Azeotropic and azeotrope-like compositions comprising a chlorinated compound and a cyclic c5- or c6-hydrocarbon

Abstract

The present invention relates to (i) an azeotropic or azeotrope-like composition comprising (1) a chlorinated compound selected from the group consisting of dichloromethane, 2-chloro-2-methylpropane, 1-chlorobutane, and 2-chlorobutane, and (2) a cyclic C5- or C6 hydrocarbon, selected from the group consisting of cyclopentane and methylcyclopentane, and (ii) a use of the azeotropic or azeotrope-like composition as solvent, cleaning or degreasing agent or as process fluid in processes such as flash spinning.

Description

[0001] TITLE

[0002] AZEOTROPIC AND AZEOTROPE-LIKE COMPOSITIONS COMPRISING A

[0003] CHLORINATED COMPOUND AND A CYCLIC C5- OR C6-HYDROCARBON

[0004] FIELD OF THE INVENTION

[0005] The present invention relates to (i) an azeotropic or azeotrope-like composition comprising (1) a chlorinated compound selected from the group consisting of dichloromethane, 2-chloro-2-methylpropane, 1 -chlorobutane, and 2-chlorobutane, and (2) a cyclic C5- or C6hydrocarbon, selected from the group consisting of cyclopentane and methylcyclopentane, and (ii) a use of the azeotropic or azeotrope-like composition as solvent, cleaning or degreasing agent, or process fluid in processes such as flash spinning.

[0006] BACKGROUND

[0007] Commercial processes that involve the use of solvents often employ mixtures of two or more different solvents to achieve solvent properties which may not be possible with one solvent alone. For example, while hydrocarbon solvents are chemically stable, available at low cost, and include a range of boiling points suitable for many processes, they have a very low polarity which limits their use as solvents. Accordingly, they may be blended with higher polarity solvents, such as chlorinated solvents, to achieve suitable solvent properties for the materials with which they are to be used.

[0008] In addition to solvent properties, the physical properties of solvent mixtures are also to be considered since they impact the process for recovering and re-using the solvents or solvent mixtures. For example, azeotropic or azeotrope-like compositions of two or more different solvents can be advantageous since they behave like a single substance in evaporation and distillation processes.

[0009] It is therefore advantageous to have a solvent composition of two or more solvents having different polarities that is also azeotropic or azeotrope-like. It is also beneficial if the atmospheric boiling points of such azeotropic or azeotrope-like compositions are above room temperature so that they can be stored and handled easily as liquids, but not so high that excessive heating and energy use is required to evaporate them. Such compositions are often useful as solvents, cleaning or degreasing agents, or process fluids for the processing of materials.

[0010] Azeotropic or azeotrope-like solvent compositions can be useful in a variety of different processes, including, but not limited to, flash spinning processes and recovery processes. For instance, in recovery processes, when using azeotrope or azeotrope-like solvent compositions as process fluids, the composition can be adjusted through multi-step distillation using successive distillation columns operating at different temperatures and pressures. This is useful, for example, in continuous processes where there is a desire to modify the process fluid composition for producing one product to that for producing another without stopping the process.

[0011] US 6,319,970 reports an azeotropic composition consisting of a mixture of 2,3- dihydrodecafluoropentane (HFC-4310mee), trans-1 ,2 dichloroethylene and cyclopentane as spin agents. However, the use of such linear hydrofluorocarbons in combination with DCM or DCE results in solvent mixtures that often exhibit undesirably high global warming potential (GWP).

[0012] US 7,309,458 suggests azeotropic or azeotrope-like compositions of cyclopentane and a compound selected from the group consisting of hydrofluorocarbons, hydrofluoroethers, or fluorinated sulfur compounds for different uses, such as refrigerants or cleaning agents. US 5,648,325 reports azeotropic or azeotrope-like solvent compositions comprising 1 H-perfluorohexane, methanol or ethanol, and optionally a hydrocarbon for removing soils from printed circuit boards. US 5,897,809 describes azeotropic or azeotrope-like compositions of 1 ,1 ,1 ,2,3,4,4,5,5,5-decafluoropentane and cyclohexane, or of 1 ,1 ,1 ,2,3,4,4,5,5,5-decafluoropentane, cyclohexane and acetone for different uses, such as cleaning agents or solvents. However, these solvent mixtures include major amounts of hydrofluorocarbons leading to undesirably high global warming potential (GWP).

[0013] In view of the growing concerns regarding climate change and increasing regulatory requirements, there is a need to find suitable low GWP replacements for solvents, cleaning or degreasing agents or process fluids disclosed in the prior art.

[0014] Accordingly, there is a need for, and the present inventors have discovered, low GWP azeotropic and azeotrope-like compositions of a chlorinated solvent and a cyclic hydrocarbon that (i) form a positive homogenous azeotrope with a boiling temperature below 70 °C, (ii) simplify the solvent recovery and re-use process, and (iii) allow the polarity to be adjusted over a broad range.

[0015] SUMMARY OF THE INVENTION

[0016] In one embodiment the invention is directed to an azeotropic or azeotrope-like composition comprising

[0017] (1) a chlorinated compound, selected from the group consisting of dichloromethane, 2-chloro-2-methylpropane, 1-chlorobutane, and 2-chlorobutane, and

[0018] (2) a cyclic C5- or C6hydrocarbon, selected from the group consisting of cyclopentane and methylcyclopentane.

[0019] BRIEF DESCRIPTION OF THE FIGURES

[0020] Fig. 1 shows the calculated vapor-liquid equilibrium (VLE) for compositions of dichloromethane (DCM) and cyclopentane at 40 °C.

[0021] Fig. 2 shows the calculated vapor-liquid equilibrium (VLE) for compositions of dichloromethane (DCM) and cyclopentane at 160 °C.

[0022] Fig. 3 shows the calculated vapor-liquid equilibrium (VLE) for compositions of 2- chloro-2-methylpropane and cyclopentane at 40 °C.

[0023] Fig. 4 shows the calculated vapor-liquid equilibrium (VLE) for compositions of 2- chloro-2-methylpropane and cyclopentane at 160 °C.

[0024] Fig. 5 shows the calculated vapor-liquid equilibrium (VLE) for compositions of

[0025] 1 -chlorobutane and methylcyclopentane at 40 °C.

[0026] Fig. 6 shows the calculated vapor-liquid equilibrium (VLE) for compositions of

[0027] 1-chlorobutane and methylcyclopentane at 160 °C.

[0028] Fig. 7 shows the calculated vapor-liquid equilibrium (VLE) for compositions of

[0029] 2-chlorobutane and methylcyclopentane at 40 °C.

