JPS6335539A - Production of hexafluoroisobutanoic acid - Google Patents
Production of hexafluoroisobutanoic acidInfo
- Publication number
- JPS6335539A JPS6335539A JP61181099A JP18109986A JPS6335539A JP S6335539 A JPS6335539 A JP S6335539A JP 61181099 A JP61181099 A JP 61181099A JP 18109986 A JP18109986 A JP 18109986A JP S6335539 A JPS6335539 A JP S6335539A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- alkyl ether
- hexafluoroisobutanoic
- water
- heptafluoroisobutenyl
- 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
- RAEAYTICAPHWJW-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)C(F)(F)F RAEAYTICAPHWJW-UHFFFAOYSA-N 0.000 title claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- -1 heptafluoroisobutenyl alkyl ether Chemical class 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 14
- 150000005215 alkyl ethers Chemical class 0.000 abstract description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract description 6
- 238000010992 reflux Methods 0.000 abstract description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002253 acid Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 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
- 239000002585 base Substances 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AQHKYFLVHBIQMS-UHFFFAOYSA-N 2-[difluoro(methoxy)methyl]-1,1,1,3,3,3-hexafluoropropane Chemical compound COC(F)(F)C(C(F)(F)F)C(F)(F)F AQHKYFLVHBIQMS-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005796 dehydrofluorination reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000003021 water soluble solvent Substances 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、ヘキサフルオロイソブタン酸の製造法に関す
る。更に詳しくは、オクタフルオロイソブタンの有効利
用を目的とするヘキサフルオロイソブタン酸の製造法に
関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing hexafluoroisobutanoic acid. More specifically, the present invention relates to a method for producing hexafluoroisobutanoic acid for the purpose of effectively utilizing octafluoroisobutane.
ヘキサフルオロイソブタン酸の製造は、従来オクタフル
オロイソブチンの加水分解によって行われている。しか
しながら、この方法は、毒性の強いオクタフルオロイソ
ブチンを出発物質として用いなければならないという欠
点を有している。Hexafluoroisobutanoic acid is conventionally produced by hydrolysis of octafluoroisobutyne. However, this method has the disadvantage that highly toxic octafluoroisobutyne must be used as a starting material.
このオクタフルオロイソブチンは、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製造時
の副生物であり、この毒性の強いオクタフルオロイソブ
チンは、一般に低級アルコール、例えばメタノール、エ
タノール、ｎ ７”ロバノール、イソプロパツール、
ｎ−ブタノールなどと、もはや毒性を示さないアルコー
ル付加物を容易に形成する性質を有している。This octafluoroisobutyne is a by-product during the production of hexafluoropropene, which is an important raw material for fluorine-containing copolymers.This highly toxic octafluoroisobutyne is generally used in lower alcohols such as methanol and ethanol. , n 7” lovanol, isopropanol,
It has the property of easily forming non-toxic alcohol adducts with n-butanol and the like.
形成されるアルコール付加物たるオクタフルオロイソブ
チルアルキルエーテル（ＣＨ３）２ＣＨＣＦ２０１’＜
ば、これをオートクレーブ中で濃硫酸と加熱する方法に
よってヘキサフルオロイソブタン酸エステル（ＣＦ３）
２ＣＨＣＯＯＲを与えるので（Ｉｚｖｅｓｔ Ａｋａ
ｄＮａｕｋ Ｓ 、Ｓ、Ｓ、Ｒ，０ｔｄｅｌ Ｋｈ
ｉｍ Ｎａｕｋ １９５６年第１３５３〜１３６０
頁）、これを加水分解してヘキサフルオロイソブタン酸
を製造する方法が当然に考えられる。The alcohol adduct formed is octafluoroisobutyl alkyl ether (CH3)2CHCF201'<
For example, hexafluoroisobutanoic acid ester (CF3) is produced by heating this with concentrated sulfuric acid in an autoclave.
Since it gives 2CHCOOR (Izvest Aka
dNauk S, S, S, R, 0tdel Kh
im Nauk 1956 No. 1353-1360
Page), and a method of hydrolyzing this to produce hexafluoroisobutanoic acid can naturally be considered.
しかしながら、このような一連の反応は、まず第１工程
のエステル化反応で濃硫酸を反応に用いたことによる装
置の腐食、有害なフルオロ硫酸の副生などという問題が
あり、また反応混合物中からのエステルの分離操作が困
難であるという問題に遭遇し、仮にこの問題が解決し得
たとしても今度は肝心の加水分解が円滑に進行しないと
いう問題にぶつかることになる。However, such a series of reactions has problems such as corrosion of the equipment due to the use of concentrated sulfuric acid in the esterification reaction in the first step and the production of harmful fluorosulfuric acid as a by-product. However, even if this problem were to be solved, the important problem would be that the hydrolysis would not proceed smoothly.
本発明者は、有毒なオクタフルオロイソブチンの有効な
利用のルートとなるオクタフルオロイソブチルアルキル
エーテルからヘキサフルオロイソブタン酸（ＣＦ３ ）
２ ＣＨＣＯＯＨを製造すべく種々の検討を行なった結
果、オクタフルオロイソブチルアルキルエーテルを一旦
ヘブタフルオロイソブテニルアルキルエーテルに変化さ
せ、これを水溶性有機溶媒の存在下にハロゲン化水素酸
を用いて反応させることにより、かかる課題が効果的に
解決されることを見出した。The present inventor has developed a method for converting hexafluoroisobutanoic acid (CF3) from octafluoroisobutyl alkyl ether, which is a route for effective utilization of toxic octafluoroisobutyne.
2 As a result of various studies to produce CHCOOH, we first changed octafluoroisobutyl alkyl ether to hebutafluoroisobutenyl alkyl ether, and then converted this into hexafluoroisobutyl alkyl ether using hydrohalic acid in the presence of a water-soluble organic solvent. It has been found that this problem can be effectively solved by causing the reaction.
従って、本発明はへキサフルオロイソブタン酸の製造法
に係り、ヘキサフルオロイソブタン酸の製造は、ヘプタ
フルオロイソブテニルアルキルエーテルを水溶性有機溶
媒の存在下に塩酸または臭化水素酸と反応させることに
より行われる。なお、アルキルエーテルのアルキル基は
、フェニル基で置換されたメチル基であるベンジル基の
如きアラルキル基であってもよい。Therefore, the present invention relates to a method for producing hexafluoroisobutanoic acid, and the production of hexafluoroisobutanoic acid involves reacting heptafluoroisobutenyl alkyl ether with hydrochloric acid or hydrobromic acid in the presence of a water-soluble organic solvent. This is done by The alkyl group of the alkyl ether may be an aralkyl group such as a benzyl group, which is a methyl group substituted with a phenyl group.
ヘプタフルオロイソブテニルアルキルエーテルは、オク
タフルオロイソブチルアルキルエーテルを脱フン化水素
化することにより容易に得ることができる（例えば、特
開昭５９−１０４３６４号公＠）。Heptafluoroisobutenyl alkyl ether can be easily obtained by dehydrofluorinating octafluoroisobutyl alkyl ether (for example, JP-A-59-104364).
（ＣＦ３）２ＣＨＣＦ ＯＲ二（ＣＦ３）２Ｃ＝ ＣＦ
ＯＲこの脱フン化水素化反応は、第４級アンモニウム塩
などの相間移動触媒の存在下に、アルカリ全屈またはア
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攪拌することにより行わ
れ、ヘプタフルオロイソブテニルアルキルエーテルはフ
ラッシュ蒸留および通常の蒸留により分離される。(CF3)2CHCF OR2 (CF3)2C= CF
This dehydrofluorination reaction is carried out by stirring with a base such as an alkali or alkaline earth metal hydroxide or carbonate or a trialkylamine in the presence of a phase transfer catalyst such as a quaternary ammonium salt. The heptafluoroisobutenyl alkyl ether is separated by flash distillation and conventional distillation.
ヘプタフルオロイソブテニルアルキルエーテルを用いて
のへキサフルオロイソブタン酸の製造は、ヘプタフルオ
ロイソブテニルアルキルエーテルに対して等モル量以上
、一般には１〜２０倍モルの塩酸または臭化水素酸を加
え、アセトン、アセトニトリル、テトラヒドロフランな
どの水溶性溶媒の還流条件下で一般に行われる。In the production of hexafluoroisobutanoic acid using heptafluoroisobutenyl alkyl ether, hydrochloric acid or hydrobromic acid is added in an amount equal to or more than the molar amount of heptafluoroisobutenyl alkyl ether, generally 1 to 20 times the molar amount. In addition, it is generally carried out under reflux conditions in a water-soluble solvent such as acetone, acetonitrile, or tetrahydrofuran.
本発明方法によれば、出発原料としてオクタフルオロイ
ソブチルアルキルエーテルを塩基で塩フッ化水素化する
ことにより容易に得られるヘプタフルオロイソブテニル
アルキルエーテルを用いることができ、目的物たるヘキ
サフルオロイソブタン酸は、それを水溶性有機溶媒の存
在下でハロゲン化水素酸と加熱還流するだけで容易に得
ることができるので、前記従来技術にみられたような欠
点をもはや有しない。しかも、その収率も良好である。According to the method of the present invention, heptafluoroisobutenyl alkyl ether, which is easily obtained by salt hydrofluorination of octafluoroisobutyl alkyl ether with a base, can be used as a starting material, and the target product, hexafluoroisobutanoic acid, can be used as a starting material. does no longer have the drawbacks seen in the prior art, since it can be easily obtained simply by heating to reflux with hydrohalic acid in the presence of a water-soluble organic solvent. Moreover, the yield is also good.
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
ジムロート冷却管、温度計、滴下ロートおよび攪拌装置
を備えた容量ＩＮのフラスコに、オクタフルオロイソブ
チルメチルエーテル２００ｇ （０，８６２モル）およ
びテトラメチルアンモニウムクロライド５．１ｇ （２
，５５ｆｆｉ量％）を仕込み、内容物の温度を１０〜２
０℃に保ちながら、８５％水酸化カリウム１３３ｇ（２
，０１５モル；２．３当量）を水１２０ｎＪに溶解させ
た溶液を３０分間の間に滴下した。滴下終了後１時間攪
拌し、分液、水洗して、ヘプタフルオロインブテニルメ
チルエーテル（沸点１０２〜１０４℃）を１７５ｇ （
収率９５．８％）（４た。Example 1 200 g (0,862 mol) of octafluoroisobutyl methyl ether and 5.1 g (2
, 55ffi amount%), and the temperature of the contents was adjusted to 10-2.
While keeping the temperature at 0℃, add 133g of 85% potassium hydroxide (2
, 015 mol; 2.3 equivalents) dissolved in 120 nJ of water was added dropwise over a period of 30 minutes. After the dropwise addition was completed, the mixture was stirred for 1 hour, separated, and washed with water to obtain 175 g of heptafluoroin butenyl methyl ether (boiling point 102-104°C).
Yield 95.8%) (4.
このヘプタフルオロイソブテニルメチルエーテル１５．
１ｇ （０，０７Ｌモル）および３６％濃硫酸１５ｇ
を、前記と同様装置の容量１００ｍｊ！のフラスコ中に
仕込み、アセトン３０＋ｓβを加えて１５時間還流条件
下で反応させた後、冷却、分液し、上層としてヘキサフ
ルオロイソブタン酸含量４６％（Ｆｎｎ＋ｒ内標法にょ
る）のアセトン溶液１３．７ｇ （収率９５．３％）
を得た。This heptafluoroisobutenyl methyl ether15.
1 g (0.07 L mol) and 15 g of 36% concentrated sulfuric acid
The capacity of the same device as above is 100mj! After adding acetone 30 + sβ and reacting under reflux conditions for 15 hours, cooling and separating the layers, an acetone solution 13. 7g (yield 95.3%)
I got it.
実施例２
実施例１において、３６％濃硫酸の代わりに４７％臭化
水素酸を用い、反応時間を１３時間に変更して反応を行
なうと、ヘキサフルオロイソブタン酸含量４７．５％（
Ｆｎｉｒ内標法による）のアセトン溶液１２．２ｇ（収
率８７．６％）が得られた。Example 2 In Example 1, when the reaction was carried out using 47% hydrobromic acid instead of 36% concentrated sulfuric acid and changing the reaction time to 13 hours, the hexafluoroisobutanoic acid content was 47.5% (
12.2 g (yield: 87.6%) of an acetone solution of Fnir internal standard method) was obtained.
比較例
実施例１において、アセトンを用いずに反応を行なうと
、１８時間還流後にも反応は、５〜８％程度しか進行し
ていなかった。Comparative Example In Example 1, when the reaction was carried out without using acetone, the reaction had progressed by only about 5 to 8% even after refluxing for 18 hours.
Claims (1)
水溶性有機溶媒の存在下に塩酸または臭化水素酸と反応
させることを特徴とするヘキサフルオロイソブタン酸の
製造法。1. Heptafluoroisobutenyl alkyl ether,
A method for producing hexafluoroisobutanoic acid, which comprises reacting it with hydrochloric acid or hydrobromic acid in the presence of a water-soluble organic solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61181099A JPH07112997B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroisobutanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61181099A JPH07112997B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroisobutanoic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6335539A true JPS6335539A (en) | 1988-02-16 |
| JPH07112997B2 JPH07112997B2 (en) | 1995-12-06 |
Family
ID=16094817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61181099A Expired - Fee Related JPH07112997B2 (en) | 1986-07-31 | 1986-07-31 | Method for producing hexafluoroisobutanoic acid |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07112997B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5573654A (en) * | 1994-03-04 | 1996-11-12 | Minnesota Mining And Manufacturing Company | Process for making hexafluoropropane and perfluoropropane |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
-
1986
- 1986-07-31 JP JP61181099A patent/JPH07112997B2/en not_active Expired - Fee Related
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5573654A (en) * | 1994-03-04 | 1996-11-12 | Minnesota Mining And Manufacturing Company | Process for making hexafluoropropane and perfluoropropane |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07112997B2 (en) | 1995-12-06 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |