WO2016129319A1 - Composition de type azéotrope comprenant une oléfine contenant du fluor comme constituant - Google Patents

Composition de type azéotrope comprenant une oléfine contenant du fluor comme constituant Download PDF

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WO2016129319A1
WO2016129319A1 PCT/JP2016/050904 JP2016050904W WO2016129319A1 WO 2016129319 A1 WO2016129319 A1 WO 2016129319A1 JP 2016050904 W JP2016050904 W JP 2016050904W WO 2016129319 A1 WO2016129319 A1 WO 2016129319A1
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composition
azeotropic
liquid
mol
azeotrope
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PCT/JP2016/050904
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Japanese (ja)
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井村　英明
高田　直門
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セントラル硝子株式会社
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/50—Solvents

Definitions

  • the present invention relates to a novel composition containing a fluorine-containing olefin.
  • CFCs chlorofluorocarbons
  • HFCs hydrochlorofluorocarbons
  • HFCs hydrofluorocarbons
  • Fluorine-containing alkanes have volatility, stability, and non-flammability characteristics, and have contributed to industrial development in applications such as refrigerants, working fluids, foaming agents, sprays, cleaning agents, solvents, and solvents.
  • chlorofluorocarbons sometimes called chlorofluorocarbons.
  • blending a plurality of fluorine-containing alkanes has been widely performed.
  • refrigerant numbers R502, R507A, R404A, R407C, and R410A from the American Society of Heating, Refrigerating and Air Conditioning Engineers (ASHRAE) are widely used as mixed refrigerants. These mixed refrigerants are improved in coefficient of performance, refrigeration cycle, incombustibility, global warming coefficient and the like by mixing two or more kinds of chlorofluorocarbons at a specific ratio.
  • fluorine-containing alkane has volatility, when one of the components evaporates unilaterally when used as a mixture, the composition changes during use and the physical properties change. Therefore, an azeotropic or azeotropic-like composition that volatilizes at substantially the same composition as the liquid phase is preferable.
  • R502 mixed refrigerant of R22 and R115
  • R507A mixed refrigerant of R143a and R125
  • R410A its constituent components R32 and R125 are non-azeotropic, but since the composition of the gas phase part and the liquid phase part is substantially the same, practically like the azeotropic composition. Since it can be handled, it is used as an azeotropic refrigerant.
  • blending fluorine-containing alkanes and alcohol for use as a draining agent for use as a draining agent, adding non-flammable fluorine-containing alkanes to flammable hydrocarbon solvents to make them nonflammable, or cleaning with controlled detergency
  • an agent for use of a cleaning agent or a draining agent, an azeotropic or azeotrope-like composition in which the composition of the gas phase part and the liquid phase part when volatilized is substantially the same as the refrigerant is preferable.
  • Fluorine-containing alkanes as described above are very stable in the atmosphere, have a long atmospheric lifetime, and are considered to cause global warming.
  • fluorine-containing olefins having 2 to 5 carbon atoms referring to hydrofluoroolefins, hydrochlorofluoroolefins, chlorofluoroolefins, and fluoroolefins
  • fluorine-containing olefins having a double bond in the molecule are significantly more reactive with OH radicals in the atmosphere than fluorine-containing alkanes having no double bond.
  • HFC-365mfc, HFC-245fa, HFC-43-10, etc. which are widely used, is in units of years, while the atmospheric lifetime of fluorine-containing olefins is generally in units of days. Even when released into the atmosphere, it decomposes quickly, so its impact on global warming and ozone depletion is low. It has been reported that since it has physical properties similar to the above-mentioned fluorinated alkanes, it can be used in various applications such as refrigerants, working fluids, foaming agents, sprays, cleaning agents, solvents and solvents.
  • Fluorine-containing olefins may improve performance by blending with other chemical species.