[0030] Fig. 8 shows the calculated vapor-liquid equilibrium (VLE) for compositions of

[0031] 2-chlorobutane and methylcyclopentane at 160 °C.

[0032] DETAILED DESCRIPTION

[0033] Definitions and Clarification of Terms

[0034] Before addressing details of embodiments, some terms and test methods are defined or clarified. Unless otherwise mentioned, all tests were carried out without preconditioning of the samples. When average values are indicated herein, this refers to the arithmetic average.

[0035] The term “azeotropic composition’’ refers to a composition comprising two or more fluids wherein the bubble point pressure equals the dew point pressure. An azeotropic composition boils without change of the composition and behaves as a single substance. The azeotropic compositions described herein are determined in a temperature range of - 20 °C to 160 °C and expressed in mass fractions.

[0036] The term “azeotrope-like composition” refers to a composition comprising two or more fluids which exhibit only small differences between the dew point pressure and the bubble point pressure, i.e., the dew point pressure is different by 5% or less from the bubble point pressure (both expressed in absolute pressure). An azeotrope-like composition boils without substantial change of the composition and behaves substantially as a single substance. The azeotrope-like compositions described herein are determined in a temperature range of -20 °C to 160 °C and expressed in mass fractions.

[0037] Atmospheric pressure means 101.325 kPa. Essentially atmospheric pressure means 101.325 kPa ± 5 %.

[0038] The term “normal boiling point” refers to the temperature that is reached when the liquid vapor pressure equals 101.325 kPa (1 atm).

[0039] As used herein, the singular forms "a," "an," and "the" include the plural, and reference to a particular numerical value includes at least that particular value, unless the context clearly dictates otherwise. When a range of values is expressed, another embodiment includes from the one particular value and / or to the other particular value. Similarly, when values are expressed as approximations, by use of the antecedent "about," it will be understood that the particular value forms another embodiment. All ranges are inclusive and combinable.

[0040] Azeotropic or Azeotrope-like Compositions

[0041] Azeotropic or azeotrope-like compositions comprising dichloromethane and cyclopentane

[0042] Provided herein are azeotropic or azeotrope-like compositions comprising dichloromethane and cyclopentane.

[0043] In some embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent dichloromethane and from about 99 to about 1 weight percent cyclopentane, or from about 52 to about 95 weight percent dichloromethane and from about 48 to about 5 weight percent cyclopentane, or from about 52 to about 85 weight percent dichloromethane and from about 48 to about 15 weight percent cyclopentane. These azeotropic or azeotropelike compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 7 kPa to about 1926 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of or consist of from about 49 to about 99 weight percent dichloromethane and from about 51 to about 1 weight percent cyclopentane, or from about 58 to about 99 weight percent dichloromethane and from about 42 to about 1 weight percent cyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 7 kPa to about 593 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 55 to about 99 weight percent dichloromethane and from about 45 to about 1 weight percent cyclopentane, or from about 61 to about 99 weight percent dichloromethane and from about 39 to about 1 weight percent cyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 7 kPa to about 1 11 kPa.

[0044] In some embodiments, the composition comprising, consisting essentially of, or consisting of dichloromethane and cyclopentane is azeotropic.

[0045] In some embodiments, the azeotropic composition consists essentially of or consists of from about 67 to about 85 weight percent dichloromethane and from about 33 to about 15 weight percent cyclopentane. These azeotropic compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 7 kPa to about 1926 kPa.

[0046] In some embodiments, the azeotropic composition consists essentially of or consists of about 67.0 weight percent dichloromethane and about 33.0 weight percent cyclopentane at a pressure of about 7.7 kPa and at a boiling temperature of about -20 °C.

[0047] In some embodiments, the azeotropic composition consists essentially of or consists of about 72.0 weight percent dichloromethane and about 28.0 weight percent cyclopentane at a pressure of about 52.8 kPa and at a boiling temperature of about 20 °C.

[0048] In some embodiments, the azeotropic composition consists essentially of or consists of about 74.5 weight percent dichloromethane and about 25.5 weight percent cyclopentane at a pressure of about 1 10.9 kPa and at a boiling temperature of about 40 °C.

[0049] In some embodiments, the azeotropic composition consists essentially of or consists of about 76.5 weight percent dichloromethane and about 23.5 weight percent cyclopentane at a pressure of about 210 kPa and at a boiling temperature of about 60 °C.

[0050] In some embodiments, the azeotropic composition consists essentially of or consists of about 80.0 weight percent dichloromethane and about 20.0 weight percent cyclopentane at a pressure of about 593 kPa and at a boiling temperature of about 100 °C.

[0051] In some embodiments, the azeotropic composition consists essentially of or consists of about 84.5 weight percent dichloromethane and about 15.5 weight percent cyclopentane at a pressure of about 1926 kPa and at a boiling temperature of about 160 °C.

[0052] In some embodiments, the azeotropic composition consists essentially of or consists of about 74.2 weight percent dichloromethane and about 25.8 weight percent cyclopentane at a pressure of about 101 .3 kPa and at a boiling temperature of about 37.4 °C.

[0053] Azeotropic or azeotrope-like compositions comprising 2-chloro-2- methylpropane and cyclopentane

[0054] Provided herein are azeotropic or azeotrope-like compositions comprising 2-chloro- 2-methylpropane and cyclopentane.

[0055] In some embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 2-chloro-2- methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 10 to about 70 weight percent 2-chloro-2-methylpropane and from about 90 to about 30 weight percent cyclopentane, or from about 20 to about 60 weight percent 2-chloro-2- methylpropane and from about 80 to about 20 weight percent cyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 5 kPa to about 1426 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of or consist of from about 1 to about 99 weight percent 2-chloro-2-methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 15 to about 75 weight percent 2-chloro- 2-methylpropane and from about 85 to about 25 weight percent cyclopentane, or from about 25 to about 65 weight percent 2-chloro-2-methylpropane and from about 75 to about 35 weight percent cyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 5 kPa to about 433 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 2- chloro-2-methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 17 to about 77 weight percent 2-chloro-2-methylpropane and from about 83 to about 23 weight percent cyclopentane, or from about 27 to about 67 weight percent 2-chloro-2- methylpropane and from about 73 to about 33 weight percent cyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 5 kPa to about 79 kPa.

[0056] In some embodiments, the composition comprising, consisting essentially of, or consisting of 2-chloro-2-methylpropane and cyclopentane is azeotropic. In some embodiments, the azeotropic composition consists essentially of or consists of from about 33 to about 48 weight percent 2-chloro-2-methylpropane and from about 67 to about 52 weight percent cyclopentane. These azeotropic compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 5 kPa to about 1426 kPa.

