EP0994929B1 - Compositions azeotropes, et du type azeotrope, de 1-bromopropane et d'hydrocarbures a haute teneur en fluor - Google Patents

Compositions azeotropes, et du type azeotrope, de 1-bromopropane et d'hydrocarbures a haute teneur en fluor Download PDF

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EP0994929B1
EP0994929B1 EP98933297A EP98933297A EP0994929B1 EP 0994929 B1 EP0994929 B1 EP 0994929B1 EP 98933297 A EP98933297 A EP 98933297A EP 98933297 A EP98933297 A EP 98933297A EP 0994929 B1 EP0994929 B1 EP 0994929B1
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composition
azeotrope
bromopropane
weight
solvent
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EP0994929A4 (fr
EP0994929A1 (fr
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Richard J. Degroot
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Great Lakes Chemical Corp
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Great Lakes Chemical Corp
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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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/261—Alcohols; Phenols
    • 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
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/504—Azeotropic mixtures containing halogenated solvents all solvents being halogenated hydrocarbons
    • C11D7/505—Mixtures of (hydro)fluorocarbons
    • 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
    • C11D7/5036—Azeotropic mixtures containing halogenated solvents
    • C11D7/5068—Mixtures of halogenated and non-halogenated solvents
    • C11D7/5077—Mixtures of only oxygen-containing solvents
    • C11D7/5081—Mixtures of only oxygen-containing solvents the oxygen-containing solvents being alcohols only
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
    • C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
    • C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
    • C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
    • C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
    • C23G5/02825—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine containing hydrogen
    • 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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/263—Ethers
    • 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
    • C11D7/22—Organic compounds
    • C11D7/26—Organic compounds containing oxygen
    • C11D7/264—Aldehydes; Ketones; Acetals or ketals
    • 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
    • C11D7/22—Organic compounds
    • C11D7/28—Organic compounds containing halogen

