JPH01135780A - Production of hexafluoropropene oxide - Google Patents
Production of hexafluoropropene oxideInfo
- Publication number
- JPH01135780A JPH01135780A JP29186087A JP29186087A JPH01135780A JP H01135780 A JPH01135780 A JP H01135780A JP 29186087 A JP29186087 A JP 29186087A JP 29186087 A JP29186087 A JP 29186087A JP H01135780 A JPH01135780 A JP H01135780A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- solvent
- hexafluoropropene
- compound
- oxygen
- 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
- PGFXOWRDDHCDTE-UHFFFAOYSA-N hexafluoropropylene oxide Chemical compound FC(F)(F)C1(F)OC1(F)F PGFXOWRDDHCDTE-UHFFFAOYSA-N 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- 239000010702 perfluoropolyether Substances 0.000 claims abstract description 11
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000001590 oxidative effect Effects 0.000 claims description 4
- -1 perfluoro Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 23
- 239000002904 solvent Substances 0.000 abstract description 15
- 238000000034 method Methods 0.000 abstract description 6
- 238000007254 oxidation reaction Methods 0.000 abstract description 6
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000003647 oxidation Effects 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 229910001882 dioxygen Inorganic materials 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- TXGPGHBYAPBDAG-UHFFFAOYSA-N 1,1,2,2,3,3-hexafluoro-4,4-bis(trifluoromethyl)cyclobutane Chemical compound FC(F)(F)C1(C(F)(F)F)C(F)(F)C(F)(F)C1(F)F TXGPGHBYAPBDAG-UHFFFAOYSA-N 0.000 description 1
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- OEERIBPGRSLGEK-UHFFFAOYSA-N carbon dioxide;methanol Chemical compound OC.O=C=O OEERIBPGRSLGEK-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical class FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ヘキサフルオロプロペンオキシドの製造法に
関する。更に詳しくは、ヘキサフルオロプロペンを酸素
で酸化してヘキサフルオロプロペンオキシドを製造する
方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing hexafluoropropene oxide. More specifically, the present invention relates to a method for producing hexafluoropropene oxide by oxidizing hexafluoropropene with oxygen.
ヘキサフルオロプロペンオキシドは、各種含フツ素化合
物、例えばヘキサフルオロアセトン、パーフルオロアル
キルビニルエーテルなどの合成原料として重要な化合物
であり、またそれのオリゴマー誘導体は潤滑油、熱媒な
どとしてハイテク分野で広く使用されている。Hexafluoropropene oxide is an important compound as a raw material for the synthesis of various fluorine-containing compounds, such as hexafluoroacetone and perfluoroalkyl vinyl ether, and its oligomer derivatives are widely used in high-tech fields as lubricating oils, heating media, etc. has been done.
かかる有用なヘキサフルオロプロペンオキシドの製造法
としては、種々の方法が従来から知られており、その概
略は本出願人の出願に係る発明を掲載した特公昭６１−
２１５５６’号公報に記載されている。Various methods have been known for the production of such useful hexafluoropropene oxide, and the outline thereof can be found in Japanese Patent Publication No. 1983-1999, which describes the invention claimed by the present applicant.
It is described in Japanese Patent No. 21556'.
こうした方法の内、ヘキサフルオロプロペンの酸素によ
る酸化反応を反応溶媒の点から検討したものが、特公昭
４５−１１６８３号公報に記載されている。Among these methods, one in which the oxidation reaction of hexafluoropropene with oxygen was studied from the viewpoint of the reaction solvent is described in Japanese Patent Publication No. 11683/1983.
