WO2004020376A1 - Alcool halogene et son procede de production - Google Patents

Alcool halogene et son procede de production Download PDF

Info

Publication number
WO2004020376A1
WO2004020376A1 PCT/JP2003/010729 JP0310729W WO2004020376A1 WO 2004020376 A1 WO2004020376 A1 WO 2004020376A1 JP 0310729 W JP0310729 W JP 0310729W WO 2004020376 A1 WO2004020376 A1 WO 2004020376A1
Authority
WO
WIPO (PCT)
Prior art keywords
propanol
dichloro
trifluoro
reaction
trifluoroacetone
Prior art date
Application number
PCT/JP2003/010729
Other languages
English (en)
Japanese (ja)
Inventor
Naoto Takada
Takeo Komata
Original Assignee
Central Glass Company, Limited
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Central Glass Company, Limited filed Critical Central Glass Company, Limited
Publication of WO2004020376A1 publication Critical patent/WO2004020376A1/fr

Links

Classifications

    • 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
    • C11D7/5004—Organic solvents
    • C11D7/5018—Halogenated solvents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/143—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones
    • C07C29/145—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of ketones with hydrogen or hydrogen-containing gases
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12C—BEER; PREPARATION OF BEER BY FERMENTATION; PREPARATION OF MALT FOR MAKING BEER; PREPARATION OF HOPS FOR MAKING BEER
    • C12C11/00—Fermentation processes for beer
    • C12C11/02—Pitching yeast
    • 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

  • the present invention relates to 1,1-dichloro-3,3,3-trifluoro-2-propanol and analogous compounds thereof, which are useful as a solvent, a solvent, an intermediate for pharmaceuticals / pesticides, and a reagent for introducing a fluorine-containing group.
  • 1,1,1,3,3,3-hexafluoro-2-propanol (CF 3 CH (OH) CF 3 ) is used as a raw material for pharmaceuticals and agrochemicals, as a reagent for introducing a fluorine-containing group, and as a fluoropolymer. It is widely used as a solvent and a reaction solvent in organic synthesis. Also, 2,2,3,3-tetrafluoropropanol (CHF 2 CF 2 CH 2 OH) is widely used as a dye solvent for optical storage media such as CD-R and DVD-R (W ⁇ 2002/034841, JP-A-2002-53507).
  • 1,1,1,3,3,3-hexafluoro-2-propanol and 2,2,3,3-tetrafluoropropanol mentioned above have their own solubility due to the effect of fluorine atoms in the molecule. Have. However, some solutes do not show sufficient solubility. For this reason, if an alcohol in which some of these fluorine atoms are substituted with chlorine atoms can be obtained, the solubility as a solvent will change appropriately, and a solubility different from that of the above-mentioned fluorine-containing alcohols will be developed. Expected.
  • 1,1,1,3,3,3_hexafluoro-2-propanol and 2,2,3,3-tetrafluoropropanol have boiling points of 59 ° C and 109, respectively.
  • the dye solvent a compound that is flame-retardant or non-flammable, contains a fluorine atom and a chlorine atom, and has a boiling point of about 120 ° C is desired.
  • An object of the present invention is to provide alcohols which are useful as an intermediate for a solvent, a solvent, a pharmaceutical or agrochemical, or as a reagent for introducing a fluorine-containing group, and contain both a fluorine atom and a chlorine atom.
  • Still another object of the present invention is to provide a method for efficiently producing the alcohols by using a readily available compound as a raw material.
  • the present inventors have made intensive studies on the synthesis of alcohols containing both a fluorine atom and a chlorine atom. As a result, they have found that the above-mentioned problems can be solved by reacting 1,1-dichloro-3,3,3-trifluoromethylacetone, which is easily available, with hydrogen gas under specific conditions.
  • 1,1-dichloro-3,3,3-trifluoromethylethylacetone is a novel compound when brought into contact with hydrogen gas in the presence of water and in the presence of a catalyst containing at least platinum and in the presence of water. It was found that 1,1-dichloro-3,3,3-trifluoromethyl-2-propanol was produced mildly.
  • the present invention is common to the inventions of JP-A-2000-226057 and JP-A-2001-316322 in that 1,1-dichloro-3,3,3-trifluoromethylacetone is subjected to reduction treatment. The site of occurrence is completely different from these.
  • the 1,1-dichloro-3,3,3-trifluoromethyl-12-propanol obtained in this way has a boiling point of 123 ° C and not only has an appropriate boiling point as a solvent for dissolving the dye, but also However, it was found that there was no flash point, and that the alcohol was particularly safe in handling. It was also found that it has high solubility in organic compounds and functions well as a detergent. This compound has three fluorine atoms, two chlorine atoms and a hydroxyl group, and is also useful as a new building block in the synthesis of fluorinating agents and pharmaceuticals.
  • the present inventors have further found that when 1,1-dichloro-3,3,3-trifluoromethyl-2-propanol is synthesized by the above-mentioned method, 1,1,1-trifluoro-2-propanol is used as a by-product.
  • 1,1,1-trifluoro-2-propanol is used as a by-product.
  • the reaction is carried out at a temperature of 50 ° C or more in the presence of excess water, 1,1,1-trifluoro- It was found that the amount of 2-propanol produced increased.
  • This 1,1,1-trifluoro-2-propanol cannot be produced by the methods described in JP-A-2000-226057 and JP-A-2001-316322, and also as a fluorine-introducing agent. It is a useful compound.
  • the present invention provides a novel compound, 1,1 dichloromouth-3,3,3-trifluoro-2-propanol.
  • the present invention is also characterized in that 1,1-dichloro-3,3,3-trifluoroacetone is brought into contact with hydrogen gas in the presence of water and a catalyst containing at least platinum.
  • a method for producing 2,3,3-trifluoro-2-propanol In this case, the amount of water may be 3 mol or more per mol of 1,1-dichloro-3,3,3-trifluoroacetone.
  • the present invention comprises contacting 1,1-dichloro-3,3,3-trifluoroacetone with hydrogen gas in the presence of water and a catalyst containing at least platinum. 2_ How to make propanol provide.
  • the amount of water may be 10 mol or more per 1 mol of 1,1-dichloro-3,3,3-trifluoroacetone.
  • the present invention also provides a method using 1,1-dichloro-3,3,3-trifluoro-2-propanol as a solvent and a cleaning agent.
  • the present invention provides a method for dissolving a dye in 1,1-dichloro-3,3,3-trifluoro-2-propanol.
  • Chiya is one city of 19 F- NMR in CD C 1 3 in a solvent (Used equipment: JEOL 400MHz FT-NMR ( ⁇ -400)).
