JPS6335537A - Production of hexafluoroacetone hydrate - Google Patents
Production of hexafluoroacetone hydrateInfo
- Publication number
- JPS6335537A JPS6335537A JP61181096A JP18109686A JPS6335537A JP S6335537 A JPS6335537 A JP S6335537A JP 61181096 A JP61181096 A JP 61181096A JP 18109686 A JP18109686 A JP 18109686A JP S6335537 A JPS6335537 A JP S6335537A
- Authority
- JP
- Japan
- Prior art keywords
- salt
- hexafluoro
- water
- aqueous solution
- nickel
- Prior art date
- Legal status (The legal status 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 status listed.)
- Granted
Links
- HEBNOKIGWWEWCN-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-one;hydrate Chemical compound O.FC(F)(F)C(=O)C(F)(F)F HEBNOKIGWWEWCN-UHFFFAOYSA-N 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- CMQUGOHGJUTDGZ-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(O)(C(F)(F)F)C(F)(F)F CMQUGOHGJUTDGZ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 150000002815 nickel Chemical class 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 229910052751 metal Inorganic materials 0.000 claims description 6
- 239000002184 metal Substances 0.000 claims description 6
- -1 nickel chloride Chemical class 0.000 abstract description 5
- 239000002904 solvent Substances 0.000 abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 abstract description 4
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 abstract description 4
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 4
- 239000007789 gas Substances 0.000 abstract description 3
- 239000003905 agrochemical Substances 0.000 abstract description 2
- ZFVMWEVVKGLCIJ-UHFFFAOYSA-N bisphenol AF Chemical compound C1=CC(O)=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=C(O)C=C1 ZFVMWEVVKGLCIJ-UHFFFAOYSA-N 0.000 abstract description 2
- 239000003431 cross linking reagent Substances 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 229920003051 synthetic elastomer Polymers 0.000 abstract description 2
- 229920003002 synthetic resin Polymers 0.000 abstract description 2
- 239000000057 synthetic resin Substances 0.000 abstract description 2
- 239000005061 synthetic rubber Substances 0.000 abstract description 2
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical compound FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- MSWVMWGCNZQPIA-UHFFFAOYSA-N 1-fluoropropan-2-one Chemical compound CC(=O)CF MSWVMWGCNZQPIA-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 2
- 239000010931 gold Substances 0.000 description 2
- 229910052737 gold Inorganic materials 0.000 description 2
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 2
- 238000010813 internal standard method Methods 0.000 description 2
- 229940078494 nickel acetate Drugs 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DOJXGHGHTWFZHK-UHFFFAOYSA-N Hexachloroacetone Chemical compound ClC(Cl)(Cl)C(=O)C(Cl)(Cl)Cl DOJXGHGHTWFZHK-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- LGQLOGILCSXPEA-UHFFFAOYSA-L nickel sulfate Chemical compound [Ni+2].[O-]S([O-])(=O)=O LGQLOGILCSXPEA-UHFFFAOYSA-L 0.000 description 1
- 229910000363 nickel(II) sulfate Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- RLMIGULSVHMDCM-UHFFFAOYSA-M potassium;3,3,3-trifluoro-2-hydroxy-2-(trifluoromethyl)propanoate Chemical compound [K+].[O-]C(=O)C(O)(C(F)(F)F)C(F)(F)F RLMIGULSVHMDCM-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ヘキサフルオロアセトン水和物の製造法に関
する。更に詳しくは、ヘキサフルオロ−α−ヒドロキシ
イソブタン酸塩からヘキサフルオロアセ１ヘン水和物を
製造する方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing hexafluoroacetone hydrate. More specifically, the present invention relates to a method for producing hexafluoroacethenene hydrate from hexafluoro-α-hydroxyisobutanoate.
／＼キサフルオロアセトンは、合成樹脂、合成ゴムなど
の製造用単量体として、あるいはビスフェノールＡＦな
どの架橋剤の中間体、医薬、農薬などの中間原料などと
して用いられる。/\xafluoroacetone is used as a monomer for manufacturing synthetic resins, synthetic rubbers, etc., as an intermediate for crosslinking agents such as bisphenol AF, and as an intermediate raw material for pharmaceuticals, agricultural chemicals, etc.
このような各種の用途を有するヘキサフルオロアセトン
は、従来法のような方法によってＩ２造することが提案
されている。Hexafluoroacetone, which has such various uses, has been proposed to be produced by conventional methods.
Ｃａｎ、 Ｊ、 Ｃｈｅ＋ｎ、第３３巻第４５３頁（１
！１１５５）米国特許筒３，３２１，５１５号明細書米
国特許第４，３３７，３６１号明細書しかしながら、上
記の各方法には、次のような欠点がみられる。Can, J, Che+n, vol. 33, p. 453 (1
! 1155) US Pat. No. 3,321,515 US Pat. No. 4,337,361 However, each of the above methods has the following drawbacks.
（１）過マンガン酸カリウムによる酸化反応は。(1) What is the oxidation reaction with potassium permanganate?
反応が激しくまた副生ずる二酸化マンガンが容易には処
置てきない産業廃棄物となること（２）へキサフルオロ
プロペンより合成されるそのオキサイドは高純度のもの
が得られ鷺く、従って生成物たるヘキサフルオロアセト
ン中にヘキサフルオロプロペンなどが混在すること
（３）ジチエタンの硝酸酸化では、得られるヘキサフル
オロアセトン水和物中にＮＯ□およびＳＯ２が含まれ、
それの除去に手間がかかること
（４）へキサクロルアセトンの使用は、合成上塩素が重
量を増加させるだけで効率的ではなく、また有毒な五塩
化アンチモンを必要とし、更に高純度の生成物が得られ
難いこと
〔発明が解決しようとする問題点〕
本発明者らは、かかる欠点がみられるこれらの従来技術
とは全く発想を異にし、それの有効利用が強く求められ
ているオクタフルオロイソブチンまたはそのアルコール
付加物を原料物質として用い、それを一旦ヘキサフルオ
ローα−ヒドロキシイソブタン酸塩に変換させた後ハロ
ゲンと反応させることにより、目的とするヘキサフルオ
ロアセトン水和物が得られることを見出した。(2) The oxide synthesized from hexafluoropropene is highly pure, and therefore the product hexafluoropropene is highly purified. Hexafluoropropene etc. are mixed in fluoroacetone (3) In nitric acid oxidation of dithiethane, NO□ and SO2 are contained in the obtained hexafluoroacetone hydrate,
(4) The use of hexachloroacetone is not efficient because chlorine only increases the weight of the synthesis, and it requires toxic antimony pentachloride, which also requires a high purity product. [Problem to be Solved by the Invention] The present inventors have developed an octafluorocarbon solution, which is completely different from the conventional techniques that have such drawbacks, and whose effective use is strongly desired. The desired hexafluoroacetone hydrate can be obtained by using isobutyne or its alcohol adduct as a raw material, converting it into hexafluoro α-hydroxyisobutanoate, and then reacting it with a halogen. I found out.
得られたヘキサフルオロアセトン水和物は、それ自体ポ
リエステル、ポリアミドなどの溶媒として使用できるが
、それの脱水を行う場合には、五酸化リン１３ｍ硫酸、
無水硫酸あるいはモレキュラシーブなどを用いる方法に
よって行うことができるので（特開昭５７−８１，４３
３号公報、同５９−１５７，０４５号公報）１本発明方
法はへキサフルオロアセ１〜ンの製造にも通ずるもので
ある。The obtained hexafluoroacetone hydrate itself can be used as a solvent for polyester, polyamide, etc., but when dehydrating it, phosphorus pentoxide 13m sulfuric acid,
This can be done by a method using anhydrous sulfuric acid or molecular sieves (Japanese Unexamined Patent Publication No. 57-81, 43).
(No. 3, No. 59-157,045) The method of the present invention is also applicable to the production of hexafluoroacetone.
従って５本発明はへキサフルオロアセトン水和物の製造
法に係り、ヘキサフルオロアセトン水和物の製造は、ヘ
キサフルオロ−α−ヒドロキシイソブタン酸の水溶性金
属塩を水溶液の状態でニッケル塩の存在下にハロゲンガ
スと反応させることにより行われる。Therefore, the present invention relates to a method for producing hexafluoroacetone hydrate, in which a water-soluble metal salt of hexafluoro-α-hydroxyisobutanoic acid is added in an aqueous solution in the presence of a nickel salt. This is done by reacting with halogen gas.
ヘキサフルオロ−α−ヒドロキシイソブタン酸（３゜３
．３− トリフルオロ−２−ヒドロキシ−２−トリフル
オロメチル−２−トリフルオロメチルプロピオン酸）（
ＣＦ、 ）２Ｃ（Ｏｌｌ）Ｃｏｏ）ｌは、例えばオクタ
フルオロイソブチンのアルコール付加物をアルカリ性過
酸化水素で酸化し、その後溶媒中で加水分解することに
より合成される（特願昭６０−１２５，２４２号）。Hexafluoro-α-hydroxyisobutanoic acid (3゜3
．． 3-trifluoro-2-hydroxy-2-trifluoromethyl-2-trifluoromethylpropionic acid) (
CF, )2C(Oll)Coo)l is synthesized, for example, by oxidizing an alcohol adduct of octafluoroisobutyne with alkaline hydrogen peroxide and then hydrolyzing it in a solvent (Japanese Patent Application No. 60-125, No. 242).
このヘキサフルオロ−α−ヒドロキシイソブタン酸は、
水溶性金属塩、具体的にはナトリウム塩。This hexafluoro-α-hydroxyisobutanoic acid is
Water-soluble metal salts, specifically sodium salts.
カリウム塩などのアルカリ金属塩あるいはカルシウム塩
などのアルカリ土類金属塩として本発明方法に用いられ
る。これらの金属塩は、一般に上記加水分解に用いられ
る金属化合物によって形成され、また必要に応じてこの
反応液を酸性とた後蒸留により酸を分離し、目的金属の
水酸化物または炭酸塩の水溶液で中和させることにより
形成させる。It is used in the method of the present invention as an alkali metal salt such as a potassium salt or an alkaline earth metal salt such as a calcium salt. These metal salts are generally formed from the metal compounds used in the above-mentioned hydrolysis, and if necessary, the reaction solution is made acidic and then the acid is separated by distillation to form an aqueous solution of the hydroxide or carbonate of the target metal. Formed by neutralization with
反応は、水溶性金属塩を約１０〜５０％の濃度となる水
溶液に調製した後、金冠塩に対して約０．０１〜１．０
モル当量、好ましくは約０．１〜０．３モル当量のニッ
ケル塩１例えば塩化ニッケル、酢酸ニッケル、硫酸ニッ
ケルなどを加え、そこに金冠塩に対して約０．５〜５モ
ル当量、好ましくは約１〜２モル当量の塩素ガスまたは
臭素ガスを、室温〜約８０℃、好ましくは約３０〜６０
℃の温度で通すことにより行われる。In the reaction, the water-soluble metal salt is prepared into an aqueous solution with a concentration of about 10-50%, and then the concentration is about 0.01-1.0% with respect to the gold crown salt.
Add molar equivalents, preferably about 0.1 to 0.3 molar equivalents of nickel salt 1, such as nickel chloride, nickel acetate, nickel sulfate, etc., and add thereto about 0.5 to 5 molar equivalents, preferably about 0.5 to 5 molar equivalents relative to the gold crown salt. About 1 to 2 molar equivalents of chlorine gas or bromine gas are added at room temperature to about 80°C, preferably about 30 to 60°C.
It is carried out by passing at a temperature of °C.
このような条件下で反応が行われた後、反応生成物たる
ヘキサフルオロアセ１−ン水和物は、水に不溶性のエー
テル系溶媒、例えばジエチルエーテル、ジインプロピル
エーテルなどによって反応混合物中から抽出され、抽出
溶媒を留去することによって目的物として取得される。After the reaction is carried out under these conditions, the reaction product, hexafluoroacetate hydrate, is extracted from the reaction mixture with a water-insoluble ether solvent, such as diethyl ether or diimpropyl ether. The target product is obtained by distilling off the extraction solvent.
次に、実施例について本発明を説明する。 Next, the present invention will be explained with reference to examples.
実施例１
冷却器、撹拌装置および温度計を備えた容量ＬＯＯｍ
Ｑのフラスコに、ヘキサフルオロ−α−ヒドロキシイソ
ブタン酸カリウム８．３ｇ（３３ミリモル）、水４０ｇ
および塩化ニッケル・６Ｈ，０１，Ｏｇ（４ミリモル）
を仕込み、フラスコ浴を６０℃に加熱しながら、そこに
塩素ガス：３．５．（４９ミリモル）を１時間の間に通
じた。Example 1 Capacity LOOm with cooler, stirrer and thermometer
In flask Q, 8.3 g (33 mmol) of potassium hexafluoro-α-hydroxyisobutanoate and 40 g of water.
and nickel chloride 6H,01,Og (4 mmol)
While heating the flask bath to 60°C, add chlorine gas: 3.5. (49 mmol) was passed over the course of 1 hour.
この反応について、Ｆｎｍｒ内標法によりヘキサフルオ
ロアセトン水和物の生成量を測定すると１．１ｇ（収率
４４％）の値が得られた。Regarding this reaction, when the amount of hexafluoroacetone hydrate produced was measured using the Fnmr internal standard method, a value of 1.1 g (yield 44%) was obtained.
実施例２
実施例１において、塩化ニッケル・６］１□０の代りに
酢酸ニッケル・４Ｈ２０を用いた。Example 2 In Example 1, nickel acetate 4H20 was used instead of nickel chloride 6]1□0.
Ｆｎｍｒ内標法によるヘキサフルオロアセトン水和物の
生成量は１．０ｇ（収率４２％）であった。The amount of hexafluoroacetone hydrate produced by the Fnmr internal standard method was 1.0 g (yield 42%).
比較例
実施例１において、ニッケル塩を用いないと、反応は殆
んど進行しなかった。Comparative Example In Example 1, the reaction hardly proceeded unless a nickel salt was used.
Claims (1)
溶性金属塩を、水溶液の状態でニッケル塩の存在下にハ
ロゲンガスと反応させることを特徴とするヘキサフルオ
ロアセトン水和物の製造法。1. A method for producing hexafluoroacetone hydrate, which comprises reacting a water-soluble metal salt of hexafluoro-α-hydroxyisobutanoic acid with a halogen gas in the presence of a nickel salt in an aqueous solution state.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61181096A JPH0699348B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroacetone hydrate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61181096A JPH0699348B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroacetone hydrate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6335537A true JPS6335537A (en) | 1988-02-16 |
| JPH0699348B2 JPH0699348B2 (en) | 1994-12-07 |
Family
ID=16094761
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61181096A Expired - Fee Related JPH0699348B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroacetone hydrate |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0699348B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005102972A1 (en) * | 2004-04-19 | 2005-11-03 | Daikin Industries, Ltd. | Method for producing hydrate of fluoroalkyl ketone |
-
1986
- 1986-07-31 JP JP61181096A patent/JPH0699348B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005102972A1 (en) * | 2004-04-19 | 2005-11-03 | Daikin Industries, Ltd. | Method for producing hydrate of fluoroalkyl ketone |
| US7598425B2 (en) | 2004-04-19 | 2009-10-06 | Daikin Industries, Ltd. | Method for producing hydrate of fluoroalkyl ketone |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0699348B2 (en) | 1994-12-07 |
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