JPH049342A - Production of perfluoralkyldurene - Google Patents
Production of perfluoralkyldureneInfo
- Publication number
- JPH049342A JPH049342A JP11080090A JP11080090A JPH049342A JP H049342 A JPH049342 A JP H049342A JP 11080090 A JP11080090 A JP 11080090A JP 11080090 A JP11080090 A JP 11080090A JP H049342 A JPH049342 A JP H049342A
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- iododurene
- iodide
- copper
- organic solvent
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims abstract description 11
- MCRSYYLHVQGFNR-UHFFFAOYSA-N 3-iodo-1,2,4,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(I)=C1C MCRSYYLHVQGFNR-UHFFFAOYSA-N 0.000 claims abstract description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052802 copper Inorganic materials 0.000 claims abstract description 5
- 239000010949 copper Substances 0.000 claims abstract description 5
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 229910052725 zinc Inorganic materials 0.000 claims abstract description 5
- 239000011701 zinc Substances 0.000 claims abstract description 5
- -1 perfluoroalkyl durene Chemical compound 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- SQNZJJAZBFDUTD-UHFFFAOYSA-N durene Natural products CC1=CC(C)=C(C)C=C1C SQNZJJAZBFDUTD-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 abstract description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract description 6
- 239000002994 raw material Substances 0.000 abstract description 5
- 150000008064 anhydrides Chemical class 0.000 abstract description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 abstract 2
- KWXGJTSJUKTDQU-UHFFFAOYSA-N 1,1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8-heptadecafluoro-8-iodooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)I KWXGJTSJUKTDQU-UHFFFAOYSA-N 0.000 abstract 1
- 239000002904 solvent Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- ZQBFAOFFOQMSGJ-UHFFFAOYSA-N hexafluorobenzene Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1F ZQBFAOFFOQMSGJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- SJBBXFLOLUTGCW-UHFFFAOYSA-N 1,3-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C(F)(F)F)=C1 SJBBXFLOLUTGCW-UHFFFAOYSA-N 0.000 description 1
- PDCBZHHORLHNCZ-UHFFFAOYSA-N 1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C=C1 PDCBZHHORLHNCZ-UHFFFAOYSA-N 0.000 description 1
- IYFUQKGDILUVJG-UHFFFAOYSA-N 1-ethyl-2,4,5-trimethylbenzene Chemical compound CCC1=CC(C)=C(C)C=C1C IYFUQKGDILUVJG-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/26—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
- C07C17/32—Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by introduction of halogenated alkyl groups into ring compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (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、パーフルオロアルキルピロメリット酸無水物
の原料として有用なパーフルオロアルキルデユレンの製
造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Application Field] The present invention relates to a method for producing perfluoroalkyldurene useful as a raw material for perfluoroalkylpyromellitic anhydride.
パーフルオロアルキルピロメリット酸無水物は、低熱膨
張係数、低誘電率、低屈折率を有するポリイミドの原料
として期待されている。Perfluoroalkylpyromellitic anhydride is expected to be a raw material for polyimide having a low coefficient of thermal expansion, low dielectric constant, and low refractive index.
該パーフルオロアルキルピロメリット酸無水物は、特開
平２−１５０８４号公報に示されるように、パーフルオ
ロアルキルデユレンを酸化、脱水することにより得られ
るが、そのためには原料となるバーフルオロアルキルデ
ュレンを先ず合成する必要がある。上記公開公報に示さ
れるパーフルオロアルキルデユレンの合成法は、ヨード
デユレンとパーフルオロアルキルヨーダイドをオートク
レーブ内で極性有機溶媒中、触媒として活性銅粉を加え
１、５０〜２５０”Ｃ，２０〜３００気圧で１０時間〜
１５０時間反応させるものである。上記公開公報には、
パーフルオロアルキルヨーダイドの炭素数が大きくなる
ほど高温、高圧、長時間を要する旨が記載される。The perfluoroalkylpyromellitic anhydride can be obtained by oxidizing and dehydrating perfluoroalkyldurene, as shown in JP-A No. 2-15084. must be synthesized first. The method for synthesizing perfluoroalkyldurene shown in the above publication involves adding activated copper powder as a catalyst to iododurene and perfluoroalkyl iodide in a polar organic solvent in an autoclave at 1,50-250"C, 20-300"C. 10 hours at atmospheric pressure
The reaction was carried out for 150 hours. In the above publication,
It is stated that the larger the number of carbon atoms in the perfluoroalkyl iodide, the higher the temperature, pressure, and time required.
また、ズルナル・オルガニチェスコイ・キミ−（Ｚｈｕ
ｒｎａｌ Ｏｒｇａｎｉｃｈｅｓｋｏｊ Ｋｈｉｍｉ）
第１ｏ巻２０００頁（１９７４年）には、ヨードデユレ
ンとトリフルオロメチルヨーダイトを銅粉及び青銅粉の
存在下、ジメチルホルムアミドを溶媒としてオートクレ
ーブ中に入れ、１５０℃で５０時間反応させて、トリフ
ルオロメチルデュレンを得ている。この場合、オートク
レーブ中の圧力は高圧になっている。Also, Zurnar Organicheskoy Kimi (Zhu
rnal Organicheskoj Khimi)
Vol. 1O, p. 2000 (1974) describes how iododurene and trifluoromethyliodite were placed in an autoclave using dimethylformamide as a solvent in the presence of copper powder and bronze powder, and reacted at 150°C for 50 hours to produce trifluoromethyliodite. I'm getting methyldurene. In this case, the pressure in the autoclave is high.
前記特開平２−１５０８４号公報及びズルナル・オルガ
ニチェスコイ・キミーに記載の方法は、いずれも高圧下
に行なわれるものであり、反応条件は厳しいものである
。特に、特開平２−１５０８４号公報には前記したよう
にパーフルオロアルキルヨーダイドの炭素数が大きくな
るほど高温、高圧、長時間が必要であり、反応条件はよ
り厳しくなる。The methods described in JP-A-2-15084 and Zrnar Organicheskoy Kimmy are both carried out under high pressure, and the reaction conditions are severe. In particular, as described in JP-A-2-15084, as the number of carbon atoms in the perfluoroalkyl iodide increases, high temperature, high pressure, and long time are required, and the reaction conditions become more severe.
しかし、本発明者らは、ヨードデユレンとパーフルオロ
アルキルヨーダイドの反応がより穏和な条件で進行する
ことを見い出し、本発明を為すに敗った。However, the present inventors found that the reaction between iododurene and perfluoroalkyl iodide proceeded under milder conditions, and the present invention was unsuccessful.
本発明におけるパーフルオロアルキルデユレンの製造法
は、ヨードデユレンと炭素数５以上のパーフルオロアル
キルヨーダイドを有機溶媒中、常圧下、６０℃乃至還流
温度で、銅又は亜鉛の存在下に反応させることを特徴と
する。The method for producing perfluoroalkyldurene in the present invention involves reacting iododurene and perfluoroalkyl iodide having 5 or more carbon atoms in an organic solvent under normal pressure at 60°C to reflux temperature in the presence of copper or zinc. It is characterized by
上記の製造法における反応式は次のとおりである。The reaction formula in the above production method is as follows.
（ただし、式中、ｎは５以上の整数である。）上記パー
フルオロアルキルヨーダイド
（ＣｎＦ２ｎ、、Ｉ ）としては、パーフルオロペンチ
ルヨーダイト、パーフルオロヘキシルヨーダイト、パー
フルオロヘプチルヨーダイト、パーフルオロオクチルヨ
ーダイト、パーフルオロノネニルヨーダイト、パーフル
オロデシルヨーダイト、パーフルオロウンデシルヨーダ
イト、パーフルオロアルキルヨーダイド等がある。パー
フルオロアルキルヨーダイドは、ヨードデユレンに対し
て当量以上で使用されるのが好ましい。(However, in the formula, n is an integer of 5 or more.) Examples of the perfluoroalkyl iodide (CnF2n, I) include perfluoropentyl iodite, perfluorohexyl iodite, perfluoroheptyl iodite, and perfluoroheptyl iodite. Examples include fluorooctyl iodite, perfluorononenyl iodite, perfluorodecyl iodite, perfluoroundecyl iodite, and perfluoroalkyl iodite. The perfluoroalkyl iodide is preferably used in an amount equal to or more than the amount of iododurene.
前記有機溶媒としては、原料を溶解することができるも
のが使用され、テトラヒドロフラン、Ｎ。The organic solvent used is one that can dissolve the raw materials, such as tetrahydrofuran, N.
Ｎ−ジメチルホルムアミド、Ｎ、Ｎ−ジメチルアセトア
ミド、ジメチルスルホキシド、Ｎ−メチル−２−ピロリ
ドンなどがあり、２種類以上を混合して用いても良い。Examples include N-dimethylformamide, N,N-dimethylacetamide, dimethylsulfoxide, and N-methyl-2-pyrrolidone, and two or more types may be used in combination.
また、上記溶媒と併用して、ヘキサフルオロベンゼン、
ペンシトリフルオライド、ｍ−キシレンへキサフルオラ
イド、ｐ−キシレンへキサフルオライド、０−キシレン
へキサフルオライドなどのフッ素系溶媒を用いることが
できる。フッ素系溶媒の使用量としては、使用溶媒全量
の３０重量％以下が好ましい。フッ素系溶媒が多すぎる
と、原料が溶媒に溶解しにくくなり収率が低下する傾向
がある。本発明で使用する溶媒は十分脱水したものを用
いることが好ましい。In addition, in combination with the above solvent, hexafluorobenzene,
Fluorine solvents such as pensitrifluoride, m-xylene hexafluoride, p-xylene hexafluoride, and 0-xylene hexafluoride can be used. The amount of the fluorine-based solvent used is preferably 30% by weight or less based on the total amount of the solvent used. If there is too much fluorine-based solvent, the raw material becomes difficult to dissolve in the solvent, and the yield tends to decrease. It is preferable that the solvent used in the present invention be sufficiently dehydrated.
前記反応は常圧下に行なわれる。The reaction is carried out under normal pressure.
反応の温度は６０℃以上である６温度が低すぎると収率
が低下する。反応時間は適宜決定すればよいが１時間以
上が好ましい。また、上限は還流温度とされる。The reaction temperature is 60°C or higher.6 If the temperature is too low, the yield will decrease. The reaction time may be determined as appropriate, but is preferably 1 hour or more. Further, the upper limit is the reflux temperature.
前記の反応は銅又は亜鉛の存在下に行なわれ、粉末状で
使用されるのが好ましく、パーフルオロアルキルヨーダ
イドに対して当量以上（特に過剰）で使用するのが好ま
しい。金属銅粉末は、テトラヘドロン（Ｔｅｔｒａ −
ｈｅｄｒｏｎ）第２５巻、５９２１頁（１９６９）やオ
ルガニツクシンセシス（ＯｒｇａｎｉｃＳｙｎｔｈｅｓ
ｉｓ）コレクティブボリュームＩＩ、４４６頁（１９４
３）に記載されている方法などにより活性化したものを
用いるのが好ましい。The above reaction is carried out in the presence of copper or zinc, preferably used in powder form, and preferably used in an amount equivalent to or more (particularly in excess) relative to the perfluoroalkyl iodide. The metallic copper powder is tetrahedron (Tetra-
hedron, Vol. 25, p. 5921 (1969) and OrganicSynthes.
is) Collective Volume II, page 446 (194
It is preferable to use one activated by the method described in 3).
また、上記反応は、窒素、アルゴンなどの不活性気体雰
囲気下に行なうのが好ましい。Further, the above reaction is preferably carried out under an inert gas atmosphere such as nitrogen or argon.
さらに、上記反応に際し、適宜２，２′−ビピリジル、
酢酸パラジウム、テトラキス（トリフェニルホスフィン
）パラジウム、ビス（トリフェニルホスフィン）パラジ
ウムクロライド、塩化パラジウム等を添加し、又は超音
波を印加することができる。Furthermore, in the above reaction, 2,2'-bipyridyl,
Palladium acetate, tetrakis(triphenylphosphine)palladium, bis(triphenylphosphine)palladium chloride, palladium chloride, etc. can be added, or ultrasonic waves can be applied.
以下、本発明を実施例により説明するが５本発明は、こ
の実施例により限定されるものではない。EXAMPLES The present invention will be explained below with reference to Examples, but the present invention is not limited to these Examples.
実施例１
かくはん装置、乾燥管、アルゴンガス導入管を備えたフ
ラスコに銅粉１．３９０ ｇ （２１，４ｍｌｌ１ｏＱ
）、パーフルオロオクチルヨーダイト２．３９ ｇ（４
，４ｍｍｏＱ）、ジメチルスルホキシド２０ｍ１２を入
れ１２０℃で３０分間加熱した。ヨードデユレン１．１
４ｇ （４，４ｍ ｏ＋ｏｎ）を添加し、１２０℃で１
５時間、常圧下に反応させた。反応終了後銅粉を０別、
ジメチルスルホキシドで十分洗浄した。０液、洗浄液を
大量の水に注ぎ、塩化メチレンで抽出した。無水硫酸マ
グネシウムで一晩乾燥し、塩化メチレンを留去し、得ら
れた結晶を乾燥した。Example 1 1.390 g of copper powder (21.4ml1oQ) was placed in a flask equipped with a stirring device, a drying tube, and an argon gas introduction tube.
), perfluorooctyl iodite 2.39 g (4
, 4mmoQ) and 20ml of dimethyl sulfoxide were added and heated at 120°C for 30 minutes. iododurene 1.1
Add 4g (4,4m o+on) and heat at 120°C.
The reaction was carried out under normal pressure for 5 hours. After the reaction is complete, remove the copper powder by
Thoroughly washed with dimethyl sulfoxide. The 0 liquid and the washing liquid were poured into a large amount of water and extracted with methylene chloride. It was dried over anhydrous magnesium sulfate overnight, methylene chloride was distilled off, and the obtained crystals were dried.
得られた結晶の収率及び物性は次の通りである。The yield and physical properties of the obtained crystals are as follows.
収率：３５．６％
融点： ５８．５℃
赤外吸収スペクトル（特徴的な吸収位置）：Ｔ Ｓ Ｋ
−ｇｅＱ Ｇ２０００ＨＸ Ｌ １本＋Ｇ１０００Ｈ
Ｘ Ｌ １本
溶 媒 テトラヒドロフラン
流量１ ｍ ｎ ／ｍｉｎ
検出器 ＲＩ
〔発明の効果〕
請求項１に記載の方法により、穏和な条件でパーフルオ
ロアルキルデユレンを製造することができる。Yield: 35.6% Melting point: 58.5°C Infrared absorption spectrum (characteristic absorption position): TSK
-geQ G2000HX L 1 piece + G1000H
X L 1 solvent Tetrahydrofuran flow rate 1 m n /min Detector RI [Effects of the Invention] By the method described in claim 1, perfluoroalkyldurene can be produced under mild conditions.
１２２０■−’（Ｃ−Ｆ）
１Ｈ−ＮＭＲスペクトル（特徴的なピーク位置）ニア、
２３ｐｐｍ （芳香族の
プロトン）
２．２〜２．４ｐｐｍ
（メチル基のプロトン）
また、得られた結晶は次の分析条件による液体クロマト
グラフィ分析で単一ピークであった。1220 ■-' (C-F) 1H-NMR spectrum (characteristic peak position) near,
23 ppm (aromatic protons) 2.2 to 2.4 ppm (methyl group protons) The obtained crystals showed a single peak when analyzed by liquid chromatography under the following analysis conditions.
分析条件：カラム 東ソー（株）製Analysis conditions: Column manufactured by Tosoh Corporation
Claims (1)
キルヨーダイドを有機溶媒中、常圧下、６０℃乃至還流
温度で、銅又は亜鉛の存在下に反応させることを特徴と
するパーフルオロアルキルデユレンの製造法。1. Production of perfluoroalkyl durene, which is characterized by reacting iododurene and perfluoroalkyl iodide having 5 or more carbon atoms in an organic solvent under normal pressure at 60°C to reflux temperature in the presence of copper or zinc. Law.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11080090A JPH049342A (en) | 1990-04-26 | 1990-04-26 | Production of perfluoralkyldurene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP11080090A JPH049342A (en) | 1990-04-26 | 1990-04-26 | Production of perfluoralkyldurene |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH049342A true JPH049342A (en) | 1992-01-14 |
Family
ID=14544971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP11080090A Pending JPH049342A (en) | 1990-04-26 | 1990-04-26 | Production of perfluoralkyldurene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH049342A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH089371A (en) * | 1994-02-28 | 1996-01-12 | Korea Telecommun | High-speed synchronous method of variable length sign using parallel processing pattern matching |
| JP2010285384A (en) * | 2009-06-12 | 2010-12-24 | Agc Seimi Chemical Co Ltd | Method for producing compound having tetrafluoroethylene backbone |
| JP2015086221A (en) * | 2013-09-27 | 2015-05-07 | 国立大学法人 東京大学 | Perfluoroalkylation reaction of aromatic compound |
-
1990
- 1990-04-26 JP JP11080090A patent/JPH049342A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH089371A (en) * | 1994-02-28 | 1996-01-12 | Korea Telecommun | High-speed synchronous method of variable length sign using parallel processing pattern matching |
| JP2010285384A (en) * | 2009-06-12 | 2010-12-24 | Agc Seimi Chemical Co Ltd | Method for producing compound having tetrafluoroethylene backbone |
| JP2015086221A (en) * | 2013-09-27 | 2015-05-07 | 国立大学法人 東京大学 | Perfluoroalkylation reaction of aromatic compound |
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