IP Library › Granted Patent US 12,416,431
Granted Patent B2
US 12,416,431 · App. 19/063,551 · Granted Sep 16, 2025

HFO-1234ZE, HFO-1225ZC and HFO-1234YF compositions and processes for producing and using the compositions

Inventors: Sheng Peng (Hockessin, DE); Mario Joseph Nappa (Leesburg, FL)
Assignee: THE CHEMOURS COMPANY FC, LLC
F25B13/00C07C17/357C07C19/08C07C21/18
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 12,416,431
App. No.
19/063,551
Granted
Sep 16, 2025
Kind
B2
Abstract

A fluoropropene composition comprising Z-1,3,3,3-tetrafluoropropene, E-1,3,3,3-tetrafluoropropene, 1,1,3,3,3-pentafluoropropene, 2,3,3,3-tetrafluoropropene, and optionally 1,1,1,3,3-pentafluoropropane wherein the 2,3,3,3-tetrafluoropropene being present in an amount of 0.00001 to 1.0%. A method of producing the fluoropropene, methods for using the fluoropropene and the composition formed are also disclosed.

Claims (19)

1. A tetrafluoropropene composition comprising:

(i) E-1,3,3,3-tetrafluoropropene (HFO-1234ze(E));

(ii) Z-1,3,3,3-tetrafluoropropene (HFO-1234ze(Z)),

(iii) one or more additional compounds selected from the group consisting of HFO-1225zc, HCFO-1233xf, HFC-236fa, HFC-245fa, HFO-1234yf and HCFO-1233zd, and

(iv) optionally one or more additional compounds selected from the group consisting of HFO-1234ye, HFC-1243zf, HFC-32, HFC-125, HFC-134, HFC-134a, HFC-143a, HFC-152a, HFC-161, HFC-227ea, HFC-236ea, and HFO-1336mzz(E), and TFP,

wherein based on the total amount of the composition, ≥99% by weight HFO-1234ze(E)) is present, and the total amount of HFO-1234ze(Z), (iii) and (iv), if present, is between >0 and ≤1% by weight, such that the total amount of the composition is 100%.

2. The composition of claim 1 , wherein HFC-1225zc is present in an amount of between >0 and <about 170 ppm.

3. The composition of claim 1 , wherein the amount of HFO-1234ze(E) is ≥99.8% by weight and the total amount of (ii)-(iv) comprises the difference between ≥99.8% by weight HFO-1234ze(E)) and 100%.

4. The composition of claim 3 , wherein the one or more additional compounds (iii) comprise HFC-236fa.

5. The composition of claim 3 , wherein the one or more additional compounds (iii) are selected from the group consisting of HCFO-1233xf and HCFO-1233zd.

6. The composition of claim 1 , wherein the amount of HFO-1234ze(E) is ≥99.9% by weight and the total amount of (ii)-(iv) comprises the difference between ≥99.9% by weight HFO-1234ze(E)) and 100%.

7. The composition of claim 1 , wherein the amount of HFO-1234ze(E) is ≥99.98% by weight and the total amount of (ii)-(iv) comprises the difference between ≥99.98% by weight HFO-1234ze(E)) and 100%.

8. The composition of claim 1 , wherein the one or more additional compounds (iii) are selected from the group consisting of HCFO-1233xf, HFC-236fa, HFC-245fa and HCFO-1233zd.

9. The composition of claim 8 , wherein the one or more additional compounds (iii) are selected from the group consisting of HCFO-1233xf, HFC-236fa, and HCFO-1233zd.

10. The composition of claim 9 , wherein the one or more additional compounds (iii) comprise HFC-236fa.

11. The composition of claim 9 , wherein the one or more additional compounds (iii) are selected from the group consisting of HCFO-1233xf and HCFO-1233zd.

12. The composition of claim 1 , further comprising HCFC-124.

13. A process for transferring heat, the process comprising providing the composition of claim 1 , and circulating and contacting an article with the composition of claim 1 .

14. A method of producing cooling, the method comprising: providing the composition of claim 1 in the vicinity of a body to be cooled and thereafter condensing the composition.

