IP Library Granted Patent US 6,951,835
Granted Patent B1
US 6,951,835 · App. 09/528,962 · Granted Oct 4, 2005

Azeotrope-like compositions of 1,1,1,3,3-pentafluorobutane

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Quick Facts
Patent No.
US 6,951,835
App. No.
09/528,962
Granted
Oct 4, 2005
Kind
B1
Abstract

Disclosed are binary azeotrope-like compositions consisting essentially of 1,1,1,3,3-pentafluorobutane (HFC-365mfc) and 1,1,1,2,3,4,4,5,5,5-decafluoropentane (HFC-43-10mee) or nonafluoromethoxybutane. The present invention further includes ternary or quaternary azeotrope-like compositions consisting essentially of 1,1,1,3,3-pentafluorobutane and 1,1,1,2,3,4,4,5,5,5-decafluoropentane or nonafluoromethoxybutane, and additionally trans-1,2-dichloroethylene, n-propyl bromide, acetone, methanol, ethanol or isopropanol.

Claims (57)

1. An azeotrope-like 1,1,1,3,3-pentafluorobutane-containing composition, wherein said composition is selected from the group consisting of:

(i) compositions consisting essentially of from about 1 to about 99 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane and from about 1 to about 99 weight percent 1,1,1,3,3-pentafluorobutane, wherein said composition has a vapor pressure of from about 58.6 kPa to about 100.9 kPa at a temperature of about 40° C.;

(ii) compositions consisting essentially of from about 1 to about 95 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 15 weight percent of methanol, wherein said composition has a vapor pressure of from about 72.9 kPa to about 113.2 kPa at a temperature of about 40° C.;

(iii) compositions consisting essentially of from about 1 to about 95 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 15 weight percent ethanol, wherein said composition has a vapor pressure of from about 72.2 kPa to about 105.5 kPa at a temperature of about 40° C.;

(iv) compositions consisting essentially of from about 1 to about 95 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 15 weight percent isopropanol, wherein said composition has a vapor pressure of from about 61.8 kPa to about 103.2 kPa at a temperature of about 40° C.;

(v) compositions consisting essentially of from about 1 to about 70 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 28 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent acetone, wherein said composition has a vapor pressure of from about 73.8 kPa to about 100.3 kPa at a temperature of about 40° C.;

(vi) compositions consisting essentially of from about 1 to about 80 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 66 weight percent trans-1,2-dichloroethylene, wherein said composition has a vapor pressure of from about 102.8 kPa to about 118.8 kPa at a temperature of about 40° C.;

(vii) compositions consisting essentially of from about 1 to about 60 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 50 weight percent trans-1,2-dichloroethylene and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 116.0 kPa to about 128.2 kPa at a temperature of about 40° C.;

(viii) compositions consisting essentially of from about 1 to about 60 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 40 weight percent trans-1,2-dichloroethylene and from about 1 to about 10 weight percent ethanol, wherein said composition has a vapor pressure of from about 107.1 kPa to about 118.5 kPa at a temperature of about 40° C.;

(ix) compositions consisting essentially of from about 1 to about 60 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 50 weight percent trans-1,2-dichloroethylene and from about 1 to about 10 weight percent isopropanol, wherein said composition has a vapor pressure of from about 104.9 kPa to about 114.9 kPa at a temperature of about 40° C.;

(x) compositions consisting essentially of from about 1 to about 80 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 49 weight percent n-propyl bromide, wherein said composition has a vapor pressure of from about 70.9 kPa to about 106.5 kPa at a temperature of about 40° C.;

(xi) compositions consisting essentially of from about 1 to about 70 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 35 weight percent n-propyl bromide, and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 89.9 kPa to about 117.0 kPa at a temperature of about 40° C.;

(xii) compositions consisting essentially of from about 1 to about 70 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 35 weight percent n-propyl bromide, and from about 1 to about 10 weight percent ethanol, wherein said composition has a vapor pressure of from about 85.8 kPa to about 108.3 kPa at a temperature of about 40° C.;