[0057] In some embodiments, the azeotropic composition consists essentially of or consists of about 47.5 weight percent 2-chloro-2-methylpropane and about 52.5 weight percent cyclopentane at a pressure of about 5.4 kPa and at a boiling temperature of about -20 °C.

[0058] In some embodiments, the azeotropic composition consists essentially of or consists of about 47.5 weight percent 2-chloro-2-methylpropane and about 52.5 weight percent cyclopentane at a pressure of about 37.2 kPa and at a boiling temperature of about 20 °C.

[0059] In some embodiments, the azeotropic composition consists essentially of or consists of about 47.0 weight percent 2-chloro-2-methylpropane and about 53.0 weight percent cyclopentane at a pressure of about 78.8 kPa and at a boiling temperature of about 40 °C.

[0060] In some embodiments, the azeotropic composition consists essentially of or consists of about 46.0 weight percent 2-chloro-2-methylpropane and about 54.0 weight percent cyclopentane at a pressure of about 150 kPa and at a boiling temperature of about 60 °C.

[0061] In some embodiments, the azeotropic composition consists essentially of or consists of about 43.0 weight percent 2-chloro-2-methylpropane and about 57.0 weight percent cyclopentane at a pressure of about 433 kPa and at a boiling temperature of about 100 °C.

[0062] In some embodiments, the azeotropic composition consists essentially of or consists of about 33.5 weight percent 2-chloro-2-methylpropane and about 66.5 weight percent cyclopentane at a pressure of about 1426 kPa and at a boiling temperature of about 160 °C.

[0063] In some embodiments, the azeotropic composition consists essentially of or consists of about 46.9 weight percent 2-chloro-2-methylpropane and about 53.1 weight percent cyclopentane at a pressure of about 101.3 kPa and at a boiling temperature of about 47.5 °C. Azeotropic or azeotrope-like compositions comprising 1 -chlorobutane and methylcyclopentane

[0064] Provided herein are azeotropic or azeotrope-like compositions comprising 1- chlorobutane and methylcyclopentane.

[0065] In some embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 1 -chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 76 weight percent 1 -chlorobutane and from about 99 to about 24 weight percent methylcyclopentane, or from about 1 to about 56 weight percent 1 -chlorobutane and from about 99 to about 44 weight percent methylcyclopentane. These azeotropic or azeotropelike compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 1 kPa to about 849 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of or consist of from about 1 to about 99 weight percent 1 -chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 65 weight percent 1 -chlorobutane and from about 99 to about 35 weight percent methylcyclopentane, or from about 1 to about 48 weight percent 1 -chlorobutane and from about 99 to about 52 weight percent methylcyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 1 kPa to about 227 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 1- chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 48 weight percent 1 -chlorobutane and from about 99 to about 52 weight percent methylcyclopentane, or from about 1 to about 37 weight percent 1 -chlorobutane and from about 99 to about 63 weight percent methylcyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 1 kPa to about 34 kPa.

[0066] In some embodiments, the composition comprising, consisting essentially of, or consisting of 1 -chlorobutane and methylcyclopentane is azeotropic.

[0067] In some embodiments, the azeotropic composition consists essentially of or consists of from about 1 to about 18 weight percent 1 -chlorobutane and from about 99 to about 82 weight percent methylcyclopentane. These azeotropic compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 1 kPa to about 849 kPa.

[0068] In some embodiments, the azeotropic composition consists essentially of or consists of about 1.0 weight percent 1-chlorobutane and about 99.0 weight percent methylcyclopentane at a pressure of about 1.7 kPa and at a boiling temperature of about -20 °C.

[0069] In some embodiments, the azeotropic composition consists essentially of or consists of about 10.5 weight percent 1 -chlorobutane and about 89.5 weight percent methylcyclopentane at a pressure of about 14.8 kPa and at a boiling temperature of about 20 °C.

[0070] In some embodiments, the azeotropic composition consists essentially of or consists of about 14.0 weight percent 1 -chlorobutane and about 86.0 weight percent methylcyclopentane at a pressure of about 34.0 kPa and at a boiling temperature of about 40 °C.

[0071] In some embodiments, the azeotropic composition consists essentially of or consists of about 16.0 weight percent 1 -chlorobutane and about 84.0 weight percent methylcyclopentane at a pressure of about 69.8 kPa and at a boiling temperature of about 60 °C.

[0072] In some embodiments, the azeotropic composition consists essentially of or consists of about 18.0 weight percent 1 -chlorobutane and about 82.0 weight percent methylcyclopentane at a pressure of about 227 kPa and at a boiling temperature of about 100 °C.

[0073] In some embodiments, the azeotropic composition consists essentially of or consists of about 17.0 weight percent 1 -chlorobutane and about 83.0 weight percent methylcyclopentane at a pressure of about 849 kPa and at a boiling temperature of about 160 °C.

[0074] In some embodiments, the azeotropic composition consists essentially of or consists of about 17.0 weight percent 1 -chlorobutane and about 83.0 weight percent methylcyclopentane at a pressure of about 101 .3 kPa and at a boiling temperature of about 71.5 °C.

[0075] Azeotropic or azeotrope-like compositions comprising 2-chlorobutane and methylcyclopentane

[0076] Provided herein are azeotropic or azeotrope-like compositions comprising 2- chlorobutane and methylcyclopentane.

[0077] In some embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 2-chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 44 to about 99 weight percent 2-chlorobutane and from about 56 to about 1 weight percent methylcyclopentane, or from about 54 to about 94 weight percent 2-chlorobutane and from about 46 to about 6 weight percent methylcyclopentane. These azeotropic or azeotropelike compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 2 kPa to about 958 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of or consist of from about 1 to about 99 weight percent 2-chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 39 to about 99 weight percent 2-chlorobutane and from about 61 to about 1 weight percent methylcyclopentane, or from about 49 to about 89 weight percent 2-chlorobutane and from about 51 to about 11 weight percent methylcyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 2 kPa to about 257 kPa. In other embodiments, the azeotropic or azeotrope-like compositions comprise, consist essentially of, or consist of from about 1 to about 99 weight percent 2- chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 37 to about 97 weight percent 2-chlorobutane and from about 63 to about 3 weight percent methylcyclopentane, or from about 47 to about 87 weight percent 2-chlorobutane and from about 53 to about 13 weight percent methylcyclopentane. These azeotropic or azeotrope-like compositions boil at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 2 kPa to about 40 kPa.

