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(12) United States Patent (10) Patent No.: US 8.444,874 B2 Singh Et Al

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(12) United States Patent (10) Patent No.: US 8.444,874 B2 Singh Et Al USOO8444874B2 (12) United States Patent (10) Patent No.: US 8.444,874 B2 Singh et al. (45) Date of Patent: May 21, 2013 (54) HEAT TRANSFER METHODS USING HEAT (51) Int. Cl. TRANSFER COMPOSITIONS CONTAINING C09K5/04 (2006.01) TRANS-1,3,3,3-TETRAFLUOROPROPENE (52) U.S. Cl. USPC ............................................................ 252A68 (75) Inventors: Rajiv R. Singh, Getzville, NY (US); (58) Field of Classification Search Hang T. Pham, Amherst, NY (US); USPC ...................................................... 252/67, 68 David P. Wilson, East Amherst, NY See application file for complete search history. (US); Raymond H. Thomas, Pendleton, NY (US); Mark W. Spatz, East (56) References Cited Amherst, NY (US); David A. Metcalf, Denver, CO (US) U.S. PATENT DOCUMENTS (73) Assignee: Honeywell International Inc., 3.35 A 8.8 East, al. Morristown, NJ (US) 2,889,379 A 6/1959 Ruh et al. 2.917480 A 12, 1959 Bailey et al. (*) Notice: Subject to any disclaimer, the term of this 5. A . 3. Mary patent is extended or adjusted under 35 - - w use U.S.C. 154(b) by 0 days. 3,085,918 A 4, 1963 Sherliker et al. (Continued) (21) Appl. No.: 11/850,028 FOREIGN PATENT DOCUMENTS 1-1. EP O398147 11, 1990 (22) Filed: Sep. 4, 2007 EP O644173 A1 5, 1993 (65) Prior Publication Data (Continued) US 2008/0099.190 A1 May 1, 2008 OTHER PUBLICATIONS O O Downing, Ralph C., “Fluorcarbon Refrigerants Handbook.” Prentice Related U.S. Application Data Hall, Chapter 3 (1988), pp. 17-34. (60) Division of application No. 1 1/475,605, filed on Jun. (Continued) 26, 2006, and a continuation-in-part of application No. 10/837,525, filed on Apr. 29, 2004, now Pat. No. Primary Examiner — John Hardee 7,279.45 1, which is a continuation-in-part of (74) Attorney, Agent, or Firm — Colleen D. Szuch application No. 10/694,273, filed on Oct. 27, 2003, now Pat. No. 7.534.366, and a continuation-in-part of (57) ABSTRACT application No. 10/694,272, filed on Oct. 27, 2003, now Pat. No. 7.230,146. Disclosed are methods of transferring heat to or from a fluid s or body comprising causing heat to be transferred to or from (60) Provisional application No. 60/693,853, filed on Jun. a composition comprising at least trans-1,3,3,3-tetrafluorpro 24, 2005, provisional application No. 60/421.236, pene. filed on Oct. 25, 2002, provisional application No. 60/421,435, filed on Oct. 25, 2002. 15 Claims, 1 Drawing Sheet US 8,444,874 B2 Page 2 U.S. PATENT DOCUMENTS 7,074,751 B2 * 7/2006 Singh et al. ................... 510,408 7,230,146 B2 6/2007 Merkel et al. 3,723,318 A 3/1973. Butler 7,248,809 B2 7/2007 Kim et al. 3.884.828 A 5/1975 Butler 7,279.451 B2 * 10/2007 Singh et al. ................... 510,412 4,465,786 A 8, 1984 Zimmer et al. 7,341,984 B2 * 3/2008 Wilson et al. ................. 510,408 4.755,316 A 7/1988 Magid et al. 7,413,674 B2 * 8/2008 Singh et al. ... 252/67 3. A 18 Sty al 7.465,698 B2* 12/2008 Wilson et al. 510,408 4.842,024 A 6, 1989 EMS. 7,524.805 B2 * 4/2009 Singh et al. .. 510,408 w 4 7.534,366 B2 * 5/2009 Singh et al. ..................... 252,68 2: A 168 E. al. 1 2003/O127115 A1 7/2003 Thomas et al. 5.533.49. A 7/1996 REEE,a 2004/0089839 A1 5/2004 Thomas et al. - - 4 an LJer Fuy et al. 2004/01 19047 A1 6/2004 Singh et al. SRA leg Shaya 2005/0054741 A1 3/2005 Zipfel et al. 5,616,275 A 4/1997 Chisolm et al. FOREIGN PATENT DOCUMENTS 5,679,875 A 10/1997 Aoyama et al. 5,714,083. A 2f1998 Turner EP O974571 1, 2000 5,736,063 A 4, 1998 Richard et al. EP 105.5439 11, 2000 5,744,052 A 4, 1998 Bivens EP 1191080 T 2002 5,788,886 A 8, 1998 Minor et al. GB 950876 2, 1964 5,986,151 A * 1 1/1999 Van Der Puy ................. 570/175 JP 04-110388 A 4f1992 6,013,609 A 1/2000 Katafuchi JP 2004.110388 4f1992 6,031,141 A * 2/2000 Mallikarjuna et al. ........ 57Of 136 RU 2O73058 C1 2/1997 6,041,621 A 3, 2000 Oslzewski et al. WO O2/46328 A2 6, 2002 6,111,150 A 8/2000 Sakyu et al. WO 2004/O37752 5, 2004 6,124,510 A * 9/2000 Elsheikh et al. .............. 57Of 156 WO 2004/037.913 5, 2004 6,176,102 B1 1/2001 Novak et al. WO 2005,1031.87 11, 2005 6,258,292 B1 7/2001 Turner WO 2005,103.188 11, 2005 6,260,380 B1* 7/2001 Arman et al. ................... 62.646 WO 2005,105947 11, 2005 6,274,779 B1 8/2001 Merkeletal. 