(xiii) compositions consisting essentially of from about 1 to about 70 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 35 weight percent n-propyl bromide, and from about 1 to about 10 weight percent isopropanol, wherein said composition has a vapor pressure of from about 78.7 kPa to about 105.1 kPa at a temperature of about 40° C.;

(xiv) compositions consisting essentially of from about 1 to about 67 and from about 92 to about 99 weight percent nonafluoromethoxybutane and from about 33 to about 99 and from about 1 to about 8 weight percent 1,1,1,3,3-pentafluorobutane, wherein said composition has a vapor pressure of from about 50.1 kPa to about 100.9 kPa at a temperature of about 40° C.;

(xv) compositions consisting essentially of from about 1 to about 90 weight percent nonafluoromethoxybutane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 15 weight percent of methanol, wherein said composition has a vapor pressure of from about 77.9 kPa to about 113.2 kPa at a temperature of about 40° C.;

(xvi) compositions consisting essentially of from about 1 to about 60 weight percent nonafluoromethoxybutane, from about 39 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent ethanol, wherein said composition has a vapor pressure of from about 82.7 kPa to about 105.3 kPa at a temperature of about 40° C.;

(xvii) compositions consisting essentially of from about 1 to about 60 weight percent nonafluoromethoxybutane, from about 39 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent isopropanol, wherein said composition has a vapor pressure of from about 82.1 kPa to about 103.1 kPa at a temperature of about 40° C.;

(xviii) compositions consisting essentially of from about 1 to about 98 weight percent nonafluoromethoxybutane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 98 weight percent acetone, wherein said composition has a vapor pressure of from about 52.1 kPa to about 100.3 kPa at a temperature of about 40° C.;

(xix) compositions consisting essentially of from about 1 to about 75 weight percent nonafluoromethoxybutane, from about 1 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 64 weight percent trans-1,2-dichloroethylene, wherein said composition has a vapor pressure of from about 93.4 kPa to about 118.7 kPa at a temperature of about 40° C.;

(xx) compositions consisting essentially of from about 1 to about 60 weight percent nonafluoromethoxybutane, from about 20 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 50 weight percent trans-1,2-dichloroethylene and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 113.1 kPa to about 127.8 kPa at a temperature of about 40° C.;

(xxi) compositions consisting essentially of from about 1 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 50 weight percent trans-1,2-dichloroethylene and from about 1 to about 10 weight percent ethanol, wherein said composition has a vapor pressure of from about 104.9 kPa to about 114.8 kPa at a temperature of about 40° C.;

(xxii) compositions consisting essentially of from about 1 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 35 weight percent trans-1,2-dichloroethylene and from about 1 to about 9 weight percent isopropanol, wherein said composition has a vapor pressure of from about 103.8 kPa to about 113.6 kPa at a temperature of about 40° C.;

(xxiii) compositions consisting essentially of from about 1 to about 50 weight percent nonafluoromethoxybutane, from about 30 to about 98 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 49 weight percent n-propyl bromide, wherein said composition has a vapor pressure of from about 90.7 kPa to about 106.6 kPa at a temperature of about 40° C.; and

(xxiv) compositions consisting essentially of from about 1 to about 70 weight percent nonafluoromethoxybutane, from about 10 to about 97 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 35 weight percent n-propyl bromide and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 93.4 kPa to about 118.0 kPa at a temperature of about 40° C., and

wherein after 50 weight percent of said composition has evaporated the vapor pressure of the remaining composition has changed by about 10 percent or less.

2. The azeotrope-like 1,1,1,3,3-pentafluorobutane-containing composition of claim 1 , said composition is selected from the group consisting of:

(i) compositions consisting essentially of from about 10 to about 90 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane and from about 10 to about 90 weight percent 1,1,1,3,3-pentafluorobutane, wherein said composition has a vapor pressure of from about 65.9 kPa to about 98.9 kPa at a temperature of about 40° C.;

(ii) compositions consisting essentially of from about 10 to about 40 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 50 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 100.1 kPa to about 112.2 kPa at a temperature of about 40° C.;

(iii) compositions consisting essentially of from about 10 to about 40 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 50 to about 89 weight percent 1,1,1,3,3-pentafluorobutane, from about 1 to about 10 weight percent ethanol, wherein said composition has a vapor pressure of from about 96.9 kPa to about 103.8 kPa at a temperature of about 40° C.;

(iv) compositions consisting essentially of from about 10 to about 40 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 50 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent isopropanol, wherein said composition has a vapor pressure of from about 92.5 kPa to about 101.1 kPa at a temperature of about 40° C.;

(v) compositions consisting essentially of from about 10 to about 40 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 50 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent acetone, wherein said composition has a vapor pressure of from about 85.6 kPa to about 95.1 kPa at a temperature of about 40° C.;

(vi) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane and from about 10 to about 45 weight percent trans-1,2-dichloroethylene, wherein said composition has a vapor pressure of from about 114.2 kPa to about 118.0 kPa at a temperature of about 40° C.;

(vii) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 50 weight percent 1,1,1,3,3-pentafluorobutane, from about 15 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent of methanol, wherein said composition has a vapor pressure of from about 116.0 kPa to about 128.2 kPa at a temperature of about 40° C.;

(viii) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 50 weight percent 1,1,1,3,3-pentafluorobutane, from about 15 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent ethanol, wherein said composition has a vapor pressure of from about 114.1 kPa to about 119.3 kPa at a temperature of about 40° C.;

(ix) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 10 to about 50 weight percent 1,1,1,3,3-pentafluorobutane, from about 15 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent isopropanol, wherein said composition has a vapor pressure of from about 109.1 kPa to about 116.7 kPa at a temperature of about 40° C.;

(x) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 30 to about 70 weight percent 1,1,1,3,3-pentafluorobutane and from about 10 to about 40 weight percent n-propyl bromide, wherein said composition has a vapor pressure of from about 91.1 kPa to about 106.3 kPa at a temperature of about 40° C.;

(xi) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 35 weight percent n-propyl bromide, and from about 1 to about 6 weight percent of methanol, wherein said composition has a vapor pressure of from about 98.8 kPa to about 110.8 kPa at a temperature of about 40° C.;

(xii) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 35 weight percent n-propyl bromide, and from about 1 to about 6 weight percent ethanol, wherein said composition has a vapor pressure of from about 93.8 kPa to about 103.3 kPa at a temperature of about 40° C.;

(xiii) compositions consisting essentially of from about 10 to about 50 weight percent 1,1,1,2,3,4,4,5,5,5-decafluoropentane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 35 weight percent n-propyl bromide, and from about 1 to about 6 weight percent isopropanol, wherein said composition has a vapor pressure of from about 89.6 kPa to about 99.1 kPa at a temperature of about 40° C.;

(xiv) compositions consisting essentially of from about 20 to about 60 weight percent nonafluoromethoxybutane and from about 40 to about 80 weight percent 1,1,1,3,3-pentafluorobutane, wherein said composition has a vapor pressure of from about 82.7 kPa to about 96.9 kPa at a temperature of about 40° C.;

(xv) compositions consisting essentially of from about 10 to about 40 weight percent nonafluoromethoxybutane, from about 50 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent of methanol, wherein said composition has a vapor pressure of from about 107.0 kPa to about 113.2 kPa at a temperature of about 40° C.;

(xvi) compositions consisting essentially of from about 10 to about 40 weight percent nonafluoromethoxybutane, from about 48 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 6 weight percent ethanol, wherein said composition has a vapor pressure of from about 92.0 kPa to about 102.2 kPa at a temperature of about 40° C.;

(xvii) compositions consisting essentially of from about 10 to about 40 weight percent nonafluoromethoxybutane, from about 48 to about 89 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 6 weight percent isopropanol, wherein said composition has a vapor pressure of from about 90.7 kPa to about 100.5 kPa at a temperature of about 40° C.;

(xviii) compositions consisting essentially of from about 10 to about 40 weight percent nonafluoromethoxybutane, from about 40 to about 80 weight percent 1,1,1,3,3-pentafluorobutane and from about 1 to about 10 weight percent acetone, wherein said composition has a vapor pressure of from about 88.0 kPa to about 96.3 kPa at a temperature of about 40° C.;

(xix) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 30 to about 70 weight percent 1,1,1,3,3-pentafluorobutane and from about 10 to about 40 weight percent trans-1,2-dichloroethylene, wherein said composition has a vapor pressure of from about 104.9 kPa to about 115.8 kPa at a temperature of about 40° C.;

(xx) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 15 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent of methanol, wherein said composition has a vapor pressure of from about 121.1 kPa to about 127.8 kPa at a temperature of about 40° C.;

(xxi) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent ethanol, wherein said composition has a vapor pressure of from about 104.9 kPa to about 114.8 kPa at a temperature of about 40° C.;

(xxii) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 45 weight percent trans-1,2-dichloroethylene and from about 1 to about 6 weight percent isopropanol, wherein said composition has a vapor pressure of from about 103.8 kPa to about 113.6 kPa at a temperature of about 40° C.;

(xxiii) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 30 to about 70 weight percent 1,1,1,3,3-pentafluorobutane and from about 10 to about 40 weight percent n-propyl bromide, wherein said composition has a vapor pressure of from about 90.7 kPa to about 106.6 kPa at a temperature of about 40° C.; and

(xxiv) compositions consisting essentially of from about 10 to about 50 weight percent nonafluoromethoxybutane, from about 20 to about 70 weight percent 1,1,1,3,3-pentafluorobutane, from about 12 to about 35 weight percent n-propyl bromide and from about 1 to about 6 weight percent of methanol, wherein said composition has a vapor pressure of from about 101.8 kPa to about 113.2 kPa at a temperature of about 40° C., and

wherein after 50 weight percent of said composition has evaporated, the vapor pressure of the remaining composition has changed by about 10 percent or less.

3. A process for cleaning a surface comprising:

a) contacting the surface with the composition of claims 1 or 2 , and

b) recovering the cleaned surface from the composition.

4. A process for producing refrigeration, comprising condensing a composition of claims 1 or 2 , and thereafter evaporating said composition in the vicinity of a body to be cooled.

5. A process for producing heat, comprising condensing a composition of claim 1 or 2 in the vicinity of a body to be heated, and thereafter evaporating said composition.

Assignments (6)
RELEASE OF PATENT SECURITY AGREEMENT AT R/F 54575-0391 Recorded Aug 12, 2025
From: KEYBANK NATIONAL ASSOCIATION
To: MICROCARE HOLDINGS, LLC; MICROCARE INTERCO, LLC; MICROCARE, LLC; ZYNON TECHNOLOGIES, LLC
Reel/Frame 072447/0167 →
SECURITY INTEREST Recorded Dec 8, 2020
From: ZYNON TECHNOLOGIES, LLC
To: KEYBANK NATIONAL ASSOCIATION
Reel/Frame 054575/0391 →
RELEASE OF SECURITY INTEREST Recorded Apr 4, 2018
From: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 045845/0913 →
SECURITY INTEREST Recorded Apr 4, 2018
From: THE CHEMOURS COMPANY FC, LLC
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 045846/0011 →
SECURITY AGREEMENT Recorded Jun 10, 2015
From: THE CHEMOURS COMPANY FC LLC; THE CHEMOURS COMPANY TT, LLC
To: JPMORGAN CHASE BANK, N.A.
Reel/Frame 035839/0675 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 15, 2015
From: E. I. DU PONT DE NEMOURS AND COMPANY
To: THE CHEMOURS COMPANY FC, LLC
Reel/Frame 035432/0023 →