JPH037651B2 - - Google Patents
Info
- Publication number
- JPH037651B2 JPH037651B2 JP19279484A JP19279484A JPH037651B2 JP H037651 B2 JPH037651 B2 JP H037651B2 JP 19279484 A JP19279484 A JP 19279484A JP 19279484 A JP19279484 A JP 19279484A JP H037651 B2 JPH037651 B2 JP H037651B2
- Authority
- JP
- Japan
- Prior art keywords
- acid ester
- heptafluoroisobutenyl
- alcohol
- ether
- alkyl ether
- 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
- -1 hexafluoroisobutanoic acid ester Chemical class 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 150000005215 alkyl ethers Chemical class 0.000 description 4
- 238000005796 dehydrofluorination reaction Methods 0.000 description 4
- FSDLLONBRLBIBL-UHFFFAOYSA-N 1,3,3,3-tetrafluoro-1-methoxy-2-(trifluoromethyl)prop-1-ene Chemical compound COC(F)=C(C(F)(F)F)C(F)(F)F FSDLLONBRLBIBL-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- BSZWZZSFVRISOG-UHFFFAOYSA-N 1-ethoxy-1,3,3,3-tetrafluoro-2-(trifluoromethyl)prop-1-ene Chemical compound CCOC(F)=C(C(F)(F)F)C(F)(F)F BSZWZZSFVRISOG-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- JGGBVFLRNNDHCM-UHFFFAOYSA-N methyl 3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound COC(=O)C(C(F)(F)F)C(F)(F)F JGGBVFLRNNDHCM-UHFFFAOYSA-N 0.000 description 2
- DAFIBNSJXIGBQB-UHFFFAOYSA-N perfluoroisobutene Chemical compound FC(F)=C(C(F)(F)F)C(F)(F)F DAFIBNSJXIGBQB-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- LCRBBUPAHHPMMY-UHFFFAOYSA-N 1,3,3,3-tetrafluoro-1-[1,3,3,3-tetrafluoro-2-(trifluoromethyl)prop-1-enoxy]-2-(trifluoromethyl)prop-1-ene Chemical compound FC(F)(F)C(C(F)(F)F)=C(F)OC(F)=C(C(F)(F)F)C(F)(F)F LCRBBUPAHHPMMY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RAEAYTICAPHWJW-UHFFFAOYSA-N 3,3,3-trifluoro-2-(trifluoromethyl)propanoic acid Chemical compound OC(=O)C(C(F)(F)F)C(F)(F)F RAEAYTICAPHWJW-UHFFFAOYSA-N 0.000 description 1
- KMTDMTZBNYGUNX-UHFFFAOYSA-N 4-methylbenzyl alcohol Chemical compound CC1=CC=C(CO)C=C1 KMTDMTZBNYGUNX-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- HOSPDBQHPFVHEZ-UHFFFAOYSA-N ethyl 3,3,3-trifluoro-2-(trifluoromethyl)propanoate Chemical compound CCOC(=O)C(C(F)(F)F)C(F)(F)F HOSPDBQHPFVHEZ-UHFFFAOYSA-N 0.000 description 1
- 238000007701 flash-distillation Methods 0.000 description 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 description 1
- 239000002920 hazardous waste Substances 0.000 description 1
- HCDGVLDPFQMKDK-UHFFFAOYSA-N hexafluoropropylene Chemical compound FC(F)=C(F)C(F)(F)F HCDGVLDPFQMKDK-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 239000003444 phase transfer catalyst Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本発明は、ヘキサフルオロイソブタン酸エステ
ルの製造法に関する。更に詳しくは、オクタフル
オロイソブテンの有効利用を目的とするヘキサフ
ルオロイソブタン酸エステルの製造法に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a method for producing hexafluoroisobutanoic acid ester. More specifically, the present invention relates to a method for producing hexafluoroisobutanoic acid ester for the purpose of effectively utilizing octafluoroisobutene.
ヘキサフルオロイソブタン酸エステルの合成
は、従来オクタフルオロイソブチルエーテル
（CF3）2CHCF2ORをオートクレーブ中で濃硫酸と
加熱する方法によつて行われている（Izvest
Akad Nauk S.S.S.R.Otdel Khim Nauk 1956
年第1353〜1360頁）。しかしながら、この方法は
濃硫酸を反応剤に用いることによる装置の腐食、
有害なフルオロ硫酸の副生などという問題があ
り、また反応混合物中からの目的物たるエステル
の分離操作が困難であるという欠点を有してい
る。
The synthesis of hexafluoroisobutanoic acid ester has conventionally been carried out by heating octafluoroisobutyl ether (CF 3 ) 2 CHCF 2 OR with concentrated sulfuric acid in an autoclave (Izvest
Akad Nauk SSSROtdel Khim Nauk 1956
1353-1360). However, this method suffers from corrosion of the equipment due to the use of concentrated sulfuric acid as a reactant.
There are problems such as the production of harmful fluorosulfuric acid as a by-product, and it also has the disadvantage that it is difficult to separate the target ester from the reaction mixture.
上記方法において、そもそも出発原料として用
いられているオクタフルオロイソブテンは、含フ
ツ素共重合体の重要な原料の一種であるヘキサフ
ルオロプロペン製造時の副生物であり、この毒性
の強いオクタフルオロイソブテンは、一般に低級
アルコール、例えばメタノール、エタノール、ｎ
−プロパノール、イソプロパノール、ｎ−ブタノ
ールなどとアルコール付加物を容易に形成する性
質を有している。従つて、このようなオクタフル
オロイソブチルエーテルの使用は、有害な廃棄物
の有効利用ともなる好ましい方法ではあるが、前
記したヘキサフルオロイソブタン酸エステルの製
造法は、必ずしも適当な方法とはいえないのであ
る。
In the above method, octafluoroisobutene, which is originally used as a starting material, is a by-product during the production of hexafluoropropene, which is an important raw material for fluorine-containing copolymers. , generally lower alcohols such as methanol, ethanol, n
- It has the property of easily forming alcohol adducts with propanol, isopropanol, n-butanol, etc. Therefore, although the use of octafluoroisobutyl ether is a preferable method for effectively utilizing hazardous waste, the method for producing hexafluoroisobutanoic acid ester described above is not necessarily an appropriate method. be.
本発明者は、前記したような欠点を有しないヘ
キサフルオロイソブタン酸エステルの新規の製造
法を求めて種々検討の結果、オクタフルオロイソ
ブチルエーテルを公知の方法などによつて一旦ヘ
プタフルオロイソブテニルエーテルに変換させ、
しかる後にこれをアルコールと反応させることに
より、上記課題が有効に解決されることを見出し
た。 As a result of various studies in search of a new method for producing hexafluoroisobutanoic acid ester that does not have the above-mentioned drawbacks, the present inventors have determined that octafluoroisobutyl ether is first converted into heptafluoroisobutenyl ether by a known method. Convert it to
It has been found that the above problem can be effectively solved by subsequently reacting this with alcohol.
〔問題点を解決するための手段〕および〔作用〕
従つて、本発明はヘキサフルオロイソブタン酸
エステルの製造法に係り、ヘキサフルオロイソブ
タン酸エステルの製造は、ヘプタフルオロイソブ
テニルアルキルエーテルをアルコールと反応させ
ることにより行われる。[Means for Solving the Problems] and [Operation] Therefore, the present invention relates to a method for producing hexafluoroisobutanoic acid ester, and the production of hexafluoroisobutanoic acid ester involves mixing heptafluoroisobutenyl alkyl ether with alcohol. This is done by reacting.
前述の如く、ヘプタフルオロイソブテニルアル
キルエーテルは、オクタフルオロイソブチルアル
キルエーテルを脱フツ化水素化することにより容
易に得ることができる（例えば、特開昭59−
104364号公報）。 As mentioned above, heptafluoroisobutenyl alkyl ether can be easily obtained by dehydrofluorination of octafluoroisobutyl alkyl ether (e.g., JP-A-59-1999).
104364).
（CF3）2CHCF2OR-HF→
（CF3）2C＝CFOR
この脱フツ化水素化反応は、第４級アンモニウ
ム塩などの相間移動触媒の存在下に、アルカリ金
属またはアルカリ土類金属の水酸化物または炭酸
塩あるいはトリアルキルアミンなどの塩基と共に
撹拌することにより行われ、ヘプタフルオロイソ
ブテニルアルキルエーテルはフラツシユ蒸留およ
び通常の蒸留により分離される。 (CF 3 ) 2 CHCF 2 OR -HF → (CF 3 ) 2 C=CFOR This dehydrofluorination reaction is performed using an alkali metal or alkaline earth metal in the presence of a phase transfer catalyst such as a quaternary ammonium salt. The heptafluoroisobutenyl alkyl ether is separated by flash distillation and conventional distillation.
ヘプタフルオロイソブテニルアルキルエーテル
を用いてのヘキサフルオロイソブタン酸エステル
の製造は、ヘプタフルオロイソブテニルアルキル
エーテルに対して等モル量以上、一般には１〜20
倍モルのアルコール、例えばメタノール、エタノ
ール、ｎ−プロパノール、イソプロパノール、ｎ
−ブタノール、オクタノール、シクロヘキサノー
ル、α−シクロヘキシルメタノール、ベンジルア
ルコール、ｐ−メチルベンジルアルコール、アリ
ールアルコール、プロパギルアルコールなどを加
え、加熱還流することにより行われる。 In the production of hexafluoroisobutanoic acid ester using heptafluoroisobutenyl alkyl ether, the amount of hexafluoroisobutanoic acid ester is equal to or more than that of heptafluoroisobutenyl alkyl ether, generally 1 to 20
twice the molar amount of alcohol, such as methanol, ethanol, n-propanol, isopropanol, n
-Butanol, octanol, cyclohexanol, α-cyclohexylmethanol, benzyl alcohol, p-methylbenzyl alcohol, aryl alcohol, propargyl alcohol, etc. are added and heated to reflux.
なお、オクタフルオロイソブチルアルキルエー
テルの塩基による脱フツ化水素化およびそれによ
つて生成したヘプタフルオロイソブテニルアルキ
ルエーテルとアルコールとの反応によるヘキサフ
ルオロイソブタン酸エステルの製造は、これを１
工程として行なうこともでき、即ちオクタフルオ
ロイソブチルアルキルエーテルに塩基およびアル
コールを一緒に加え、上記２工程の反応と同様の
反応機構をとることにより、ヘキサフルオロイソ
ブタン酸エステルを得ることもできる。 In addition, the production of hexafluoroisobutanoic acid ester by dehydrofluorination of octafluoroisobutyl alkyl ether with a base and the reaction of the resulting heptafluoroisobutyl alkyl ether with an alcohol is performed using 1.
It can also be carried out as a step, that is, hexafluoroisobutanoic acid ester can be obtained by adding a base and an alcohol together to octafluoroisobutyl alkyl ether and following a reaction mechanism similar to the reaction in the above two steps.
本発明方法によれば、出発原料としてオクタフ
ルオロイソブチルアルキルエーテルを塩基で脱フ
ツ化水素化することにより容易に得られるヘプタ
フルオロイソブテニルアルキルエーテルを用いる
ことができ、目的物たるヘキサフルオロイソブタ
ン酸エステルはそれをアルコールと加熱還流する
だけで合計２工程または１工程で容易に得ること
ができるので、前記従来技術にみられたような次
点をもはや有しない。しかも、その収率も良好で
ある。
According to the method of the present invention, heptafluoroisobutenyl alkyl ether, which is easily obtained by dehydrofluorination of octafluoroisobutyl alkyl ether with a base, can be used as a starting material, and the target product, hexafluoroisobutanoic acid, can be used as a starting material. Since the ester can be easily obtained by simply heating and refluxing it with the alcohol in a total of two steps or in one step, it no longer has the runner-up properties seen in the prior art. Moreover, the yield is also good.
