IP Library Granted Patent US 8,858,820
Granted Patent B2
US 8,858,820 · App. 13/646,535 · Granted Oct 14, 2014

Bromofluorocarbon compositions

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Quick Facts
Patent No.
US 8,858,820
App. No.
13/646,535
Granted
Oct 14, 2014
Kind
B2
Abstract

Compositions are described that may be used for applications such as a fire extinguishing composition in fire extinguishing unit, refrigeration, and the like. These compositions include halocarbons and additives that may stabilize the composition in the presence of a metal, water, and/or air. For example, the compositions may include a bromofluorocarbon, such as a bromofluoroalkene, an acid scavenger stabilizer, and an antioxidant stabilizer.

Claims (25)

1. A stabilized composition comprising:

2-bromo-3,3,3-trifluoropropene;

cyclohexene oxide or cyclopentene oxide; and

at least one antioxidant selected from the group consisting of: 2,5-di-tert-butyl-4-methoxyphenol; a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid; and 1,2,5,6-diepoxycyclooctane.

2. The composition of claim 1 consisting essentially of:

2-bromo-3,3,3-trifluoropropene;

cyclohexene oxide; and

2,5-di-tert-butyl-4-methoxyphenol; a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid; or 1,2,5,6-diepoxycyclooctane.

3. The composition of claim 1 , wherein the cyclohexene oxide or cyclopentene oxide has a concentration in the range of about 500 ppm to about 10,000 ppm, based upon the weight of the stabilized composition.

4. The composition of claim 1 , comprising a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid having a concentration in the range of about 200 ppm to about 5000 ppm, based upon the weight of the stabilized composition.

5. The composition of claim 1 , wherein the composition is stored in a container comprising a metal surface, wherein at least a portion of the metal surface is in contact with at least a portion of the composition.

6. The composition of claim 5 , wherein the metal surface comprises at least one of steel and brass.

7. The composition of claim 1 , further comprising N 2 .

8. The composition of claim 7 , wherein the N 2 has a partial pressure of about 20 psig to about 800 psig.

9. A fire extinguishing unit, comprising a container, a valve, a nozzle, and optionally a hose;

wherein said container contains a fire extinguishing composition according to claim 1 :

wherein the composition has a pressure of about 70 psig to about 800 psig.

10. The fire extinguishing system of claim 9 , wherein the container, valve and other wetted parts comprise at least one of steel, stainless steel, carbon steel, aluminum or brass.

11. A method of stabilizing 2-bromo-3,3,3-trifluoropropene comprising adding to the 2-bromo-3,3,3-trifluoropropene an effective amount of:

cyclohexene oxide or cyclopentene oxide; and

at least one antioxidant selected from the group consisting of 2,5-di-tert-butyl-4-methoxyphenol; a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid; and 1,2,5,6-diepoxycyclooctane.

12. The method of claim 11 , comprising adding about 2000 ppm by weight cyclohexane oxide and about 1000 ppm by weight of a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid to the 2-bromo-3,3,3-trifluoropropene.

13. The method of claim 11 , comprising adding about 2000 ppm by weight cyclohexene oxide and about 1000 ppm by weight of 2,5-di-tert-butyl-4-methoxyphenol to the 2-bromo-3,3,3-trifluoropropene.

14. The method of claim 11 , wherein adding cyclohexene oxide or cyclopentene oxide; and 2,5-di-tert-butyl-4-methoxyphenol; a C 7-9 branched alkyl ester of 3,5,-di-tert-butyl-4-hydroxycinnamic acid; or 1,2,5,6-diepoxycyclooctane to the 2-bromo-3,3,3-trifluoropropene provides a composition that is stable in the presence of a metal comprising carbon steel or brass such that substantially no visible change to the metal occurs upon contact between the composition and the metal for about 2 weeks at about 60° C.

15. The method of claim 11 where the purity of the 2-bromo-3,3,3-trifluoropropene is 99.0% or greater.

Assignments (8)
RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY COLLATERAL AT REEL/FRAME NO. 61835/0725 Recorded Jan 17, 2024
From: ARES CAPITAL CORPORATION, AS COLLATERAL AGENT
To: AMERICAN PACIFIC CORPORATION
Reel/Frame 066342/0746 →
PATENT SECURITY AGREEMENT Recorded Nov 1, 2022
From: AMERICAN PACIFIC CORPORATION
To: ARES CAPITAL CORPORATION, AS COLLATERAL AGENT
Reel/Frame 061835/0725 →
TERMINATION AND RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY Recorded Feb 6, 2020
From: KEYBANK NATIONAL ASSOCIATION
To: AMERICAN PACIFIC CORPORATION
Reel/Frame 051841/0110 →
INTELLECTUAL PROPERTY SECURITY AGREEMENT Recorded Dec 16, 2015
From: AMERICAN PACIFIC CORPORATION, A NEVADA CORPORATION
To: KEYBANK NATIONAL ASSOCIATION, AS COLLATERAL AGENT
Reel/Frame 037312/0970 →
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F: 032365/0125 Recorded Dec 15, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: AMERICAN PACIFIC CORPORATION
Reel/Frame 037299/0657 →
RELEASE OF SECURITY INTEREST IN PATENTS RECORDED AT R/F: 032365/0125 Recorded Dec 15, 2015
From: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
To: AMERICAN PACIFIC CORPORATION
Reel/Frame 037292/0957 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 12, 2014
From: GRIFFITH, KRIS N.
To: AMERICAN PACIFIC CORPORATION
Reel/Frame 033093/0191 →
SECURITY AGREEMENT Recorded Feb 27, 2014
From: AMERICAN PACIFIC CORPORATION
To: JEFFERIES FINANCE LLC, AS ADMINISTRATIVE AGENT
Reel/Frame 032365/0125 →