この酸化反応では、１，１．２−トリクロロ−１，２，
２−トリフルオロエタン、トリクロロフルオロメタン、
パーフルオロ（ジメチルシクロブタン）、四塩化炭素な
どの飽和ハロ炭素が不活性な反応溶媒として用いられて
いるが、この反応の収率（転化率×選択率）は低く、高
々約５０〜６０％程度の水準にとどまっている。In this oxidation reaction, 1,1,2-trichloro-1,2,
2-trifluoroethane, trichlorofluoromethane,
Saturated halocarbons such as perfluoro(dimethylcyclobutane) and carbon tetrachloride are used as inert reaction solvents, but the yield (conversion rate x selectivity) of this reaction is low, about 50 to 60% at most. remains at the level of
また、この反応では高蒸気圧の溶媒として使用されてい
るため、反応終了後に粗製物をガス状にして回収する際
溶媒が同伴され、目的とする生成物を蒸留する前に、溶
媒分離のための蒸留工程を設けなければならないという
問題がある。更に、工業的生産の場では、同一溶媒を回
収しながら長期間にわたり継続使用するが、その際トリ
クロルトリフルオロエタンなどはへキサフルオロアセト
ンを多量に副生じ、その上フロン系化合物の使用はオゾ
ン層破壊のおそれありとして、現在グローバルな問題と
なっている。In addition, since this reaction uses a solvent with high vapor pressure, when the crude product is recovered in a gaseous state after the reaction, the solvent is entrained, and before the desired product is distilled, the solvent must be separated. There is a problem in that a distillation process must be provided. Furthermore, in industrial production sites, the same solvent is recovered and used continuously for a long period of time, but trichlorotrifluoroethane produces a large amount of hexafluoroacetone as a by-product, and the use of fluorocarbon compounds causes ozone This is currently a global issue due to the risk of layer destruction.
本発明の目的は、パーフルオロプロペンを酸素で酸化し
てパーフルオロプロペンオキシドを製造するに際し、使
用された反応溶媒についての余分な分離操作を必要とは
せず、また長期間同一溶媒を反復使用してもヘキサフル
オロアセトンの如き副生物を副生ぜず、しかも好収率で
目的物を与える方法を提供せんとするものであり、かか
る本発明の目的は前記−数式Ｅｌ］で表わされるパーフ
ルオロポリエーテル化合物を反応溶媒として用いること
により達成されることが見出された。The object of the present invention is to eliminate the need for extra separation operations for the reaction solvent used in producing perfluoropropene oxide by oxidizing perfluoropropene with oxygen, and to repeatedly use the same solvent for a long period of time. However, it is an object of the present invention to provide a method that does not produce by-products such as hexafluoroacetone and provides a desired product in a good yield. It has been found that this can be achieved by using a polyether compound as a reaction solvent.
従って、本発明は、ヘキサフルオロプロペンオキシドの
製造法に係り、ヘキサフルオロプロペンオキシドの製造
は、ヘキサフルオロプロペンを酸素で酸化するに際し、
反応溶媒として一般式％式％［］
（ここで、ＲｆおよびＲｆ’は互いに同一または異なる
パーフルオロ低級アルキうし基であり、Ｘは−ＣＦ （
ＣＦ、 ）−基または−ＣＦ、 ＣＦ２−基であり、そ
してｎおよびＩはそれぞれ０または１〜１００の整数で
あり、ＱはＯまたは１〜２００の整数であり、ｎとｍは
同時にＯとはならず、各パーフルオロオキシアルキレン
基は主顔中にランダムに分布している）で表わされるパ
ーフルオロポリエーテル化合物を用いることにより行わ
れる。Therefore, the present invention relates to a method for producing hexafluoropropene oxide, and the production of hexafluoropropene oxide includes the steps of oxidizing hexafluoropropene with oxygen.
As a reaction solvent, use the general formula % formula % [ ] (where Rf and Rf' are perfluoro lower alkyl groups that are the same or different from each other, and X is -CF (
CF, )- group or -CF, CF2- group, and n and I are each 0 or an integer from 1 to 100, Q is O or an integer from 1 to 200, and n and m are O and It is carried out by using a perfluoropolyether compound represented by (in which each perfluorooxyalkylene group is randomly distributed in the main face).
代表的なパーフルオロポリエーテル化合物としでは、従
来から次のようなものが知られている。The following are conventionally known as typical perfluoropolyether compounds.
Ｃ，Ｆ、０（ＣＦＣＦ、０）ｎＣ，Ｆ、
［ｎ ］ＣＦ。C,F,0(CFCF,0)nC,F,
[n]CF.
