silicone oil, polyalkyl benzenes (PABs), polyol esters (POEs), polyalkylene glycols (PAGs), polyalkylene glycol esters (PAG esters), polyvinyl ethers (PVEs), poly(alpha-olefins) (PAOs), and combinations of two or more of these.

31. A composition comprising trifluoroiodomethane and an effective amount of at least one stabilizer.