  • the gas phase method refers to a method in which a mixture containing raw materials is vaporized to perform a reaction.
  • a mixture containing the raw material compound 1,1-dichloro-3,3,3-trifluoroacetone is vaporized, then mixed with hydrogen gas, and introduced into a reaction group at a predetermined temperature containing a catalyst.
  • the liquid phase method refers to a method in which a mixture containing raw materials is kept in a liquid phase and is brought into contact with hydrogen gas to cause a reaction.
  • a mixture (liquid) containing 1,1 dichloro-3,3,3-trifluoromethylacetone as a raw material is introduced into a reaction group, hydrogen gas is introduced in the presence of a catalyst, and the mixture is stirred at a predetermined temperature.
  • the reaction can be carried out under normal pressure or pressurized conditions, so that the reaction can usually be carried out more easily than in the gas phase system. That is, in the present invention, the liquid phase method is recommended from the viewpoint of operation.
  • the temperature in the system at the time of carrying out this reaction is preferably in the range of 110 ° C. to + 10 ° C., and particularly preferably in the range of 0 ° C. to + 50 ° C.
  • 1,1,1-tritrifluoromethyl-2-propanol is by-produced in addition to the target product 1,1-dichloro-1,3,3,3-trifluoro-2-propanol.
  • the temperature range below 50 ° C the formation of the latter is suppressed to a small extent, and 1,1 dichloro-1,3,3,3-trifluoro-2-propanol can be obtained as the main component.
  • the selectivity of 1,1-dichloro mouth—3,3,3-trifluoro-2-propanol is particularly high, so that 1,1-dichloro-3,3,3 This is particularly effective when only 3-trifluoro-2-propanol is the target substance.
  • reaction temperature is higher than 100 ° C, the amount of 1,1,1-trifluoromethyl-2-propanol increases, so the desired 1,1-dichloro-3,3,3-trifluoro- 2- The selectivity of propanol decreases. Conversely, when the temperature is lower than 110 ° C., it is not preferable because not only the reaction rate is reduced but also the raw material may be solidified.
  • a catalyst containing at least platinum is present in the system.
  • a solid phase catalyst in which a compound containing platinum is supported on a carrier such as activated carbon, silica, or alumina is preferred.
  • the target reaction proceeds even if palladium, ruthenium, iridium, or rhodium is present as a catalyst other than platinum as a metal.
  • a solid phase catalyst in which these metals are supported on a carrier together with platinum corresponds to this.
  • these metals have the effect of hydrogenating the 1,1-dichlorofluoromethyl group and increase the by-products such as 1,1,1-trifluoromethyl 2-propanol.
  • the higher the number the lower the yield of the desired 1,1-dichloro mouth—3,3,3-trifluoromethylacetone. Therefore, when only 1,1-dichloro-3,3,3-trifluoromethylacetone is intended, it is particularly preferable to use a catalyst containing no metal other than platinum.
  • a known method may be used. That is, an aqueous solution of a metal compound (for example, hexacloplatinum (IV) acid hexahydrate (H 2 [PtCl 6 ] ⁇ 6H 20 ) or palladium nitrate) is added to a carrier such as activated carbon, silica, or alumina.
  • a metal compound for example, hexacloplatinum (IV) acid hexahydrate (H 2 [PtCl 6 ] ⁇ 6H 20 ) or palladium nitrate
  • a carrier such as activated carbon, silica, or alumina.
  • the solid phase catalyst can be prepared by means of dipping and spraying, drying, and heating to about 150 to 350 ° C while flowing hydrogen gas or the like. Alternatively, a commercially available solid phase catalyst can be used.
  • the supported amount of the metal is preferably in the range of 0.01 wt% to 20 wt% (amount converted into metal atoms) with respect to the carrier, and the supported amount of 0.51;% to 51;% is particularly preferable.
  • the catalyst prepared in this way can be used as a dry product that does not contain moisture or as a wet product that has been conditioned in advance. However, the dry product may ignite in the air, so handling with care is required. Since the present invention is characterized by adding water to the system, a wet product is recommended from the viewpoint of safety.
  • the amount of the catalyst to be added in carrying out the reaction of the present invention is not necessarily limited, but the weight of the solid catalyst prepared as described above, excluding water, is 1,1-dichloro-1,3,3,3. -It is appropriate to be in the range of 0.5 wt% to 30 wt% based on trifluoroacetone. If the amount of catalyst added is less than this, the reaction time may be extremely long, or the reaction may be stopped halfway. Conversely, when a large amount of the catalyst is used, no particularly useful effect on the reactivity is observed, which is economically disadvantageous. In addition, since these catalysts are solid phase catalysts, they can be easily recovered and reused after the completion of the reaction.
  • a basic compound eg, NaOH, KOH, LOH
  • a basic compound eg, NaOH, KOH, LOH
