Haloolefin composition

Abstract

To provide a haloolefin composition that is inhibited from decomposition and oxidation and has high stability.SOLUTION: The haloolefin composition includes (a) haloolefins, (b) at least one kind of compounds selected from the group consisting of HFO-1234ze, HFC-254eb, HFO-1243zf, HFC-245eb, HFC-245fa, HFC-245cb, HFC-236ea, HFC-236fa, HFO-1225ye, 3,3,3-trifluoropropyne, HFC-23, HFC-32, HFC-125, HFC-143a, HFC-134a, FC-1216, HCFO-1233xf, HCFO-1233zd, HCFO-1232xf, HCFO-1223xd and chloromethane, and (c) water.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a haloolefin composition. [Background technology]

[0002] Hydrofluorocarbons (HFCs), such as HFC-125 and HFC-32, are widely used as important alternatives to CFCs and HCFCs, which are known to destroy the ozone layer. Known alternatives include HFC-410A, a mixture of HFC-32 and HFC-125, and HFC-404A, a mixture of HFC-125, HFC-134a, and HFC-143a.

[0003] The above alternative substances are used in a wide variety of applications, such as heat transfer medium, refrigerant, foaming agent, solvent, cleaning agent, propellant, and fire extinguishing agent, and are consumed in large quantities. On the other hand, all of the above substances have a global warming potential (so-called "GWP") several thousand times that of CO2, and there are concerns that the diffusion of these substances will have a large impact on global warming. As a measure against global warming, substances are recovered after use, but not all of them can be recovered, and diffusion due to leakage, etc. cannot be ignored. In applications as refrigerants and heat transfer mediums, substitution with CO2 and hydrocarbon-based substances is being considered, but the efficiency of the CO2 refrigerant itself is low, and the equipment is also large, so there are many challenges in reducing the overall greenhouse gas emissions, including energy consumption. In addition, hydrocarbon-based substances have safety issues due to their high flammability.

[0004] As a substance that can solve the above problems, hydrohaloolefins, which have a low global warming potential, are currently attracting attention. Hydrohaloolefins is a general term for unsaturated hydrocarbons that contain hydrogen, fluorine, and chlorine, and includes, for example, substances represented by the following chemical formulas. The number in parentheses after the chemical formula indicates the refrigerant number that is generally used in refrigerant applications. CF3CF=CF2 (HFO-1216yc, also known as hexafluoropropene) CF3CF=CHF (HFO-1225ye) CF3CF=CH2(HFO-1234yf) CF3CH=CHF (HFO-1234ze) CF3CH=CH2(HFO-1243zf) CF3CCl=CH2(HCFO-1233xf) CF2ClCCl=CH2(HCFO-1232xf) CF3CH=CHCl(HCFO-1233zd) CF3CCl=CHCl(HCFO-1223xd) CClF2CCl=CHCl(HCFO-1222xd) CFCl2CCl=CH2(HCFO-1231xf) CH2ClCCl=CCl2(HCO-1230xa) Among these, fluoropropenes in particular are promising candidates for low GWP refrigerants and heat transfer media, but they are not particularly stable, as they may gradually decompose over time, etc. Therefore, when using such substances for various purposes, there are problems such as a gradual decrease in performance depending on the usage conditions or environment.

[0005] As a method for enhancing the stability of fluoropropenes, a method of adding a phenol compound to a composition containing HFO-1234yf and CF3I is known (see, for example, Patent Document 1, etc.). [Prior art documents] [Patent documents]

[0006] [Patent Document 1] International Publication No. 2005 / 103187 Summary of the Invention [Problem to be solved by the invention]

[0007] In the above-mentioned method, the stability of HFO-1234yf is improved by the action of the phenolic compound, but there are still problems in terms of handling during blending. In addition, in the above-mentioned method of improving stability by adding the phenolic compound, the action of the phenolic compound may cause the performance of the fluoropropene itself to decrease, and there are still problems in terms of improving stability while maintaining performance.

[0008] The present invention has been made in view of the above, and an object of the present invention is to provide a haloolefin composition which is highly stable and inhibits decomposition and oxidation. [Means for solving the problem]

[0009] As a result of intensive research into achieving the above-mentioned object, the present inventors have discovered that the above-mentioned object can be achieved by making a trace amount of water present in a mixture containing haloolefins and other specific substances, and have thus completed the present invention.

