JP2001192347A5 - - Google Patents
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- JP2001192347A5 JP2001192347A5 JP2000313523A JP2000313523A JP2001192347A5 JP 2001192347 A5 JP2001192347 A5 JP 2001192347A5 JP 2000313523 A JP2000313523 A JP 2000313523A JP 2000313523 A JP2000313523 A JP 2000313523A JP 2001192347 A5 JP2001192347 A5 JP 2001192347A5
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即ち、本発明の具体的態様においては、工業的に入手可能なあるいは種々の手法によって合成の可能なテトラハロゲン化ペルフルオロアルカンを−78℃から+200℃の範囲でテトラヒドロフランなどの有機溶媒中、触媒として適量のハロゲン化アルキルの存在下、Mg,Zn,Cd,Al,Cu,NaまたはLiなどの金属と反応させ、脱ハロゲン反応を行うことによって高収率でα,ω−ペルフルオロアルカジエンを得るものである。吸湿性が高く、分解しやすく、かつ高価な有機金属化合物を使用しないことから、安価で大量生産に適した製造方法であると共に作業性及び安全性の向上も図れる。 That is, in a specific embodiment of the present invention, a tetrahalogenated perfluoroalkane that is industrially available or can be synthesized by various methods is used as a catalyst in an organic solvent such as tetrahydrofuran in the range of -78 ° C to + 200 ° C. Reacting with a metal such as Mg, Zn, Cd, Al, Cu, Na or Li in the presence of an appropriate amount of an alkyl halide to obtain a α, ω-perfluoroalkadiene in high yield by performing a dehalogenation reaction It is. Since it has high hygroscopicity, is easily decomposed, and does not use expensive organometallic compounds, it is an inexpensive manufacturing method suitable for mass production, and can also improve workability and safety.
触媒として用いられるハロゲン化アルキルは、一般式;RXで示され、Xは塩素、臭素、ヨウ素のいずれか、Rは直鎖状、分枝状、あるいは環状のアルキル基またはアリール基で示される化合物の中から選ばれる。触媒として使用されるハロゲン化アルキルの量は、原料のテトラハロゲン化ペルフルオロアルカン類に対して0.05当量から0.5当量の範囲内で行われる。0.05当量未満では触媒効果が低く、満足する収率で目的物を得ることができない。逆に0.5当量超に触媒の量を増量しても得られる効果は同様であり、コスト面から0.5当量以下が望ましい。 The alkyl halide used as the catalyst is represented by the general formula: RX, X is any one of chlorine, bromine, and iodine, and R is a compound represented by a linear, branched, or cyclic alkyl or aryl group. Selected from The amount of the alkyl halide used as the catalyst is in the range of 0.05 equivalent to 0.5 equivalent based on the tetrahalogenated perfluoroalkane as the raw material. If it is less than 0.05 equivalent, the catalytic effect is low and the desired product cannot be obtained with a satisfactory yield. Effects even if increasing the amount of catalyst back to 0.5 equivalents excess obtained is similar, in terms of cost 0.5 equivalents or less is preferable.
反応温度は、−78℃から+200℃の範囲内で行われる。
上述の有機溶媒中で、金属とハロゲン化アルキルとを加え、加熱または沸騰還流を行うことで前述式(2)から式(1)のペルフルオロアルカジエン類を製造する。
The reaction temperature is in the range of -78 ° C to + 200 ° C.
A perfluoroalkadiene represented by the formula (1) is produced from the above formula (2) by adding a metal and an alkyl halide in the above-mentioned organic solvent and performing heating or boiling reflux.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2000313523A JP4684402B2 (en) | 1999-10-26 | 2000-10-13 | Method for producing perfluoroalkadiene |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP30422799 | 1999-10-26 | ||
JP11-304227 | 1999-10-26 | ||
JP2000313523A JP4684402B2 (en) | 1999-10-26 | 2000-10-13 | Method for producing perfluoroalkadiene |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2001192347A JP2001192347A (en) | 2001-07-17 |
JP2001192347A5 true JP2001192347A5 (en) | 2007-11-29 |
JP4684402B2 JP4684402B2 (en) | 2011-05-18 |
Family
ID=26563828
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2000313523A Expired - Lifetime JP4684402B2 (en) | 1999-10-26 | 2000-10-13 | Method for producing perfluoroalkadiene |
Country Status (1)
Country | Link |
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JP (1) | JP4684402B2 (en) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100852900B1 (en) * | 2007-04-20 | 2008-08-19 | (주)후성 | Method of manufacturing perfluroalkadiene |
RU2528334C1 (en) * | 2013-05-27 | 2014-09-10 | Закрытое акционерное общество научно-производственное Объединение "ПиМ-Инвест" (ЗАО НПО "Пим-Инвест") | Method of synthesysing 6,6,7,7,8,8,8-heptafluoro-5,5-(trifluoromethyl)octadiene-1,3-prospective monomer for fluorine-containing polymers |
SG11201907182QA (en) * | 2017-02-03 | 2019-09-27 | Daikin Ind Ltd | Method for producing perfluoroalkadiene compounds |
JP7158906B2 (en) * | 2018-06-15 | 2022-10-24 | ダイキン工業株式会社 | Method for producing perfluoroalkadiene compound |
JP6813003B2 (en) * | 2018-06-15 | 2021-01-13 | ダイキン工業株式会社 | Method for producing perfluoroalkaziene compound |
KR102644481B1 (en) * | 2018-06-22 | 2024-03-07 | 가부시끼가이샤 레조낙 | Method for producing hexafluoro-1,3-butadiene |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1207496B (en) * | 1985-05-29 | 1989-05-25 | Montefluos Spa | PROCEDURE FOR THE SYNTHESIS OF HEXAFLUOROBUTADIENE AND HIGHER FLUORINATED DIENES. |
IT1199678B (en) * | 1986-11-27 | 1988-12-30 | Ausimont Spa | PROCEDURE FOR THE SYNTHESIS OF PERFLUOROALCADIENI |
JPS63162633A (en) * | 1986-12-26 | 1988-07-06 | Mitsui Petrochem Ind Ltd | Production of fluorine-containing olefin |
JP2503552B2 (en) * | 1987-12-01 | 1996-06-05 | 旭硝子株式会社 | Novel fluorinated compound and method for producing the same |
JP2503549B2 (en) * | 1987-12-01 | 1996-06-05 | 旭硝子株式会社 | Method for producing fluorine-containing compound |
JP2638105B2 (en) * | 1988-08-02 | 1997-08-06 | 旭硝子株式会社 | New fluorine-containing compound and method for producing the same |
JP2833260B2 (en) * | 1991-04-23 | 1998-12-09 | 旭硝子株式会社 | New fluorine-containing compound and method for producing the same |
-
2000
- 2000-10-13 JP JP2000313523A patent/JP4684402B2/en not_active Expired - Lifetime
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