WO2011021491A1 - ヘキサフルオロアセトン一水和物の製造方法 - Google Patents
ヘキサフルオロアセトン一水和物の製造方法 Download PDFInfo
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- WO2011021491A1 WO2011021491A1 PCT/JP2010/062878 JP2010062878W WO2011021491A1 WO 2011021491 A1 WO2011021491 A1 WO 2011021491A1 JP 2010062878 W JP2010062878 W JP 2010062878W WO 2011021491 A1 WO2011021491 A1 WO 2011021491A1
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- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
- C07C29/82—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation by azeotropic distillation
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- the present invention relates to a method for producing hexafluoroacetone monohydrate (1,1,1,3,3,3-hexafluoropropane-2-diol), and more particularly, hexafluoroacetone hydrate is organically synthesized.
- the present invention relates to a method for dehydration in the presence of a solvent.
- Hexafluoroacetone is an important compound as a pharmaceutical intermediate or reaction raw material.
- Hexafluoroacetone is industrially produced by epoxidation of hexafluoropropene followed by isomerization, hexachloroacetone obtained by chlorinating acetone with hydrogen fluoride using a chromium activated carbon supported catalyst, etc.
- Hexafluoroacetone is a gas having a boiling point of ⁇ 28 ° C. at atmospheric pressure, and therefore, for convenience in handling, hexafluoroacetone trihydrate, which can be handled as a constant boiling point composition at 106 ° C., is used as a raw material in many reactions. Has been or is stored.
- hexafluoroacetone monohydrate may be required depending on the reaction conditions, target product and other requirements. It is known that hexafluoroacetone monohydrate can introduce, for example, a hexafluoroisopropanol group at the 5-position of uracil (Non-patent Document 1).
- Hexafluoroacetone monohydrate is a crystal having a gem-diol structure with a melting point of 46 ° C. and decomposes simultaneously with melting to disproportionate to hexafluoroacetone and hexafluoroacetone trihydrate (Patent Document 1), It is an unstable compound that is very difficult to handle and difficult to obtain because it deliquesces immediately with moisture in the air even at low temperatures.
- hexafluoroacetone monohydrate hexafluoroacetone is absorbed into water in two steps, and hexafluoroacetone monohydrate is obtained as slightly wet needle-like white crystals containing some hexafluoroacetone and water. (Patent Document 1).
- hexafluoroacetone monohydrate is an unstable compound with deliquescence as described above, even if hexafluoroacetone monohydrate is dissolved in a solvent, water or hexafluoroacetone trihydrate cannot be dissolved. A solution containing hexafluoroacetone monohydrate and a solvent is obtained, which is substantially free of water.
- the present invention provides a method for producing hexafluoroacetone monohydrate substantially free of water, and also provides a composition of hexafluoroacetone monohydrate in a form that is easy to handle.
- the present inventors have made hexafluoroacetone monohydrate (1,1,1,3,3) substantially free of water from aqueous solutions containing hydrates such as hexafluoroacetone or hexafluoroacetone trihydrate.
- 3-Hexafluoropropane-2-diol was studied, and when the molar ratio of hexafluoroacetone to water was adjusted to obtain hexafluoroacetone monohydrate, it was carried out in the presence of an organic solvent.
- hexafluoroacetone monohydrate was found to exist stably above the melting point, and the present invention was reached. It has also been found that a composition comprising hexafluoroacetone monohydrate and an organic solvent obtained by this production method is useful for various uses and storage.
- the present invention is as follows.
- a method for producing hexafluoroacetone monohydrate comprising obtaining a composition comprising hexafluoroacetone monohydrate and an organic solvent as components.
- Invention 2 The production method of Invention 1, wherein at least one of hexafluoroacetone hydrate and an organic solvent is continuously introduced into a distillation column.
- Invention 5 The production method of Invention 1, wherein an azeotropic composition of hexafluoroacetone monohydrate and an organic solvent is obtained from a composition containing hexafluoroacetone monohydrate and an organic solvent obtained from the tower bottom.
- a hexafluoroacetone having a number of moles equal to the total number of moles of water and hexafluoroacetone hydrate present in the system is introduced into a solution system in which water or hexafluoroacetone hydrate coexists with an organic solvent.
