IP Library › Granted Patent US 12,559,659
Granted Patent B2
US 12,559,659 · App. 17/047,860 · Granted Feb 24, 2026

Stabilized fluoroolefin compositions and methods for their production, storage and usage

Inventors: Sheng Peng (Hockessin, DE); Jian Sun-Blanks (Earleville, MD); Barbara Haviland Minor (Elkton, MD); Brian E. Kipp (Avondale, PA); Mary E Koban (Chadds Ford, PA)
Assignee: THE CHEMOURS COMPANY FC, LLC
C09K5/045C10M171/008F25B13/00C09K2205/102C09K2205/122C09K2205/126C09K2205/22C10N2020/101C10N2040/30
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Quick Facts
Patent No.
US 12,559,659
App. No.
17/047,860
Granted
Feb 24, 2026
Kind
B2
Abstract

The present invention relates to compositions comprising at least one fluoroolefin and an effective amount of at least one inhibitor. The stabilized compositions may be useful in cooling apparatus, such as refrigeration, air-conditioning, chillers, and heat pumps, as well as in applications as foam blowing agents, solvents, aerosol propellants, fire extinguishants, and sterilants.

Claims (11)

1 . A method for reducing formation of oligomers, homopolymers and polymers from a fluoroolefin refrigerant composition comprising contacting the fluoroolefin refrigerant composition, which based on the total amount of the composition, contains HFO-1234yf in an amount of ≥99.0 wt. %, HFO-1234ze and HFO-1243zf, with about 50 to 500 ppm of a stabilizer comprising limonene which is liquid at a temperature of between −50° C. and 150° C.,

wherein the composition has been exposed to at least one member selected from the group consisting of air, oxygen, cumene hydroperoxide, fluoroolefin polyperoxides, peroxides, hydroperoxides, persulfates, percarbonates, perborates and hydropersulfates, before said contacting, and

wherein the stabilizer is present in a liquid phase of the fluoroolefin refrigerant composition and at least reduces fluoroolefin derived oligomer, homopolymer and polymer formation from the HFO-1234yf to a level below 0.03 wt. %.

2 . A method for reducing formation of oligomers and homopolymers, the method comprising contacting a composition comprising HFO-1234yf with an amount of at least one inhibitor selected from the group consisting of limonene, α-terpinene, and α-tocopherol,

wherein the amount of the at least one inhibitor is from about 10 ppm to about 2,000 ppm by weight, and

wherein the composition has been exposed to at least one member selected from the group consisting of air, oxygen, cumene hydroperoxide, fluoroolefin polyperoxides, peroxides, hydroperoxides, persulfates, percarbonates, perborates and hydropersulfates, before said contacting.

3 . The method of claim 2 , wherein the HFO-1234yf is present an amount of ≥99.0 wt. % based on a total weight of the composition.

4 . The method of claim 2 , wherein the at least one inhibitor is selected from the group consisting of limonene and α-terpinene.

5 . The method of claim 2 , wherein the at least one inhibitor is limonene.

6 . The method of claim 2 , wherein the at least one inhibitor is d-limonene.

7 . The method of claim 2 , wherein the amount of the at least one inhibitor is from about 10 to about 1,000 ppm by weight.

Assignments (2)
SECURITY INTEREST Recorded Apr 15, 2021
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 055950/0007 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 15, 2020
From: PENG, SHENG; SUN-BLANKS, JIAN; MINOR, BARBARA HAVILAND; KIPP, BRIAN E; KOBAN, MARY E
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 054065/0737 →
Continuity (2)
Provisional Application 62664751 · Apr 30, 2018
Related Publication 20210108119A1 · Apr 15, 2021
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