Assignments (1)
SECURITY INTEREST Recorded Apr 10, 2025
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 070812/0603 →
Continuity (12)
Continuation 18886068 · Sep 16, 2024
Continuation 18414971 · Jan 17, 2024
Continuation 18220777 · Jul 11, 2023
Continuation 18102007 · Jan 26, 2023
Continuation 17733563 · Apr 29, 2022
Continuation 17536970 · Nov 29, 2021
Continuation 17193021 · Mar 5, 2021
Continuation PCTUS2020029690 · Apr 24, 2020
Continuation 17270654
Continuation In Part PCTUS2019057999 · Oct 25, 2019
Provisional Application 62750991 · Oct 26, 2018
Related Publication 20250198665A1 · Jun 19, 2025
References Cited (151)
US 3398204A · Gallant · 1968 [cited by applicant]
US 3413363A · Pindzola · 1968 [cited by applicant]
US 5986151A · Van Der Puy · 1999 [cited by applicant]
US 6034289A · Christoph et al. · 2000 [cited by applicant]
US 6124510A · Elsheikh et al. · 2000 [cited by applicant]
US 6239325B1 · Kishimoto et al. · 2001 [cited by applicant]
US 7026520B1 · Mukhopadhyay et al. · 2006 [cited by applicant]
US 7423188B2 · Miller et al. · 2008 [cited by applicant]
US 7534366B2 · Singh et al. · 2009 [cited by applicant]
US 7663007B2 · Rao et al. · 2010 [cited by applicant]
US 7862742B2 · Minor et al. · 2011 [cited by applicant]
US 7981312B2 · Nappa et al. · 2011 [cited by applicant]
US 8067650B2 · Wang et al. · 2011 [cited by applicant]
US 8071826B2 · Van Der Puy · 2011 [cited by examiner]
US 8148317B2 · Singh et al. · 2012 [cited by applicant]
US 8232435B2 · Sievert et al. · 2012 [cited by applicant]
US 8398882B2 · Rao et al. · 2013 [cited by applicant]
US 8420754B2 · Cann et al. · 2013 [cited by applicant]
US 8436217B2 · Wang et al. · 2013 [cited by applicant]
US 8444874B2 · Singh et al. · 2013 [cited by applicant]
US 8822739B2 · Nappa · 2014 [cited by applicant]
US 8889031B2 · Sawada et al. · 2014 [cited by applicant]
US 8926856B2 · Low · 2015 [cited by applicant]
US 9175202B2 · Low · 2015 [cited by applicant]
US 9175203B2 · Rached · 2015 [cited by applicant]
US 9187683B2 · Low · 2015 [cited by applicant]
US 9199225B2 · Hutama et al. · 2015 [cited by applicant]
US 9272968B2 · Kopkalli et al. · 2016 [cited by applicant]
US 9302962B2 · Peng et al. · 2016 [cited by applicant]
US 9410105B2 · Desantis et al. · 2016 [cited by applicant]
US 9512343B2 · Rached et al. · 2016 [cited by applicant]
US 9556372B2 · Kujak · 2017 [cited by examiner]
US 9598621B2 · Minor · 2017 [cited by examiner]
US 9624413B2 · Fukushima · 2017 [cited by applicant]
US 9683156B2 · Rached · 2017 [cited by examiner]
US 9752069B2 · Boussand · 2017 [cited by applicant]
US 9783720B2 · Kontomaris · 2017 [cited by applicant]
US 9809515B2 · Elsheikh et al. · 2017 [cited by applicant]
US 9957429B2 · Fukushima et al. · 2018 [cited by applicant]
US 9994750B2 · Singh et al. · 2018 [cited by applicant]
US 10023780B2 · Guerin et al. · 2018 [cited by applicant]
US 10029961B2 · Deur-Bert et al. · 2018 [cited by applicant]
US 10029964B2 · Kopkalli et al. · 2018 [cited by applicant]
US 10035937B2 · Yana Motta · 2018 [cited by examiner]
US 10035938B2 · Rached · 2018 [cited by applicant]
US 10047326B2 · Tani et al. · 2018 [cited by applicant]
US 10081749B2 · Taniguchi · 2018 [cited by examiner]
US 10113093B2 · Rached · 2018 [cited by applicant]
US 10119056B2 · Rached et al. · 2018 [cited by applicant]
US 10125296B2 · Rached · 2018 [cited by applicant]
US 10308853B2 · Andre et al. · 2019 [cited by applicant]
US 10316231B2 · Rached · 2019 [cited by applicant]
US 10343963B2 · Bonnet et al. · 2019 [cited by applicant]
US 10450488B2 · Boussand · 2019 [cited by applicant]
US 10519083B2 · Okamoto et al. · 2019 [cited by applicant]
US 10532965B2 · Pigamo et al. · 2020 [cited by applicant]
US 10688329B2 · Nappa · 2020 [cited by applicant]
US 10858561B2 · Abbas et al. · 2020 [cited by applicant]
US 10858564B2 · Rached · 2020 [cited by applicant]
US 10899686B2 · Johnson et al. · 2021 [cited by applicant]
US 11001546B2 · Deur-Bert et al. · 2021 [cited by applicant]
US 11046877B1 · Nappa et al. · 2021 [cited by applicant]
US 11130893B2 · Rached · 2021 [cited by applicant]
US 11359122B2 · Rached · 2022 [cited by applicant]
US 11370948B2 · Rached · 2022 [cited by applicant]
US 20040167366A1 · Rao et al. · 2004 [cited by applicant]
US 20040256594A1 · Singh et al. · 2004 [cited by applicant]
US 20050013764A1 · Merkel et al. · 2005 [cited by applicant]
US 20050124840A1 · Chen et al. · 2005 [cited by applicant]
US 20060043330A1 · Wilson et al. · 2006 [cited by applicant]
US 20090099395A1 · Sakyu et al. · 2009 [cited by applicant]
US 20090099396A1 · Mukhopadhyay et al. · 2009 [cited by applicant]
US 20090118555A1 · Wang et al. · 2009 [cited by applicant]
US 20090158771A1 · Low et al. · 2009 [cited by applicant]
US 20090305876A1 · Singh et al. · 2009 [cited by applicant]
US 20100044619A1 · Hulse et al. · 2010 [cited by applicant]
US 20100163781A1 · Sharratt et al. · 2010 [cited by applicant]
US 20110023507A1 · Yana Motta et al. · 2011 [cited by applicant]
US 20120059200A1 · Pokrovski et al. · 2012 [cited by applicant]
US 20120128964A1 · Hulse et al. · 2012 [cited by applicant]
US 20120172636A1 · Pokrovski et al. · 2012 [cited by applicant]
US 20120172639A1 · Nappa et al. · 2012 [cited by applicant]
US 20120256120A1 · Bouvier et al. · 2012 [cited by applicant]
US 20130099154A1 · Boussand et al. · 2013 [cited by applicant]
US 20140047860A1 · Spatz et al. · 2014 [cited by applicant]
US 20140051896A1 · Imura et al. · 2014 [cited by applicant]
US 20140191154A1 · Minor et al. · 2014 [cited by applicant]
US 20140223927A1 · Pottker · 2014 [cited by examiner]
US 20140264147A1 · Yana Motta et al. · 2014 [cited by applicant]
US 20140331697A1 · Minor · 2014 [cited by examiner]
US 20140336424A1 · Okamoto et al. · 2014 [cited by applicant]
US 20150252281A1 · Saito et al. · 2015 [cited by applicant]
US 20150299547A1 · Seeton et al. · 2015 [cited by applicant]
US 20150377389A1 · Blondel et al. · 2015 [cited by applicant]
US 20160009555A1 · Bonnet et al. · 2016 [cited by applicant]
US 20160031773A1 · Bonnet et al. · 2016 [cited by applicant]
US 20160215133A1 · Bonnet · 2016 [cited by applicant]
US 20160272561A1 · Rached et al. · 2016 [cited by applicant]
US 20170137682A1 · Hulse et al. · 2017 [cited by applicant]
US 20170198184A9 · Yana Motta et al. · 2017 [cited by applicant]
US 20170210686A1 · Pigamo · 2017 [cited by applicant]
US 20180355269A1 · Low et al. · 2018 [cited by applicant]
US 20190047925A1 · Hong et al. · 2019 [cited by applicant]
US 20210198547A1 · Ohkubo et al. · 2021 [cited by applicant]
CN 104710274A · 2015 [cited by applicant]
CN 104069878B · 2016 [cited by applicant]
CN 104531079B · 2018 [cited by applicant]
EP 0486333B1 · 1994 [cited by applicant]
EP 3109302B1 · 2020 [cited by applicant]
EP 3130649B1 · 2024 [cited by applicant]
WO 2002077117A2 · 2002 [cited by applicant]
WO 2006094303A2 · 2006 [cited by applicant]
WO 2008002500A1 · 2008 [cited by applicant]
WO 2008009923A2 · 2008 [cited by applicant]
WO 2008030443A1 · 2008 [cited by applicant]
WO 2010119265A1 · 2010 [cited by applicant]
WO 2011130237A1 · 2011 [cited by applicant]
WO 2013011291A1 · 2013 [cited by applicant]
WO 2013119919A1 · 2013 [cited by applicant]
WO 2013148300A1 · 2013 [cited by applicant]
WO 2014117014A2 · 2014 [cited by applicant]
WO 2016132111A1 · 2016 [cited by applicant]
WO 2017029499A1 · 2017 [cited by applicant]
WO 2017044719A1 · 2017 [cited by applicant]
WO 2020086928A1 · 2020 [cited by applicant]
AHRI “2017 Standard for Specification for Refrigerants”, Sep. 2017, pp. 1-31 (Year: 2017). [cited by applicant]
Araner “Advanced refrigerants R1233zd as substitute of R123”, published Jun. 14, 2018, pp. 1-9 (Year: 2018). [cited by applicant]
Ashrae “Ashrae Refrigerant Designations”, Published Oct. 18, 2018, pp. 1-5 (Year: 2018). [cited by applicant]
Bitzer “Refrigerant Report 20”, Oct. 17, 2018, pp. 1-49 (Year: 2018). [cited by applicant]
Che et al., Experimental Study on Hydrate Cool Storage Medium of HFO-1234yf and HFO-1234ze Refrigerant Mixture, 2017, College of Energy and Power Engineering, University of Shanghai for Science and Technology, Shanghai,… [cited by applicant]
Designated and Safety Classification of Refrigerants, ASHRAE Standard, ANSI/ASHRAE Standard 34, 2016. [cited by applicant]
Designation and Safety Classification of Refrigerants, Addenda 2015 Supplement, ANSI/ASHRAE Addenda a, b, c, d, e, f, g, h, i, j, k, l, m, n to ANSI/ASHRAE Standard 34-2013, 2015, Atlanta, Georgia. [cited by applicant]
Designation and Safety Classification of Refrigerants, Addenda, ANSI/ASHRAE Addenda ac, ad, ae and af to ANSI/ASHRAE Standard 34-2010, Atlanta, Georgia. [cited by applicant]
Designation and Safety Classification of Refrigerants, Addenda, ANSI/ASHRAE Addendum ag to ANSI/ASHRAE Standard 34-2013, Atlanta, Georgia. [cited by applicant]
Designation and Safety Classification of Refrigerants, ANSI/ASHRAE Standard 34-2010 (Supersedes ANSI/ASHRAE Standard 34-2007), Includes ANSI/ASHRAE addenda listed in Appendix H, Atlanta, Georgia. [cited by applicant]
Designation and Safety Classification of Refrigerants, ANSI/ASHRAE Standard 34-2013 (Supersedes ANSI/ASHRAE Standard 34-2010), Includes ANSI/ASHRAE addenda listed in Appendix H, Atlanta, Georgia. [cited by applicant]
Designation and Safety Classification of Refrigerants, ASHRAE Addenda, 2006 Supplement, ANSI/ASHRAE Addenda a, b, c, e, f, k, n, o, p, q, r, s and u to ANSI/ASHRAE Standard 34-2004, American Society of Heating, Refriger… [cited by applicant]
Designation and Safety Classification of Refrigerants, ASHRAE Standard, ANSI/ASHRAE Standard 34-2001 (Includes ANSI/ASHRAE Addenda listed in Appendix C), 2001, American Society of Heating, Refrigerating and Air-Conditio… [cited by applicant]
Designation and Safety Classification of Refrigerants, ASHRAE Standard, ANSI/ASHRAE Standard 34-2007 (Supersedes ANSI/ASHRAE Standard 34-2004), Includes ANSI/ASHRAE Addenda listed in Appendix F, 2007, American Society o… [cited by applicant]
Engineering ToolBox “Refrigerants—Common refrigerants—methane series, ethane series, propane series, cyclic organic compounds, zeotropic blends, azeotropic blends and organic compounds” Feb. 28, 2006 (Year: 2006). [cited by applicant]
International Search Report and Written Opinion for Application No. PCT/US2023/081363 mailed Mar. 20, 2024. [cited by applicant]
Lai, N. A., Thermodynamic properties of HFO-1243zf and their application in study on a refrigeration cycle, Applied Thermal Engineering 70, 2014, 1-6 (Year: 2014). [cited by applicant]
Lubricants in Refrigerant Systems, 1990 ASHRAE Handbook, Refrigeration Systems and Applications, Chapter 8, p. 8.1 8.21, Atlanta, GA. [cited by applicant]
PCT International Search Report and Written Opinion for Application No. PCT/US2019/057999 mailed Jan. 21, 2020. [cited by applicant]
PCT International Search Report and Written Opinion for Application No. PCT/US2020/029690 mailed Jul. 9, 2020. [cited by applicant]
PCT International Search Report and Written Opinion for Application No. PCT/US2021/029166 mailed Jul. 12, 2021. [cited by applicant]
Rached, Wissam, Expert Declaration dated Apr. 1, 2012 for U.S. Appl. No. 13/697,027, Arkema France. [cited by applicant]
Safety Standard for Refrigeration Systems, ANSI/ASHRAE Standard 15-2013 (Supersedes ANSIASHRAE Standard 15-2010), Includes ANSI/ASHRAE addenda listed in Appendix F, Atlanta, Georgia. [cited by applicant]
Saunders and Frisch, Polyurethanes Chemistry and Technology, 1962, pp. 193-201 and 219-223, vols. I and II, John Wiley and Sons, New York, NY. [cited by applicant]
Shubkin, Ronald L., Editor, Synthetic Lubricants and High Performance Functional Fluids, 1993, Chapter 2, Esters, pp. 43 65 and Chapter 4, Polyalkylene Glycols, pp. 101-123, Marcel Dekker, Inc., New York, NY. [cited by applicant]
Standard Test Method for Concentration Limits of Flammability of Chemicals (Vapors and Gases), ASTM E681-09, 2015. [cited by applicant]