Definitions

  • This invention relates to a cleaning solvent comprising a highly-fluorinated hydrocarbon and 1-bromopropane and to a method of cleaning articles. More particularly, this invention is directed to a solvent composition that includes 1,1,1,2,3,4,4,5,5,5-decafluoropentane, 1-bromopropane, and optionally stabilizers and co-solvents, and to a method of cleaning articles having cloth, plastic, metallic and ceramic surfaces.
  • HFC's are chemically stable, nontoxic, nonflammable and less hazardous to the environment then either CFC's or HCFC's.
  • HFC's are not considered to be as effective cleaning and degreasing solvents as the CFC's and HCFC's.
  • Highly fluorinated hydrocarbons (HFC's) have a low solvating ability when compared with CFC's and HCFC's, and HFC's are not as efficacious as CFC's and HCFC's for dissolving greases and oils or disbursing other undesirable materials such as flux and flux residues on printed circuit boards. It has been determined that HFC's can be combined with other organic solvents to provide a cleaning solution having higher solvating ability.
  • the added organic solvent must be carefully selected so the resulting cleaning and degreasing solvent maintains its desirable physical and chemical properties such as low toxicity. low boiling, environmentally friendly and nonflammable. Furthermore while a particular solvent mixture initially may provide the desired physical and chemical characteristics in bulk, i.e. non-toxic, low boiling, nonflammable and high solvating ability, in practice, the mixture may be inadequate.
  • Solvents are often recovered by distilling used or contaminated solutions to provide essentially pure solvents that can be reused. Partitioning during recovery requires that one or more of the original components be added to the recovered solvent to maintain the original solvent composition.
  • compositions for use as industrial vapour degreasing fluids comprise 1-bromopropane in combination with a binary stabiliser mixture comprising nitromethane and either 1,2-butyleneoxide or timethoxymethane.
  • the stabiliser ensures that the 1-bromopropane present in the composition is not decomposed in to hydrogen bromide which can corrode the material (e.g. zinc, iron or copper) being cleaned during the repeated high temperature cleaning cycles employed during vapour phase degreasing of the material.
  • JP-A-3176433 describes a series of specific compositions for use as solvents which exhibit azeotropic or azeotropic-like behaviour, making them particularly suitable for use in processes where it is desirable to recycle the solvent.
  • the compositions comprise 1- or 2-bromopropane in combination with various isomers of trichlorodifluoroethane, which are used in preference to 1,1,1-trichloroethane and 1,1,2,2-tetrachloro-1,2-difluorothane due to the ozone-layer disrupting properties of the latter compounds.
  • the present invention provide a solvent compositions that include a highly fluorinated hydrochlorofluorocarbon (HFC) and 1-bromopropane useful as cleaning and degreasing solvents.
  • the solvent composition optionally includes stabilizers and co-solvents.
  • the stabilizers and co-solvents include alcohols, ketones, ethers, acetals, nitroalkanes. epoxides, amines, and saturated and unsaturated hydrocarbons.
  • the azeotropic mixtures are a preferred composition, non-azeotropic mixtures are considered to lie within the scope of the present invention.
  • the most preferred composition for the present invention is an azeotropic composition comprising 1,1,1,2,3,4,4,5,5,5-decafluoropentane and 1-bromopropane.
  • the solvent composition optionally includes stabilizers and co-solvents.
  • the solvent compositions comprising HFC's and 1-bromopropane provide non-azeotrope and azeotrope or azeotrope-like compositions that are well suited for solvent-cleaning applications.
  • the present invention also provides a method for cleaning an article having a cloth, ceramic, plastic or metallic surface using the solvent compositions comprising 1-bromopropane and a highly fluorinated hydrocarbon.
  • the solvent is applied to the article's surface by any of the known or conventional methods to clean and degrease grease, oils and particulate matter adhering to the article's surface. Removal of the contaminated solvent provides a cleaned article that is suitable for subsequent processing or forwarding to consumers.
  • the figure 1 is a plot of 1,1,1,2,3,4,4,5,5,5-decafluoropentane concentrations by weight of the composition in the liquid and vapor phases obtained during distillation of the solvent composition.
  • the present invention is directed to a solvent composition comprising 1-bromopropane and a highly fluorinated hydrocarbon for use as a cleaning and degreasing solvent.