  • JP-A-63-280035 a basic compound
  • the pressure in the reaction system is not particularly limited, but is preferably in the range of normal pressure (0.IMPa) to 5 MPa, particularly in the range of 0.5 MPa to 3 MPa. preferable.
  • the higher the reaction pressure the more advantageous in terms of chemical equilibrium.
  • a reactor coated with polytetrafluoroethylene or the like as a material inside the reaction group of the liquid phase type is recommended in terms of corrosion resistance.
  • materials such as stainless steel and glass are susceptible to corrosion, and therefore, it is not preferable to use them as materials inside the reaction group.
  • the raw materials 1,1-dichloro-3,3,3-trifluoroacetone, water, and the catalyst are charged in predetermined amounts into a reaction group capable of withstanding the pressurized condition.
  • the container is sealed, and stirring in the container is started.
  • hydrogen gas may be supplied continuously or intermittently so that the inside of the reactor is maintained at a predetermined pressure at a predetermined temperature.
  • analysis of the reaction mixture may be appropriately analyzed by means such as gas chromatography, and the reaction may be continued until the raw materials are sufficiently consumed.
  • the reaction time is not particularly limited and varies depending on the conditions, but if the reaction is continued for a long time after the raw materials have been sufficiently consumed, the generated 1,1-dichloro-3,3,3-trifluoro-2-propanol is further increased. Hydrogenation is not preferred because the yield of the desired product may be rather reduced.
  • 1,1,1-trifluoro-2-propanol from 1,1-dichloro-3,3,3-trifluoroacetone
  • 1,1 dichloro-mouth 3,3,3-trifluoroacetone is used as a raw material, and this is brought into contact with hydrogen gas in the presence of water and in the presence of a catalyst containing at least platinum.
  • 1,1-dichloro-3,3,3-trifluoro-2-propanol and 1,1,1-trifluoro-2-propanol are produced simultaneously. Therefore, the production methods of both compounds are basically common.
  • R2-propanol is used as the target substance, not only a platinum-only catalyst, but also a metal such as palladium, ruthenium, iridium or rhodium (which is added to ) Is more preferable because the hydrogenation of the dichloromethyl group in the raw material is promoted and the selectivity of 1,1,1,1-trifluoro-2-propanol is increased.
  • a metal such as palladium, ruthenium, iridium or rhodium (which is added to )
  • the weight ratio of platinum to the added metal but if the amount of platinum is too small, the reduction of the carbonyl group of the raw material compound will not proceed easily, so the amount of 1,1,1-trifluoromethylacetone produced Results in an increase in the selectivity of the target product.
  • the number of moles of the added metal relative to 1 mole of platinum is preferably within 2 and more preferably within 1.5. It is an example of a particularly preferred embodiment that the molar ratio of platinum to the additional metal is set to around 1: 1.
  • the reaction temperature in the production of 1,1-dichloro-3,3,3-trifluoro-2-propanol, the range of 0 ° C. to 5 Ot was particularly suitable.
  • the temperature is preferably from 50: 150 ° C, more preferably from 80 ° C to 150 ° C.
  • the temperature is lower than 50, the production of 1,1-dichloro-3,3,3-trifluoro-2-propanol becomes relatively large.
  • the formed 1,1-dichloro-3,3,3-trifluoro-2-propanol can be further reduced and converted to the desired 1,1,1,1-trifluoro-2-propanol, It is not preferable because it takes a long time.
  • the target reaction proceeds even at a temperature higher than 150 ° C., it is not preferable because hydrogenation of a trifluoromethyl group and by-product of hydrofluoric acid accompanying the hydrogenation are likely to occur. In this reaction, the addition of water is essential.
  • 1,1,1 trifluoro-2-propanol the production of 1,1, dichloro-3,3,3—trifluoro mouth—2-propanol is higher than that of producing 2-propanol.
  • water it is preferred to add more water. Specifically, it is preferable to add water in a range of 10 to 40 moles to 1 mole of 1,1-dichloro-3,3,3-trifluoroacetone, and more preferably from 20 to 40 moles. It is further preferred to add 30 times the molar amount of water. By the addition of this water, hydrogen chloride produced as a by-product of the reaction is detoxified, and a decrease in the activity of the catalyst accompanying the reaction is suppressed, so that the reaction can be continued in a stable state.
  • the method may be a known method for organic compounds, and is not particularly limited.
  • a dehydrating agent such as concentrated sulfuric acid, zeolite, calcium chloride, and magnesium sulfate is added to remain. Remove moisture.
  • concentrated sulfuric acid is particularly recommended.
  • the flash point was measured by the method specified by the Fire Service Law. As a result, no flash point was obtained. Solvents, cleaning agents, draining agents, etc. Excellent in safety when used in applications. It is also possible to add methanol, ethanol, isopropyl alcohol, etc. to control the cleaning and draining properties. The addition amount of these alcohols is optional, but 1,1-dichloro-3,3,3-trif
  • the content is preferably from lwt% to 30 wt%, more preferably from 5 to 15 wt%, based on Luoro 2-propanol.
  • the surface tension of 1,1-dichloro-3,3,3-trifluoro-2-propanol was measured and found to be 26.4 mN / m, which is 2,2,3,3-tetrafluoropropanol (currently used).
  • the result was almost the same as CHF 2 CF 2 CH 2 ⁇ H, 26.5 mN / m), so it can be used as a substitute for nonflammable solvents.
  • Optical storage media such as CD-R and DVD-R use dyes such as cyanine, phthalocyanine, and azo dyes dissolved in a solvent and apply the dye to the base. Since 3,3,3-trifluoro-2-propanol has a fluorine atom and a hydroxyl group, it can be used as a solvent for the dye, and shows good solubility in these.
  • 1,1-dichloro-3,3,3-trifluoro-2-propanol and 1,1,1-trifluoro-2-propanol have hydroxyl groups, so they contain fluorine-containing building blocks for pharmaceuticals, agricultural chemicals, etc. It is very promising.
  • a piece of ice is added little by little to 1,1 dichloro mouth, 33,3 trifluoroacetone (purity: 99.5%), which has been dehydrated with sulfuric acid in advance, and 1,1 dichloro-3,3,3-trifluoro
  • An aqueous solution having a molar ratio of loacetone to water of 1:20 was prepared. 50 g of this aqueous solution into a pressure-resistant glass container with an internal volume of 100 Om 1 and 5 wt% PtZC powder manufactured by Degussa Japan Co., Ltd.
  • 1,1-dichloro-1,3,3,3-trifluoroacetone (raw material): trace amount
  • 1,1-chloro-3,3,3-trifluoroacetone Trace amount
  • 1, 1, 1-trifluoroacetone 3.4%
  • 1,1,1-trifluoro-2-propanol 53.6%
  • 1,1-dichloro-3,3,3-trifluoro-2-propanol 41.2%.
  • Ice chips (270 g) were added little by little to 1,1-dichloro-3,3,3-trifluoroacetone (purity: 99.5%, 180 g), which had been previously dehydrated with sulfuric acid.
  • An aqueous solution of 1-dichloro-3,3,3-trifluoroacetone was prepared.
  • To a 1.5 liter polytetrafluoroethylene-lined autoclave add this aqueous solution (450 g) and Degussa Japan Co., Ltd. 5 wt% PtZC powder 50% water-containing product (catalyst in which 5 g of platinum in terms of metal atoms is supported per 100 g of activated carbon, and moisture is adjusted so that the water content becomes 50 wt%) 18 g I charged.
  • the fraction at an overhead temperature of 122 ° C to 124 ° C was recovered as the main fraction.
  • the purity of 1,1 dichloro-opening-3,3,3-trifluoro-2-propanol was 99% or more.
  • the main fraction the CD C 1 3 in a solvent NMR (JEOL 400 MHz FT-NMR (shed - 400)) was analyzed, the following results were obtained.
  • FIGS. 1-3 shows a chart of the NMR.
  • Example 3 The flash point of 1,1-dichloro-3,3,3-trifluoro-2-propanol (purity: 99% or more) obtained in Example 2 was measured by the method specified by the Fire Service Law. In other words, the flash point from 20 ° C to 80 ° C was measured using the closed tag type, but no flash phenomenon was observed. Next, the flash point from 20 ° C to 123 was measured by the Cleveland method. No flash phenomenon was observed up to 123 ° C. At around 123 ° C, 1,1-dichloro-3,3,3- The trifluoro-2-propanol boiled and the test flame extinguished. Based on the above, it was determined that there was no flash point. The environment of the measurement room at this time was room temperature 20 ° (:, atmospheric pressure 1024 hPa, relative humidity 39%).
  • the surface tension of 1,1-dichloro_3,3,3-trifluoro-2-propanol (purity of 99% or more) obtained in Example 2 was measured using an automatic surface tension measurement device (CBVP-A3 manufactured by Kyowa Kaimen Kagaku Co., Ltd.). (Type). Measured at 23 ° C after calibration with benzene, pure water, HC FC_141 b. As a result, the surface tension of 1,1-dichloro-3,3,3-trifluoro-2-propanol was 26.4 mN / m.
  • Dye (copper (II) 1,2,3,4,8,9,10,11,15,16,17,18) in 100 g of 1,3 dichloro-1,3-, 3-trifluoro-2-propanol , 22, 23, 24, 25-hexadecidium fluoro-29H, 31H-monophthalocyanine) was added, and the mixture was heated and stirred at 50 ° C. After standing at room temperature for 24 hours, it was found to be well dissolved by visual observation.
  • Example 7 1.0952 g of flux for solder was applied to a glass plate and heated at 120 ° C for 10 minutes. This glass plate was placed in a mixed solution of 500 g of 1,1-dichloro-3,3,3-trifluoro-2-propanol and 50 g of 2-propanol, and washed with an ultrasonic cleaner for 5 minutes. After taking out the glass plate and draining the solution, put the glass plate into a new solution of 1,1-dichloro-3,3,3-trifluoro-2-propanol and finish ultrasonic cleaning for 1 minute. went. As a result of measuring the weight of the dried glass plate, no increase in the mass of the glass plate was observed. This indicates that the flux was successfully removed.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Microbiology (AREA)
  • Mycology (AREA)
  • Food Science & Technology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Zoology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Detergent Compositions (AREA)

Abstract

Selon la présente invention, il convient de mettre du 1,1-Dichloro-3,3,3-trifluoroacétone en contact avec de l'hydrogène en présence d'eau et d'un catalyseur renfermant du platine pour obtenir du 1,1-dichloro-3,3,3-trifluoro-2-propanol. La température de réaction est idéalement comprise entre 0 et 50 °C. Le 1,1-dichloro-3,3,3-trifluoro-2-propanol obtenu présente d'excellentes performances lorsqu'il est utilisé comme solvant, détergent, etc. Il est également utilisé comme intermédiaire pour des médicaments ou des produits chimiques agricoles ou comme motif structural pour des composés organiques.
PCT/JP2003/010729 2002-08-30 2003-08-26 Alcool halogene et son procede de production WO2004020376A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2002-253341 2002-08-30
JP2002253341A JP2004091368A (ja) 2002-08-30 2002-08-30 含ハロゲンアルコールおよびその製造方法

Publications (1)

Publication Number Publication Date
WO2004020376A1 true WO2004020376A1 (fr) 2004-03-11

Family

ID=31972790

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2003/010729 WO2004020376A1 (fr) 2002-08-30 2003-08-26 Alcool halogene et son procede de production

Country Status (2)

Country Link
JP (1) JP2004091368A (fr)
WO (1) WO2004020376A1 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100730635B1 (ko) * 2004-12-07 2007-12-11 한국전자통신연구원 서비스 지향 자동 원격 제어 시스템, 원격 제어 방법,원격지 서버 및 원격제어 에이전트
JP6183803B2 (ja) * 2012-10-04 2017-08-23 ヤクルトヘルスフーズ株式会社 Ｈｓｐ発現促進剤

