JPS6320422B2 - - Google Patents
Info
- Publication number
- JPS6320422B2 JPS6320422B2 JP829582A JP829582A JPS6320422B2 JP S6320422 B2 JPS6320422 B2 JP S6320422B2 JP 829582 A JP829582 A JP 829582A JP 829582 A JP829582 A JP 829582A JP S6320422 B2 JPS6320422 B2 JP S6320422B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- difluoro
- och
- acid
- fluoride
- 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
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 6
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910001515 alkali metal fluoride Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 17
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 12
- 239000002994 raw material Substances 0.000 description 9
- 239000011698 potassium fluoride Substances 0.000 description 8
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical group F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 235000003270 potassium fluoride Nutrition 0.000 description 6
- 239000000463 material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 4
- 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 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229960002050 hydrofluoric acid Drugs 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- -1 sulfuric acid Chemical class 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920002313 fluoropolymer Polymers 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- VBZWSGALLODQNC-UHFFFAOYSA-N hexafluoroacetone Chemical compound FC(F)(F)C(=O)C(F)(F)F VBZWSGALLODQNC-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical group FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は、カルボニル化合物の製造法に関す
る。更に詳しくは、パーフルオロアルキル基で置
換されたカルボニル化合物の製造法に関する。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing carbonyl compounds. More specifically, the present invention relates to a method for producing a carbonyl compound substituted with a perfluoroalkyl group.
一般式R1R2CHCF2R3（ここで、R1およびR2は
水素原子またはパーフルオロアルキル基でその中
の少くとも１個はパーフルオロアルキル基であ
り、R3はアルキル基、アルコキシ基またはアリ
ールオキシ基である）で示される１，１−ジフル
オロ−１，２，２−トリ置換−2H化合物を、硫
酸の存在下で一般式R1R2CHCOR3（ここで、R1
〜R3は前記定義の如くである）に変換する方法
は、Bull.Acad.Sci.USSR.Div.Chem.Sci.1953年
第282頁やJ.Fluorine Chem.第３巻第63頁
（1973／74）などに記載されている。 General formula R 1 R 2 CHCF 2 R 3 (where R 1 and R 2 are hydrogen atoms or perfluoroalkyl groups, at least one of which is a perfluoroalkyl group, and R 3 is an alkyl group, an alkoxy A 1,1-difluoro-1,2,2-trisubstituted-2H compound represented by the general formula R 1 R 2 CHCOR 3 (where R 1
~R 3 is as defined above) is described in Bull. Acad. Sci. USSR. Div. Chem. Sci. 1953, p. 282 and J. Fluorine Chem. Vol. 3, p. /74) etc.
ところで、この反応の原料物質、例えば１，１
−ジフルオロ−１−メトキシ−２，２−ジパーフ
ルオロメチルエタンは、次のような方法によつ
て、パーフルオロイソブチレンとメタノールとか
ら合成される（Izv.Akad.Nauk SSSR第185巻第
1347頁、1972参照）。 By the way, the raw material for this reaction, for example 1,1
-Difluoro-1-methoxy-2,2-diperfluoromethylethane is synthesized from perfluoroisobutylene and methanol by the following method (Izv.Akad.Nauk SSSR Vol. 185).
(see p. 1347, 1972).
（CF3）2C−CF2＋CH3OH→
（CF3）2CHCF2OCH3＋（CF3）2C−CF（OCH3）
しかるに、この方法では大過剰に用いられたメ
タノールや副生した１−フルオロ−１−メトキシ
−２，２−ジパーフルオロメチルエチレンを分離
しなければ、次の反応に使用することができな
い。 (CF 3 ) 2 C−CF 2 +CH 3 OH→
(CF 3 ) 2 CHCF 2 OCH 3 + (CF 3 ) 2 C−CF(OCH 3 ) However, in this method, methanol used in large excess and by-produced 1-fluoro-1-methoxy-2,2- Unless diperfluoromethylethylene is separated, it cannot be used in the next reaction.
（CH3）2CHCF2OCH3＋H2SO4→
（CF3）2CHCOOCH3
（CF3）2C−CF（OCH3）2＋H2SO4→目的物が得
られない
更に、この反応では、硫酸などの強酸を使用し
ているため、廃水処理が必要であるばかりではな
く、フツ化水素が副生するため、その装置材料も
耐酸性、耐フツ酸性が必要となり、装置材料面で
の制限が多く、また劣化し易いという欠点を有し
ている。 (CH 3 ) 2 CHCF 2 OCH 3 +H 2 SO 4 →
(CF 3 ) 2 CHCOOCH 3 (CF 3 ) 2 C−CF(OCH 3 ) 2 +H 2 SO 4 → Target product cannot be obtained Furthermore, since this reaction uses strong acids such as sulfuric acid, it is difficult to treat wastewater. Not only is hydrogen fluoride required, but since hydrogen fluoride is produced as a by-product, the equipment materials must also be acid resistant and hydrofluoric acid resistant. There is.
しかるに、かかる硫酸処理反応に代えて、アル
コール類とフツ化物との存在下で反応を行ない、
次いで加水分解反応を行なうと、このような欠点
をなくして、所望の反応を遂行し得ることが見出
された。 However, instead of such a sulfuric acid treatment reaction, the reaction is carried out in the presence of an alcohol and a fluoride,
It has been found that if a hydrolysis reaction is then carried out, such drawbacks can be eliminated and the desired reaction can be carried out.
従つて、本発明は一般式R1R2CHCOR3（ここ
で、R1〜R3は前記定義の如くである）で示され
るカルボニル化合物の製造法に係り、このカルボ
ニル化合物は、一般式R1R2CHCF2R3（ここで、
R1〜R3は前記定義の如くである）で示される１，
１−ジフルオロ−１，２，２−トリ置換−2H化
合物を、アルコール類とアルカリ金属フツ化物と
の存在下で反応させた後、その反応生成物を加水
分解することにより製造される。 Therefore, the present invention relates to a method for producing a carbonyl compound represented by the general formula R 1 R 2 CHCOR 3 (wherein R 1 to R 3 are as defined above); 1 R 2 CHCF 2 R 3 (where,
R 1 to R 3 are as defined above) 1,
It is produced by reacting a 1-difluoro-1,2,2-trisubstituted-2H compound in the presence of an alcohol and an alkali metal fluoride, and then hydrolyzing the reaction product.
この場合の反応機構は、前記例示した化合物の
場合、次の如くであると考えられる。 The reaction mechanism in this case is considered to be as follows in the case of the compounds exemplified above.
（CF3）2CHCF2OCH3＋KF＋CH3OH→
〔（CF3）2C−CF（OCH3）〕＋KHF2
中間体
〔（CF3）2C−CF（OCH3）〕＋KF＋CH3OH→
（CF3）2C−Ｃ（OCH3）2＋KHF2
（CF3）2C−Ｃ（OCH3）2＋H2SO4→
（CF3）2CHCOOCH3
このような反応機構をとる結果、原料物質中に
含まれるメタノールや副生物は、それ自体この反
応の出発原料あるいは中間体原料として用いるこ
とができるので、それらの物質を合成された原料
物質中から分離する精製工程をもやは必要とはし
ない。更に、この反応では、発生するフツ化水素
がフツ化カリウムに吸収され、KHF2の形となる
ため、特にフツ酸に対する設備的な面での注意も
必要ではなくなり、またこのKHF2自体400℃以
上に加熱するとフツ化カリウムとフツ化水素とに
分解するので、フツ化カリウムとして再度使用す
ることができる。なお、目的とするジパーフルオ
ロメチル酢酸メチルエステルは90％以上の好収率
で得られるが、加水分解されないで未反応のまま
の中間体１，１−ジメトキシ−２，２−ジパーフ
ルオロエチレンは、反応生成物から分離した後過
マンガン酸カリウム−硫酸で酸化すると、有用な
ヘキサフルオロアセトンに誘導することができ
る。 (CF 3 ) 2 CHCF 2 OCH 3 +KF＋CH 3 OH→
[(CF 3 ) 2 C−CF(OCH 3 )]+KHF 2 intermediate [(CF 3 ) 2 C−CF(OCH 3 )]+KF+CH 3 OH→
(CF 3 ) 2 C−C(OCH 3 ) 2 +KHF 2 (CF 3 ) 2 C−C(OCH 3 ) 2 +H 2 SO 4 →
(CF 3 ) 2 CHCOOCH 3As a result of this reaction mechanism, methanol and by-products contained in the raw materials can themselves be used as starting materials or intermediate materials for this reaction, so these materials can be used as starting materials or intermediate materials. There is no longer a need for a purification step to separate the synthesized raw materials. Furthermore, in this reaction, the generated hydrogen fluoride is absorbed by potassium fluoride and becomes KHF 2 , so there is no need to be particularly careful about the equipment for fluoric acid, and this KHF 2 itself is heated to 400℃. When heated above, it decomposes into potassium fluoride and hydrogen fluoride, so it can be used again as potassium fluoride. Although the desired diperfluoromethylacetic acid methyl ester is obtained with a good yield of 90% or more, the intermediate 1,1-dimethoxy-2,2-diperfluoroethylene remains unreacted without being hydrolyzed. can be separated from the reaction product and oxidized with potassium permanganate-sulfuric acid to give useful hexafluoroacetone.
原料物質としては、１，１−ジフルオロ−１−
メトキシ−２，２−ジパーフルオロメチルエタン
の他に、１，１−ジフルオロ−１−エトキシ−
２，２−ジパーフルオロメチルエタン、１，１−
ジフルオロ−１−メトキシ−２−パーフルオロメ
チル−２−パーフルオロエチルエタン、１，１−
ジフルオロ−１−メトキシ−２−パーフルオロメ
チルエタンなどが用いられる。 As a raw material, 1,1-difluoro-1-
In addition to methoxy-2,2-diperfluoromethylethane, 1,1-difluoro-1-ethoxy-
2,2-diperfluoromethylethane, 1,1-
Difluoro-1-methoxy-2-perfluoromethyl-2-perfluoroethylethane, 1,1-
Difluoro-1-methoxy-2-perfluoromethylethane and the like are used.
これと反応するアルコール類として、例えばメ
タノール、エタノール、プロパノール、ブタノー
ル、ベンジルアルコールなどが用いられる。この
場合、前述の如く原料物質の合成時に用いられた
ものを、そのまま用いることもできる。 Examples of alcohols that can be used to react with this include methanol, ethanol, propanol, butanol, and benzyl alcohol. In this case, as described above, those used in the synthesis of the raw materials can also be used as they are.
アルカリ金属フツ化物としては、フツ化ナトリ
ウム、フツ化カリウムなどが一般に用いられ、こ
れらのアルカリ金属フツ化物は、前記反応式から
も分るように、原料物質に対して２以上のモル比
で用いられることが好ましい。勿論、それ以下の
モル比でも反応するが、その場合には反応の速度
が遅くなる。反応温度は、室温でもよいが、一般
には、用いられたアルコール類の還流温度が用い
られる。 As the alkali metal fluoride, sodium fluoride, potassium fluoride, etc. are generally used, and as can be seen from the above reaction formula, these alkali metal fluorides are used in a molar ratio of 2 or more to the raw material. It is preferable that Of course, the reaction can occur at a lower molar ratio, but in that case the reaction rate becomes slower. The reaction temperature may be room temperature, but generally the reflux temperature of the alcohol used is used.
加水分解反応は、塩酸、硫酸、リン酸などの無
機酸を用いて、一般に室温で行われる。反応終了
後は、水層と分離した油層についての分留が行わ
れ、目的物が取得される。 The hydrolysis reaction is generally carried out at room temperature using an inorganic acid such as hydrochloric acid, sulfuric acid, or phosphoric acid. After the reaction is completed, the oil layer separated from the water layer is subjected to fractional distillation to obtain the target product.
このようにして製造されるパーフルオロアルキ
ル基で置換されたカルボニル化合物は、それを脱
フツ化水素化したメタクリル酸型化合物としてフ
ツ素系重合体原料に、またそれを還元したフルオ
ロアルコールを溶媒などに、更にそのフルオロア
ルコールでエステル化された（メタ）アクリル酸
エステル化合物を重合体原料などにそれぞれ用い
ることができ、これらの各重合体原料を単独また
は共重合させて得られる重合体はＸ線レジスト材
料などとして有用である。 The carbonyl compound substituted with a perfluoroalkyl group produced in this way is dehydrofluorinated as a methacrylic acid type compound and used as a raw material for a fluorinated polymer, and the reduced fluoroalcohol is used as a solvent. Furthermore, the (meth)acrylic acid ester compound esterified with the fluoroalcohol can be used as a polymer raw material, etc., and the polymer obtained by copolymerizing each of these polymer raw materials alone or by copolymerization is X-ray resistant. It is useful as a resist material, etc.
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
１，１−ジフルオロ−１−メトキシ−２，２−
ジパーフルオロメチルエタン
（CF3）2CHCF2OCH311.6g、フツ化カリウム6.4g
およびメタノール20mlの混合物を、撹拌しながら
加熱還流させる。約10分間経過するとフツ化カリ
ウムがのり状となり（KHF2に変化しているもの
と推察される）、約15分間では混合物全体がペー
スト状となり、約60分間で反応を終了させる。Example 1,1-difluoro-1-methoxy-2,2-
Diperfluoromethylethane (CF 3 ) 2 CHCF 2 OCH 3 11.6g, potassium fluoride 6.4g
A mixture of 20 ml of methanol and 20 ml of methanol is heated to reflux with stirring. After about 10 minutes, the potassium fluoride becomes paste-like (presumably changed to KHF 2 ), and after about 15 minutes, the entire mixture becomes paste-like, and the reaction is completed in about 60 minutes.
反応混合物をロ過し、ロ過物をメタノールで洗
浄し、ロ液からメタノールを減圧留去する。残渣
に6N塩酸を加えて加水分解した後、氷浴で冷却
する。水中に注いで分離した油層を分離し、水
洗、乾燥後分留した。沸点85〜87℃（常圧）の第
１留分が9.5g（収率90％）得られ、更に蒸留を続
けると、沸点72〜73℃／12mmHgの第２留分が
0.6g（収率5.7％）が得られた。この第１留分は、
標準物質とNMRで同定した結果、ジパーフルオ
ロメチル酢酸メチルエステル
（CF3）2CHCOOCH3であることが確認され、また
第２留分はパーフルオロメチルマロン酸ジメチル
エステルCF3CH（COOCH3）2であることが確認さ
れた。 The reaction mixture is filtered, the filtered product is washed with methanol, and the methanol is distilled off from the filtered solution under reduced pressure. After hydrolyzing the residue by adding 6N hydrochloric acid, it is cooled in an ice bath. The oil layer was separated by pouring it into water, washed with water, dried, and fractionated. 9.5g (90% yield) of the first fraction with a boiling point of 85-87℃ (normal pressure) was obtained, and when the distillation was continued, a second fraction with a boiling point of 72-73℃/12mmHg was obtained.
0.6g (yield 5.7%) was obtained. This first fraction is
As a result of identification using standard substances and NMR, it was confirmed that it was diperfluoromethylacetic acid methyl ester (CF 3 ) 2 CHCOOCH 3 , and the second fraction was perfluoromethylmalonic acid dimethyl ester CF 3 CH (COOCH 3 ). It was confirmed that 2 .
なお、この第２留分は、第１留分から次のよう
な反応機構によつて生成したものと推定される。 It is presumed that this second fraction was produced from the first fraction by the following reaction mechanism.
（CF3）2CHCOOCH3→CF2−Ｃ（CF3）
COOCH3→CH3OCF2CH（CF3）COOCH3→
CF3CH（COOCH3）2
〔各留分の確認データー〕
第１留分： 19F−NMR −13.0ppm（ｄ，Ｊ−
7.0Hz）〔CF3COOH外部標準〕
Ｈ−NMR CH33.8ppm
CH3.9ppm（heptetJ−
7.0Hz）
第２留分： 19F−NMR −11.0ppm（ｄ，Ｊ−
8.1Hz）〔CF3COOH外部標準〕
Ｈ−NMR CH33.82ppm
CH 4.17ppm
（quartetJ−8.1Hz） (CF 3 ) 2 CHCOOCH 3 →CF 2 −C(CF 3 )
COOCH 3 → CH 3 OCF 2 CH (CF 3 ) COOCH 3 →
CF 3 CH (COOCH 3 ) 2 [Confirmation data for each fraction] 1st distillate: 19 F−NMR −13.0ppm (d, J−
7.0Hz) [CF 3 COOH external standard] H-NMR CH 3 3.8ppm CH3.9ppm (heptetJ-
7.0Hz) Second fraction: 19 F−NMR −11.0ppm (d, J−
8.1Hz) [CF 3 COOH external standard] H-NMR CH 3 3.82ppm CH 4.17ppm
(quartetJ−8.1Hz)
Claims (1)
は水素原子またはパーフルオロアルキル基でその
中の少なくとも１個はパーフルオロアルキル基で
あり、R3はアルコキシ基である）で示される１，
１−ジフルオロ−１，２，２−トリ置換−2H化
合物を、低級アルコール類とアルカリ金属フツ化
物との存在下で反応させた後、その反応生成物を
加水分解することを特徴とする一般式
R1R2CHCOR3（ここで、R1〜R3は前記定義の如
くである）で示されるカルボニル化合物の製造
法。1 General formula R 1 R 2 CHCF 2 R 3 (where R 1 and R 2
is a hydrogen atom or a perfluoroalkyl group, at least one of which is a perfluoroalkyl group, and R 3 is an alkoxy group)
A general formula characterized by reacting a 1-difluoro-1,2,2-trisubstituted-2H compound in the presence of a lower alcohol and an alkali metal fluoride, and then hydrolyzing the reaction product.
A method for producing a carbonyl compound represented by R 1 R 2 CHCOR 3 (wherein R 1 to R 3 are as defined above).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP829582A JPS58126837A (en) | 1982-01-22 | 1982-01-22 | Preparation of carbonyl compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP829582A JPS58126837A (en) | 1982-01-22 | 1982-01-22 | Preparation of carbonyl compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58126837A JPS58126837A (en) | 1983-07-28 |
| JPS6320422B2 true JPS6320422B2 (en) | 1988-04-27 |
Family
ID=11689162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP829582A Granted JPS58126837A (en) | 1982-01-22 | 1982-01-22 | Preparation of carbonyl compound |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58126837A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3635750C2 (en) * | 1985-10-21 | 1994-08-25 | Daikin Ind Ltd | Fluorine-containing compound, process for its preparation and its use |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
-
1982
- 1982-01-22 JP JP829582A patent/JPS58126837A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58126837A (en) | 1983-07-28 |
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