  • Patent Document 1 when (Z) -1-chloro-3,3,3-trifluoropropene and 1,1,2,2-tetrafluoro-1-methoxyethane are mixed, It is reported that a binary solvent is formed and the cleaning performance of various oils possessed by the binary solvent is at an excellent level. There are few report examples of this compared with fluorine-containing alkane. Furthermore, there are even fewer literature examples of azeotropic or azeotrope-like compositions in which fluorine-containing olefins are combined.
  • the low-boiling component in the cleaning liquid may decrease over time, resulting in poor cleaning.
  • the used cleaning solution is usually regenerated and reused by distillation. If the composition of the liquid phase is different from the composition of the gas phase, the liquid composition of the recovered composition must be adjusted. Not efficient. Further, when the composition is volatilized during use and the composition of the liquid is changed, not only the cleaning performance is changed, but the incombustible composition may be changed to a combustible composition.
  • an azeotropic or azeotrope-like composition in which the composition of the gas phase part and the liquid phase part is substantially the same during volatilization is strongly desired.
  • the Z form of 1-chloro-3,3,3-trifluoropropene (hereinafter sometimes referred to as HCFO-1233zd (Z) or 1233Z) is 70 mol% to 99.9999 mol% and 1,1 , 1,4,4,4-hexafluoro-2-butene in a Z form (hereinafter sometimes referred to as HFO-1336mzz (Z) or 1336Z) of 0.0001 mol% to 30 mol%
  • HFO-1336mzz (Z) or 1336Z Z form of 0.0001 mol% to 30 mol%
  • the present invention includes the following inventions.
  • invention 2 The azeotropic (like) composition according to invention 1, comprising 70 mol% to 99.9999 mol% 1233Z and 0.0001 mol% to 30 mol% 1336Z.
  • invention 3 The azeotropic (like) composition according to Invention 1 or Invention 2, comprising 80 to 99.9999 mol% of 1233Z and 0.0001 to 20 mol% of 1336Z.
  • a liquid composition comprising the azeotropic (like) composition according to any one of Inventions 1 to 3 and at least one additional component.
  • a liquid composition comprising the azeotropic (like) composition according to any one of the inventions 1 to 3 and at least one additional component of 10 ppm to 30% by mass based on the azeotropic (like) composition.
  • a cleaning solvent comprising the azeotropic (like) composition or liquid composition according to any one of Inventions 1 to 5.
  • invention 7 A method for cleaning an object to be cleaned, comprising the step of bringing the azeotropic (like) composition or liquid composition according to any one of Inventions 1 to 5 into contact with the object to be cleaned.
  • a novel azeotropic (like) composition exhibits an effect that the composition hardly changes even when used under an open condition.
  • the azeotropic (like) composition has a low environmental impact and is a non-hazardous material under the Fire Service Law.
  • the azeotropic (like) composition is useful as a solvent (cleaning solvent) for cleaning contaminants such as foreign matters and fats and oils.
  • the fluorine-containing olefin is highly compatible with various solvents, it is relatively easy to prepare a uniform composition.
  • the problem that “the liquid composition tends to fluctuate” is inherent. That is, even if a plurality of types of liquids are mixed to ensure compatibility, the problem that the liquid composition tends to fluctuate due to the difference in volatility of each component is unavoidable.
  • a binary liquid composition is put into an ultrasonic cleaner and used as a cleaning agent, generally low boiling point components with high volatility (components with high vapor pressure) are preferentially volatilized, and the inside of the cleaning tank High-boiling components with low volatility are concentrated.
  • the concentration of the low-boiling component in the cleaning liquid may decrease with time, leading to poor cleaning.
  • the cleaning liquid may become a combustible composition when the noncombustible component volatilizes preferentially.
  • thermodynamic cycle There is a similar problem when used as a working fluid in a thermodynamic cycle. That is, even when used as a working fluid in a thermodynamic cycle, the liquid composition may fluctuate over a long period of time. If the liquid composition fluctuates, the heat capacity, viscosity, or affinity with the lubricant of the liquid may change, and the operating performance of the thermodynamic cycle may deteriorate.
  • liquid composition management can be a heavy work load.
  • azeotropic refers to azeotropic in a thermodynamically strict sense.
  • ethanol 96% by mass
  • water 4% by mass
