JP4534274B2 - Method for producing hexafluoroacetone or hydrate thereof - Google Patents
Method for producing hexafluoroacetone or hydrate thereof Download PDFInfo
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- JP4534274B2 JP4534274B2 JP25820499A JP25820499A JP4534274B2 JP 4534274 B2 JP4534274 B2 JP 4534274B2 JP 25820499 A JP25820499 A JP 25820499A JP 25820499 A JP25820499 A JP 25820499A JP 4534274 B2 JP4534274 B2 JP 4534274B2
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- hexafluoroacetone
- hydrate
- producing
- reaction tube
- thermal decomposition
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Description
【0001】
【産業上の利用分野】
本発明は、ヘキサフルオロアセトンまたはその水和物の製造法に関する。更に詳しくは、反応の副生成物であるパーフルオロ(2-メチル-1,2-エポキシプロピル)エーテルの有効利用を図るヘキサフルオロアセトンまたはその水和物の製造法に関する。
【0002】
【従来の技術】
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、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ている。
【0003】
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水和物は、従来次のような方法によって製造することが提案されている。
【0004】
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。
(1)過マンガン酸カリウムによる酸化反応は、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
(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
(3)ジチエタン(ヘキサフルオロチオアセトン2量体)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
(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
【0005】
【発明が解決しようとする課題】
本発明の目的は、ヘプタフルオロイソブテニルエーテルをオゾン酸化してヘキサフルオロアセトンを製造する際の副生成物であるパーフルオロ(2-メチル-1,2-エポキシプロピル)エーテルの有効利用法としてのヘキサフルオロアセトンまたはその水和物の製造法を提供することにある。
【0006】
【課題を解決するための手段】
かかる本発明の目的は、一般式
(ここでRは低級アルキル基、アリール基またはベンジル基である)で表わされるパーフルオロ(2-メチル-1,2-エポキシプロピル)エーテルを熱分解し、ヘキサフルオロアセトンまたはその水和物を製造することにより達成される。
【0007】
【発明の実施の形態】
出発原料であるパーフルオロ(2-メチル-1,2-エポキシプロピル)エーテルは、ヘプタフルオロイソブテニルエーテルをオゾン酸化することによって、ヘキサフルオロアセトンまたはその水和物を製造する際の副生成物として得られる(特許第2514368号公報、特許第3823339号公報)。なお、この反応で用いられるヘプタフルオロイソブテニルの低級アルキル、アリールまたはベンジルエーテルは、ヘキサフルオロプロペン製造時に副生するオクタフルオロイソブテンに低級アルコール類、フェノール類またはベンジルアルコールを付加した後、第四級アンモニウム塩などの相間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により脱HFすることによって得られる。
【0008】
パーフルオロ(2-メチル-1,2-エポキシプロピル)の低級アルキル、アリールまたはベンジルエーテルの熱分解反応は、不活性ガスまたは空気のようなキャリアガスと共に、金属製反応管を通過させることによって行われる。
【0009】
この熱分解反応は、約100〜600℃、好ましくは約250〜450℃の温度で行われる。これより低い温度では、分解速度が極端に遅くなり、経済上および効率上の観点からみて好ましくない。一方、これより高い温度では、異常な分解が進行し収率が低下するだけではなく、反応管、充填材の劣化が加速されるため好ましくない。
【0010】
キャリアガスは特に限定されないが、例えば窒素、ヘリウム、アルゴンのような不活性ガス、不活性ガス希釈酸素または空気等を用いることができる。
【0011】
金属製反応管の材質は特に限定されないが、例えばステンレス鋼、ニッケル、ハステロイ、インコネル、チタンなどを用いることができる。
【0012】
また、金属製反応管に充填物を充填して熱分解反応を行なう場合、充填物としては活性炭、モレキュラシーブ等の多孔質物質、鉄、銅、ニッケル、銀等の遷移金属を担持させた多孔質物質、アルミナ等の金属酸化物あるいはステンレス鋼、ニッケル等からなるヘリパック、ディクソンパッキング、ラシッヒリング等の金属製不規則充填物などを用いることができる。
【0013】
反応終了後は、分解生成ガスを水トラップ、氷冷却トラップおよびドライアイス/メタノールトラップに順次導いて生成物を捕集する方法が一般にとられ、主に水トラップおよび氷冷却トラップにヘキサフルオロアセトンが水和物水溶液として得られる。
【0014】
このような熱分解反応で得られる分解ガス中のヘキサフルオロアセトンは、GLC分析法によりその生成を確認することができるが、その分解ガス中には他の副生ガスが含まれているため、ヘキサフルオロアセトンをそのまま分離せず、一旦水中に分解ガスを導いて水和物とし、それを分離または分析する方法が簡単かつ便利な方法として用いられる。
【0015】
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、濃硫酸、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(特開昭57-81,433号公報、同59-157,045号公報)。
【0016】
【発明の効果】
ビスフエノールAF等の架橋剤中間体、医薬、農薬等の中間原料として有用であり、多岐にわたりその利用方法が見出されているヘキサフルオロアセトンまたはその水和物が、パーフルオロ(2-メチル-1,2-エポキシプロピル)の低級アルキル、アリールまたはべンジルエーテルの熱分解という全く新規な反応方法により得られた。この方法は、ヘプタフルオロイソブテニルの低級アルキル、アリールまたはベンジルエーテルをオゾン酸化する際、ヘキサフルオロアセトンと共に副生するパーフルオロ(2-メチル-1,2-エポキシプロピル)の低級アルキル、アリールまたはベンジルエーテルの有効利用としても有意義である。
【0017】
【実施例】
次に、実施例について本発明を説明する。
【0018】
実施例1
パーフルオロ(2-メチル-1,2-エポキシプロピル)メチルエーテル200g(純度48重量%:0.42モル)を、450℃に加熱したステンレス鋼製反応管(直径25mm×長さ1000mm)の上端入口から、流量0.1L/分の空気を流通させながら、約2時間かけて導入した。生成ガスは、反応管下端出口に接続した水トラップ(水200g収容)を通過させ、氷冷却トラップおよびドライアイス/メタノールトラップを経て、スクラバーヘ廃棄した。ヘキサフルオロアセトンは水トラップに捕集され、それの水和物水溶液として273g(純度23重量%:0.28モル)が得られた。ヘキサフルオロアセトン収率は67%(原料エーテル換算)であった。
【0019】
実施例2
実施例1において、反応管の加熱温度を200℃に、キャリアガスを流量0.1L/分の窒素にそれぞれ変更して、約4時間かけて原料を導入し、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液277g(純度9重量%:0.11モル)が得られ、その収率は26%であった。
【0020】
実施例3
実施例2において、反応管の加熱温度を250℃に変更して、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液220g(純度23重量%:0.23モル)が得られ、その収率は55%であった。
【0021】
実施例4
実施例2において、反応管の加熱温度を300℃に変更して、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液223g(純度26重量%:0.26モル)が得られ、その収率は62%であった。
【0022】
実施例5
実施例2において、反応管の加熱温度を400℃に変更して、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液216g(純度18重量%:0.18モル)が得られ、その収率は42%であった。
【0023】
実施例6
実施例1において、ステンレス鋼製ディクソンパッキング(6mmφ)を充填した反応管を用いて同様の操作を行った。ヘキサフルオロアセトン水和物水溶液270g(純度25重量%:0.31モル)が得られ、その収率は74%であった。
【0024】
実施例7
実施例6において、反応管の加熱温度を350℃に変更して、約15分間かけて原料を導入し、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液282g(純度23重量%:0.29モル)が得られ、その収率は70%であった。
【0025】
実施例8
実施例7において、反応管の加熱温度を300℃に変更して、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液276g(純度23重量%:0.29モル)が得られ、その収率は68%であった。
【0026】
実施例9
実施例7において、反応管の加熱温度を250℃に変更して、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液269g(純度24重量%:0.29モル)が得られ、その収率は69%であった。
【0027】
実施例10
実施例5において、銀担持活性炭を充填したした反応管を用い、キャリアガスを流量2.5L/分の窒素に変更して、約50分間かけて原料を導入し、同様の操作を行った。ヘキサフルオロアセトン水和物水溶液283g(純度24重量%:0.31モル)が得られ、その収率は73%であった。[0001]
[Industrial application fields]
The present invention relates to a method for producing hexafluoroacetone or a hydrate thereof. More specifically, the present invention relates to a process for producing hexafluoroacetone or a hydrate thereof for effective utilization of perfluoro (2-methyl-1,2-epoxypropyl) ether, which is a by-product of the reaction.
[0002]
[Prior art]
Hexafluoroacetone is used as a monomer for production of synthetic resins and synthetic rubbers, or as an intermediate material for cross-linking agents such as bisphenol AF, pharmaceuticals, agricultural chemicals, and the like.