Ｃ３Ｆ、０（ＣＦ、ＣＦ２ＣＦ、０）ｎＣ２Ｆ、
［ｎＩコＣＦ、０（ＣＦＣＦ、０
）ｎ（ＣＦ、Ｏ） Ｑ ＣＦ３［ＩＶ］ＣＦ。C3F, 0(CF, CF2CF, 0)nC2F,
[nIcoCF, 0 (CFCF, 0
)n(CF,O) Q CF3[IV]CF.
ＣＦ、０（ＣＦ、ＣＦ、Ｏ）ｍ（ＣＦ、Ｏ） Ｑ ＣＦ
、 ［Ｖ ］（１，Ｆ、０（ＣＦＣＦ、０）
ｎ（ＣＦ、ＣＦ、０）ｍ（ＣＦ、Ｏ） Ｑ ＣＦ、
［ＶＩ］ＣＦ。CF, 0 (CF, CF, O) m (CF, O) Q CF
, [V](1,F,0(CFCF,0)
n(CF, CF, 0) m(CF, O) Q CF,
[VI]CF.
上記−数式［１１］で表わされる化合物は、ヘキサフル
オロプロペンオキシドオリゴマーの末端−ＣＯＦ基をフ
ッ素ガスと約１００〜３５０℃の温度で処理する方法に
よって得られ（特公昭６２〜１０４９０号公報）、ＮＫ
Ｌクリユーバー製品製品バリグルタュポン社製品りライ
トッシスなどの商品名で市販されている。また、上記−
数式［１１１］で表わされる化合物は、テトラフルオロ
オキセタンの開環重合によって得られた化合物を完全に
フッ素化することによって得られ、ダイキン製品デムナ
ムなどの商品名で市販されている。更に、上記−数式［
ＩＶ］〜［■コで表わされる化合物は、ヘキサフルオロ
プロペン、テトラフルオロエチレンまたはこれら両者の
光重合酸化によって得られた化合物からパーオキシド結
合を除去し、更に完全にフッ素化することによって得ら
れ、モンテフルオス社製品フォンブリンＹ、フォンブリ
ンＺ、フォンブリンになどの商品名で市販されている。The compound represented by formula [11] above is obtained by a method of treating the terminal -COF group of a hexafluoropropene oxide oligomer with fluorine gas at a temperature of about 100 to 350°C (Japanese Patent Publication No. 10490/1983), N.K.
L-Creuber products are commercially available under trade names such as Varigurtapon's Rilightossis. Also, above-
The compound represented by formula [111] is obtained by completely fluorinating a compound obtained by ring-opening polymerization of tetrafluorooxetane, and is commercially available under trade names such as Daikin product Demnum. Furthermore, the above − formula [
Compounds represented by IV] to [■ are obtained by removing peroxide bonds from compounds obtained by photopolymerization and oxidation of hexafluoropropene, tetrafluoroethylene, or both, and then completely fluorinating them. It is commercially available under the trade names Fomblin Y, Fomblin Z, Fomblin, etc.
これらのパーフルオロポリエーテル化合物の内、加熱加
圧下で高濃度の酸素と接触する反応系では。Among these perfluoropolyether compounds, in a reaction system in which they come into contact with high concentration of oxygen under heat and pressure.
（ＣＦ２０）基を有しない前記−数式［１１１または［
ｍｌで表わされる化合物を用いることが好ましい。(CF20) The above formula [111 or [
Preference is given to using compounds expressed in ml.
酸化反応に際し１反応熱を素早く分散除去し。Quickly disperses and removes reaction heat during oxidation reactions.
反応の円滑な制御を可能とさせるためには１反応溶媒の
沸点および粘度は低い方がよいが、あまり低すぎると反
応圧が高くなり、また反応終了後の粗製物回収の際溶媒
が同伴されるので、沸点については約１４０℃以上、好
ましくは約２５０℃以上のものが用いられる。In order to enable smooth control of the reaction, it is better for the boiling point and viscosity of the reaction solvent to be low, but if they are too low, the reaction pressure will increase and the solvent will be entrained when recovering the crude product after the reaction is completed. Therefore, the boiling point used is about 140°C or higher, preferably about 250°C or higher.
また、粘度については、約１〜１０００Ｃｓｔ（４０℃
）。In addition, the viscosity is approximately 1 to 1000Cst (40℃
).