[0010] That is, the present invention relates to the following haloolefin composition. 1. (a) haloolefins; (b) at least one compound selected from the group consisting of HFO-1234ze, HFC-254eb, HFO-1243zf, HFC-245eb, HFC-245fa, HFC-245cb, HFC-236ea, HFC-236fa, HFO-1225ye, 3,3,3-trifluoropropyne, HFC-23, HFC-32, HFC-125, HFC-143a, HFC-134a, FC-1216, HCFO-1233xf, HCFO-1233zd, HCFO-1232xf, HCFO-1223xd, and chloromethane; (c) water; A haloolefin composition comprising: 2. The composition according to item 1, wherein the content of the (c) water is 200 ppm by weight or less based on the total amount of the (a) haloolefins. 3. The composition according to item 1 or 2, further comprising (d) oxygen. 4. The composition according to item 3, wherein the content of the (d) oxygen is 0.35 mol % or less based on the total amount of the (a) haloolefins. 5. The composition according to any one of items 1 to 4, wherein the (a) haloolefin is tetrafluoropropene. 6. The composition according to item 5, wherein the tetrafluoropropene is 2,3,3,3-tetrafluoropropene. 7. The composition according to item 5, wherein the tetrafluoropropene is 1,3,3,3-tetrafluoropropene. 8. The composition according to any one of items 1 to 7, further comprising (e) at least one of a polyalkylene glycol and a polyol ether. 9. (a) haloolefins, (c) water; (e) at least one of a polyalkylene glycol and a polyol ether; A haloolefin composition comprising: 10. The composition according to item 9, wherein the content of the (c) water is 200 ppm by weight or less based on the total amount of the (a) haloolefins. 11. The composition according to item 9 or 10, wherein the (a) haloolefin is tetrafluoropropene. 12. The composition according to item 11, wherein the tetrafluoropropene is 2,3,3,3-tetrafluoropropene. 13. The composition according to item 11, wherein the tetrafluoropropene is 1,3,3,3-tetrafluoropropene. Effect of the Invention

[0011] According to the haloolefin composition of the present invention, the stability of the haloolefins contained in the composition is improved by containing moisture. That is, the intramolecular double bonds of the haloolefins can be stably present, and the oxidation of the haloolefins is also unlikely to occur, so that the performance of the haloolefins is unlikely to be impaired for a long period of time. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] Hereinafter, an embodiment of the present invention will be described in detail.

[0013] The haloolefin composition contains (a) haloolefins, (b) at least one compound selected from the group consisting of HFO-1234ze, HFC-254eb, HFO-1243zf, HFC-245eb, HFC-245fa, HFC-245cb, HFC-236ea, HFC-236fa, HFO-1225ye, 3,3,3-trifluoropropyne, HFC-23, HFC-32, HFC-125, HFC-143a, HFC-134a, FC-1216, HCFO-1233xf, HCFO-1233zd, HCFO-1232xf, HCFO-1223xd, and chloromethane, which are by-products produced in the production of the haloolefins (hereinafter abbreviated as "component (b)"), and (c) water.

[0014] Here, HFO-1234ze is 1,3,3,3-tetrafluoropropene, and HFC-254eb is 1, 1,1,2-tetrafluoropropane, HFO-1243zf is 3,3,3-trifluoropropene, HFC-245eb is 1,1,1,2,3-pentafluoropropane, HFC-245fa is 1,1,1,3,3-pentafluoropropane, HFC-245cb is 1,1,1,2,2-pentafluoro propane, HFC-236ea is 1,1,1,2,3,3-hexafluoropropane, HFC-236fa is 1,1,1,3,3,3-hexafluoropropane, HFO-1225ye is 1,2,3,3,3-pentafluoropropene, HFC-23 is trifluoromethane, HFC-32 is methylene difluoride, HFC-125 is 1,1,1,2,2-pentafluoroethane, and HFC-143a is 1,1,1-trifluoromethane. Fluoroethane, HFC-134a is 1,1,1,2-tetrafluoroethane, FC-1216 is hexafluoroethane HCFO-1233xf is 2-chloro-3,3,3-trifluoropropene, HCFO-1233zd is 1-chloro-3,3,3-trifluoropropene, HCFO-1232xf is 3,3-difluoropropene 1,2-dichloro-3,3,3-trifluoropropene, HCFO-1223xd is 1,2-dichloro-3,3,3-trifluoropropene It is.

[0015] The component (b) is, for example, a by-product in the production of the haloolefins (a), and is therefore a compound different from the haloolefins (a).

[0016] The above-mentioned haloolefin composition (hereinafter sometimes abbreviated as "composition") contains moisture, which allows the intramolecular double bonds of the haloolefins to exist stably and also makes the haloolefins less susceptible to oxidation, thereby improving the stability of the haloolefins.

[0017] The above-mentioned haloolefins refer to unsaturated hydrocarbons having halogen atoms such as fluorine and chlorine as a substituent. In addition, all hydrogen atoms of the haloolefins may be replaced with halogen atoms, or some hydrogen atoms may be replaced with halogen atoms. The carbon number of the haloolefins is not particularly limited, but is, for example, 3 to 10 carbon atoms. The carbon number of the haloolefins is preferably 3 to 8, and particularly preferably 3 to 6, in terms of further increasing the stability of the haloolefins in the composition. The haloolefins contained in the composition may be only one type of compound, or may be two or more different types of compounds.

[0018] Particularly preferred haloolefins are tetrafluoropropene, pentafluoropropene, Examples of the haloolefins include 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,3,3,3-tetrafluoropropene (HFO-1234ze), 1,2,3,3-tetrafluoropropene (HFO-1234ye), 1,1,2,3-tetrafluoropropene (HFO-1234yc), 1,2,3,3,3-penta ... Examples include propene (HFO-1225ye), 1,1,3,3,3-pentafluoropropene (HFO-1225zc), 3,3,3-trifluoropropene (HFO-1243zf), 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz), 1,1,1,2,4,4,5,5,5-nonafluoropentene (HFO-1429myz), and the like.

[0019] The haloolefins can be those produced by known production methods. One example of such a production method is a method of dehydrofluorinating a fluoroalkane in the presence of a catalyst (for example, the method described in JP-A-2012-500182). The number of carbon atoms in the fluoroalkane is not particularly limited, but is preferably 3 to 8, and particularly preferably 3 to 6. For example, if the haloolefins are tetrafluoropropene, pentafluoropropane can be used as a raw material and dehydrofluorinated in the presence of a catalyst to produce tetrafluoropropene. Specifically, if the haloolefins are 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,1,1,2,3-pentafluoropropane or 1,1,1,2,2-pentafluoropropane can be used as a raw material and dehydrofluorinated in the presence of a catalyst to produce 2,3,3,3-tetrafluoropropene (HFO-1234yf). In addition, if the haloolefin is 1,3,3,3-tetrafluoropropene (HFO-1234ze), 1,3,3,3-tetrafluoropropene (HFO-1234ze) can be obtained by using 1,1,1,3,3-pentafluoropropane as a raw material and subjecting it to a dehydrofluorination reaction in the presence of a catalyst. In the above production method, a chromium catalyst such as chromium oxide or fluorinated chromium oxide, or other metal catalyst can be used as the catalyst, and the reaction temperature can be within the range of 200 to 500°C.

[0020] By the way, when 2,3,3,3-tetrafluoropropene is produced by the above-mentioned production method, E- and Z-forms of 1,3,3,3-tetrafluoropropene (HFO-1234ze) are produced as by-products. In this case, the by-products are usually removed by purifying the obtained product to obtain the target 2,3,3,3-tetrafluoropropene. However, the E- and Z-forms of 1,3,3,3-tetrafluoropropene produced as by-products by the above-mentioned production method are also components (b) in the composition. Therefore, when 2,3,3,3-tetrafluoropropene is produced by the above-mentioned method, the component (b), which is an essential component in the composition of this embodiment, is also obtained, so that it has the advantage that it can be used in a state containing the by-products without purification. Of course, not only 2,3,3,3-tetrafluoropropene but also other haloolefins are produced by the above-mentioned production method, as long as the by-products are also components (b), they can be used as haloolefins in the composition without purification. Therefore, when haloolefins are produced by a process in which a fluoroalkane is dehydrofluorinated in the presence of a catalyst, the haloolefins may contain by-products.

[0021] The component (b) in the composition is a compound selected from the group consisting of HFO-1234ze, HFC-254eb, HFO-1243zf, HFC-245eb, HFC-245fa, HFC-245cb, HFC-236ea, HFC-236fa, HFO-1225ye, 3,3,3-trifluoropropyne, HFC-23, HFC-32, HFC-125, HFC-143a, HFC-134a, FC-1216, HCFO-1233xf, HCFO-1233zd, HCFO-1232xf, HCFO-1223xd, and chloromethane, and may be one of these alone or two or more. When two or more are used, the combination is not particularly limited.

[0022] The component (b) may be one produced by a known production method, or, as described above, a by-product from the production of haloolefins may be used as the component (b).