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10012168A1 (de) * 1999-03-19 2000-09-21 Lonza Ag Verfahren zur Herstellung von 3.3Dichlor-1,1,1-trifluoraceton
EP1127865A1 (fr) * 2000-02-22 2001-08-29 Central Glass Company, Limited Procédé de préparation de 1,1,1-Trifluoroacétone
JP2001253841A (ja) * 2000-01-05 2001-09-18 Central Glass Co Ltd ３−塩素化−１，１，１−トリフルオロ−２−置換−２−プロパノール類の製造方法
JP2003089666A (ja) * 2001-09-18 2003-03-28 Asahi Glass Co Ltd ハロゲン化アルコ−ルの製造方法

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10012168A1 (de) * 1999-03-19 2000-09-21 Lonza Ag Verfahren zur Herstellung von 3.3Dichlor-1,1,1-trifluoraceton
JP2001253841A (ja) * 2000-01-05 2001-09-18 Central Glass Co Ltd ３−塩素化−１，１，１−トリフルオロ−２−置換−２−プロパノール類の製造方法
EP1127865A1 (fr) * 2000-02-22 2001-08-29 Central Glass Company, Limited Procédé de préparation de 1,1,1-Trifluoroacétone
JP2003089666A (ja) * 2001-09-18 2003-03-28 Asahi Glass Co Ltd ハロゲン化アルコ−ルの製造方法

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
BROWN,H.C. ET AL.: "Markovnikov Hydroboration of Perfluoroalkylethylenes.", ANGEW.CHEM.INT.ED., vol. 38, no. 13-14, 1999, pages 2052 - 2054, XP002974188 *

Also Published As

Publication number Publication date
JP2004091368A (ja) 2004-03-25

Similar Documents

Publication Publication Date Title
EP3024810B1 (fr) Hydrofluoroéthers contenant de l'azote et procédés pour leur préparation
EP2215097A1 (fr) Synthèse d'hydrofluoroalcanols et d'hydrofluoroalcènes
WO2011010606A1 (fr) Procédé de production du 2-chloro-3,3,3-trifluoropropène
KR20140008406A (ko) 시스-1-클로로-3,3,3-트리플루오로프로펜의 제조
JP2011168509A (ja) ３，３，３−トリフルオロプロペンの製造方法
WO2004020376A1 (fr) Alcool halogene et son procede de production
JPH09508165A (ja) 洗浄溶剤及び脱脂溶剤としてのヒドロフルオロアルカン
EP1127865B1 (fr) Procédé de préparation de 1,1,1-Trifluoroacétone
JPS6144834A (ja) ２，２，２‐トリフロロエタノールおよび１，１，１，３，３，３‐ヘキサフロロイソプロピルアルコールの合成方法
TW593301B (en) Processes for producing fluorinated cyclic ethers and use thereof
CA2007874A1 (fr) Hydrogenolyse selective de derives perhalogenes de l'ethane
JP2712475B2 (ja) ジフルオロメチレン基を有するプロパンの製造法
JPH04224528A (ja) フッ素含有エタン誘導体、触媒混合物、およびフッ化水素溶液の製造方法
JP2712476B2 (ja) ジフルオロメチレン基を有するプロパンの製造法
JP2002526385A (ja) 弗化物の少ない有機化合物の製法
US5124495A (en) Selective hydrogenolysis of perhalogenated ethane derivatives
RU2801356C1 (ru) Способ получения алканового соединения
US5569796A (en) Process for producing fluorinated saturated hydrocarbon
JP5605130B2 (ja) 含フッ素アルコールの製造方法
JPH0717881A (ja) フツ素及び他のハロゲンを含有するｃ１化合物を気相中で開裂する方法
JP2648903B2 (ja) ポリフルオロ第３級アミン及びその製造方法
JP3995451B2 (ja) １，１，１−トリフルオロアセトンの製造方法
JP2862130B2 (ja) ポリフルオロ第３級アミンの製造方法
JPH02202825A (ja) １，１，１―トリクロロ―２，２，３―トリフルオロプロパン
WO2005102975A1 (fr) Procédé de fabrication d’éther fluoré

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CN US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR

121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase