JPH07100673B2 - Process for producing 1-fluorocyclohexene - Google Patents
Process for producing 1-fluorocyclohexeneInfo
- Publication number
- JPH07100673B2 JPH07100673B2 JP61192102A JP19210286A JPH07100673B2 JP H07100673 B2 JPH07100673 B2 JP H07100673B2 JP 61192102 A JP61192102 A JP 61192102A JP 19210286 A JP19210286 A JP 19210286A JP H07100673 B2 JPH07100673 B2 JP H07100673B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- fluoride
- fluorocyclohexene
- catalyst
- difluorocyclohexane
- 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 - Lifetime
Links
- JHJLETSOSKVZGF-UHFFFAOYSA-N 1-fluorocyclohexene Chemical compound FC1=CCCCC1 JHJLETSOSKVZGF-UHFFFAOYSA-N 0.000 title claims description 10
- 238000000034 method Methods 0.000 title description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910001512 metal fluoride Inorganic materials 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 description 23
- ZORQXIQZAOLNGE-UHFFFAOYSA-N 1,1-difluorocyclohexane Chemical compound FC1(F)CCCCC1 ZORQXIQZAOLNGE-UHFFFAOYSA-N 0.000 description 7
- 239000007789 gas Substances 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 238000005796 dehydrofluorination reaction Methods 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 4
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 3
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- AZQRVGXSORXOCR-UHFFFAOYSA-N 1-bromo-2-fluorocyclohexane Chemical compound FC1CCCCC1Br AZQRVGXSORXOCR-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229910021582 Cobalt(II) fluoride Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 2
- 229910001634 calcium fluoride Inorganic materials 0.000 description 2
- YCYBZKSMUPTWEE-UHFFFAOYSA-L cobalt(ii) fluoride Chemical compound F[Co]F YCYBZKSMUPTWEE-UHFFFAOYSA-L 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 2
- ORUIBWPALBXDOA-UHFFFAOYSA-L magnesium fluoride Chemical compound [F-].[F-].[Mg+2] ORUIBWPALBXDOA-UHFFFAOYSA-L 0.000 description 2
- 229910001635 magnesium fluoride Inorganic materials 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- AHLATJUETSFVIM-UHFFFAOYSA-M rubidium fluoride Chemical compound [F-].[Rb+] AHLATJUETSFVIM-UHFFFAOYSA-M 0.000 description 2
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 2
- WXZPTPUIYMOMRA-UHFFFAOYSA-N 1-chloro-1-fluorocyclohexane Chemical compound FC1(Cl)CCCCC1 WXZPTPUIYMOMRA-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910001515 alkali metal fluoride Inorganic materials 0.000 description 1
- 229910001618 alkaline earth metal fluoride Inorganic materials 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- OYLGJCQECKOTOL-UHFFFAOYSA-L barium fluoride Chemical compound [F-].[F-].[Ba+2] OYLGJCQECKOTOL-UHFFFAOYSA-L 0.000 description 1
- 229910001632 barium fluoride Inorganic materials 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007033 dehydrochlorination reaction Methods 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- FZGIHSNZYGFUGM-UHFFFAOYSA-L iron(ii) fluoride Chemical compound [F-].[F-].[Fe+2] FZGIHSNZYGFUGM-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DBJLJFTWODWSOF-UHFFFAOYSA-L nickel(ii) fluoride Chemical compound F[Ni]F DBJLJFTWODWSOF-UHFFFAOYSA-L 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000013024 sodium fluoride Nutrition 0.000 description 1
- 239000011775 sodium fluoride Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 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)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は１−フルオロシクロヘキセンの新規な製造法に
関するものである。TECHNICAL FIELD The present invention relates to a novel method for producing 1-fluorocyclohexene.
従来１−フルオロシクロヘキセンは、シス−１−ブロモ
−２−フルオロシクロヘキサンを強塩基で脱臭化水素す
る方法〔ベリヒテ（Ber.）,96巻,329頁（1963）〕、１
−クロロ−１−フルオロシクロヘキサンを触媒の存在下
に脱塩化水素する方法〔ヘルベチカ・ヒミカ・アクタ
（Helvetica Chimica Acta）,46巻,1818頁（1963）〕、
1,1−ジフルオロシクロヘキサンをアルミナにより脱フ
ツ化水素する方法〔ジヤーナル・オブ・オーガツク・ケ
ミストリー（J.Org.Chem.）、36巻、818頁（1971）〕な
どにより合成されている。Conventionally, 1-fluorocyclohexene is a method of dehydrobrominating cis-1-bromo-2-fluorocyclohexane with a strong base [Berichte (Ber.), 96, 329 (1963)], 1
A method for dehydrochlorinating -chloro-1-fluorocyclohexane in the presence of a catalyst [Helvetica Chimica Acta, 46, 1818 (1963)],
It is synthesized by a method of dehydrofluorination of 1,1-difluorocyclohexane with alumina [Journal of Organic Chemistry (J.Org.Chem.), 36, 818 (1971)].
しかしながら従来の方法には様々な欠点があつた。例え
ばシス−１−ブロモ−２−フルオロシクロヘキサンの脱
臭化水素による方法ではカリウム・ターシヤリーブドキ
シド等の高価な塩基を使用しなければならない。１−ク
ロロ−１−フルオロシクロヘキサンの脱塩化水素による
方法は収率が低い。またアルミナを用いて1,1−ジフル
オロシクロヘキサンの脱フツ化水素を行う方法では、脱
フツ化水素剤として極めて大量のアルミナを使用せねば
ならず、実用的ではない。However, the conventional method has various drawbacks. For example, in the method using dehydrobromide of cis-1-bromo-2-fluorocyclohexane, an expensive base such as potassium tert-butyroxide must be used. The method using dehydrochlorination of 1-chloro-1-fluorocyclohexane has a low yield. Further, the method of dehydrofluorination of 1,1-difluorocyclohexane using alumina requires an extremely large amount of alumina as a dehydrofluorination agent, which is not practical.
本発明者らは鋭意研究を重ねた結果、１−フルオロシク
ロヘキセンを製造する新規な方法を見出すに至つた。す
なわち本発明は、1,1−ジフルオロシクロヘキサンから
１−フルオロシクロヘキセンを製造するに当り、触媒と
して金属フツ化物を用いる方法を提供するものである。As a result of intensive studies, the present inventors have found a new method for producing 1-fluorocyclohexene. That is, the present invention provides a method of using a metal fluoride as a catalyst in producing 1-fluorocyclohexene from 1,1-difluorocyclohexane.
本反応では次式に示すように1,1−ジフルオロシクロヘ
キサンが触媒の存在で１分子のフツ化水素を脱離して１
−フルオロシクロヘキセンを生成する。In this reaction, 1,1-difluorocyclohexane desorbs one molecule of hydrogen fluoride in the presence of a catalyst to give 1
-Produces fluorocyclohexene.
本発明で原料として用いる1,1−ジフルオロシクロヘキ
サンはどのような方法で製造されたものでもよい。 The 1,1-difluorocyclohexane used as a raw material in the present invention may be produced by any method.
本発明において触媒として使用される金属フツ化物とし
ては、例えば、フツ化リチウム、フツ化ナトリウム、フ
ツ化カリウム、フツ化ルビジウム、フツ化セシウム等の
アルカリ金属フツ化物；フツ化マグネシウム、フツ化カ
ルシウム、フツ化ストロンチウム、フツ化バリウム等の
アルカリ土類金属フツ化物；フツ化鉄（II）、フツ化鉄
（III）、フツ化コバルト（II）、フツ化コバルト（II
I）、フツ化ニツケル等のVIII族金属フツ化物；フツ化
アルミニウム、フツ化ガリウム等の土類金属フツ化物な
どをあげることができる。特にフツ化リチウム、フツ化
マグネシウム、フツ化カリシウム、フツ化鉄、フツ化ア
ルミニウムなどが好ましく用いられる。これらの金属フ
ツ化物はそれぞれ単独で、あるいは混在させて使用する
ことができる。またこれらの金属フツ化物を担体に担持
させて用いることも可能である。Examples of the metal fluoride used as a catalyst in the present invention include lithium fluoride, sodium fluoride, potassium fluoride, rubidium fluoride, cesium fluoride, and other alkali metal fluorides; magnesium fluoride, calcium fluoride, Alkaline earth metal fluorides such as strontium fluoride and barium fluoride; iron (II) fluoride, iron (III) fluoride, cobalt (II) fluoride, cobalt (II) fluoride
I), Group VIII metal fluorides such as nickel fluoride; and earth metal fluorides such as aluminum fluoride and gallium fluoride. In particular, lithium fluoride, magnesium fluoride, calcium fluoride, iron fluoride, aluminum fluoride and the like are preferably used. These metal fluorides can be used alone or in combination. It is also possible to use these metal fluorides supported on a carrier.