  • the highly fluorinated hydrocarbon is a highly fluorinated pentane.
  • the solvent composition includes stabilizers and co-solvents such as alcohols, ketones, ethers, acetals, nitroalkanes, epoxides, amines, and saturated and unsaturated hydrocarbons.
  • the solvent composition comprises an azeotrope or azeotropic-like composition that consists essentially of 1-bromopropane and a highly fluorinated pentane.
  • This azeotrope solvent composition provides a constant boiling solvent that does not partition upon evaporation or distillation. While the azeotrope and azeotrope-like composition are preferred, the non-azeotrope composition comprising 1-bromoproane and a highly fluorinated pentane are still considered to be within the scope of the invention.
  • Use of the solvent prepared according to this invention cleans a wide variety of articles having cloth, ceramic, metallic, and plastic surfaces.
  • an azeotrope composition is defined as a constant boiling liquid admixture of two or more substances that exhibits physical characteristics of a single compound, in that the vapor, produced by partial evaporation or distillation of the liquid, has substantially the same composition as the liquid, i.e., the admixture distills without substantial change in the composition.
  • Constant boiling compositions which are characterized as azeotropes, exhibit either a maximum or minimum boiling point as compared with that of the non-azeotropic mixtures of the same substances.
  • the present invention contemplates the admixture of the highly fluorinated pentane, 1-bromopropane, and optionally one or more stabilizers and co-solvents in an azeotrope mixture.
  • azeotrope-like compositions it is meant that a composition of compounds has a concentration that may vary. however minor, from the concentrations found in the azeotropic compositions.
  • concentrations of the highly fluorinated pentane, 1-bromopropane, and added stabilizers and co-solvents included in an azeotrope-like composition may vary somewhat from the concentrations found in the azeotrope formed between them and remain a composition within the scope of this invention.
  • the boiling points of the azeotrope-like compositions will be substantially the same as those of their corresponding azeotropes.
  • the azeotrope-like compositions boil. at ambient pressure, at temperatures that are within about 2°C of the temperatures at which their corresponding azeotropes boil at the same pressure.
  • compositions of highly fluorinated pentane, 1-bromopropane and additional stabilizers and co-solvents that, when fractionally distilled, provide a distillate that is an azeotrope or an azeotrope-like composition when the concentrations of the highly fluorinated pentane, 1-bromopropane and added stabilizers and co-solvents differ from the concentrations of the azeotrope or azeotrope-like compositions are within the scope of this invention.
  • the concentrations of the highly fluorinated pentane, 1-bromopropane, and added stabilizers and co-solvents of such compositions differ from the concentration of the azeotrope or azeotrope-like composition by no more than about 10%, more preferably, no more than about 5% by weight.
  • solvating ability is meant the characteristic of a composition in the liquid state to dissolve solid or semi-solid matter and become miscible with liquids including gums, greases and gels.
  • solvation entails dispersing molecules of the matter with solvent molecules. The dissolution and miscibility does not have to be complete, i.e. infinite solubility or miscibility with the matter.
  • increasing the amount of the solvent composition added to the substrate or by repeated application of essentially non-contaminated solvent successively solubilizes more of the matter with each increase in solvent amount or each successive application of essentially non-contaminated solvent.
  • One method of evaluating a solvent's solvating ability is to measure its Kauri Butanol value as described in ASTM D1133-94 Standard Test Method for Kauri Butanol Value of Hydrocarbon Solvents.
  • the solvent composition of the present invention comprises a highly fluorinated pentane.
  • the highly fluorinated pentane consists essentially of 1,1,1,2,3,4,4,5,5,5-decafluoropentane. This decafluoropentane is commercially available under the trade name Vertrel XF from Dupont.
  • the solvent composition of the present invention is a azeotrope composition consisting essentially of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and 1-bromopropane having about 84.7% by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane and about 15.3% by weight 1-bromopropane and a boiling point of about 49.2°C at atmospheric pressure.
  • the solvent composition also includes 1-bromopropane, which is commercially available from Great Lakes Chemical Corporation. This halogenated solvent is low boiling, inexpensive and considered less harmful to the atmospheric ozone layer than chlorofluorocarbons. Importantly, 1-bromopropane is non-toxic, unlike many other halogenated alkanes; for example, 2-bromopropane is considered to be extremely toxic to both humans and animals. Furthermore, 1-bromopropane has an extremely high solvating ability as is exemplified by its Kauri Butanol Value of 125.
  • 1-bromopropane provides an excellent cleaning solvent for metal components, its high solvating ability limits its application for plastics and elastomers; 1-bromopropane tends to etch or partially dissolve plastic surfaces. Admixtures of 1-bromopropane with less aggressive solvents such as hydrochlorofluorocarbons reduces this detrimental effect on plastics and elastomers while at the same time it increases the solvating ability of the hydrochlorofluorocarbons.
  • the final solvent blend is highly effective for cleaning a wide variety of articles having metal, ceramic, cloth and plastic surfaces.
  • the solvent composition comprises decafluoropentane and 1-bromopropane in concentrations other than the azeotropic concentrations, but when these solvent compositions are fractionally distilled, they provide azeotrope compositions.
  • concentrations of the decafluoropentane and 1-bromopropane differ from the concentrations of the azeotrope or azeotrope-like composition by no more than about 10%, more preferably no more than about 5% by weight.
  • Non-azeotrope solvent compositions that do not provide azeotrope compositions upon distillation are also included in present invention.
  • Non-azeotrope solvent compositions are useful for certain applications where partitioning of the cleaning solvent is not a major consideration.
  • the non-azeotropic solvent composition comprises 1-bromopropane and about 1% to about 99% of a highly fluorinated pentane, preferably about 10% to about 90% by weight, more preferably about 30% to about 70% by weight of a highly fluorinated pentane.
  • Admixture of 1-bromopropane and a highly fluorinated pentane provides a solvent composition with a high solvating ability.
  • a cleaning solution having a solvating ability that is lower than 1-bromopropane yet higher than the highly fluorinated pentane can be prepared.
  • the solvent of the present invention comprises about 1% to about 99% by weight 1-bromopropane, preferably about 10% to about 90% by weight, more preferably about 30% to about 70% by weight 1-bromopropane.
  • the solvent compositions of the present invention provide cleaning solvents that have a Kauri Butanol Value of about 6 to about 124, preferably about 25 to about 105, and more preferably about 35 to about 95.
  • the solvent composition includes stabilizers and co-solvents. These stabilizers and co-solvents are included to modify the physical and chemical characteristics of the solvent composition.
  • the stabilizers are added to inhibit metal induced decomposition of halogenated hydrocarbons. Often reactive metals such as aluminum, magnesium, copper, zinc, iron, titanium, tin and alloys of these metals induce decomposition of halogenated hydrocarbons such as 1-bromopropane. Typically, these metals induce hydrolysis and/or dehydrohalogenation of the alkyl halides to provide metal halides, halide salts and acids as some of the decomposition species. Generation of these decomposition species is harmful to metal components.
  • Stabilizers that are included as optional components of the solvent composition include alcohols, ketones, ethers, acetals, nitroalkanes, epoxides, amines, and mixtures of these stabilizers.
  • alcohols examples include, but are not limited to: ethyl alcohol, propyl alcohol, isopropyl alcohol, t-butyl alcohol, t-amyl alcohol, sec-butyl alcohol, phenols, e.g. phenol, p-cresol, m-cresol, o-cresol, amino alcohols, e.g. monoethanol amine, diethanol amine, triethanol amine, acetylene alcohols, e.g. methylbutynol, methylpentynol, benzotriazol, and mixtures of alcohols.
  • Typical ketones useful in the present invention include: acetone, methyl ethyl ketone (MEK), 2-propanone (diethyl ketone). 2-pentanone, 3-pentanone, 2-hexanone, 3-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2,6-dimethyl -4-heptanone, 2-methyl-3-heptanone, 2-methyl-2-butanone, 2-methyl-3-pentanone, 2-nonanone, and mixtures of ketones.
  • MEK methyl ethyl ketone
  • 2-propanone diethyl ketone
  • acetals suitable for the present invention include dimethyl and diethyl acetals of the ketones listed above.
  • Typical nitroalkanes useful in the present invention include: nitromethane, nitroethane, 1-nitropropane, 2-nitropropane, nitrobutane, and mixtures of nitroalkanes.