[0078] In some embodiments, the composition comprising, consisting essentially of, or consisting of 2-chlorobutane and methylcyclopentane is azeotropic.

[0079] In some embodiments, the azeotropic composition consists essentially of or consists of from about 66 to about 82 weight percent 2-chlorobutane and from about 34 to about 18 weight percent methylcyclopentane. These azeotropic compositions boil at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 2 kPa to about 958 kPa.

[0080] In some embodiments, the azeotropic composition consists essentially of or consists of about 66.0 weight percent 2-chlorobutane and about 34.0 weight percent methylcyclopentane at a pressure of about 2.1 kPa and at a boiling temperature of about -20 °C.

[0081] In some embodiments, the azeotropic composition consists essentially of or consists of about 67.5 weight percent 2-chlorobutane and about 32.5 weight percent methylcyclopentane at a pressure of about 17.4 kPa and at a boiling temperature of about 20 °C.

[0082] In some embodiments, the azeotropic composition consists essentially of or consists of about 68.5 weight percent 2-chlorobutane and about 31.5 weight percent methylcyclopentane at a pressure of about 39.6 kPa and at a boiling temperature of about 40 °C.

[0083] In some embodiments, the azeotropic composition consists essentially of or consists of about 69.5 weight percent 2-chlorobutane and about 30.5 weight percent methylcyclopentane at a pressure of about 80.4 kPa and at a boiling temperature of about 60 °C.

[0084] In some embodiments, the azeotropic composition consists essentially of or consists of about 72.5 weight percent 2-chlorobutane and about 27.5 weight percent methylcyclopentane at a pressure of about 257 kPa and at a boiling temperature of about 100 °C.

[0085] In some embodiments, the azeotropic composition consists essentially of or consists of about 82.0 weight percent 2-chlorobutane and about 18.0 weight percent methylcyclopentane at a pressure of about 958 kPa and at a boiling temperature of about 160 °C.

[0086] In some embodiments, the azeotropic composition consists essentially of or consists of about 69.8 weight percent 2-chlorobutane and about 30.2 weight percent methylcyclopentane at a pressure of about 101 .3 kPa and at a boiling temperature of about 67.2 °C.

[0087] Properties of the azeotropic or azeotrope-like compositions

[0088] The compound dichloromethane (DCM) has a reported GWP-100 global (warming potential over a 100-year period) of 1 1.2 (IPCC 2021 report) and the compound 1- chlorobutane has a reported GWP-100 of 0.007 according to the same source. No calculated GWP values are available for 2-chlorobutane and 2-chloro-2-methylpropane. However, these compounds are expected to have a short atmospheric lifetime similar to 1- chlorobutane, so a GWP-100 of essentially zero may be also assumed for these compounds. While no specific data is available for cyclopentane or methylcyclopentane, values reported for hydrocarbons with up to four carbon atoms show a rapid decline in GWP-100 as the number of carbon atoms increases, so it is reasonable to assume a GWP- 100 of at or close to zero for these compounds.

[0089] Accordingly, the azeotropic or azeotrope-like compositions disclosed herein combining the chlorinated compounds dichloromethane, 2-chloro-2-methylpropane, 1- chlorobutane and 2-chlorobutane and cyclopentane or methylcyclopentane have a very low global warming potential (GWP).

[0090] In some embodiments, the azeotropic or azeotrope-like compositions comprising dichloromethane and cyclopentane have a GWP-100 of less than about 12, or less than about 10, or less than about 8, or less than about 5. The azeotropic or azeotrope-like compositions comprising 2-chloro-2-methylpropane, 1-chlorobutane or2-chlorobutane and cyclopentane or methylcyclopentane have a GWP-100 of at or close to zero.

[0091] The azeotropic or azeotrope-like compositions as described herein have the advantage of being homogeneous azeotropic or azeotrope-like compositions. For homogenous azeotropic or azeotrope-like compositions, the components of the composition at ambient temperatures and pressures form a single liquid phase. This is to be contrasted with heterogeneous azeotropic or azeotrope-like compositions, where, due to low miscibility of the components of the composition, the components of the composition undergo phase separation in the liquid phase. Phase separation is usually undesired since processes involving the composition are more complex and expensive. The homogeneous nature of the azeotropic or azeotrope-like compositions is achievable over a broad range of conditions, including at ambient pressure and temperature, and such compositions exhibit only small differences between the bubble point pressure and the dew point pressure. Thus, the azeotropic or azeotrope- like compositions do not change significantly during the recovery process and allow for the compositions to be re-used / recycled in a wide range of applications.

[0092] Uses of the azeotropic or azeotrope-like compositions

[0093] The azeotropic or azeotrope-like compositions are useful in a wide range of applications. In some embodiments, the azeotropic or azeotrope-like compositions are used as solvents, e.g., as solvents for applying coatings, or as cleaning or degreasing agents, e.g., for electronic components and circuit boards. In some embodiments, the azeotropic or azeotrope-like compositions are used as process fluids. In some embodiments, the azeotropic or azeotrope-like compositions are used as a process fluid in a process such as flash spinning, e.g., as a spin agent or as a process fluid in the solvent recovery process.

[0094] EXAMPLES

[0095] A study has been performed for the vapor-liquid equilibrium (VLE) for compositions of dichloromethane (DCM) and cyclopentane, 2-chloro-2-methylpropane and cyclopentane, 1-chlorobutane and methylcyclopentane, and 2-chlorobutane and methylcyclopentane. The experimental procedure and results are provided below. These examples are given to illustrate exemplary embodiments of the invention and should not be interpreted as limiting in any way. Materials Used

[0096] Dichloromethane (DCM), CAS Nr. of 75-09-2, has an atmospheric boiling point of 40 °C and a molecular weight of 84.93 g / mol. The dichloromethane used had a purity level above 99.9 percent by weight.

[0097] 2-Chloro-2-methylpropane (also known as tert-butyl chloride), CAS Nr. 507-20-0, has an atmospheric boiling point of 51 °C and a molecular weight of 92.57 g / mol. The 2- chloro-2-methylpropane used had a purity level above 99 percent by weight.

[0098] 1-Chlorobutane (also known as n-butyl chloride), CAS Nr. 109-69-3, has an atmospheric boiling point of 78 °C and a molecular weight of 92.57 g / mol. The

[0099] 1-chlorobutane used had a purity level above 99 percent by weight.

[0100] 2-Chlorobutane (also known as sec-butyl chloride), CAS Nr. 78-86-4, has an atmospheric boiling point of 68 °C and a molecular weight of 92.57 g / mol. The

[0101] 2-chlorobutane used had a purity level above 99 percent by weight.

[0102] Cyclopentane, CAS Nr. 287-92-3, has an atmospheric boiling point of 49°C and a molecular weight of 70.1 g / mol. The cyclopentane used had a purity level above 98 percent by weight.

[0103] Methylcyclopentane, CAS Nr. 96-37-7, has an atmospheric boiling point of 72 °C and a molecular weight of 84.16 g / mol. The methylcyclopentane used had a purity level above 97 percent by weight.

[0104] Results

[0105] Example 1 : Vapor liquid equilibrium for the composition of dichloromethane and cyclopentane

[0106] Figure 1 shows the calculated vapor liquid equilibrium for the composition of dichloromethane and cyclopentane at 40 °C. The azeotropic composition of dichloromethane and cyclopentane at 40 °C corresponds to about 74.5 wt% dichloromethane and about 25.5 wt% cyclopentane. The bubble point pressure for this azeotropic composition is equal to about 110.9 kPa. The azeotropic-like composition of dichloromethane and cyclopentane at a 5% deviation from the azeotrope point at 40 °C was found to be from about 55:45 wt% to about 99:1 wt%.

[0107] Figure 2 shows the calculated vapor liquid equilibrium for the composition of dichloromethane and cyclopentane at 160 °C. The azeotropic composition of dichloromethane and cyclopentane at 160 °C corresponds to about 84.5 wt% dichloromethane and about 15.5 wt% cyclopentane. The bubble point pressure for this azeotropic composition is equal to about 1926 kPa. The azeotropic-like composition of dichloromethane and cyclopentane at a 5% deviation from the azeotrope point at 160 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0108] Example 2: Vapor liquid equilibrium for the composition of 2-chloro-2- methylpropane and cyclopentane

[0109] Figure 3 shows the calculated vapor liquid equilibrium for the composition of 2- chloro-2-methylpropane and cyclopentane at 40 °C. The azeotropic composition of 2- chloro-2-methylpropane and cyclopentane at 40 °C corresponds to about 47.0 wt% 2- chloro-2-methylpropane and about 53.0 wt% cyclopentane. The bubble point pressure for this azeotropic composition is equal to about 78.8 kPa. The azeotropic-like composition of 2-chloro-2-methylpropane and cyclopentane at a 5% deviation from the azeotrope point at 40 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0110] Figure 4 shows the calculated vapor liquid equilibrium for the composition of 2- chloro-2-methylpropane and cyclopentane at 160 °C. The azeotropic composition of 2- chloro-2-methylpropane and cyclopentane at 160 °C corresponds to about 33.5 wt% 2- chloro-2-methylpropane and about 66.5 wt% cyclopentane. The bubble point pressure for this azeotropic composition is equal to about 1426 kPa. The azeotropic-like composition of 2-chloro-2-methylpropane and cyclopentane at a 5% deviation from the azeotrope point at 160 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0111] Example 3: Vapor liquid equilibrium for the composition of 1 -chlorobutane and methylcyclopentane

[0112] Figure 5 shows the calculated vapor liquid equilibrium for the composition of 1- chlorobutane and methylcyclopentane at 40 °C. The azeotropic composition of 1- chlorobutane and methylcyclopentane at 40 °C corresponds to about 14.0 wt% 1- chlorobutane and about 86.0 wt% methylcyclopentane. The bubble point pressure for this azeotropic composition is equal to about 34.0 kPa. The azeotropic-like composition of 1- chlorobutane and methylcyclopentane at a 5% deviation from the azeotrope point at 40 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0113] Figure 6 shows the calculated vapor liquid equilibrium for the composition of 1- chlorobutane and methylcyclopentane at 160 °C. The azeotropic composition of 1- chlorobutane and methylcyclopentane at 160 °C corresponds to about 17.0 wt% 1- chlorobutane and about 83.0 wt% methylcyclopentane. The bubble point pressure for this azeotropic composition is equal to about 849 kPa. The azeotropic-like composition of 1- chlorobutane and methylcyclopentane at a 5% deviation from the azeotrope point at 160 °C was found to be from about 1 :99 wt% to about 99:1 wt%. Example 4: Vapor liquid equilibrium for the composition of 2-chlorobutane and methylcyclopentane

[0114] Figure 7 shows the calculated vapor liquid equilibrium for the composition of 2- chlorobutane and methylcyclopentane at 40 °C. The azeotropic composition of 2- chlorobutane and methylcyclopentane at 40 °C corresponds to about 68.5 wt% 2- chlorobutane and about 31.5 wt% methylcyclopentane. The bubble point pressure for this azeotropic composition is equal to about 34.0 kPa. The azeotropic-like composition of 2- chlorobutane and methylcyclopentane at a 5% deviation from the azeotrope point at 40 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0115] Figure 8 shows the calculated vapor liquid equilibrium for the composition of 2- chlorobutane and methylcyclopentane at 160 °C. The azeotropic composition of 2- chlorobutane and methylcyclopentane at 160 °C corresponds to about 82.0 wt% 2- chlorobutane and about 18.0 wt% methylcyclopentane. The bubble point pressure for this azeotropic composition is equal to about 958 kPa. The azeotropic-like composition of 2- chlorobutane and methylcyclopentane at a 5% deviation from the azeotrope point at 160 °C was found to be from about 1 :99 wt% to about 99:1 wt%.

[0116] The azeotropic or azeotrope-like compositions as described in the examples herein exhibit a desirably low GWP value of below 12, or at or close to zero. This makes these compositions suitable as replacement for currently used solvent mixtures.

[0117] Furthermore, the azeotropic or azeotrope-like compositions form a positive homogenous azeotrope with an advantageously low boiling temperature of 70 °C. Such low boiling temperature correlates to a pressure around (or only slightly above) atmospheric pressure.

[0118] The azeotrope-like compositions exhibit only small differences between the bubble point pressure and the dew point pressure. Thus, the azeotropic or azeotrope-like compositions do not change significantly during the recovery process and allow the compositions to be re-used / recycled in a commercial process.

[0119] OTHER EMBODIMENTS

[0120] 1 . In some embodiments, the present application provides an azeotropic or azeotropelike composition comprising

[0121] (1) a chlorinated compound, selected from the group consisting of dichloromethane, 2-chloro-2-methylpropane, 1-chlorobutane, and 2-chlorobutane, and

[0122] (2) a cyclic C5- or C6hydrocarbon, selected from the group consisting of cyclopentane and methylcyclopentane.