本発明において使用することのできる反応の様式として
は、流動床式、固定床式、あるいは撹拌式等があげら
れ、流通式、回分式いずれの方法であつてもよいが、特
に気相流通式が好ましい。Examples of the reaction mode that can be used in the present invention include a fluidized bed system, a fixed bed system, or a stirring system, and may be a flow system or a batch system, but a gas phase flow system is particularly preferable. Is preferred.
本発明では反応系に窒素、アルゴン、ヘリウム等の不溶
性ガスが存在していても良い。また反応を液相で行なう
場合には、不活性な溶媒を用いることもできる。In the present invention, an insoluble gas such as nitrogen, argon or helium may be present in the reaction system. Further, when the reaction is carried out in a liquid phase, an inert solvent can be used.
また反応圧力は特に制限はなく、原料の1,1−ジフルオ
ロシクロヘキサンは反応系において液相、気相あるいは
気液混相のいずれであつてもよい。The reaction pressure is not particularly limited, and the raw material 1,1-difluorocyclohexane may be in a liquid phase, a gas phase or a gas-liquid mixed phase in the reaction system.
反応温度は脱フツ化水素反応の平衡の点から、また反応
速度を向上させるためには高温が有利であるが、副反応
等の問題から、あまり高い温度は好ましくない。本発明
においては反応温度は使用する触媒の種類、および用い
る反応も様式等によつて異なるが、気相反応の場合には
通常100〜700℃、好ましくは150〜500℃で行われ、液相
反応の場合には通常50〜400℃、好ましくは80〜300℃で
行われる。The reaction temperature is advantageous from the viewpoint of equilibrium of the dehydrofluorination reaction, and a high temperature is advantageous for improving the reaction rate, but a too high temperature is not preferable due to problems such as side reactions. In the present invention, the reaction temperature is different depending on the type of catalyst used, and the reaction used also depending on the mode etc., but in the case of a gas phase reaction, it is usually carried out at 100 to 700 ° C., preferably 150 to 500 ° C. In the case of the reaction, it is usually carried out at 50 to 400 ° C, preferably 80 to 300 ° C.
また反応時間は反応温度、触媒の種類、反応の様式等に
より異なるが、気相流通式反応の場合には接触時間で表
現して0.001〜50秒、好ましくは0.1秒〜10秒で行なわれ
る。液相反応の場合には、通常５分〜100時間、好まし
くは５分〜10時間で行なわれる。The reaction time varies depending on the reaction temperature, the type of catalyst, the mode of reaction, etc., but in the case of the gas phase flow type reaction, it is 0.001 to 50 seconds, preferably 0.1 to 10 seconds, expressed as the contact time. In the case of a liquid phase reaction, it is usually carried out for 5 minutes to 100 hours, preferably 5 minutes to 10 hours.
触媒と原料の量比は反応の様式や反応条件等によつても
変り得るが、気相流通式の場合にはWHSVで表現して通常
0.001〜100、好ましくは0.01〜50で行なわれる。また液
相回分式の場合には反応原料に対する触媒の重量比で表
現して通常0.0001〜0.5、好ましくは0.001〜0.1の範囲
で使用される。The amount ratio of the catalyst and the raw material may vary depending on the reaction mode, reaction conditions, etc., but in the case of the gas phase flow system, it is usually expressed as WHSV.
It is carried out at 0.001 to 100, preferably 0.01 to 50. In the case of the liquid phase batch system, it is usually used in the range of 0.0001 to 0.5, preferably 0.001 to 0.1 expressed as the weight ratio of the catalyst to the reaction raw material.
本発明によれば、１−フルオロシクロヘキセンを高収率
・高選択率で得ることができる。According to the present invention, 1-fluorocyclohexene can be obtained in high yield and high selectivity.
以下に実施例を示し、本発明を具体的に述べる。 Hereinafter, the present invention will be specifically described with reference to examples.
実施例１ 内径1.5cmのステンレス製の管状反応器にフツ化アルミ
ニウム（粒径約0.3mm）5gを充填し、加熱した。この反
応器に1,1−ジフルオロシクロヘキサンを15g/時の流量
で導入した。同時に窒素を400ml/分の流量で導入した。
反応は350〜360℃の範囲で行つた。反応が定常状態にな
つた後、反応生成物をドライアイストラツプで補集し
た。反応混合物を炭酸水素ナトリウム水溶液で洗浄した
後にガスクロマトグラフイーによつて分析した結果、1,
1−ジフルオロシクロヘキサンの転化率は91％で、１−
フルオロシクロヘキセンが収率90％、選択率99％で生成
していた。Example 1 A tubular reactor made of stainless steel and having an inner diameter of 1.5 cm was filled with 5 g of aluminum fluoride (particle size: about 0.3 mm) and heated. 1,1-Difluorocyclohexane was introduced into the reactor at a flow rate of 15 g / hour. At the same time, nitrogen was introduced at a flow rate of 400 ml / min.
The reaction was carried out in the range of 350 to 360 ° C. After the reaction reached a steady state, the reaction product was collected with a dry ice trap. The reaction mixture was washed with an aqueous solution of sodium hydrogen carbonate and analyzed by gas chromatography.
The conversion rate of 1-difluorocyclohexane is 91%,
Fluorocyclohexene was produced with a yield of 90% and a selectivity of 99%.
なお、生成物の同定はガスクロマトグラフイー及びGC−
MSによつて行つた。The products were identified by gas chromatography and GC-
I went by MS.
実施例２〜７ 導入する原料の流量、反応温度、触媒等を変更した他は
実施例１と同様に行つた。反応条件及び結果を表に示
す。Examples 2 to 7 The same procedure as in Example 1 was carried out except that the flow rate of the raw material to be introduced, the reaction temperature, the catalyst and the like were changed. The reaction conditions and results are shown in the table.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｂ０１Ｊ 27/138 Ｘ Ｃ０７Ｂ 61/00 ３００ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location B01J 27/138 X C07B 61/00 300
Claims (1)
ルオロシクロヘキセンを製造するに当り、触媒として金
属フッ化物を用いることを特徴とする１−フルオロシク
ロヘキセンの製造法1. A method for producing 1-fluorocyclohexene, which comprises using a metal fluoride as a catalyst in producing 1-fluorocyclohexene from 1-difluorocyclohexane.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61192102A JPH07100673B2 (en) | 1986-08-19 | 1986-08-19 | Process for producing 1-fluorocyclohexene |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61192102A JPH07100673B2 (en) | 1986-08-19 | 1986-08-19 | Process for producing 1-fluorocyclohexene |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6348235A JPS6348235A (en) | 1988-02-29 |
| JPH07100673B2 true JPH07100673B2 (en) | 1995-11-01 |
Family
ID=16285686
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61192102A Expired - Lifetime JPH07100673B2 (en) | 1986-08-19 | 1986-08-19 | Process for producing 1-fluorocyclohexene |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH07100673B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007320874A (en) * | 2006-05-31 | 2007-12-13 | Nippon Zeon Co Ltd | Method for producing perfluoroalkyne compound |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0946472B1 (en) * | 1996-11-21 | 2002-09-04 | E.I. Du Pont De Nemours And Company | The catalytic manufacture of vinyl fluoride |
| JP6835060B2 (en) * | 2018-12-27 | 2021-02-24 | ダイキン工業株式会社 | Cyclobutene manufacturing method |
-
1986
- 1986-08-19 JP JP61192102A patent/JPH07100673B2/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007320874A (en) * | 2006-05-31 | 2007-12-13 | Nippon Zeon Co Ltd | Method for producing perfluoroalkyne compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6348235A (en) | 1988-02-29 |
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