  • epoxides useful with the present invention include: epibromohydrin, propylene oxide, 1,2- butylene oxide, 2,3-butylene oxide, cyclohexene oxide, glycidyl methyl ether, glycidyl methacrylate, pentene oxide, cyclopentene oxide, and cyclohexene oxide.
  • the epoxides are added to the stabilized solvent either singly or as a mixture of two or more.
  • Non-nucleophilic amines are preferred, and therefore secondary and tertiary amines are desired.
  • amines useful for the present invention include: hexylamine, octylamine, 2-ethylhexylamine, dodecylamine, ethylbutylamine, hexylmethylamine, butyloctylamine, dibutylamine, octadecylmethylamine, triethylamine, tributylamine, diethyloctylamine, tetradecyldimethylamine, dibutylamine; diisobutylamine, diisopropylamine, pentylamine, N-methylmorpholine, isopropylamine, cyclohexylamine.
  • butylamine isobutylamine, dipropylamine, 2,2,6,6-tetramethylpiperidine, N, N-dimethyl-p-phenylamine, N,N-diethyl-p-phenylamine, diethylamine, aniline, ethylenediamine, propylenediamine, triethylamine, tetraethylenepentamine, benzylamine, dibenzylamine, diphenylamine, and diethylhydroxyamine. These amines are useful either singly or as a combination of two or more.
  • co-solvents examples include: alkanes, alkenes, alkynes, alcohols, ketones, esters, terpenes and various aliphatic mixtures including mineral spirits, VM&P Naptha and Stoddard solvents. Many of the stabilizers listed above are also considered to be co-solvents.
  • the co-solvents are added to modify the solvating ability of the solvent composition. Thus, for example, alcohols and ketones can be added to attenuate the solvating ability of the 1-bromopropane.
  • Cosolvents also provide a higher degree of polarity and hydrogen bonding characteristics to the solvent, which enables the solvent to effectively remove ionic or polar contaminates. Furthermore, these co-solvents are often less expensive than the highly fluorinated pentanes, and they reduce the costs associated with preparing and using the solvent blend.
  • the solvent composition is prepared by the admixture of the 1-bromopropane and a sufficient amount of the highly fluorinated pentane to provide the desired cleaning solvent having a specified concentration or a desired Kauri Butanol Value.
  • the order of addition of the components is not critical for this invention. When desired the stabilizers and co-solvents are added. In addition, minor amounts of surfactants can be included.
  • Typical surfactants useful for the invention include ionic and non-ionic surface active agents, for example, sulfonate salts, phosphate salts, carboxylate salts, fatty acids, alkyl phenols, glycols, esters and amides.
  • Surface active agents also include ionic and non-ionic water displacement compounds such as tetraalkyl ammonium sulfonate, phosphate, and carboxylate and bromide salts, aliphatic amino alkanols, fluorinated amino alkanols, and chlorofluorinated amino alkanols. Again the order of addition is not critical for the present invention.
  • ionic and non-ionic water displacement compounds such as tetraalkyl ammonium sulfonate, phosphate, and carboxylate and bromide salts, aliphatic amino alkanols, fluorinated amino alkanols, and chlorofluorinated amino alkanols. Again the order of addition is not critical for the present invention.
  • the solvent composition of the present invention is suitable for washing articles having cloth, metal, ceramic, plastic and elastomeric surfaces.
  • the solvent composition may be applied by any method known or commonly used to clean or degrease articles.
  • the surface of the article may be wiped with an absorbent medium containing the solvent composition such as a cloth saturated with the solvent.
  • the article may be submerged or partially submerged in a dip tank.
  • the solvent in a dip tank can be either hot or cold, and the article can be submerged for extended periods of time without inducing decomposition of the solvent.
  • the article, dip tank, and related components are not harmed by the process.
  • the solvent can be sprayed onto the article or the article can be cleaned in a vapor degreasing chamber with either liquid or vaporized solvent composition.
  • the solvent When the solvent is applied as a vapor, the solvent is typically heated in a solvent reservoir to vaporize the solvents. The vaporized solvent then condenses on the surface of the article. The condensed solvent solvates or entrain grease, oil, dirt, and other undesirable particles that are on the article's surface. The contaminated solvent drains into the solvent reservoir carrying the dissolved and entrained material to the reservoir. Since only the solvent is vaporized, the grease, oil, and dirt remain in the reservoir, and the article is continually flushed with non-contaminated solvents.
  • a vapor liquid diagram for 1-bromopropane and decafluoropentane was developed by mixing various concentrations of these solvents.
  • the solvent compositions were distilled in a 100 ml Othmer Still. The solvent was heated to reflux and allowed to equilibrate. Samples of the vapor and liquid portions were taken and analyzed using a gas chromatograph to determine the concentrations of the components. The results are listed in Table 1 and graphically illustrated in Figure 1. Analysis of the results indicated that an azeotrope composition exists consisting of 1-bromopropane and 1,1,1,2,3,4,4,5,5,5-decaftuoropentane.
  • a second solvent composition consisting of about 81.2 % by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane and about 17.8 % by weight 1-bromopropane was prepared.
  • This second solvent mixture was distilled in a Perkin Elmer Model 151 Annular Still, (200 theoretical plate capacity). After the refluxing solvent had equilibrated, distillate fractions comprising approximately 10% by weight of the total liquid charge were collected at a 10:1 reflux to takeoff ratio. The boiling point of each fraction was measured to the nearest 0.1 °C.
  • the concentrations of 1-bromopropane and 1,1,1,2,3,4,4,5,5,5-decafluoropentane fractions were determined using a gas chromatograph.
  • Example 2 Solvent Composition Comprising 1,1,1,2,3,4,4,5,5,5-Decafluoropentane, 1-Bromopropane and Isopropyl Alcohol
  • a solvent composition comprising about 33% by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane, about 33% by weight 1-bromopentane, and about 33% by weight isopropyl alcohol was prepared.
  • 100 g of this solvent mixture was fractionally distilled in a Perkin Elmer Annular Still model 151 (200 theoretical plate capability). The solvent was heated to reflux and allowed to equilibrate. Three distillate fractions were collected at a 10:1 reflux to takeoff ratio. The concentrations of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and isopropyl alcohol were determined for each fraction using a gas chromatograph. The results are listed in Table 3.
  • Example 3 1-Bromopropane, 1,1,1,2,3,4,4,5,5,5-Decafluoropentane and Methanol Azeotrope Composition.
  • a solvent composition comprising equal weight amounts of 1-bromopropane, 1,1,1,2,3,4,4,5,5,5-decafluoropentane and methanol was prepared.
  • One hundred grams of this solvent composition was distilled in a Perkin Elmer Still model 151 (200 theoretical plate capacity). The solvent mixture was heated to reflux and allowed to equilibrate before three ten-gram fractions were collected; the concentrations of 1,1,1,2,3,4,4,5,5,5-decafluoropentane, 1-bromopropane and methanol were determined in each fraction using a gas chromatograph. Minimal separation was observed in this preliminary distillation. Based upon the results of the initial distillation, a second solvent composition was prepared. This second composition was distilled as described above.
  • Distillate fractions each approximately 10% by weight of the total solvent weight were collected at a 10:1 reflux to takeoff ratio.
  • the compositions of the distillate fractions were then analyzed, using a gas chromatograph, and the compositional data and boiling points for the distillation are listed in Table 4. Analysis of the results listed in Table 4 confirms that minimal separation occurred between the three components during the distillation and that an azeotrope exists.
  • the azeotrope consists essentially of about 80.8% by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane, about 5.7% by weight methanol and about 13.6% by weight 1-bromopropane, and has a boiling point of about 50 °C.
  • a solvent composition comprising equal amounts by weight of 1,1,1,2,3,4,4,5,5,5-decafluoropentane, 1-bromopropane, and acetone was prepared.
  • the resulting solution was fractionally distilled in a Perkin Elmer Annular Still model 151 as described in Example 2 to initially determine if the three components form an azeotrope composition.
  • a second solvent blend comprising about 32.5% by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane, 29.9% by weight 1-bromopropane, and about 37.4% by weight acetone was prepared.
  • This second solvent composition was fractionally distilled in the Perkin Elmer still.
  • distillate fractions of approximately 10% by weight based upon the total solvent were collected at a 10:1 reflux to takeoff ratio. Each distillate fraction was analyzed using a gas chromatograph to determine the concentrations of each of the components. The results are tabulated in Table 5.
  • a solvent composition comprising about 33% by weight 1,1,1,2,3,4,4,5,5,5-decafluoropentane, about 33% by weight 1-bromopropane and about 33% by weight nitromethane was prepared and distilled as described in Example 2.