[0023] The type of water is not particularly limited, and distilled water, ion-exchanged water, filtered water, tap water, and purified water such as ultrapure water obtained by a commercially available pure water generator can be used. However, if the water contains acids such as HCl, it may corrode the equipment or reduce the effect of stabilizing the haloolefins, so it is preferable to remove HCl and the like to a level below the detection limit in a commonly used analytical method. In this case, the content of the acids is preferably 10 ppm by weight or less, more preferably 1 ppm by weight or less, based on the total amount of the components (a), (b), and (c) contained in the composition.

[0024] There are no particular limitations on the pH of the water, but it is usually sufficient if it is within the range of 6 to 8. If the acid content in the water is within the above range, the pH of the water should usually be within this range.

[0025] The content of water contained in the composition is preferably 200 ppm by weight or less based on the total amount of (a) haloolefins. In this case, the effect of stabilizing the haloolefins is sufficiently exhibited. In addition, if the content of water is 200 ppm by weight or less based on the total amount of haloolefins, more preferably less than 30 ppm by weight, it is easy to prevent corrosion of equipment and promotion of decomposition of haloolefins. The lower limit of the content of water contained in the composition is not limited as long as the effect of the present invention is exhibited, but can be, for example, 0.1 ppm by weight, more preferably 3 ppm by weight. Within this range, the stability of the haloolefins in the composition is further improved.

[0026] The water content of the composition is particularly preferably more than 3 ppm by weight and less than 30 ppm by weight, in which case the stability of the haloolefins in the composition is further improved. In addition, by having the water content of the composition be less than 30 ppm by weight, the refrigerant performance is prevented from being impaired.

[0027] The content of component (b) in the composition is preferably 0.1 ppm by weight or more and less than 10,000 ppm by weight based on the total amount of haloolefins. Within this range, there is little risk of the stabilizing effect of the haloolefins being impaired.

[0028] The composition may contain other known additives to the extent that the effects of the present invention are not impaired. The amount of other additives is preferably 50% by weight or less, more preferably 40% by weight or less, based on the total amount of the composition.

[0029] The method for preparing the composition is not particularly limited. For example, each component is prepared and then mixed in a predetermined amount to obtain the composition.

[0030] In the above composition, the presence of water allows the double bonds of the haloolefins to be stable and oxidation is unlikely to occur, so the stability of the haloolefins is high. Therefore, the composition can be stored for a longer period of time than normal haloolefins. Moreover, the high stability of the haloolefins means that there is little risk of the performance of the haloolefins being impaired. Therefore, for example, even if the composition is used as a refrigerant or heat transfer medium, the high stability of the haloolefins means that the composition has excellent performance as a refrigerant or heat transfer medium.

[0031] The composition may further contain (d) oxygen. When the composition contains (d) oxygen, the content of (d) oxygen is 0.35 mol % or less based on the total amount of (a) haloolefins. It is preferable that the oxygen content is within this range. If the oxygen content is within this range, the stability of the haloolefins in the composition is further improved. From this viewpoint, the lower the oxygen content in the composition, the more preferable it is. However, since the composition contains water as described above, if the oxygen content is within the above range, the stability of the haloolefins can be maintained by the action of the water. The lower limit of the oxygen content in the composition can be, for example, 1 ppm, which is the detection limit of gas chromatography.

[0032] When the composition is used as a refrigerant or heat transfer medium as described above, the haloolefins particularly advantageously used are 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,3,3,3-tetrafluoropropene (HFO-1234ze), 1,2,3,3-tetrafluoropropene (HFO-1234ye), 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 3,3,3-trifluoropropene (HFO-1243zf), and the like.

[0033] When the composition is used as a refrigerant or heat transfer medium, the composition may contain at least one of (e) polyalkylene glycol and polyol ether as a lubricant. When the composition contains at least one of polyalkylene glycol and polyol ether, the above component (b) may be contained in the composition, or the above component (b) may not be contained in the composition. When the above component (b) is not contained in the composition, the composition comprises (a) haloolefins, (c) water, and (e) at least one of polyalkylene glycol and polyol ether. The (a) haloolefins and (c) water have the same configuration as described above.

[0034] The lubricating oil can be contained in an amount of 10 to 50 mass% based on the total amount of the components (a), (b) and (c) contained in the composition, but is not particularly limited to this range because it varies depending on the specifications of the oil tank of the refrigerator. Within this range, there is no risk of the stability of the haloolefins being impaired. In addition, the lubricating oil may further contain polyvinyl ether (PVE) or may be composed of polyvinyl ether alone.

