JPS6411624B2 - - Google Patents
Info
- Publication number
- JPS6411624B2 JPS6411624B2 JP12032285A JP12032285A JPS6411624B2 JP S6411624 B2 JPS6411624 B2 JP S6411624B2 JP 12032285 A JP12032285 A JP 12032285A JP 12032285 A JP12032285 A JP 12032285A JP S6411624 B2 JPS6411624 B2 JP S6411624B2
- Authority
- JP
- Japan
- Prior art keywords
- hexafluoroacetone
- heptafluoroisobutenyl
- reaction
- ether
- hydrate
- 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.)
- Expired
Links
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 12
- -1 heptafluoroisobutenyl alkyl ether Chemical class 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- LCRBBUPAHHPMMY-UHFFFAOYSA-N 1,3,3,3-tetrafluoro-1-[1,3,3,3-tetrafluoro-2-(trifluoromethyl)prop-1-enoxy]-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(F)OC(F)=C(C(F)(F)F)C(F)(F)F LCRBBUPAHHPMMY-UHFFFAOYSA-N 0.000 description 7
- 239000002994 raw material Substances 0.000 description 6
- 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 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical compound FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 4
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 3
- 238000010813 internal standard method Methods 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 239000003444 phase transfer catalyst Substances 0.000 description 2
- 239000010453 quartz Substances 0.000 description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 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
- 231100000331 toxic Toxicity 0.000 description 2
- 230000002588 toxic effect Effects 0.000 description 2
- 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
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-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
- 239000003905 agrochemical Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide 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
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 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 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000002440 industrial waste Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 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
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
Landscapes
- Physical Or Chemical Processes And Apparatus (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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の製造法に
関する。更に詳しくは、オクタフルオロイソブテ
ンまたはそのアルコール付加物の有効利用をも兼
ねたヘキサフルオロアセトンの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing hexafluoroacetone. More specifically, the present invention relates to a method for producing hexafluoroacetone that also effectively utilizes octafluoroisobutene or its alcohol adduct.
ヘ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は、あるいはビスフ
エノール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ている。
Hexafluoroacetone is used as a monomer for the production of synthetic resins and synthetic rubbers, as an intermediate for crosslinking agents such as bisphenol AF, and as an intermediate raw material for pharmaceuticals, agricultural chemicals, and the like.
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、従来次のような方法によつて製造す
ることが提案されている。 Hexafluoroacetone, which has such various uses, has been conventionally proposed to be produced by the following method.
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。 However, each of the above methods has the following drawbacks.
(1) 過マンガン酸カリによる酸化反応は、反応が
激しくまた副生する二酸化マンガンが容易には
処置できない産業廃棄物となること
(2) ヘ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難く、従つ
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NO2およびSO2が
含まれ、それの除去に手間がかかること
(4) ヘ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テン
またはそのアルコール付加物を原料物質として用
い、それを酸化することにより、目的とするヘキ
サフルオロアセトンを得ることに成功した。(1) The oxidation reaction with potassium permanganate is violent, and the by-product, manganese dioxide, becomes industrial waste that cannot be easily disposed of. (2) The oxide synthesized from hexafluoropropene is of high purity. Therefore, hexafluoropropene etc. are mixed in the hexafluoroacetone product (3) In the nitric acid oxidation of dithiethane, the resulting hexafluoroacetone hydrate contains NO 2 and SO 2 . (4) The use of hexachloroacetone is not efficient as chlorine only increases the weight of the synthesis, it also requires toxic antimony pentachloride, and it 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. By using isobutene or its alcohol adduct as a raw material and oxidizing it, we succeeded in obtaining the desired hexafluoroacetone.
〔問題点を解決するための手段〕および〔作用〕
従つて、本発明はヘキサフルオロアセトンの製
造法に係り、ヘキサフルオロアセトンの製造は、
ヘプタフルオロイソブテニルアルキルエーテルを
光照射下に酸素と反応させることにより行われ
る。[Means for Solving the Problems] and [Operation] Therefore, the present invention relates to a method for producing hexafluoroacetone, and the production of hexafluoroacetone includes:
It is carried out by reacting heptafluoroisobutenyl alkyl ether with oxygen under irradiation with light.
オクタフルオロイソブテンは、含フツ素共重合
体の重要な原料の一種であるヘキサフルオロプロ
ペンの製造時の副生成物であり、この毒性の強い
オクタフルオロイソブテンは、一般に低級アルコ
ール、例えばメタノール、ｎ−プロパノール、イ
ソプロパノール、ｎ−ブタノールなどとのアルコ
ール付加物を容易に形成する性質を有している。 Octafluoroisobutene is a by-product during the production of hexafluoropropene, which is an important raw material for fluorine-containing copolymers.This highly toxic octafluoroisobutene is generally used in lower alcohols such as methanol, n- It has the property of easily forming alcohol adducts with propanol, isopropanol, n-butanol, etc.
このアルコール付加物たるオクタフルオロイソ
ブテンアルキルエーテルは、第４級アンモニウム
塩などの相関移動触媒の存在下に、アルカリ金属
またはアルカリ土類金属の水酸化物または炭酸塩
あるいはトリアルキルアミンなどの塩基と共に撹
拌することにより脱フツ化水素反応され、ヘプタ
フルオロイソブテニルアルキルエーテルを与え
る。 The alcohol adduct, octafluoroisobutene alkyl ether, is stirred with an alkali metal or alkaline earth metal hydroxide or carbonate or a base such as a trialkylamine in the presence of a phase transfer catalyst such as a quaternary ammonium salt. The dehydrofluorination reaction is performed to give heptafluoroisobutenyl alkyl ether.
かかるヘプタフルオロイソブテニルアルキルエ
ーテルは、光照射下に酸素と反応させると、次式
に示されるようにヘキサフルオロアセトンの水和
物を与える。 When such heptafluoroisobutenyl alkyl ether is reacted with oxygen under light irradiation, it gives a hydrate of hexafluoroacetone as shown in the following formula.
この反応は、石英製の反応容器などを用い、そ
こにヘキサフルオロイソブテニルアルキルエーテ
ルを加え、好ましくは水の存在下で、激しく撹拌
しながら酸素をバルブリングさせ、水銀ランプな
どで紫外線などを照射することによつて行われ
る。 This reaction uses a quartz reaction vessel, etc., adds hexafluoroisobutenyl alkyl ether, preferably in the presence of water, bubbles oxygen while stirring vigorously, and then irradiates with ultraviolet rays using a mercury lamp or the like. This is done by irradiation.
照射光源としては、例えば波長約100〜600n
ｍ、好ましくは約150〜400nｍの紫外線が用いら
れ、酸素はヘキサフルオロイソブテニルアルキル
エーテルに対して約２〜20、好ましくは約４〜10
のモル比で供給され、この反応温度としては一般
に−50〜100℃、好ましくは−10〜60℃の温度が
用いられる。 As an irradiation light source, for example, the wavelength is about 100 to 600n.
m, preferably about 150 to 400 nm, and oxygen is about 2 to 20, preferably about 4 to 10 m, relative to hexafluoroisobutenyl alkyl ether.
The reaction temperature is generally -50 to 100°C, preferably -10 to 60°C.
この反応の際、水を添加すると、ヘキサフルオ
ロアセトンへの転化率は低いものの選択率が良好
なため、水の不存在下での反応と結局はほぼ同じ
収率で目的物を得ることができ、しかも回収され
た原料はくり返して使用することができる。 When water is added during this reaction, the conversion rate to hexafluoroacetone is low, but the selectivity is good, so the desired product can be obtained in almost the same yield as the reaction in the absence of water. Moreover, the recovered raw materials can be used repeatedly.
得られたヘキサフルオロアセトンは水和物の形
をとつており、水和物自体ポリエステル、ポリア
ミドなどの溶媒として使用できるが、それの脱水
を行なう場合には、五酸化リン、濃硫酸、無水硫
酸あるいはモレキユラシーブなどを用いる方法に
よつて容易に行なうことができる（特開昭57−
81433号公報、同59−157045号公報）。 The obtained hexafluoroacetone is in the form of a hydrate, and the hydrate itself can be used as a solvent for polyester, polyamide, etc., but when dehydrating it, phosphorus pentoxide, concentrated sulfuric acid, sulfuric anhydride, etc. Alternatively, it can be easily carried out by a method using a molecular sieve etc.
Publication No. 81433, Publication No. 59-157045).
ヘキサフルオロアセトンが、ヘプタフルオロイ
ソブテニルアルキルエーテルの酸化という全くの
新規な反応方法により得ることができ、これはオ
クタフルオロイソブテンまたはそのアルコール付
加物の有効利用としても有意義である。
Hexafluoroacetone can be obtained by a completely new reaction method of oxidation of heptafluoroisobutenyl alkyl ether, which is also significant as an effective use of octafluoroisobutene or its alcohol adduct.
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
球入り冷却管およびガス導入管を備えた容量
300mlの石英製円筒状容器に、ヘプタフルオロイ
ソブテニルエーテル15ｇ（0.07モル）、水10ｇ
（0.55モル）、光増感剤としてのローズベンガル
0.035ｇ（3.4×10-5モル）および第４級アンモニ
ウム塩（ローズベンガルがヘプタフルオロイソブ
テニルエーテルに不溶、水に可溶であるため、こ
れら不均一系２成分間の相間移動触媒として使
用）少量をそれぞれ仕込み、スターラーで激しく
撹拌しながら、酸素を40時間の間に約30バブリ
ングさせた。この間、50℃で500Wの中圧水銀ラ
ンプを照射し続けた。照射終了後、反応容器内の
反応混合物は２層に分離していたので、それらを
分液した。Example 1 Capacity with bulb cooling tube and gas introduction tube
In a 300 ml cylindrical quartz container, 15 g (0.07 mol) of heptafluoroisobutenyl ether and 10 g of water.
(0.55 mol), Rose Bengal as photosensitizer
0.035 g (3.4 × 10 -5 mol) and a quaternary ammonium salt (Rose Bengal is insoluble in heptafluoroisobutenyl ether and soluble in water, so it is used as a phase transfer catalyst between these two heterogeneous components. ) A small amount of each was added, and while vigorously stirring with a stirrer, oxygen was bubbled approximately 30 times during 40 hours. During this time, irradiation was continued with a 500 W medium pressure mercury lamp at 50°C. After the irradiation was completed, the reaction mixture in the reaction vessel was separated into two layers, which were separated.
その結果、上層にはヘキサフルオロアセトン水
和物の19重量％水溶液（Ｆ−NMR内標法によ
る）が13.0ｇ得られ、下層には未反応ヘプタフル
オロイソブテニルエーテル（Ｆ−NMRによる）
が9.7ｇ回収され、またドライアイス・メタノー
ルトラツプにはヘプタフルオロイソブテニルエー
テル66重量％−オクタフルオロイソブチルエーテ
ル33重量％混合物（Ｆ−NMR内標法による）が
0.8ｇ得られた。 As a result, 13.0 g of a 19% by weight aqueous solution of hexafluoroacetone hydrate (by F-NMR internal standard method) was obtained in the upper layer, and unreacted heptafluoroisobutenyl ether (by F-NMR) was obtained in the lower layer.
A mixture of 66% by weight heptafluoroisobutenyl ether and 33% by weight octafluoroisobutyl ether (according to the F-NMR internal standard method) was recovered in the dry ice/methanol trap.
0.8g was obtained.
回収原料量 9.7＋0.8×0.66＝10.2ｇ
全転化率 15.0−10.2／15.0×100＝32％
収 率 13.0×0.192／184／15.0／212×100＝19.2％
ただし、
184：ヘキサフルオロアセトン水和物の分子量
212：ヘプタフルオロイソブテニルエーテルの分
子量
選択率 19.2／32.0×100＝60％
実施例 ２
実施例１において、ヘプタフルオロイソブテニ
ルエーテル30.5ｇ（0.14モル）を用い、水の不存
在下に、酸素を48時間の間に約20バブリングさ
せた。Amount of recovered raw material 9.7 + 0.8 x 0.66 = 10.2 g Total conversion rate 15.0 - 10.2 / 15.0 x 100 = 32% Yield 13.0 x 0.192 / 184 / 15.0 / 212 x 100 = 19.2% However, 184: Hexafluoroacetone hydrate Molecular weight of substance 212: Molecular weight selectivity of heptafluoroisobutenyl ether 19.2/32.0×100=60% Example 2 In Example 1, 30.5 g (0.14 mol) of heptafluoroisobutenyl ether was used, and the absence of water Below, oxygen was bubbled approximately 20 times during 48 hours.
その結果、反応容器内の反応液として、ヘキサ
フルオロアセトン水和物29重量％および副反応物
を含有する水溶液が17.7ｇ得られ、またドライア
イス・メタノールトラツプにはヘプタフルオロイ
ソブテニルエーテル15重量％−オクタフルオロイ
ソブチルエーテル85重量％混合物（Ｆ−NMR内
標法による）が10.0ｇ得られた。 As a result, 17.7 g of an aqueous solution containing 29% by weight of hexafluoroacetone hydrate and side reactants was obtained as the reaction liquid in the reaction vessel, and 15 g of heptafluoroisobutenyl ether was placed in the dry ice/methanol trap. 10.0 g of a mixture of 85% by weight octafluoroisobutyl ether (according to F-NMR internal standard method) was obtained.
回収原料量 10.0×0.15＝1.5ｇ 全転化率 30.5−1.5／30.5×100＝95％ 収 率 17.7×0.29／184／30.5／212×100＝19.4％ 選択率 19.4／95.0×100＝20.4％Amount of recovered raw materials 10.0×0.15=1.5g Total conversion rate 30.5−1.5/30.5×100=95% Yield 17.7×0.29/184/30.5/212×100=19.4% Selection rate 19.4/95.0×100=20.4%
Claims (1)
ルを光照射下に酸素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の製造法。 ２ 水の存在下で反応させる特許請求の範囲第１
項記載のヘキサフルオロアセトンの製造法。 ３ ヘキサフルオロアセトンが水和物として得ら
れる特許請求の範囲第１項または第２項記載のヘ
キサフルオロアセトンの製造法。[Claims] 1. A method for producing hexafluoroacetone, which comprises reacting heptafluoroisobutenyl alkyl ether with oxygen under irradiation with light. 2 Claim 1 where the reaction is carried out in the presence of water
The method for producing hexafluoroacetone described in Section 1. 3. The method for producing hexafluoroacetone according to claim 1 or 2, wherein hexafluoroacetone is obtained as a hydrate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12032285A JPS61277645A (en) | 1985-06-03 | 1985-06-03 | Production of hexafluoroacetone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12032285A JPS61277645A (en) | 1985-06-03 | 1985-06-03 | Production of hexafluoroacetone |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61277645A JPS61277645A (en) | 1986-12-08 |
| JPS6411624B2 true JPS6411624B2 (en) | 1989-02-27 |
Family
ID=14783382
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12032285A Granted JPS61277645A (en) | 1985-06-03 | 1985-06-03 | Production of hexafluoroacetone |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS61277645A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4885398A (en) * | 1987-07-21 | 1989-12-05 | Nippon Mektron Limited | Process for producing hexafluoroacetone or its hydrate |
| JP4534274B2 (en) * | 1999-09-13 | 2010-09-01 | ユニマテック株式会社 | Method for producing hexafluoroacetone or hydrate thereof |
| US6274005B1 (en) * | 2000-05-26 | 2001-08-14 | Halocarbon Products Corporation | Method for the preparation of hexafluoroacetone |
| JP4396831B2 (en) | 2004-04-19 | 2010-01-13 | ダイキン工業株式会社 | Method for producing fluoroalkyl ketone hydrate |
| JP5315609B2 (en) | 2006-06-05 | 2013-10-16 | ダイキン工業株式会社 | Novel carboxylic acid compound, its use and production method |
| JP5114880B2 (en) | 2006-07-06 | 2013-01-09 | ダイキン工業株式会社 | Novel α-fluoromethoxycarboxylic acid ester, method for producing the α-fluoromethoxycarboxylic acid ester, and method for producing sevoflurane |
| JP5163064B2 (en) | 2007-11-13 | 2013-03-13 | ダイキン工業株式会社 | Novel carboxylic acid ester, its use and production method |
-
1985
- 1985-06-03 JP JP12032285A patent/JPS61277645A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61277645A (en) | 1986-12-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6212212B2 (en) | ||
| JPS6411624B2 (en) | ||
| JPH0579055B2 (en) | ||
| US4885398A (en) | Process for producing hexafluoroacetone or its hydrate | |
| US5919341A (en) | Difluorochloracetyl, dichloracetyl and trichloracetyl chloride preparation | |
| JPH085823B2 (en) | Method for producing hexafluoroacetone or its hydrate | |
| JP2514368B2 (en) | Method for producing hexafluoroacetone or its hydrate | |
| US5945562A (en) | Process of preparing perfluoroalkylcarboxylic acid | |
| JP3102151B2 (en) | Iodinated benzyldiphenyl and its preparation | |
| US4318866A (en) | Chlorination of 4-methoxybenzoyl chloride | |
| JPS61286348A (en) | Production of 3,3,3-trifluoro-2-hydroxy-2-trifluoromethylpropionic acid ester | |
| JPS6133A (en) | Production of methallyl alcohol | |
| JPH09169673A (en) | Production of 3,5-bis(trifluoromethyl)bromobenzene | |
| JPH0723332B2 (en) | Process for producing 1,3-dichloro-2-propanol | |
| JPS60100536A (en) | Preparation of 2-(p-isobutylphenyl)propionic acid | |
| JP3214065B2 (en) | Method for producing difluorobromoacetyl fluoride | |
| JPS61118333A (en) | Production of perfluoroallyl chloride | |
| JP4759177B2 (en) | Method for producing mevalolactone | |
| JPS62298546A (en) | Production of anisaldehyde | |
| KR900003509B1 (en) | Process for the preparation of pyrethroid ester compound | |
| JPH0699348B2 (en) | Method for producing hexafluoroacetone hydrate | |
| JPS63162641A (en) | Production of pentaerythritol allyl ether | |
| JP4248693B2 (en) | Process for producing 3-hydroxy-1-cycloalkene | |
| JPH08333298A (en) | Production of alpha-(trifluoromethyl)arylacetic acid | |
| JPS5829735A (en) | Preparation of enzaldehydes |