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Claims (22)

  1. Composition de solvant comprenant du 1-bromopropane et environ 1% à environ 99% en poids d'un hydrocarbure fluoré constitué essentiellement de 1,1,1,2,3,4,4,5,5,5-décafluoropentane.
  2. Composition selon la revendication 1, comprenant environ 10% à environ 90% en poids de l'hydrocarbure fluoré.
  3. Composition selon la revendication 2, comprenant environ 30% à environ 70% en poids de l'hydrocarbure fluoré.
  4. Composition selon la revendication 1, constituée essentiellement d'une composition azéotrope ou semblable à une composition azéotrope de 1-bromopropane et de l'hydrocarbure fluoré.
  5. Composition selon la revendication 1, essentiellement constituée de 1-bromopropane et de l'hydrocarbure fluoré, qui lorsqu'elle est distillé de manière fractionnée, propose un distillat fractionné qui est une composition azéotrope ou semblable à une composition azéotrope dans laquelle les concentrations du 1-bromopropane et de l'hydrocarbure fluoré diffèrent des concentrations de la composition azéotrope ou semblable à une composition azéotrope de pas plus d'environ 10% en poids.
  6. Composition selon la revendication 1, comprenant environ 11% à environ 17% en poids de 1-bromopropane et environ 83% à environ 90% en poids d'hydrocarbure fluoré.
  7. Composition selon la revendication 1, ayant un indice de kauri-butanol d'environ 5 à environ 125.
  8. Composition selon la revendication 1, comprenant en outre un agent stabilisant choisi parmi le groupe constitué des alcools, des cétones, des nitroalcanes, des époxydes, des amines, des éthers, et des mélanges de ceux-ci.
  9. Composition selon la revendication 8, dans laquelle l'agent stabilisant est un alcool en C1 à C5.
  10. Composition selon la revendication 9, essentiellement constituée d'une composition azéotrope ternaire ou semblable à une composition azéotrope ternaire de 1-bromopropane, d'hydrocarbure fluoré et d'alcool.
  11. Composition selon la revendication 9, constituée essentiellement de 1-bromopropane, de l'hydrocarbure fluoré et de l'alcool qui, lorsqu'elle est distillée de manière fractionnée, propose un distillat fractionné qui est une composition azéotrope ou semblable à une composition azéotrope dans laquelle les concentrations de 1-bromopropane, d'hydrocarbure fluoré, et d'alcool diffèrent des concentrations de la composition azéotrope ou semblable à une composition azéotrope de pas plus d'environ 10% en poids.
  12. Composition selon la revendication 9, comprenant environ 12% à environ 16% en poids de 1-bromopropane, environ 78% à environ 84% en poids d'hydrocarbure fluoré, et environ 5% à environ 6% en poids de méthanol.
  13. Composition selon la revendication 9, comprenant environ 20% à environ 25% en poids de 1-bromopropane, environ 70% à environ 80% en poids d'hydrocarbure fluoré et environ 1% à environ 5% en poids de 2-propanol.
  14. Composition selon la revendication 8, dans laquelle l'agent stabilisant est une cétone.
  15. Composition selon la revendication 14 constituée essentiellement d'une composition azéotrope ternaire ou semblable à une composition azéotrope ternaire de 1-bromopropane, d'hydrocarbure fluoré et de cétone.
  16. Composition selon la revendication 14, essentiellement constituée de 1-bromopropane, de l'hydrocarbure fluoré, et de la cétone qui, lorsqu'elle est distillée de manière fractionnée, propose un distillat fractionné qui est une composition azéotrope ou semblable à une composition azéotrope dans laquelle les concentrations de 1-bromopropane, de l'hydrocarbure fluoré et de la cétone diffèrent des concentrations de la composition azéotrope ou semblable à une composition azéotrope de pas plus d'environ 10% en poids.
  17. Composition selon la revendication 14, comprenant environ 24% à environ 31% en poids de 1-bromopropane, environ 26% à environ 35% en poids d'hydrocarbure fluoré, et environ 35% à environ 46% en poids d'acétone.
  18. Composition selon la revendication 8, comprenant environ 15% à environ 25% en poids de 1-bromopropane, environ 65% à environ 75% en poids d'hydrocarbure fluoré, et environ 5% à environ 15% en poids d'oxyde de butylène.
  19. Procédé de nettoyage d'un article, ledit procédé comprenant les étapes de mise en contact de l'article avec une composition de solvant comprenant du 1-bromopropane et environ 1% à environ 99% en poids d'un hydrocarbure fluoré constitué essentiellement de 1,1,1,2,3,4,4,5,5,5-décafluoropentane.
  20. Procédé selon la revendication 19, dans lequel la composition de solvant comprend environ 10% à environ 90% en poids d'hydrocarbure fluoré.
  21. Procédé selon la revendication 20, dans lequel la composition de solvant comprend environ 30% à environ 70% en poids d'hydrocarbure fluoré.
  22. Procédé selon la revendication 19, dans lequel la composition de solvant comprend en outre un agent stabilisant choisi parmi le groupe constitué des alcools, des cétones, des nitroalcanes, des époxydes, des amines, des éthers, et des mélanges de ceux-ci.
EP98933297A 1997-07-09 1998-07-09 Compositions azeotropes, et du type azeotrope, de 1-bromopropane et d'hydrocarbures a haute teneur en fluor Expired - Lifetime EP0994929B1 (fr)