  • vapor that exists in vapor-liquid equilibrium with this is also “ethanol ( 96% by mass): water (4% by mass) ”, which completely matches the liquid composition.
  • azeotropic At a specific temperature and pressure, the composition of the azeotrope is only one point.
  • “Azeotropic” is also called “pseudo-azeotropic” and is not thermodynamically strict azeotrope, but for a range of liquid compositions, the liquid composition and the composition of the gas in equilibrium , Refers to such a phenomenon that may be substantially equal. Even if the compositions of the gas phase part and the liquid phase part do not completely match, those skilled in the art can handle the composition in the same manner as the azeotropic composition as long as the composition of the gas phase part and the liquid phase substance substantially match. At this time, the smaller the vapor-liquid equilibrium composition difference between the gas phase portion and the liquid phase portion, the better. As described above, a phenomenon in which the vapor-liquid equilibrium portion substantially matches the vapor-liquid equilibrium composition is called azeotropic or pseudo-azeotropic, and the composition is called azeotropic-like or pseudo-azeotropic composition. .
  • azeotropic and pseudo-azeotropic should be distinguished, but in practical use such as cleaning, azeotropic and azeotropic (or pseudo-azeotropic) are distinguished.
  • azeotropic phenomenon and the azeotrope-like phenomenon are collectively referred to as “azeotrope (like)”.
  • the composition at that time is referred to as an “azeotropic (like) composition”.
  • the volatilization behavior of this composition was investigated in detail, and as a result, the first component 1233Z was 70 mol% to 99.9999 mol% and the second component 1336Z was 0.0001 mol%.
  • the composition in which the first component 1233Z is 80 mol% to 99.9999 mol% and the second component 1336Z is 0.0001 mol% to 20 mol% is preferably volatilized. Since it volatilizes at a composition ratio that approximates the liquid phase composition, it turns out that, for example, in the cleaning process, even if it partially volatilizes from inside the cleaning machine, the composition of the cleaning liquid does not change in practice. did. Among them, a composition in which 1233Z as the first component is 90 mol% to 99.9999 mol% and 1336Z as the second component is 0.0001 mol% to 10 mol% is particularly preferable because the composition variation is much smaller.
  • the azeotropic (like) composition of the present invention is one of preferred embodiments in which a high-purity composition substantially free of impurities is mixed.
  • a liquid composition with such a high purity may not be required.
  • a small amount of raw materials and by-products for synthesizing the first component 1233Z and the second component 1336Z usually each component has the azeotropic (like) composition.
  • the remaining one usually less than 1% by weight
  • additional components may be added to improve the performance of the azeotropic (like) composition, resulting in a “liquid composition comprising the azeotropic (like) composition of the present invention and at least one additional component”.
  • additional component include a detergency enhancer (surfactant), a stabilizer (acid acceptor, antioxidant), and the like.
  • the surfactant include sorbitan aliphatic esters such as sorbitan monooleate and sorbitan trioleate; polyoxyethylene sorbite fatty acid esters such as sorbite tetraoleate of polyoxyethylene; polyoxyethylene monolaur Polyethylene glycol fatty acid esters such as rate; polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether; polyoxyethylene alkyl phenyl ethers such as polyoxyethylene nonylphenyl ether; polyoxyethylene such as polyoxyethylene oleic acid amide
  • Nonionic surfactants such as alkylamine fatty acid amides may be mentioned. These surfactants may be used alone or in combination of two or more.
  • cationic surfactants and anionic surfactants are added to the detergent containing the azeotrope-like composition of the present invention in order to synergistically improve the detergency and interfacial action. May be.
  • the amount of the surfactant used varies depending on the type of the surfactant, but it is sufficient that it does not interfere with the azeotrope-like properties of the azeotrope-like composition. It is about mass% or less, and it is preferable to set it as about 0.3 mass% or more and 5 mass% or less.
  • the type of the stabilizer is not particularly limited, and examples thereof include nitro compounds, epoxy compounds, phenols, imidazoles, amines, hydrocarbons and the like.
  • the liquid composition to which such a stabilizer is added is particularly useful when used under severe conditions.
  • nitro compound a known compound can be suitably used, and examples thereof include aliphatic and / or aromatic nitro compounds.
  • examples of the aliphatic nitro compound include nitromethane, nitroethane, 1-nitropropane, 2-nitropropane and the like.
  • aromatic nitro compounds for example, nitrobenzene, o-, m- or p-dinitrobenzene, trinitrobenzene, o-, m- or p-nitrotoluene, o-, m- or p-ethylnitrobenzene, 2,3-, 2,4-, 2,5-, 2,6-, 3,4- or 3,5-dimethylnitrobenzene, o-, m- or p-nitroacetophenone, o-, m- or p-nitrophenol, o -, M- or p-nitroanisole and the like can be mentioned.
  • Examples of the epoxy compound include ethylene oxide, 1,2-butylene oxide, propylene oxide, styrene oxide, cyclohexene oxide, glycidol, epichlorohydrin, glycidyl methacrylate, phenyl glycidyl ether, allyl glycidyl ether, methyl glycidyl ether, butyl glycidyl ether, 2 -Monoepoxy compounds such as ethylhexyl glycidyl ether, polyepoxy compounds such as diepoxybutane, vinylcyclohexene dioxide, neopentyl glycol diglycidyl ether, ethylene glycol diglycidyl ether, glycerin polyglycidyl ether, trimethylolpropane tolglycidyl ether Etc.
  • the phenols may contain various substituents such as an alkyl group, an alkenyl group, an alkoxy group, a carboxyl group, a carbonyl group, and a halogen in addition to the phenolic hydroxyl group.
  • substituents such as an alkyl group, an alkenyl group, an alkoxy group, a carboxyl group, a carbonyl group, and a halogen in addition to the phenolic hydroxyl group.
  • Monovalent phenol such as eugenol, isoeugenol, butylhydroxyanisole, phenol, xylenol or divalent such as t-butylcatechol, 2,5-di-
  • imidazoles having a linear or branched alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, or an aryl group as the N-position substituent are preferable.
  • imidazoles include 1-methylimidazole, 1-n-butylimidazole, 1-phenylimidazole, 1-benzylimidazole, 1- ( ⁇ -oxyethyl) imidazole, 1-methyl-2-propylimidazole, 1-methylimidazole, Methyl-2-isobutylimidazole, 1-n-butyl-2-methylimidazole, 1,2-dimethylimidazole, 1,4-dimethylimidazole, 1,5-dimethylimidazole, 1,2,5-trimethylimidazole, 1, Examples include 4,5-trimethylimidazole and 1-ethyl-2-methylimidazole. These compounds may be used alone, or two or more compounds may be used in combination.
  • amines examples include pentylamine, hexylamine, diisopropylamine, diisobutylamine, di-n-propylamine, diallylamine, triethylamine, N-methylaniline, pyridine, morpholine, N-methylmorpholine, triallylamine, allylamine, ⁇ -methyl.
  • hydrocarbons examples include ⁇ -methylstyrene, p-isopropenyltoluene, isoprenes, propadiene, terpenes and the like. These may be used alone, or two or more compounds may be used in combination.
  • the azeotropic (like) composition of the present invention is a precision mechanical component, an electronic material (printed circuit board, liquid crystal display, magnetic recording component, semiconductor material, etc.) It is suitable for removing foreign substances, oils, greases, greases, waxes, fluxes, inks and the like from resin processed parts, optical lenses, clothing and the like.
  • the azeotropic (like) composition of the present invention is nonflammable and has appropriate fluidity and solubility, foreign substances (such as particles) can be washed away or dissolved to be removed.
  • the cleaning method is not particularly limited, but dirt can be obtained by immersing precision mechanical parts, electronic materials, etc. in the azeotropic (like) composition of the present invention (or a liquid composition containing the azeotropic (like) composition).
  • Examples of the method include washing away, wiping with a waste cloth, and spray washing. These may be used in combination. It is one of the particularly preferred embodiments that the azeotropic (like) composition is placed in an ultrasonic cleaner, the article to be cleaned is immersed in the liquid, and ultrasonic cleaning is performed.
  • the azeotrope (like) composition of the present invention exhibits a stable detergency even if it is used in an open system, so that even if the composition is not frequently managed, it is practically used. This is a great advantage.
  • the cleaning liquid adheres to the object to be cleaned (work) and is taken out of the system. For example, in a 500-liter cleaning facility, if 20 kg of liquid decreases every week due to taking out due to adhesion to parts (workpieces) to be cleaned, charge the same amount of new liquid every week. The liquid level is kept constant.
  • the cleaning liquid used for cleaning is recovered and then subjected to a distillation operation, oils and fats and foreign matters (particles) can be separated and removed, and the azeotropic (like) composition of the present invention can be recovered. Since a general distillation regenerator for a detergent is a single distillation system, the azeotrope-like composition of the present invention can be regenerated with a commercially available distillation regenerator with substantially no change in composition.
  • the two liquid components 1233Z and 1336Z When performing the distillation operation, the two liquid components 1233Z and 1336Z maintain the properties as an azeotropic (like) composition, so that the recovered liquid is then washed again without undergoing extensive composition adjustment. Can be used as In addition, when the above “additional components” are used, these “additional components” may be removed by distillation, and in this case, it is desirable to supplement them separately.
  • Example 1 A 50 mL three-necked flask equipped with a septum, a stirrer, and a Dimroth capable of flowing a ⁇ 10 ° C. refrigerant was charged with 25 mL of 1233Z and 1336Z so as to have the molar concentrations shown in Table 1.
  • a synthetic zeolite tube was attached to the top of the Dimroth. The flask was immersed in an oil bath and heated to reflux with stirring. After 1 hour or more had passed after the refluxing started, the composition was stabilized, and then the gas phase portion was sampled from the septum with a gas tight syringe and analyzed by gas chromatography.
  • the liquid phase portion was similarly sampled using a polypropylene syringe equipped with an injection needle, and about 1 mL was sampled and transferred to a 2 mL vial previously cooled with ice water, followed by gas chromatography analysis.
  • Table 1 it was set as the mol% notation using the calibration curve prepared beforehand.
  • the horizontal axis represents the liquid phase part composition (mol%) of 1233Z and the vertical axis represents the gas phase part composition (mol%) of 1233Z, and the results of Table 1 are plotted.
  • Example 2 The flash points of the mixed liquids of 1233Z and 1336Z were measured in accordance with Japanese Industrial Standard JIS K2265-1 “How to Obtain Flash Point—Part 1: Tag Sealing Method”.
  • JIS K2265-1 How to Obtain Flash Point—Part 1: Tag Sealing Method”.
  • an automatic flash point measuring device atg-8l (Tanaka Scientific Instruments Manufacturing Co., Ltd.) was used. Table 2 shows the measurement results for each composition. In the range of azeotropic or azeotrope-like compositions of 1233Z and 1336Z, no flash point was observed under atmospheric pressure conditions.
  • ⁇ Example 3> ⁇ Cleaning test> A commercially available 25 mL graduated cylinder was cut with an 11 mL graduation line, and conditions were set for the liquid to easily volatilize. After measuring the mass of a clean glass rod having a diameter of about 7.2 mm and a length of about 40 mm, it was immersed in the oil shown in Table 3 for 2 minutes and then drained for 10 minutes (excess oil was removed). Then, after measuring the mass (glass rod + initially attached oil), it was put in the graduated cylinder.
  • the composition described in Table 3 below is a small ultrasonic washer (SW5800 manufactured by Citizen) charged with 1233Z 89.5742 mol% 1336Z 10.4258 mol% azeotrope-like composition to a liquid level of 10 mL and filled with water at 20 ° C. ) In the center.
  • the azeotrope-like composition volatilized with time, and when it reached the 8 mL scale line, the liquid in the graduated cylinder was analyzed with a gas chromatograph.
  • the liquid composition before and after washing was substantially the same.
  • the azeotrope-like composition used in Examples 3-1 to 3-5 must have an azeotrope-like composition that does not substantially change the composition of the residual liquid even if it partially volatilizes. Indicated.
  • the glass rod is dried, and the mass (total mass of the glass rod and the residual oil) is measured to obtain the oil removal rate (the mass of the residual oil ⁇ the mass of the initial adhered oil ⁇ 100 [%]) and enlarged.
  • the surface of the glass was observed with a mirror.
  • the oil removal rate was 100%, and in the magnifying glass observation results, no oil was left, so it was judged good.
  • Table 3 The results of each example are shown in Table 3 below.