- a method for producing hexafluoroacetone monohydrate comprising obtaining a composition comprising hexafluoroacetone monohydrate and an organic solvent.
- Invention 10 A process for producing a hexafluoroacetone derivative according to Invention 8 or 9, wherein the organic solvent is an aromatic compound or an ether compound.
- composition substantially free of water comprising hexafluoroacetone monohydrate and an organic solvent.
- Invention 12 The composition of Invention 11, wherein the organic solvent is an aromatic compound or an ether compound.
- FIG. 3 is a 13 C-NMR chart of the composition obtained in Example 1.
- the production method of the present invention is capable of easily producing hexafluoroacetone monohydrate substantially free of water from a hydrate such as hexafluoroacetone trihydrate without using a special dehydrating agent. Play.
- composition comprising hexafluoroacetone monohydrate and an organic solvent of the present invention has an effect that hexafluoroacetone monohydrate can be used as a reagent that can be handled as a stable reaction substrate.
- hexafluoroacetone may be represented as “HFA”.
- hexafluoroacetone monohydrate may be expressed as “HFA ⁇ W”.
- hexafluoroacetone trihydrate may be expressed as “HFA ⁇ 3W”.
- hexafluoroacetone hydrate refers to a hydrate that does not limit the number of hydration or an aqueous solution thereof, and is a concept including “HFA ⁇ 3W”.
- the organic solvent solution of hexafluoroacetone monohydrate of the present invention is a composition comprising hexafluoroacetone monohydrate and an organic solvent.
- the organic solvent include aromatic compounds, ether compounds, and halogen solvents that are liquid at room temperature (about 25 ° C.).
- the aromatic compound is not particularly limited and may be any of monocyclic, ring assembly, and condensed polycyclic, but monocyclic benzene or a hydrogen atom of benzene is a halogen atom, an alkyl group, a fluoroalkyl group, etc. Compounds substituted with are preferred.
- Examples of such compounds include benzene, toluene, xylene, ethylbenzene, chlorobenzene, benzotrifluoride, 2,4-dichlorobenzotrifluoride, o-, m- or p-bistrifluoromethylbenzene.
- Examples of the ether compound include chain ethers such as dimethyl ether, diethyl ether, isopropyl ether, ethyl isopropyl ether, butyl methyl ether, and ethyl butyl ether, and cyclic ethers such as tetrahydrofuran, pyran, and dioxane.
- halogen solvent examples include carbon tetrachloride, chloroform, dichloromethane, 1,2-dichloroethane, cis-1,2-dichloroethylene, trans-1,2-dichloroethylene, 1,1,2-trichloroethane, and the like.
- the organic solvent can be appropriately selected depending on the purpose of use, particularly the purpose of reaction. Moreover, these can also be used in combination of 2 or more types.
- an organic solvent an aromatic compound or an ether compound is preferable, and an aromatic compound is more preferable.
- the aforementioned organic solvent azeotropic with water is preferable.
- the concentration of hexafluoroacetone monohydrate may be determined so as to be a desired concentration, but is usually 1 to 1000 parts by mass with respect to 1 part by mass of hexafluoroacetone, and can be determined according to the application.
- the hexafluoroacetone monohydrate according to the present invention can be produced by the “hydration method” and “dehydration method” described later.
- Hexafluoroacetone trihydrate is a dihydrate of hexafluoroacetone monohydrate, which is a gem-diol produced by the reaction of hexafluoroacetone and water (herein the dihydrate 2
- the water corresponding to is called “additional water”), It is a stable liquid having the highest azeotropic composition (boiling point 106 ° C.).
- hexafluoroacetone monohydrate is a solid having a melting point of 46 ° C., but decomposes to disproportionate to anhydrous hexafluoroacetone and hexafluoroacetone trihydrate above the melting point (Patent Document 1). ).
- the hexafluoroacetone monohydrate according to the present invention is obtained by adding water in the system (additional water) to a hydrate of hexafluoroacetone, for example, a mixture comprising an aqueous solution containing hexafluoroacetone trihydrate or hexafluoroacetone and an organic solvent. And free water) and an equimolar amount of hexafluoroacetone can be added and dissolved in an organic solvent.
- hexafluoroacetone trihydrate As hexafluoroacetone hydrate, it is preferable to use hexafluoroacetone trihydrate, which is easily available. It may be a hydrate having a lower hydration number than trihydrate or an aqueous solution of hexafluoroacetone trihydrate. Hexafluoroacetone may be used in such an amount that the number of moles is equal to the amount of water contained in these hexafluoroacetone-related substances, and hexafluoroacetone / water (the sum of added water and free water) is substantially reduced. 1 is preferred, but usually 1 to 1.2. A slight excess amount may be allowed in consideration of operational loss and the like.
- hexafluoroacetone is excessive, it is not preferable because it is washed away. If insufficient, free water or hexafluoroacetone trihydrate is used. Since it remains in the organic solvent solution, it is not preferable. However, when water remains, the water can be removed by a “dehydration method” to be described later to obtain a target hexafluoroacetone monohydrate solution.
- the liquid portion in the system When introducing hexafluoroacetone into the system, it is preferable to heat the liquid portion in the system at 40 ° C. or higher and below the boiling temperature of the liquid. This is because a sufficient reaction rate cannot be obtained at a low temperature. As the reaction proceeds, the temperature of the reaction system increases and decreases with the completion of the reaction. Therefore, although the temperature in the system varies depending on the type of organic solvent, it is usually set to a boiling point (106 ° C.) or less of hexafluoroacetone trihydrate.
- the amount ratio of the organic solvent and hexafluoroacetone may be determined so that the solution of hexafluoroacetone monohydrate has a desired concentration, but is usually 1 to 1000 parts by mass with respect to 1 part by mass of hexafluoroacetone, 1 to 100 parts by mass is preferable. If the organic solvent is too small, depending on the shape and method of the reactor, the produced hexafluoroacetone monohydrate precipitates during production, which makes it difficult to stir or the exothermic removal is not smooth, If it is excessive, there is no problem with stirring, but it is not preferable because it causes disadvantages such as an increase in the size of the apparatus and a small concentration of the produced hexafluoroacetone monohydrate solution.
- a predetermined amount of hexafluoroacetone trihydrate and an organic solvent according to the purpose are introduced into a closed reaction vessel equipped with a stirrer and a gas inlet.
- the reaction apparatus is not particularly limited, but is preferably a pressure vessel or a vessel equipped with a condenser, and preferably a stirrer.
- a pressure vessel or a vessel equipped with a condenser, and preferably a stirrer.
- a material of the apparatus stainless steel, nickel alloy steel, glass, fluororesin, carbon, polyethylene, or a material lined or clad with these materials can be used.
- the hexafluoroacetone monohydrate according to the present invention dehydrates an excess amount of water from a mixture of hexafluoroacetone hydrate, for example, hexafluoroacetone trihydrate or an aqueous solution containing hexafluoroacetone and an organic solvent. Thus, it can be obtained in a state dissolved in an organic solvent.
- hexafluoroacetone hydrate and organic solvent charged in a container are heated to remove excess or free water as a gas phase component, and hexafluoroacetone monohydrate and organic solvent are removed from the liquid phase part.
- a method for obtaining a composition comprising: The removed water can be removed by azeotroping with an organic solvent.
- This dehydration method is usually performed using a general distillation apparatus equipped with a distillation can, a distillation column, a condenser and other devices.
- the distillation apparatus may be of any type, but as the distillation tower, any of simple distillation, packed tower, bubble bell tower, plate tower, etc. can be adopted, and the packing material is not particularly limited. Any of helipac, pole ring, etc. may be used.
- As the distillation format any of a batch method, a semi-batch method, a semi-continuous method, or a continuous method in which either an organic solvent or hexafluoroacetone hydrate is continuously supplied can be adopted.
- As the material of the apparatus stainless steel, nickel alloy steel, glass, fluororesin, carbon, polyethylene, or a material lined or clad with these materials can be used.
- Hexafluoroacetone hydrate and the organic solvent according to the purpose can be mixed in advance or separately introduced into the distillation apparatus.
- hexafluoroacetone hydrate is pre-treated with an adsorbent such as a chemical substance or molecular sieve generally used as a “dehydrating agent” such as concentrated sulfuric acid, anhydrous sulfuric acid, or phosphorus pentoxide in advance. It may be removed.
- distillation since dehydration is performed by azeotropic distillation, it is an organic solvent azeotropic with water.
- the tower top temperature is determined by the azeotropic temperature of water and the organic solvent, and varies depending on the type of organic solvent.
- this temperature range is also referred to as an azeotropic temperature in this specification.
- the azeotropic temperature of water and organic solvent includes water / benzene 69.25 ° C., water / toluene 85.0 ° C., water / m-xylene 94.5 ° C., water / ethylbenzene 92 ° C., etc.
- the distillation operation can be carried out in the range of about 5 ° C. up and down.
- the water and the organic solvent recovered from the top of the column are condensed, they are separated into a layer containing the organic solvent as a main component and a layer containing water.
- the organic solvent can be used again in the process of the present invention.
- the layer containing water may contain hexafluoroacetone hydrate, hexafluoroacetone trihydrate can be recovered therefrom and used again in the method of the present invention.
- the column bottom temperature may be a temperature at which distillation can be maintained, and is 50 ° C. to 120 ° C.
- Hexafluoroacetone monohydrate is known to decompose at 48 ° C. alone, but even when the column bottom temperature is 50 ° C. or higher, hexafluoroacetone monohydrate does not decompose, Acetone monohydrate is stably present at the bottom of the column as an organic solvent solution.
- the amount of the organic solvent required for hexafluoroacetone trihydrate varies depending on the type, but it is required to be more than the amount that azeotropically removes water.
- the solution of hexafluoroacetone monohydrate is determined so as to have a desired concentration, but it is usually 1 to 1000 parts by weight, preferably 1 to 100 parts by weight with respect to 1 part by weight of hexafluoroacetone.
- the dehydration method can be performed under reduced pressure or under pressurized conditions. It is preferable to carry out at normal pressure. Below, the case where it carries out by a normal pressure (0 Mpa-G (gauge pressure)) is demonstrated. It is also within the scope of the present invention to perform under other pressure conditions.
- a new reflux is observed at a temperature determined by the azeotropic composition of hexafluoroacetone monohydrate and organic solvent, and a mixture of hexafluoroacetone monohydrate and organic solvent distills from the top of the column. In some cases, it may be obtained as an azeotropic composition. In this way, a component composed of hexafluoroacetone monohydrate and an organic solvent and a component composed of water and an organic solvent are obtained separately. The composition of water and organic solvent recovered from the top of the column is separated into two layers, and the organic solvent from which water has been separated and removed can be used again in this process.
- the dehydration method of the present invention can be applied to a method for producing a hexafluoroacetone derivative.
- an organic solvent is added to hexafluoroacetone trihydrate or its aqueous solution, which is usually readily available prior to the reaction, and the organic solvent and water are removed by azeotropic distillation by applying the dehydration method described above.
- hexafluoroacetone monohydrate containing no water can be used as a reaction reagent.
- hexafluoroacetone trihydrate or an aqueous solution thereof and an organic solvent, which are usually easily available are added to the reaction vessel, and the above-described dehydration method is applied during the reaction to share the organic solvent and water. By removing by boiling distillation, the reaction concerning hexafluoroacetone monohydrate not containing water can be performed.
- Example 1 Hydrolysis method A stirrer, a dry ice / acetone cooled reflux condenser, a thermometer, and a gas inlet are provided, and the opening of the reflux condenser is made of a closed system with a balloon. 86 g (100 mL) and 22 g (0.1 mol) of HFA ⁇ 3W were added, and 32 g (0.2 mol) of HFA was gradually introduced from the gas inlet while the outside was ice-cooled. After confirming that the temperature of the solution became room temperature or lower, the reaction was terminated to obtain 139 g of a colorless transparent solution having a specific gravity of 1.05 (yield 98%).
- Example 2 Hydrolysis method Hexafluoroacetone monohydrate was produced in the same manner as in Example 1 except that 72.5 g of isopropyl ether was used instead of toluene. After completion of the reaction, 127 g of a colorless transparent solution having a specific gravity of 1.00 was obtained (yield 100%).
- Example 3 Dehydration method HFA ⁇ 3W 22 g (0.1 mol) and benzene 38 g (0.49 mol) were placed in a 100 mL eggplant-shaped flask equipped with a glass reflux distillation column and a 20 cm distillation column (empty column). The mixture was heated in an oil bath while stirring with a stir bar. The water / benzene azeotrope (white turbidity at the time of condensation) distilled at 69 ° C. to 71 ° C., and the distillation was temporarily stopped when the distillation temperature at the top of the column rose to 73 ° C.
- the distillate was separated into two layers, and a benzene layer was formed in the upper layer and an aqueous layer was formed in the lower layer (benzene layer: 6.8 g, specific gravity 0.87, aqueous layer: 3.6 g, specific gravity 1.15). Since the specific gravity of the aqueous layer was larger than 1, it was suggested that some HFA components were mixed. Further distillation continued to distill a new azeotropic composition at 73.8-74.0 ° C. Distilled 40 g of a uniform, colorless and transparent liquid having a specific gravity of 1.04 was obtained by hexafluoroacetone monohydrate (1,1,1) in benzene by NMR ( 13 C, H, F) and FR-IR measurement.
- Example 4 Dehydration Method Hexafluoroacetone monohydrate was produced by the same dehydration method as Example 3 except that 54 g of metaxylene was used instead of benzene. Distillation of the azeotropic composition began at 94 ° C., which is the lowest azeotropic temperature of meta-xylene and water, and distillation of a liquid that became cloudy when condensed continued to a distillation temperature of 97 ° C. The distilled liquid was separated into two layers, and a metaxylene layer was formed in the upper layer and an aqueous layer was formed in the lower layer (metaxylene layer: 1.2 g, specific gravity 0.86, aqueous layer: 7.4 g, specific gravity 1.37). ).
- the specific gravity of the aqueous layer was considerably larger than 1, suggesting that the HFA component was mixed.
- a uniform, colorless and transparent liquid with a specific gravity of 1.03 of 67.4 g remaining in the kettle is a meta-xylene solution of HFA ⁇ W 29.9% by mass, measured by NMR ( 13 C, H, F) and FR-IR measurement.
- Only hexafluoroacetone monohydrate (1,1,1,3,3,3-hexafluoropropane-2-diol) is present in xylene, and moisture is measured with a Karl Fischer moisture analyzer. The ratio of water to water was confirmed to be 1: 1.
- the yield of hexafluoroacetone monohydrate by this dehydration method was 70.4%.
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Abstract
Description
[発明1]ヘキサフルオロアセトン水和物と有機溶媒をあらかじめ混合してまたは別々に蒸留塔に導入し、低沸点成分として塔頂から有機溶媒と水を含む組成物を得、塔底から高沸点成分としてヘキサフルオロアセトン一水和物および有機溶媒を含む組成物を得ることからなるヘキサフルオロアセトン一水和物の製造方法。
本発明にかかるヘキサフルオロアセトン一水和物は、ヘキサフルオロアセトンの水和物、例えばヘキサフルオロアセトン三水和物またはヘキサフルオロアセトンを含む水溶液と有機溶媒からなる混合物へ系内の水(付加水とフリーの水)と当モルのヘキサフルオロアセトンを添加することで有機溶媒に溶解した状態で得ることができる。
本発明にかかるヘキサフルオロアセトン一水和物は、ヘキサフルオロアセトンの水和物、例えばヘキサフルオロアセトン三水和物またはヘキサフルオロアセトンを含む水溶液と有機溶媒からなる混合物から過剰量の水を脱水することで有機溶媒に溶解した状態で得ることができる。
攪拌装置、ドライアイス/アセトン冷却還流器、温度計、ガス導入口を備え、還流器の開口部は風船で閉鎖系としたガラス製の200mL四つ口反応装置にトルエン86g(100mL)、HFA・3W 22g(0.1モル)を入れ、外部を氷冷しながらガス導入口からHFA 32g(0.2モル)を徐々に導入し、所定量導入した後、反応液の温度が室温以下になったことを確認して反応を終了し、比重 1.05の無色透明溶液139gを得た(収率98%)。
トルエンの代わりにイソプロピルエーテル72.5gを用いたほかは実施例1と同様の方法にてヘキサフルオロアセトン一水和物を製造した。反応終了後に、比重 1.00の無色透明溶液127gを得た(収率100%)。
ガラス製還流蒸留塔、20cmの蒸留カラム(空塔)を備えた100mLナス型フラスコにHFA・3W 22g(0.1モル)、ベンゼン38g(0.49モル)を入れ、攪拌子にて攪拌しながらオイルバスにて加熱した。69℃-71℃で水/ベンゼンの共沸組成物(凝縮時に白濁した。)が留出し、塔頂の留出温度が73℃に上昇した時点で蒸留を一旦停止した。留出した液は2層に分離し、上層にベンゼン層、下層に水層が形成された(ベンゼン層:6.8g、比重0.87、水層:3.6g、比重1.15)。水層の比重が1より大きいことから若干のHFA成分が混入したことが示唆された。さらに蒸留を継続すると、73.8℃-74.0℃で新たな共沸組成物が留出した。留出した40gの均一、無色透明な比重1.04の液は、NMR(13C、H、F)、およびFR-IR測定によりベンゼン中でヘキサフルオロアセトン一水和物(1,1,1,3,3,3-ヘキサフルオロプロパン-2-ジオール)のみが存在すること、またカールフィッシャ水分測定装置で水分を測定し、HFAと水の比が1:1であること、また共沸組成はHFA・W39質量%のベンゼン溶液であることが判明した。また、釜残4.6gの均一、無色透明な比重1.37の液はHFA・W44質量%のベンゼン溶液であることが、NMR(13C、H、F)、FT-IR、カールフィッシャ水分測定で確認された。本脱水法によるヘキサフルオロアセトン一水和物の収率は96%であった。
ベンゼンの代わりにメタキシレン54gを用いたほかは実施例3と同様の脱水法にてヘキサフルオロアセトン一水和物を製造した。メタキシレンと水との最低共沸温度である94℃にて共沸組成物の留出がはじまり、凝縮すると白濁する液の留出が留出温度97℃まで続いた。留出した液は2層に分離し、上層にメタキシレン層、下層に水層が形成された(メタキシレン層:1.2g、比重0.86、水層:7.4g、比重1.37)。水層の比重が1よりかなり大きいことからHFA成分が混入したことが示唆された。釜残67.4gの均一、無色透明な比重1.03の液はHFA・W29.9質量%のメタキシレン溶液であって、NMR(13C、H、F)、およびFR-IR測定によりメタキシレン中でヘキサフルオロアセトン一水和物(1,1,1,3,3,3-ヘキサフルオロプロパン-2-ジオール)のみが存在すること、またカールフィッシャ水分測定装置で水分を測定し、HFAと水の比が1:1であることが確認された。本脱水法によるヘキサフルオロアセトン一水和物の収率は70.4%であった。
Claims (12)
- ヘキサフルオロアセトン水和物と有機溶媒をあらかじめ混合してまたは別々に蒸留塔に導入し、低沸点成分として塔頂から有機溶媒と水を含む組成物を得、塔底から高沸点成分としてヘキサフルオロアセトン一水和物および有機溶媒を含む組成物を得ることからなるヘキサフルオロアセトン一水和物の製造方法。
- ヘキサフルオロアセトン水和物と有機溶媒のうちの少なくともいずれかを連続的に蒸留塔に導入することからなる請求項1に記載のヘキサフルオロアセトン一水和物の製造方法。
- 塔底または塔頂から得られる組成物のうち少なくともいずれかを連続的に蒸留塔から取り出すことからなる請求項1または2に記載のヘキサフルオロアセトン一水和物の製造方法。
- ヘキサフルオロアセトン水和物がヘキサフルオロアセトン三水和物(HFA・3W)である請求項1~3のいずれか1項に記載のヘキサフルオロアセトン一水和物の製造方法。
- 塔底から得られるヘキサフルオロアセトン一水和物および有機溶媒を含む組成物から、ヘキサフルオロアセトン一水和物と有機溶媒の共沸組成物を取得する請求項1に記載のヘキサフルオロアセトン一水和物の製造方法。
- 水またはヘキサフルオロアセトン水和物が有機溶媒と共存する溶液系へ、系中に存在する水とヘキサフルオロアセトン水和物の合計モル数と等しいモル数のヘキサフルオロアセトンを導入し、ヘキサフルオロアセトン一水和物および有機溶媒を含む組成物として得ることからなるヘキサフルオロアセトン一水和物の製造方法。
- 有機溶媒が、芳香族化合物またはエーテル化合物である請求項1~6のいずれか1項に記載のヘキサフルオロアセトン一水和物の製造方法。
- ヘキサフルオロアセトン一水和物を反応基質とする反応系において、反応系の温度を高めて有機溶媒と水を共沸組成物として反応系から過剰の水を除去することからなるヘキサフルオロアセトン一水和物を反応基質とするヘキサフルオロアセトン誘導体の製造方法。
- ヘキサフルオロアセトン一水和物の反応により発生する過剰の水を有機溶媒と水の共沸組成物として反応系から除去しながら反応を行うヘキサフルオロアセトン誘導体の製造方法。
- 有機溶媒が、芳香族化合物またはエーテル化合物である請求項8または9に記載のヘキサフルオロアセトン誘導体の製造方法。
- ヘキサフルオロアセトン一水和物と有機溶媒からなる実質的に水を含まない組成物。
- 有機溶媒が、芳香族化合物またはエーテル化合物である請求項11に記載の組成物。
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CN201080036656.9A CN102471203B (zh) | 2009-08-18 | 2010-07-30 | 六氟丙酮一水合物的制造方法 |
US13/384,736 US20120136177A1 (en) | 2009-08-18 | 2010-07-30 | Process for Preparation of Hexafluoroacetone Monohydrate |
EP10809836.9A EP2468710B1 (en) | 2009-08-18 | 2010-07-30 | Process for preparation of hexafluoroacetone monohydrate |
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JP2009189347A JP5482013B2 (ja) | 2009-08-18 | 2009-08-18 | ヘキサフルオロアセトン一水和物の製造方法 |
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EP (1) | EP2468710B1 (ja) |
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WO2012020701A1 (ja) * | 2010-08-12 | 2012-02-16 | セントラル硝子株式会社 | ヘキサフルオロアセトン一水和物の製造方法 |
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CN106699504A (zh) * | 2015-11-18 | 2017-05-24 | 浙江蓝天环保高科技股份有限公司 | 一种2,2-双(3,4-二甲苯基)六氟丙烷的制备方法 |
CN106699509A (zh) * | 2015-11-18 | 2017-05-24 | 浙江蓝天环保高科技股份有限公司 | 一种2-(3,4-二甲苯基)-1,1,1,3,3,3-六氟-2-丙醇的制备方法 |
US11344761B2 (en) | 2018-10-15 | 2022-05-31 | Honeywell International Inc. | Azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF3I) and 1,1,1,2,2,3,3,-heptafluoropropane (HFC-227ca) |
US11318338B2 (en) | 2018-10-15 | 2022-05-03 | Honeywell International Inc. | Azeotrope or azeotrope-like compositions of trifluoroidomethane (CF3I) and 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) |
US10662135B2 (en) * | 2018-10-15 | 2020-05-26 | Honeywell International Inc. | Azeotrope or azeotrope-like compositions of trifluoroiodomethane (CF3I) and hexafluoroacetone (HFA) |
CN111018683B (zh) * | 2019-12-19 | 2024-04-02 | 天津市长芦化工新材料有限公司 | 六氟丙酮水合物的制备装置 |
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- 2009-08-18 JP JP2009189347A patent/JP5482013B2/ja not_active Expired - Fee Related
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- 2010-07-30 EP EP10809836.9A patent/EP2468710B1/en not_active Not-in-force
- 2010-07-30 CN CN201080036656.9A patent/CN102471203B/zh not_active Expired - Fee Related
- 2010-07-30 WO PCT/JP2010/062878 patent/WO2011021491A1/ja active Application Filing
- 2010-07-30 US US13/384,736 patent/US20120136177A1/en not_active Abandoned
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WO2012020701A1 (ja) * | 2010-08-12 | 2012-02-16 | セントラル硝子株式会社 | ヘキサフルオロアセトン一水和物の製造方法 |
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JP2011037804A (ja) | 2011-02-24 |
CN102471203A (zh) | 2012-05-23 |
EP2468710A1 (en) | 2012-06-27 |
CN102471203B (zh) | 2014-08-06 |
US20120136177A1 (en) | 2012-05-31 |
EP2468710B1 (en) | 2017-03-01 |
JP5482013B2 (ja) | 2014-04-23 |
EP2468710A4 (en) | 2013-01-23 |
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