[0003]
It has been proposed to manufacture hexafluoroacetone hydrate having such various uses by the following method.
[0004]
However, each of the above methods has the following drawbacks.
(1) Oxidation reaction with potassium permanganate is an industrial waste that is highly reactive and by-product manganese dioxide cannot be easily treated. (2) The oxide synthesized from hexafluoropropene must be of high purity. (3) In nitric acid oxidation of dithietane (hexafluorothioacetone dimer) in which hexafluoroacetone or the like is mixed in the product hexafluoroacetone, NO 2 is contained in the resulting hexafluoroacetone hydrate. and SO 2 are included, use of time-consuming (4) hex chloro acetone to that of removal, synthetically chlorine rather than only efficient increasing the weight, also require toxic antimony pentachloride, even higher It is difficult to obtain a pure product.
[Problems to be solved by the invention]
The object of the present invention is as an effective utilization method of perfluoro (2-methyl-1,2-epoxypropyl) ether which is a by-product in producing hexafluoroacetone by oxidizing ozone with heptafluoroisobutenyl ether. It is another object of the present invention to provide a process for producing hexafluoroacetone or a hydrate thereof.
[0006]
[Means for Solving the Problems]
The object of the present invention is to provide a general formula
Perfluoro (2-methyl-1,2-epoxypropyl) ether represented by the formula (where R is a lower alkyl group, aryl group or benzyl group) is thermally decomposed to produce hexafluoroacetone or a hydrate thereof. Is achieved.
[0007]
DETAILED DESCRIPTION OF THE INVENTION
Perfluoro (2-methyl-1,2-epoxypropyl) ether as a starting material is a by-product in producing hexafluoroacetone or its hydrate by ozone oxidation of heptafluoroisobutenyl ether ( Patent No. 2514368, Patent No. 3823339 ). The lower alkyl, aryl or benzyl ether of heptafluoroisobutenyl used in this reaction is obtained by adding a lower alcohol, phenol or benzyl alcohol to octafluoroisobutene by-produced during the production of hexafluoropropene, and then adding the fourth alcohol. It can be obtained by deHF treatment with a base such as alkali metal or alkaline earth metal hydroxide or carbonate or trialkylamine in the presence of a phase transfer catalyst such as a quaternary ammonium salt.
[0008]
The thermal decomposition reaction of perfluoro (2-methyl-1,2-epoxypropyl) lower alkyl, aryl or benzyl ether is carried out by passing it through a metal reaction tube together with a carrier gas such as an inert gas or air. Is called.
[0009]
This pyrolysis reaction is carried out at a temperature of about 100 to 600 ° C, preferably about 250 to 450 ° C. At temperatures lower than this, the decomposition rate becomes extremely slow, which is not preferable from the viewpoint of economy and efficiency. On the other hand, a temperature higher than this is not preferable because not only abnormal decomposition proceeds and the yield decreases, but also the deterioration of the reaction tube and filler is accelerated.
[0010]
The carrier gas is not particularly limited. For example, an inert gas such as nitrogen, helium, or argon, an inert gas diluted oxygen, or air can be used.
[0011]
The material of the metal reaction tube is not particularly limited. For example, stainless steel, nickel, hastelloy, inconel, titanium, or the like can be used.
[0012]
In addition, when conducting a thermal decomposition reaction by filling a metal reaction tube with a packing material, the packing material is a porous material such as activated carbon or molecular sieve, or a porous material carrying a transition metal such as iron, copper, nickel or silver. The material, metal oxides such as alumina, helicacs made of stainless steel, nickel, etc., metal irregular packings such as Dickson packing, Raschig ring, etc. can be used.
[0013]
After completion of the reaction, the decomposition gas is generally led to a water trap, an ice-cooled trap and a dry ice / methanol trap to collect the product, and hexafluoroacetone is mainly used in the water trap and ice-cooled trap. Obtained as an aqueous hydrate solution.
[0014]
The production of hexafluoroacetone in the cracked gas obtained by such a pyrolysis reaction can be confirmed by GLC analysis, but the by-product gas is contained in the cracked gas. As a simple and convenient method, hexafluoroacetone is not separated as it is, but a decomposition gas is once introduced into water to form a hydrate, which is separated or analyzed.
[0015]
The obtained hexafluoroacetone hydrate can be used as a solvent for polyesters, polyamides, etc., but when it is dehydrated, it is carried out by a method using phosphorus pentoxide, concentrated sulfuric acid, sulfuric anhydride or molecular sieves. (JP-A-57-81,433 and 59-157,045).
[0016]
【The invention's effect】
Hexafluoroacetone or its hydrate, which is useful as an intermediate raw material for cross-linking agents such as bisphenol AF, pharmaceuticals, agricultural chemicals, etc. and has been found to be used in various ways, is perfluoro (2-methyl- 1,2-epoxypropyl) was obtained by a completely new reaction method of thermal decomposition of lower alkyl, aryl or benzyl ether. In this method, when the lower alkyl, aryl or benzyl ether of heptafluoroisobutenyl is ozone-oxidized, the lower alkyl, aryl or perfluoro (2-methyl-1,2-epoxypropyl) produced as a by-product with hexafluoroacetone is produced. It is also significant as an effective use of benzyl ether.
[0017]
【Example】
Next, the present invention will be described with reference to examples.
[0018]
Example 1
Perfluoro (2-methyl-1,2-epoxypropyl) methyl ether 200g (purity 48% by weight: 0.42mol) was heated from the top end of a stainless steel reaction tube (diameter 25mm x length 1000mm) heated to 450 ° C. It was introduced over about 2 hours while circulating air at a flow rate of 0.1 L / min. The product gas was passed through a water trap (containing 200 g of water) connected to the lower end outlet of the reaction tube, passed through an ice cooling trap and a dry ice / methanol trap, and discarded to a scrubber. Hexafluoroacetone was collected in a water trap, and 273 g (purity 23 wt%: 0.28 mol) was obtained as an aqueous hydrate solution thereof. The hexafluoroacetone yield was 67% (in terms of raw material ether).
[0019]
Example 2
In Example 1, the heating temperature of the reaction tube was changed to 200 ° C., the carrier gas was changed to nitrogen at a flow rate of 0.1 L / min, the raw materials were introduced over about 4 hours, and the same operation was performed. 277 g of an aqueous hexafluoroacetone hydrate solution (purity 9% by weight: 0.11 mol) was obtained, and the yield was 26%.
[0020]
Example 3
In Example 2, the same operation was performed by changing the heating temperature of the reaction tube to 250 ° C. 220 g of hexafluoroacetone hydrate aqueous solution (purity 23% by weight: 0.23 mol) was obtained, and the yield was 55%.
[0021]
Example 4
In Example 2, the same operation was performed by changing the heating temperature of the reaction tube to 300 ° C. 223 g of hexafluoroacetone hydrate aqueous solution (purity 26% by weight: 0.26 mol) was obtained, and the yield was 62%.
[0022]
Example 5
In Example 2, the same operation was performed by changing the heating temperature of the reaction tube to 400 ° C. 216 g of hexafluoroacetone hydrate aqueous solution (purity 18% by weight: 0.18 mol) was obtained, and the yield was 42%.
[0023]
Example 6
In Example 1, the same operation was performed using a reaction tube filled with stainless steel Dixon packing (6 mmφ). 270 g of hexafluoroacetone hydrate aqueous solution (purity 25% by weight: 0.31 mol) was obtained, and the yield was 74%.
[0024]
Example 7
In Example 6, the heating temperature of the reaction tube was changed to 350 ° C., the raw material was introduced over about 15 minutes, and the same operation was performed. As a result, 282 g of hexafluoroacetone hydrate aqueous solution (purity 23 wt%: 0.29 mol) was obtained, and the yield was 70%.
[0025]
Example 8
In Example 7, the same operation was performed by changing the heating temperature of the reaction tube to 300 ° C. 276 g of hexafluoroacetone hydrate aqueous solution (purity 23% by weight: 0.29 mol) was obtained, and the yield was 68%.
[0026]
Example 9
In Example 7, the same operation was performed by changing the heating temperature of the reaction tube to 250 ° C. 269 g of hexafluoroacetone hydrate aqueous solution (purity 24% by weight: 0.29 mol) was obtained, and the yield was 69%.
[0027]
Example 10
In Example 5, a reaction tube filled with silver-supported activated carbon was used, the carrier gas was changed to nitrogen at a flow rate of 2.5 L / min, the raw material was introduced over about 50 minutes, and the same operation was performed. 283 g of hexafluoroacetone hydrate aqueous solution (purity 24% by weight: 0.31 mol) was obtained, and the yield was 73%.
Claims (6)
(ここでRは低級アルキル基、アリール基またはベンジル基である)で表わされるパーフルオロ(2-メチル-1,2-エポキシプロピル)エーテルを熱分解させることを特徴とするヘキサフルオロアセトンまたはその水和物の製造法。General formula
(Wherein R is a lower alkyl group, aryl group or benzyl group) perfluoro (2-methyl-1,2-epoxypropyl) ether represented by the thermal decomposition, hexafluoroacetone or water thereof Japanese manufacturing method.
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JP25820499A JP4534274B2 (en) | 1999-09-13 | 1999-09-13 | Method for producing hexafluoroacetone or hydrate thereof |
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JP25820499A JP4534274B2 (en) | 1999-09-13 | 1999-09-13 | Method for producing hexafluoroacetone or hydrate thereof |
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JP4396831B2 (en) | 2004-04-19 | 2010-01-13 | ダイキン工業株式会社 | Method for producing fluoroalkyl ketone hydrate |
US8853462B2 (en) | 2011-06-17 | 2014-10-07 | Unimatec Co., Ltd. | Method for producing hexafluoroacetone or hydrate thereof |
CN111848444A (en) * | 2020-08-14 | 2020-10-30 | 福建省漳平市九鼎氟化工有限公司 | Synthesis method of perfluoroisobutyronitrile |
CN114591158B (en) * | 2020-12-04 | 2024-01-30 | 福建省漳平市九鼎氟化工有限公司 | Method and device for preparing pentafluoropropionyl fluoride and hexafluoroacetone from perfluoro-2-methyl-2-pentene |
Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53119808A (en) * | 1977-03-29 | 1978-10-19 | Daikin Ind Ltd | Preparation of fluorinated oxygen-containing products |
JPS55130935A (en) * | 1979-03-31 | 1980-10-11 | Daikin Ind Ltd | Preparation of hexafluoroacetone |
JPS5862130A (en) * | 1981-10-09 | 1983-04-13 | Asahi Glass Co Ltd | Preparation of hexafluoroacetone |
JPS59181235A (en) * | 1983-03-30 | 1984-10-15 | Central Glass Co Ltd | Production of carbonyl compounds |
JPS61221144A (en) * | 1985-03-27 | 1986-10-01 | Nippon Mektron Ltd | Production of hexafluoroacetone |
JPS61277645A (en) * | 1985-06-03 | 1986-12-08 | Nippon Mektron Ltd | Production of hexafluoroacetone |
JPH01203339A (en) * | 1988-02-05 | 1989-08-16 | Nippon Mektron Ltd | Production of hexafluoroacetone or hydrate thereof |
JPH08333358A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Perfluoro(2-methyl-1,2-epoxypropyl) ether compound and its production |
JPH08333303A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Alpha, alpha-bis(trifluoromethyl) arylacetic ester and its production |
JPH08333298A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Production of alpha-(trifluoromethyl)arylacetic acid |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2514368B2 (en) * | 1987-07-21 | 1996-07-10 | 日本メクトロン株式会社 | Method for producing hexafluoroacetone or its hydrate |
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1999
- 1999-09-13 JP JP25820499A patent/JP4534274B2/en not_active Expired - Fee Related
Patent Citations (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53119808A (en) * | 1977-03-29 | 1978-10-19 | Daikin Ind Ltd | Preparation of fluorinated oxygen-containing products |
JPS55130935A (en) * | 1979-03-31 | 1980-10-11 | Daikin Ind Ltd | Preparation of hexafluoroacetone |
JPS5862130A (en) * | 1981-10-09 | 1983-04-13 | Asahi Glass Co Ltd | Preparation of hexafluoroacetone |
JPS59181235A (en) * | 1983-03-30 | 1984-10-15 | Central Glass Co Ltd | Production of carbonyl compounds |
JPS61221144A (en) * | 1985-03-27 | 1986-10-01 | Nippon Mektron Ltd | Production of hexafluoroacetone |
JPS61277645A (en) * | 1985-06-03 | 1986-12-08 | Nippon Mektron Ltd | Production of hexafluoroacetone |
JPH01203339A (en) * | 1988-02-05 | 1989-08-16 | Nippon Mektron Ltd | Production of hexafluoroacetone or hydrate thereof |
JPH08333358A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Perfluoro(2-methyl-1,2-epoxypropyl) ether compound and its production |
JPH08333303A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Alpha, alpha-bis(trifluoromethyl) arylacetic ester and its production |
JPH08333298A (en) * | 1995-06-08 | 1996-12-17 | Nippon Mektron Ltd | Production of alpha-(trifluoromethyl)arylacetic acid |
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