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  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
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Abstract

L'invention concerne une composition liquide comprenant de 70 à 99,9999 % en moles de (Z)-1-chloro-3,3,3-trifluoropropène (1233Z) et de 0,0001 à 30 % en moles de (Z)-1,1,1,4,4,4-hexafluoro-2-butène (1336Z). Cette composition liquide présente un faible impact sur l'environnement terrestre et présente des propriétés de type azéotrope. Ainsi, une variation de composition ne se produit pas pendant l'utilisation, même lorsqu'elle est utilisée dans un système ouvert ou lorsqu'elle est utilisée pendant de longues périodes de temps. La composition n'est pas susceptible à une variation de composition pendant une récupération par distillation. Par conséquent, ce mélange liquide peut être utilisé de manière appropriée en tant qu'agent de nettoyage (solvant).
PCT/JP2016/050904 2015-02-10 2016-01-14 Composition de type azéotrope comprenant une oléfine contenant du fluor comme constituant WO2016129319A1 (fr)

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WO2016140938A1 (fr) * 2015-03-02 2016-09-09 The Chemours Company Fc, Llc Compositions azéotropes et pseudo-azéotropes de z-1-chloro-3,3,3-trifluoropropène
JP7215978B2 (ja) * 2019-08-21 2023-01-31 荒川化学工業株式会社 洗浄剤組成物及び洗浄方法

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JP2012518705A (ja) * 2009-02-24 2012-08-16 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ２−クロロ−３，３，３−トリフルオロプロペンと少なくとも１つのハイドロフルオロオレフィンとの混合物を含有する発泡体形成組成物およびポリイソシアネートベースの発泡体の製造におけるそれらの使用
JP2014500904A (ja) * 2010-11-25 2014-01-16 アルケマ フランス クロロトリフルオロプロペンとヘキサフルオロブテンとの組成物
JP2014005418A (ja) * 2012-06-27 2014-01-16 Central Glass Co Ltd フッ素化不飽和炭化水素を含む熱伝達媒体
JP2014523928A (ja) * 2011-05-19 2014-09-18 アーケマ・インコーポレイテッド クロロ−トリフルオロプロペンの不燃性組成物

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US9145480B2 (en) * 2010-10-28 2015-09-29 Honeywell International Inc. Mixtures containing 1,1,1,3,3,3-hexafluorobutene and 1-chloro-3,3,3-trifluoropropene

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JP2012518705A (ja) * 2009-02-24 2012-08-16 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ２−クロロ−３，３，３−トリフルオロプロペンと少なくとも１つのハイドロフルオロオレフィンとの混合物を含有する発泡体形成組成物およびポリイソシアネートベースの発泡体の製造におけるそれらの使用
JP2014500904A (ja) * 2010-11-25 2014-01-16 アルケマ フランス クロロトリフルオロプロペンとヘキサフルオロブテンとの組成物
JP2014523928A (ja) * 2011-05-19 2014-09-18 アーケマ・インコーポレイテッド クロロ−トリフルオロプロペンの不燃性組成物
JP2014005418A (ja) * 2012-06-27 2014-01-16 Central Glass Co Ltd フッ素化不飽和炭化水素を含む熱伝達媒体

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