好ましくは約１０〜４００Ｃｓｔ （４０℃）のものが
一般に用いられる。従って、かかる観点から、前記一般
式［１］において適当なｎ、ｍ、Ｑの数を有するものが
用いられる。即ち１次のようなものが、工業的に入手可
能である。Preferably, those having a temperature of about 10 to 400 Cst (40°C) are generally used. Therefore, from this point of view, those having appropriate numbers of n, m, and Q in the general formula [1] are used. That is, first order ones are commercially available.
化合物［■］： 粘度２〜１００６Ｃｓｔ（４０℃）Ｍ
Ｗ６６０〜１００００
ｎ＝２〜５８
化合物［■コニ 粘度２４〜２００Ｃｓｔ （４０℃）
ＭＷ２７００〜８４００
ｎ＝１４〜４９
化合物［■コニ 粘度２〜４２０Ｃｓｔ（４０℃）ＭＷ
６６０〜６８００
ｎ＝３〜４０．Ｑ＝１以下
化合物［■］： 粘度７〜３１５Ｃｓｔ（４０℃）Ｍ１
１１９００〜１６２３０
ｍ＝３〜７４．Ｑ＝２１−１８９
化合物［■コニ 粘度１５〜１０５Ｃｓｔ（４０℃）反
応には、加圧反応容器、一般にはオートクレーブが用い
られ、そこに反応溶媒およびヘキサフルオロプロペンを
仕込み、電気炉または加熱浴を用いて、約９０〜１４０
℃、好ましくは約１１０〜１３０℃の温度に昇温し、そ
こに酸素ガスをボンベなどから分添する。Compound [■]: Viscosity 2-1006 Cst (40°C) M
W660~10000 n=2~58 Compound [■Koni Viscosity 24~200Cst (40℃)
MW2700-8400 n=14-49 Compound [■Koni Viscosity 2-420Cst (40℃) MW
660-6800 n=3-40. Q=1 or less compound [■]: Viscosity 7-315Cst (40°C) M1
11900~16230 m=3~74. Q=21-189 Compound [■Koni Viscosity 15-105 Cst (40°C) A pressurized reaction vessel, generally an autoclave, is used for the reaction, the reaction solvent and hexafluoropropene are charged therein, and an electric furnace or heating bath is used. Approximately 90 to 140
C., preferably about 110 to 130.degree. C., and oxygen gas is added thereto from a cylinder or the like.
反応スケールが約１−１０Ω程度の場合には、反応のコ
ントロール性の点を考慮し、１回当り約０．５〜ＩＯＮ
Ｑの酸素を分添する。酸素のトータル仕込量は、理論
量１倍以上約２倍以内であり、収率などを考慮すれば約
１．５〜１．７倍である。反応圧に関しては、特別な条
件はないが、一般には約１０〜４０にｇ／ａｍ２である
。When the reaction scale is approximately 1-10Ω, approximately 0.5-ION
Add Q oxygen in portions. The total amount of oxygen charged is from 1 to about 2 times the theoretical amount, and about 1.5 to 1.7 times when considering the yield. Regarding the reaction pressure, there are no special conditions, but it is generally about 10 to 40 g/am2.
溶媒量に関しては、反応熱の分散、除去のためには多く
用いることが好ましいもののＪあまり過剰に用いると気
積°の量が減少し、反応圧の増大につながるので、一般
には反応容器内容積の約１０〜６０％の量で用いられ、
反応のコントロールおよび収率の点を総合的に勘案すれ
ば約３０〜５０％を占める量で用いることが好ましい。Regarding the amount of solvent, it is preferable to use a large amount in order to disperse and remove the reaction heat, but if too much is used, the amount of air will decrease and the reaction pressure will increase, so in general, the internal volume of the reaction vessel should be increased. It is used in an amount of about 10 to 60% of
If reaction control and yield are comprehensively taken into account, it is preferable to use an amount accounting for about 30 to 50%.
反応終了後は、オートクレーブを常温迄戻し、粗製物を
ガスとして回収する。この際、他の溶媒を用いた場合に
みられる回収時の同伴の問題は。After the reaction is completed, the autoclave is returned to room temperature and the crude product is recovered as a gas. At this time, there is the problem of entrainment during recovery that occurs when other solvents are used.
本発明の反応溶媒を使用した場合には溶媒の蒸気圧が低
いため問題とはならない。When the reaction solvent of the present invention is used, there is no problem because the vapor pressure of the solvent is low.
本発明方法によれば、パーフルオロポリエーテル化合物
を反応溶媒として用いることにより、使用した溶媒の余
分な分離操作を必要とはせず、また長期間同一溶媒を反
復使用してもヘキサフルオロアセトンのような副生物を
生成させることなく。According to the method of the present invention, by using a perfluoropolyether compound as a reaction solvent, there is no need for an extra separation operation of the used solvent, and even if the same solvent is repeatedly used for a long period of time, hexafluoroacetone can be easily removed. without producing any by-products.
好収率で目的物たるヘキサフルオロプロペンオキシドが
得られるという効果を奏する。The effect is that the desired product, hexafluoropropene oxide, can be obtained in good yield.
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
内容積１．２Ｑの攪拌機付ステンレス鋼製オートクレー
ブ内を減圧にした後、粘度１７ｃｓｔ（４０℃）。Example 1 After reducing the pressure inside a stainless steel autoclave with an internal volume of 1.2Q and equipped with a stirrer, the viscosity was 17cst (40°C).
沸点１７０℃１０．６Ｔｏｒｒの前記一般式［■］（た
だし、ｎ：１０）のパーフルオロポリエーテル９９５ｇ
（５５０ｍ Ｑ ）およびヘキサフルオロプロペン２２
０ｇを順次仕込み、外部加熱ヒーターにより内温が１２
０℃になる迄加熱した。このときの内圧は、２２Ｋｇ／
ｃｔｍ”である。995 g of perfluoropolyether of the general formula [■] (where n: 10) having a boiling point of 170°C and 10.6 Torr
(550m Q ) and hexafluoropropene 22
0g was added one by one, and the internal temperature was raised to 12.0g using an external heater.
It was heated until it reached 0°C. The internal pressure at this time was 22Kg/
ctm”.
この状態で酸素ガス０．８Ｎ Ｍを分添し、反応の開始
を示す温度上昇（１２５℃）を確認した後、自然放冷す
る。内温が１２０℃に下ったら、再度０．８〜２．ＯＮ
Ｑの酸素ガスを分添する。このような操作をくり返し、
所定の酸素量（２８Ｎ Ｑ ）を仕込〜だ後２０分間二
一ジングし、全反応時間を３．３時間とした。In this state, 0.8 N M of oxygen gas is added in portions, and after confirming a temperature rise (125° C.) indicating the start of the reaction, the mixture is allowed to cool naturally. When the internal temperature drops to 120℃, increase the temperature again to 0.8~2. ON
Add oxygen gas (Q) in portions. Repeat these operations,
After charging a predetermined amount of oxygen (28NQ), the mixture was heated for 20 minutes, giving a total reaction time of 3.3 hours.
反応終了後、常温迄放冷し、粗製物ガスをドライアイス
−メタノール浴で冷却した空のボンベに回収した。回収
量は２２０ｇであり、ガスクロマトグラフによるそれの
組成、転化率１選択率および収率（転化率×選択率）は
後記表に示される。After the reaction was completed, the reaction mixture was allowed to cool to room temperature, and the crude gas was collected in an empty cylinder cooled in a dry ice-methanol bath. The amount recovered was 220 g, and its composition, conversion rate 1 selectivity, and yield (conversion rate x selectivity) as determined by gas chromatography are shown in the table below.
実施例２
実施例１において、粘度３８９Ｃｓｔ （４０℃）、蒸
気圧Ｉ Ｘ １０−’Ｔｏｒｒ（１００℃）の前記一般
式［■］（ただし、ｎ＝４４））のパーフルオロポリエ
ーテル化合物が用いられた。Example 2 In Example 1, a perfluoropolyether compound of the general formula [■] (where n = 44) with a viscosity of 389 Cst (40 °C) and a vapor pressure of I x 10-'Torr (100 °C) was used. It was done.
実施例３
実施例１において、粘度２４Ｃｓｔ （４０℃）、蒸気
圧５ Ｘ １０−’Ｔｏｒｒ（１００℃）の前記−数式
［■］（ただし、ｎ＝１６）のパーフルオロポリエーテ
ル化合物が用いられ、全酸素仕込量を２５Ｎ Ｑとした
。Example 3 In Example 1, a perfluoropolyether compound having a viscosity of 24Cst (40°C) and a vapor pressure of 5 x 10-' Torr (100°C) and having the formula [■] (where n = 16) was used. The total amount of oxygen charged was 25NQ.
実施例４
実施例３において、粘度２６Ｃｓｔ （４０℃）、蒸気
圧Ｉ Ｘ １Ｏ−３Ｔｏｒｒ（１００℃）の前記−数式
［■コ（ただし。Example 4 In Example 3, the viscosity is 26Cst (40°C) and the vapor pressure I x 1O-3Torr (100°C) is calculated using the above-mentioned formula [■].
ｎ＝１１．Ｑ＝０．２８）のパーフルオロポリエーテル
化合物が用いられた。n=11. A perfluoropolyether compound with Q=0.28) was used.
比較例
実施例３において、反応溶媒としてトリクロロトリフル
オロエタンが用いられた。Comparative Example In Example 3, trichlorotrifluoroethane was used as the reaction solvent.
実施例２〜４および比較例での結果も、次の表に併記さ
れる。The results of Examples 2 to 4 and Comparative Example are also listed in the following table.
（以下余白）(Margin below)
Claims (1)
反応溶媒として一般式 ＲｆＯ（ＸＣＦ＿２Ｏ）ｎ（ＣＦ＿２ＣＦ＿２Ｏ）ｍ（
ＣＦ＿２Ｏ）ｌＲｆ’［ I ］（ここで、ＲｆおよびＲ
ｆ’は互いに同一または異なるパーフルオロ低級アルキ
ル基であり、Ｘは −ＣＦ（ＣＦ＿３）−基または−ＣＦ＿２ＣＦ＿２−基
であり、そしてｎおよびｍはそれぞれ０または１〜１０
０の整数であり、ｌは０または１〜２００の整数であり
、ｎとｍは同時に０とはならず、各パーフルオロオキシ
アルキレン基は主鎖中にランダムに分布している）で表
わされるパーフルオロポリエーテル化合物を用いること
を特徴とするヘキサフルオロプロペンオキシドの製造法
。 ２、粘度約１〜１０００Ｃｓｔ（４０℃）のパーフルオ
ロポリエーテル化合物が用いられる特許請求の範囲第１
項記載のヘキサフルオロプロペンオキシドの製造法。[Claims] 1. When oxidizing hexafluoropropene with oxygen,
The general formula RfO(XCF_2O)n(CF_2CF_2O)m(
CF_2O)lRf'[I] (where Rf and R
f' is a perfluoro lower alkyl group that is the same or different from each other, X is a -CF(CF_3)- group or a -CF_2CF_2- group, and n and m are each 0 or 1 to 10
is an integer of 0, l is 0 or an integer of 1 to 200, n and m are not 0 at the same time, and each perfluorooxyalkylene group is randomly distributed in the main chain) A method for producing hexafluoropropene oxide, characterized by using a perfluoropolyether compound. 2. Claim 1 in which a perfluoropolyether compound having a viscosity of about 1 to 1000 Cst (40°C) is used.
A method for producing hexafluoropropene oxide as described in .
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29186087A JP2514384B2 (en) | 1987-11-20 | 1987-11-20 | Method for producing hexafluoropropene oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29186087A JP2514384B2 (en) | 1987-11-20 | 1987-11-20 | Method for producing hexafluoropropene oxide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01135780A true JPH01135780A (en) | 1989-05-29 |
| JP2514384B2 JP2514384B2 (en) | 1996-07-10 |
Family
ID=17774360
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29186087A Expired - Lifetime JP2514384B2 (en) | 1987-11-20 | 1987-11-20 | Method for producing hexafluoropropene oxide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2514384B2 (en) |
-
1987
- 1987-11-20 JP JP29186087A patent/JP2514384B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2514384B2 (en) | 1996-07-10 |
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