得られたヘキサフルオロイソブタン酸エステル
は、エステル基の種類に応じて含フツ素単量体、
界面活性剤などの中間原料あるいは溶剤などの用
途に有効に用いることができる。 The obtained hexafluoroisobutanoic acid ester may contain fluorine-containing monomers,
It can be effectively used as an intermediate raw material such as a surfactant or as a solvent.
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
ジムロート冷却管、温度計、滴下ロートおよび
撹拌装置を備えた容量１のフラスコに、オクタ
フルオロイソブチルメチルエーテル200ｇ（0.862
モル）およびテトラメチルアンモニウムクロライ
ド5.1ｇ（2.55重量％）を仕込み、内容物の温度
を10〜20℃に保ちながら、85％水酸化カリウム
133ｇ（2.015モル：2.3当量）を水120mlに溶解さ
せた溶液を30分間の間に滴下した。滴下終了後１
時間撹拌し、分液、水洗して、ヘプタフルオロイ
ソブテニルメチルエーテル（沸点102〜104℃）を
175ｇ（収率95.8％）得た。Example 1 Into a capacity 1 flask equipped with a Dimroth condenser, thermometer, addition funnel and stirrer, 200 g of octafluoroisobutyl methyl ether (0.862
mol) and tetramethylammonium chloride (2.55% by weight), and while maintaining the temperature of the contents at 10 to 20℃, 85% potassium hydroxide was added.
A solution of 133 g (2.015 moles: 2.3 equivalents) dissolved in 120 ml of water was added dropwise over a period of 30 minutes. After finishing dropping 1
Stir for hours, separate the liquid, wash with water, and remove heptafluoroisobutenyl methyl ether (boiling point 102-104℃).
175g (yield 95.8%) was obtained.
このヘプタフルオロイソブテニルメチルエーテ
ル15.1ｇ（0.071モル）およびメタノール20ｇ
（0.625モル：8.8当量）を、前記と同様装置の容
量100mlのフラスコに仕込み、15時間還流させ、
その後水中に注いだ。ヘキサフルオロイソブタン
酸メチル（沸点90〜92℃）が12.1ｇ（収率80.9
％）得られた。 15.1 g (0.071 mol) of this heptafluoroisobutenyl methyl ether and 20 g of methanol
(0.625 mol: 8.8 equivalent) was charged into a 100 ml flask using the same device as above, and refluxed for 15 hours.
Then poured it into the water. 12.1g (yield 80.9) of methyl hexafluoroisobutanoate (boiling point 90-92℃)
%) obtained.
実施例 ２
ヘプタフルオロイソブテニルメチルエーテル
12.7ｇ（0.060モル）およびエタノール20ｇ
（0.435モル：7.2当量）を用い、実施例１と同様
に反応させると、ヘキサフルオロイソブタン酸エ
チル（沸点103〜105℃）が10.8ｇ（収率80.5％）
得られた。Example 2 Heptafluoroisobutenyl methyl ether
12.7g (0.060mol) and 20g ethanol
(0.435 mol: 7.2 equivalents) and reacted in the same manner as in Example 1, yielding 10.8 g (yield 80.5%) of ethyl hexafluoroisobutanoate (boiling point 103-105°C).
Obtained.