[0035] An example of the polyalkylene glycol (PAG) is "SUNICE P56" manufactured by Nippon Sun Oil Co., Ltd. An example of the polyol ether (POE) is "Ze-GLES RB32" manufactured by JX Nippon Oil & Energy Corporation.

[0036] Even when the composition contains a lubricating oil, the composition may contain (d) oxygen. When the composition contains (d) oxygen, the content of (d) oxygen is preferably 0.35 mol% or less based on the total amount of (a) haloolefins, for the same reasons as described above.

[0037] Refrigerants and heat transfer media containing haloolefins as the main component are prone to decomposition or oxidation when they come into contact with metals, etc., and their performance as refrigerants or heat transfer media is easily impaired. However, when the above-mentioned composition is used as a refrigerant or heat transfer media, the high stability of the haloolefins prevents the performance of the refrigerant or heat transfer media from deteriorating.

[0038] Therefore, the composition according to the present invention can be used not only for the above-mentioned refrigerant or heat transfer medium applications, but also for various other applications. When the composition is used for such applications, specific examples of haloolefins include 2,3,3,3-tetrafluoropropene (HFO-1234yf), 1,3,3,3-tetrafluoropropene (HFO-1234ze), 1,2,3,3-tetrafluoropropene (HFO-1234ye), 1,1,2,3-tetrafluoropropene (HFO-1234yc), 1,2,3,3,3-pentafluoropropene (HFO-1225ye), 1,1,3,3,3-pentafluoropropene (HFO-1225 zc), 3,3,3-trifluoropropene (HFO-1243zf), 1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336mzz), 1,1,1,2,4,4,5,5,5-nonafluoropentene (HFO-1429myz), and the like. EXAMPLES

[0039] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the embodiments of these examples. It is not something that can be determined.

[0040] Example 1 2,3,3,3-tetrafluoropropene (hereinafter abbreviated as "HFO-1234yf") and water were prepared and mixed to prepare three types of haloolefin compositions with water contents of 10 ppm by weight, 200 ppm by weight, and 10000 ppm by weight relative to HFO-1234yf. The above HFO-1234yf was produced by a method such as that shown in Example 1 of JP-A-2012-500182 and JP-A-2009-126803. The HF produced at this time was deacidified using a water washing tower and an alkali tower containing an aqueous NaOH solution. The obtained haloolefin composition may contain by-products (for example, 1,3,3,3-tetrafluoropropene (HFO-1234ze), i.e., component (b)) produced in the production of HFO-1234yf.

[0041] Example 2 1,3,3,3-tetrafluoropropene (hereinafter abbreviated as "HFO-1234ze") and water were prepared and mixed to prepare three types of haloolefin compositions with water contents of 10 ppm by weight, 200 ppm by weight, and 10,000 ppm by weight relative to HFO-1234ze. Note that the above HFO-1234ze can be obtained by, for example, removing HF from HFC-245eb as described in JP 2012-500182 A. The resulting HF was deacidified in a water washing tower and an alkaline tower using an aqueous NaOH solution. HFO-1234yf is the component in (b).

[0042] Comparative Example 1 A haloolefin composition was obtained in the same manner as in Example 1, except that no water was added.

[0043] Comparative Example 2 A haloolefin composition was obtained in the same manner as in Example 2, except that water was not blended.

[0044] (Stability test of haloolefins 1) For each of the haloolefin compositions obtained in the above Examples and Comparative Examples, a stability test of haloolefins was carried out as follows. A haloolefin composition was added to a glass tube (ID 8 mmΦ x OD 12 mmΦ x L 300 mm) with one side heat-sealed so that the content of haloolefins was 0.01 mol. The tube was sealed by heat-sealing. The tube was placed in a thermostatic chamber under an atmosphere of 150°C and kept in this state for one week. Thereafter, the tube was removed from the thermostatic chamber and cooled, and the acid content in the gas in the tube was analyzed to evaluate the stability of the haloolefins.

[0045] (Stability test of haloolefins 2) For each of the haloolefin compositions obtained in the above Examples and Comparative Examples, a stability test for haloolefins was carried out as follows. A haloolefin composition was added to a tube (OD12mmΦ×L300mm) so that the content of haloolefins was 0.01 mol. Then, oxygen was sealed in the tube by adjusting the oxygen concentration to a predetermined molar concentration (0.010 mol%, 0.115 mol% or 0.345 mol%) relative to the number of moles of haloolefins filled. The tube was placed in a thermostatic chamber under an atmosphere of 150°C and kept in this state for one week. After that, the tube was removed from the thermostatic chamber and cooled, and the acid content in the gas in the tube was analyzed to evaluate the stability of the haloolefins.

[0046] The analysis of the acid content in the gas was carried out as follows. After cooling, the tube was filled with liquid nitrogen to completely solidify the gas remaining in the tube. The tube was then opened and gradually thawed, and the gas was collected in a Tedlar bag. 5 g of pure water was poured into the Tedlar bag, and the acid content was extracted into the pure water while being in close contact with the collected gas. The extracted solution was detected by ion chromatography to detect fluoride ions (F - ) and trifluoroacetate ion (CF3COO - ) content (ppm by weight) was measured.

[0047] The test results are shown in Table 1. In Table 1, "yf" and "ze(E)" represent "HFO-1234yf" and "HFO-1234ze," respectively. The (E) in "ze(E)" indicates that HFO-1234ze is the E form.

[0048] [Table 1]

[0049] Nos. 5 to 8 in Table 1 all have an oxygen addition amount of 0.010 mol %, but No. 5 is a composition that does not contain water, and therefore has a higher acid content than Nos. 6 to 8, which contain water. In other words, No. 5 has a higher acid content, which is likely to cause decomposition and oxidation of the haloolefin HFO-1234yf compared to Nos. 6 to 8. It can be seen that the decomposition is promoted compared to that in the case of the composition containing water. From this result, it can be seen that the haloolefin HFO-1234yf is stabilized in the composition containing water. In addition, the amount of oxygen added in Nos. 9 to 12 is 0.115 mol %, and the amount of oxygen added in Nos. 13 to 16 is 0.345 mol %, but the same tendency was observed as in the case of the amount of oxygen added being 0.115 mol %. Furthermore, the same tendency was observed in the case of the haloolefin HFO-1234ze (Nos. 21 to 24, 25 to 28, 29 to 32). In addition, in Nos. 1 to 4 and Nos. 17 to 20, the acid content is below 1 ppm by weight, and it can be seen that the decomposition of the haloolefins has hardly progressed. This is thought to be because no oxidation or the like occurred because no oxygen was added to the system. Therefore, in a system in which there is almost no oxygen, all haloolefins are stable regardless of whether water is included in the composition or not.

[0050] From the above, it is clear that the water contained in the composition of the present invention stabilizes the haloolefins.

Claims

1. (a) haloolefins; (b) at least one compound selected from the group consisting of HFO-1234ze, HFC-254eb, HFO-1243zf, HFC-245eb, HFC-245fa, HFC-245cb, HFC-236ea, HFC-236fa, HFO-1225ye, 3,3,3-trifluoropropyne, HFC-23, HFC-32, HFC-125, HFC-143a, HFC-134a, FC-1216, HCFO-1233xf, HCFO-1233zd, HCFO-1232xf, HCFO-1223xd, and chloromethane; (c) water; A haloolefin composition comprising:

2. The composition according to claim 1, wherein the content of said (c) water is 200 ppm by weight or less based on the total amount of said (a) haloolefins.

3. The composition according to claim 1 or 2, further comprising (d) oxygen.

4. The composition according to claim 3, wherein the content of said (d) oxygen is 0.35 mol % or less based on the total amount of said (a) haloolefins.

5. The composition according to any one of claims 1 to 4, wherein the (a) haloolefin is tetrafluoropropene.

6. The composition of claim 5, wherein the tetrafluoropropene is 2,3,3,3-tetrafluoropropene.

7. The composition of claim 5, wherein the tetrafluoropropene is 1,3,3,3-tetrafluoropropene.

8. The composition according to any one of claims 1 to 7, further comprising (e) at least one of a polyalkylene glycol and a polyol ether.

9. (a) haloolefins; (c) water; (e) at least one of a polyalkylene glycol and a polyol ether; A haloolefin composition comprising:

10. The composition according to claim 9, wherein the content of the (c) water is 200 ppm by weight or less based on the total amount of the (a) haloolefins.

11. The composition according to claim 9 or 10, wherein the (a) haloolefin is tetrafluoropropene.

12. The composition of claim 11, wherein the tetrafluoropropene is 2,3,3,3-tetrafluoropropene.

13. The composition of claim 11, wherein the tetrafluoropropene is 1,3,3,3-tetrafluoropropene.

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