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US5205897P 1997-07-09 1997-07-09
US52058P 1997-07-09
PCT/US1998/014252 WO1999002616A1 (fr) 1997-07-09 1998-07-09 Compositions azeotropes, et du type azeotrope, de 1-bromopropane et d'hydrocarbures a haute teneur en fluor

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EP0994929A4 EP0994929A4 (fr) 2001-02-21
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JP (1) JP2001509533A (fr)
AU (1) AU8297398A (fr)
CA (1) CA2296589C (fr)
DE (1) DE69826473T2 (fr)
WO (1) WO1999002616A1 (fr)

Cited By (2)

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Publication number Priority date Publication date Assignee Title
US20110112342A1 (en) * 2007-09-25 2011-05-12 Albemarle Corporation Methods of removing impurities from alkyl bromides during distillation and distillate produced therein
US8100987B2 (en) 2004-03-16 2012-01-24 Jane D. Middleton Cleaning fluid and methods

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1999035210A1 (fr) * 1998-01-02 1999-07-15 E.I. Du Pont De Nemours And Company Compositions de decafluoropentane
EP1068289A4 (fr) * 1998-02-03 2003-04-02 Petroferm Inc Composition a base organique
US6951835B1 (en) 1999-03-22 2005-10-04 E.I. Du Pont De Nemours And Company Azeotrope-like compositions of 1,1,1,3,3-pentafluorobutane
CN103385865B (zh) * 2013-07-04 2015-08-05 浙江工业大学 10-芳甲烯基蒽酮类化合物在制备抗肿瘤药物中的应用
JP6258777B2 (ja) * 2014-05-14 2018-01-10 株式会社ブリヂストン ウレタン樹脂系溶剤形接着剤組成物、ウレタン樹脂系溶剤形接着剤、ウレタン樹脂系溶剤形接着剤の製造方法、及びウレタン樹脂系溶剤形接着剤を用いた積層体

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US4652389A (en) * 1984-12-14 1987-03-24 The Clorox Company Carpet cleaner
JPH03176433A (ja) * 1989-12-05 1991-07-31 Asahi Glass Co Ltd トリクロロジフロロエタンを主成分とする共沸および共沸様組成物
US5064559A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Binary azeotropic compositions of (CF3 CHFCHFCF2 CF3) with methanol or ethanol or isopropanol
US5064560A (en) * 1990-10-11 1991-11-12 E. I. Du Pont De Nemours And Company Ternary azeotropic compositions of 43-10mee (CF3 CHFCHFCH2 CF.sub.
US5196137A (en) * 1991-10-01 1993-03-23 E. I. Du Pont De Nemours And Company Azeotropic composition of 1,1,1,2,3,4,4,5,5,5-decafluoropentane and trans-1,2-dichloroethylene, cis-1,2-dichloroethylene or 1,1-dichlorethane
JPH05124990A (ja) * 1991-10-30 1993-05-21 Du Pont Mitsui Fluorochem Co Ltd 共沸様組成物
US5858953A (en) * 1995-04-12 1999-01-12 Tosoh Corporation Stabilized 1-bromopropane composition
WO1999035210A1 (fr) * 1998-01-02 1999-07-15 E.I. Du Pont De Nemours And Company Compositions de decafluoropentane

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8100987B2 (en) 2004-03-16 2012-01-24 Jane D. Middleton Cleaning fluid and methods
US20110112342A1 (en) * 2007-09-25 2011-05-12 Albemarle Corporation Methods of removing impurities from alkyl bromides during distillation and distillate produced therein
US8492598B2 (en) * 2007-09-25 2013-07-23 Albemarle Corporation Methods of removing impurities from alkyl bromides during distillation and distillate produced therein

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AU8297398A (en) 1999-02-08
DE69826473T2 (de) 2006-02-23
CA2296589C (fr) 2007-10-16
EP0994929A4 (fr) 2001-02-21
WO1999002616A1 (fr) 1999-01-21
JP2001509533A (ja) 2001-07-24
CA2296589A1 (fr) 1999-01-21
EP0994929A1 (fr) 2000-04-26

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