実施例 ３
前記と同様装置の容量50mlのフラスコに、オク
タフルオロイソブチルエチルエーテル13.2ｇ
（0.053モル）およびテトラメチルアンモニウムク
ロライド1.0ｇ（7.58重量％）を仕込み、内容物
の温度を10〜20℃に保ちながら、85％水酸化カリ
ウム7.0ｇ（0.106モル：2.0当量）を水20mlに溶解
させた溶液を20分間の間に滴下した。滴下終了後
１時間撹拌し、分液、水洗して、ヘプタフルオロ
イソブテニルエチルエーテル（沸点112〜114℃）
を10.2ｇ（収率84.1％）得た。Example 3 13.2 g of octafluoroisobutyl ethyl ether was placed in a 50 ml flask using the same equipment as above.
(0.053 mol) and 1.0 g (7.58% by weight) of tetramethylammonium chloride, and while maintaining the temperature of the contents at 10 to 20°C, 7.0 g (0.106 mol: 2.0 equivalent) of 85% potassium hydroxide was added to 20 ml of water. The dissolved solution was added dropwise over a period of 20 minutes. After completion of the dropwise addition, stir for 1 hour, separate the liquid, wash with water, and prepare heptafluoroisobutenyl ethyl ether (boiling point 112-114℃).
10.2g (yield 84.1%) of the product was obtained.
このヘプタフルオロイソブテニルエチルエーテ
ル4.0ｇ（0.018モル）およびメタノール10ｇ
（0.313モル：7.7当量）を、前記装置と同様の容
量50mlのフラスコに仕込み、15時間還流させ、そ
の後水中に注いだ。ヘキサフルオロイソブタン酸
メチル（沸点90〜92℃）が2.9ｇ（収率78.0％）
得られた。 4.0 g (0.018 mol) of this heptafluoroisobutenyl ethyl ether and 10 g of methanol
(0.313 mol: 7.7 equivalents) was charged into a 50 ml flask similar to the above apparatus, refluxed for 15 hours, and then poured into water. 2.9g (yield 78.0%) of methyl hexafluoroisobutanoate (boiling point 90-92℃)
Obtained.
Claims (1)
ルをアルコールと反応させることを特徴とするヘ
キサフルオロイソブタン酸エステルの製造法。1. A method for producing hexafluoroisobutanoic acid ester, which comprises reacting heptafluoroisobutenyl alkyl ether with alcohol.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19279484A JPS6169745A (en) | 1984-09-14 | 1984-09-14 | Production of hexafluoroisobutanoic acid ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19279484A JPS6169745A (en) | 1984-09-14 | 1984-09-14 | Production of hexafluoroisobutanoic acid ester |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6169745A JPS6169745A (en) | 1986-04-10 |
| JPH037651B2 true JPH037651B2 (en) | 1991-02-04 |
Family
ID=16297099
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19279484A Granted JPS6169745A (en) | 1984-09-14 | 1984-09-14 | Production of hexafluoroisobutanoic acid ester |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6169745A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3945147A1 (en) | 2020-07-28 | 2022-02-02 | Novel Crystal Technology, Inc. | Single crystal manufacturing apparatus and method |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4739123A (en) * | 1985-10-21 | 1988-04-19 | Daiken Industries, Ltd. | Fluorine-containing compounds, and their preparation and use |
| US6023002A (en) * | 1998-01-26 | 2000-02-08 | 3M Innovative Properties Company | Process for preparing hydrofluoroethers |
| US6849194B2 (en) | 2000-11-17 | 2005-02-01 | Pcbu Services, Inc. | Methods for preparing ethers, ether compositions, fluoroether fire extinguishing systems, mixtures and methods |
| JP4883155B2 (en) * | 2009-08-24 | 2012-02-22 | マックス株式会社 | Air cleaner |
-
1984
- 1984-09-14 JP JP19279484A patent/JPS6169745A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3945147A1 (en) | 2020-07-28 | 2022-02-02 | Novel Crystal Technology, Inc. | Single crystal manufacturing apparatus and method |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6169745A (en) | 1986-04-10 |
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| LAPS | Cancellation because of no payment of annual fees |