6,300,378 B1 10/2001 Tapscott OTHER PUBLICATIONS 6,327,866 B1 3. S. et al Acura Service Bulletin No. 92-027, dated Sep. 29, 1992. g: R 38: E. Saunders and Frisch, Polyurethanes Chemistry and Technology, vol. 6,640.841 B2 11/2003 Thomas et al. XVI, Part I (Chemistry), pp. 219-223, and vol. XVI, Part II (Tech 6,783,691 B1 8, 2004 Bivens et al. nology), pp. 193-201 (John Wiley and Sons, New York, NY(1962)) 6,858,571 B2 2/2005 Pham et al. U.S. 6,972,271 B2 12/2005 Thomas et al. 6,991,744 B2 1/2006 Mahler et al. * cited by examiner U.S. Patent May 21, 2013 US 8,444,874 B2 US 8,444,874 B2 1. 2 HEAT TRANSFER METHODS USING HEAT like) as the working fluid in heat transfer systems, such as in TRANSFER COMPOSITIONS CONTAINING refrigeration and air-conditioning systems, has become dis TRANS-1,3,3,3-TETRAFLUOROPROPENE favored because of the ozone-depleting properties associated with many of Such compounds. There has thus been an This is a divisional application of U.S. patent application increasing need for new fluorocarbon and hydrofluorocarbon Ser. No. 1 1/475,605, filed Jun. 26, 2006, which claims the compounds and compositions that are attractive alternatives benefit of Provisional U.S. Application 60/693853, filed Jun. to the compositions heretofore used in these and other appli 24, 2005. This application is a continuation-in-part of U.S. cations. For example, it has become desirable to retrofit chlo patent application Ser. No. 10/837,525, filed Apr. 29, 2004, rine-containing refrigeration systems by replacing chlorine now U.S. Pat. No. 7,279.451, which is a continuation-in-part 10 containing refrigerants with non-chlorine-containing of U.S. patent application Ser. No. 10/694,273, filed Oct. 27, refrigerant compounds that will not deplete the oZone layer, 2003 now U.S. Pat. No. 7,534,366 which claims the benefit of such as hydrofluorocarbons (HFCs). Industry in general and Provisional Applications 60/421,236 and 60/421,435, both the heat transfer industry in particular are continually seeking filed on Oct. 25, 2002. U.S. patent application Ser. No. new fluorocarbon based mixtures that offer alternatives to, 10/837,525 is a continuation-in-part of U.S. patent applica 15 and are considered environmentally safer Substitutes for, tion Ser. No. 10/694,272, filed Oct. 27, 2003, now U.S. Pat. CFCs and HCFCs. It is generally considered important, how No. 7,230,146. ever, at least with respect to heat transfer fluids, that any potential Substitute must also possess those properties present FIELD OF THE INVENTION in many of the most widely used fluids, such as excellent heat transfer properties, chemical stability, low- or no-toxicity, This invention relates to compositions, methods and sys non-flammability and/or lubricant compatibility, among oth tems having utility in numerous applications, including par CS. ticularly heat transfer systems such as refrigeration systems. Applicants have come to appreciate that lubricant compat In preferred aspects, the present invention is directed to ibility is of particular importance in many of applications. refrigerant compositions which comprise at least one multi 25 More particularly, it is highly desirably for refrigeration fluids fluorinated olefin of the present invention. to be compatible with the lubricant utilized in the compressor unit, used in most refrigeration systems. Unfortunately, many BACKGROUND non-chlorine-containing refrigeration fluids, including HFCs, are relatively insoluble and/or immiscible in the types Fluorocarbon based fluids have found widespread use in 30 of lubricants used traditionally with CFCs and HFC's, many commercial and industrial applications, including as including, for example, mineral oils, alkylbenzenes or poly the working fluid in systems such as air conditioning, heat (alpha-olefins). In order for a refrigeration fluid-lubricant pump and refrigeration systems, as aerosol propellants, as combination to work at a desirable level of efficiently within blowing agents, as heat transfer media, and as gaseous dielec a compression refrigeration, air-conditioning and/or heat trics. Because of certain Suspected environmental problems, 35 pump system, the lubricant should be sufficiently soluble in including the relatively high global warming potentials, asso the refrigeration liquid over a wide range of operating tem ciated with the use of some of the compositions that have peratures. Such solubility lowers the viscosity of the lubricant heretofore been used in these applications, it has become and allows it to flow more easily throughout the system. In the increasingly desirable to use fluids having low or even Zero absence of such solubility, lubricants tend to become lodged oZone depletion potential.
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