[0123] 2. The azeotropic or azeotrope- like composition of embodiment 1 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent dichloromethane and from about 99 to about 1 weight percent cyclopentane, or from about 52 to about 95 weight percent dichloromethane and from about 48 to about 5 weight percent cyclopentane, or from about 52 to about 85 weight percent dichloromethane and from about 48 to about 15 weight percent cyclopentane.

[0124] 3. The azeotropic or azeotrope-like composition of embodiment 2 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 7 kPa to about 1926 kPa.

[0125] 4. The azeotropic or azeotrope-like composition of any one of embodiments 2 to 3 comprising, consisting essentially of, or consisting of from about 49 to about 99 weight percent dichloromethane and from about 51 to about 1 weight percent cyclopentane, or from about 58 to about 99 weight percent dichloromethane and from about 42 to about 1 weight percent cyclopentane.

[0126] 5. The azeotropic or azeotrope-like composition of embodiment 4 boiling at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 7 kPa to about 593 kPa.

[0127] 6. The azeotropic or azeotrope-like composition of any one of embodiments 2 to 5 comprising, consisting essentially of, or consisting of from about 55 to about 99 weight percent dichloromethane and from about 45 to about 1 weight percent cyclopentane, or from about 61 to about 99 weight percent dichloromethane and from about 39 to about 1 weight percent cyclopentane. 7. The azeotropic or azeotrope-like composition of embodiment 6 boiling at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 7 kPa to about 111 kPa.

[0128] 8. The azeotropic composition of any one of the embodiments 2 to 7 consisting essentially of or consisting of from about 67 to about 85 weight percent dichloromethane and from about 33 to about 15 weight percent cyclopentane.

[0129] 9. The azeotropic composition of embodiment 8 boiling at a temperature of about -20 °C to about 160 °C at a pressure of about 7 kPa to about 1926 kPa.

[0130] 10. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 67.0 weight percent dichloromethane and about 33.0 weight percent cyclopentane.

[0131] 11 . The azeotropic composition of embodiment 10 boiling at temperature of about -20 °C at a pressure of about 7.7 kPa.

[0132] 12. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 72.0 weight percent dichloromethane and about 28.0 weight percent cyclopentane.

[0133] 13. The azeotropic composition of embodiment 12 boiling at temperature of about 20 °C at a pressure of about 52.8 kPa.

[0134] 14. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 74.5 weight percent dichloromethane and about 25.5 weight percent cyclopentane.

[0135] 15. The azeotropic composition of embodiment 14 boiling at temperature of about 40 °C at a pressure of about 110.9 kPa.

[0136] 16. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 76.5 weight percent dichloromethane and about 23.5 weight percent cyclopentane. 17. The azeotropic composition of embodiment 16 boiling at temperature of about 60 °C at a pressure of about 210 kPa.

[0137] 18. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 80.0 weight percent dichloromethane and about 20.0 weight percent cyclopentane.

[0138] 19. The azeotropic composition of embodiment 18 boiling at temperature of about 100 °C at a pressure of about 593 kPa.

[0139] 20. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 84.5 weight percent dichloromethane and about 15.5 weight percent cyclopentane.

[0140] 21 . The azeotropic composition of embodiment 20 boiling at temperature of about 160 °C at a pressure of about 1926 kPa.

[0141] 22. The azeotropic composition of any one of the embodiments 2 to 9 consisting essentially of or consisting of about 74.2 weight percent dichloromethane and about 25.8 weight percent cyclopentane.

[0142] 23. The azeotropic composition of embodiment 22 boiling at temperature of about 37.4 °C at a pressure of about 101 .3 kPa.

[0143] 24. The azeotropic or azeotrope- like composition of embodiment 1 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2-chloro- 2-methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 10 to about 70 weight percent 2-chloro-2-methylpropane and from about 90 to about 30 weight percent cyclopentane, or from about 20 to about 60 weight percent 2-chloro-2- methylpropane and from about 80 to about 20 weight percent cyclopentane.

[0144] 25. The azeotropic or azeotrope-like composition of embodiment 24 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 5 kPa to about 1426 kPa. 26. The azeotropic or azeotrope-like composition of any one of embodiments 24 to 25 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2-chloro-2-methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 15 to about 75 weight percent 2-chloro-2-methylpropane and from about 85 to about 25 weight percent cyclopentane, or from about 25 to about 65 weight percent 2-chloro-2-methylpropane and from about 75 to about 35 weight percent cyclopentane.

[0145] 27. The azeotropic or azeotrope-like composition of embodiment 26 boiling at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 5 kPa to about 433 kPa.

[0146] 28. The azeotropic or azeotrope-like composition of any one of embodiments 24 to 27 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2-chloro-2-methylpropane and from about 99 to about 1 weight percent cyclopentane, or from about 17 to about 77 weight percent 2-chloro-2-methylpropane and from about 83 to about 23 weight percent cyclopentane, or from about 27 to about 67 weight percent 2-chloro-2-methylpropane and from about 73 to about 33 weight percent cyclopentane.

[0147] 29. The azeotropic or azeotrope-like composition of embodiment 28 boiling at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 5 kPa to about 79 kPa.

[0148] 30. The azeotropic composition of any one of the embodiments 24 to 29 consisting essentially of or consisting of from about 33 to about 48 weight percent 2-chloro-2- methylpropane and from about 67 to about 52 weight percent cyclopentane.

[0149] 31 . The azeotropic composition of embodiment 30 boiling at a temperature of about - 20 °C to about 160 °C at a pressure of about 5 kPa to about 1426 kPa.

[0150] 32. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 47.5 weight percent 2-chloro-2-methylpropane and about 52.5 weight percent cyclopentane. 33. The azeotropic composition of embodiment 32 boiling at temperature of about -20 °C at a pressure of about 5.4 kPa.

[0151] 34. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 47.5 weight percent 2-chloro-2-methylpropane and about 52.5 weight percent cyclopentane.

[0152] 35. The azeotropic composition of embodiment 34 boiling at temperature of about 20 °C at a pressure of about 37.2 kPa.

[0153] 36. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 47.0 weight percent 2-chloro-2-methylpropane and about 53.0 weight percent cyclopentane.

[0154] 37. The azeotropic composition of embodiment 36 boiling at temperature of about 40 °C at a pressure of about 78.8 kPa.

[0155] 38. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 46.0 weight percent 2-chloro-2-methylpropane and about 54.0 weight percent cyclopentane.

[0156] 39. The azeotropic composition of embodiment 38 boiling at temperature of about 60 °C at a pressure of about 150 kPa.

