JPS6116372B2 - - Google Patents
Info
- Publication number
- JPS6116372B2 JPS6116372B2 JP7704082A JP7704082A JPS6116372B2 JP S6116372 B2 JPS6116372 B2 JP S6116372B2 JP 7704082 A JP7704082 A JP 7704082A JP 7704082 A JP7704082 A JP 7704082A JP S6116372 B2 JPS6116372 B2 JP S6116372B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- reaction
- alkylperfluoropropene
- mole
- dimethylformamide
- 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- 238000004519 manufacturing process Methods 0.000 claims description 7
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- -1 alkyl perfluoropropene Chemical compound 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000013076 target substance Substances 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本発明は、２−アルキルパーフルオロプロペン
の製法に関し、更に詳しくは、２−アルキルパー
フルオロイソブチリルフルオリドを特定のアミド
と反応させることから成る２−アルキルパーフル
オロプロペンの製法に関する。
２−アルキルパーフルオロプロペンは、ポリテ
トラフルオロエチレンなどの含フツ素重合体の改
質剤として有用である。
本発明者らは、２−アルキルパーフルオロプロ
ペンの有利な製法について研究を重ねた結果、２
−アルキルパーフルオロイソブチリルフルオリド
をジメチルホルムアミドまたはジメチルアセトア
ミドと反応させることにより容易に２−アルキル
パーフルオロプロペンが得られることを見い出し
本発明を完成するに至つた。
すなわち、本発明の要旨は、式：
〔式中、Ｒは炭素数１〜４のアルキル基を表わ
す。〕
で示される酸フルオリドを加熱下にジメチルホ
ルムアミドまたはジメチルアセトアミドと反応さ
せて、式：
で示される化合物を得ることを特徴とする２−
アルキルパーフルオロプロペンの製法に存する。
本発明における反応は、加熱下、好ましくは80
〜230℃の温度において行なわれる。
さらに、反応は溶媒の存在下で行なつてもよく
好ましい溶媒としては、ベンゼン、トルエン、ク
ロルベンゼン、アセトニトリル、ジグライムなど
が挙げられる。
酸フルオリド（）は、たとえば式：
で示される化合物を20〜60℃の温度でジメチルホ
ルムアミドまたはジメチルアセトアミドと反応さ
せることにより容易に得られる。
得られた酸アミドは、分離して、または分離す
ることなく本発明の製法に供することができる。
さらに、化合物（）を80〜230℃の加熱下に
ジメチルホルムアミドまたはジメチルアセトアミ
ドと反応させることにより２−アルキルパーフル
オロプロペン（）を得ることもできる。
次に実施例を示し、本発明を具体的に説明す
る。
実施例 １
内容積100mlのステンレス製オートクレーブに
DMF（
The present invention relates to a method for producing 2-alkylperfluoropropene, and more particularly to a method for producing 2-alkylperfluoropropene, which comprises reacting 2-alkylperfluoroisobutyryl fluoride with a specific amide. 2-Alkylperfluoropropene is useful as a modifier for fluorine-containing polymers such as polytetrafluoroethylene. As a result of repeated research into an advantageous method for producing 2-alkylperfluoropropene, the present inventors found that 2-alkylperfluoropropene
The present inventors have discovered that 2-alkylperfluoropropene can be easily obtained by reacting -alkylperfluoroisobutyryl fluoride with dimethylformamide or dimethylacetamide, leading to the completion of the present invention. That is, the gist of the present invention is that the formula: [In the formula, R represents an alkyl group having 1 to 4 carbon atoms. ] The acid fluoride represented by is reacted with dimethylformamide or dimethylacetamide under heating to form the formula: 2- characterized by obtaining a compound represented by
It consists in a method for producing alkyl perfluoropropene. The reaction in the present invention is carried out under heating, preferably at 80°C.
It is carried out at a temperature of ~230°C. Furthermore, the reaction may be carried out in the presence of a solvent, and preferred solvents include benzene, toluene, chlorobenzene, acetonitrile, diglyme, and the like. Acid fluoride () has the formula, for example: It can be easily obtained by reacting the compound represented by with dimethylformamide or dimethylacetamide at a temperature of 20 to 60°C. The obtained acid amide can be subjected to the production method of the present invention with or without separation. Furthermore, 2-alkylperfluoropropene () can also be obtained by reacting compound () with dimethylformamide or dimethylacetamide while heating at 80 to 230°C. Next, examples will be shown to specifically explain the present invention. Example 1 In a stainless steel autoclave with an internal volume of 100ml
DMF (
【式】）7.3g（1.1mole）とCH3−
Ｃ（CF3）2COF 21.2g（0.1mole）を仕込み、撹
拌下オイルバス中で120℃に保つた。10時間後に
反応圧は4.5Kg／cm2Ｇを示し、気相部組成は、ガ
スクロマトグラフイ分析の結果、CO242％
[Formula]) 7.3 g (1.1 mole) and CH 3 - C (CF 3 ) 2 COF 21.2 g (0.1 mole) were charged and kept at 120°C in an oil bath with stirring. After 10 hours, the reaction pressure showed 4.5Kg/cm 2 G, and the gas phase composition was 42% CO 2 as a result of gas chromatography analysis.
【式】29.9％[Formula] 29.9%
【式】0.1％およ
び原料酸フルオリド28％であつた。
更に２時間後、オートクレーブの圧力が常圧に
なるまで生成ガスを10％NaOH水溶液および塩化
カルシウム管を通して排出し、液体酸素で冷却し
たコールドラツプ中に生成物10.2gを捕集した。
捕集された生成物は、目的物98％と
[Formula] 0.1% and raw acid fluoride 28%. After an additional 2 hours, the product gas was vented through a 10% aqueous NaOH solution and calcium chloride tubing until the pressure of the autoclave reached normal pressure, and 10.2 g of product was collected in a cold trap cooled with liquid oxygen.
The collected product contains 98% of the target substance.
【式】２％を含んでいた。これより目的
物収率は68.5％と計算される。
実施例 ２
実施例１と同様の操作において、CH3C
（CF3）2COF5.3g（0.025mole）およびDMF11g
（0.15mole）を用い、反応温度を160℃、反応時間
を４時間としたところ、トラツプ量は3.2gであ
り、目的物は92％含まれ、残りは[Formula] Contained 2%. From this, the yield of the target product is calculated to be 68.5%. Example 2 In the same operation as Example 1, CH 3 C
( CF3 ) 2 COF5.3g (0.025mole) and DMF11g
(0.15 mole), the reaction temperature was 160℃, and the reaction time was 4 hours.The amount of trap was 3.2g, containing 92% of the target substance, and the remaining
【式】
であつた。これより目的物収率は80％と計算され
る
実施例 ３
実施例１と同様の操作において、CH3C
（CF3）2COF15g（0.071mole）およびＮ，N′−ジ
メチルアセトアミド18.7g（0.215mol）を用い、
反応温度を190℃、反応時間を２時間としたとこ
ろ、トラツプされた量は10.8gであり目的物は
65.2％含まれ、残りは[Formula] It was. From this, the yield of the target product is calculated to be 80%. Example 3 In the same operation as in Example 1, CH 3 C
(CF 3 ) 2 using 15 g (0.071 mole) of COF and 18.7 g (0.215 mol) of N,N'-dimethylacetamide,
When the reaction temperature was 190℃ and the reaction time was 2 hours, the amount trapped was 10.8g and the target product was
65.2% included, the rest
【式】であつた。
これより目的物収率は65％と計算される。
実施例 ４
実施例１と同様に、（CF3）2C＝CFOC2H511g
（0.05mole）およびDMF7.3g（0.1mole）を仕込
み、撹拌下120℃に６時間保つた。気相部の分析
よりIt was [formula]. From this, the yield of the target product is calculated to be 65%. Example 4 Same as Example 1, (CF 3 ) 2 C=CFOC 2 H 5 11g
(0.05 mole) and 7.3 g (0.1 mole) of DMF were charged and kept at 120°C for 6 hours while stirring. From gas phase analysis
【式】およびC2H5C（CF3）2COF の生成が認められた。The formation of [Formula] and C 2 H 5 C(CF 3 ) 2 COF was observed.
Claims (1)
す。〕 で示される酸フルオリドを加熱下にジメチルホ
ルムアミドまたはジメチルアセトアミドと反応さ
せて、式： で示される化合物を得ることを特徴とする２−
アルキルパーフルオロプロペンの製法。 ２ 反応温度が80〜230℃である特許請求の範囲
第１項記載の製法。 ３ 溶媒の存在下に反応を行なう特許請求の範囲
第１項または第２項記載の製法。[Claims] 1 Formula: [In the formula, R represents an alkyl group having 1 to 4 carbon atoms. ] The acid fluoride represented by is reacted with dimethylformamide or dimethylacetamide under heating to form the formula: 2- characterized by obtaining a compound represented by
Process for producing alkyl perfluoropropene. 2. The manufacturing method according to claim 1, wherein the reaction temperature is 80 to 230°C. 3. The manufacturing method according to claim 1 or 2, wherein the reaction is carried out in the presence of a solvent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7704082A JPS58194824A (en) | 1982-05-07 | 1982-05-07 | Preparation of 2-alkylperfluoropropene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7704082A JPS58194824A (en) | 1982-05-07 | 1982-05-07 | Preparation of 2-alkylperfluoropropene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58194824A JPS58194824A (en) | 1983-11-12 |
| JPS6116372B2 true JPS6116372B2 (en) | 1986-04-30 |
Family
ID=13622650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7704082A Granted JPS58194824A (en) | 1982-05-07 | 1982-05-07 | Preparation of 2-alkylperfluoropropene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS58194824A (en) |
-
1982
- 1982-05-07 JP JP7704082A patent/JPS58194824A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS58194824A (en) | 1983-11-12 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP4358317B2 (en) | Triazine ring-containing compound | |
| JP2004537502A (en) | Manufacture of fluorine compounds | |
| US4260561A (en) | Process for the preparation of carbonyl difluorides | |
| JPH03106848A (en) | Preparation of derivative of alpha-fluoroacryloyl | |
| EP0833811B1 (en) | A process for the preparation of esters | |
| JPH05255362A (en) | Preparation of tertiary phosphine | |
| JPS6116372B2 (en) | ||
| JPS61249964A (en) | Preparation of 3,4,5,6-tetrachloro-2-trichloromethylpyridinerich mixture | |
| EP0259663B1 (en) | Process for producing tetrafluorophihalic acid | |
| JP2725179B2 (en) | Method for producing 2,4,5-trifluoro-3-hydroxybenzoic acid | |
| JPH0258254B2 (en) | ||
| JPS638102B2 (en) | ||
| JPH0133464B2 (en) | ||
| JPH0995458A (en) | Production of fluorinated hydrocarbon compound | |
| JP3046258B2 (en) | Method for producing 1-chlorocarbonyl-4-piperidinopiperidine or hydrochloride thereof | |
| JPH0272162A (en) | Production of 3, 5, 6-trichlorropyridine-2- aryl and novel aryl-4-cyano-2, 2, 4- trichlorobutylate compound used therein | |
| JP3293676B2 (en) | Process for producing halomaleic acid and halofumarate esters | |
| JPH0317830B2 (en) | ||
| JP2893546B2 (en) | 4-Bromo-3,5,6-trifluorophthalic acid and its preparation, 3-bromo-2,4,5-trifluorobenzoic acid | |
| JPH0242824B2 (en) | ||
| JP3135659B2 (en) | Method for producing perfluoro-oxyaziridine | |
| JP3038380B1 (en) | Method for producing ketene imine compound | |
| JP3760253B2 (en) | Process for producing 4-fluorosalicylic acids | |
| JP2536030B2 (en) | Method for producing aminophenol alkyl ether | |
| JPS6216946B2 (en) |