[0157] 40. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 43.0 weight percent 2-chloro-2-methylpropane and about 57.0 weight percent cyclopentane.

[0158] 41 . The azeotropic composition of embodiment 40 boiling at temperature of about 100 °C at a pressure of about 433 kPa.

[0159] 42. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 33.5 weight percent 2-chloro-2-methylpropane and about 66.5 weight percent cyclopentane. 43. The azeotropic composition of embodiment 42 boiling at temperature of about 160 °C at a pressure of about 1426 kPa.

[0160] 44. The azeotropic composition of any one of the embodiments 24 to 31 consisting essentially of or consisting of about 46.9 weight percent 2-chloro-2-methylpropane and about 53.1 weight percent cyclopentane.

[0161] 45. The azeotropic composition of embodiment 44 boiling at temperature of about 47.5 °C at a pressure of about 101 .3 kPa.

[0162] 46. The azeotropic or azeotrope- like composition of embodiment 1 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 1- chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 76 weight percent 1 -chlorobutane and from about 99 to about 24 weight percent methylcyclopentane, or from about 1 to about 56 weight percent 1 -chlorobutane and from about 99 to about 44 weight percent methylcyclopentane.

[0163] 47. The azeotropic or azeotrope-like composition of embodiment 46 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 1 kPa to about 849 kPa.

[0164] 48. The azeotropic or azeotrope-like composition of any one of embodiments 46 to 47 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 1 -chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 65 weight percent 1 -chlorobutane and from about 99 to about 35 weight percent methylcyclopentane, or from about 1 to about 48 weight percent 1- chlorobutane and from about 99 to about 52 weight percent methylcyclopentane.

[0165] 49. The azeotropic or azeotrope-like composition of embodiment 48 boiling at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 1 kPa to about 227 kPa.

[0166] 50. The azeotropic or azeotrope-like composition of any one of embodiments 46 to 49 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 1 -chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 1 to about 48 weight percent 1 -chlorobutane and from about 99 to about 52 weight percent methylcyclopentane, or from about 1 to about 37 weight percent 1- chlorobutane and from about 99 to about 63 weight percent methylcyclopentane.

[0167] 51. The azeotropic or azeotrope-like composition of embodiment 50 boiling at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 1 kPa to about 34 kPa.

[0168] 52. The azeotropic composition of any one of the embodiments 46 to 51 consisting essentially of or consisting of from about 1 to about 18 weight percent 1 -chlorobutane and from about 99 to about 82 weight percent methylcyclopentane.

[0169] 53. The azeotropic composition of embodiment 52 boiling at a temperature of about - 20 °C to about 160 °C at a pressure of about 1 kPa to about 849 kPa.

[0170] 54. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 1.0 weight percent 1 -chlorobutane and about 99.0 weight percent methylcyclopentane.

[0171] 55. The azeotropic composition of embodiment 54 boiling at temperature of about -20 °C at a pressure of about 1 .7 kPa.

[0172] 56. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 10.5 weight percent 1 -chlorobutane and about 89.5 weight percent methylcyclopentane.

[0173] 57. The azeotropic composition of embodiment 56 boiling at temperature of about 20 °C at a pressure of about 14.8 kPa.

[0174] 58. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 14.0 weight percent 1 -chlorobutane and about 86.0 weight percent methylcyclopentane.

[0175] 59. The azeotropic composition of embodiment 58 boiling at temperature of about 40 °C at a pressure of about 34.0 kPa. 60. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 16.0 weight percent 1 -chlorobutane and about 84.0 weight percent methylcyclopentane.

[0176] 61 . The azeotropic composition of embodiment 60 boiling at temperature of about 60 °C at a pressure of about 69.8 kPa.

[0177] 62. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 18.0 weight percent 1 -chlorobutane and about 82.0 weight percent methylcyclopentane.

[0178] 63. The azeotropic composition of embodiment 62 boiling at temperature of about 100 °C at a pressure of about 227 kPa.

[0179] 64. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 17.0 weight percent 1 -chlorobutane and about 83.0 weight percent methylcyclopentane.

[0180] 65. The azeotropic composition of embodiment 64 boiling at temperature of about 160 °C at a pressure of about 849 kPa.

[0181] 66. The azeotropic composition of any one of the embodiments 46 to 53 consisting essentially of or consisting of about 17.0 weight percent 1 -chlorobutane and about 83.0 weight percent methylcyclopentane.

[0182] 67. The azeotropic composition of embodiment 66 boiling at temperature of about 71.5 °C at a pressure of about 101 .3 kPa.

[0183] 68. The azeotropic or azeotrope- like composition of embodiment 1 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2- chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 44 to about 99 weight percent 2-chlorobutane and from about 56 to about 1 weight percent methylcyclopentane, or from about 54 to about 94 weight percent 2-chlorobutane and from about 46 to about 6 weight percent methylcyclopentane. 69. The azeotropic or azeotrope-like composition of embodiment 68 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 2 kPa to about 958 kPa.

[0184] 70. The azeotropic or azeotrope-like composition of any one of embodiments 68 to 69 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2-chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 39 to about 99 weight percent 2-chlorobutane and from about 61 to about 1 weight percent methylcyclopentane, or from about 49 to about 89 weight percent 2- chlorobutane and from about 51 to about 1 1 weight percent methylcyclopentane.

[0185] 71. The azeotropic or azeotrope-like composition of embodiment 70 boiling at a temperature of about -20 °C to about 100 °C and at a boiling pressure of about 2 kPa to about 257 kPa.

[0186] 72. The azeotropic or azeotrope-like composition of any one of embodiments 68 to 71 comprising, consisting essentially of, or consisting of from about 1 to about 99 weight percent 2-chlorobutane and from about 99 to about 1 weight percent methylcyclopentane, or from about 37 to about 97 weight percent 2-chlorobutane and from about 63 to about 3 weight percent methylcyclopentane, or from about 47 to about 87 weight percent 2- chlorobutane and from about 53 to about 13 weight percent methylcyclopentane.

[0187] 73. The azeotropic or azeotrope-like composition of embodiment 50 boiling at a temperature of about -20 °C to about 40 °C and at a boiling pressure of about 2 kPa to about 40 kPa.

[0188] 74. The azeotropic composition of any one of the embodiments 68 to 73 consisting essentially of or consisting of from about 66 to about 82 weight percent 2-chlorobutane and from about 34 to about 18 weight percent methylcyclopentane.

[0189] 75. The azeotropic composition of embodiment 74 boiling at a temperature of about - 20 °C to about 160 °C at a pressure of about 2 kPa to about 958 kPa.

[0190] 76. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 66.0 weight percent 2-chlorobutane and about 34.0 weight percent methylcyclopentane. 77. The azeotropic composition of embodiment 76 boiling at temperature of about -20 °C at a pressure of about 2.1 kPa.

[0191] 78. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 67.5 weight percent 2-chlorobutane and about 32.5 weight percent methylcyclopentane.

[0192] 79. The azeotropic composition of embodiment 78 boiling at temperature of about 20 °C at a pressure of about 17.4 kPa.

[0193] 80. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 68.5 weight percent 2-chlorobutane and about 31.5 weight percent methylcyclopentane.

[0194] 81 . The azeotropic composition of embodiment 80 boiling at temperature of about 40 °C at a pressure of about 39.6 kPa.

[0195] 82. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 69.5 weight percent 2-chlorobutane and about 30.5 weight percent methylcyclopentane.

[0196] 83. The azeotropic composition of embodiment 82 boiling at temperature of about 60 °C at a pressure of about 80.4 kPa.

[0197] 84. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 72.5 weight percent 2-chlorobutane and about 27.5 weight percent methylcyclopentane.

[0198] 85. The azeotropic composition of embodiment 84 boiling at temperature of about 100 °C at a pressure of about 257 kPa.

[0199] 86. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 82.0 weight percent 2-chlorobutane and about 18.0 weight percent methylcyclopentane. 87. The azeotropic composition of embodiment 86 boiling at temperature of about 160 °C at a pressure of about 958 kPa.

[0200] 88. The azeotropic composition of any one of the embodiments 68 to 75 consisting essentially of or consisting of about 69.8 weight percent 2-chlorobutane and about 30.2 weight percent methylcyclopentane.

[0201] 89. The azeotropic composition of embodiment 88 boiling at temperature of about 67.2 °C at a pressure of about 101 .3 kPa.

[0202] 90. In some embodiments, the present application provides a use of the azeotropic or azeotrope-like composition of any one of embodiments 1 to 89 as a solvent, or cleaning or degreasing agent.

[0203] 91. In some embodiments, the present application provides a use of the azeotropic or azeotrope-like composition of any one of embodiments 1 to 89 as a process fluid.

[0204] 92. The use of embodiment 91 , wherein the azeotropic or azeotrope-like composition of any one of embodiments 1 to 89 is used as a process fluid in flash spinning.

[0205] 93. The use of embodiment 92, wherein the azeotropic or azeotrope-like composition of any one of embodiments 1 to 89 is used as a spin agent or as a process fluid in the solvent recovery process.

[0206] While various embodiments of the present invention have been described above, it should be understood that they have been presented by way of example, and not limitation. It will be apparent to persons skilled in the relevant art(s) that various changes in form and detail can be made therein without departing from the spirit and scope of the present invention. Thus, it should be appreciated that, while the invention has been described with reference to the above exemplary embodiments, other embodiments are within the scope of the claims. Moreover, it should be understood that the exemplary embodiments described herein may be combined to form other embodiments. After reading the above description, it will be apparent to one skilled in the relevant art(s) how to implement the invention in alternative embodiments. Thus, the present invention should not be limited by any of the above-described exemplary embodiments.

Claims

CLAIMS1. An azeotropic or azeotrope- like composition consisting essentially of(1) a chlorinated compound, selected from the group consisting of dichloromethane, 2-chloro-2-methylpropane, 1-chlorobutane, and 2- chlorobutane, and(2) a cyclic C5- or C6hydrocarbon, selected from the group consisting of cyclopentane and methylcyclopentane.

2. The azeotropic or azeotrope-like composition of claim 1 consisting essentially of(1) dichloromethane and cyclopentane, or(2) 2-chloro-2-methylpropane and cyclopentane, or(3) 1-chlorobutane and methylcyclopentane, or(4) 2-chlorobutane and methylcyclopentane.

3. The azeotropic or azeotrope-like composition of claim 1 or 2 consisting essentially of from about 1 to about 99 weight percent dichloromethane and from about 99 to about 1 weight percent cyclopentane.

4. The azeotropic or azeotrope-like composition of claim 3 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 7 kPa to about 1926 kPa.

5. The azeotropic composition of claim 3 or 4 consisting essentially of from about 67 to about 85 weight percent dichloromethane and from about 33 to about 15 weight percent cyclopentane6. The azeotropic composition of claim 5 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 7 kPa to about 1926 kPa.

7. The azeotropic or azeotrope-like composition of claim 1 or 2 consisting essentially of from about 1 to about 99 weight percent 2-chloro-2-methylpropane and from about 99 to about 1 weight percent cyclopentane.

8. The azeotropic or azeotrope-like composition of claim 7 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 5 kPa to about 1426 kPa.

9. An azeotropic composition comprising from about 33 to about 48 weight percent 2- chloro-2-methylpropane and from about 67 to about 52 weight percent cyclopentane.

10. The azeotropic composition of claim 9 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 5 kPa to about 1426 kPa.

11. An azeotropic or azeotrope-like composition comprising from about 1 to about 99 weight percent 1 -chlorobutane and from about 99 to about 1 weight percent methylcyclopentane.

12. The azeotropic or azeotrope-like composition of claim 11 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 1 kPa to about 849 kPa.

13. The azeotropic composition of claim 11 or 12 comprising from about 1 to about 18 weight percent 1 -chlorobutane and from about 99 to about 82 weight percent methylcyclopentane.

14. The azeotropic composition of claim 13 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 1 kPa to about 849 kPa.

15. An azeotropic or azeotrope-like composition comprising from about 1 to about 99 weight percent 2-chlorobutane and from about 99 to about 1 weight percent methylcyclopentane.

16. The azeotropic or azeotrope-like composition of claim 15 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 2 kPa to about 958 kPa.

17. The azeotropic composition of claim 15 or 16 comprising from about 66 to about 82 weight percent 2-chlorobutane and from about 34 to about 18 weight percent methylcyclopentane.

18. The azeotropic composition of claim 17 boiling at a temperature of about -20 °C to about 160 °C and at a boiling pressure of about 2 kPa to about 958 kPa.

19. Use of the azeotropic or azeotrope-like composition of any one of claims 1 to 18 as a solvent, or cleaning or degreasing agent.

20. Use of the azeotropic or azeotrope-like composition of any one of claims 1 to 18 as a process fluid. 21 . The use of claim 20, wherein the azeotropic or azeotrope-like composition of any one of claims 1 to 18 is used in flash spinning.

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